Source Book

of
Flavors
Source Book
of
Flavors
Second Edition

Edited by
Gary Reineccius

SPRINGER-SCIENCE+BUSINESS MEDIA. B.V.

Copyright © 1994 by Springer Science+Business Media Dordrecht
Originally published by Chapman & Hall in 1994
Softcover reprint ofthe hardcover 2nd edition 1994

All rights reserved. No part of this book may be reprinted or utilized in any form or by any electronic,
mechanical or other means, now known or hereafter invented, including photocopying and recording,
or by an information storage or retrieval system, without permission in writing from the publishers.
Library of Congress Cataloging in Publication Data

Source book of flavors 1edited by Gary Reineccius. - 2nd ed.

p. cm.
Rev. ed. of: Source book of flavors 1Henry B. Heath. c 1981.
"An AVI Book."
Includes bibliographica1 references and index.
ISBN 978-1-4615-7891-8 ISBN 978-1-4615-7889-5 (eBook)
DOI 10.1007/978-1-4615-7889-5
1. Flavoring essences. 2. Flavor. 3. Food-Analysis.
1. Reineccius, Gary. Il. Heath, Henry B. Source book of flavors.
TP418.S68 1992
664' .5-dc20 92-24412
CIP

British Library Cataloguing in Publication Data available

To Henry Heath
This book would not exist without
his initial monumental effort
Contents

Preface xiii

Acknowledgments xv

Contributors xvi

I. The Flavor Industry I

Overview 1
Relationships 5
Flavors of the Future 8
Organizations of the Flavor Industry 12
Associations Related to the Flavor Industry 15
Standardization of Food and Flavoring Materials 15
Information Services 20
References 22

2. FlavorAnalysis 24
Sample Preparation 25
Isolation of Food Flavors 26
Concentration of Dilute Organic and Aqueous Flavor
Isolates 42
Flavor Analysis by Direct Injection 44
Gas Chromatography 45
High Pressure Liquid Chromatography 50
Supercritical Fluid Chromatography 51
Identification of Volatile Flavors 51
Summary 51
References 52
vii
viii Contents

3. Flavor Chemistry 61
Introduction 61
Flavor Formation in Plants 62
Chemistry of Essential Oils 74
Fruit Flavors 86
Flavor of Dairy Products 88
Fungi 93
Black Tea Aroma 94
Flavor Formation During Thermal Processing 94
Flavors Formed Via Fermentation 100
References 106

4. Off-Flavors in Foods 116

Environmental Contamination 116
Off-Flavors Due to Genetics or Diet 125
Off-Flavors Due to Chemical Changes in the Food 126
Microbial Off-Flavors 131
Summary 133
References 133

5. Process Flavors Charles Manley 139

Introduction 139
The Thermally Processed Flavors (Meat and Savory
Flavors) 140
Enzyme Modification and Fermentation- The Dairy
Flavors 144
Regulatory Issues 149
Appendix 5.1 I 0 PI Guidelines for the Production and
Labeling of Process Flavors 150
References 152

6. Biotechnology for the Production of Flavoring

Materials Susan Harlander 155
Why Biotechnology? 155
Definition of"Natural" 156
Plant Tissue Culture-Derived Flavors 156
Fermentation-Derived Flavors 164
Enzymatic Bioconversion 172
References 174

7. Natural Flavoring Materials 176

Alliaceous Flavors 178
Bittering Agents 186
Cocoa and Chocolate 186
Coffee 195
Essential Oils 200
 Contents IX

Fruit Flavors 202

Specific Fruit Products 208
Herbs and Spices 234
Licorice (Liquorice) 338
Mushrooms and Fungi 339
Nuts 342
Resins 347
Vanilla 351
Vegetables 361

8. Plant Materials Used in Flavorings 365

9. Principal Essential Oils Used in Flavorings 381

10. Organic Chemicals Used in Flavorings and

Fragrances 391
Aromatic Chemicals-Functional Groups 392
Synonyms 514
Prefixes 530
Sources 537

11. Flavor Manufacturing Part I Russ Shay 538

Introduction 538
Raw Materials Handling 540
Liquid Flavor Production 560
Dry Mixing and Blending 589
Flavoring Materials 595
References 602

Flavor Manufacturing Partll Flavor

Encapsulation Gary A. Reineccius 605
Spray Drying 605
Extrusion 613
Molecular Inclusion Via Cyclodextrins 617
Coacervation 620
Fat Encapsulation 620
Miscellaneous Processes 622
Conclusions 623
References 623

12. Flavoring Materials Conhi{Juting to Taste 626

Sweetness 626
Acidulants 635
Potentiators and Enhancers 642
Salt 645
Bitterness 64'8
 x Contents

Trigeminal Effects 651

References 652

13. Flavoring Ingredients Classified as GRAS by the Flavor

Extract Manufacturers Association 655

14. Flavor Patents 671

15. The Flavorist 691

Responsibilities 691
Attributes 692
Training Flavorists 694
The Flavor Laboratories 699
Flavoring Components 700
Laboratory Glassware 701
The Role of the Flavorist-Flavor Creation 701
The Role of the Flavorist-Effective Interfaces 706
The Role of the Flavorist-Samples 711
References 712

16. QualityControlintheFlavorlndustry 713

Sensory Analysis 713
Analytical Methods 7I6
References 729

17. Adulteration 731

Introduction 731
Addition of Synthetic Compounds to a Natural
Flavor 732
Adulteration of Essential Oils 739
References 742

18. Statistical Methods MaureenLahiffand]ane V.

Leland 743
Statistics in Flavor-A General Overview 743
Getting Started 744
Estimation and Hypothesis Testing 748
Regression 753
Analysis of Variance 760
Comparing Variances 771
Multivariate Observations 771
Multivariate Analysis of Variance (MANOVA) 772
Discriminant Analysis 773
Correlation Matrix Methods for Multivariate
Observations 776
 Contents xi

Distance Matrix Methods: Cluster Analysis and

Multidimensional Scaling 778
Cannonical Correlation 780
Analysis of Categorical Response Variables 780
Conclusion 785
Bibliography 786

19. FoodColorants 788

The Need for Food Color 788
International Regulations for Colorants 788
U.S. Regulations for Food Colorants 789
Certified Food Colors 790
Natural Colorants 803
References 816

20. Sensory Analysis Marianne H. Gillette 817

Test Objectives 817
Methods 819
Subjects 830
Physical Considerations of Testing 832
Setting Up a Sensory Program 836
References 836

21. The Safety of Flavoring Friedrich

Grundschober 838
Introduction 838
Priority Setting 840
Safety Evaluation of Flavoring Substances 843
FAOIWHO 846
References 849

22. Labeling Regulations Klaus Bauer 852

Labeling Flavoring Materials 853
Labeling GRAS Substances 853
Food Product Labeling 853
Flavor Labeling United States 860

23. International Flavor Legislation Klaus Bauer 876

Definitions 877
Systems of Control 878
Worldwide Review of Flavor Legislation to 1979 879
References 893
European Economic Community Flavor-Related
Activities 896
1. Council Directive of June 22, 1988 897
xii Contents

2. Commission Directive of January 16, 1991 897

3. Commission Directive ofJanuary 16, 1991 898
Council 901

Index 915
Preface

Flavor is unquestionably one of the most extremely secretive one-reluctant to dis-

important attributes of the food we eat. close anything that might be of value to a
Man does not eat simply to live but even competitor. Thus, little information about
more so lives to eat. Take away the pleasure the activities of the flavor industry itself is
offood and life becomes relatively mundane. available to the public.
There now is a substantial body of liter- The goal of the original Source Book of
ature dealing with food flavor. The "golden Flavors, written by Henry Heath, was to
years" of flavor research in the United States bring together in one volume as much of the
were the 1960s and 70s. Numerous academic worldwide data and facts and as many flavor-
and government institutions had strong related subjects (e.g., food colors) as was
flavor programs and money was readily possible. Henry Heath added a wealth of
available for flavor research. In the 1980s personal information on how the industry
and 90s, research funding has become diffi- accomplishes its various activities, which
cult to obtain, particularly in an esthetic had never been published in any other liter-
area such as food flavor. The number of ature. It has been the intent of this author to
research groups focusing on food flavor has update and build upon the original work of
declined in the United States. Fortunately, Henry Heath. Some chapters of this text
the European and Asian counterparts have draw very heavily upon Henry Heath's orig-
not experienced decreased funding for flavor inal text; others reflect changing aspects of
research and, thus, the very strong research the flavor area and have been substantially
centers in food flavor have continued to rewritten. Additional authors were called
prosper and be productive. upon to contribute chapters to the new
Literature focusing on food flavor has Source Book of Flavors-to expand its
been published in numerous trade and sci- coverage (e.g., sensory/instrumental corre-
entific journals as well as a limited number lations and biotechnology) and to update
of books and symposia proceedings. This areas that this author could not (e.g., safety
literature has focused largely on academic and labeling issues).
issues, as most of the published research has The classic work, Food Flavorings, by
been conducted in academic settings. The Merory (1960), has been deleted from this
industry has been, and continues to be, an new Source Book of Flavors. The industry,
xiii
xiv Preface
as well as the materials used in it, has
changed greatly over the 30 years since
Merory originally published his book. While
many of his formulations would yield good
flavorings, the industry has surpassed these
creations and thus they are not included in
this reference book.
Producing a manageable text required a
selection from among the literature. How-
ever, every subject area has been thoroughly
referenced. These references will lead the
interested reader to the most current liter-
ature for any given subject area. This text is
truly a "source" book or "reference" book
for the flavor industry.
Every effort was made to ensure that
the information presented meets the stated
intent. Despite our combined efforts, some
errors or omissions may have occurred. The
author would appreciate comments on how
to improve the text and notice of any errors.
Gary A. Reineccius
Acknowledgments
It would have been truly impossible for this
book to have been written without the con-
tributions of numerous individuals and orga-
nizations. This author did little other than
assemble and present the accomplishments
of so many. Clearly, the efforts of the con-
tributing authors must be singled out for
special appreciation. The literature searches
and general work on the manuscript provided
by Mark Risch (University of Minnesota)
relieved the author of a substantial burden.
Numerous colleagues in the industry re-
sponded to my questions in a responsible,
open, and timely manner and must be
thanked.
The author must again acknowledge
the effort of Henry B. Heath. He cannot
conceive of ever undertaking the task of
writing this book from "scratch," as Henry
did. Henry deserves compliments and
appreciation.
XV
 Contributors

Mr. Klaus Bauer Dr. Maureen Lahiff

Dragoco Inc. University of California
Gordon Drive Berkeley, CA 94720
P.O. Box 261
Totowa, NJ 07511 Dr. Jane V. Leland
Kraft Co.
801 Waukeegan Road
Dr. Marianne H. Gillette Glenview, IL 60025
McCormick and Company
203 Wight A venue
Hunt Valley, MD 21301 Dr. Charles Manley
Takasago Corp.
100 Green Street
Dr. Friedrich Grundschober Teterboro, NJ 07608
IOFI
8 Rue Charles-Humbert Dr. Gary Reineccius
CH-1205 Department of Food Science & Nutrition
Geneva, Switzerland University of Minnesota
1334 Eckles Ave.
Dr. Susan Harlander St. Paul, MN 55108
Department of Food Science & Nutrition
University of Minnesota Dr. Russ Shay
1334 Eckles Ave. RR 77, Box 258B
St. Paul, MN 55108 Hancock Point, ME 04640

xvi
Chapter 1
The Flavor Industry
OVERVIEW
The acceptability of almost everything that
passes the lips, whether it be food, drink,
confectionery, tobacco, medicine or pro-
ducts used for oral hygiene, is dependent to
some extent on its flavor. Flavor in food and
food flavorings are different terms that have
the same end effect. The flavor of a food
is created by aromatic chemicals that are
biosynthesized during normal metabolic
processes in plants and animals, and possi-
bly further modified by cooking or process-
ing. This intrinsic flavor of food represents
the complex impact made by these aromatic
components on the senses of odor and taste.
Food flavorings, on the other hand, are
man-made. They are compounded from
natural and/or synthetic aromatic sub-
stances, which may or may not be found in
nature. The goal is to impart a flavor of
choice, to modify a flavor that is already
present or to mask some undesirable flavor
to increase the acceptability of the end
product.
Factors leading to acceptance or rejection
of what we eat and drink are many and
complex. The ultimate decision depends not
only on odor and taste, but also on sight,
touch and, possibly, hearing. The extent to
which each of these senses is stimulated also
affects the pattern of judgment. This is
almost impossible to predict because no one
sense acts in isolation, but is interdependent
on all the others as well as on the sensibility
of the consumer.
In all products the raw materials used
contribute their own particular chemistry.
In the case of food products this determines
not only the flavor complex, but also such
attributes as color, texture and mouth-feel.
In compounding food flavorings, therefore,
it is necessary to achieve a high level of
compatibility with the intrinsic flavor of the
raw materials used. A knowledge of their
nature and the chemistry of their con-
stituents is required, as these will influence
the ultimate flavor of the end product.
Food has always been the dominant
concern of the human race. The body has a
constant need for energy and water, but the
process of providing these in the form of
food and drink involves far more than the
mere ingestion of calories and liquid. Most
of us derive great pleasure from eating and
drinking, assisted by an inherent ability
to discriminate between pleasant and
unpleasant experiences. We choose to eat
and drink what we most enjoy rather than
just what is good for us, in spite of a modern
emphasis on nutritional needs. When it
1
2 Source Book of Flavors
comes to food and related consumer pro-
ducts, the initial and continuing success of
many products is dependent upon a positive
response to product flavor (Chou 1990).
The science and technology of food
flavorings requires a knowledge of the
chemistry and characteristics, both physical
and sensory, of aromatic substances of both
natural and synthetic origin. Their in-
dividual contribution as flavoring com-
ponents as well as their safety in use must be
established, and a means devised for their
quality control and regulation in the best
interests of the consumer. Technical educa-
tion now provides this basic knowledge and
also the skill necessary to develop, manu-
facture and apply food flavorings to the
ultimate benefit of the consumer, who is still
the final judge of the success or failure of
any given product.
History
Although the food industry is rooted deep in
history, the flavor industry has developed
only over the past 160 years. It sprang from
small beginnings in companies that special-
ized in the processing and marketing of
natural botanicals such as the herbs and
spices, vanilla beans, vegetables, drugs, the
distillation of essential oils and aromatic
essences, the isolation of aromatic chemicals
from these products and drug extraction
(Dorland and Rogers 1977). The primary
products of these companies were phar-
maceuticals and fragrances; the develop-
ment of flavorings came much later. Today,
these same companies have complex oper-
ations offering a whole range of flavorings
as a service to the food, beverage, con-
fectionery and related industries. They also
sell fragrance compounds for a vast array of
applications, including laundry supplies,
household cleaners and polishes, advertising
purposes (e.g., magazine inserts), air
fresheners, toiletries and the cosmetic
industry.
It was not until the latter half of the 19th
century that chemists began to realize the
flavoring possibilities of synthetic aromatic
chemicals (Bedoukian 1967). In 1858,
vanillin was first crystallized from an alco-
holic extract of vanilla beans by Gob ley.
It was 1872 before Carles established its
empirical formula and another two years
before Tiemann and Haarman reported its
structure; later Reimer confirmed it by
synthesizing vanillin from guaiacol. At
about the same time, organic chemists were
preparing a wide range of highly odorous
aromatic chemicals, which were later to
be of great value to the flavor industry.
Solutions of esters for use as artificial fruit
essences were exhibited at a trade fair in
London and shortly after were in use in the
United States. In 1860, the first book of
artificial flavoring formulations was pub-
lished anonymously in Philadelphia. This
was followed in 1916 by a manual for the
essence industry by Walter, in which a
large number of formulations for artificial
flavorings were published. Until the pub-
lication of Food Flavorings: Composition,
Manufacture, and Use (Merory 1968), there
was a complete dearth of information on the
formulation of imitation flavors-hardly
surprising, as most flavor manufacturers
treat this information as a secret essential to
their competitive position and growth.
The flavor industry developed from its
main centers in the United Kingdom and
Europe and soon became firmly established
in the United States (Pisano 1973). From
Europe, essential oils as well as com-
pounded flavors and fragrances were ex-
ported overseas as countries were opened
up commercially. In the early part of the
20th century, many of the larger flavor
houses established their own local manu-
facturing facilities in order to better serve
this growing industry.
Size and Market
In total, the flavor/fragrance industry had
worldwide sales in 1987 estimated at about 7
billion dollars (Unger 1989). As can be seen
in Table 1-1, fragrance and flavor com-
 The Flavor Industry 3

TABLE 1-1. Estimated worldwide merchant sales of flavors and fragrances by large
product categories, 1987-1990 (Unger 1989a). (In$ US millions)

Average Annual
Growth Rate
Product Categories 1987 (Share) 1990/1997 1990 (Share)

Fragrance compounds 2,350 (33.6%) +6.0% 2,800 (32.6%)

Flavor compounds 2,300 (32.8%) +8.5% 2,950 (34.4%)
Aroma chemicals 1,250 (17.9%) +6.5% 1,500 (17.4%)
Essential oils and
other natural
products 1,100 (15.7%) +7.5% 1,350 (15.7%)
World Total 7,000 (100.0%) +7.0% 8,600 (100.0%)
Remarks: The average annual growth rates in current US dollars include quantity growth, price
inflation and foreign exchange rate effects (distortions).

pounds make up the largest share of sales. TABLE 1-2. Flavor compounds: Estimated break-
The flavorings go into a large number of down of worldwide merchant sales
foods. A breakdown of flavor usage into the according to large flavored end-product
segments in 1987 (Unger 1989a)
major products is presented in Table 1-2. As
one might expect, beverages are the largest Millions
single product for flavorings. In the future, Flavored End-Product of US
we may well see this distribution shift. The Segments Dollars Share
beverage market in developed countries is Beverages (alcoholic and
reasonably saturated and thus minimal non-alcoholic) 725 31.5%
growth is anticipated. Changes in food Confectionery, chocolate
preferences for low calorie foods or fat-free and baked goods 460 20.0%
Dairy products, oils and fats 345 15.0%
products are opening up very large market
Culinary products (snacks,
opportunities for flavor companies in new convenience foods,
product areas. Thus one may expect to see processed meat, etc.) 333 14.5%
the market share for flavorings increase in Oral hygiene and
areas such as cheeses, ice creams, and fats pharmaceuticals 184 8.0%
Others (tobacco, pet foods,
and oils. Western Europe, the U.S. and
miscellaneous) 253 11.0%
Japan accounted for over 70 percent of
World Total 2,300 100.0%
worldwide flavor and fragrance sales (Unger

TABLE 1-3. Estimated worldwide merchant sales of flavors and fragrances by large
geographic regions, 1987-1990 (Unger 1989a). (In$ US millions)

Average Annual
Growth Rate
Regions 1987 (Share) 1990/1997 1990 (Share)

Western Europe 2,500 (35.7%) +6.5% 3,050 (35.5%)

United States 1,650 (23.6%) +5.5% 1,950 (22.7%)
Japan 850 (12.1%) +7.5% 1,050 (12.2%)
Rest of the World 2,000 (28.6%) +8.5% 2,550 (29.6%)
World Total 7,000 (100.0%) +7.0% 8,600 (100.0%)
Remarks: Flavors and fragrances include: fragrance compounds, flavor compounds, and aroma
chemicals, as well as essential oils and other natural products.
The average annual growth rates in current US dollars include quantity growth, price inflation
and foreign exchange rate effects (distortions).
4 Source Book of Flavors

1989a, see Table 1-3). These sales are
divided among 13 relatively large companies
accounting for about 62 percent of these
worldwide sales and literally hundreds of
smaller national and international flavor/
fragrance companies that make up the
remainder of the market (see Table 1-4).
While the large flavor /fragrance companies
are basic in natural products and/or syn-
thetic flavor chemicals and produce a
multitude of flavoring and fragrance ma-
terials, the smaller companies tend to serve
a limited area or provide flavorings and
seasonings to a particular branch of the food
industry.
Some of the very big food processors
have established their own flavor com-
pounding departments not only to serve
their immediate needs, but also compete on
the open market. This strategy has not
generally been adopted by the food industry
since the flavor industry much more closely
resembles a chemical company than a food
company. The industry requires very
specialized individuals (e.g., chemists
who know organic synthesis, isolation of

TABLE 1-4. Estimated worldwide merchant sales by the largest international flavor
and fragrance companies in 1986 and 1987 (Unger 1989a). (In $ US
millions and local currencies)

Competitors 1986 1987 %

IFF $ 621 746 +20.1

Quest (PPF & Naarden) $ 515 635 +23.3
Givaudan/FDO $ 543 632 +16.3
SF 740 720 -2.7
Takasago (Ending March) (Billions) $ 329 440 +33.7
YEN 52.5 60.8 +15.8
(86/87) (87/88)
Firmenich (Ending June) $ 294 350 +19.0
SF 470 500 + 6.4
(86/87) (87/88)
Haarmann & Reimer $ 270 321 +18.9
DM 580 577 -0.5
PFW Div of Hercules $ 215 250 +16.3
Bush Boake Allen/Union Camp (together) $ 175 210 +20.0
Hasagawa (Ending September) (Billions) $ 148 192 +29.7
YEN 22.3 25.2 +12.1
(86/87) (87/88)
Dragoco $ 150 186 +24.0
DM 325 335 + 3.1
Florasynth-Lautier $ 150 170 +13.3
Roure $ 106 126 +18.9
SF 190 187 -1.6
Felton Worldwide (Ending September) $ 75 85 +13.3
(86/86) (87/88)
Flavor and Fragrance Industry in Grasse, $ 300 346 +15.3
France (14 companies) FF 2,082 2,079 -0.2
Sub-Total $ 3,891 4,689 +20.5
Others (several hundred small- and middle-
sized national and int'l companies) $ 2,109 2,311 + 9.6
World Total $ 6,000 7,000 +16.7
Note: Data for IFF, Quest. Givaudan. Takasago, Rourc, and Grasse companies arc published
figures. All the others are estimates.
Worldwide merchant sales include essential oils and other natural products, aroma chemicals, and
flavor and fragrance compounds, as well as other specialty chemicals (cosmetic and food additives,
etc.)

chemicals from nature or natural products,
and the proper handling of flammable and
odorous chemicals) and must maintain an
inventory of over 5,000 ingredients (often
having limited shelf life). One must also
consider that developing flavors in-house
requires that the company now has to pay
for this service rather than be served by a
large number of flavor companies.
Research
The bigger flavor companies have extensive
research and development facilities. These
large flavor companies spend a relatively
larger proportion of their sales in support of
research than does the larger food company.
For example, four of the larger flavor/
fragrance companies spent the following
percentages of sales on R&D in 1988:
IFF 5.9% (net sales)
Quest 6.2% (net sales)
Haarmann & Reimer 7.5% (net sales)
Givaudan 8.3% (gross sales)
While the flavor industry is often viewed
as an artisan industry, research has gained
a strong position in this industry (Unger
1989).
RELATIONSHIPS
Relationships With End-User Industries
Flavoring ingredients are certainly the most
numerous single group of intentional food
additives. In addition to being the most
numerous of the food additives, they also
happen to be the most profitable and show
the most growth (ca. 6 percent/yr.) in dollar
volume per year of the food additives
(Boccone 1989). The annual sales of food
additives in the United States in 1988 was
nearly 3.2 billion dollars, of which about
12 percent were flavorings and other sea-
sonings, the remainder being colorants,
noncaloric sweeteners and other nonflavor
additives (Dunphy 1989).
Flavorings play an essential role in the
production of an acceptable range of food
The Flavor Industry 5
products with sufficient variation to allow
for choice and to meet consumer needs.
Their manufacture demands an expertise
having a broad base of knowledge of raw
materials drawn from all over the world,
processing techniques and quality control
within the factory, and an understanding of
the technology and manufacturing processes
of the food, soft drink, bakery, confec-
tionery and several other end-user indus-
tries. In addition, the flavor manufacturers'
products must be able to withstand often
adverse conditions of storage and transport
to the point of sale, as the product when
consumed must have the same flavor as
when it was first processed.
Since the turn of the century, the flavor
industry has grown with, and may even be
regarded as integral to, the food processing
industry, to use this term in its widest sense.
This association has grown very close over
the years and, although transactions are still
of necessity very confidential, the cloak
of absolute secrecy that once existed has
largely been replaced by an established trust
and a mutual respect between supplier and
user of flavoring materials.
Technical Service
The past three decades have seen a dramatic
upsurge in technology within the food and
flavor industries resulting in the teaching
of food technology in universities, the
establishment of university and govern-
ment research teams into the nature and
chemistry of food flavors, and the adoption
of a more open policy for the publication
and transfer of information in this area. The
establishment of professional institutes
(e.g., Institute of Food Technologists) has
also done much to improve communications
between the various branches of the food
industry, their suppliers and government
agencies. The extensive technical literature
over this period reflects these changes and
illustrates a more ready acceptance of
the need to share basic information and
experience, and for a mutual collaboration
in new product development.
6 Source Book of Flavors
Most flavor manufacturers expect the
user industries to seek their expert advice
on the choice and efficacy of particular
flavorings in a given product concept, to
offer direct technical assistance in the
assessment of a new product during its
development, and ultimately to provide
flavorings that will not only attract the con-
sumer and create product loyalty, but will
maintain a consistent flavor in the product
until the time it is consumed. This technical
service is generally accomplished by the
direct association of the technical staffs of
the supplier and user companies, although
the purchasing and marketing functions are
often involved. This calls for a considerable
commitment on the part of the flavor
industry, which must staff and provide the
necessary specialist facilities to reproduce on
a laboratory or pilot plant scale represen-
tative end-products capable of being made
on the factory scale. To be effective, tech-
nical service also calls for a willingness
on the part of the product developer to
collaborate fully in providing the essential
data necessary for the product to be made
realistically. Lack of information as well as
ill-defined or vague requests for customer
technical service are the greatest cause of
wasted technical effort. As a result of an
imprecise mandate, much costly inves-
tigative work generally stands little chance
of success, and neither the supplier nor the
food processor enjoys any commercial
benefit from the often time-consuming
effort.
The food industry tends to look to the
flavor industry and other suppliers to pro-
vide free, unlimited, unconditional technical
service involving not just the selection and
recommendation of suitable flavorings, but
also total new product concept and devel-
opment. The savings to be achieved by this
approach were enthusiastically extolled by
Mattson (1970), who considered the role of
the food developer to be one of evaluation
rather than innovation. However, with
rapidly escalating costs and other infla-
tionary pressures, such service has become
uneconomical to the flavor industry unless it
can be tied to a real prospect of profitable
business depending on the successful out-
come of the project. Thus, only projects
with sufficient commercial potential to
warrant the outlay get this level of service.
In fact, one is finding that the larger flavor
companies are setting financial limits on the
projects and even companies they do busi-
ness with in order to maintain profitability.
This provides opportunities for the smaller
flavor companies to develop and meet the
needs of the small food companies.
Having successfully established the use of
flavoring as a product, the industry must
then ensure continuity of supply at a fair
market value and a high level of quality
assurance, giving all assistance to the user
in maintaining his stock of flavoring in a
perfect condition and in providing such data
as will enable the user to comply with
legislative requirements in the country in
which the end-product is to be sold. This is
all part of the marketing process and is a
service necessary in such a technologically
based industry to maintain a continuing
good business relationship (Stapleton 1974).
Relationships With The Government
Individual members of any industry are at
a disadvantage in dealing directly with
government agencies and officials on other
than day-to-day routine matters. This is
recognized, and in most countries the flavor
industry has formed a trade association to
formulate policies and make concerted
representations to the government or other
bodies on matters affecting the smooth,
efficient and profitable conduct of their
business, acknowledging and supporting
the need for consumer protection but
countering unreasonable legislative moves
to achieve this.
Dealing with government agencies can
be complex, but establishing good rapport
is important to the flavor industry. For-
tunately, most governments realize that the
industry takes a responsible and enlightened
 The Flavor Industry 7

viewpoint, and has specialized knowledge to
contribute to the legislative process. As a
result, they are now aiming for uniformity
in treatment and compromise solutions
acceptable to the flavor manufacturers and
food industry as well as to the consumer.
Without this direct collaboration with
government, the flavor industry could well
find itself isolated and subjected to totally
restrictive regulations threatening its very
survival.
Most flavor manufacturers participate
fully in the activities of their respective trade
association and benefit as a result. The
various bodies that represent the flavor
industry nationally and internationally are
discussed later and are listed in Table 1-5.
Relationships With Consumers
With a few exceptions (e.g., culinary
essences, herbs and spices) the flavor in-
dustry is not directly involved with sales to
consumers, dealing rather with the manu-
facturers of consumer products. In spite of
this, the industry has always assumed a
special concern and responsibility for the
safety of the flavoring products it offers for
incorporation into foods and other con-
sumer goods. Long before the present
plethora of legislation, individual flavor
houses had been conscious of the potential
dangers of many organic chemicals of
possible value as ingredients in flavorings.
In formulating imitation flavorings they
have followed a code of good manufacturing
practice, avoiding the use of any doubtful
ingredients. Acceptance for use in flavorings
is based not only on any toxicological
findings but also on having been charac-
terized as present in natural flavors-mostly
in the essential oils-or having a chemical
structure analogous to other chemicals
found in nature, being coupled with an
empirical acceptance of the safety of certain
functional groups and the known or sus-
pected toxicity of others. Today we find that
a substantial body of information is avail-
able on the toxicity of flavor constituents.
TABLE 1-5. National organizations of the flavor
industry
Country National Organization
Australia Flavour and Fragrance Association
of Australia, Private Bag 938,
North Sydney, NSW 2059
Austria Fachverband der Nahrungs-und
Genussmittelhindustrie
Oesterreichs, Zaunergasse 1-3,
A-1037, Wien
Belgium Groupement des Fabricants,
Importeurs et Melangeurs
d' Aromes, Essences, Extraits
et Produits Aromatiques
(AROMA) Square Marie-Louise
49, 1040, Bruxelles 4
Brazil Associaciio Brasileira das lndustrias
da Alimentoac;;o, Av. Brigadeiro
Faria Lima, 2003-11. andar,
01451, Sao Paulo SP
Associaciio Brasileira das lndustrias
de Oleos Essenciais, Produtos
Quimicos Fraqrancias, Aromas e
Afins Av. Brigadeiro Faria Lima,
1570-7. andar-Conj. 72 01452
Sao Paulo SP
Canada Flavour Manufacturers Association
of Canada, 24 Blackdown
Crescent, Islington, Ontario,
M9B5X6
Colombia Asociaci6n Nacional de Industriales
(ANDI), P.O. Box 4430, Bogota
Denmark Essens Fabrikant Foreningen,
Grabrodretorv 16, DK-1154,
Kopenhagen
France Syndicat National des Industries
Aromatiques Alimentaires, 89
Rue du Faubourg St. Honore
F-75008 Paris
Germany Verband der Deutschen
Essenzenindustrie E.V.,
Meckenheimer Allee 87, D-5300,
Bonn 1
India Perfumes and Flavours Association
of India-PAFAI, 2-B, Court
Chambers, 35, Sir Vithaldas
Thakersey Marg., Bombay 400
020
Italy Federazione Nazionale dell'
Industria Chimica
(FEDERCHIMICA) (Grupppo
Essence Naturali e Sintetiche),
Via Accademia 33, 1-20131,
Milano
Japan Japan Flavor and Fragrance
Manufacturers' Association
(JFFMA) 3F Nomura Bid, 1414
8 Source Book of Flavors
TABLE 1-5. Continued
Country National Organization
Nihombashi-Kidemmacho, Chuo-
ku, Tokyo 103
Mexico Associaci6n Nacional de Fabricantes
de Productos Aromaticos, A.C.,
Jose M. Rico No.55, Mexico 12,
D.F.
Netherlands Vereniging van Geuren
Smaakstoffenfabrikanten-NEA
1411 GP Naarden Postbus 411,
NL 1400 AK Bussum
Norway Norske Aromaprodusenters
Forening Postboks 6656-
Rodelokka, N-Oslo
South Africa The South African Association of
Industrial Flavour and Fragrance
Manufacturers, Private Bag 34,
Auckland Park 2006, Rep. of
South Africa
Spain Associaci6n Espagnola de
Fabricantes de Aromas para
Alimentaci6n (AEFAA), San
Bernardo 23, 2°, 28015 Madrid
Sweden Foreningen Svenska
Aromtillverkare, Storgatan 19,
Box 5501, 114 85 Stockholm
Switzerland Schweizerische Gesellschaft fiir
Chemische Industrie (SGCI),
Nordstrasse 15, CH-8035, Ziirich
United The British Essence Manufacturers'
Kingdom Association (BEMA), 6,
Catherine Street GB-London
WC2B 511
United States Flavor & Extract Manufacturers
of America Association of the United States
(FEMA), 1620 I St., NW, Suite
925, Washington, D.C.
One may consult such sources as Food
Additives Handbook (Lewis 1989) and
Concon's two-volume work Food Toxico-
logy: Part A, Principals and Concepts and
Part B, Contaminants and Additives (1988).
Every year the FAO/WHO Expert Commit-
tee on Food Additives publishes Toxicologi-
cal evaluation of certain food additives and
contaminants (1989) and is an excellent
source for work being done in this field.
Food Additives (Branen et al. 1989) pro-
vides more highly detailed information and
principles to the reader; of the seventeen
chapters, four deal exclusively with safety
issues.
The flavor industry, having an expertise
in the distillation of essential oils, the
extraction of aromatic plant material and
the isolation and synthesis of aromatic
chemicals, has always been in the forefront
of research into natural flavors. Today, it
still plays a significant role in the field of
research, believing that this will ultimately
benefit the consumer.
FLAVORS OF THE FUTURE
The trend in the food industry is toward the
consumption of more processed and con-
venience foods. This calls for a wide spec-
trum of flavoring effects, and the future of
the flavor industry is inextricably bound up
with that of the food, beverage, and other
related consumer industries in trying to
meet these needs.
The major trends in the food industry
particularly significant to the flavor industry
are the extremely rapid growth of the
microwave food market (Whorton and
Reineccius 1990), the increased consumer
preference for reduced calorie or low-fat
foods and a consumer preference for natural
flavors (Anon 1989).
Microwave Flavors
The rapid growth in microwave foods
presents a particular challenge to the flavor
industry since microwave foods do not
develop a characteristic browned flavor
during cooking, and flavor losses from
foods during microwaving are much greater
than those encountered in conventional
baking (Steinke et al. 1989; Reineccius and
Whorton 1990). Thus, even if flavors are
added to microwave foods to make up for a
lack of developed flavor, these flavors are
essentially stripped from the food during
microwave heating. The industry will have
to develop new flavors that make up for
lacking flavor and then find means to retain
these flavors in the microwaved product.

Fat-Free Foods
The second area of particular opportunity or
challenge to the flavor industry is the low-
calorie food market (Anon 1989). Con-
sumers are becoming keenly aware of diet/
health relationships that suggest cutting
down on calories and fat. In fact, consumers
are more concerned with fat in their diet
than calories. If one removes fat from a food
product, the food may not develop a charac-
teris~ic flavor or texture. Fat can play a key
role m the development of browning flavors
(deep fat-fried flavors or meatlike flavors) as
well as fermented flavors (e.g., cheese
flavor). Attempting to produce a deep fat-
fried flavor in a french fry that has no fat, or
a low-fat breading on fish, for example, can
be most frustrating. A timely example of
opportunity is the marketing of a McLean
Delu~e burger by McDonald's. This burger
contams only 9 percent fat in the beef patty.
To make up for a lack of flavor due to the
low fat content, McDonald's has added a
meat flavor to the burger meat patty.
Another aspect of removing the fat from
food is that "normal" flavors do not taste
the same in the fat-free products. Fat serves
as a reservoir for flavor, reducing the vapor
pressure of fat soluble flavor constituents
and thereby reducing odor intensity. Since
flavor compounds differ greatly in fat
solubility, they will be affected differently
by the presence or absence of fat and thus
the flavor will be perceived differently in
fat vs. fat-free foods. The industry has
tremendous opportunities to develop flavors
for foods traditionally requiring no flavors
but which now need to be flavored. The
problem will be to get these flavors to per-
form adequately in the new food.
Natural Flavors
The trend toward natural flavors started
well over 15 years ago. Initially, most
thought that this trend would be short-lived
since there is no logic to it. However, it has
continued and shows signs of growing in
The Flavor Industry 9
strength. Ten to 15 years ago, flavor com-
panies were selling about 75 percent arti-
ficial flavors and only about 25 percent
natural flavors. The market has completely
reversed itself, and this trend is expected to
continue into the future (Anon 1989a).
Factors Affecting the Future
of the Flavor Industry
When considering the future of the flavor
industry, several easily recognized factors
are of prime significance (Kazeniac 1977).
These include:
Demand for "Better" Flavors
Due to increasing publicity and awareness
campaigns, consumers are becoming more
discriminating. Flavors that were once
quite acceptable are now considered to be
"artificial," "synthetic" or "chemical" in
character. There is an increasing demand
for better flavors. The criterion for that is
difficult to define, as it is the consumer who
is the ultimate arbiter, and who frequently
~onsiders himself to be an expert but is yet
mcapable of providing a meaningful de-
scription of his likes and dislikes when it
comes to flavor.
Consumer Preference for "Natural"
Popular demand is for more "natural"
flavors and "all natural" food products
avoiding the use of additives as much as
possible. This is probably an emotional
overreaction to extensive publicity and a
lack of knowledge of the facts. This calls for
a program of education on the nature of
flavorings, particularly with regard to the
assumed safety of all natural foods and
flavors. However, this will take time
and effort, which no one has a particular
interest in expending. Food companies use
"natural" as a marketing gimmick appealing
to a consumer attitude which, in fact, the
food industry has promoted through much
advertising. The food industry will not profit
from educating consumers that artificial
flavors are as safe or perhaps safer than
10 Source Book of Flavors
natural flavors or may even be of better
quality than their natural counterparts, but
will rather profit from their ignorance. The
consumer will pay more for a natural pro-
duct because of the perceived safety or
health benefits.
Thus, the flavor industry is expending
substantial effort to reevaluate natural
flavor sources and prepare extracts, con-
centrates and isolates that can be classified
as "natural." This is an attempt to pro-
vide acceptable alternatives to the many
excellent imitation flavorings currently
available, without which many popular food
products would not be feasible. Substantial
effort is also being expended to convert
"natural" flavor compounds to other more
valuable "natural" compounds. If a natural
flavor chemical is converted to another
flavor chemical through fermentation,
enzymatic action or FDA-approved pro-
cesses of causing a chemical reaction, the
new chemical is "natural" also. Thus, the
"proper" conversion of butyric acid (from
fermentation) and ethanol (by fermen-
tation) to ethyl butyrate gives the flavorist a
valuable new "natural" chemical to use in
flavor creation.
Research into Natural Flavors
A better understanding of biochemical
processes in natural flavor production
during plant growth and of the chemical
reactions that take place when food is
cooked are essential to the future of the
flavor industry. By close collaboration
between researchers and flavorists, assisted
by modern instrumental techniques and
computerized data recovery, our knowledge
of the chemistry of natural flavors is rapidly
advancing. The number of compounds
isolated and identified in natural flavors is
constantly increasing (see Fig. 1-1) and
many more "nature identical" aromatic
chemicals are now available for flavor
reconstruction. By doing this, the ftavorist
can achieve a closer natural flavor profile.
However, problems arise in those countries
such as the U.S. where there is restrictive
6000 No. of compounds
5000
4000
3000
2000
1000
1963 1967 1974 1979 1984 1989
FIGURE 1-1. Number of volatile compounds
reported to occur in foods and beverages. (H. Maarse
1991)
flavor legislation, by way of a positive list of
chemicals permitted in flavorings. This acts
as a deterrent to expensive research, since
there is little chance of recovering the high
costs of the safety studies.
It is well recognized that the flavor of
many natural food materials changes during
maturation, ripening and subsequent pro-
cessing or cooking, and that these changes
derive from precursors, many of which are
odorless and tasteless, only being converted
into recognizable profiles by complex bio-
chemical reactions within the plant or
during processing (Williams et al. 1989).
Use may be made of this knowledge not
only to effect an improvement in the in-
trinsic flavor of raw materials (the hus-
bandry of which may be controlled so as
to produce optimum flavor levels or de-
sired profiles), but also could lead to an
increasing use of flavor precursors directly
in food processing so that the desired flavor
is produced only in the end-product. This
approach simulates nature and opens up an
entirely new range of products for the flavor
industry.
Legislation
Regulatory control of flavorings and food
additives generally is here to stay, and will
almost certainly increase and spread to

those countries where there is now little or
no legislation in this field. This will pose an
even greater responsibility and restraint
upon the industry not only with respect to
the safety in use of flavoring constituents,
but also in ensuring that its products comply
with the appropriate legislation wherever
the products are sold. Presently, this shows
few signs of harmonization or uniformity.
The regulatory classification of flavoring
materials in many countries is still un-
resolved, the choice lying between open,
mixed and positive-list legislation. The
implications of this will be discussed later,
but the adoption of positive lists of "safe"
chemicals for use in foodstuffs is the most
restrictive approach calling for extensive
long-term toxicological testing of existing
and new chemicals before admission to the
list. Increased toxicological data based
on both short- and long-term studies on
different animal species could well lead to
the eventual rejection of many presently
important flavoring materials. Depending
on the severity of the law, flavorists may be
called on to work from a restricted short list
of permitted chemicals, whose safety has
been established beyond doubt. This could
lead to a significant reduction in the present
wealth of flavoring effects available to
the food industry and might even, in the
extreme, result in a limited range of stan-
dard flavor formulations being offered. It is
to be hoped that this state of affairs never
arises.
Analytical techniques are likely to
become more sensitive and specific than
those now in use. As a consequence, many
new flavoring constituents will be identified,
but the chances of these being available
to the flavorist are small unless there is a
considerable liberalization of flavor legis-
lation to permit the judicious use of nature-
identical flavor compounds.
The flavor industry, as a supplier to the
food industry, will have to live with the
increasing load of government regulations
and control, plus more consumer awareness
of product makeup and nutritional value,
The Flavor Industry 11
and more information on labels, as well as
an increasing need for well-established
quality assurance programs to ensure the
safe and correct handling of flavoring
materials.
Advances in Food Technology
Convenience in food products is already a
major concern of the food industry. This is
expected to increase significantly with a
demand for flavoring systems to meet new
processing, packaging (e.g., aseptic pack-
aging and the general use of polymer-based
food packaging), distribution, and storage
parameters as well as final home prepara-
tion (e.g., microwave cooking).
Economic Viability
All the above factors are certain to impose
increased costs on the flavor industry, only
part of which could be recovered by sales.
The increasing emphasis on the need for
expensive research and development,
without which the flavor manufacturer
would be at a disadvantage and too de-
pendent upon others, could favor the
amalgamation of smaller companies and/or
the strengthening of those already having
the necessary laboratory facilities and staff.
The need to comply with ever more complex
legislation could mean that companies will
tend to specialize and aim at large-volume
production of a limited range of specialist
products, and move away from the tradi-
tional manufacture of relatively small
volumes of a wide range of flavorings to suit
all needs.
Shortage of Experienced, Qualified Staff
The need for well-trained flavor chemists,
flavorists and flavor technologists is press-
ing. The inclusion of flavor chemistry and
flavor technology in university teaching
schedules is a necessity for the future of the
industry, which itself will almost certainly
have to engage in more organized training
programs if it is to provide the staff it needs.
12 Source Book of Flavors
ORGANIZATIONS OF THE
FLAVOR INDUSTRY
In most highly industrialized countries, the
corporate members of the flavor industry
have long-established national associations
that are all active to bring about rational-
ization of flavor legislation and in dealing
with government departments and agencies
on such matters as customs, tariffs, labeling,
etc. In most cases, they have an expert
technical committee to oversee research
on the safety of flavoring materials, and
methods for their quality control and assess-
ment. These committees also appraise and
possibly influence government response to
consumer pressures for assured whole-
someness offood, beverages, etc., as well as
for the safety of flavorings and colorants
used in their manufacture.
The need for these associations arose as
governments became more involved with
legislation on food safety which, in turn,
imposed limitations on the activities of
flavoring suppliers. In the United Kingdom,
legislation was enacted as far back as 1860
for "Preventing the Adulteration of Articles
of Food and Drink" (Amos 1960) to be
followed very shortly by similar legislation
in the Commonwealth countries. In the
United States, the Food and Drug Act of
1906 introduced a regulation of materials to
be used in the food and drug industries, and
this law remained in force until 1938 when it
was superseded by the Federal Food Drug
and Cosmetic Act (FD&C). This latter
legislation specifically controlled flavoring
materials. However, the interest of the law-
makers in food flavorings dates from the
early 1950's, when a Committee of the U.S.
House of Representatives investigated the
need for control of chemicals in foodstuffs.
At that time, the Food and Drug Admin-
istration Division of Pharmacology began
acute short-term and chronic studies on a
number of flavoring substances in wide use.
Their deliberations resulted in the 1958
Food Additives Amendment to the 1938
Act. As a consequence, those who wanted
to sell or use new food additives had to
furnish safety data and analytical methods
for their control. It was this requirement
that impressed upon the flavor industry the
urgent need for it to be involved directly
in the legislative process via its national
association. This is still the prime purpose of
the many national associations, details of
which can be obtained by contacting their
respective headquarters (see Table 1-5).
In the English-speaking countries, the
two oldest of these associations are the
Flavor & Extract Manufacturers Associ-
ation of the United States (FEMA) and the
British Essence Manufacturers Association
(BEMA).
Flavor & Extract Manufacturers
Association (FEMA), 1620 I St. NW,
Suite 925, Washington, D.C. 20006
Formed in 1909, the Flavor & Extract
Manufacturers Association of the United
States is the association that represents the
industry in America. Its aims are stated to
be the maintenance of a close surveillance
of any actions, particularly in the field of
legislation, which could affect its corporate
members. It also stimulates and coordinates
work on problems within the industry and
represents the views of its membership in
meetings with government agencies and
parallel national and international bodies,
such as the International Organization
of the Flavour Industry (IOFI) and the
British Industrial Biological Research
Association (BIBRA). These activities
ensure that members are kept fully in-
formed of the legislative process and have a
concerted voice at the appropriate stage of
consultation.
For many years FEMA has had a Food
Additives Committee to oversee legislative
developments and keep the membership
informed and forewarned of any laws that
might restrict their business interests.
Eventually, the Committee became the

main liaison between the industry and the
U.S. Food and Drug Administration. In
1959, it conducted a survey to provide basic
data for a program to determine what flavor
ingredients were in use in the United States
and to establish in what products and at
what levels they were used. In addition,
much information on the safety of these
chemicals was collected and collated. As a
result of these investigations, the FEMA
Committee proposed the first list of flavor-
ing materials that were generally regarded
as safe (GRAS). In 1961, the FEMA GRAS
list covered 1,300 flavoring substances. The
FEMA GRAS list increased to 1,750
compounds as of 1985 (Lewis 1989).
Late in 1960, the FEMA management
committee established a panel of six experts
drawn from the fields of biochemistry,
toxicology, pharmacology, metabolism and
medicine to review these initial lists. In
1965, this Expert Committee was instru-
mental in publishing a revised GRAS list,
which formed the basis for subsequent
argument and review on the safety in use of
flavoring chemicals. The detailed consid-
eration of the Committee's findings and
ongoing progress in getting the lists accepted
will be discussed later, in Chapter 19 on
legislation.
FEMA, in association with IOFI, has
conducted two surveys on the usage of
flavoring material in foods (1973 and 1977)
and more recently in cooperation with the
National Academy of Sciences (Anon
1982), for the Food and Drug Administra-
tion. These surveys have resulted in the
assembly of significant data of value in its
collaboration with government regulatory
agencies and the setting up of standards for
flavoring materials (Grundschober et al.
1975).
The British Essence Manufacturers'
Association (BEMA), 6 Catherine
Street, GB, London WC2B SJJ
After preliminary meetings in 1911, the
British Essence Manufacturers Association
The Flavor Industry 13
was established in 1917. Like its American
counterpart, the Association consists of
those actively engaged in the manufacture
of "essences" which, in this context, in-
cludes food colors and miscellaneous
products used by the food, beverage, con-
fectionery, perfumery, tobacco and similar
trades. The objectives of the Association
are to consider and determine such matters
as affect the trade generally and to promote
the interests of its members.
BEMA has been active in promoting
harmonization of the very diverse legislation
that exists throughout Europe and has
successfully organized itself to parallel
government and official committees of the
Council of Europe in Brussels and IOFI in
Geneva.
Representatives of the Association are
members of IOFI and also sit on the Food
and Drinks Industries Council (FDIC),
which represents all the food and beverage
companies in the United Kingdom via their
own associations, representatives of which
form an equivalent body in the Council of
Europe. This integrated structure enables a
unified, simplified and comprehensive point
of view of the flavor industry and its re-
lated user-industries to be formulated and
presented to the legislators.
International Organization of the Flavour
Industry (IOFI), 8 Rue Charles-Humbert,
CH-1205 Geneve, Switzerland
Cooperation between individual flavor
houses on the national level has existed for a
long time in most European countries as
well as in the United States and Canada.
The active national associations have
already achieved much in promoting the
common interests of the industry, but the
need for a more international coordination
of effort, particularly in the field of inter-
national legislation, was long felt. The
IOFI was established in 1969 as a body to
promote the universal representation of
the flavor industry. The founding member
14 Source Book of Flavors
countries, Austria, Belgium, Germany,
France, Italy, Netherlands, Switzerland,
United Kingdom and United States, were
joined by Japan and, in later years, by
Australia, Brazil, Canada, Colombia, Den-
mark, India, Mexico, Norway, Singapore,
South Africa, Spain and Sweden. The pre-
sent membership numbers 22.
The main activities of IOFI are in such
areas as:
• Collection, analysis and harmonizing of
regulations.
• Elaboration of Codes of Practice and
industry guidelines.
• Collection, generation and evaluation of
safety data.
• Inventories of raw materials and
specifications.
• Methods of analysis.
• Environmental matters.
The results are collected, evaluated and
distributed to members, governmental and
other interested groups. IOFI is collabo-
rating closely with IFRA, the International
Fragrance Association. Both associations
perpetuate the self-regulatory tradition of
the flavor and fragrance industry.
The IOFI Code of Practice includes:
• A complete set of definitions and
terminology.
• A restrictive list of natural and nature-
identical substances.
• A positive list of artificial flavoring
substances that have been reviewed for
safety.
• Lists of flavor adjuncts.
• A list of extraction solvents and their
residues.
• Guidelines for process flavorings.
• Guidelines for health and environmental
protection.
• Guidelines for quality control.
• Guidelines on the interpretation of the
word "natural."
• Guidelines for the preparation of smoke
flavorings.
• Guidelines for other types of flavorings
being developed.
The headquarters of IOFI serves as a
clearing center for questions on flavorings
and their legislation. Member associations
are supplied with regular information letters
and a monthly Documentation Bulletin.
The business of the organization is con-
ducted at sessions of the General Assembly
and is administered by a Board of Directors
on which each of the member countries has
a delegate.
To handle scientific affairs a Committee
of Experts was formed that is fully repre-
sentative of the membership. A working
group on Methods of Analysis develops
analytical methods needed to enforce re-
strictions for certain substances. This group
is also evaluating the reported identifica-
tions of flavoring substances in natural
source materials. In collaboration with
IFRA, a Technical Committee for En-
vironmental Protection and an Intellectual
Property Protection Committee have been
formed. IOFI, IFRA and IFEAT collabo-
rate in the organization of the International
Congress on Flavors, Fragrances and
Essential Oils, held every three years.
The principal, but by no means the only,
function of IOFI is to present a universal
viewpoint on matters of flavor legislation to
various national, regional and international
regulatory bodies. During the past 30 years,
food habits have changed beyond recog-
nition with increasing markets and new
technologies. In many countries, the legis-
lation to protect the consumer has not kept
pace with these advances and is often far
from realistic. The IOFI resolutions carry
considerable weight in the drafting of
regulations governing the use of flavorings.
The combined experience of its membership
provides a basis for a more uniform applica-
tion of the law. IOFI has the status of a
permanent observer at the joint FAO/WHO
Food Standards Commission and partici-
pates fully in sessions of the Codex Alimen-
tarius Commission-all aimed at facilitating

trade between member countries.
Specific activities of IOFI in the classi-
fication of flavoring materials, etc., will be
discussed in a later chapter.
ASSOCIATIONS RELATED TO
THE FLAVOR INDUSTRY
Flavoring and aromatic materials are
universally employed wherever there is an
established food and beverage processing
capability; even in those countries that do
not have these facilities the end-products
must be imported to meet local demand.
This internationality of the flavor industry
means that it must have: (a) a reliable
supply of raw materials of consistent
quality; (b) an ability to sell its products in
all markets to an acceptable standard of
quality in compliance with the law; (c) good
communications with its end-user industries
on the commercial and technical levels; (d)
an opportunity to participate in or discuss
advances in the science and technology of
flavorings in relation to those of its user
industries; and (e) an assurance that the
products it offers are safe and wholesome
for the consumer. These interfaces are
achieved by participation, either directly or
by association, with the following national
and/or international organizations:
a. Standards organizations.
b. Chambers of commerce and trade.
c. National and regional trade organi-
zations.
d. Institutes of science and technology.
e. Professional associations.
f. Research foundations or associations.
To describe all of the above for every
country would be quite beyond the scope of
this work, as each country has its own trade
and technical groupings which are generally
well known. Suffice it to say that those who
work in the flavor industry invariably benefit
by the interchange of ideas and points of
view that occurs during meetings of these
various bodies.
Certain organizations are of international
The Flavor Industry 15
importance and these are worthy of further
comment.
STANDARDIZATION OF FOOD
AND FLAVORING MATERIALS
National Organizations
The food industry and its suppliers have
long recognized the need for standards for
food products and the raw materials used
in their manufacture. Several hundred
standard-making bodies are at work
throughout the world to the point that
international trade is seriously impeded
because of the need to make products to the
specifications of the importing country.
Nowhere is this more complicated than in
the field of food colorants and flavorings.
Today, there is considerable confusion and
no small degree of contradiction between
national standards, although this is now
being reduced to some extent by the setting
up of international bodies such as the
WHO/FAO Food Standards Commission of
the United Nations and the International
Standards Organization. Standards pub-
lished by these two bodies are gaining in
international acceptance and in many
countries form the basis for national speci-
fications. National regulations still display
considerably different provlSlons, par-
ticularly in the acceptability of specific
materials and their declaration on labels;
however, standards of quality are becoming
increasingly more uniform.
Codex Alimentarius Commission, Via Delle
Terme de Caracalla, 1-00100 Rome, Italy
The Codex Alimentarius was conceived at
Geneva in October 1962 at a conference on
food standards convened jointly by the
FAO and the WHO of the United Nations.
A commission was formed in 1963 com-
prising representatives of 67 nations who
work together to define and develop stan-
dards. At subsequent meetings, it was found
necessary to define a procedure for the
elaboration and adoption of standards. The
16 Source Book of Flavors
Commission first decides to deal with a
particular commodity and the appropriate
working committee drafts a standard. This is
circulated to all governments for comments
which, in due course, are reviewed, collated
and referred back to the Commission. This
process is repeated as necessary to obtain
maximum consideration to the final draft
and votes on its acceptance as a Codex
standard. Formal acknowledgment of
governments is then required before the
standard is published in the Codex Alimen-
tarius. The process is necessarily slow but
inevitable in achieving international con-
cord. Right now, governments do not
automatically have to accept a proposed
standard and may merely note the differ-
ence between their own national require-
ments and those of the Codex, or they may
reflect the proposals or even ignore them.
The aim of the Commission is to achieve full
acceptance of the Codex Alimentarius
standards as the basis for any national
standards and so protect consumer health
and at the same time facilitate international
trade. The intention is to publish a list of
those countries accepting the standard
(Procedural Manual of the Codex Alimen-
tarius Commission) and another showing
those whose national requirements are more
strict.
The prime work of the commission
involves the specialist working committees
(26), which are nominated and financed
by participating countries to spread the
workload. The work is tedious and time-
consuming, particularly when standards are
drawn up for compounded food products
containing many materials. At a symposium
held in 1968, many views were expressed
supporting the general aims of the Codex
Commission but casting doubt on its ulti-
mate efficacy (Grange 1968; Stine 1968;
Davies 1968), particularly in those countries
that already have comprehensive standards
for food and raw materials.
International Organization for
Standardization (ISO) 1, Rue de
Varembe, Case Postale 56, CH-1121
Geneva 20, Switzerland
Unlike the Codex Alimentarius Commis-
sion, the International Organization for
Standardization (ISO) is a nontreaty group
comprising representatives of the major
standardizing organizations of the member
countries. It is composed of some 90 national
standards bodies, many of which are gov-
ernment agencies having either participating
or observer status.
The activity of the ISO covers virtually
every field in which standardization can
be applied, but has a strong emphasis on
commodities in which there is international
trade. Presently, there are 165 technical
committees and 2,400 working groups and
subcommittees developing standards. Of
particular interest to the food and flavor
industries are:
TC34 (Agriculture Food Products)-Cover-
ing food and animal feeds with subcom-
mittees dealing with oleaginous seeds and
fats; fruits and vegetables; pulses; milk
and milk products; meat and meat
products; spices and condiments; and
stimulant foods (tea, coffee and cocoa).
TC54 (Essential Oils )-Covering individual
essential oils and methods for their
sampling and analysis.
Until recently, the activity of the ISO
was confined to the more basic aspects of
standardization (terminology, test methods,
etc.) but the current program has been
expanded to include many products that
were previously treated only on a national
level. As with the Codex Alimentarius, the
time taken from initial drafting to final
acceptance is very long. Increasingly, the
ISO is aiming at producing reference stan-
dards so regulatory bodies at any level
should not need to write their own technical
specifications or test methods but merely
refer to the appropriate ISO document.
Overlap of international standards is to
some extent unavoidable, but the ISO now
has formal liaison with a number of inter-

governmental organizations and specialist
agencies. The effect of this collaboration
and wide consultation is that ISO has
changed from an association of national
standards bodies to a more truly inter-
national organization having an activity
stretching beyond the more traditional
scope of its member bodies (Sturen 1977).
National Standards Organizations
A detailed review of national standards
organizations is beyond the scope of this
book. However, the publications of five
such organizations have world-wide recog-
nition and are worth further comment.
Food Chemicals Codex
The enactment of the Food Additives
Amendment to the Food and Drug Act in
1958 required the more specific definition of
food chemicals generally regarded as safe
(GRAS). There was a need for complete
specifications and quality control pro-
cedures, and it was felt that a book of
standards along the lines of the United States
Pharmacopeia (U.S.P.) or the National
Formulary (N.F.) would provide a con-
venient basis for quality assurance.
As a result of requests from many
sources, the Food Protection Committee
of the National Academy of Sciences-
National Research Council undertook to
produce and publish a Food Chemicals
Codex (F.C.C.). The aim of the project was
to define standards for a substantial number
of food grade chemicals, in terms of identity
and purity, based on elements of safety and
good manufacturing practice. An advisory
panel was formed in 1961 to outline the
general policy and to develop guidelines
for the first edition. A Committee of Speci-
fications was subsequently organized to
carry out the detailed drafting work. After
disbanding the advisory panel in 1970, this
Committee now reports directly to the
Committee on Food Additives. Work began
in 1961 on defining those substances that are
added directly to food and amenable to
The Flavor Industry 17
chemical characterization or standardiza-
tion. The selection was from food additives
generally regarded as safe (GRAS), or
those approved by prior sanctions or those
for which special use tolerances had been
established by FDA regulations. The first
edition of the Codex was published in loose-
leaf form between 1963 and 1966. A second
edition appeared in 1976 and the third
edition was published in 1981. It includes
monographs on 776 substances widely used
in food manufacture; however, the number
of substances for which specifications are
provided exceeds 800. Supplements were
produced in 1983 and 1986 to update the
third edition with most current information.
Food Chemicals Codex is published by
National Academy Press (2101 Constitution
Avenue, NW, Washington, D.C.).
American Society for Testing and Materials,
1916 Race Street, Philadelphia, PA 19103
This organization covers the whole field of
standards and its publications are widely
recognized. Of particular interest to the
flavor industry are the reports sponsored by
Committee E-18 on the sensory evaluation
of materials and products, of which the
following are the most important:
S.T.P. 433 Basic principles of sensory
evaluation (1968).
S.T.P. 434 Manual on sensory testing
methods (1968).
S. T.P. 440 Correlation of subjective-
objective methods in the
study of odors and taste
(1968).
S.T.P. 1035 Product testing with con-
sumers for research
guidance (1989).
Fragrance Materials Association
of the U.S., 1620 I St., NW,
Suite 925, Washington, D.C.
Since 1946, the Fragrance Materials Asso-
ciation (formerly Essential Oil Association
of the U.S.A.), through its Scientific
Committee, has compiled and published
18 Source Book of Flavors
monographs on essential oils, aromatic
chemicals and isolates, and related flavor
and perfume materials. In its present loose-
leaf format, the EOA Specifications and
Standards (1975) embodies some 300 such
materials. Each specification has been
drafted by experts in the industry and is
based on available analytical data and
practical experience of these products. The
aim is to provide fair standards for their
evaluation in commercial transactions.
With the advent of modern instrumental
methods of analysis, the expert Instru-
mental Analysis Subcommittee has drawn
up infrared and ultraviolet standards for
some materials and has provided gas
chromatographic charts for others as a guide
to identification.
American Spice Trade Association,
P.O. Box 1267,580 Sylvan Ave.,
Englewood Cliffs, NJ 07632
The American Spice Trade Association
(ASTA) is a body representing the interests
of companies involved in the handling of
herbs and spices, and products made from
them. The need for specifications for this
widely used group of flavoring materials has
long been felt and a limited number are
now published by the ISO and the British
Standards Institute (BSI). The methods for
their analyses are based on the Association's
Official Analytical Methods, a third edition
of which was published in 1985.
Association of Official Analytical
Chemists (AOAC), 2200 Wilson Blvd.,
Suite 400, Arlington, VA 22201
The Association of Official Analytical
Chemists was established in 1884 although
its present name was not adopted until1965.
For the past 60 years it has published every
five years its Official Methods of Analysis,
which is universally recognized as providing
both research and regulatory chemists with
reliable methods for the determination of
the composition and other attributes of
commodities subject to legal control. In the
Preface to the 11th Edition (1970) the
following comment is made in this respect:
"This reliability must be demonstrated by a
published study showing the reproducibility
of the method in the hands of professional
analysts. Adherence to this basic require-
ment has resulted in a compendium of meth-
ods of analysis which has been accorded
preferred status in Federal and State courts,
and which is generally referred to in Federal
and State regulations and governmental and
commercial specifications for food and agri-
cultural commodities. The demonstrated
reliability of AOAC methods has prompted
their use wherever a need for analysis arises
in research or surveillance activities."
AOAC itself maintains no laboratories,
conducts no analyses, performs no tests.
The actual work of devising and testing
methods is done by members of AOAC in
their official and professional capacities as
staff scientists of federal, state, provincial,
and municipal regulatory agencies, ex-
periment stations, colleges and univer-
sities, commercial firms and consulting
laboratories.
AOAC coordinates these scientific stud-
ies, receives and evaluates the results, gives
official sanction to acceptable methods, and
publishes and disseminates the methods.
The reliability of methods of analysis is
more important then ever before. Regula-
tory agencies need reliable, reproducible
and practical methods to enforce laws
and regulations. Industry needs reliable
methods to meet compliance and quality
control requirements. Few organizations in
the world are devoted primarily to testing
and validating analytical methods through
interlaboratory collaborative studies.
Every edition is supplemented by five
annual updates containing new and revised
methods. The 15th Edition contains 1,800
methods; of which 143 are new and 81 are
revised. They include the latest technology
in the field, such as antibody-based test kits,
enzyme immunoassay and near infrared
reflectance spectroscopy.
The AOAC requires thorough testing
and collaborative study of methods before

they are adopted as official and provides the
mechanism by which hundreds of AOAC
members/volunteers obtain or develop,
test, study collaboratively, and validate
analytical methods. The Association pub-
lishes bimonthly The Journal of the AOAC.
Professional Institutes,
Associations and Societies
Following the traditions of medieval Guilds,
almost every profession or trade group has
its own Institute, Association or Society.
Some of these bodies set their own quali-
fication examinations, but most have a
membership determined either by academic
qualifications or by expertise in the par-
ticular discipline within the commercial
context of their activities. The trade group
associations are usually open to anyone with
an interest in its activities.
The flavor industry is well served in this
respect and flavor chemists, whatever their
precise function, are able to participate in
the activities of three types of organization:
(a) societies dealing exclusively with their
special interests (e.g., Society of Flavor
Chemists); (b) institutes within the wider
context of food science and technology
(e.g., Institute of Food Technologists); (c)
specific trade group associations (e.g., Soft
Drink Manufacturers Association).
Although membership is usually re-
stricted to registered companies, flavorists
are encouraged to take an active interest
in the activities of their own industrial
association and those of related industries.
Information may generally be obtained
directly from the association's offices; many
produce a regular news bulletin.
Chemical Sources Association (CSA)
The Chemical Sources Association, located
at 1620 I St., NW, Suite 925, Washington,
D.C. 20006, was established in 1972 to
advance flavor technology and to encourage
the development of new and better flavor-
ings. It provides an essential forum where
The Flavor Industry 19
manufacturers of flavoring materials and
other related raw materials may discuss the
needs of the flavor industry particularly for
hard-to-obtain aromatic chemicals. Not only
does the Association actively assist its
members in obtaining chemicals from
established commercial sources worldwide,
but it encourages key manufacturers to
undertake special production runs to resolve
supply problems. It also encourages an
ongoing program of research and develop-
ment into flavoring substances with the
universities. The CSA's Source List Com-
mittee publishes a listing of flavoring
ingredient suppliers, flavoring raw materials
and their sources.
As part of the overall legislative control
of flavoring materials in the United States,
the CSA works closely with the Flavor
& Extract Manufacturers Association
(FEMA) in the screening of new aromatic
chemicals in respect to their suitability for
use in flavorings.
The effectiveness of this Association is
reflected in the wide membership and active
participation of the flavor industry.
Research Associations
There is a complex area of activity carried
out by government, universities, private
institutions and laboratories. The flavor
industry is not heavily involved in basic
research other than in the field of natural
flavor chemistry, but does have a real
interest in the results of research projects
relating to the future of food and related
commodities as well as in the safety of
flavoring chemicals.
In this latter respect there are a few
associations that have worldwide reputa-
tions for the quality and validity of their
research.
BIBRA Toxicology International
BIBRA (British Industrial Biological
Research Association), located at Wood-
20 Source Book of Flavors
mansterne Road, Carshalton, Surrey, SM5
4DS, Great Britain, is an independent
center for research and advice on chemical
toxicology. It was founded in 1960, jointly
by Government and industry, to provide a
service to the food sector ar.d now serves all
areas of industry in many countries.
The Information Department at BIBRA
offers expertise in the interpretation and
evaluation of toxicity data on chemicals.
It holds a unique collection of specially
selected up-to-date primary research papers,
reports, expert comment and legislative
material. Facilities for online searching
of the major external databases are also
available. The department is able to provide
evaluative summaries of toxicity data, in-
dependent opinion on the safety of materials
in specified end-use applications and advise
on the legislative status of chemicals. The
monthly BIBRA Bulletin reports develop-
ments in chemical regulation and worldwide
toxicological research. The organization
also offers extensive experimental services
on a contract basis to the highest standards
of design and Good Laboratory Practice.
Other Research and Analytical Laboratories
Gale Research annually publishes a Re-
search Centers Directory. In the "Life
Sciences" section, agricultural, food and
veterinary science centers are covered. The
entries describe each center's field or fields
or research and specific subjects for each
center are noted. Directory of Testing
Laboratories is published yearly and com-
piled by ASTM. It lists the locations and
capabilities of testing laboratories that
perform services for a fee. Since listing is
predicated upon an organization's desire to
be included, the work may not be compre-
hensive. Major laboratories and consultants
are listed in the annual Institute of Food
Technologists Directory and Guide. Reports
on their detailed activities can generally
be obtained by writing directly to their
Secretariat. In most countries, there are
government-run or government-sponsored
research laboratories, and details of them
can be obtained by contracting the national
flavor manufacturers association (Table 1-5)
or from the national institute of food science
and/or technology.
INFORMATION SERVICES
Abstracts
The publication of research data, applica-
tion technology, processing techniques,
etc., has now reached such a level that it is
almost impossible for one person to keep
abreast of the advances made in his or her
particular interest or discipline without the
aid of abstracts. The Institute of Food
Technologists (IFT) has always been in
the forefront of information dissemination
and in 1968 organized the International
Food Information Service (IFIS), which
is now sponsored by the Commonwealth
Agriculture Bureaux, England; Gesellschaft
fiir Information und Dokumentation,
Germany; the Institute of Food Techno-
logists, USA; and Centrum voor Land-
bouwpublikaties in Landbouwdocumena-
tatie in The Netherlands. This very active
organization publishes monthly Food
Sciences and Technology Abstracts (FSTA),
which contains approximately 1,700 refer-
ences per issue to literature related to food
research and development, including flavor
topics.
A much broader source of abstracts is
published by the American Chemical
Society. Chemical Abstracts contains
concise, informative statements of the
major disclosures reported in the original
documents. They are findings-oriented and
are not critical or evaluative summaries.
Their purpose is to give accurately and
quickly sufficient detail about the informa-
tion reported in the entire original docu-
ment. The publishers regularly monitor
more than 14,000 periodicals from 150
nations, patent documents from 26 coun-
tries and two international industrial
property organizations, plus reviews, tech-

nical reports, monographs, conference
proceedings, symposia, dissertations and
books. The primary purpose of this work is
to let the reader determine if the entire
original publication need be consulted.
A more manageable abstract is published
by Chemical Abstract Services (Columbus,
Ohio) titled CA Selects: Flavors and Fra-
grances. This service reviews the data bases
of Chemical Abstracts and selects abstracts
relevant to the flavor and fragrance in-
dustry. This abstract service has the entire
resources of Chemical Abstracts. CA Selects
is published every two weeks.
Journals and Trade Magazines
Concerning Flavors
There are numerous journals and trade
magazines that contain information relevant
to the flavor industry. Some of those listed
(e.g., Perfumer and Flavorist and Flavor
and Fragrance Journal) are devoted nearly
entirely to information related to the in-
dustry. Other offerings will contain occa-
sional articles or sections devoted to food
flavorings. The following list covers most
publications in the United States and
England.
Chemical Marketing Reporter-Schnell
Publishing Company, 80 Broad St., New
York, NY 10004.
Food Chemical News-1101 Pennsylvania
Ave., S.E., Washington, D.C. 20003.
Chilton's Food Engineering-Chilton Way,
Box 2035, Radnor PA 19089.
Food Flavourings, Ingredients and Pro-
cessing (formerly International Flavours
and Food Additives and The Flavour
Industry) United Trade Press Ltd.-
U.T.P. House, 33/35 Bowling Green
Lane, London, ECIR ODA.
Food Technology-IFf, 221 N. LaSalle St.,
Chicago, IL 60601.
IFIS Food Science and Technology Ab-
stracts-International Food Information
Service. Subscriptions obtained in U.S.
through Institute of Food Technologists.
The Flavor Industry 21
Journal of Agricultural and Food Chem-
istry- American Chemical Society, 1155
16th St., NW, Washington, D.C. 20036.
Journal of the Association of Official An-
alytical Chemists- The Assoc. Off. Anal.
Chemists, Inc., Box 540, Benjamin
Franklin Station, Washington, D.C.
Journal of Food Science-Institute of Food
Technologists; Suite 2120, 221 N. LaSalle
St., Chicago, IL 60601.
Journal of the Science of Food and Agri-
culture-Society of Chemical Industry.
Elsevier Science Publishing, Ltd., Crown
House, Linton Rd., Barking, Essex 1G11
8JU, England.
Perfumer and Flavorist-Allured Publish-
ing, Bldg. C., Ste. 1600, 2100 Manchester
Rd., Box 318, Wheaton, IL 60189.
Riechstoffe-Aromen-Korperpflegemittle-
Gerhard R. Barsch (ed.), 3 Hannover-
Kirchrode, Postfach 149, Ostfeldsrasse 61.
Commercial Flavor Manufacturer Publica-
tions-Distribution Limited, Dragoco
Report-Gordon Dr., P.O. Box 261,
Totowa, NJ 07511. Quest News, U.S.
Edition-10 Painters Mill Road, Owings
Mills, MD 21117.
Flavor and Fragrance Journal-John Wiley
& Sons, Baffins Lane, Chichester,
Sussex, P0191UD, England.
Cereal Foods World-American Associ-
ation of Cereal Chemists, 3340 Pilot
Knob Rd., St. Paul, MN 55121.
Associations and Societies
American Chemical Society
1155 16th Street, NW
Washington, D.C. 20036
American Pharmaceutical Association
2215 Constitution Ave., NW
Washington, D.C.
The American Society of Perfumers, Inc.
P.O. Box 1551
West Caldwell, NY 07006
Drug, Chemical and Allied Trades Asso-
ciation, Inc.
Two Roosevelt Ave.
Syosset, NY 11791
22 Source Book of Flavors

Fragrance Materials Association Concon, J.M. 1988. Food Toxicology Part A:

1620 I Street NW Principles and Concepts. New York: Marcel
Washington, D.C. Dekker, Inc.
Food and Drug Administration Concon, J.M. 1988. Food Toxicology Part B:
5600 Fishers Lane Contaminants and Additives. New York:
Marcel Dekker, Inc.
Rockville, MD 20857
Davies, J.H.V. 1968. The Codex Alimentarius.
Center for Food Safety & Applied Nutrition Food Technol. 22(9):68- 70.
200 C. St., SW Dorland, W.E. and Rogers, Jr., J.A. 1977. The
Washington, D.C. Fragrance and Flavor Industry. Mendham:
Center for Drug Evaluation and Research Wayne E. Dorland Company.
North Metro Park Dresser, P.D. 1989. Research Centers Directory.
Rockville, MD 20857 Detroit: Gale Research Inc.
Institute of Food Technologists Dunphy, J. 1989. Food additives cater to new
221 North LaSalle St. times. Chern. Mark. Report. June 26:3-5.
Chicago, IL 60601 FAO/WHO Expert Committee. 1989. Toxico-
National Association of Fruits, Flavors and logical evaluation of certain food additives
and contaminants. Cambridge: Cambridge
Syrups, Inc.
University Press.
P.O. Box 776 Grange, G.R. 1968. United States interest in
177 Main St. Codex Alimentarius-a government view.
Matawan, NJ 07747 Food Technol. 22(9):70.
The Society of Flavor Chemists, Inc Grundschober, F., Hall, R.L., Stofberg, J., and
C/0 Denise McCafferty Vodoz, C.-A. 1975. Survey of world-wide use
McCormick and Company levels of artificial flavouring substances. Int.
204 Wright Ave. Flavours Food Additives. 6(4):223-30.
Hunt Valley, MD 21031 Kazeniac, S.J. 1977. Flavor trends in new foods.
Synthetic Organic Chemical Manufacturers Food Technol. 31(1):26-8, 32, 33.
Association Lewis, Sr., R.J. 1989. Food Additives Hand-
book. New York: Van Nostrand Reinhold.
1330 Connecticut Ave., NW
Maarse, H. and Boelens, M.H. 1990. The TNO
Suite 300 data base "volatile compounds in food": past,
Washington, D.C. 20036 present and future. In Flavor Science and
Technology, eds. Y. Bessiere and A.F.
References Thomas, pp. 275-8. Chichester: John Wiley
Amos, A.J. 1960. Pure Food and Pure Food & Sons.
Legislation. Butterworth & Co. Ltd., London. Maarse, H. 1991. Volatile Compounds in Foods
Anon. 1989. Flavor growth sparked by changing and Beverages, pp. 1-39. New York: Marcel
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Merger Frenzy. Chern. Mark. Rept. Nov. 4(3):106-8, 118.
27:5, 23. Merory, J. 1968. Food Flavorings: Composition,
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Stofberg, J. and Stoffelsma J. 1981. Consump-
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Stofberg, J. 1983. Consumption Ratio and Food
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Stofberg, J. 1983. Safety Evaluation and Regu-
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Gallagher, J. 1989. Interaction of flavor
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The Flavor Industry 23
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Chapter 2
Flavor Analysis
Flavor is a very complex sensation com-
posed primarily of aroma and taste, but also
complemented by tactile and temperature
responses. Taste is limited to the tongue's
responses to salty, sweet, sour and bitter
sensations. The tongue surface also reacts to
the tactile and temperature stimuli, which
include the cooling of menthol and the heat
of red pepper. There is a tactile response to
texture, astringency, etc.-all of which
contribute to the overall flavor perception.
However, the most important characteristic
of flavor is aroma. The importance of odor
to flavor perception becomes very obvious
when a person catches a cold and can only
sense flavor characteristics by the taste,
tactile and temperature responses.
Ordinarily the human can discriminate
among several thousand odors. Because
of the importance of aroma to flavor per-
ception, the vast majority of analytical
flavor studies have focused on the volatile
constituents, or the odor, of foods. The task
of identifying volatile flavor components in
natural products is formidable for several
reasons:
1. The initial reason is that laboratory
instrumentation is not as sensitive to many
odors as is the human olfactory system.
24
Stuiver (1958) calculated that as few as 8
molecules of a potent odorant can trigger
one olfactory neuron and that only 40
molecules may provide an identifiable
sensation. Making a few assumptions about
air concentration versus absorption on the
olfactory membrane, it is postulated that the
nose has a theoretical odor detection limit of
about 10- 19 moles, which rivals or surpasses
even the most sensitive analytical abilities.
2. A second complication is that food
flavor is distributed throughout a food
matrix. Isolation of only the volatile portion
of the food is made difficult by the ex-
ceedingly low concentrations of flavor
compounds and the presence of sugars,
carbohydrates, lipids, proteins and water as
major constituents. The low concentration
of flavors in food products necessitates the
isolation of the volatile fraction so it may be
concentrated for analytical work, and this
isolation may be hindered by binding of
flavor by food proteins. Proteins are also
great emulsifiers, which complicates simple
flavor extraction process using organic
solvents. The presence of lipids lowers
flavor compound vapor pressure and the
lipids are extracted by organic solvents.
3. Flavor isolation and analysis are made
difficult also by the fact that flavors com-

prise a large number of chemical classes.
The flavor chemist cannot focus only on one
functional group, and thus greatly simplify
the procedure. Rather, the chemist must
attempt to effectively extract and concen-
trate alcohols, aldehydes, acids, ketones,
amines, heterocyclics, aromatics, gases,
nonvolatiles (or nearly so), etc.
4. The absolute number of flavor com-
pounds in a food further complicates flavor
analysis. It is a rather simple, natural flavor
that has less than 200 identified constituents.
In fact, those with fewer than 200 identified
constituents probably have not been ade-
quately researched. It is not uncommon for
the browning flavors (e.g., of meats) to be
comprised of more than 1,000 identified
constituents. Research has only started to
scratch the surface in identifying volatile
flavor constituents. In 1989, nearly 6,000
different flavor compounds had been iden-
tified in foods (Maarse and Visscher, 1989).
Rijkens and Boelens (1975) estimated that
probably 10,000 actually exist.
5. Once the flavor of a food has been
extracted, concentrated, separated and
detected, a major question arises con-
cerning each chemical's importance to the
flavor. Unfortunately, analytical instru-
mentation has no sense of taste or smell.
Instrument response for the flame ionization
detector (used in gas chromatography) is
related to the number of carbon-carbon
bonds, whereas the human olfactory system
varies greatly in response to different odors.
For example, 2-methoxy-3-hexyl pyrazine
has an odor threshold of 1 part/10 12 parts
water, while pyrazine has an odor threshold
of 175,000 parts/10 12 parts water (Seifert
et al. 1970). On pyrazines alone, the human
threshold varies by nearly 2 x 108 . It could
be that the smallest peak in a gas chromato-
graphic run may be more important to flavor
than the largest peak. It must also be re-
cognized that the instrument provides no
appreciation for the flavor character of each
component. It is not apparent, for example,
that peak 3 is buttery, while peak 48 con-
tributes oxidized flavor notes.
Flavor Analysis 25
6. A final problem complicating the
study of flavor is instability. The food pro-
duct being examined is a dynamic system,
readily undergoing flavor changes while
being stored awaiting analysis to begin. The
flavor isolation step may initiate chemical
reactions (e.g., thermally induced degrada-
tion or oxidations), which alter the flavor
profile. The final analysis via gas chromato-
graphy may produce isomerizations in the
gas chromatograph itself.
There is no question that flavor analysis
offers a most challenging analytical prob-
lem. After the presentation of the methods
for isolation and analysis of flavor in foods,
it will be easy to see that each method has
its own unique shortcomings. No single
method will provide a flavor profile truly
representative of the food. This chapter
addresses how the analytical chemist uses
the most commonly practiced methods for
flavor analysis. The interested reader can
refer to more detailed discussions of this sub-
ject by Werkhoff et al. (series of 12 articles,
1989-1990), Widmer (1990), Reineccius
(1989), Parliment (1986), Reineccius and
Anandaraman (1984) and Schreier (1984a,
b).
SAMPLE PREPARATION
The first step is to select samples of the food
most typical of the flavor or off-flavor to be
studied. If one is studying an off-flavor
problem, the strongest yet characteristically
flavored samples need be selected. Re-
calling the extreme sensitivity of the human
olfactory system demands that the most
intense samples be selected in order to
improve the probability that relatively
insensitive machines can pick out the
volatiles of interest.
One cannot simply put an apple or a pie
into an instrument and expect a response (at
least a desirable response!), but one must
somehow extract the flavor from the food
and concentrate the flavor isolate. This gen-
erally requires that the food be crushed,
26 Source Book of Flavors
homogenized, blended or extracted in some
manner (Sugisawa 1984). Most fresh plant
and animal tissues contain active enzyme
systems that may quickly alter the flavor
profile once cellular disruption has occurred
(Drawert et al. 1965; Fleming et al. 1968;
Josephson et al. 1984; Kazeniak and Hall
1980; Dirinck et al. 1981; Nitz et al. 1988).
Singleton et al. (1975) demonstrated how
sample handling during flavor isolation may
influence the flavor profile of peanuts. Pea-
nuts ground in water following immersion in
liquid N2 showed a 62 percent decrease in
pentane and an 87 percent decrease in total
carbonyls compared to dry grinding at room
temperature. Peanuts ground in liquid N2
showed an 81 percent decrease in pentane
and an increase in total carbonyls compared
to dry grinding at room temperature. Blend-
ing time, temperature and pH all were shown
to have a pronounced effect upon the flavor
profile of peanuts.
The inactivation of enzymes of fresh
plant and animal tissue when the isolation
procedure exceeds only a few minutes is
essential. A common method is to homo-
genize the food in methanol (Drawert et al.
1969; Schreier et al. 1976). This does,
however, dilute the sample, decrease the
polarity of an aqueous food slurry, and
may interfere with later isolation methods.
Thermal processes may also be employed if
the product is a juice and may be rapidly
passed through a high temperature short-
time heat exchanger. One must be aware of
the artifacts or interferences contributed by
the means of enzyme inactivation.
Long isolation procedures may even
permit fermentation to occur. Ribereau-
Gayon et al. (1975) added sodium fluoride
to crushed grapes to inhibit microbial
growth.
In addition to enzyme or microbially
induced changes in flavor profile during the
isolation procedure, one must also be aware
of chemical changes. Long isolation times
may permit oxidative changes to occur.
Thought must be given to doing a procedure
under C02 or N2 . Some researchers have
chosen to add antioxidants such as BHA,
BHT or ascorbic acid (Ribereau-Gayon et
al. 1975). High temperatures (greater than
60°C) for extended periods can promote
nonenzymatic browning reactions. Reduced
temperatures (e.g., with vacuum distilla-
tions) should be used whenever possible.
ISOLATION OF FOOD FLAVORS
Headspace Methods
Direct Injection
Direct analysis of the headspace vapors
above a food product seems to be the ideal
method of flavor isolation. This method is
simple (i.e., draw 10 ml of headspace into a
syringe and inject it into a gas chromato-
graph), rapid, reproducible, and samples
only what the nose receives (Macku et al.
1988). The primary problem with direct
headspace analysis is that too little sample is
available for instrumental analysis. Note in
Fig. 2-1 that only the most volatile esters are
detected by the conventional split head-
space analysis. Since direct headspace in-
jections are generally limited to 10ml or
less, only those volatiles present in the
headspace at concentrations exceeding
10-7 g/L (headspace) will be detected by
gas chromatography (GC) and only those
exceeding w-s g/L (headspace) will be
adequate for mass spectrometry (MS)
(Schaefer 1981). Since the concentration of
volatiles above a food product ranges from
about 10- 11 to 10- 4 g/L (Weurman 1974),
only the most abundant volatiles above a
food may be analyzed using direct head-
space sampling. While the use of splitless
or on-column headspace techniques sub-
stantially improves the sensitivity of the
headspace methods, the technique is still
not adequate for the analysis of trace
volatiles in foods (Leahy and Reineccius
1984). Additional problems with direct
sampling include condensation of volatiles
inside the sampling syringe, absorption of
volatiles in the septum of the sampling jar,
 Flavor Analysis 27

irreproducibility of injection sizes (e.g., dehydrated potatoes. If trace analysis is not

syringe leaks and vacuum in the sample
bottle), GC column deterioration due to
oxygen introduced with the sample and,
finally, relating headspace volatile concen-
tration to actual concentration in the food
itself (Gregoire 1985; Macku et al. 1988).
Despite the many problems and limi-
tations of direct headspace sampling, it
has found substantial application in flavor
studies. Some applications of headspace
sampling as a means of flavor isolation may
be found in the work of Macku et al. (1988)
on bananas; Williams et al. (1972) on
dimethyl sulfide in processed foods; Seo and
Jeol (1980) on a study of lipid oxidation; and
Sullivan et al. (1974) on the flavor quality of
necessary, direct headspace injection may
be the method of choice.
Headspace Concentration
Trace analysis of food volatiles may be
accomplished via headspace concentration
techniques. The equilibrium headspace
vapors above a food or the food itself may
be purged with an inert gas in order to
obtain a large volume of headspace gas for
analysis. The apparatus used for purging the
food sample is most commonly a simple
flask with a means to deliver inert gas so that
the gas sweeps the headspace into a trap
(Fig. 2-2) or bubbles through the sample
and then into a trap. This system is not

PURGE AND TRAP

FREON REFWX

......
0
.....
•
0 0

..
u

..•
a:
a:

"' REDUCED PRESSURE SDE

"
.
.~"
0
u

..
:.,

"
I I.
FIGURE 2-1. Comparison of different methods for the recovery of volatile flavor
compounds from dilute aqueous solutions (ethanol, propanol, butanol, octane,
decane, ethylproprionate, ethyl butyrate, ethyl valerate, 2-heptanone, acetophenone,
benzyl acetate, methyl salicylate, carvone, ~-ionone, methyl anthranilate, ethyl
methyl phenyl glycidate, and isoengenol). (Leahy and Reineccius 1984)
28 Source Book of Flavors

SPLIT HEAI>SPACE SPLITLESS HEAOSPACE OH· COLUWH HEAOSPACE

.•
u u
"' "'

BATCH EXTRACTION
Ole-.met.....
Ole-
CONTINUOUS EXTRACTION

... ...
."
~

."
~

> >
0 0

"' ..
"'

FIGURE 2-l. Continued

employs a counter current flow of purge gas

a and sample with low volumes and high
surface areas so that the purge gas is more
nearly at equilibrium with the sample. This
results in substantially improved recovery of
sample volatiles in reduced analysis time.
The most common methods of isolating
5
and concentrating volatiles from this purged
headspace gas include the use of cryogenic,
6
adsorption or on-column vapor traps.

FIGURE 2-2. Flask Headspace Sampler. (1-Purge
gas inlet, 2-Flow controller, 3-Charcoal filter, 4-Trap,
and 5-Thermostated bath.) (Courtesy of J. Rektorik,
Geneva, Switzerland)
particularly efficient since the purge gas
does not come to equilibrium with the food
sample. Rivier et al. (1990) have designed a
more efficient device (Fig. 2-3). This device
a. Cryogenic trapping
The simplest means of concentrating head-
space vapors is by passing the headspace or
purge gas through a series of cold traps.
Assuming proper design and operation
of the traps, organic volatiles will be con-
densed from the purge gas. A major prob-
lem with cryogenic trapping is that water is
the most abundant volatile in most foods
and, therefore, the trap condensate is
primarily water. Also, an additional step is
 Flavor Analysis 29

A. notarneter F. l herrnostatted s.1mplc II ."~

O. Falling f•h\ double jacketed gl ass tube G. MaQnclic stirrer
C. Trapp;.,g cartridge II . Gc 3r mclcr i•IQ numn
0 . Gas ·IO)uod se parato r J . ClcaniiiQ solut ion
E. Sample coleclo< ~<.Was t e

-
I tot
out
wa h~•

,;:
0.:•
- in

-out
I tot w3h:.••
..· D
-~
-·n
---:-- ) -- - - - '

-
rALLING r iLM Ar>PIIRATUS FOR HEIIOSPACE SAMPLING

II . Gene• al sell(' me B. Oeta•ls

45 rnrn ~~~S
tr•pprng gas

.JLhi=-
OUT - . r Sample
Heatmg wilterl l 1r~
.__•t=-1- Falling ftllll

400 mm

/ Trapp:nq

-·"~J.r c.. ,t rrc.h)C'

.~-- Sarnpl~ vol:tt•fv<;
_.~tttnp1._·
out
. -1---
FIGURE 2-3. The falling film sampler. (Rivier, Spadone, and Liardon 1990)

generally then necessary to extract the
flavor constituents from the water.
A typical headspace cryogenic trap sys-
tem is shown in Fig. 2-4 (Chang et al. 1977).
The sample chamber of this system has a
volume of 18.5 L and will hold 27 .Sibs. of
french fries. Inert gas flows into the bottom
of the sample chamber, through the food
sample and then out into the series of
condensers. The initial condenser is gen-
erally cooled with ice water while the other
condensers may be cooled with dry ice-
30 Source Book of Flavors
FIGURE 2-4. Apparatus for the isolation of trace
volatile constituents in headspace gas of foods. (Chang
et al1977, Copyright 1977, American Chemical
Society)
acetone or liquid N2 . The condensates are
typically pooled and then extracted with
diethyl ether, dichloromethane, or some
other organic solvent. The solvent extract is
dried with anhydrous magnesium sulfate or
sodium sulfate and then concentrated for
GC analysis. The concentration step is often
accomplished by gently warming the extract
under a stream of N2 and permitting the
solvent to evaporate. However, more
sophisticated concentration techniques
(e.g., Kuderna-Danish or spinning band
distillation) may also be used.
While headspace analysis using cryogenic
trapping meets the objective of sampling a
large headspace volume, it does require 2- 4
hours of analysis time and subsequent
solvent extraction of the aqueous distillate.
The long sampling time increases the
opportunity for sample changes during
flavor isolation. The need for solvent ex-
traction adds concerns for solvent impurities
(artifacts), efficiency of extraction (uni-
formity) and flavor losses during solvent
concentration.
Badings and Jong (1984) proposed a
simpler method for cryotrapping headspace
volatiles. They designed an inlet system for
the GC, which included a pretrap at -10°C
to eliminate the majority of water from the
purge gas followed by a second trap that was
lOcm long (1 mm, i.d.) and was cooled
to -130°C. This second trap effectively
collected the flavor components during
purging and then could be heated quickly to
desorb the volatiles into the GC for analysis.
This system permitted short purge times
(20 min.) and yet provided adequate
material for analysis. Badings et al. (1985)
have further refined this technique for
concentrating headspace volatiles and it is
now available commercially (Chrompack,
Middleburg, The Netherlands).
b. Adsorbent trapping
Volatile flavors are often trapped on adsor-
bent materials to avoid co-condensation of
water with the flavor volatiles. The trapping
of volatile flavors on an adsorbent that has
minimal affinity for water eliminates the
need for solvent extraction and associated
problems.
Activated carbon is one of the earlier
adsorbents used for the trapping of flavors
from headspace vapors (Tang and Jennings
1967; Jennings and Nursten 1967). Ac-
tivated carbon will strongly adsorb nonpolar
substances yet only weakly adsorb water
vapor. Therefore, as headspace vapors are
passed over the active carbon, the organic
flavor volatiles are preferentially adsorbed
while water vapor passes through. Carbon
will adsorb an amount of organics approxi-
mately equal to its weight (Schaefer 1981).
However, once the carbon trap (1 - 10 mg
carbon) becomes saturated (10-100 L of
headspace), compounds of greater affinity
will displace the more weakly adsorbed
compounds. Therefore, overloading of the
adsorbent will result in atypical GC profiles.
Adsorbed flavor compounds may be de-
sorbed from the charcoal by either thermal
desorption (Paillard 1965) or solvent ex-
traction (Grab 1973; Jennings and Nursten
1967).
A major advantage of carbon over

TABLE 2-1. Absorbents used for trapping of organic volatiles from vapor phasea
Surface Area Absorbent Capacityb
Absorbent Structure
Charcoal Coconut carbon
Porapak Q Ethyl vinyl benzene-divinyl benzene
Tenax GC Diphenyl-phenylene oxide
XAD-4 Styrene divinyl
XAD-7 Acrylic ester
XAD-9 Sulfoxide
• From Sydor and Pietryzk (1978).
b Percentage of weight of adsorbent.
c NA, not available.
d NR, not retained.
the adsorbents to be discussed shortly is
carbon's very large adsorption capacity (see
Table 2-1), which far exceeds that of the
synthetic polymers. However, concerns
have appeared in the literature for artifact
formation on carbon traps (Baigrie et al.
1985). Apparently, the use of impure
carbon may cause artifacts to form during
thermal desorption of the trapped volatiles
(Palamand et al. 1968). Despite Grob's
(1973) work showing that carbon can be an
excellent trapping material if the carbon is
desorbed by solvent extraction (CS 2 ), a
high-quality carbon is used (coconut char-
coal) and a suitable adsorbate-to-adsorbent
ratio maintained <1:10,000), there were
very few applications of charcoal-based
traps (Roeraade and Enzell, 1972) until the
recent development of microwave desorp-
tion systems. The use of microwave heating
permits very rapid heating of the charcoal
trap and therefore desorption of trapped
volatiles. The desorption is sufficiently rapid
that excellent capillary chromatography can
be accomplished without cryofocusing the
desorbed volatiles. This simplifies the GC
inlet system and provides exceptional
reproducibility (Liardon and Spadone
1986). Recent applications have included
the work of Toulemonde and Beauverd
(1985), Klein et al. (1990) and Reineccius
and Liardon (1985).
The use of synthetic porous polymers for
the trapping of volatiles from headspace
vapors has become the most commonly used
Flavor Analysis 31
(m2g) Ethanol Benzene
1150-1250 7.9 24.7
550-650 0.18 NAC
18.6 NRd 0.53
849 0.40 2.9
445 0.90 1.8
70 0.70 0.82
adsorbent for this purpose. While many
different polymers have been evaluated,
Tenax GC has become the adsorbent of
choice. While this choice is not obvious
from the data in Table 2-1, Tenax GC does
permit superior recovery of adsorbed
volatiles and exhibits relatively good
thermal stability in comparison to the other
synthetic polymers. These two advantages
outweigh the poor adsorption capacity dis-
played by Tenax GC. Withycombe et al.
(1978) compared Chromosorb 105, Porapak
Q, and Tenax GC for the recovery of head-
space volatiles over hydrolyzed vegetable
protein. They found Tenax GC to give the
most characteristic flavor isolate by aroma
judgment.
The limited adsorption capacity of Tenax
is quite evident from the work of Buckholz
et al. (1980) on peanut aroma. They used
three traps in series to evaluate "break-
through" losses of peanut volatiles. The
highly volatile components in peanut head-
space vapors broke through the first two
traps after only 15 min. of purging at 40 mll
min. Jennings and Filsoof (1977) have also
done work on the effectiveness of porous
polymers for headspace trapping. They
found poor retention of ethanol, pentanol,
hexanol and heptane on both Tenax and
Porapak traps. The data presented in
Fig. 2-1 (purge and trap data) also show
poor recovery of the alcohols and higher
boilers. The higher boilers show poor
recovery due to low volatility rather than
32 Source Book of Flavors
"breakthrough" as observed for the
alcohols.
Vercellotti et al. (1988) have modified
this approach to include stripping the
volatiles from foods under a vacuum (8 psi
at 30 to 60°C). The use of a vacuum permits
better recovery of volatiles while using
lower product temperatures. This can
benefit by reducing analysis time and
minimizing artifact formation.
While one can see that there are prob-
lems with applying headspace adsorp-
tion techniques to flavor analysis, the
method has become quite popular in the
literature (Bessiere and Thomas, 1990;
Charalambous, 1990; and Martens et al.
1987). The work of Simon et al. (1980);
Ruen et al. (1982); Liardon et al. (1984);
Olafsdottir et al. (1985) and Noble et al.
(1979, 1980) has shown adsorption head-
space methods to be exceptionally sensitive,
reproducible and accurate. This method is
commonly the one of choice for quantitative
flavor studies.
Isolation of Flavors by Distillation Methods
Distillation methods take advantage of the
volatility of flavor components and non-
volatility of the major food constituents.
Aroma components, by definition, must be
volatile to make a contribution to odor. It is
not unexpected then that distillation is one
of the oldest methods for flavor isolation
from foods.
Distillation is a rather broad term that
includes techniques such as steam distil-
lation and high-vacuum stripping of oils.
Steam distillation typically involves a source
of steam, the sample vessel and a series of
cold traps. Steam enters the sample vessel
so that the food sample is continuously
agitated. Volatile components steam distill
from the food and are condensed in the cold
traps. The initial trap is generally cooled
with ice water, secondary traps cooled with
dry ice/acetone and the final traps with
liquid N2 • The distillate is a very dilute
solution of volatile flavors and water. The
flavor must then be isolated from aqueous
solution. This is generally done by ex-
tracting the distillate with an organic solvent
(e.g., pentane, diethyl ether, or dichloro-
methane). The organic solvent containing
the flavor isolate is dried via the addition of
anhydrous MgS0 4 (or other drying agents),
filtered and concentrated for instrumental
analysis.
A simpler method of isolating flavors via
distillation is to use a simultaneous distil-
lation/extraction (SDE) method. While
there have been several modifications to the
initial distillation head designed by Likens
and Nickerson (1964), the basic idea
remains unchanged. The apparatus used by
MacLeod and Cave (1975) in Fig. 2-5 is an
evolution of several other workers (Schultz
et al. 1977; Picardi and Issenberg 1973).
Note that this design permits very intimate
mixing of the product steam (no outside
steam) and the distilled extracting solvent.
This provides for very efficient flavor
extraction (Table 2-2). The apparatus
shown in Fig. 2-5 could readily be modified
to permit vacuum operation by replacing the
water bubbler by a vacuum line. This would
permit the use of lower product tempera-
tures and thereby minimize thermally
induced artifact formation.
Since the co-distillation of water is nec-
essary to effectively transfer volatiles into
the distillation head, the design in Fig. 2-5
is not suitable for lipid-based samples.
However, Au-Yeung and MacLeod (1981)
modified the sample flask to permit the
addition of steam. Lipid samples could then
be steam distilled and effectively extracted
using this system (Table 2-3).
A major disadvantage of steam distil-
lation-solvent extraction is that an addi-
tional step (i.e., solvent extraction of the
distillate) must be incorporated into the
method. Now a method whose isolation
efficiency depends on volatility has been
combined with a method whose isolation
efficiency depends on extraction efficiency.
This second step adds additional selectivity
and error to the method.
TABLE2-2. Recovery of components by SDE from a model mixturea,b

Time of SDE: 1h 4h
--
Pressure: Atmospheric pressure 100mm Atm
---
Volume of Solvent: 125 ml 10 mlc 125 ml 125 ml
-
Solvent: Hexane Pentane Ether Hexane Hexane Hexane
-- --
pH: 3.4 5.0 6.5 7.8 5.0d 5.0 5.0 5.0 5.0 5.0

Ethyl acetate 0 0 0 0 0 59 89 19 0 0
Ethyl butyrate 98 99 99 91 99 101 97 84 100 98
Ethyl hexanoate 100 101 101 95 101 102 99 97 103 99
Ethyl octanoate 99 99 100 95 100 102 100 99 100 99
Ethyl 3-hydroxy hexanoate 41 41 41 19 42 44 49 30 6 90
Ethanol 0 0 0 0 0 0 58 0 0 0
1-Hexanol 101 101 103 98 100 102 100 96 98 100
Linalool 73 99 100 96 99 99 97 97 99 98
Octanal 102 102 103 98 102 103 101 99 103 101
Citronella! 59 78 98 94 81 81 79 77 95 80
Carvone 98 97 98 95 98 99 97 97 92 99
• Source: Schultz et al. 1977.
b At a concentration of 165 ppm (w/v) for each compound recovery as percentage of initial amount.
c For this run, additional hexane (13 rnl) was added through the vent to fill the solvent overflow arm before the distillation was started,
and the extract was not concentrated after SDE. ::!1
~
d 1.0 rnl of acetic acid (glacial), titrated in solution to pH 5 with sodium hydroxide, also was present in this run in addition to the usual 0
....
citrate buffer at 0.05 M.
>
::s
q"'
~.
"'
w
w
34 Source Book of Flavors
Carbon dio(ide -
- ocetO<\e Cooden$<Y
FIGURE 2-5. Apparatus for the simultaneous
distillation/solvent extraction from eggs. (MacLeod
and Cave 1975)
Sugisawa et al. (1984) have combined
steam distillation with adsorption to recover
volatiles. Basically, product steam and
stripped volatiles are passed through a
Tenax or charcoal trap, the steam is con-
densed and then returned to the product.
The trap is typically desorbed by solvent
extraction. This technique eliminates some
of the disadvantages of solvent extraction,
but then adds the shortcomings of adsorption
techniques.
An additional variation of the distilla-
tion/extraction approach has been provided
by Umano and Shibamoto (1987). In this
system, the sample is purged with an inert
gas and the purged volatiles are directed
into a water trap that is being continuously
extracted by a refluxing solvent.
Several workers have commented on
artifacts produced during flavor isolation via
steam distillation. Sources of artifacts
include antifoam agents, vacuum greases on
glass joints, contaminated water supplies,
solvent impurities (Jeon et al. 1976); rubber
tubing (Ferretti and Flanagan 1972);
and thermally induced chemical changes
(Azzouz et al. 1976; Schultz et al. 1980;
Koedam et al. 1980; Sugisawa 1984).
Despite these disadvantages, steam dis-
tillation is a very popular method of flavor
isolation. The method is very efficient
(Fig. 2-1, atmospheric SDE and reduced
pressure SDE) and artifacts may be mini-
mized with adequate care.
High-vacuum stripping (molecular distil-
lation) of oils is often used for the isolation
of flavors from lipid-based foods. Molecular
distillation involves the direct transfer of a
volatile from a food sample to a cold con-
denser. The distance a molecule must travel
to the condenser surface must be small in
comparison to the mean free path of the
molecule. This requires very short distances
between the condenser and food sample,
and the use of high-vacuum systems ( <10- 3
Torr). The vacuum requirement limits this
method to the isolation of volatiles from
pure fats and oils (i.e. , having essentially no
water). A very efficient molecular still is
shown in Fig. 2-6. The heated oil sample is
placed in the sample flask (A), the cold
finger (F) chilled with liquid N2 and then oil
is slowly allowed to enter the still. The
thermally jacketed swept surface still pro-
vides a large surface area for the loss of
volatiles. After the oil has passed through
the still, the cold finger is removed and the
volatiles are recovered using a small volume
of solvent in the apparatus labeled B.
Recovery of volatiles via molecular dis-
tillation can be very good. Nawar et al.
(1969) reported 85-99 percent recovery of
hydrocarbons (C9 -C 19) from corn oil using
a similar apparatus. At a still temperature of
55°C, Badings (1970) found 72- 89 percent
 Flavor Analysis 35

TABLE2-3. Percentage recoveries from lipid medium using modified Likens and
Nickerson apparatus for steam distillations

Methyl Allyl
Ethyl acetate& Ethanol& pyrazine& isothiocyanate&
Time
(h) isop.< CH202 isop. CH202 isop. CH202 isop. CH202

0.5 69 85 0 27 69 46 77
(£1) (17) (tr)' (tr) (6) (tr) (tr)
[7) [27) [tr) [tr] [7) [tr] [tr]
1.0 73 81 0 29 63 64 81
(10) (18) (7) (tr) (9) (tr) (tr)
[38) [56) [11) [11) [22) [8) [17)
3.0 83 87 0 44 74 72 79
(45) (80) (8) (14) (12) (10) (16)
[45) [83) [13) [17) [24) [13) [18)
"From Au-Yeung and MacLeod (1981).
b Concentration of 10- 2 M.
c isop. = isopentane.
d Recoveries using the apparatus without applied steam at 100°C are in parentheses and
those at 150°C are in brackets.
e tr = trace.
f Ethanol unresolved from solvent on GC.

recovery of C5 -C19 alkanals from butterfat. steam distillation, molecular distillation or

While elevated still temperatures may result
in artifact formation, a significant advantage
of molecular distillation is the decreased
opportunity for artifact contamination
relative to alternate methods. The most
common artifacts found in flavor isolates
obtained via molecular distillation are
silicone compounds from the high-vacuum
grease used on glass joints. The apparatus
used by Brandt and Jensen (1975) avoids
this source of contamination via the use of
silicone 0-rings to make seals.
dialysis) in order to obtain a flavor isolate.
This additional handling enhances the
probability of artifact production and
eliminates a primary advantage of direct
solvent extraction: the quantitative advan-
tages of solvent extraction. Therefore,
solvent extraction is generally practiced only
on fat-free foods. Foods such as wines,
breads (if no-lipid), fruit and berry juices,
some vegetables and alcoholic beverages are
often solvent extracted to obtain flavor
isolates.

Isolation of Flavors by Solvent Extraction Equipment and Procedures

Most flavor compounds exhibit substantial
solubility in organic solvents such as diethyl
ether, dichloromethane and pentane. There-
fore, nonfat-containing foods and aqueous
distillates (steam distillation methods) may
be solvent extracted to obtain a flavor iso-
late. Unfortunately, when one extracts a fat-
containing food, one obtains a flavor/fat
extract. This solvent extract (fats and
flavors) may be further treated (e.g., by
The method used for solvent extraction is
determined by the physical state of the food
(i.e., solid vs. liquid), quantity of food
(small batch process or large continuous
operation) and extracting solvent (heavier
or lighter than water).
The simplest method of solvent extrac-
tion is batch extraction using separatory
funnels or a Mixxor (Lidex Tech., Bedford,
MA). Parliment (1986) has reported on the
use of the Mixxor (Fig. 2-7) for the recovery
36 Source Book of Flavors

(a)
M

FIGURE 2-6. Apparatus for combined high vacuum degassing and falling film
molecular distillation. (Brandt and Jensen 1975)

of selected flavor components from dilute
aqueous solution. This device is very simple
to use, efficient (better than 90 percent
recovery of the selected model compounds),
sensitive (to c. a. 0.2 ppm) and reproducible.
The primary drawback of the apparatus is its
limited extraction capacity (10m!).
The use of batch extraction with separa-
tory funnels is very common in the litera-
ture. The need to use multiple extractions
with limited solvent quantities rather than a
single extraction with a large solvent volume
is obvious from the concern for artifacts
introduced by the extracting solvent, and
extraction efficiency as evident from the
following equation:
where Wr is weight of solute remammg
following extraction ; W0 , weight of solute in
original solution; Vw' volume of aqueous
phase; V0 , volume of extracting solvent;
D , partition coefficient; and N, number of
extractions.
Since the term in parentheses is always a
fraction, raising this term to a power de-
 Flavor Analysis 37

Continuous liquid/liquid (L!L) extraction

may also be used to obtain flavor isolates
from foods and steam distillates of foods .
Continuous batch L/L generally provides
more efficient extraction (see Fig. 2-1 ,
continuous extraction) and reduced labor
requirements compared to batch separatory
D
funnel methods, but at greater equipment
costs and extraction time. A typical con-
tinuous L/L extraction would take 2-4h.
Continuous batch LIL extractors are com-
mercially available for solvents lighter than
water (Fig. 2-8) and heavier than water. In
Fig. 2-8, solvent (e.g., diethyl ether or
pentane) is placed in the sidearm flask and
Mi xin g Device an aqueous food in the main body of the
apparatus. The solvent is heated and vapors
FIGURE 2-7. Mixing device (A-Solvent reservoir,
travel up the sidearm into the condenser.
B-Plunger, C-Small diameter sample recovery area, The solvent condenses, drops into the
D-Extracted sample). (Parliment 1986) center distribution tube and is forced by
gravity to displace the aqueous food in
this tube. The solvent then exits from
the bottom of the distribution tube and
creases its value quickly. As an example, percolates up through the food to return
if 100 ml aqueous solution containing a to the solvent pot. This design permits
component with D = 100 were extracted continuous extraction with a small volume
five times with 20 ml (5 x 20) of organic
solvent, only 2.4 x 10- 7 the original amount
would remain in the aqueous phase follow-
ing extraction. A single extraction of the
same efficiency would require 4,000 liters of
solvent. It is quite obvious that multiple
extractions must be used for flavor isolation.
If proper care is given to provide adequate
solvent-sample shaking and multiple
extractions are used, excellent recovery of
flavor compounds may be achieved [see
Fig. 2-1., batch extraction and Reineccius
et al. (1972)].
The major problem encountered with
batch solvent extraction is emulsion for-
mation in the separatory funnel. Emulsions
may be broken by the use of centrifugation,
salt addition (only if solvents lighter than
water are used), slow stirring and/or pH
adjustment. Care must be exercised if one is
centrifuging a flammable organic solvent. A
FIGURE 2-8. Continuous liquid/liquid extractor for
second problem with batch extraction is that the extraction of flavors from aqueous systems.
it is tedious and labor intensive . (Courtesy of Ace Glass, Vineland , NJ)
38 Source Book of Flavors
of solvent that is always being distilled for
extraction.
Jennings (1981) has designed a quick
solvent extraction procedure suitable for
quality control work (Fig. 2-9). He has
modified a Babcock bottle to permit rapid
sample addition through the large side tube
and a small center tube for solvent to collect
for GC sampling. Briefly, the aqueous food
sample is added to the bottle, 100 J.tl of
solvent is added and the bottle is shaken
well. Water is then added to bring the
solvent into the bottle neck, the bottle
centrifuged to promote solvent recovery and
the solvent extract sampled by syringe for
direct injection into a GC.
Solids may be solvent extracted using a
Soxhlet extractor at atmospheric pressures if
a suitable low boiling solvent is used. Care
must be taken to use an efficient solvent
GRADUATED
CAPILLARY TUBE
1 •• I.D.
LIGHTER THAN
WATER SOLVENT
[ e • g •'
PENTANE/ETHER]
WATER
SAMPLE
FIGURE 2-9. Modified Babcock bottle for the extraction of flavors from aqueous
essences. (Courtesy of J&W Scientific, Folsom, CA)
condenser for flavor isolation. A problem
with Soxhlet extractors is their unfavorable
solvent-to-sample ratio. There generally
must be nearly a 2 : 1 volume ratio. This
results in a large volume of solvent if a large
quantity of sample is to be extracted. Large
solvent volumes necessitate extreme solvent
purity to minimize artifacts or solvent
contaminants.
An alternate means of extracting a solid
would be to grind the dry food with an inert
bulking agent such as Celite, packing this
blend into a glass chromatography column
and then eluting this column with organic
solvent (Reineccius et al. 1972; Ferretti and
Flanagan 1973).
Solvent Selection
Solvent selection is determined by several
factors: the most important are the com-
--+~11
SOLVENT
SAMPLE

ponents one desires to extract and the food
system being extracted. Nonpolar solvents
such as pentane, hexane, isopentane or
trichlorofluoromethane should be used for
alcoholic beverages since alcohol has limited
solubility in these solvents (Schreier 1980;
Schreier et al. 1979; Williams and Tucknott
1973). The same solvents are recommended
when methanol is used for enzyme inac-
tivation of fresh plant tissue. Nonalcoholic
food systems are often extracted with a
more polar solvent such as diethyl ether.
Diethyl ether is a very common solvent for
flavor extractions since it has a low boiling
point and good solvent properties for most
flavor compounds.
The components being extracted also
influence solvent choice. Very low boiling
flavors require the use of a low boiling
solvent, e.g., Freon 11 (bpt 23.7°C), C02
(- 78°C) or Freon 12 (bpt - 29°C). The
isolation of high boiling flavors permits the
use of hexanes and perhaps even chloroform
as extracting solvent (Kazeniak and Hall,
1980). Since the flavor isolate must gen-
erally be concentrated via evaporation of
the solvent, the solvent should have a lower
boiling point than the components of
interest.
Solvent extraction with liquid C0 2 has
found both industrial and research appli-
cations (Moyler, 1988; Hawthorne et al.
1988; Flament et al. 1987; Moyler and
Heath 1986; Charpentier et al. 1986). Super
critical C02 is particularly attractive as a
solvent since it has a very low boiling point
(i.e., easy to get solvent-free extracts for
either sensory or analytical work and low
boilers are not lost during the concentration
step), it is a good solvent for most nonpolar
solutes, it is nontoxic and reasonably in-
expensive. The primary disadvantage is that
specialized equipment is necessary since the
critical conditions for C02 are 31°C at 73
bar. Extraction equipment costs have
resulted in limited use of supercritical C02
in the flavor research laboratory.
Jennings (1979) has developed a rather
simple system for the extraction of solids
Flavor Analysis 39
with liquid C02 . The solids may be a food
material or a "loaded" porous polymer
headspace trap (e.g., Tenax). He essentially
put a Soxhlet extractor inside a stainless-
steel bomb.
Numerous additional publications have
appeared in the literature in recent years
demonstrating the utility of super critical
fluid extraction in flavor research (e.g.,
Chen et al. 1986; Miles and Quimby 1990).
The advantages of this solvent make it an
excellent choice for flavor studies.
Solvent Impurities
A major problem with solvent extraction is
sample concentration of solvent impurities.
Solvent impurities may be unintentional
such as byproducts of solvent synthesis,
unclean glassware or packaging migrants.
The impurities may be intentional, for
example, antioxidants added to peroxidiz-
able solvents such as diethyl ether. Solvents
are generally purified by distillation using
high reflux ratio and efficient fractionating
columns (Badings 1970). Hydrocarbon
solvents may be "cleaned up" using addi-
tional techniques such as adsorption (on
activated silica gel) and oxidation (strong
acid). Despite the best solvent cleanup and
storage, a solvent blank should always be
run to determine impurities.
Solvent Extraction of Fatty Foods
As was mentioned in the introduction to this
section, fatty foods are generally not solvent
extracted since the solvent co-extracts food
lipids and flavors. When a fatty food is
solvent extracted, the flavor must be iso-
lated from the fat/flavor extract via mole-
cular distillation, steam distillation or
dialysis. Steam and molecular distillation
have been discussed earlier in this chapter.
Dialysis is a relatively new alternative to
distillation (Benkler and Reineccius, 1979,
1980; Chang and Reineccius, 1985). The
most efficient dialysis method uses a tubular
countercurrent continuous dialysis system
(Fig. 2-10). The outer tube is Teflon. The
fat/flavor extract is dissolved in 1 percent
40 Source Book of Flavors
Nltrooen --·==~===alnH
Pressure oouoe ,
Nltrooen ...--'L--'11
FIGURE 2-10. Countercurrent continuous dialysis system for the recovery of
flavors from solvent extracts of fatty foods. (Chang and Reineccius 1985)
water in diethyl ether and is passed through
the center tubing (30m long) at a rate of
about 1 ml/min. Pure 1 percent water in
diethyl ether is passed through the outer
tubing at a rate of approximately 2 ml/min
countercurrent to the sample flow. Re-
coveries of short chain volatiles (up to C6)
are excellent in a single pass through the
system. Recovery drops off quickly as
molecular size of the volatiles increases to
C 10-C14 (ca 20 percent recovery). There-
fore, the method is well suited to the isola-
tion of short chain aliphatics and most
aromatics from fat, but does not perform
well for larger molecular-weight volatiles. A
recent application of this technique for the
isolation of Cheddar cheese flavor was
reported by Vanderweghe and Reineccius
(1990).
Isolation of Individual
Classes of Volatile Flavors
Isolation of individual classes of flavor
components from foods generally takes
advantage of the chemical reactivity of the
class's functional group. This may involve
derivative formation (e.g., 2.4 dinitrophenyl
Pressure oauoo , Solvent lube
Dialysis unit
lOJ
Spent sample
collector
hydrazones of carbonyls) or complex for-
mation (e.g., lead precipitates of thiols).
Class isolation as a chemical derivative
offers several advantages. The derivate
often imparts UV absorbing properties,
which then may permit high-pressure liquid
chromatography (HPLC) separation and
UV detection. Many flavor compounds are
highly volatile and may be unstable. The
derivate is generally stable and of very low
volatility. The specificity of the derivatizing
reagent generally greatly simplifies the
problems of separation and detection. Some
derivates may be regenerated and then
sensory evaluations can be made. This
permits the study of individual classes of
compounds.
A disadvantage of derivative formation
or individual class study is that only a small
part of the overall flavor is being considered
(e.g. , carbonyls or alcohols.) At one time,
analytical techniques (i.e., separation and
detection) were not adequately advanced to
handle the complex mixture of volatiles
found in a flavor isolate. Researchers had to
do individual class separations in order to
simplify the analytical task. Today gas
chromatographic techniques are sufficiently
 Flavor Analysis 41

advanced to permit resolution of very com-
plex mixtures. The use of thick film, narrow
bore fused silica glass capillary columns
has provided tremendous separation capa-
bilities. Detection levels have also been
reduced due to advances in electronics, the
computer age and the use of glass capil-
laries. The need to simplify flavor analysis is
no longer as acute as it once was. Therefore,
we are seeing much less class separation
work in flavor research today. Due to this
declining need for class separations, the
following discussion will be rather brief.
More detailed discussions of this topic may
be found in the reviews of Reineccius and
Anandaraman (1984), Maarse and Belz
(1981) and Bemelmans (1979).
Sulfur Compounds
Most schemes for the isolation of sulfur
compounds depend upon the slightly acidic
nature of sulfur compounds or their binding
to heavy metals (e.g., lead or mercury).
Wilson et al. (1973) isolated sulfur com-
pounds from beef by first making an ether
solvent extract of the beef and then ex-
tracting the ether extract with aqueous
potassium hydroxide. The acidic com-
pounds (e.g., sulfur compounds and acids)
went into the aqueous phase. The aqueous
phase was then acidified and re-extracted
with ether. Washing this ether phase with
water removed the water soluble acids and
left primarily sulfur compounds in the ether
phase.
The classical isolation method for sulfur
compounds depends upon heavy metal
precipitation. Lead acetate is used to trap
out hydrogen sulfide, mercuric chloride for
sulfides, and disulfides and mercuric cyanide
for mercaptans (Grill et al. 1966). Gold has
also been shown to be effective in trapping

Flavor Isolate in Organic Solvent

I
Extraction with Aqueous Mineral Acid
pH 4.0

Aqueous Phase Organic Phase (A)

I
Reextract with
I
Extraction With Aqueous Alkali
Organic Solvent pH 10
I
I I
Aqueous Phase Organic Phase
I
Aqueous Phase Orpc Phase
(Neutral cpds)

Adjust to pH 9 Extract With Organic

with Alkali Solvent

I
Extract with Organic I
I
Solvent Aqueous Phase OrQCJnic Phase

I
I
Aqueous Phase
I
Organic Phase
I
Adjust Ia pH 4
(Basic cpds) with Minimal Acid

I
Extract with
Organic Solvent
I
I
Aqueous Phase Organic Phase
(Acidic cpds)

FIGURE 2-11. Fractionation scheme for the separation of volatiles in acidic,

neutral and basic components. (Reineccius and Anandaraman 1984)
42 Source Book of Flavors
volatile sulfur compounds (Shaw et al.
1980). Farbood and MacNeil (1979) warn
that class separation based on heavy metal
precipitation may not be complete unless
proper technique is observed.
Acids
The most common isolation procedure for
volatile acids starts with steam distillation,
followed by an acid/base separation (Fig.
2-11). The isolated short chain volatile acids
may be analyzed directly by GC, while
longer chain fatty acids are typically con-
verted to the corresponding methyl ester.
Acids may be recovered from fat-free
foods by direct solvent extraction. The food
would first be acidified (pH 2.5) and then
extracted with an organic solvent. The
organic solvent would extract both neutral
components and acids, so further frac-
tionation would be necessary. The frac-
tionation scheme in Fig. 2-11 would be
followed starting at point A.
Silicic acid chromatography has been
used for the isolation of acids from cheese
(Nieuwenhof and Hup 1971). Cheese was
ground with silicic acid and then packed into
a chromatographic column. The column was
then eluted with ether to remove fat, neutral
and basic flavor components. Acids were
eluted from the column using diethyl ether/
phosphoric acid eluant.
A final alternative approach for the
isolation of acidic flavor compounds in-
volves the use of ion exchange chromato-
graphy. An aqueous homogenate of a food
may be passed over an anion exchange
column. The column would be rinsed with
water to remove all materials except for
acids and then the acids would be eluted
with dilute formic acid.
Alcohols
Class isolation of alcohols is generally
accomplished via derivative formation.
Since alcohols are neutral compounds of low
chemical reactivity, quite reactive reagents
are needed for derivative formation. Some
common derivatives used for this purpose
are p-nitro benzoate esters (Connell and
Strauss 1972), pyruvyl chloride-2, 6-dini-
trophenyl hydrazones (Schwartz and Bre-
wington 1967) and benzoates (Gasco and
Barera 1972).
Carbonyls
Carbonyls are highly reactive. Therefore,
chemical derivatives can be formed and
the free carbonyl regenerated with ease.
While 2, 4-dinitrophenyl hydrazine, hy-
droxylamine, bisulfite, 0-aminodiphenyl,
2,4,6-trichlorophenyl hydrazine and car-
boxymethyl trimethyl ammonium chloride
hydrazide (Girard's Reagent T) readily
form stable derivaties with carbonyls, 2,4-
dinitrophenyl hydrazine (DNPH) has been
the reagent of choice. The DNPH deriva-
tives have been used in carbonyl studies for
over 55 years. There is a vast amount of
literature on the use of DNPH derivatives in
flavor studies. A sampling of some of the
literature includes MacDonald et al. 1960;
Moerck and Ball 1979; Reineccius et al.
1978 and Smagula and Bramlage 1977.
A mines
Amines are organic bases that are readily
isolated by acid/base separations discussed
earlier in this chapter. Amines are recovered
in the basic fraction (Fig. 2-11) along with
pyrazines, pyridines, and thiazoles.
Amines may also be derivatized to aid in
class separation and analysis. Moffat et al.
(1972) have described the use of perfluoro-
benzene derivatives for the analysis of pri-
mary and secondary amines. The perfluoro-
benzene group permits analysis by electron
capture detectors. This enhances detection
threshold and minimizes interferences.
CONCENTRATION OF DILUTE
ORGANIC AND AQUEOUS
FLAVOR ISOLATES
Virtually all of the methods used for the
isolation of volatile flavors from foods
discussed produce a dilute solution of
volatiles for GC analysis. These solutions
 Flavor Analysis 43

typically must be concentrated to permit GC peratures used in evaporative methods may

detection. be adequate to oxidize the more labile flavor
Differences in boiling point, freezing compounds. This problem is often mini-
point or polarity between the solvent and mized by evaporating under vacuum, in an
flavor compounds typically form the bases inert atmosphere or through the addition of
for concentration. The method of choice antioxidants (Takeoka et al. 1986).
depends upon the type of flavor involved Equipment used for evaporative con-
and solvent used, as well as purpose of the centration may be very simple or quite
study. For example, a decision to study high sophisticated. The simplest approach is to
boilers only would permit a different type of evaporate the solvent from an Erlenmeyer
concentration as opposed to a study of low flask using gentle heating under a stream of
boilers. nitrogen. Assuming one is using a low
The major problems encountered in the boiling solvent and the most volatile flavor
concentration process include the loss of constituents are not of interest, this is a
volatile flavor compounds and the intro- very suitable method for concentration.
duction of artifacts. However, if one is interested in the low
boiling volatiles, a reflux system should be
employed. A very efficient reflux setup is
Evaporation
the Kuderna-Danish (Fig. 2-12). A high
Evaporative techniques take advantage of reflux ratio provides effective solvent
the differences in boiling point between the removal with minimal loss of volatile
flavor compounds and solvent. Evaporative flavors. A more efficient system is a spinning
techniques are typically used for flavor band fractionating column (Coleman and
isolates in organic solvents (e.g., pentane, Ho 1980a,b). Proper care in operation will
dicholoromethane, diethyl ether and iso- result in nearly complete recovery of
pentane). The solvent must be low in boiling
point, inert, thermally stable and of extreme
purity.
A disadvantage of evaporative tech-
niques is that volatiles may be lost by
co-distillation. Unfortunately, the loss of
different components may not be the same
nor predictable. Therefore, quantitative
results may be in error even when multiple
internal standards are employed. Since the
flavor isolate typically contains a small
amount of water (from the food product or
distillate), care must be taken to remove
water prior to concentration. While this is
typically done via the addition of dessicants
(e.g., anhydrous magnesium sulfate or
sodium sulfate), an alternative would be to
freeze out the water (Buttery and Kamm
1980). Failure to remove the water prior to
concentration will result in steam distillation
of the flavor components and substantial
flavor losses.
FIGURE 2-12. Kuderna-Danish apparatus for the
Concern also has to be given to oxidation concentration of dilute solutions of flavors in organic
of the flavor components. Times and tern- solvents. (Courtesy of Ace Glass)
 44 Source Book of Flavors

volatiles that differ in boiling point from the utilize charcoal, silica gel, alumina, porous
solvent by less than 1°C. polymers or reverse phase packings as
Vacuum systems are occasionally used adsorbents. While most of the early work
for sample concentration (MacLeod and used charcoal (Heinze and Jennings 1966;
Cave 1975; Peacock et al. 1980; MacLeod Steinke and Paulson 1964), concern for
and Pieris 1981). While vacuum systems artifact formation and irreversible binding
may be used routinely, they are particu- of flavor compounds to the charcoal has
larly suited to flavor isolates containing made the porous polymers [Porapak Q
relatively higher boiling and heat sensitive (Vitzthum and Werkhoff 1975)] and reverse
components. phase packings [C 18 (Parliment 1981;
McMurrough et al. 1988)] more desirable.
Freeze Concentration Typically, an aqueous distillate is passed
Freeze concentration may be used to con- through a column of adsorbent. The ad-
centrate flavor compounds in an aqueous sorbent is rinsed and then eluted with an
system (e.g., steam distillate). Partial organic solvent. This process accomplishes
concentration of the aqueous system prior both concentration and transfer of the
to solvent extraction has the advantage of flavor components to a nonpolar solvent for
reducing solvent volumes for extraction. analysis.
Freeze concentration is based on the
property that water will freeze out of
solution as a pure crystal. Therefore, as the FLAVOR ANALYSIS BY
water freezes, solutes become concentrated DIRECT INJECTION
in the unfrozen matrix.
A simple method for freeze concentra- It is theoretically possible to determine
tion is to place the sample in a l0°F cold flavor compounds in food (> 10 ppb) by
injecting the food directly into a GC. One
room overnight and then centrifuge out the
microliter of a food containing a flavor
ice chunks (Hale and Cole 1963). More
elaborate systems include the use of a cold component at 10 ppb would be adequate
finger or stainless-steel beaker to partially (0.01 ng) for analysis. The practical problem
freeze the sample (Kepner et al. 1969). is that water and nonvolatiles such as lipids,
carbohydrates, proteins and minerals are
While freeze concentration seems to be an
also injected into the GC. These com-
ideal process and should be used whenever
ponents may either move into the column
the flavor chemist has an aqueous flavor
and cause chromatographic problems (e.g.,
isolate, it seldom is employed in flavor
column deterioration, poor resolution and
studies. The primary reason freeze con-
changing column characteristics) or ther-
centration is not used is that only minimal
concentration is achievable (5- to 20-fold). mally degrade to produce artifacts. Previous
Beyond a 5- to 20-fold concentration effect, efforts to circumvent these problems have
volatile losses due to surface evaporation, involved the use of specialized inlet systems
occlusion of volatiles in the freezing ice mass, to isolate lipids (Dupuy et al. 1971) and
other nonvolatiles from the GC column and
and entrapment of volatiles as vapors in ice
absorb water (Fischer et al. 1979). The
air pockets become limiting. This limited
system used by Legendre et al. (1979) to
concentration does not appear to justify the
analyze volatiles from aqueous and non-
extra handling and time expenditure.
aqueous systems is shown in Fig. 2-13.
Ground sample is placed in the inlet as-
Adsorption
sembly and then heated while purging with
Adsorption techniques for the concentra- carrier gas. Desorbed volatiles pass through
tion of flavors in aqueous solutions may the Na2S04 trap while moisture is absorbed.
 Flavor Analysis 45

1/18" lUICK CONNECT

SWAGELOl FITTING

SILICONE S EPTUII ---+t;;;::ll!l:;;;l

1/4" B.S. PIPE CAP
BLABS WOOL PLUG ---Hfif TO HELIUM
SUPPLY

&ROUND BAIIPLE - - - t t l
3/B" 0.0. x 3-3/8° GLASS
TUBE
1/4° x a• B.S. PIPE NIPPLE 8 PORT ROTARY VALVE
"INJECT POSITION"
BLASS WOOL PLUG ---;tllt1
1/4" SILICONE CAP~~=~~~~.....I-
B.S. PIPESEPTUM
1/4° TO 1/18" SWABELOl TO VENT
SoBo REDUCER
1/4° S.S. SWABELOl NUT
1/4° x 2-1/2" S.S. TUB.INB ----:.,. ..a: BC COLUMN
"'.
..
Na 2 so 4 COATED MATRIX w

1/8" COPPER TUBING ----<:!!'. oC

COOLINB COILS
8 PORT ROTARY VALVE
"RUN/PURGE" POSITION
1/4° B.S. SWABELOl NUT

1/4" ~?s~'~=~u~::sELOl ----,......___.

1/18° B.S. SWABELOl NUT

FIGURE 2-13. Gas chromatographic inlet system for the direct analysis of volatiles
in foods. (Reprinted with permission of Legendre et al1979, Copyright 1979,
American Chemical Society)

The volatiles travel through the valving
system into the column for analysis.
The availability of bonded phase capillary
columns and on-column injection provides
the opportunity to do direct injection on a
smaller scale. One could directly inject 1 f.d
of oil, slurried food sample or distillate
(Moshonas and Shaw 1987) into a bonded
phase column and chromatograph nor-
mally. A buildup of food materials at the
column head would require column removal
and backflushing with solvent at regular
intervals.
Direct injection offers an ideal method
for quantitation of volatiles in foods. Also,
there is little sample handling or oppor-
tunity for artifacts to enter the analysis. A
limitation is that trace analysis could not be
accomplished; sample size is too small.
Concern would also have to be given for
absolute sample uniformity. Any phase
separation or nonuniformity in flavor dis-
tribution would lead to errors.
GAS CHROMATOGRAPHY
Due to the large number of flavor com-
pounds and their diversity, gas chromato-
graphic separation and measurement is
a most challenging problem (Feeney and
Jennings 1989). While capillary GC columns
offer tremendous resolving powers, it is
often highly desirable to fractionate a flavor
isolate prior to GC analysis.
Fractionation of Flavor Isolates
Some of the more common methods to
fractionate flavor isolates prior to GC
analysis include acid/base separations, high-
46 Source Book of Flavors
pressure liquid chromatography (HPLC),
silicic acid and preparative GC.
Acid/base separations have been dis-
cussed (see Fig. 2-11), and there is no need
to go into this method any further.
The HPLC method is attractive for flavor
fractionation since it uses a different set of
physical properties for separation than GC
does. A flavor isolate may be separated
by adsorption, or reverse or normal phase
chromatography. Adsorption chromato-
graphy is a good initial choice since it has
the greatest column capacity and can handle
the widest range of types of compounds
(Teitelbaum 1977). Fractions based on
adsorption affinity could then be further
fractionated on a normal or reverse phase
column (Parliment 1981). The GC task is
greatly simplified by a prefractionation
scheme such as this.
A simple inexpensive method for flavor
fractionation is via silicic acid (Moshonas
and Shaw 1979; Schreier et al. 1984; Seifert
and Buttery 1978). Basically, the flavor
concentrate would be passed through a
column of silicic acid and then eluted with a
solvent gradient. This effectively frac-
tionates the flavor isolate by compound
polarity. The major problem with this
method is potential artifact formation.
However, careful control of the activity of
the silicic acid and limiting contact time
minimizes artifact formation.
Preparative GC offers the greatest re-
solving power of the fractionation methods.
Typically, a flavor concentrate is chromato-
graphed on a 118-in. or 114-in. o.d. packed
column and the effluent collected via cold
trap in numerous fractions. The solvent-
free fractions may be subjected to sensory
evaluation at this point to focus on a specific
sensory property (e.g., an off-flavor or
desirable note). Proper selection of chro-
matographic cuts can make minor com-
ponents now major components of the
fraction. The primary criticisms of prepara-
tive GC as a fractionation method are that
the sample may be subjected to high tem-
peratures, causing chemical changes and
some compounds may be irreversibly bound
to the GC column. Despite these concerns,
preparative GC has commonly been used
for flavor fractionation (Ho and Coleman
1981; Ho et al. 1982; Hsieh et al. 1982;
Thompson et al. 1978).
Gas Chromatography of
Flavor Concentrates
Flavor research has benefited tremendously
from the development of GC. By 1963, only
500 flavor compounds had been identified in
foods. The development of GC in the mid-
1960s and subsequent application to flavor
research has resulted in nearly 6,000 com-
pounds being identified to date (Maarse and
Visscher, 1989).
Gas chromatography is ideally suited
to flavor studies since it has excellent sep-
aration powers and extreme sensitivity
(picogram detection levels). Resolution and
sensitivity are essential for analysis of
the complex flavor isolates encountered
routinely in flavor work.
In this chapter, we shall not go into a
general treatment of GC since there are
many excellent books on this subject (e.g.,
Jennings 1980a,b; Freeman 1981; van
Straten 1981; Novak 1988). However, we
shall look into some aspects of GC that are
particularly relevant to flavor research.
Capillary Column GC
Capillary column GC has become the
standard for work in the flavor area. A
fused silica column will typically provide
about 3,000 theoretical plates per meter
compared to about 2,500 plates per meter
for an unusually good packed column. This
difference may not seem particularly signi-
ficant until one considers that a packed
column is typically limited to about a 7 m
length while a capillary column may be
more than 50m long. Therefore, the re-
solving power of a capillary column will be
at least 10-20 fold better than the best-
packed column. This vastly improved re-
solution comes at little or no cost in analysis

times. The very thin uniform film coatings
in capillary columns permit very rapid mass
transfer and thereby allow very high linear
gas velocities. Analysis times using gas
capillaries are typically much shorter than
the corresponding analysis on packed
columns. Time becomes quite important
in quality control situations where large
numbers of samples are being run.
Capillary columns provide very repro-
ducible retention times. This is essential for
computerized pattern recognition of GC
profiles and identifications based on Kovats
indices. The fused silica columns offer
exceptional durability and inertness. Their
flexibility and small diameter permit inser-
tion into the injection port and detector of
the GC. This minimizes flavor compound
contact with metal surfaces and dead
volume.
Capillary columns enhance detection
limits. This is accomplished by reducing
column bleed (background) and increasing
the concentration per unit time of a com-
pound in the detector. The new bonded
phase columns exhibit very little bleed
which permits greater sensitivity. The very
minimal band spreading (i.e., sharp GC
peaks) results in less sample being needed to
produce a detector response.
The only disadvantage to capillary
columns has been their limited capacity.
Column capacity is being improved upon by
the development of wide bore thick film
bonded phase columns. While a typical
fused silica column is limited to less than
100 ng of each component, the new thick
film columns will handle about 500 ng of
each component without overloading (Grab
and Grab 1983). While this capacity is still
insufficient for some needs (e.g., trapping
for IR and NMR), it is sufficient for splitting
and smelling or multiple detectors.
Jennings (1980b) has reviewed the use
of two-dimensional (or multidimensional
MDGC), SECAT and multiple pass GC
for improving GC resolving power. MDGC
involves passing a section of one GC run
over a second column of different polarity.
Flavor Analysis 47
This is done in order to improve separation
of one part of a GC run and is accomplished
by valving a part of a run onto a second
column. One would then generate two
separate chromatograms simultaneously.
While this "heart cutting" was initially
accomplished by cold trapping a portion of
the GC run and then reinjecting this cut into
a second analytical system, automated
systems utilizing a cold trap between a dual-
oven GC have been developed (Oreans
et al. 1984).
Flavor studies often can benefit from the
improved resolution obtained using MDGC
(Wright et al. 1986; Rodriguez and Eddy
1986). Nitz et al. (1988) have used MDGC
for the study of parsley, marjoram, garlic
and coffee. Van Wassenhove et al. (1988)
have applied MDGC to the study of celery
flavor.
The SECAT GC involves sequentially
connecting two GC columns of different
polarity and operating the columns at
different temperatures. Apparently quite
dramatic changes in elution time and order
can be accomplished by controlling the
temperature differential between the
columns.
Multiple pass GC is recycling the run on
the same column. Shorter capillary columns
have greater resolution than the longer
capillaries so resolution can be gained by
recycling rather than extending column
length. Over 2,000,000 theoretical plates
have been developed in less than 16 min on
a multiple pass GC system.
Chiral Gas Chromatography
The resolution of chiral compounds by
GC is well documented in the literature
(Mosandl 1990; Schmarr et al. 1990). The
methods of analysis have involved either
direct separation on a chiral GC phase or
the formation of diasteroisomeric deriva-
tives and then separation on an achiral
phase. The chiral activity of the GC phase
may come directly from the properties of
the GC phase (e.g., covalent bonding of
l-amina acids to the phase, e.g., Chirasil
48 Source Book of Flavors
Val, Chrompac, Delft, Netherlands) or
through the addition of complexing agents
(e.g., nickel(II)-bis(3-(heptafluorobutanoyl)-
(1R)-camphorate) to a standard GC phase.
The use of chiral phases has the advantage
of providing resolution of optical isomers
without the task of derivitization. While
the two references provided above are the
most recent in this field, the use of com-
plexation GC has been reviewed by Schurig
(1988) and provides an in-depth view of this
technique.
Separations of chiral compounds em-
ploying derivatization have been in the liter-
ature for some time. Numerous derivitizing
agents have been used. Reagents such as
R( + )-alpha-methoxy-alpha-trifluoromethyl-
phenylacetic acid and (S)( + )-0-acetylman-
delic acid have found considerable use.
Articles by Heusinger and Mosandl (1985)
and Tress! and Engel (1984) outline how
this technique is best utilized for chiral
separations.
Recently, separations of chiral flavor
compounds have been achieved using
cyclodextrin based GC phases. The degree
of interaction of cyclodextrins with flavor
compounds depends both upon how well the
volatiles fit into the center of the cyclo-
dextrin molecule and the chemical similarity
of the two molecules. Since chiral com-
pounds differ only in their spacial arrange-
ments, it is easy to see that chiral separations
are quite logical using a cyclodextrin-based
GC phase.
GC Detectors
The detectors commonly used for flavor
work include flame ionization (FID), ther-
mal conductivity (TCD), electron capture
(ECD), nitrogen-phosphorus (NPD), flame
photometric (FPD) and the human nose. In
the late 1980s, the atomic emission detector
(AED) became available. This detector has
the advantage of being specific for any
element, permits monitoring up to three
elements at a time without effluent splitting,
offers excellent sensitivity and gives a linear
response with concentration (Miles and
Quimby 1990). The ability to easily monitor
flavor compounds with N, S, 0, and Cis a
tremendous benefit in flavor studies (Baloga
et al. 1990). The FID, TCD, and nose are
considered universal detectors, while the
remaining detectors are specific in response.
The early TCD detectors have generally
lacked sensitivity and been incompatible
with capillary columns and thus their utility
in flavor research has been limited. How-
ever, improved sensitivity and low-volume
TCDs have made the TCD more attractive
in recent years, since there is no need for
effluent splitting with this system if the
analyst wishes to sniff the GC effluent. The
entire sample passes through the detector
and is available for odor evaluation. An
experienced chemist can provide a great
deal of information about a chemical eluting
from a GC column. The chemist can typically
give a molecular weight estimate, describe
aroma character, estimate sensory intensity,
and give a useful input as to the functional
group or compound class. For example, it is
relatively easy to distinguish between a
pyrazine and a methoxy pyrazine by odor.
Sniffing produces what is called an "aroma-
gram," i.e., a documentation of sensory
response to each peak or area of a chro-
matogram (Fig. 2-14). An aromagram is
extremely valuable since it indicates where
the chemist should focus efforts. If one is
studying a particular off-flavor, once it is
located in the aromagram, efforts can then
be directed toward the identification of the
compound or compounds of interest. The
aromagram may show that the most im-
portant area of the chromatogram is where
there are no GC peaks. This would suggest
going back to the drawing board and trying
to do a better job in isolation.
Acree et al. (1984) and Grosch (Ullrich
and Grosch, 1987) have developed similar
techniques for attempting to quantify the
importance of individual aroma constituents
in a flavor isolate by smelling the GC
effluent at increasing dilution. As the flavor
isolate is diluted, less and less aroma con-
stituents would be present in the GC column

17
0 10 20
TIME IN MINUTES
FIGURE 2-14. Aromagram of the volatiles isolated from oxidized UHT milk.
(Jeon et a!. 1978)
effluent at sufficient concentrations to give
an aroma sensation. Both Grosch and Acree
create an aromagram which presents a plot
of the last dilution of the isolate (a number)
where the aroma was last smelled vs. GC
retention time (actually Kovats Index). The
theory is that those aroma constituents with
the highest dilution value are most impor-
tant to the aroma of the food being studied.
This is an interesting approach that may
yield useful information; however, the
information may also be grossly in error.
The theories make some assumptions that
may be very wrong. For example, vanillin
never becomes intense as concentration
increases so it may have a very high dilution
value (i.e., is present in the sample at many
multiples of its sensory threshold), but not
be intense in the original food. Another
component, for example butyric acid, may
become very harsh as concentration is in-
Flavor Analysis 49
30 40 50
creased. Thus, two volatiles at the same
dilution value may differ greatly in sensory
perception in the food. Another factor to
consider is that two compounds at similar
dilution values might make differing im-
pressions to a person. Will cadaverol make
the same impression upon a person as the
same dilution value of vanillin? I doubt
it. Character is also important, not only
its sensory threshold. The aroma value
approach to accessing flavor compound
significance also suffers from not consider-
ing the effects of flavor compound interac-
tion. It is well documented in the literature
that synergistic and additive effects occur
in sensory analysis. In principle, we are
attempting to take aroma apart and assess
the contribution of a chemical individually
on flavor in this method when, in reality, we
take all aromas into our nose and consider
the overall response. When interpreting
50 Source Book of Flavors
aroma value information, one has to be
rather cautious.
Quantification
The quantification of aroma constituents in
a food is a difficult task. The physical and
chemical properties of each flavor com-
pound influences isolation efficiency and our
analytical instrumentation responds differ-
ently to given flavor molecules. Thus, we
cannot simply take the GC area counts we
obtain from a run and do quantification. We
need to consider numerous factors in
determining an estimate of flavor concen-
tration in the food product.
Quantification can be done in several
ways. One means is to use external stan-
dards. In this method, one adds known
quantities of the flavor constituents of
interest to the food or model system and
obtains a response from the GC. One then
runs the sample and, based on the propor-
tion of response, an estimate of quantity is
calculated. This method is usually not the
one of choice since there are typically
numerous steps involved in flavor isolation
and thus, opportunities for variability to
enter the data. External standard methods
may be used only when the methodology is
extremely reproducible, e.g., an automated
headspace method.
A better approach involves the addition
of an internal standard (or standards) to
the food matrix prior to flavor isolation.
Commonly, only one internal standard is
added to the food and an assumption is
made that all volatiles behave like this in-
dividual compound. This can be grossly in
error. A more suitable approach is to add
multiple internal standards. Schreier (1980)
used this approach in estimating the volatile
constituents in strawberries. He chose a
polar standard and a nonpolar standard,
added them to a model system and calcu-
lated calibration factors for the volatiles he
wished to quantify.
A better approach is to determine re-
covery and response factors for all of the
volatiles of interest. Guichard (1988) took
this approach for the quantification of vola-
tiles in apricots. This approach yields very
accurate quantitative data, but requires that
all of the volatiles of interest are available as
pure reference compounds. Schieberle and
Grosch (1987) took an even more rigorous
approach in using stable isotope dilution for
the quantification of volatiles in wheat and
rye bread. In this case, each volatile com-
pound must be synthesized, incorporating
stable isotopes (deuterium) into the mole-
cule. Quantification was done by adding
known quantities of each volatile containing
stable isotopes to the food to be studied
and flavor isolation performed. Then, the
volatiles were quantified, using selected ion
monitoring GC/MS to get a relative abun-
dance of the unlabeled volatile vs. the
labeled volatile. This is an ideal approach to
quantify flavor volatiles, but is extremely
costly in terms of time and money.
HIGH PRESSURE LIQUID
CHROMATOGRAPHY
High pressure liquid chromatography is not
particularly well-suited for general flavor
studies partially because flavor most com-
monly involves the study of volatile com-
pounds. Gas chromatography is best suited
for the study of volatiles. Additionally,
HPLC columns lack resolving power and
detectors lack the sensitivity to detect non-
ultraviolet absorbing compounds.
However, HPLC has been applied to
several specific areas of flavor study. HPLC
is particularly well-suited to the study of
compounds with low vapor pressures. A
sampling of the literature where HPLC
has been applied includes studies on the
pungent principles of pepper (Lego 1984;
Kawada et al. 1985; Johnson et al. 1979) and
ginger (Smith 1982; Baronoski 1985; Wood
1987; Chen et al. 1986). The pungent prin-
ciples have traditionally been determined
using sensory techniques (Scoville heat
value). HPLC has also found application
in the determination of hop constituents
(Schulze et al. 1979; Forester et al. 1984),
 Flavor Analysis 51

licorice (Hiraga et al. 1984; Hurst et al. 1987), mass spectrometry (Perkins 1989;
1983), vanilla (Dalang et al. 1982), garlic Hartman et al. 1989; Vernin et al. 1986),
(Miething 1988), coumarin as an adulterant Fourier transform infrared (Williams and
in vanilla (Thompson and Hoffman 1988) Tucknott 1987; Croasmun and McGorrin
and safrole and myristicin in nutmeg and 1989; Morin et al. 1987), and nuclear
mace (Archer 1988). magnetic resonance (Bricout 1982; Horman
1984; Byrne et al. 1986; Riley and Kleyn
1989) for providing the necessary clues
SUPERCRITICAL FLUID
for identification. A discussion of these
CHROMATOGRAPHY methods is outside the scope of this book,
The technique of supercritical fluid chro- so the reader should go to the references
matography (SFC) is in its infancy and thus cited by each technique above, reviews by
has seen limited application in the flavor Reineccius and Anandaraman (1984) or
area. Its use in flavor research will be some- Schreier (1984b) or to individual texts on
what limited for the same reasons as were each of the methods.
discussed for HPLC, i.e., GC is so well-
suited for most flavor studies that it is
SUMMARY
difficult to compete. SFC is best suited to
analytical separations involving very polar This chapter should provide an appreciation
or nonvolatile compounds. A primary for the complexity of food flavors and the
advantage of SFC over HPLC is that the task faced by the analytical flavor chemist.
solvent (eluent) can very readily be re- While the challenge is indeed formidable,
moved from the sample following separ- quite significant progress has been made
ation. Therefore, the technique can quite in flavor chemistry in recent years. This
readily be interfaced with FTIR and MS. chapter closes with some reminders for the
The ease of removing the solvent makes the chemist.
evaluation of collected fractions by sensory The chemist must pick representative
methods also easy. SFC will probably re- samples for analysis and be certain that the
place HPLC applications in the research flavor profile is not altered by factors such as
laboratory to a greater extent than GC microbes or chemical or enzymatic changes
applications. during storage or analysis. The next step is
to choose a method for flavor isolation.
The sample type (containing fat, aqueous
IDENTIFICATION OF
system, etc.), time available (quality control
VOLATILE FLAVORS procedure or research technique), research
In most flavor studies it becomes necessary goal (identify a phenolic off-flavor or low
to identify some or all of the flavor com- boiling fresh notes, etc.) and available
ponents. While there are a large number of equipment (C0 2 extractor, automated
methods available for identification of un- purge and trap, etc.) all contribute to
knowns, only a few are useful in flavor choosing a particular method for flavor
studies. In most cases, the researcher is isolation. In any event, the chemist must
attempting to identify one compound in a evaluate the flavor isolate by sensory
complex mixture. Therefore, the compound methods to be certain that the flavor char-
must be separated from the mixture for acter desired is present in the flavor isolate.
analysis. This may mean high-resolution GC If not, a lot of time may be wasted looking
and a maximum of 500 ng unknown per GC for some flavor notes that were not even
run. Minute sample amounts limit the re- isolated. The next step is concentration of
searcher to GC (Feeney and Jennings 1989; the flavor isolate. Moderate and high boilers
Jennings and Shibamoto 1980; Jennings may be concentrated by simple evaporation
52 Source Book of Flavors
under a stream of nitrogen. Studies on very
low boilers (e.g., hydrogen sulfide or
acetaldehyde) require special care in this
step. Analysis then proceeds with GC of the
flavor concentrate. Capillary column GC is
generally a must. The sample should be
sniffed by an experienced person to give
direction to the study. Identification of all
the flavor components in the isolate should
not be attempted unless that is the research
goal. The task of unnecessarily identifying
every flavor component in a flavor isolate
should be left only to the young and foolish.
One must focus efforts on the flavor com-
ponents of interest. Identifications will
typically be made using a combination
of GC and MS. Identification should be
confirmed by MS, odor and co-chromato-
graphy on two different polarity columns.
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Archer, A.W. 1988. Determination of safrole
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Flavor Analysis 53
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in vanilla flavoring products by high-
performance liquid chromatography. J.
Chromatogr. 43:369-82.
Thompson, J.A., May, W.W., Paulose, M.M.,
Peterson, R.J., and Chang, S.S. 1978.
Chemical reactions involved in deep-fat fry-
ing of foods: VII. Identification of volatile
decomposition products of trilinolein. J.
Amer. Oil Chern. Soc. 55:897.
Tressl, R. and Engel, K.H. 1984. Formation
and Analysis of Optically Active Aroma
Compounds. In Analysis of Volatiles: Methods
and Applications, ed. P. Schreier, pp. 323-42.
Berlin: Walter de Gruyter.
 Flavor Analysis 59

Toulemonde, B. and Beauverd, D. 1985. Head- Aromastoff-Analytik (3). LaborPraxis-June:

space analysis: Trap desorption by microwave 514-517.
energy application to the volatile components Werkhoff, P., Bretschneider, W., Hermann, H.,
of some tropical fruits. In Progress in Flavour and Schreiber, K. 1989. Fortschritte in der
Research 1984, ed. J. Adda, pp. 533-48. Aromastoff-Analytik (4). LaborPraxis-Juli/
Amsterdam: Elsevier. August 1989:616-19.
Ulrich, F. and Grosch, W. 1987. Identification of Werkhoff, P., Bretschneider, W., Hermann, H.,
the most intense volatile flavor compounds and Schreiber, K. 1989. Fortschritte in der
formed during autoxidation of linoleic Aromastoff-Analytik (5). LaborPraxis-Sept:
acid. Z. Lebensm. Unters. Forsch. 184:277- 766-70.
82. Werkhoff, P., Bretschneider, W., Hermann, H.,
Umano, K. and Shibamoto, T. 1987. T. Analysis and Schreiber, K. 1989. Fortschritte in der
of headspace volatiles from overheated beef Aromastoff-Analytik (6). LaborPraxis-Oct:
fat. J. Agric. Food Chern. 35:14-18. 874-80.
Van Wassenhove, F., Dirinck, P., and Schamp, Werkhoff, P., Bretschneider, W., Hermann, H.,
N. 1988. Analysis of the Key Components of and Schreiber, K. 1989. Fortschritte in der
Celery by Two Dimensional Capillary Gas Aromastoff-Analytik (7). LaborPraxis-Nov:
Chromatography. In Bioflavour '87, ed. 1002-9.
P. Schreier, pp. 137-70. Berlin: Walter de Werkhoff, P., Bretschneider, W., Hermann, H.,
Gruyter. and Schreiber, K. 1989. Fortschritte in der
Van Straten, S. 1981. Principles of chroma- Aromastoff-Analytik (8). LaborPraxis-Dec:
tography. In Handbuch der Aroma Forschung, 1121-25.
eds. H. Maarse and R. Belz. Berlin, West Werkhoff, P., Bretschneider, W., Hermann, H.,
Germany: Akademie-Verlag. and Schreiber, K. 1990. Fortschritte in der
Vandeweghe, P. and Reineccius, G. 1990. Aromastoff-Analytik (9). LaborPraxis-Jan/
Comparison of Flavor Isolation Techniques Feb: 51-7.
Applied to Cheddar Cheese. J. Agric. Food Werkhoff, P., Bretschneider, W., Hermann, H.,
Chern. (38):1549-52. and Schreiber, K. 1990. Fortschritte in der
Vercellotti, J.R., St. Angelo, A.J., Legendre, Aromastoff-Analytik (10). LaborPraxis-Mar:
M.G., Sumrell, G., Dupuy, H.P., and Flick, 151-60.
Jr., G.J. 1988. Analysis of Trace Volatiles Werkhoff, P., Bretschneider, W., Hermann, H.,
in Food and Beverage Products Involving and Schreiber, K. 1990. Fortschritte in der
Removal at a Mild Temperature under Aromastoff-Analytik (11). LaborPraxis-
Vacuum. J. Food Comp. Anal. 1:239-49. April: 256-64.
Vernin, G. , Metzger, J., Fraisse, D. , and Scharff, Werkhoff, P., Bretschneider, W., Hermann, H.,
C. 1986. GC-MC (EI, PCI, NCI) Computer and Schreiber, K. 1990. Fortschritte in der
Analysis of Volatile Sulfur Compounds in Aromastoff-Analytik (12). LaborPraxis-May:
Garlic Essential Oils. Application of the Mass 352-9.
Fragmentometry SIM Technique. Planta Weurman, C. 1974. Sampling in airborne
Medica 52(2):96-101. odorant analysis. In Human Responses to
Vitzthum, O.G. and Werkhoff, P. 1975. Environmental Odors, eds. A.J. Turk, W.
Cycloalkapyrazines in coffee aroma. J. Agric. Johnston, and D.G. Moulton, pp. 263-328.
Food Chern. 23:510. New York: Academic Press.
Werkhoff, P., Bretschneider, W., Hermann, H., Widmer, H.M. 1990. Recent Developments In
and Schreiber, K. 1989. Fortschritte in der Instrumental Analysis. In Flavor Science
Aromastoff-Analytik (1). LaborPraxis-April: and Technology, ed. Y. Bessiere and A.F.
306-16. Thomas, pp. 181-90. Chichester: John Wiley
Werkhoff, P., Bretschneider, W., Hermann, H., & Sons.
and Schreiber, K. 1989. Fortschritte in der Williams, A.A. and Tucknott, O.G. 1987.
Aromastoff-Analytik (2). LaborPraxis-Mai Examples of Cryogenic Matrix Isolation GC/
1989:428-30. IR in the Analysis of Flavour Extracts. In
Werkhoff, P., Bretschneider, W., Hermann, H., Flavor Science and Technology, eds. M.
and Schreiber, K. 1989. Fortschritte in der Martens, G.A. Dalen, and H. Russwurm, Jr.,
60 Source Book of Flavors
pp. 259-70. United Kingdom: John Wiley &
Sons, Ltd.
Williams, M.P., Hoff, J.E., and Nelson, P.E.
1972. A precise method for the determination
of dimethyl sulfide in processed foods. J. Food
Sci. 37:408.
Williams, A.R. and Tucknott, O.G. 1973. The
selective extraction of aroma components
from alcoholic distillates. J. Sci. Food Agric.
24:863.
Wilson, R.A., Mussinan, C.J., Katz, I., and
Sanderson, A. 1973. Isolation and identifica-
tion of some sulfur compounds in pressure
cooked beef. J. Agric. Food Chern. 21:873.
Withycome, D.A., Mookerjee, B.D., and Jurza,
A. 1978. Isolation of trace volatile con-
stituents of hydrolyzed vegetable protein via
porous polymer entrapment. In Analysis of
Foods and Beverages, Headspace Techniques,
ed. G. Charalambous. New York: Academic
Press.
Wood, A.B. 1987. Determination of the Pungent
Principles of Chillies and Ginger by Reversed-
phase High-performance Liquid Chroma-
tography with use of a Single Standard
Substance. Flav. Frag. J. 2(1):1-12.
Wright, D.W., Mahler, K.O., and Ballard,
L.B. 1986. The Application of an Expanded
Multidimensional GC System to Complex
Fragrance Evaluations. J. Chrom. Sci. 24:
60-5.
Chapter 3
Flavor Chemistry
INTRODUCTION
The appreciation of flavor is a universal,
everyday experience and is the integrated
response to a complex mixture of stimuli
primarily on the senses of smell and taste,
but also on those associated with sight (color
and appearance), tactile sensations (texture
and mouth-feel) and pain (pungency). As
a consequence, flavor chemistry in its
broadest context is a specialized branch of
organic chemistry that impinges on many
other disciplines, including botany, zoology,
anatomy, physiology, histology, cytology,
etc., for its complete understanding.
Flavor chemistry is here taken to mean
the identification and chemical nature of
components responsible for the odor and
flavor of natural products of plant and
animal origin, and the objective study of
their biogenesis, biosynthesis and deteriora-
tion. It is obviously not feasible in this con-
text to discuss the whole scope of organic
chemical reactions involved in the synthesis
of odorants and flavorants in the laboratory
or commercially. Every year, there are
literally hundreds of aromatic chemicals
synthesized, either as end products or as
intermediates (nearly 6,000 compounds
have been identified to date). While most of
these are identical to those found in nature,
others have no such counterparts. The
majority of such synthetics never achieve
any commercial importance, but a few do
reach full manufacturing scale; they find
application in flavorings and fragrances
once their safety in use is established. The
chemistry of synthetic aromatic chemicals is
well described in the literature (Bedoukian
1991).
For the flavorist and anyone associated
with flavor applications, knowledge of the
sensory mechanisms by which these sub-
stances are perceived and recognized is very
desirable. This, too, is a very specialized
field of physiology, psychology and struc-
tural chemistry. However, this subject is
beyond the scope of this book and the reader
should consult the review by Thompson
(1986) or one of the more detailed references
contained therein. The problems associated
with sensory assessment, agreement on test
methods and the means of communicating
sensory responses and data will be discussed
in a later chapter.
Whether naturally occurring, induced
by processing or cooking, or intentionally
added, flavor in food and related consum-
ables is due to chemicals embracing some
inorganic compounds as well as a whole
spectrum of aliphatic and aromatic organic
61
62 Source Book of Flavors
chemicals. Taste (e.g., sweetness, bitter-
ness, etc.) and certain other attributes
(e.g., pungency, astringency, etc.) are due
to nonvolatile components. The odor of
foodstuffs is the predominant contributor
to their distinctive and often diagnostic
flavor profile. Hence, a study of the volatile
components is of relatively greater im-
portance to the flavor chemist and to the
flavorist aiming to match or reconstruct a
given natural profile than is taste. In the
case of fruit flavors, however, the acid/sugar
ratio can significantly alter the appreciation
of the aromatic impact.
The technical literature contains an ever-
increasing number of articles and research
papers on the biochemistry of natural pro-
ducts. Most of these studies are qualitative
and contain long lists of components that
have been isolated and identified (Maarse
and Visscher 1989). After having ignored
the sensory properties of these compounds
for years, we are seeing more emphasis put
upon determining the sensory contribution
of the flavor compounds identified (Acree,
Bernard and Cunningham 1984, Ullrich and
Grosch 1987, and Ney 1990).
Flavor Classification
Flavors may be classified in many ways, but
from the point of view of their chemistry,
the most realistic classification is that based
on their mode of formation, either naturally
by biosynthetic pathways from known pre-
cursors, or by processing in which biological,
chemical or physical conditions are imposed
on natural or artificial starting materials.
Natural flavors are mostly metabolites so
that their formation in living tissues is com-
plex and dependent on genetic factors and
is influenced by environmental conditions
during the natural growth cycle. Flavors
produced by processing may be direct
breakdown products or complex interac-
tion products depending on the starting
materials and the processing conditions
imposed.
In this section, the chemistry of odor and
taste-stimulating components will be dis-
cussed in the following groups:
a. The biochemistry of volatile and
nonvolatile constituents that are
formed during normal plant metab-
olism and remain in situ when the
plant is harvested (e.g., essential oils,
fruit and vegetable flavors).
b. Flavoring components resulting from
enzyme-catalyzed reactions (e.g.,
enzyme-modified dairy products).
c. Flavoring constituents produced as
a result of microbiological action
and fermentation (e.g., wines, dairy
products, tea).
d. Flavors resulting from heat processing
or cooking (e.g., cooked meat flavors,
roasted coffee).
A basic knowledge of organic chemistry
is assumed, and the aim here is to present
an outline of the more important aspects
of current knowledge and an indication of
present progress, rather than an in-depth
review of the literature on the subject,
leaving the reader to pursue specific topics
by reference to the bibliography.
FLAVOR FORMATION IN PLANTS
Knowledge of precursors and pathways
leading to the formation of flavor in fruits
and vegetables is lacking in many areas.
Emphasis has been placed on determining
what constitutes flavor rather than on the
mechanisms of flavor formation, and the
task of elucidating metabolic pathways in
very complex biological systems is difficult
at best. Other than academic interest, there
is little incentive to determine metabolic
pathways leading to flavor formation. How-
ever, there is a strong interest in determin-
ing what chemicals make up a flavor since
this knowledge could be used to study
the appearance of an off-flavor, produce
an artificial substitute, establish nature
identical status or determine species flavor
differences. The result is rather long lists of
flavor chemicals found in each plant, but
 Flavor Chemistry 63

little understanding of how or why they are
there (Maarse and Visscher 1989).
In this chapter, we examine some of the
known mechanisms of flavor formation in
fruit and vegetables (see Schreier 1984 and
Morton and MacLeod 1990). This dis-
cussion is generally limited to the formation
of volatile flavors or aroma and excludes the
taste sensations.
Biogenesis of Fruit Aroma
The typical flavor of fruit such as bananas,
peaches, pears, and cherries is not present
during early fruit formation, but devel-
ops entirely during a rather brief ripening
period. This flavor development period, or
ripening, occurs during the climacteric rise
in respiration. During this period, metab-
olism of the fruit changes to catabolism and
flavor formation begins. Minute quantities
of lipids, carbohydrate, protein, and amino
acids are enzymatically converted to volatile
flavors. The rate of flavor formation reaches
a maximum during the postclimacteric
ripening phase.
An overall view of flavor formation
during ripening of fruit is shown in Fig.
3-1. Flavors are formed from major plant
constituents (e.g., carbohydrates, lipids
and proteins) under genetic control. Each
metabolic pathway is connected to other
metabolic pathways. As direct products of a
metabolic pathway or as a result of interac-
tions between pathways or end products, a
host of volatile flavors are produced that
contribute to the flavor of a ripe fruit.
Table 3-1 presents typical flavor compounds
which are formed from each major food
constituent (Salunkhe and Do 1976).

ALIPHATIC TERPEHES lo4ETHYL-8RANCH(0

Acids Sesq\Ji fer penes Alcohol< AICOhOh

Alcoholo Hydrocorl>ono Acid• Ac•dt.
(olen Alcohol< Esters (slrrt

Carbonyl• Carbonyl• Carbonyh Corbonyh

Locton•s Monoletp•net

FIGURE 3-1. Biosynthesis of fruit volatiles. (Tressl et al1975)

64 Source Book of Flavors

TABLE 3-1. Predominant human nutrients in production of aroma components

in foods 8

Nutrient Aroma Component

Carbohydrates
Glucose Organic acids:
Fructose Pyruvic acid, acetic acid, propionic acid, acetoacetic acid,
Sucrose butyric acid, hexanoic acid, octanoic acid
Esters:
Pyruvates, acetates, propionates, butyrates, acetonacetates,
hexanoates, octanoates
Alcohols:
Ethanol, propanol, butanol, hexanol, octanol
Aldehydes:
Acetaldehyde, propanal, butanal, hexanal, octanal
Terpenes:
Monoterpene, linalool, limonene, o.-pinene, citronella!,
citral, geranial
Amino acids
Alanine Pyruvic acid, acetaldehyde, ethanol
Valine Isopropanal, isopropanol, a-keto-isobutyric acid
Leucine 3-Methylbutanal, 3-methylbutanol, o.-keto-isocaproic acid
Isoleucine 2-Methylbutanal, 2-methylbutanol
Phenylalanine Benzaldehyde, phenylacetaldehyde, cinnamaldehyde
Hydrocinnamaldehyde, p-hydroxybenzaldehyde
p-Hydroxy phenylacetaldehyde, p-hydroxy cinnamaldehyde,
p-hydroxy cinnamaldehyde
Serine
Threonine } Pyruvic acid
Glycine Thiazoles
Cystine/cysteine Glyoxal
Serine
Fatty acids
Linoleic acid trans-2-trans-4-Decadienal, hexanal, trans-2-oetenal
trans-2-Pentanal, trans 2-hexenol, hexanal
cis-3-Hexenal, cis-3-hexenol
trans-2-trans-4-Heptadienal, propanal
Organic acids
Citric acid }
Oxaloacetic acid Glyoxylic acid, glyoxal, pyruvic acid, acetaldehyde
Malic acid Ethanol
Lactic acid
Vitamins
Carotenoids
13-Carotene 13-lonone
• From Salunkhe and Do (1976).

Flavors from Fatty Acid Metabolism
Volatile flavor compounds may be formed
from lipids via several different pathways.
They involve hydroxyacid cleavage to form
lactones, beta oxidation and lipoxygenase
catalyzed oxidation. While the primary pro-
ducts of these pathways are aldehydes and
ketones, additional oxidations, reductions
and esterifications also yield substantial
quantities of acids, alcohols, lactones and
esters.
In growing fruit, metabolic pathways exist

to synthesize a variety of fatty acids, which
are then incorporated into triglycerides
and other lipids. However, once ripening
commences, these metabolic pathways func-
tion as deterioration mechanisms and break
these lipids down to flavorful compounds.
The formation of flavors via this mechanism
is exemplified by considering flavor forma-
tion in pears. The decadienoate esters are
generally considered carriers of the flavor
of pear (Jennings 1967). These esters are
believed to be formed via B-oxidation of
linoleic acid (see Fig. 3-2). Linoleic acid
is metabolized, two carbons at a time, to
shorter chain CoA derivatives which may
react with alcohols to yield esters. During
this process, isomerizations may occur to
yield the trans-cis isomers. It is interest-
ing that the B-oxidation pathway can
account for all of the volatiles that have
been identified in pear.
Methyl and Ethyl
cla-5, cia-a
tetradecadlenoata
Methyl and Ethyl
trana-2, cla-5
dodecenoata
FIGURE 3-2. Proposed pathway for the production of unsaturated esters in pears.
(Tress! et al1975)
Flavor Chemistry 65
Further enzyme-catalyzed reactions
will occur, such as additional oxidations
or esterifications. Tressl and Drawert
(1973) have demonstrated the conversion of
labeled acetate to acetate esters and labeled
butanoate to butanoate esters by post-
climacteric banana slices. They have further
shown the conversion of hexanoic acid to
hexanol by these tissues.
The production of lactones presents a
second means of obtaining flavor from lipid
sources. Lactones are very important to the
flavor of peaches, apricots and coconuts.
Numerous investigators have proposed
oxidative pathways that would result in
lactone formation (Maga 1976b). A major
pathway involves lipoxygenase action on
linolenic acid. There is little information on
the formation of lactones by mechanisms
other than oxidative degradation. Tang and
Jennings (1968) did propose that lactones
could be formed during fatty acid synthesis.
Methyl and Ethyl
cla-4 decenoate
-
Methyl, Ethyl, Propy~
Butyl and Hexyl
trana-2, cla-4
decadlenoate
66 Source Book of Flavors
Their proposal involved hydration of a y-o
double bond to yield the corresponding
lactone. They conceded that there is no
known mechanism to place a double bond in
the y-o position, but suggested a double
bond shift (from ~-y position) followed by
hydration.
The widest variety of flavor compounds
formed from lipids arises via lipoxygenase
activity. Many of the aliphatic esters,
alcohols, acids and carbonyls found in fruit
are derived from the oxidative degradation
of linoleic and linolenic acids as well as
subsequent interactions and degradations.
While an overview of this process will be
presented here, the reader is encouraged
to consult the more detailed reviews by
Gardner (1989), Buttery (1989), and Schreier
(1986).
The initial step in flavor formation is
lipase action to liberate free fatty acids.
Lipoxygenase enzymes can then attack the
free fatty acids (linoleic and linolenic acids)
to yield various hydroperoxides. Enzyme
systems (hydroperoxide lyases) act on these
hydroperoxides to produce flavor com-
pounds. All of these enzyme systems act
in a stereospecific manner, thus yielding
flavor compounds with definite chiral form.
This defined chirality differentiates flavor
compounds of natural origin from those
synthesized chemically (This is significant
both in terms of sensory properties and the
determination of natural/artificial status).
Further oxidations and interactions yield a
large number of flavor compounds.
Flavors from Amino Acid Metabolism
Amino acid metabolism generates aliphatic
and branched chain alcohols, acids,
carbonyls and esters, which are important to
the flavor of fruit. Yu, Olson, and Salunkhe
(1968a,b,c) demonstrated that valine,
leucine, alanine, and aspartic acid could
be converted to short chain carbonyls by
tomato extracts. The enzymes involved in
these transformations were found to be
located in different sites in the tomato.
The soluble tomato fraction isolated via
centrifugation acted on leucine, while the
mitochondrial fraction metabolized both
alanine and aspartic acid. The activities of
these enzymes were substantially higher in
field-grown vs. hothouse tomatoes (Dalal
et al. 1968). This undoubtedly accounts
for some of the flavor differences between
hothouse and field-grown tomatoes.
Studies on banana tissue slices have
shown that leucine and valine concentra-
tions increase about threefold following the
climacteric rise in respiration (Tressl and
Drawert 1973). Radioactive labeling studies
have shown that these two amino acids are
transformed into branched chain flavor
compounds, which are essential to banana
flavor. As can be seen in Fig. 3-3, the initial
step is deamination of the amino acid
followed by decarboxylation. Various
reductions and esterifications then lead to a
number of volatiles, which are significant to
fruit flavor.
Aromatic amino acids also may serve as
important precursors to fruit flavor. Some
of the aromatic flavor compounds have
been shown to come from tyrosine and
phenylalanine (Fig. 3-4). Odors charac-
terized as "phenolic" or "spicy" could arise
via this pathway.
Flavors Formed from Carbohydrate
Metabolism
Returning briefly to Table 3-1, one can see
that a large variety of volatile flavors can be
traced to carbohydrate metabolism. If one
considers plant metabolism, it is clearly
established that plants obtain all of their
energy directly from photosynthesis. The
photosynthetic pathways involve turning
C02 into sugars that are metabolized into
other plant needs, e.g., lipids and amino
acids. Therefore, one may state that nearly
all plant flavors come indirectly from
carbohydrate metabolism since all of the
other flavor precursors come from carbo-
hydrate metabolism. However, there are
few flavor constituents that come directly
from carbohydrate metabolism.
An exception are the terpenes, which
 Flavor Chemistry 67

o(-Ketogtutorote
NH Gtut'!_mate J Th pp
"'- tn2 ~ "'- l? _/
~COOH E1 /VC'cOOH E2

/
Leucine c(-Ketoiaocaproate

FAD NADH

Nc~oH "'- ~
/Vc,H ! 1
FAOH 2 NAO+

I
3-Methyl butan-1-ol 3-Methyl bulanol

Aikylating
Components
t-+ NADH

~ NAD+
0

l
II
Eater WOOH--
c,S-CoA
3-Methyl butyl- 3-Methyl butonaate
Aiktlating
Components

Eater
-3-Methyl butyrate

FIGURE 3-3. Conversion of amino acids into aroma components of banana as

illustrated by leucine. (Drawert 1975)

may arise from either carbohydrate or The interconversion of terpenes can

lipid metabolism. Citrus products obtain
their characteristic flavor from terpenes.
Limonene, a monoterpene hydrocarbon
possessing little odor, is the major terpene
in most citrus oils often accounting for
nearly 90 percent of the oil. The oxygenated
terpenes, often comprising less than 5 per-
cent of the oil, generally provide the charac-
teristic flavor of different citrus species.
For example, citral is considered the flavor
impact component of lemon oil, yet it is
unusual to find more than 2 percent citral in
a single fold oil.
Terpene formation (Fig. 3-5) is known to
involve the condensation of two molecules
of isoprene (isoprene being synthesized
from acetate via mevalonic acid) to form the
backbone of the monoterpenes (Ruzicka
and Eschenmoser 1953, Charlwood and
Banthorpe 1978). The following step is
cyclization to close the ring and then re-
arrangement to create the host of terpenes
found in nature (Croteau 1986).
occur via several pathways. The conver-
sion of neryl pyrophosphate and linaloyl
pyrophosphate to terpinolene, a-terpineol
and limonene is shown in Fig. 3-5. Addi-
tional terpene conversions have been traced
to oxidoreductase systems in citrus fruits
(Potty and Bruemmer 1970a, 1970b). Figure
3-5 also shows the interconversions of
geraniol, geranial, citronellol and citronella!.
Enzyme systems capable of oxidation/
reduction reactions could account for a host
of terpenes in citrus products.
The peel of citrus fruits contains a large
number of flavone glycosides, some of
which are bitter. Bitter compounds in citrus,
particularly grapefruit, have been the sub-
ject of considerable study since these
components limit consumer acceptance
(Rouseff, Lee and Huefner 1990). There
has been an additional interest in glycosides
of flavor compounds for a long time,
since some flavor compounds such as
benzaldehyde (in bitter almond) and methyl
68 Source Book of Flavors

Shikimic acicl patllwar

~~/ ! ~
Trroaina L - Phenrlalanlna
Clnnamlc acid
COOH
I
H2N-~H

90
~ p-Coumaric •:~~ ;{r;attalc acid Farullc acid 1-Hrdroarterullc acid Slnaplc acid
~ C07 E2 COOH COOH COOH COOH

91!4"4~~~~~
~OH ~OCH3 HO~OCH3 ~CO.y.OCH3
OH OH OH OH OH

i I~ i
:\ CH20H CH21:

~,
Favanoidl : ~OCH3 H3C~OCH3 :
~ OH~ / OH :
~ Lignlnl ...,

3.4-0imathoartoluana Eugenylmatllylatllar Eugenol Ellmlcin 5-Metlloareugenol

FIGURE 3-4. Pathways for the formation of phenolic acids and phenol esters in
banana. (Tress! and Drawert 1973, Copyright 1973, American Chemical Society)

salicylate (sweet birch) are unavailable for
recovery via distillation until the starting
plant material has been fermented to free
the flavoring compounds from their respec-
tive glycosides.
Recently, there has been an expanded
interest in glycosides, since researchers are
finding that a significant amount of flavor
compounds in other plant materials may be
bound to glycosides and be unavailable for
flavoring. Fruits, such as pineapple (Ho
et al. 1990, Wu et al. 1990), blackcurrant
(Marriot 1986), mango (Salles et al. 1988),
passion fruit (Engel and Tressl 1983,
Winterhalter 1990), papaya (Heidlas et al.
1984, Schwab, Mahr and Schreier 1989,
Schreier and Winterhalter 1986), grapes
(Williams et al. 1982, Gunta et al. 1985),
apricot (Chairote, Rodrigguez and Crouzet
1981, Salles et al. 1988), and vanilla beans
(Tokoro et al. 1990) have been shown to con-
tain significant quantities of glycosidically
bound flavor constituents. These con-
stituents are generally phenolic or terpene
in nature. It is of interest that some of the
flavor changes that have been credited to
chemical reaction during cooking, aging
(e.g., wines) or other processing steps are
now being linked to the simple release of
glycosidically bound flavor constituents. An
example is the development of a cooked
pineapple note in canned pineapple (the
release of 2,5-dimethyl-4-hydroxy-3(2H)-
furanone). This note was originally believed
 Flavor Chemistry 69

Meraton•c ac•d (MA) MA Phosphate MA Pyrophosphate

~::~·· ~;,~ ~:·,t ~"'"''"" ~

HO HO HO

t
Llnaloyl PP Neryl PP Geranyl PP

A~A'
o
I
'H

:x;H X
NADH
---+
Terpenoid
reductaee

a Terpineol Citroneltal

/ \,.
"2;:
1l NADPH
Dehydrogenase 1l NADPH
Dehydrogenase

tOH NADH tOH

T;;.tcld
reductase

Terplnolene Llmonene Geraniol Citronellol

FIGURE 3-5. Metabolic pathways leading to the formation of terpenes in citrus

fruits. (Eskin 1979; Potty and Bruemmer 1970)

to arise in the heated pineapple due to
thermally induced degradations in the
pineapple sugars.
Flavor Formation in Vegetables
Flavor formation in vegetables is quite dif-
ferent than in fruits since vegetables do not
have a ripening period as fruits do. While
some vegetables will develop partial flavor
during growth and the remaining flavor
during cellular disruption, most vegetables
develop all characteristic flavor constituents
during cellular disruption. Cellular disrup-
tion may be due to cutting a vegetable prior
to use, to cooking, or to the chewing process.
Cellular disruption permits the mixing of
enzymes and substrates which had been
separated within the cell, thereby result-
ing in the generation of volatile flavor
substances. A few examples of vegetables
that contain flavor prior to cellular disrup-
tion are celery (phthalides and selines),
asparagus ( 1 ,2-dithiolane-4-carboxylic acid),
and bell pepper (2-methyl-3-isobutyl pyra-
zine).
An overview of vegetable flavor for-
mation is presented in Fig. 3-6 (see also
Whitfield and Last 1991). Similar to flavor
development in fruit, fatty acid, carbo-
70 Source Book of Flavors
Llnolalc-
'"'n•••••"c acid
Llpoxyganaea
Carbonyle
l l
Alcoholl
Oxo-aclcle
FIGURE 3-6. Formation of flavor in vegetables. (Tressl et al 1975)
hydrate, and amino acid metabolism serve
to provide the precursors of vegetable flavor.
Also, the action of lipoxygenase on linoleic
and linolenic acids to produce volatile
carbonyls and alcohols is similar in vege-
table flavor formation to that in fruit flavor
formation. The major difference in flavor
development lies in the importance of
sulfur-containing flavor precursors to
vegetable flavor. The thioglucosinolates and
cysteine sulfoxides serve as precursors to
numerous volatile sulfur compounds. An
excellent review on the role of sulfur com-
pounds in food flavor has been written by
Shankaranarayana et al. (1982).
Flavor Formation from
Cysteine Sulfoxide Derivatives
Undoubtedly the best illustration of flavor
formation from cysteine sulfoxide precursors
Nonvolatile Precursors
Thloglucoelnolet.. Cyetalna- Mathyl-
eulloxldal mathlonlna
Precursor-splitting Enzymes
Thlogluooelda. . • C-8-lyaeae Nona
(Healing)
leothlocyanatal
l
Polyaullklal
l
CH 3 -S-CH 3
Nllrllae Alkyl-llllosulflnalas
S•C"'O
Tlllocyanalae
comes from studies on onion flavor. Intact
onion cells have virtually no characteristic
flavor until cellular disruption (cutting,
blending, chewing, etc.). Only seconds after
cell damage, the onion develops full flavor.
This rapid formation of flavor is charac-
teristic of the genus Allium as a whole. This
genus includes onions, garlic and chives.
S-Alk(en)yl-L-cysteine sulfoxides serve
as precursors of flavor in the genus. An
investigation of 27 Allium species found that
they could be placed into three groups based
on the predominance of certain amino acid
precursors (Freeman and Whenham 1975).
The predominant precursors were S-1-
propyl (onion), S-2-propenyl (garlic), and
S-methyl (A. aflaturense B. Fedtschenko)
cysteine sulfoxides. A pathway for the
formation of S-1-propenyl cysteine sulfoxide
has been proposed by Granroth (1970) and
 Flavor Chemistry 71

is presented in Fig. 3-7. The mechanism
of flavor formation from alkyl cysteine
sulfoxide (alliin) is also outlined in Fig. 3-7.
While the initial steps of this pathway are
enzymatic, reactions beyond sulfenic acid
are purely chemical in nature. Sulfenic
acid is extremely reactive, readily forming
the unstable thiosulfinate intermediate
by reaction with a second sulfenic acid
molecule. This thiosulfinate decomposes to
form a relatively stable thiosulfonate and
mono, di- and trisulfides. Considering that
several different alkyl precursors are avail-
able in each Allium species, a host of dif-
ferent mono-, di-, and trisulfides can be
formed via different sulfenic acid combina-
tions. It is these mono-, di-, and trisulfides
which are most important in determining
typical Allium flavor.
Matikkala and Virtanen (1967) found
that nearly half of the cysteine sulfoxide
precursors of onion are bound up as a
y-glutamyl peptides. The alliinase enzyme
cannot act upon these cysteine sulfoxide
flavor precursors until they are freed from
the glutamyl peptide. This can be accom-
plished only via the action of a y-L-glutamyl
transpeptidase enzyme. This enzyme
transfers the glutamyl moiety to another
amino acid. The glutamyl transpeptidases
are present only in sprouted onions, not
mature onions (Schwimmer and Austin

J'-.coo-

VaNna oo- Ketoiaovalerate Methacrylate

1+ L-Cyateine

HOOC
~(l.., COOH

~
t-Propenyi-L-cyatel ne
AUina •• aulloxkle
enzyme
H20

f Tl f f~~·N-CH
o~-N=c"C
HOOC
E{
O
X

N Hydride ahllt
O
HOOC
0
X
_J=\N
~
E'
1

C.. avege

_;r·~
Sulfide +

J'-·'- Hzo~Sultenic acid (2)

D
0

··-·-·"
Diaulllde

..JIG"•-•"'
II / X

\\_ HzC
j:-N•CH N
-' Trlaulllde~ Propenyl tllloaulflnate HOOC
0
0 I

_rr·"-
II It

TIIIoaullonat•

FIGURE 3-7. Biosynthesis of S-1-propenyl-L-cystene sulfoxide, and subsequent

flavor formation in onions. (Granroth 1970)
72 Source Book of Flavors
1971). Therefore, nearly one-half of the
flavor potential of the onion cannot be
utilized for flavor formation.
The Cruciferae family also obtains a
flavor contribution from alkyl cysteine
sulfoxide precursors. The Brassica plants,
part of the Cruciferae family include:
broccoli, brussels sprouts, cabbage, cauli-
flower and rutabagas. S-Methyl-L-cysteine
sulfoxide is the primary cysteine sulfoxide
derivative found in this family. An inves-
tigation of fresh cabbage flavor found that
6 percent of the volatiles was dimethyl
disulfide, 6 percent dimethyl trisulfide,
3 percent dimethyl tetrasulfide, and 1.5
percent methyl ethyl trisulfide (Tress! et a!.
1975).
Flavor Formation from Glucosinolates
Most of the vegetables containing glu-
cosinolates belong to the Cruciferae family.
More than 50 different glucosinolates have
been identified to date (Tress! et a!. 1975).
Glucosinolates are nonvolatile flavor pre-
cursors that are enzymatically hydrolyzed to
volatile flavors when cellular structure is
trana-4-Methylthlo-3-
butane-laothiocyanata
FIGURE 3-8. The formation of volatile flavors in radish root. (Tress! et al1975)
disrupted. The volatile products initially
are isothiocyanates and nitriles. Secondary
reactions lead to the formation of several
other classes of flavor compounds. Fig. 3-8
outlines the pathways proposed to explain
the formation of flavor compounds in the
radish. The glucose moiety is initially
hydrolyzed from the glucosinolate. This
results in an unstable molecule that readily
splits out HS0 4 -. Depending upon molecule
rearrangements, either an isothiocyanate or
a nitrile result. Further reactions result in
the formation of thiols, sulfides, disulfides
and trisulfides.
Additional Pathways for Vegetable F favor
Formation
Carbonyls and alcohols may be present
in significant concentrations in vegetables.
These carbonyls and alcohols typically arise
via fatty acid degradation by lipoxygenase.
The mechanism of formation is similar
to that discussed previously for carbonyl
formation in fruit. However, each plant
has a unique fatty acid composition and
ancillary enzyme system. Therefore,
5-Mathylthlo-4-pantane-nltrHa

although the overall mechanism of flavor
formation from fatty acids is similar be-
tween plants, each plant does develop its
own unique carbonyl profile.
A similar analogy could be made for
the formation of terpenes in vegetables.
Terpenes are rather common to vegetables
(Maarse and Visscher 1989) and arise from
mevalonic acid similar to the mechanism of
formation in fruit. Yet each vegetable con-
taining terpenes has a unique terpene
profile.
Location of Flavor in Plant
As one might expect, flavor is typically
distributed nonuniformly in the plant.
MacLeod and MacLeod (1970) have shown
that allyl isothiocyanate is more abundant in
the outer leaves than in the inner tissues of
cauliflower. Freeman and Whenham (1975)
dissected onion bulbs separating the bulb
into individual leaves and the stem. They
examined each section for lachrymator and
pyruvate. They found that the dry outer
scales had virtually no lachrymator or
pyruvate, but levels increased progressively
in the leaves moving toward the plant center
and stem. Total terpenes are more con-
centrated in the crown of carrots than in the
midsection or tip (Simon et al. 1980a). Not
only is there a difference in total flavor
depending upon the plant part being exam-
ined, but there may also be a difference
in flavor profile (Simonet al. 1980b). There-
fore, if one dissected a plant and ate dif-
ferent individual parts, it would not be
unusual to find a slightly different flavor
character for each part.
Influence of Genetics, Nutrition,
Environment, Maturity and
Storage on Flavor
There is little question that not all apples,
oranges or coffee taste the same. We often
select a particular variety of apple (e.g.,
Delicious) because we prefer the flavor.
Genetics determines the enzyme systems
Flavor Chemistry 73
and precursors involved in flavor forma-
tion. Plant environment also influences
flavor. Soil nutrition provides some of
the essentials for flavor development. For
example, a radish will not develop charac-
teristic flavor if there is little sulfur in the
soil. Growing conditions (e.g., temperature)
influence activity of different enzyme
systems and can significantly alter flavor
development. Certainly the stage of maturity
and storage conditions can further influence
flavor. We know that each piece of fruit or
vegetable is an individual in appearance and
flavor.
There is much literature reporting on dif-
ferences in flavor due to genetics, environ-
ment, harvesting time and postharvest
treatment. Further information in this
subject area can be found in the following
references: Paillard (1981), Eskin (1979),
Salunkhe and Do (1976), Freeman (1979),
Dirinck, De Pooter, and Schamp (1989),
and Heath and Reineccius (1986).
Conclusions
While flavor development in fruits and
vegetables proceeds along many common
paths, there are also several contrasts.
Fruit flavor develops during a short ripen-
ing period, while vegetable flavor develops
primarily during cellular disruption. Fruits
depend heavily upon esters for their charac-
teristic flavor, while sulfur compounds are
typically more important to vegetable
flavor.
Similarities exist in the formation of
alcohols, aldehydes, ketones and acids
by enzymatic pathways. The enzymatically
catalyzed oxidation of lipids is a particularly
important pathway for flavor formation in
both fruits and vegetables.
While the pathways leading to flavor
formation are known for many compounds,
in other cases many pieces of the synthesis
puzzle are missing. It is unfortunate that
most of the research on biosynthesis path-
ways of flavor formation was done in the
74 Source Book of Flavors
early 1970s and that, of late, this area of
study has received minimal attention.
As noted earlier, many factors influence
the flavor of a fresh fruit or vegetable. These
factors include plant genetics, soil nutrition,
growing environment, stage of maturity and
conditions of storage from harvesting to
consumption (see Morton and MacLeod
1991).
CHEMISTRY OF ESSENTIAL OILS
Essential oils are obtained by steam or
water distillation, expression or solvent
extraction from many odorous plant sources
(Guenther 1948-1952, Arctander 1960,
Hodge 1975, Pruthi 1980, Wright 1991)
and are of prime importance to the flavor
chemist. These products, which give the
plant its distinctive aroma, are complex
mixtures of organic chemicals whose nature
and relative proportions are also deter-
mined by the plant species and agricultural
factors, such as environment, climate,
soil conditions, time of harvesting and
postharvesting handling prior to distillation.
The chemicals present in essential oils
may be classified as follows:
a. Hydrocarbons of the general formula
(CsHs)n-the terpenes.
b. Oxygenated derivatives of these
hydrocarbons.
c. Aromatic compounds having a
benzenoid structure.
d. Compounds containing nitrogen or
sulfur.
These constituents are synthesized by the
plant during its normal development and the
chemical composition of the oil is generally
characteristic of any given plant species.
The proportion of the chemicals present
in any given essential oil remains within
predictable limits so that the quality of an oil
may often be expressed in terms of one or
more specific components (e.g., citral in oil
of lemon, the menthol/menthone ratio in
oils of peppermint, etc.). The constituents
range over the whole field of organic chem-
istry and clear relationships have long been
recognized in their biogenesis, chemical
character and sensory attributes. However,
research is still required to establish the
precursors and the precise biochemical
pathways involved in their formation in
the growing plant. The biogenesis of the
terpene hydrocarbons and their oxygenated
derivatives, which form such a diverse
and significant fraction of many essential
oils, has already been the subject of much
research and conjecture over the past three
to four decades; but, in spite of modern
instrumental techniques now available
to the classical analysts, is still not fully
understood. As research progresses, many
aspects of this branch of organic chem-
istry are published in the chemical litera-
ture and reference should be made to
Chemical Abstracts for updated informa-
tion. One should also follow the proceed-
ings of the International Congress of the
Essential Oils, Fragrances and Flavors (e.g.,
Lawrence, Mookherjee and Willis, 1988 and
Bhattacharyya, Sen and Sethi 1989) and
journals such as the Journal of Essential Oil
Research (Allured PubI. Co., Wheaton, IL).
Terpenes
The chemical structure of the terpenes
was established by Wallach in 1887. He
proposed the so-called "isoprene rule" by
which terpenes were considered to be fusion
products of two or more isoprene (C5 H 8 )
moieties. The general formula of the
terpenes is, therefore, (C5H 8)n; where
n = 2 the hydrocarbons are known as
monoterpenes or simply as terpenes; where
n = 3 they are called sesquiterpenes; and
where n = 4 as diterpenes. Triterpenes (C30)
and tetraterpenes (C 40) are also known.
The typical terpenoid hydrocarbon struc-
tures are shown in Fig. 3-9. A comprehen-
sive chart, which provides a graphic picture
of the configurative relations in the mono-
terpene series, was published in 1963 by
Dragoco Co., Holzminden, Germany.
Although the terpene hydrocarbons are
 Flavor Chemistry 75

MONOTERPENES
Acyclic Terpanes

13-terpinene -y-terpinene

10 Bicyclic Terpanes
ocimene myrcene

Monocyclic Terpanes

t. '-carene t. •-carene

limonene isolimonene

sabinene a-pinene

terpinolene a-terpinene
13-pinene camphene
SESQUITERPENES
Monocyclic Terpanes

a-bisabolene 13-bisabolene -y-bisabolene

FIGURE 3-9. Pathways in the biosynthesis of terpenes. Croteau and Loomis 1975.
From Sourcebook of Flavors, Heath.

quantitatively significant in the composition The principal terpene hydrocarbons and

of many essential oils (Table 3-2), they
possess little flavor value. It is probably
inaccurate to say that they have no odor
or flavor but, relative to their oxygenated
derivatives, their contribution is small other
than to convey a definite "freshness" to the
odor profiles.
the essential oils in which they occur are
listed in Table 3-2.
Oxygenated Terpenoid Compounds
Oxygenated derivatives of the terpene
hydrocarbons include alcohols, aldehydes,
76 Source Book of Flavors

Bicyclic Terpenes

a-cadinene p-cadinene -y-cadinene

~p-caryophyllene -y-caryophyllene

6Y<
a-selinene
6:1<P-sellnene

DITERPENES

camphorene

FIGURE 3-9. Continued

ketones and esters. These occur widely
throughout the essential oils and are major
contributors to their distinctive odors and
flavors.
The principal oxygenated terpenoid
derivatives are listed in Table 3-3. Reference
should be made to one of the standard texts
for details of their physical and sensory
characteristics (Arctander 1969; Furia
and Bellanca 1975) and to reviews such as
Bedoukian (1991) for specific details of their
manufacture and chemical reactions.
Benzenoid Compounds
The aromatic compounds based on benzene
form another important group of flavoring
and fragrance components. As with the
terpenes, these constituents of an essential
oil are the result of biochemical reactions
 Flavor Chemistry 77

CH,~
decarboxylation )-(:::'OP,O,H, ~ ... -OP,O,H,
---~
CH, H

9
H H

t
lsopentyl pyrophosphate dimethylallyl pyrophosphate
mevalonolactone

condensation OP,O,H,
COOH~,OH ---~ OP,O,H,
monoterpenes

~
X'oP,O,H, neryl pyrophosphate geranyl pyrophosphate

H H
(trans) f£!!1
~~AH, sesquiterpenes

mevalonic acid
pyrophosphate a-cadinene

dlterpenes

camphorene

Source: After Croteau and Loomis (1975)

FIGURE 3-9. Continued

directly associated with the plant's metab-
olism. They include the whole range of
organic functional groups (i.e., alcohols,
acids, esters, aldehydes, ketones, phenols,
phenol ethers, lactones, etc.) In many cases,
their biogenesis and biosynthetic pathways
have not yet been fully established, but it
would seem that most stem from n-propyl
benzene (C6 H5 (CH2 )zCH3 ) as a precursor
that is enzymatically activated. The result-
ing products are found in various stages of
oxidation with many diverse functional
groups attached to the benzene nucleus.
The biogenesis of naturally occurring
aromatic compounds has been developed by
many workers during the past 40 years. The
chemistry involved is far outside the scope
of this brief review. Some of the inter-
mediate and final molecules display con-
siderable structural complexity in which
spatial and stereoisomerism are common.
After many years of research, the chem-
istry of the major constituents of essential
oils is particularly well documented, and
their synthesis and reactions have been
researched. Some of these are of consider-
able economic importance to the flavor
industry, and the following three examples
illustrate just some of the simpler synthetic
conversions that exist:
a. The conversion of eugenol to vanillin.
b. The conversion of safrole to helio-
tropin.
c. The preparation of anisaldehyde from
anethole.
In this context there is little value in
reiterating the basic chemistry of these
 78 Source Book of Flavors

TABLE 3-2. Terpenoid content of essential oils

Principal Terpenes
Total Terpenes (Guenther 1948-1952;
Essential Oil (%) Lawrence 1976-1978)
Allspice (pi men to berry) 25-35 a-phellandrene, caryophyllene
Anise, China star 10-20 a-pinene, a- and)3-phellandrene, p-cyemene, dipentene,
limonene
Caraway 40-50 limonene, a-pinene
Cardamom 50-55 limonene, sabinene
Cassia/ cinnamon 20-30 caryophyllene, a-phellandrene, p·cymene, a-pinene
Celery seed 80-85 a-limonene, selinene
Clove bud 10-20 !3 -caryophyllene
Coriander 30-35 a· and )3-pinene, ')'·terpinene
Dill 35-45 limonene, phellandrene
Fennel 20-30 a-pinene, a·phellandrene, dipentene
Ginger 90 zingiberene, )3-pinene, a- and )3-phellandrene,
a-camphene, myrcene, p-cymene, 2-selinene,
)3-elemene
Lemon peel 96 a- and )3-pinene, camphene, a-limonene,
a·phellandrene, "Y-terpinene
Lime 90 a- and )3-pinene, limonene, dipentene, bisabolene
Marjoram 40 a-terpinene
Nutmeg/mace 60 a-pinene, camphene, dipentene, p·cymene, limonene
Orange, sweet peel 95-98 a-limonene
Parsley seed 50 a-pinene
Pepper, black 70-80 a·thujene, a-pinene, camphene, sabinene, /3-pinene,
Monoterpenes myrcene
20-30
Sesquiterpenes a·phellandrene, .t:.-3-carene, a-terpinene, terpinolene,
a-cube bene, a·copaene, {3-elemene, )3-caryophyllene,
{3-farnescene, humulene, {3-selinene, a-selinene,
!3- bisa bolene
Peppermint 30 a-pinene, limonene, phellandrene, cadinene
Rosemary 85-90 a- and {3-pinene, camphene
Sage 65 a-pinene
Thyme 60-80 {3-pinene, p-cymene, ')'·terpinene, caryophyllene,
camphene

TABLE 3-3. Principal oxygenated terpenoids and their sources

Compound Form Opt. Form Present in the essential oil of:

MONOTERPENE ALCOHOLS
Aliphatic
Ci tronellol d Java citronella, geranium, Eucalyptus
citriodora, savin, Spanish verbena

Reunion geranium, Bulgarian rose

Geraniol Palmarosa, rose, geranium, citronella,

lemongrass, linaloe, lavender, coriander,
tCH~H ylang-ylang, neroli, petitgrain
 Flavor Chemistry 79

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:

MONOTERPENEALCOHOLS
Aliphatic

Linalool d Mexican linaloe, rosewood, nutmeg, orange,

coriander, Orthodon spp.
Japanese ho, Mexican linaloe, lavender,
spike lavender, lavandin, clary sage,
bergamot, neroli, petitgrain, lemon, lime,
basil, geranium, cinnamon bark

Nero! Neroli bigarade, petitgrain, rose, Mexican

linaloe, lavender, bergamot, citronella

~H~H
Monocyclic

Carveol Caraway, spearmint

Dihydro carveol Caraway, Mentha spp.

Dihydro-a-terpineol American turpentine, pine

Menthol Peppermint, Mentha arvensis

~OH
Neomenthol d Mentha arvensis
Stereo isomer of
menthol
80 Source Book of Flavors

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:

MONOTERPENEALC OHOLS
Monocyclic

Perillyl alcohol Gingergrass, bergamot, savin, monarda,

§"
lavandin, spearmint

Pulegol Not found free in nature but is

intermediate in the formation of menthol

~OH
lsopulegol Lemongrass, in other oils in association
with citronella!

~OH
Terpineol d Cupressus spp., cardamom, star anise,
marjoram, clary sage, neroli
Savory, Iavandin, lemon, lime, cinnamon
leaf
dl Mexican linaloe, Eucalyptus globulus,
petitgrain

Bicyclic
Borneol d Nutmeg, olibanum, rosemary, lavender,
spike lavender, ginger
Cf)OH
Pine, citronella, coriander, valerian

Myrtenol Myrtle
d Spanish eucalyptus

Pinocampheol Hyssop

~OH
 Flavor Chemistry 81

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:

MONOTERPENEALCOHOLS
Bicyclic

Pinocarveol Eucalyptus
H
C----C=CH,
"' /:I c1/H
/ c"'-"'-cH1 , I'oH
C----CH,
H

Sabino! Savin, Cupressus spp.

~OH

2'0H
Thujyl alcohol Wormwood

SESQUITERPENE ALCOHOLS
Aliphatic

Farnesol Ambrette seed, neroli bigarade, rose,

cananga, citronella, lemongrass,
palmarosa, and many floral oils

Nerolidol Neroli bigarade, balsam Peru, balsam

Tolu, ylang-ylang

~OH
Monocyclic

Elemi, Java citronella

82 Source Book of Flavors

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:
SESQUITERPENE ALCOHOLS
Monocyclic

Zingiberol Ginger

~OH
Bicyclic
Santalol East Indian sandalwood

Carlino! a d Galbanum, amyris (West Indian

sandalwood)
Cubeb, cade, Java citronella

Guaiol Guaiac wood

MONOTERPENEALDEHYDES
Ci tral (geranial) Lemongrass, monarda, Eucalyptus spp.
2-trans-3, 7 -dimethyl-2,6-octandien-1-al Leptospermum citrata, Backhousia
citriodora, Java citronella, lemon, lime,
ginger
(Commercially, citra! is a mixture of the
two isomers)

Citra! (neral)
2-cis-3, 7-dimethyl-2,6 octadien-1-al

~CHO
 Flavor Chemistry 83

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:

MONOTERPENEALDEHYDES

Citronella! (rhodinal) d Citronella, Eucalyptus citriodora and

other spp., lemon, rose

~0
Backhousia citriodora, Litsea cubeba,
lemon, tangerine, Ocimum spp.

MONOTERPENE KETONES
Carvone d Caraway, dill seed and dill weed
Spearmint
dl Gingergrass

Dihydrocarvone Caraway

~0
Menthone d Nepeta Japonica
I Pennyroyal, peppermint, buchu leaf,

~0
Calamintha nepeta

lsomenthone
Isomer of menthol d Pennyroyal
I Geranium

Piperitone d Mentha arvensis, Andropogon spp.,

Cymbopogon spp.

~0
Eucalyptus spp.

Pulegone d Pennyroyal, Mentha arvensis, Calamintha

nepeta

~0
84 Source Book of Flavors

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:
MONOTERPENEKETONES

Bicyclic
Camphor d Camphor tree, sassafras, spike lavender
Basil, Dalmatian sage
0

Fenchone d Fennel

Santenone East Indian sandalwood

:70
Thujone Thuja, Dalmatian sage, and other spp.
Tansy, wormwood

Verbenone d Spanish verbena, Eucalyptus spp.

~0
SESQUITERPENE KETONES

Turmerone Turmeric
 Flavor Chemistry 85

TABLE 3-3. Continued

Compound Form Opt. Form Present in the essential oil of:

Ion one d In many floral oils

0 I
a dl
II
Xr--cH=CH·C·CHa

~CHa
0
I Raspberry distillate
;>YcH=CH·C·CH:l

l_,jlCH:1

Irone Orris root, raspberry distillate

0
II
"Cc.cH-CH·C·CHa

CHa
a

aromatic constituents and reference should
be made to the many standard texts for a
fuller treatment of this subject. The prin-
cipal benzenoid components of the essential
oils and their sources are given in Vol. II of
Guenther (1948-1952).
Compounds Containing Nitrogen and Sulfur
Organics containing either nitrogen or
sulfur are not very widely distributed in the
essential oils themselves, but plant materials
containing much albuminous matter do
yield compounds on distillation such as
ammonia, trimethylamine, hydrocyanic acid
and hydrogen sulfide (Guenther 1948-
1952).
Nitrogen Compounds
The following naturally occurring nitrogen-
containing compounds are of interest to
both the ftavorist and perfumer.
Indole-Found in oils of Jasmine and
neroli bigaride as well as many citrus oils.
Skatole-Found in the glandular excre-
tion of the civet cat.
Several essential oils contain esters of
anthranilic acid (o-amino benzoic acid), the
most important being:
Methyl Anthranilate-Found in oils of
neroli bigarade and in many floral oils, in
orange and lemon oil in trace quantities and
also in some varieties of grape juice.
Dimethyl Anthranilate-An important
constituent of tangerine (Mandarin) oils.
Sulfur Compounds
Sulfides occur frequently in plants probably
arising from the degradation of glucosides.
Hydrogen sulfide is present in the dis-
tillation waters of certain umbelliferous
fruits; and dimethyl sulfide (CH3 )zS is
present in the prime distillation of American
peppermint oil from which it is removed by
rectification. Several other sulfur-containing
compounds characterize the so-called
"essential oils" of onion, garlic, mustard,
etc.
Sulfur-containing Oils
Onion Freshly minced onions are
allowed to stand and are then distilled. A
 86 Source Book of Flavors
dark brown oil may be recovered in a yield
of 0.002 to 0.005 percent, depending on the
type of onions used and their ripeness. The
composition of this so-called "onion oil"
was studied earlier by Brodnitz and Pollack
(1970) and more recently by Sass-Kiss et al.
(1989). Twenty volatile sulfur-containing
compounds were identified in this latter
study. The following compounds are among
the most abundant:
methyl-1-propyl disulfide
3,4-dimethyl thiophene
cis methyl-1-propenyl disulfide
trans methyl-1-propenyl disulfide
di-1-propyl trisulfide
cis-1-propyl propenyl disulfide
methyl-1-propyl trisulfide
di-1-propyl trisulfide
Garlic (Allium sativum L.) The pri-
mary precursor present in garlic is S-(2-
propenyl)-L-cysteine sulfoxide, which leads
to the formation of allyl thiosulfinate (or
allicin) that characterizes the freshly crushed
garlic. On standing, this compound forms
allyl disulfide, the thiosulfonate, and trace
quantities of allyl trisulfide.
The organoleptic differences between
onion, garlic, and the other alliaceous species
are explained in terms of the quantitative
and qualitative differences in the occurrence
of the four precursors-1-propenyl-, 2-
propenyl-, 1-propyl- and methyl-L-cysteine
sulfoxide (Freeman and Whenham 1975).
Garlic has recently been the subject of
considerable study in many fields due to
positive health claims (Teleky and Petro
1986, Yu and Wu, 1989, Koch, Berger, and
Vieregge, 1989).
Mustard The characteristic flavor and
pungency of this widely used condiment
is also dependent upon enzymic reaction
involving odorless precursors. Mustard
exists in several varieties of which two are of
commercial importance:
White mustard-the seeds of Brassica alba
Boissier
Black (brown) mustard-the seeds of
Brassic nigra (L). Koch or B. juncea (L).
Cosson
When freshly ground, the seeds exude
only a very slight but distinctive odor. When
mixed with water, the aroma is rapidly and
sharply intensified, becoming strongly
pungent. This is due to enzymatic action
on thioglucoside precursors. The so-called
"mustard oil" is a distillate of the aromatic
compounds produced by this reaction, the
chemistry of which differs somewhat be-
tween species.
White Mustard
The principal constituents of the seeds are:
fixed oil (about 25 percent), a crystalline
thioglucoside, sinalbin, and an enzyme,
myrosinase. In the presence of water,
the sinalbin breaks down to yield D-
glucose, sinapine hydrogen sulfate, and
p-hydroxybenzyl isothiocyanate (acrinyl
isothiocyanate or sinal bin mustard oil). This
latter product has little odor, but is intensely
pungent and is a vesicant.
Black (Brown) Mustard
The seeds contain: fixed oil (about 35-40
percent), protein (about 20 percent), the
thioglucoside, sinigrin, and the enzyme,
myrosinase. Under conditions similar to
those described above the sinigrin breaks
down to yield allyl isothiocyanate, which is a
very volatile compound having the charac-
teristic pungency associated with this
condiment. The chemistry of the reaction
was presented briefly earlier in this chapter.
FRUIT FLAVORS
Whereas certain aromatic plant materials,
including some spicy fruits (e.g., pimento
berry, black pepper, coriander, etc.), have a
high content of odiferous constituents that
can be recovered readily in the form of
essential oils, the flavor components of table
fruits are present in relatively low con-

centrations. Although this enables the fruits
to be eaten and enjoyed per se, the recovery
of concentrates that would be of value to the
flavorist or food processor is limited. In
most cases, the expression of fruit juices
does not yield a product having a significant
level of flavor, and their concentration
without degradation of the thermolabile
aromatic constituents poses consider-
able technological problems. The volatile
aromatic chemicals responsible for the
characteristic odor profiles of specific fruits
belong to all classes of organic compounds,
and for most fruits long lists of components
have already been identified (Maarse and
Visscher 1989). Unfortunately, the degree
of contribution that such chemicals make to
the flavor profile is poorly documented and,
generally, the flavor chemist is only able to
use lists of constituents as a guide, relying
on sensory assessment to establish the
proportion necessary in a mixture to create
the correct nuances in the final profile.
Aromatic Components
The aromatic chemicals responsible for the
distinctive odor and flavor profiles of fruits
comprise:
a. Alcohols in the homologous series C 1
to c,2 with a preponderance of even-
numbered carbon atoms.
b. Carbonyls form a significant fraction
of the odor pattern of many fruits
(e.g., benzaldehyde in stoned fruits,
5-hydroxy-2-methylfurfural in pine-
apple, furfural in strawberries, etc.).
c. Acids present in the volatile fractions
of fruits are limited to two, namely:
formic and acetic. The acids most
usually associated with fruit flavor
are nonvolatile and will be discussed
later.
d. Esters are without doubt the most
important and numerous aromatic
components of fruit flavors, their
nature and proportion often being
characteristic of a given fruit.
Flavor Chemistry 87
e. Lactones are responsible for the
characteristic aromatic notes of many
fruits and give peaches and apricots
their quite distinctive profiles (Tang
and Jennings 1968; Romani and
Jennings 1971). A whole series of
lactones has been isolated from
both unripe and ripened fruits and it
has been found that the ratio of the
various lactones changes during the
ripening process. The ratio of o- and
y- lactones present is of importance in
establishing the flavor quality of the
fruit.
f. Phenols in the form of tannins,
are present in many fruits and are
responsible for the characteristic
astringency. Their presence is more
marked in unripe fruit and diminished
as the fruit ripens, probably due to
polymerization.
Fruit Sugars and Acids
Sugars
The carbohydrates present in fruits are of
considerable importance in the assessment
of their quality and edibility. Those of
interest to the food and flavor chemist may
be classified as:
Sugars
Monosaccharides
Pentoses Arabinose, ribose, xylose
Hexoses Fructose, galactose, glu-
cose
Disaccharides Lactose, maltose, sucrose
Trisaccharides Raffinose
Nonsugars (Polysaccharides)
Pentosans Araban, xylan
Hexosans Celluose, dextrin, glyco-
gen, inulin, starch
The principal sugars found in fruits are
fructose and glucose, which are reducing
sugars, and sucrose, which is a nonreducing
sugar. The amount of sugar present depends
88 Source Book of Flavors

on the fruit and the normal metabolic factors Principal Carboxylic Acids
associated with its development. The speed
of change in composition is greatest at Aliphatic Monobasic Acids
maturation and as the fruit ripens. The rela- Formic H·COOH
Acetic CH3 ·COOH
tive proportions of these sugars, which Butyric CH3(CH2)z · COOH
differ significantly in their sweetness levels, Glycolic OH · CH 3 · COOH
varies considerably between fruits as well as Lactic CH3CH(OH) · COOH
with the stage of ripeness. It is this balance Glyceric CH20H
CHOH
that determines the ultimate level of sweet- COOH
ness of the fruit, although the palatability Pyruvic CH3 · CO · COOH
is more directly related to the balance of Glyoxylic CHO·COOH
sugars and fruit acids present, with many Dibasic Acids
fruits being characterized by this aspect of Malonic HOOC · CH2 · COOH
the flavor profile. Adipic HOOC(CH2}4 · COOH
Fumaric HOOC · CH:CH · COOH
L-Malic HOOC · CH2 · CH(OH) · COOH
Acids Tartaric HOOC · CH(OH} · CH(OH} · COOH
Without the organic acids (e.g., citric, Tribasic Acids
malic, tartaric, etc.), the flavor of most Citric CH2·COOH
fruits would be either sickeningly sweet or I
HO·C·COOH
unpleasantly insipid. Some fruits are par- I
ticularly rich in organic acids either in the CH2·COOH
free state or combined as esters; these may Cyclic
be classified as follows: Benzoic COOH

Aliphatic
a. Monocarboxylic acids (e.g., acetic
acid in grapes)
b. Monocarboxylic acids with al-
coholic or carbonyl groups (e.g.,
glyoxylic acid in unripe apples)
c. Di- and tricarboxylic acids (e.g.,
L-malic acid in apples, citric acid in
many fruits)
d. Sugar acids (e.g., gluconic acid in
plums)
Cyclic
a. Monocarboxylic acids (e.g., p-
coumarylquinic acid in apples)
The principal organic acids of importance
in flavorings are listed below, although not
all of these are found in fruit flavors. Their
use in foodstuffs is described by Dziezak
(1990), and individual properties of many
are discussed later in Chapter 12 as con-
tributors to taste.
FLAVOR OF DAIRY PRODUCTS
When considering the flavor of dairy pro-
ducts, one can readily divide the topic into
the fresh vs. fermented products. Fresh
products would include milk, ice cream and
butter, while fermented products include
cheeses, buttermilk, yogurt and a host of
lesser products (in terms of market volume).
While the flavor of fermented dairy pro-
ducts will be discussed later in this chapter,
when flavors from fermentation in general
are discussed, this section will provide some
coverage of this area (Cheddar and blue
cheeses) as well as the flavor of milk.
Milk
Fresh milk has a bland but characteristic
flavor. One might describe it as being slightly
sweet/salty in taste with a delicate but weak
aroma (Badings 1991). The sweetness
comes from lactose (ca. 4.7 percent), while
the saltiness comes from the milk salts. The
aroma is made up of nearly two hundred

components (Maarse and Visscher 1989)
most of which are present in very low con-
centrations (total aroma concentration less
than 1-100mg/kg milk-Badings 1991) and
thus milk has a subtle aroma rather than
anything characteristic. If one were to
characterize milk aroma, it might be to
describe it as "cooked," which is an artifact
of pasteurization rather than inherent to the
milk itself.
The volatiles present in commercial milk
are derived from several sources, including
the metabolic activity of the cow, volatiles
in the air the cow breathes, components in
the diet of the cow and thermally induced
compounds. The thermally induced com-
pounds arise primarily from protein (various
sulfur compounds) or nonenzymatic brown-
ing (Strecker aldehydes and heterocyclic
compounds). Milk is seldom used as a
flavoring material itself, but rather serves as
a precursor for flavor development, either
by providing sugar and amino acids for
browning or the precursors of fermented
flavors. As is noted later in this chapter, the
fatty acids of milk are unique in nature and
thus provide a unique flavoring character to
heated and fermented dairy products.
Cheese
Cheddar Cheese
The manufacture of Cheddar cheese con-
sists essentially of allowing milk to become
acid by the growth of Lactic streptococci,
adding rennet to form a soft coagulum, cut-
ting this coagulum and allowing the small
cubes of clotted milk to lose whey and mat
together. The curd is finally milled, salted
and packed into a hoop or mold where it is
subjected to considerable pressure. The
formed cheese is then allowed to ripen for
3 to 9 months. Most factories have now
instituted control ripening rooms in which
temperature and humidity are automatically
regulated.
During this ripening period the texture
is changed and the characteristic flavor is
formed. Those two events are closely related
(Lawrence et al. 1983). The aroma of cheese
Flavor Chemistry 89
arises mainly from the volatile components
formed in the curd as ripening proceeds.
These components include esters, fatty
acids, aldehydes, ketones, alcohols, amines
and sulfur compounds. The chief chemical
changes in ripening of the Cheddar type
considered chronologically are (1) fermenta-
tion of lactose to lactic acid and small
amount of acetic and propionic acid and
C02 , (2) proteolysis, and (3) lipolysis. The
most obvious chemical change is the break-
down of the proteins. About 25 percent of
the total protein becomes soluble in ripe
Cheddar cheese. The gradual change from
the rubbery curd or green cheese to the
mellow waxy ripe product appears to be
due chiefly to the action of the proteolytic
enzymes. However, it appears that flavor is
chiefly due to the fermentation reaction and
to lipolysis. Breakdown of the fat has not
received much attention, but it is possible
that lipolysis influences not only the flavor
but also the texture.
Flavor Development
The flavor of cheese is the result of a vast
number of chemical and biochemical re-
actions that take place sequentially or
simultaneously in the protein-water-fat-
mineral system that constitutes green cheese.
These reactions are due to the action of:
1. Starter bacteria and their enzymes.
2. Secondary microflora and their enzymes.
These microflora arise from the in-
digenous microflora of milk that survive
pasteurization or from post pasteuriza-
tion contamination.
3. Coagulant.
4. Indigenous milk enzymes (particularly
important in cheese made from raw
milk).
Role of microorganisms The role of
microorganisms in the development of
characteristic flavor of Cheddar cheese is
well recognized (Mabbit, 1961; Reiter
and Sharpe, 1971; and Lawrence et al.
1976). It is well established that bacteria-
free cheeses are flavorless, while those
90 Source Book of Flavors
containing only starter organisms are
flavorful (Reiter et al. 1967).
The primary role of the starter strepto-
cocci is to convert lactose into lactic acid.
The acid reduces the pH of the system. The
starter also participates via glycolysis,
proteolysis and lipolysis in the develop-
ment of Cheddar flavor (Reiter et al. 1969;
Stadhouders and Veringa, 1973; Umemoto
and Sato, 1975). This has been demon-
strated by the absence of Cheddar flavor
development in cheese acidified by purely
chemical means via d-gluconic acid lactone
(Perry and McGillivray, 1964).
Other bacteria like Lactobacillus
plantarum, Lactobacillus pediococcus and
Micrococcus lactis also may contribute
to flavor (Mabbit, 1961; and Perry and
McGillivray, 1964). Keen et al. (1974) even
concluded that 2-butanone, a flavor com-
pound of Cheddar cheese, is formed only
when nonstarter organisms are present.
Those bacteria come from indigenous
microflora in the milk or from post pas-
teurization contamination. Bacteria are
normally present in the udder milk cisterns.
Bacterial counts of first drawn milk vary
from about 100 to many thousands per
ml. There is, however, little information
about types of organisms responsible or the
stage in the ripening process at which their
influence is exerted (Law et al. 1976a).
Enzymes Most starter organisms die
out rapidly in cheese; there is only a 0.5 to
5 percent survival rate after four weeks
of ripening (Law and Sharpe, 1977). At
this time, the flavor development is not
achieved. Therefore, it appears that the
contribution of the starter to Cheddar
flavor development is due to its enzymes
rather than the metabolism of viable cells.
Bacterial enzyme systems are capable of
numerous reactions: reduction, oxidation,
dehydration, hydrolysis, deamination, de-
carboxylation, phosphorylation, and de-
phosphorylation. These enzyme systems are
released into the medium when the bacteria
die and lysis of the cell walls occurs.
Enzymes other than those of the starter
also contribute to Cheddar flavor devel-
opment. Rennet is used to induce milk
coagulation. About 90 percent of the milk-
coagulating enzymes in rennet are discarded
in the whey. The remaining 10 percent play
a part in maturing Cheddar cheese (Dulley
1974).
In addition, there are, of course, enzymes
naturally present in milk. Many enzymes in
milk are produced by the mammary gland
cells, but some of these enzymes may be
derived from the blood or lymphatic system
around the gland. Milk enzymes include:
lipase, peroxidase, protease, esterase,
xanthine oxidase, catalase, lactase, amylase
and aldolase. Some of them play an im-
portant role in Cheddar flavor development.
Enzyme activity is responsible for some of
the differences in flavor observed between
pasteurized and raw milk cheese. Enzymes
will not be inactivated by pasteurization and
will participate in flavor development of
Cheddar (Reiter et al. 1969).
Microorganisms and enzymes are respon-
sible for the production of flavor compounds
and precursors of flavor compounds. By
their activity they also set the physico-
chemical conditions (pH, oxido-reduction
potential), which will regulate secondary
reactions. However, it is not clear what
part of flavor development is due to each of
these agents (microorganisms and enzymes)
when the contribution is exerted during the
maturation process and how important they
are to Cheddar flavor.
Flavor chemicals Maarse and Visscher
(1989) have listed 213 volatile constituents
as being identified in Cheddar cheese.
In terms of contribution to the flavor of
Cheddar cheese, fatty acids, carbonyls,
sulfur compounds and amino acids-peptides
are the groups which have received the most
attention (Aston and Dulley, 1982).
Fatty Acids
Free fatty acids in cheese are derived from
either the breakdown of the fat by lipolysis
or the metabolism of carbohydrates and
amino acids by bacteria. Lipolysis is the

principal contributor of free fatty acids of
chain length C4 or greater (Reiter et al.
1967; Ohren and Tuckey, 1969; and Foda et
al. 1974). Although most researchers agree
that rancidity develops (i.e., an objection-
able odor) when free fatty acid levels reach
excessive levels (Kristoffersen and Gould,
1957; Bills and Day, 1964; Ohren and
Tuckey, 1965; Deeth and Fitz-Gerald, 1975;
and Law et al. 1976c), there is no consensus
on the contribution of fatty acids to Cheddar
cheese flavor development. Kristoffersen
and Gould (1958, 1960), Kristoffersen
(1967), Ohren and Tuckey (1969), Singh
and Kristoffersen (1970), Harper (1959),
Walker (1961), Patton (1963), Foda et al.
(1974), and Harper et al. (1979) concluded
in favor of the participation of fatty acids
in the flavor of Cheddar. But others, Reiter
et al. (1966, 1967), Singh and Kristoffersen
(1971), Law and Sharpe (1977), Dacre
(1955), and Manning and Price (1977) con-
cluded that fatty acids do not have a direct
contribution to Cheddar flavor.
Carbonyls
A large number of carbonyl compounds (30)
have been detected in Cheddar cheese.
Walker and Keen (1974) suggested that
methyl ketones were derived from esterified
C6 to C14 P-ketoacids and not by P-oxidation
of the higher fatty acids.
The exact role of the carbonyls in Cheddar
flavor is uncertain. Acetaldehyde is a pre-
cursor of ethanol and thus has been impli-
cated in the formation of esters (Vedamuthu
et al. 1966). The methyl ketones have been
extensively examined for their role in Ched-
dar flavor (Day et al. 1960; Walker, 1961;
and Patton, 1963). Walker and Keen (1974)
studied the formation of methyl ketones and
concluded that they did not impart a typical
mature Cheddar flavor to cheese. However,
they conceded that a minor but direct con-
tribution may be made by 2-pentanone,
2-heptanone and 2-nonanone. More recent
work by Manning (1978, 1979a) indicated
that 2-pentanone could be directly impli-
cated in Cheddar flavor.
Flavor Chemistry 91
Sulfur Compounds
Volatile sulfur compounds have long been
considered important to Cheddar flavor,
although Aston and Douglas (1981) con-
cluded that none of the volatile sulfur
compounds could be considered to be useful
as a reliable indicator of flavor develop-
ment. Hydrogen sulfide was the first volatile
sulfur compound implicated in Cheddar
cheese flavor (Kristoffersen and Nelson,
1955; Walker, 1959 and 1961). Kristoffersen
and Gould (1958, 1960) and Kristoffersen
(1967) proposed that certain ratios of HzS to
short chain fatty acids were necessary
for proper flavor development. Lawrence
(1963), Manning (1978) and Manning and
Price (1977) could not establish a relation-
ship between H 2S concentration and charac-
teristic flavor. They concluded that although
H 2 S may contribute to Cheddar flavor, its
presence was not essential.
Keeney and Day (1957) identified
methional in Cheddar cheese headspace.
Methional is a product of the Strecker
degradation; i.e., a reaction between an
amino acid and a diketone resulting in the
formation of an aldehyde of one carbon
atom less than the original amino acid.
When methionine undergoes Strecker
degradation, the main product is methional.
Walker (1959), in contrast, could not con-
firm the presence of methional in Cheddar
distillate. Methional is capable of further
breakdown to methanethiol. Law and
Sharpe (1977) studied the formation of
methanethiol in Cheddar cheese and con-
cluded that it was unlikely to be the product
of bacteria or their enzymes. Methanethiol
has been identified in cheese by Libbey and
Day (1963), Libbey et al. (1963), Manning
and Robinson (1973), Manning (1974),
and Manning and Moore (1979). Manning
(1974) showed a strong relationship be-
tween the concentration of methanethiol
in the headspace and the flavor intensity
of Cheddar cheese. The formation of
methantiol in cheese was studied by Manning
(1979b).
Dimethyl sulfide has been detected in
92 Source Book of Flavors
Cheddar cheese by Patton et al. (1958),
Krogger and Patton (1964), Morris et al.
(1966), Bills et al. (1966), Me Gugan et al.
(1968), Manning and Robinson (1973),
Manning (1974), and Manning et al. (1976).
Patton et al. (1958) claimed that dimethyl
sulfide was responsible for a "top note"
in all good-quality Cheddar. On the other
hand, Manning (1974) concluded that its
presence was not essential to Cheddar flavor
because it occurred inconsistently.
Carbonylsulfide has also been found in
Cheddar cheese (Aston and Douglas 1981
and 1983); however, they concluded that
this compound was unlikely to make a direct
contribution to Cheddar cheese flavor
(Aston and Douglas, 1981).
Amino Acids and Peptides
Mulder (1952), Harper (1959), Kosikowski
(1951), and Kristoffersen and Gould (1960)
found that the flavor of cheese increased
with total free amino acid concentration.
In contrast, Dacre (1953) and Law et al.
(1976b), did not find any correlation be-
tween flavor development and amino acid
concentration.
On the basis of findings prior to 1979,
most researchers concurred that the free
amino acids made little or no direct con-
tribution to Cheddar cheese flavor, but
these amino acids provide an important
background, usually characterized as
brothy, upon which characteristic flavor was
superimposed. Work by McGugan et al.
(1979) has thrown some doubt onto the
simplicity of this view. These authors con-
cluded that the volatiles may contribute
mainly to the quality of the flavor, while the
water soluble fraction provides the intensity
of the flavor.
The contributions of peptides, in par-
ticular small peptides, are probably similar
to those of free amino acids. However,
peptides are better known for their role in
the production of bitterness in Cheddar
cheese. Bitter peptides were isolated from
Cheddar cheese by Harwalkar (1967,
1972), Harwalkar and Elliot (1965, 1972),
Richardson and Creamer (1973), Hamilton
et al. (1974), Schalinatus and Behnke
(1975), and Edwards and Kosikowski (1983).
The production of peptides and amino
acids in the cheese is mainly due to the
proteolytic action of the rennet and the
starter (Lawrence et al. 1972).
Flavor Balance
From the preceding discussion two main
conclusions arise:
1. No compounds have been isolated that
can be singly associated with Cheddar
flavor.
2. There is no general consensus about the
identity of the compounds or even
groups of compounds responsible for
Cheddar flavor.
The most widely accepted theory on
Cheddar cheese flavor is the component
balance theory, whereby Cheddar flavor is
supposedly composed of a number of dif-
ferent compounds that must be present in
the correct proportion (Mulder, 1952). This
hypothesis, however, does not unite the
widely divergent views concerning the
individual components contributing to
cheese flavor: fatty acids, carbonyl com-
pounds, amines, peptides, amino acids,
sulfur compounds and others.
Furthermore, even though this hypothesis
was proposed more than 35 years ago, very
few workers (Kristoffersen 1967 and Ohren
and Tuckey 1969) have tried to determine
the ratios that lead to good Cheddar flavor.
Most of the work published dealt with the
study of one particular class of compounds
independent of the other chemicals present
in Cheddar. This fact may explain why
the literature is full of so many opposite
conclusions.
Kristoffersen (1967) stated that desirable
flavor occurs only when free fatty acids
and hydrogen sulfide are present in definite
interdependent concentrations. At twelve
months, when the ratio of micromoles
of free fatty acids to the micromoles of
 Flavor Chemistry 93

hydrogen sulphide per 100 g of cheese is as present in Cheddar and other cheeses.
14.2, the flavor was described as balanced. The formation of these compounds and
When the value of this ratio was 7.2, the their relative importance to the charac-
cheese was described as sulfide-like, and teristic flavor profile of blue cheese have
fatty acid-like with a ratio of 27.9. been reviewed by Day (1967). Maarse and
Ohren and Tuckey (1969) suggested that Visscher (1989) have provided a tabulation
part of the component balance of Cheddar of flavor compounds found in blue cheese.
flavor was due to a balance of free fatty
acids and acetate. Their results suggest that
at 6 months a good-flavored cheese should Fermentation
contain between 60 and 140 micromoles of Although the commercial development of
free fatty acid + acetate per 5 grams of a submerged fermentation process for the
cheese and that the ratio of micromoles-free production of blue cheese flavor was
fatty acid to micromoles of acetate should patented as early as 1963 by Watts and
be between 0.55 and 1.0. Nelson, the production of a blue cheese
flavor under controlled conditions is the
subject of continued research (Pratt 1989
Roquefort (Blue) Cheese Flavor
and Quehl et al. 1987).
Roquefort and other blue-veined cheeses
are traditionally made from pasteurized
milk containing 3.5 percent fat and about 9
percent nonfat solids. Streptococcus lactis FUNGI
culture is added, the milk coagulated with
It has long been recognized that fungi
rennet and the curd separated. Cultures of
have distinctive odors and hence may be
the mold Penicillium roqueforti may be
a potential source of flavoring materials
added either to the milk before coagula-
(Collins 1979). Mushroom aroma (1-octene-
tion or sprinkled onto the surface of the
3-ol) is produced by Aspergillus oryzae and
separated curds. The cheese is then formed
blue cheese aroma by Penicillium species.
with a relatively loose texture and 2.5-3
Ceratocystis species have been studied in
percent salt added.
some detail for their ability to produce fruit
aromas. The character of the aroma was
Flavor Development found to be dependent upon the organism
The freshly made cheese has little flavor being studied, time of growth, nitrogen
and the strong characteristic flavor and source and carbon source (Hanssen and
appearance are only produced during the Sprecher 1981). While aroma production
60- to 90-day ripening period. A good- by various fungi have been studied, the
quality Roquefort cheese has a sharp quantity of aroma compounds produced are
peppery note, but is still smooth to the typically too low to be of commercial sig-
palate. Lawrence (1966) found a continuous nificance (Scharpf et al. 1986). The aroma
lipolysis of triglycerides and the simulta- constituents are typically in the low parts
neous conversion of liberated fatty acids to per million range, which is adequate for
methyl ketones by the spores and mycelia providing an aroma to the culture but too
of the P. roqueforti during ripening. 2- low to recover cost effectively for flavoring
Pentanone and 2-heptanone, probably purposes. The most likely role of fungi
derived from caprylic acid, and 2-nonanone in producing flavor will be as biological
are of prime importance in the flavor catalysts to accomplish desired chemical
profile. transformations (Gatfield 1986) or for the
The chemicals identified in blue-veined production of individual chemicals (e.g.,
cheese are broadly similar to those reported geraniol by C. variospora, Schindler, 1982).
94 Source Book of Flavors
BLACK TEA AROMA
The freshly picked green leaves of the tea
plant Thea (Camellia) sinensis require
processing in order to induce the formation
of the characteristic odor and flavor of black
tea. The harvested leaves are first allowed to
wither, during which time the carotenoid,
amino acids and flavonol precursors of the
odor and color are formed. The leaves are
then broken to release the oxidase enzymes
present in the cell sap and ensure their close
contact with the precursors. They are then
spread out in layers and allowed to ferment
for several hours during which a primary
oxidation occurs and the leaves assume an
agreeable odor and color. The fermented
leaves are then "fired" at about 85°C; this
induces a secondary oxidation, a reduction
in moisture content and the full develop-
ment of the characteristic odor and color of
black tea.
The enzymatic formation of black tea
aroma has been reviewed by Sanderson
and Graham (1973) and Bokuchava and
Skobeleva (1986). It is established that the
biosynthesis takes place in line with the
processing conditions and Sanderson, Co,
and Gonzales (1981) have outlined the
likely stages in the biochemical reactions
involved.
The main precursors of the odor com-
ponents are amino acids and carotenoids
including ~-carotene, lutein, neoxanthin
and violaxanthin. Quantitative studies
by these researchers have shown that the
carotenoid content of the leaves is sig-
nificantly reduced during fermentation and
that the products of the primary oxidation
of ~-carotene are ~-ionone plus terpenoid
carbonyls. A secondary epoxidation takes
place during the "firing" and results in
the formation of dihydroactinidiole, an
epoxyionone and two trimethyl-substituted
cyclohexanones. Other carotenoids present
similarly oxidize, yielding a-ionone, linalool
and substituted hydroxy and epoxyionones.
Sanderson (1972) and Yamanishi (1978)
listed 145 identified components of black tea
aroma. As of 1989, this number increased
to 541 (Maarse and Visscher 1989). The
most important of these are: limonene,
phenylethyl alcohol, linalool, geraniol,
trans-2-hexenal, phenylethyl acetaldehyde,
a- and ~-ionones, isovaleric acid, benzoic
acid, o-cresol, dimethyl sulfide and n-
ethylformyl pyrrole together with some 18
esters and lactones.
The color of black tea is due to the oxida-
tion of tea flavanols by a catechol oxidase
enzyme system.
FLAVOR FORMATION DURING
THERMAL PROCESSING
The predominant flavor of some food
products develops during thermal process-
ing, either during food manufacture or
home preparation. Some examples of these
foods are meats, chocolate, coffee, french
fries and baked goods. The primary routes
of flavor formation in these foods are the
Maillard reaction, caramelization and
thermal oxidations in fats. This section
of the chapter will present an overview of
these means of flavor production (note
related treatment of this subject matter in
Chapter 5).
Nonenzymatic Browning
Nonenzymatic browning (NEB) encom-
passes browning reactions, including
Maillard browning, caramelization and
ascorbic acid browning. This reaction is
responsible for some of the most pleasant
flavors enjoyed by man. There is no ques-
tion that freshly baked bread, steak, freshly
brewed coffee or chocolate is appreciated by
the consumer. Yet none of these flavors
existed in the product until the food pro-
cessor (or cook) heated the product to
develop the flavor. Hurrell (1982) has pre-
sented an excellent review of the Maillard
reaction in food flavor formation (also see
Reineccius 1990). While the following will
present an overview of this reaction, details
may be found in several other publica-

tions, including Vernin (1982); Parliment,
McGorrin, and Ho (1989); Finot et al.
(1990); and Maarse (1991).
General Overview ofMaillard Browning
Hodge (1953) was the first to present an
outline of the overall reactions involved in
Maillard browning. Generally speaking,
Maillard browning is a reaction between
carbonyls and amines. The carbonyls in
foods most often are reducing sugars, while
the amines come from either amino acids or
proteins. The major end products of the
Maillard reaction are melanoidins and other
nonvolatile (and insignificant to flavor)
compounds. However, a number of inter-
mediates and minor products of the reaction
are formed that are significant to flavor.
Reineccius et al. (1972) have shown that
while 1.3 g (per 100 g beans) of reducing
sugars and amino acids (total) were reacted
during the roasting of cocoa beans, only
0.9 mg of pyrazines were formed. Thus,
about 0.07 percent of the reactants were
transformed into pyrazines, while the
remainder of the reactants went into other
products. Yet these pyrazines are excep-
tionally important to the flavor of chocolate.
It is typically these minor products that
make the largest contribution to flavor.
Factors Influencing Browning Rate
It should be noted that many factors in-
fluence the rate of browning and the par-
ticular flavor pathway predominating in
the reaction. The influence of system com-
TABLE 3-4. Aromas generated by amino acids with sugarsa
Glycine Glutamic Add Lysine
Glucose Burnt candy Chicken tray Burnt fried
potatoes
Fructose Beef broth Chicken Fried
potato
Maltose Beef broth Baked ham Stale potato
Sucrose Beef broth Charred meat Boiled meat
• From El'Ode et al. (1966).
Flavor Chemistry 95
positiOn is obvious if one roasts coffee,
cocoa or soy beans. The influence of system
processing conditions on browning flavor
development is equally obvious if one con-
siders the sensory quality of roasted vs.
stewed meats. Both products have the same
precursor systems for reaction. However,
there are considerable flavor differences
between the two foods.
The vast majority of research on the
factors that influence browning has related
to either the disappearance of starting
materials (e.g., lysine/glucose reactions)
or the production of brown pigments. The
limited amount of work studying factors
that influence flavor formation has focused
largely on the flavor compounds formed via
the heating of model systems (e.g., Tressl et
al. 1989; Shu et al. 1985a,b,c,d; Leahy and
Reineccius 1989a and b; and Nursten 1986).
While system composition (e.g., sugar and
amino acid type) and thermal processing
parameters have been varied in some of
these studies, there have been very few
methodical studies conducted in this area.
Most studies have related overall sensory
properties to variations in reaction mixture
composition or process (Table 3-4).
Temperature
The influence of temperature on flavor
formation may be understood better by
recalling that each particular pathway
of flavor formation has its own activation
energy. To illustrate this influence, consider
the plot shown in Fig. 3-10 (please note that
Methionine Phenylalanine
Cabbage Caramel
Bean soup Dirty dog
Harsh, Sweet
horseradish
Overcooked Chocolate
cabbage
96 Source Book of Flavors
1
0.1
_o.a
}: 0.7
.........
E 0.1
8:0.5
-o.4
~
c 0.3
-0.2
0.1
0~~--~~~~--+--+--~
20
FIGURE 3-10. Hypothetical data for 2,3-dimethylpyrazine (+),methyl
cyclopentenolone (*),and hydroxymethyl furfural (o). (Reineccius 1990)
this plot does not contain valid data, but is
only for illustrating an idea). In this plot,
2,3-dimethylpyrazine has the highest activa-
tion energy, followed by cyclopentenolone
and hydroxymethylfurfural. Activation
energy is equal to the slope of the line
divided by R (natural gas constant). This
plot shows that 2,3-dimethylpyrazine would
have the largest rate constant (or highest
rate of production) at high temperatures
followed by cyclopentenolone and then
hydroxymethylfurfural. As temperature
is decreased to typical storage tempera-
tures, the furfural would be produced at the
highest rate and now the pyrazine would
have the lowest rate. Since each pyrazine,
furan, furfural, etc., would have its own
activation energy, one could put several
hundred lines on this figure and realize how
important temperature is in influencing the
formation of flavor compounds via NEB.
A kinetic study by Leahy (1985) reported
an activation energy of approximately
35 kcallmole for pyrazine and 2-methyl
pyrazine and about 43 kcal/mole for the
dimethyl pyrazines. These high activation
energies indicate a very strong tempera-
ure dependence of pyrazine formation
and explain why pyrazines (roasted, nutty,
toasted notes) do not occur during storage,
but only during high-temperature treatment.
There are other implications of the point
+ 2.3-DioiEP\'R
• UEC'YCPENT.
40 10 80 100 120 140 110
TEUPERATURE
made by presenting Fig. 3-10. It is clear that
one will not get the same flavor balance
by using one temperature vs. another. This
becomes relevent when a flavor company
develops a reaction flavor at one tempera-
ture (e.g., 160°C in a lab scale reactor)
and then goes into the production area and
expects to achieve the same flavor profile
using an atmospheric kettle limited to ca.
100°C. Longer process time at a lower
temperature will not necessarily give the
same flavor as a shorter time at a higher
temperature-in fact, we would be rather
surprised if we did obtain the same flavor
character! Our knowledge of classical
browning does not prepare us for this occur-
rence, since we can readily develop more
color by adjusting time and temperature of
heating.
pH
Our classical knowledge of nonenzymatic
browning tells us that as we go up in pH, we
develop more browning. Can we depend
on this truth for flavor formation? Unfor-
tunately not. pH influences many (but not
all) of the reaction rates in the browning
reaction and this influence is not uniform
(Mottram and Leseigneur 1990). Thus, we
need to use a particular pH to force the
browning reaction as we wish. For example,
meat-like reaction flavors must be heated at

pHs around 5 to 5.5. Meat-like flavor cannot
be obtained at other pHs. Chocolate flavors
are typically run at pHs about neutrality.
Water Activity
Water activity has been found to have a
pronounced influence on the rate on non-
flavor browning reactions (Labuza 1980).
A maximum reaction rate is generally
observed at a water activity of 0.6-0.7. For
flavor, several researchers have noted that
water activity has an influence both on the
rate of flavor formation as well as flavor
character. The work by Shu and Ho (1989)
demonstrates how water activity (or propor-
tion of propylene glycol) can influence
flavor production (Fig. 3-11 ). Another
example is for the formation of chocolate
reaction flavors. A very nice chocolate
flavor can be produced by heating selected
amino acids in propylene glycol as the
solvent (zero water activity). The same
flavor can not be produced in an aqueous
system.
Influence of Fat
Fat typically does not participate directly in
the browning reaction, yet may be quite
important in influencing flavor formation via
browning. As noted later in Chapter 5, fat
is required to give the "species" notes to
meat-like reaction flavors (except for beef,
.-..1.40
1120
f
~ 100
~ 80
0 0 TRITHIOLANE
LL 60 .a.
~
i= ...0
~ 20
:::>
0 0
0
FIGURE 3-11. The formation of selected volatiles as a function of water content in
a model system. (Adapted from Shu and Ho 1989)
Flavor Chemistry 97
which may become "beefy" without beef
tallow in the reaction). While fat will make a
flavor contribution due to primary degrada-
tion products (e.g., unsaturated aldehydes
formed from chicken fat during heating),
fat will also make a flavor contribution by
participating in the browning reaction. Fat
makes its contribution to browning flavors
by yielding long chain aldehydes for par-
ticipation in browning (Ho and Carlin
1989). There is no source of long chain
aldehydes in foods except for the fatty acids.
As the fat degrades due to heat treatment,
the various long chain carbonyls formed will
readily participate in browning, producing
uniquely flavored saturated and unsaturated
compounds.
Summary
Overall, the conditions that influence the
Maillard reaction as measured by either loss
in nutritional value or the generation of
pigments may or may not have a similar
effect on flavor. To develop flavors based on
the Maillard reaction, one cannot depend
upon the classical information presented
in general textbooks or general college
courses. The knowledge is generally not
available, and thus a great deal of art and
trial and error are involved in producing
flavors via Maillard browning. This creates
untold amounts of frustration on the part of
+ THIOPHENES
+ 2-ET-THIAZOLE
* HEXANEDIONE
- HY-PENTANONE
98 Source Book of Flavors
both customers and creative chemists serv-
ing these customers. The frustration comes
in terms of creating the exact profile desired
and reproducing this profile. While flavor
production can most often be accurately
controlled by monitoring system pressure or
temperature (in distillations) or solvent
choice or temperature (extractions), the
Maillard reaction is so poorly understood
and so complicated that there really aren't
any good means of process control or quality
control.
Formation of Flavor Compounds
The most abundant flavor compounds
formed via the Maillard reaction are
aliphatic aldehydes, ketones, diketones and
lower chain length fatty acids. However,
heterocyclic compounds containing oxygen,
nitrogen, sulfur or combinations of these
atoms are much more numerous and sig-
nificant to the flavor of browned foods
(Vernin and Vernin 1982). Substantial work
has been devoted to the identification of
flavor compounds, elucidation of pathways
for formation, and evaluation of sensory
properties of these compounds. Thus, the
reader is directed to Maarse and Visscher
(1989) for compounds identified, the brown-
ing literature in general for pathways,
and Fors (1981) for sensory properties.
Information on the formation of flavor in
bread (Grosch and Schieberle 1991), meat
(Mottram 1991), seafood (Josephson 1991),
beer (Angelino 1991), coffee, cacao and tea
(Flament 1991), and nuts (Maga 1991) has
been reviewed recently.
Flavors from Lipids
Lipids undergo changes during the process-
ing of foods that make a flavor contribution.
These changes may include the indirect
effects noted earlier in this chapter or more
direct effects to be discussed at this point.
Deep Fat Fried Flavor
Chang et al. (1978) have pointed out the
market significance of deep fat frying in
their review of deep fat fried flavor by
noting that over 1.1 billion lb. of fat is used
in the United States annually to process
french fried potatoes, doughnuts and potato
chips. They also noted that the major part
of the 10 billion lb. of fat consumed by
Americans yearly is used for fried foods.
While part of the desirability of deep fat
fried foods lies in the physical properties
imparted to the food by this process (crisping
effects as well as increased palatability due
to fat absorption), the characteristic "french
fried" flavor is quite popular and unique to
this process (Pokorny 1989).
The characteristic deep fat fried aroma is
considered to arise from three mechanisms:
(1) the hydrolysis of triglycerides; (2) oxida-
tion of unsaturated fatty acids; and (3)
pyrolytic reactions. The relative importance
of these reactions depends upon the frying
oil, fried material and frying conditions.
Hydrolytic Reactions
Hydrolytic reactions require the contact of
the triglyceride with water. Additives (e.g.,
emulsifiers) or the buildup of oil degrada-
tion products will increase these reactions.
The presence of anions or cations will also
catalyze these reactions.
Oxidation
The primary source of flavor development
in heated oils is lipid oxidation. Dissolved
oxygen is consumed rapidly during frying
and thus becomes the rate limiting factor.
The process of lipid oxidation at elevated
temperatures is similar to that which occurs
at room temperature with a few exceptions.
First, the oxidation process takes place with
limited oxygen. This changes the relative
proportions of end products, primarily a
lower level of di- and trisubstituted oxida-
tion products.
Second, the hydroperoxides formed
are very unstable at elevated temperatures
and thus do not build up during the frying
process, but all tend to be readily de-
composed during frying. The effect of this
is a more random generation of flavor com-
 Flavor Chemistry 99

pounds since the reaction is no longer
limited to the degradation of the least stable
hydroperoxides.
Pyrolysis Reactions
Pyrolysis reactions do not take place until
temperatures exceed 200°C. This is higher
than normal frying temperatures and thus
pyrolysis reactions do not occur unless the
oil is overheated or comes in contact with
hot metal surfaces. Acrolein, a major prod-
uct of pyrolysis, is a pungent, irritating
volatile compound originating from the
dehydration of free glyceroL Pyrolysis is
considered to have a negative effect upon
the flavor of deep fat frying oils.
Effect of Frying Conditions on Flavor
The flavor of frying oils is not optimum at
the start of frying with fresh oils. The fresh
oil has few degradation products responsible
for the desirable flavor of deep fat fried
foods. Therefore, the flavor quality of fried
foods increases as the oil is used until off-
flavors start to dominate the flavor profile.
Frying temperature has an effect on the
formation of desirable flavor, but little effect
on the rate of oil deterioration (oxygen
limiting) until pyrolysis occurs. Pyrolysis
reactions yield bitter, pungent and irritating
end products. Normal frying temperatures
range from 120-195°C.
Traces of metals have a significant
influence on flavor since they catalyze
oxidation. Similar to room temperature
oxidation, iron is the most catalytic followed
by copper, cobalt and nickeL
Antioxidants are effective in increas-
ing oil stability. Tochopherol is the most
abundant natural antioxidant. Synthetic
antioxidants (TBHQ and BHT) are com-
monly used. One must recall that BHT
is volatile and would be lost from the fry-
ing oil. Antifoaming agents (e.g., methyl

OOH
EICOSAPENTAENOIC ACID (C20:5 n-3)

~POXVGENASE ~POXYGEHASE

"/ \•u ~
OOH h -

' j \;_-
~~']
I
A
H
1 '==/
A /\
\:=./ 'cHO
[
~ .1'\:J\:Ho
(z,Z}l,l-f«)NAQQENAL (z)-3-HEXENAL
!LYASE !lYASE I
Adf.:
(z)-1,5-0CTADIEN-3-<ll ~HO
/\(:
1-PENTEN-3-ot.
I
/v\/HO
~~ ~~~
1 \£,'1-2.1-NONAOIENAl

1\_J'\A ~HpH "'==./'cKpH

' ~ ~ ,. (z,lJ-U~N-1-01. (z)-3-HEXEN+Ol
(z)-1.5-0CTAOIEN-3-oNE

FIGURE 3-12. Proposed mechanism for the enzymatic biosynthesis of some fresh
volatile seafood flavor compounds for eicosapentaenoic acid. (Copyright 1986,
American Chemical Society)
100 Source Book of Flavors
polysiloxane) also lend stability to the
frying oil by preventing foaming and thus
limiting oxygen contact.
Mechanisms of Flavor Formation
The mechanism of flavor formation is quite
detailed and beyond the scope of this book.
Excellent reviews are available in this
subject area and the reader may go to
Pokorny (1989) or an earlier review for
more detail.
Lactones
Lactones may be formed in foods via
microbial action, extensive lipid oxida-
tion or biosynthetic routes (Maga 1976). It
appears that due to inborn errors in metab-
olism, hydroxy acids may be synthesized
and incorporated into the triglycerides
of certain living organisms (Dimick et al.
1969). These hydroxy acids are relatively
unstable and are readily hydrolyzed from
the triglyceride in the presence of water
with heat. Hydrolysis of the hydroxy acid
results in its cyclization to a lactone. Since
the hydroxy acid has no flavor as long as
it is bound to the triglyceride, thermal
processing frees the acid and a flavorful
lactone is produced. This process is one of
the simpler ways in which flavor may be
formed during the processing of foods.
Seafood Flavor
Lipid-derived aroma compounds play a key
role in the flavor offresh seafood (Josephson
1991). When the seafood is harvested,
enzymatic reactions (lipoxygenase) initiate
oxidation of the highly polyunsaturated
fatty acids (e.g., arachidonic acid, eicosa-
5,8,11,17-pentaenoic acid, and docosa-
4,7,10,13,16,19-hexaenoic acid), thereby
yielding fatty acid hydroperoxides. These
hydroperoxides are further broken down
by lyase enzymes to alcohols, which then
are attacked by oxidase enzymes to form
volatile flavor compounds (ketones and
aldehydes) that produce the characteristic
seafood flavor (see Fig. 3-12). The majority
of these compounds are common to normal
lipid oxidation of fish, but the enzyme-
mediated nature of flavor formation results
in a flavor quite different from that associ-
ated with lipid oxidation.
While lipids play a major role in the
formation of seafood flavor, other pre-
cursors and types of flavor compounds are
also of significance. Josephson (1991) has
reviewed the role of sulfur compounds,
isoprenoid-related compounds, amines and
hydrocarbons in fresh seafood flavor (or off-
flavor). He has also included a discussion
of the role of thermal processing on flavor
development in seafood.
Caramelization
Caramelization is the process whereby
sugars are thermally decomposed to yield
a host of nonvolatile products as well as
characteristic flavor compounds (Maga
1989, Greenshields 1972). Unlike Maillard
browning, this process is not amine catalyzed
so the reaction proceeds only at high tem-
peratures. Temperatures of 150°C or greater
are generally required for the reaction
to proceed. The reaction proceeds more
rapidly at high pHs and, therefore, alkali
is typically used in the manufacturing of
caramel flavorings.
FLAVORS FORMED VIA
FERMENTATION
Fermentation is a process that provides us
with a variety of new flavors to enjoy. We
come in contact daily with a variety of food
products produced via fermentation. Some
examples include soy sauce, cheese, yogurt,
bread, beer, wine, fermented fish products
and sausages.
Flavor may be developed from the
primary metabolism of the microorganism
or from residual enzymatic activity once
the microbial cell has lysed. For example,
primary metabolism is responsible for much
of the flavor of alcoholic beverages, while
residual enzymatic activity is essential for
the development of aged cheese flavor.
 Flavor Chemistry 101

A large number of different classes foods. Certainly, the importance of acids to

of flavor compounds can be produced by
microorganisms. Tressl et al. (1978) have
summarized some of the reactions that
microorganisms may accomplish (Table
3-5). This section will present some meta-
bolic pathways leading to the development
of flavor in fermented food products. The
book by Margalith (1981) is recommended
for greater detail.
Esters
Esters are quite important to the flavor of
both natural foods (e.g., fresh fruit) and
fermented foods. Of the fermented foods,
esters are probably the most important class
of flavor compounds in alcoholic beverages.
Maarse and Visscher (1989) have listed 94
different esters as being identified in beer.
Most of the esters found in beer are formed
via primary fermentation. They have been
linked to the metabolism of lipids by yeast.
Lipid metabolism provides a large number
of acids and alcohols that may undergo
esterification to yield a variety of esters.
While pure chemical reactions can lead to
ester formation, this reaction is too slow
to account for the esters in most foods.
Nordstrom (1965) has demonstrated that
esterification is controlled by intracellular
enzymes.
Acids
Acid production via microorganisms is im-
portant to the flavor of many fermented
both fermented dairy products and pickled
products cannot be overemphasized.
The acid of greatest importance to the
flavor of fermented dairy products is lactic
acid (Dumont and Adda 1979). Lactic acid
is an optically active acid existing as the D,
L or optically inactive mixture depending
upon the microorganism involved in its
synthesis. There appears to be no difference
in flavor between the optical isomers. Lactic
acid is characterized as being odorless and
having a sour milk taste.
The organisms most commonly as-
sociated with lactic acid formation are
classified as being either homofermentative
(e.g., Lactobacillus bulgaricus, which
produces primarily lactic acid, >85 percent
of metabolic end products) or hetero-
fermentative (e.g., Leuconostoc sp., which
produces lactic acid, acetic acid, ethanol,
carbon dioxide, and other metabolites). The
homofermentative organisms employ the
Embden-Meyerhof pathway for lactose
fermentation, while the heterofermenta-
tion organisms metabolize lactose via the
hexose-monophosphate pathway (Margalith
1981). Lactic acid will reach concentrations
of up to 2 percent or greater in cultures of L.
bulgaricus or L. acidophilus.
Lactic acid is also formed in wines during
fermentation from L-malic acid. Malic acid
is a very tart acid present in grapes that
needs to be converted to lactic acid to
"smooth out" the harsh acidity. This
"malolactic" fermentation is the result of

TABLE 3-5. Reactions catalyzed by microbes•

Oxidation Acylation
Oxygenation of CH or C==C Transglycosidation
Dehydrogenation of CHOH Methylation
Dehydrogenation of CH-CH Condensation
Reduction Cleavage of C-C
Hydrogenation of C 0 Decarboxylation
Hydrogenation of C==C Dehydration
Amination/Deamination
Isomerization Halogenation
Esterification/Hydrolysis Phosphorylation
• From Tress:! et al. (1978).
102 Source Book of Flavors

bacterial (most commonly Leuconostoc sp.)
action during the last stages offermentation.
Numerous other acids are produced dur-
ing fermentation. Most microorganisms
have active lipase systems that attack trigly-
cerides to yield glycerol, monoglycerides,
diglycerides and free fatty acids. These free
fatty acids can make a substantial contribu-
tion to the flavor of various cheeses and
sausages. Secondary reactions of the free
fatty acids (e.g., oxidation) can again yield a
host of new flavor compounds.
Acids may also come from the deamina-
tion of amino acids. The products are
various aliphatic (linear and branched
chain) and aromatic acids.
Carbonyls
Carbonyl flavor compounds make a par-
ticularly significant contribution to the
flavor of fermented dairy products. Diacetyl
is one of the most important carbonyls to
the flavor of these products. It has a buttery,
nut-like flavor. Diacetyl is produced via the
fermentation of citrate in dairy products.
The most important citric acid fermenters
are Leuconostoc citrovorum, L. creamoris,
L. dextranicum, Streptococcus lactis
subspecies diacetylactis, S. thermophi/us
and certain strains of Proprionibacterium
shermani (Kempler 1983; Vedamuthu
1979). The metabolic pathway leading to
the synthesis of diacetyl is somewhat con-
troversial. Kempler and McKay (1981)
have presented a summary of the two best
accepted pathways (Fig. 3-13). Both path-
ways involve the degradation of citrate
to acetate and oxaloacetate, which is
then decarboxylated to form pyruvate.
Apparently, diacetyl is relatively nontoxic
to the bacteria cell so excess pyruvate is
channeled into diacetyl (Harvey and Collins
1963).
Unfortunately, diacetyl is not stable in
most cultured food products. The micro-

Citrate

Citrate per•ea••
+
l
Citrate

Cltrttaoo

Acetic acid +
t
Oxalaacetic acid

o....... ,.,. ............. ..

C02 + Pyruvate - - - - - -1
CoA: )............ ·vHTPP I

_,.
/ ~
Active . acetaldehyde 1
I

/ I '
~/ j ' I
. ' I
Acetyl CoA-·-·-·-·-·-·-·-·-·-.1 ' 1

CoA·IIIfHTPP HTPJ~
-r - a-
!
Dlacetyl ~ - Acetoloctlc acid

COz tCOz
2,3-Butanedlol +--- Acetoin Acetoin

FIGURE 3-13. Formation of diacetyl during fermentation in dairy cultures.

(Kempler and McKay 1981)

organisms that synthesized the diacetyl also
contain diacetyl reductase, which reduces
diacetyl to flavorless acetoin and 2,3-
butanediol. Thus, fermented products such
as buttermilk, which depend on diacetyl for
flavor, have an optimum or peak flavor.
As the product is stored, the diacetyl is
reduced, and flavor strength and quality
decrease.
A second dairy product where carbonyls
are considered as flavor impact compounds
is yogurt. Here, acetaldehyde is credited
with providing the characteristic pungent
green character. Acetaldehyde is a meta-
bolic end product of L. bulgaricus and/or
S. thermophilus during the fermentation of
milk to yogurt (Margalith 1981).
Carbonyls are quite important to the
flavor of cheeses. Maarse and Visscher
(1989) have noted that a total of 30 aldehydes
and methyl ketones have been identified
in the volatile fraction of Cheddar cheese.
Carbonyls (methyl ketones) may arise
in fermented products initially via lipase
activity of the microorganism. Dairy pro-
ducts contain a significant quantity of ~-keto
acids, which are readily hydrolyzed from the
triglyceride by microbial lipases and then
decarboxylated to form the odd carbon
number methyl ketones.
Methyl ketones and aldehydes may also
be formed via microbially induced lipid
oxidations (Haymon and Acton 1978). The
oxidation may be initiated by microbial
lipases, hydrogen peroxide produced by
microorganisms (Tjaberg et al. 1969) and/or
lipoxidase-like activity.
A final mechanism for the formation of
carbonyls via microorganisms involves the
transamination and decarboxylation of free
amino acids. Morgan (1976) has demon-
strated the production of 3-methyl butanal
by S. lactis var. maltigenes. MacLeod and
Morgan (1958) have documented the pro-
duction of 2-methyl butanal, methional
and phenylacetaldehyde from leucine,
methionine, and phenylalanine, respec-
tively, by the same microorganism.
Carbonyl compounds typically are sig-
Flavor Chemistry 103
nificant to the flavor of most fermented
food products. As has been shown, these
carbonyls may arise due to carbohydrate or
citrate metabolism, lipid oxidation or amino
acid degradation.
Alcohols
Alcohols typically make a minor contribu-
tion to flavor unless present in relatively
high concentrations (ppm) or they are
unsaturated (e.g., 1-octen-3-o1). Alcohols
may arise via primary metabolic activity
of a microorganism (e.g., ethanol) or by
reduction of a carbonyl to the corresponding
alcohol.
Reazin et al. (1970) have outlined
metabolic pathways leading to the major
congeners during grain fermentation (Fig.
3-14). This figure illustrates that the fusel
alcohols (alcohols larger in size than ethanol)
can be formed from either carbohydrate or
amino acid metabolism. Alcohol production
from amino acids may occur by transamina-
tion, decarboxylation and reduction or
by oxidative deamination followed by
decarboxylation and reduction. In either
pathway, the product is always the amino
acid minus the amine group and one carbon
atom.
The alternate metabolic pathway yielding
alcohols involves the reduction of the cor-
responding carbonyl (Fig. 3-15). Lamparsky
and Klimes (1981) demonstrated this mech-
anism by finding the equivalent alcohols (as
aldehydes) in Cheddar cheese. Secondary
alcohols corresponding to the methyl
ketones found in blue cheeses have also
been reported.
Terpenes
Currently the production of terpenes by
microorganisms is primarily of academic
interest. There are no fermented food pro-
ducts commercially available that derive
their characteristic flavor from terpenes.
The interest in terpene synthesis by micro-
organisms is due to the potential for the
104 Source Book of Flavors

Isoamyl alcohol ••---,

Acetoacetyl CoA~ Butyric acid

r---- Acetic acid

Isobutyl alcohol ••- - - - .

r/PsE-M-:~,,
',,t',,
Valine ~<==;;;-1 ',~~cetyl CoA~• Carbohydrates

Isobutyric acid • • - - - ' !~Ethyl

' ' , , _ Ethyl acetate
alcohol

~-~~,, I
d- Amyl alcohol ~
_ _ _____ --- ----:: Propionic acid •
Isoleucine ... [AKBMVA - • [AKBA}~..----------- ------!

0(- Methyl butyric acid J ._I_ _. . . n- Prooyl alcohol

FIGURE 3-14. Proposed metabolic pathways for the synthesis of whiskey

congenets. (Reazin et al1970, Copyright 1970, American Chemical Society)

Lip Ids

1
Fatty acids
Llpooa

/~-....... ..
I
Keto acyi-CoA Acyi-CoA + Acetyi-CoA

t"".., ,,,~'
', Th Ia Ia a a ,/ kc
tahydraloaa --,,, __ ,.·
-~--------

{3 -Keto acId

~·········· ~2-Aikanol

2-Aikanone Raductaaa

FIGURE 3-15. Metabolic pathways leading to the formation of methyl ketones and
the corresponding 2-alkanols. (Kinsella and Hwang 1976)

commercial production of specific terpenes as metabolic products of Ceratocystis

via fermentation (Kempler 1983; Tressl et
al. 1978; Jourdain et al. 1985; Kieslich et al.
1985; Gatfield 1986).
Collins and Halim (1970) identified
geraniol, citronellol, linalool, neral, citral,
geranyl acetate and citronellyl acetate
variospora. Later, nerol, citronellol and
geraniol were found to be produced by
Trametes odorata (Halim and Collins 1971;
Collins and Halim 1972).
The biosynthetic pathways leading to
terpene formation in microorganisms is not
 Flavor Chemistry 105

well characterized. It is assumed that a Lactones

pathway similar to that found in pla~ts als?
operates in microbial syntheses. Thts basi-
cally involves the conversion of mevalonate
(MVA) into isopentyl pyrophosphate and
3,3-dimethyl allyl pyrophosphate, which
condense to form geranyl pyrophosphate
(Banthorpe et al. 1972). ~anza an~ Pal~er
(1976) have provided evtdence vta radt?-
active labeling that this pathway occurs 1~
the synthesis of geraniol in Ceratocystzs
moniliformis.
Lactones make a significant contribution to
the flavor of several fermented food pro-
ducts, particularly dairy products and
alcoholic beverages. Tressl et al. (1978)
have summarized some of the previous
literature on lactone synthesis by micro-
organisms in fermented alcoholic beverages.
As can be seen in Fig. 3-16, lactones may be
formed from amino acids. Pathway A shows
the oxidative deamination of glutamic acid
to yield 2-oxoglutarate. The 2-oxoglutarate

(A)

/+ROH

HO~COOH

(B)

0
.... ...,
OH I OH 0 I

~COOH +
COOH
~ 1
I~
COOH
I I
NH2 -cHo L ...J

~ 0

~0
J~
VOH

-'-.~)=o
FIGURE 3-16. Formation of Iactones by microorganisms. (Tress! et al1978)
106 Source Book of Flavors
is decarboxylated to produce 4-oxobutyrate,
which is then reduced to the 4-hydroxy
butyrate. The cyclization of 4-hydroxy
butyrate yields y-butyrolactone.
Pathway B illustrates the conversion of
2-oxobutyric acid into 3-hydroxy-4,5-
dimethyl-2(5H)-furanone. This lactone has
burnt aroma and has been identified in aged
sake (Takahashi et al. 1976).
Pyrazines
Pyrazines are generally associated with non-
enzymatic browning. However, pyrazines
have also been found as a result of micro-
bial action. Bacillus subtilis was the first
organism found to produce a pyrazine
(tetramethylpyrazine; Kosuge and Kamiya
1962). Since that time, several pyrazines
(2-acetyl, dimethyl, 2-methoxy-3-ethyl,
2,5 or 2,6-diethyl-3-methyl, trimethyl,
tetramethyl and trimethylpyrazine) have
been identified in aged cheese (Sloat and
Harkes 1975; Lin 1976; Liardon et al. 1982).
The mechanism of their formation is not
clearly settled. While it has been assumed
that pyrazines were formed as the result of
enzyme catalyzed reactions, recent work by
Reps, Hammond, and Glatz (1987), Rizzi
(1988), and Rizzi (1990) has shown that
pyrazines can be formed via nonenzymatic
pathways at ambient conditions. This raises
the possibility that microorganisms are
providing low molecular weight precursors
of the pyrazines as metabolic end products,
but pyrazine formation proceeds by purely
chemical pathways.
Pyrazines have also been linked to the
generation of off-flavors in foods due to
microbial action. Pseudomonas taetrolens
has been shown to produce a musty-potato
aroma (2,5-dimethyl pyrazine and 2-
methoxy-3-isopropyl pyrazine) in milk and
other refrigerated foods (Morgan 1976).
A similar flavor defect has been found in
cheese containing Ps. mucidolens. A mutant
of Ps. taetrolens has recently been isolated,
which is of interest for the commercial pro-
duction of 2-methoxy-3-isopropyl pyrazine
(Mciver and Reineccius 1986, Cheng et al.
1991). The parent culture was found to
produce about 40 ppb of this pyrazine, while
a mutant produced by chemical treatment
produced about 15,000ppb. Since the
sensory threshold of this compound is about
0.001 ppb, 15,000 is a sufficient concentra-
tion to be of commercial significance.
Conclusions
Some of the mechanisms leading to the
formation of several classes of flavor com-
pounds via microorganisms are outlined in
this chapter. At this point, two additional
ideas should be mentioned. First, we have
only considered the formation of flavor
via metabolic activity of the living micro-
organism. Microorganisms can contribute
to flavor by leaving active enzymes in the
product following death and cell lysis. A
good example of the significance of bacterial
enzymes to flavor is in aged cheeses. This
aspect of flavor has been discussed in the
section of this chapter that dealt with cheese
flavor.
The second idea that should be brought
out in closing this section of this text is that
the flavor system in a fermenting product
is very dynamic (Schreier 1979; Haymon
and Acton 1978). One microorganism may
produce a metabolite, which initially
accumulates in the product and may make
a significant contribution to flavor. A
second organism may then reach significant
metabolic activity (population) to start
metabolizing this first metabolite. There-
fore, the flavor of the product will change.
Microorganisms may also alter flavor com-
pounds produced in the product via other
mechanisms, e.g., lipid oxidation or non-
enzymatic browning. Thus, lipid oxidation
or NEB may result in a different flavor in a
fermented product than in a nonfermented
product.
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Acadamic Press.
Yu, T.H. and Wu, C.-M. 1989. Effects of pH on
the formation of flavour compounds of dis-
rupted garlic. J. Chromatog. 462:137-145.
Yu, M.H., Olson, L.E., and Salunkhe, D.K.
1968a. Precursors of volatile components in
tomato fruit: II. Enzymatic production of
carbonyl compounds. Phytochem. 7:555.
Yu, M.H., Olson, L.E., and Salunkhe, D.K.
1968b. Precursors of volatile components
in tomato fruit: Ill. Enzymatic reaction
products. Phytochem. 7:561.
Yu, M.H., Salunkhe, D.K. and Olson, L.E.
1968c. Production of 3-methyl butanal from
L-leucine by tomato extract. Plant Cell
Physiol. 9:633.
Chapter 4
Off-Flavors in Foods
The major cause of consumer complaints to
the food industry is off-flavors (Whitfield
and Shaw 1985). These off-flavors may be
due to incidental contamination of the food
from environmental sources (e.g., air, water
or packaging materials) or may arise in
the food itself (e.g., lipid oxidation, non-
enzymatic browning or enzymatic action).
This chapter discusses some of the more
common off-flavors. A more detailed
treatment of the subject can be found in
Charalambous (1980, 1990) or Nijssen
(1991).
Environmental Contamination
Airborne Sources
The air can be a very effective means of
conveying an off-flavor (OF) to a food
product. The food products susceptible to
this type of OF are generally limited to
baked goods that are cooled open to the air
environment. While the OF may enter the
product during cooling, OF may also enter
the product once packaged. The packaging
on these products typically presents little
barrier to the transmission of volatile
organic compounds.
Often the source ofthe OF can be several
miles from the food production or storage
116
facility and yet be responsible for tainting
the food. Goldenberg and Matheson (1975)
have provided a summary of OF they have
observed in the products of Marks and
Spencer due to airborne contamination
(Table 4-1). It is of interest that in one case,
the source of contamination was as far
away as 20 miles from the food production
facility.
Airborne contamination often is exceed-
ingly difficult to identify as the source of
product contamination. This is partly due to
the fact that the OF cannot be reproduced
in the product at will for studying. This
contrasts with an OF arising from lipid
oxidation, for example, during storage of
food. The oxidized OF can be reproduced
and subjected to analysis and eventual
correction. The airborne OF may occur
randomly, depending on the production
schedule of the offending source of the OF,
wind direction and speed, production
schedule of the food processing plant, etc.
The offending chemicals also typically have
very low sensory thresholds so they are
difficult to isolate and identify by estab-
lished analytical techniques. An example is
the sensory threshold of 6-chloro-o-cresol in
biscuits (5 X 10-5 ppm). This compound
was found to contribute a disinfectant taint
(Goldenberg and Matheson 1975).

TABLE 4-1. OtT-flavors due to airborne contamination•
Food Contaminant
Biscuits Herbicides
(Chlorophenols)
Biscuits Tar
Chocolates "Aniseed taste"
Cakes "Catty off-flavor"
Wrapped bakery and Diesel oil fumes
confectionery products
Cakes, biscuits, meat
pies
Biscuits Oxidized oil
"From Goldenberg and Matheson (1975).
An examination of the compounds con-
tributed to foods by airborne contamination
in Table 4-1 shows that a variety of sources
may be involved in the production of the
OF. The most common source appears to be
a chemical manufacturing facility. The
chemical plant may be producing offensive
odorants (e.g., chlorophenols) or may
be contributing compounds that undergo
secondary reactions in foods to produce the
OF. An example of an OF contributed
directly to the food product are the chloro-
phenols (Griffiths and Land 1972). An
OF coming from secondary reactions in
food products would be the reaction of
mesityloxide (Saxby 1982) or pentoxone
(Patterson 1968a, 1969) with sulfur com-
pounds in the food to yield mercaptans with
very low sensory thresholds (0.01 ppb ).
Chloroanisoles have been found to be
responsible for musty OF in foods (Saxby
1982; Curtis et al. 1974; Engel et al. 1966;
Bemelmans and Noever deBrauw 1974;
Buser et al. 1982; Maarse et al. 1985;
Whitfield and Shaw 1985). The chloro-
anisoles in a food may arise from direct
exposure to the chloroanisoles or the ex-
posure to chlorinated phenols that later
Off-Flavors in Foods 117
Method of Transmission
Carried by wind from nearby herbicide factories (3-5
miles).
Tar boiler gave off smell through gaps left in wall.
"Aniseed-type" odors airborne from adjacent factory.
Airborne contaminant produced by interaction of ketones
and sulfur compounds in chemical factory in another
town 20 miles away.
May occur in depots, warehouses, and loading bays.
Diesel oil fumes can penetrate some types of wrapping
materials and be absorbed by foods, especially "fatty"
foods. May also be caused by forklift trucks driven by
diesel oil.
Off-flavors due to paints used in stock rooms and
production areas.
Oil used for spraying savory biscuits and other products
overheated through failure of heater thermostat. Oil
oxidized in metal tank with "fishy" off-flavor. Products
inedible.
get transformed (i.e., methylated) to the
corresponding anisoles via microbial action.
An interesting example of the latter occur-
rence is the finding of 2,3,4,6-tetrachloro-
anisole in eggs and broiler meat. It appears
that some of the timber in Britain is treated
with chlorophenols as anti-sapstain agents.
These chlorophenols were converted by
microorganisms in chicken litter to the cor-
responding chloroanisoles (Curtis et al.
1974). The chloroanisoles are somewhat
volatile and appeared to enter the chicken
via air contamination. The chicken and
eggs assumed a musty taint from the
chloroanisoles.
Other sources of airborne contamination
include paint vapors, unburned fuel in
cooking ovens and emissions from forklift
trucks and transport vehicles. These con-
taminants typically have a reasonably high
sensory threshold so that contamination
must be quite severe in order to cause an
objectionable OF.
Waterborne Sources
Large amounts of water are typically used in
most food processing operations. If this
water contains significant quantities of
118 Source Book of Flavors
components, the potential exists for the OF
to be transferred into the food being pro-
cessed. Contamination may occur by re-
constitution of the food with water prior to
processing (e.g., spray drying of cheese or
reconstitution of concentrated juices for
retail sale), washing or cooking in water, or
direct steam injection as a means of product
heating. A second means by which OF may
enter our food supply from tainted water is
via absorption by fish and shellfish.
Off-Flavors in Incoming Water Supply
Off-flavors in the water supply, as received
by a food processing plant, are most com-
monly due to microbial growth. The
two most troublesome groups of micro-
organisms are algae and Actinomycetes
(Tracy and Leonard 1980), with the algae
most commonly being the greater problem.
Algal odors are divided into two groups:
those that are caused by the green and blue-
green algae (which give an "aromatic"
defect) and those caused by diatoms and
pigmented flagellates ("grassy" or "fishy"
defects) (Maloney 1963). Under the proper
environmental conditions, algae can pro-
duce surface covering blooms in several
days. As the algae population reaches
a peak, odors described as "grassy,"
"geranium," "earthy" or "vile" occur.
As the algal bloom declines, other OF
occur. These OF may be the result of
cellular degradation yielding intracellular
metabolites, which then also degrade.
Alternatively, the OF may be due to the
growth of other micro-organisms (such as
Streptomyces) on the dead algae. If the algal
bloom dies off suddenly, decomposition
products of the algae are often worse than
the initial bloom. Bacterial growth on the
blue-green algae will yield methyl, isobutyl,
and n-butyl mercaptans as well as dimethyl
sulfide (Tracy and Leonard 1980).
Off-flavors may also enter the water
supply from pipeline-encrusting organisms.
Tracy and Leonard (1980) noted "rotten
eggs," "metallic" and "putrid" odors in
water coming from a particular section of
the Coast Range Tunnel (San Francisco
water supply). They found that iron bac-
teria, Crenothrix and Gallionella, were
using dissolved iron and manganese to grow
on the tunnel walls. As the biomass grew
large enough, it sloughed off into the water
system, where it rotted, producing an OF.
Tracy and Leonard (1980) have made
some interesting observations about OF due
to chlorination. They noted that water
chlorinated beyond its "breakpoint" has
less potential for taste and odor problems.
(The breakpoint is that amount of chlorine
at which 1 unit of applied chlorine yields
1 additional unit of free chlorine.) If water
high in ammonia or other nitrogen-con-
taining compounds is not chlorinated to the
breakpoint, a taste and odor problem can
occur due to the production of chloramine
compounds (mono and dichloramine and
nitrogen trichloride). Interestingly, most
consumer complaints of chlorine taste
results from insufficient chlorine rather
than too much. Chlorination to 0.6-0.8mg/l
destroys the chloramines and nitrogen
trichlorides that have significant flavor and
yet is below the sensory threshold of 0.8-
1.0 mg/1 for chlorine.
The tremendous potential for OF due to
chlorophenols and chloroanisoles is also
evident in the water supply. Connors (1976)
noted that wooden reservoir supports
treated with creosote have been associated
with OF even though the supports did not
actually even contact the chlorinated water.
The creosote components must have been
carried through the air to the water, reacted
with the chlorine and given off-notes.
Off-odors in the water supply have been
also traced to plastic piping. Plastic piping
may contain substances that diffuse into the
water supply, thereby tainting the water.
Alternatively, plastic piping has been shown
to permit soil contamination to enter the
water supply. Tracy and Leonard (1980)
noted a case in which gasoline leakage into
the soil reached plastic water lines, pene-
trated the lines and eventually tainted the
water.

Off-Flavors Due to In-Plant
Water Contamination
The problems mentioned thus far have been
related to OF in the normal water supply.
Water may also become contaminated in the
food processing facility. Goldenberg and
Mathesen (1975) have described three such
incidences.
The first problem was traced to chlori-
nated water being used to cool lithographed
cans. Apparently, the chlorine in the water
supply reacted with the phenol-based litho-
graph print and the tainted water was then
used for the direct heating of brines and
syrups. Any time one uses direct steam
injection for heating of a food product,
extreme care must be used to assure water
quality.
The second problem was when lignin
sulfonate was used as a boiler treatment.
While there were no significant OF from the
lignin sulfonate, reaction of phenolics in the
lignin sulfonate with chlorine in the water
formed chlorophenols. These chlorophenols
gave an OF to brines and syrups when the
boiler water was used in direct heating.
The third problem Goldenberg and
Matheson (1975) described was more poorly
defined. In this case, they were finding a
disinfectant taint in spray dried cheese
powder. Apparently, the water used to
dilute the cheese for spray drying contained
compounds that gave the defect, since
placing an activated carbon filter on the
water supply solved the problem. They did
not determine the source of this OF.
One also has to note that in-plant water
purification devices may result in OF if not
properly maintained. Neglect may permit
bacteria to accumulate in the filters pro-
ducing off-odors.
Tainting of Aquatic Animals
by Contaminated Water
Off-flavors in water may contribute taints to
fish and seafood food due to their assimila-
tion during growth. It is rather impressive
how quickly fish will pick up odors from the
water. Maligalig et al. (1975) demonstrated
Off-Flavors in Foods 119
that only 10 min. exposure of fish to 2-
pentanone or dimethyl sulfide (15 ppm in
water) will result in OF in the fish muscle.
This demonstrates, very clearly, that water
quality is absolutely essential to the pro-
duction of fish with good sensory quality.
Off-flavors in fish and seafood have been
the subject of numerous research articles
and very aptly summarized in the reviews of
Berg (1983), Whitfield and Freeman (1983),
Persson (1984), and Whitfield (1988). While
OF in fish may arise due to autoxidative
processes during storage, this discussion
will be limited to OF that arise in fish
and seafood (marine animals) only from
polluted water and the marine organism
diet.
Water pollution Contamination of the
water by petrochemicals (e.g., crude oil) is
a major source of OF in marine animals
(Whitfield 1988). Aromatic hydrocarbons,
particularly the alkylbenzenes containing
nine to ten carbons, are commonly respon-
sible for OF (Motohiro 1983). Vale et al.
(1970) and Shipton et al. (1970) reported on
a "kerosene" taint in mullet taken from the
Moreton Bay area and the Brisbane River in
Queensland, Australia. This taint appeared
in the mullet at the start of winter when they
began their migration from the southern
estuaries to the warmer waters to the north.
Areas where tainted fish were caught gen-
erally had docks, sewage outlets or heavy
industry. Volatiles isolated from the tainted
fish closely resembled kerosene hydro-
carbons suggesting water pollution was
responsible for the OF. It is of interest that
oysters and mussels have a greater tendency
to accumulate petroleum hydrocarbons than
free-swimming fish (Milan and Whelan
1978).
Pollution from paper mill effluent has
been shown to be a problem in certain
Norwegian rivers (Berg 1983). The fish
caught in rivers with paper mills were
generally badly tainted and the taint was
described as being "typically paper mill"
and "sulphite-like." Numerous compounds
were associated with this OF. Terpenes,
120 Source Book of Flavors
terpene derivatives, alkyl benzenes, alkenyl
benzenes and organochlorine compounds
were always higher in concentration in fish
characterized as having "sulphite-like" or
"paper mill" taints.
Paasivirta et al. (1983) have found
2,3,4,6-tetrachlorophenol and hexachloro-
benzene as sources of OF in fish from rivers
and lakes contaminated by processing
effluents.
Contamination of water with herbicides
and fungicides has also been implicated in
fish OF. Miyazaki et al. (1981) found that
excessive use of pentachlorophenol-based
herbicides in rice paddies has resulted in
polyhaloanisole contamination of oysters in
Tokyo Bay. It is quite evident from the
literature that there are many sources of
water contamination that can result in taints
in marine animals.
Taints Related to Diet Unfortunately,
assuring that the water is not contaminated
via oil spills or industrial pollution does not
guarantee the absence of OF in marine
animals. Other aquatic organisms, either
growing in the water or serving as food for
the marine animals, are frequently the
source of OF.
"Earthy muddy" taints occur very
commonly in marine animals. These taints
have been traced to the growth of a species
of Actinomyces in the water by Thaysen
(1936) and Thaysen and Pentelow (1936).
More recent studies have demonstrated
that blue-green algae are probably more
commonly the source of OF than the Ac-
tinomycetes (Whitfield 1988).
The OF components responsible for the
muddy defect in fish are generally geosmin
or 2-methylisoborneol (Whitfield 1988).
Recently, Martin et al. (1988) have im-
plicated two dehydration products of 2-
methylisoborneol, 2-methylenebornane, and
2-methyl-2-bornene, as additional com-
pounds which will contribute to the muddy,
musty OF in fish. All of these compounds
are known to be metabolites of certain
species of Cyanobacter (Izaguirre et al.
1982; Slater and Blok 1983; Siguira et al.
1986) and Actinomycetes (Sironen 1982;
Gerber 1983). The occurrence of 2-methyl-
isoborneol and geosmin in water has been
shown to be correlated with increasing
euthropication (Persson 1982; Juttner
1984). Warm water temperatures, high fish
standing crops and excess amounts of fish
food all contribute to the high incidence of
OF in catfish from culture ponds (Brown
and Boyd 1982; Armstrong et al. 1986).
Martin et al. (1988) studied the uptake of
2-methylisoborneol in catfish. When the fish
were placed in water containing 2-methyl-
isoborneol at a concentration of 5 J.lg/1, in
only 2 hrs the level found in the fish mus-
cle was 32 ± .2 J.lg/kg. Maximum muscle
concentration, (54 ± 4 J.lg/kg) was reached
in 48 hrs. When 2-methylisoborneol con-
centrations in the water were increased to
50 J.lg/1, muscle levels also went up by a
factor of ten. In general, the methyliso-
borneol was concentrated in the fish muscle
at a level approximately ten times that
added to the water. This reflects the par-
tition coefficient of methylisoborneol for fat
vs. water.
Martin et al. (1988) also determined
where in the catfish the methylisoborneol
was concentrated. Methylisoborneol was
found in the greatest concentration in the
subepidermal layers and abdominal fat.
While "muddy" and "musty" OF are
the most common taints found in marine
animals used as foods, a number of other
flavor defects also may occur (Johnsen
1989). Motohiro (1962) described an OF in
canned salmon that was "petroleum-like" in
character. He found that this OF was due to
the thermal degradation of dimethyl-~­
propiothetin to dimethyl sulfide. Dimethyl-
~-propiothetin was present in the salmon as
a metabolite of Limacina helicina, a major
constituent of the salmon diet. Dimethyl
sulfide was also found to be responsible
for an OF described as "blackberry" in
cod from the Labrador coast (Sipos and
Ackman 1964; Ackman et al. 1967).
Whitfield (1988) has summarized work on
two distinctive OF in Australian prawns.

The first defect was a garlic-like note found
in the red prawn, Aristeomorpha foliacea,
which was traced to trimethylarsine. The
odor threshold of trimethylarsine in water is
about 0.002 J.lg/kg and about 0.1 11g/kg in
prawns. Trimethylarsine was postulated
to arise from the microbial alkylation of
arsenic. Alkyl arsines have been isolated
from soil, sewage sludge, ocean mud and
brown algae (Whitfield 1988).
A second OF discussed by Whitfield
(1988) was an "iodoform-like" defect found
in both prawns and shrimps. This OF was
traced to the presence of 2.6-dibromo-
phenol (Whitfield et al. 1988) in the diet.
Certain local algae and bryozoa were found
to contain this compound. The sensory
threshold of this compound was determined
to be 32 J.lg/kg in prawn muscle.
One can see that water quality is im-
portant in determining flavor quality of
foods. The quality of water may influence
the flavor of marine animals, thereby pro-
viding OF to our food before the food is
even collected. Several examples have been
TABLE 4-2. Off-flavors due to disinfectants, pesticides, and detergents•
Food Contaminant
Cake Chlorophenol
Spray-dried milk Chlorophenol
powder
Canned peas Chlorophenol
Canned raspberries Pesticide
Pork Disinfectant
Tomatoes Pesticide
Smoked bacon Disinfectant
•Goldenberg and Matheson (1975).
Off-Flavors in Foods 121
discussed whereby incoming tainted water
may contaminate the food. Alternatively,
water may become contaminated in-plant.
The water may pick up various chemicals
from boiler treatments, polymeric piping or
cooking processes. Water can be a very
effective medium of transferring objec-
tionable odorants to our food supply.
Disinfectants, Pesticides, and Detergents
Disinfectants, pesticides and detergents
comprise a group of chemicals that occa-
sionally contribute to OF in foods due to
inadequate care in their application. That is,
they are present only because someone was
careless in their usage or handling. Again,
the summary of OF observed at Marks and
Spencer (Table 4-2) by Goldenberg and
Matheson (1975) provides a useful illus-
tration of how these chemicals may enter
a food and produce an OF. They noted
several incidences of OF in food due to
detergent contamination, which are not
included in Table 4-2.
Method of Transmission
Due to sultanas, contaminated on board ship by chlorophenol. On a
previous voyage, holds had been used for cargo of herbicide
containing 0.5% chlorophenol as impurity. Hold washed out, but
timber still impregnated. Finally, timber parts had to be destroyed.
"Off-flavor" of chlorophenol type: waterborne; use of activated
carbon eliminated off-flavor.
Peas transported to cannery in open steel troughs on newly tarred
road. Peas contaminated by tar-covered stones flying up from
road. Peas then blanched in chlorinated water and chlorophenol
formed.
"Catty" off-flavor may have been due to mesityl oxide in ketonic
solvent.
Preventive spraying with disinfectant in slaughterhouse against
spread of swine vesicular disease.
"Off-flavor" of chlorophenol type.
Hypochlorite used as sterilizing agent; excess used and inadequately
washed off. Chlorine combined with phenolic compounds present
in smoked bacon to give chlorophenol. Bacon uneatable.
Sterilizing agents containing chlorine should not be used where
smoked meats or fish are handled, unless special precautions are
taken.
122 Source Book of Flavors

Packaging Sources solvent, polymer, adhesive, etc.) does not

Food packaging materials are frequent
contributors to OF found in food products.
Packaging may contribute to OF by directly
contaminating the food with some con-
stituent (e.g., residual monomers in plas-
tics), allowing adhesives, printing inks or
coatings to migrate through the packaging
to the food or inadequately protecting the
food from the environment (airborne
contamination, transmission of light or
oxygen, etc.). One must be aware that
regulatory approval to use a particular food
packaging constituent (e.g., coating, ink,
imply that the material will not cause OF.
Regulatory approval relates to toxicity, not
efficacy.
Food Contamination
Virtually the only food packaging material
that will not potentially contribute an OF to
foods is glass. Since food is not sold in glass
ampoules (i.e., sealed entirely in glass)
but needs a closure of some type, a small
potential exists for food contamination due
to this closure even for glass packaging.
Some occurrences of food contamination

TABLE 4-3. Off-flavors in foods due to packaging materials

Food Packaging Material Source and Method of Transmission

Paper
Cakes, biscuits, Chipboard Off-flavor due to either preservatives added to repulped
chocolate• waste paper or compounds in print in waste paper.
Doughnutsb Coated paper divider Inadequate removal of hydrocarbon solvent used to apply
plus cellophane divider coating.
Cold cereals< Glassine coupons Residual solvents in inks.
Chocolate cakes• Coated paper Inadequate "curing" of inks used in printing.
Yogurt containersb
Confectionery•
Plastic
Orange and lemon PVC bottle Mercaptide stabilizer used in PVC-split off in processing
drinks" of beverage.
Chocolate and Polystyrene trays Residual styrene printed monomer.
Iemond cookies wrapped in
cellophane
TV dinnersb Polystyrene trays Residual styrene monomer.
Laminates
Fruity soft drinksd Polyester /aluminum Residual toluene in laminate adhesive-faulty drying
foil/polyethylene process.
laminate
Metal-Paper
Refrigerated doughsb Paper tube with Residual hydrocarbon solvents in triglycerides used to
metal caps lubricate metal caps to facilitate packaging operation.
Metal
Canned pork Lacquered can "Catty" OF due to use of lacquer to cover sideseam to
products• prevent blackening. Solvent used contained mesityl oxide,
which reacted with sulfur compounds in food to cause
OF.
Refrigerated milkb Lacquered can Trace contaminant (isophorone) in solvents used in
beverage lacquer, which did not "flash off."
Beer Can Lubricants used in can manufacture.
"Goldenberg and Matheson 1975. bG.A. Reineccius 1983, unpublished. 'Heydanek 1977; Heydanek et al. 1979. dPassey 1983.
• Hardwick 1985.

by packaging materials and resulting in
OF are presented in Table 4-3. The con-
tamination seldom comes from the major
packaging component. Most often the OF is
due to trace amounts of residual solvents in
the packaging material. This may be related
to the production of the packaging material
(e.g., styrene monomer), trace contami-
nants in the packaging material (e.g., ethyl
benzene in plastics or residual ink solvents
in recycled paper), solvents used in inks to
print on the food package or solvents in
adhesives. In some cases, the contaminant
responsible for the OF is a normal con-
stituent of the packaging system, but has not
been adequately removed by the processing.
This typically occurs due to "pushing"
production too fast. The alternative is that
the solvents may, on occasion, be contami-
nated with higher boiling constituents that
are not removed by established process
conditions.
A quick review of Table 4-3 indicates
that virtually all food packaging materials
(except glass) may contribute an OF to food
products. However, OF due to packaging
materials should be controllable by an
adequate quality control program. The OF
arising from packaging materials are nearly
always due to volatile constituents occurring
in the packaging material at reasonably high
concentrations. High concentrations are
necessary since the weight of packaging
material to product is typically quite low.
Therefore, the volatile OF constituents
usually are in the packaging material at
sufficiently high levels to be monitored
by established quality control methods
(Heydanek 1978).
Flavor Scalping
Flavor migration (scalping) into the plastic
packaging is also a concern (Hotchkiss
1988). There are some plastic packaging
materials that are very "clean" in terms
of providing malodorous compounds to
foods (e.g., polyethylene). However, these
plastics may well be guilty of scalping flavor
from a food product, thereby reducing
Off-Flavors in Foods 123
overall flavor strength or selectively ab-
sorbing only certain flavor constituents
resulting in a change in flavor character
(Hotckiss 1988). Polymers used as coatings
on the inside of metal cans, jar closures,
barriers for paperboard or the container
itself (i.e., plastic bottles or aseptic pack-
ages) may be responsible for flavor scalping.
Obviously, the larger the surface area and
mass of the polymer, the faster the rate and
the greater the quantity of flavor absorbed
from the food. When the polymer is the only
packaging material, the opportunity exists
for the flavor to migrate into and through
the polymer. While one finds quite different
concerns for this situation vs. simple ab-
sorption, the two will not be differentiated
for this discussion. If some or all of the
flavor leaves the product, there may well be
flavor problems.
Scalping is seldom uniform, i.e., the
polymer will typically offer greater solubility
to some flavor components than others. If
the greater solubility is for flavor impact
compounds (i.e., those that carry the
characteristic flavor), the named flavor
decreases in intensity with storage. If
greater solubility is for supportive com-
pounds, the flavor may change in character.
Thus, the problem encountered due to
scalping may be a general change in flavor
intensity or an imbalancing due to selective
absorption.
Model Systems While there is sub-
stantial literature in the area of flavor
scalping (Hotchkiss 1988), only a couple of
studies will be presented to illustrate the
problem. Most studies have involved model
systems whereby the absorption of selected
compounds by various polymers or per-
meability of polymers to flavorants was
monitored. When absorption is considered,
rate of flavor loss is determined by both
solubility and diffusion factors. If the
flavor compound has little solubility in the
polymer, it will not enter the polymer and
thus not be lost from the food. If the flavor
compound is soluble in the polymer, then its
124 Source Book of Flavors
rate of loss from the food depends upon
diffusion rate through the polymer. We can
readily see that properties of the flavor
compound (e.g., polarity and molecular
size) as well as polymer properties (e.g.,
chemical composition, density and thick-
ness) will influence flavor loss. Specific data
to illustrate these factors are presented
below.
Landois-Garza and Hotchkiss (1988)
studied the effects of molecular weight,
relative humidity and concentration on the
permeability of polyvinyl alcohol (PVOH)
films to alkyl esters. They found film per-
meability to increase with increased mole-
cular weight of alkyl esters. Increased
molecular weight resulted in greater
solubility and this factor was more impor-
tant than the decreased diffusion rate in
controlling permeability. Larger molecular
weight esters would be preferentially lost
from the food, thereby changing flavor
profile and sensory character.
Concentration and humidity were also
found to influence film permeability. As
concentration of flavor compound in-
creased, permeability increased. Perme-
ability of PVOH was found to be directly
related to humidity.
A rather comprehensive treatment of the
-,
10
z 1
..........
E
0. 1
D..
0.01
-
0 •-•
o.oo 10
FIGURE 4-1.
odor permeability of polypropylene has
been provided by Zorbel (1985). A sum-
mary figure (Fig. 4-1) has been selected
from their work. As can be seen from this
figure, molecular weight and chemical prop-
erties (primarily polarity) are important
determinants of permeability of flavorants.
Within a given class of flavor compounds,
permeability is reasonably predictable.
Food Systems An alternate approach to
working with model systems has been to
place real foods in various packages, and
monitor flavor analytically and sensorially.
Many studies have been conducted using
citrus products, since they are particularly
prone to flavor scalping problems and are
commonly packaged in aseptic containers
(have polymer food contact surfaces).
Mannheim et al. (1987, 1988) reported on
changes in limonene content and sensory
properties of citrus juices packaged in glass
jars vs. a laminated carton of polyethylene/
carton/aluminum/polyethylene. Limonene
losses were greater during storage in the
laminated package than the glass jars. This
loss translated directly to flavor changes
detectable by a sensory panel. Sensory
differences between glass and laminate
packaged orange juice were significant
C10c:~..: ACETATE
GUAIACOL- f/_'E -
WATER /' ...WENTHOL • ALKANES
X _C5 °1 UWONENE
XYLE;zNE 0 ESTERS
\ C2 /I X ALCOHOLS
C1-+X Ct ,o - AROWAncs
\ o,.._
C2..,.X 1._ '"'2-BUTANONE 1 WISC
TEl'JWM)ROf'URAN
""'-
c2. C3 ~Cs"'PROPANAL
--------
C1 C3
50 100 150 200
MOLECULAR WEIGHT
Odor permeability of polypropylene. (Zobel1985)

after about 9 weeks of storage. Grapefruit
juice stored in glass and that stored in the
laminated carton were not significantly
different until about 12 weeks of storage.
Packaging Catalyzed Off-Flavors
A second and perhaps important effect of
polymer coatings is their cataytic effect on
flavor deterioration. Mannheim et al. (1988)
demonstrated this effect by placing strips
of carton laminates in juices stored in
hermetically sealed glass jars. Surface to
volume ratios of 1 : 4 and 1 : 6, as compared
with the actual ratio in 1-liter packs, were
used. The contact of orange juice with
laminated carton resulted in accelerated
ascorbic acid loss and browning relative to
controls stored in all glass. It was noted
that sensory panels could detect flavor
differences between juices in contact with
laminates vs. glass in as little as 14 days'
storage.
Oxygen/Water Vapor Transmission
A final consideration of plastic packaging
relates to its relative oxygen or water vapor
transmission rates. It is reasonable that
oxidation rate is influenced by availability of
oxygen. Plastic packaging materials vary
greatly in oxygen permeability and in all
cases, exceed that of the glass or cans the
plastic often replaces. Thus flavor quality
may deteriorate rapidly in plastic packaging
due to oxidation.
Water vapor transmission through a
package can also influence flavor quality.
The obvious effect is a loss in crispness of
products such as potato chips. Less obvious
is the influence water activity has upon
chemical reactions in foods. It is well docu-
mented that many deterioration reactions in
foods are influenced by water activity and,
therefore, perhaps packaging materials.
Off-Flavors Due to Genetics or Diet
It is obvious to each of us that genetics and
diet have a strong influence on the flavor of
Off-Flavors in Foods 125
both plants and animals. We appreciate the
differences in flavor found between the
numerous varieties of apples, grapes, etc.
We do not, however, accept differences in
meat flavor due to either genetics or diet.
We have come to expect all meats (of the
same species) to taste the same. If a steak
tastes different, we consider it to have an
OF.
Genetics
Two animal species in which genetics plays
an important role in producing an OF are
swine and ovine. Swine products (pork)
occasionally contain an OF characterized as
being perspiration or onion-like (Lerche
1936). This OF occurs primarily in sexually
mature uncastrated hogs. It is of interest
that 46 percent of the male population and
92 percent of the female population can
smell this off-odor (Griffiths and Patterson
1970). The OF is believed to be caused by
5-a-androst-16-ene-3-one and skatole (Bon-
neau 1982).
Like swine, the mature ovine animal is
also considered to have an OF. This OF is
called mutton flavor and is characterized as
being "sweaty-sour" in nature (Wong 1975).
The source of this OF has been traced to the
synthesis of 4-methyl octanoic and 4-methyl
nonanoic acids in the mature animal (Wong
et al. 1975).
Diet
Animal diet can have a pronounced in-
fluence on the flavor quality of meats,
especially in the nonruminant species.
Bemelmans and Noever deBrauw (1974)
found chloroanisoles in poultry feed to
give a musty note to broiler meat. Off-
flavor may also enter poultry meat via the
diet from the consumption of significant
levels (>2 percent) of highly unsaturated
fats (Crawford et al. 1975). For example,
turkeys fed 2 percent tuna oil develop a
"fishy" OF when cooked (Crawford and
Kretsch 1976a,b). The fishy character was
found to be due to oxidation of the highly
unsaturated fatty acids during cooking of
126 Source Book of Flavors
the turkey. Poultry very readily deposit
dietary fat. Goldenberg and Matheson
(1975) reported similar OF problems
with the feeding of fish oil to hogs. They
recommended limiting fish oil to less than
1 percent of the animal diet.
Off-flavors entering fish via the diet have
already been partially discussed in this
chapter. Mention was made of "muddy"
taints being the result of the fish eating
certain algae (Anabaena, Ceratium, and
Pediestrum). Petroleum-like OF have been
found in fish consuming Limacina helicina
as a major part of their diet (Motohiro
1962). Earthy taints have been associated
with the consumption of certain Actino-
myces species (Thaysen 1936). In addition
to OF arising in fish from certain algae in
their diet, OF may also occur if the fish are
fed turkey livers or cereal. Maligalig et al.
(1973) found turkey liver notes in pond-
reared catfish after 19 days of feeding livers
and cereal notes in the fish following 33
days on a cereal diet. It appears that the
maintenance of flavor in fish farming is a
challenging task.
There are numerous studies showing how
diet can produce OF in lamb (Reineccius
1979). Park et al. (1972a) reported on a
"sickly" and "nauseating" aroma in lamb
that had been fed rape. They postulated that
the natural glucosinolates of the rape were
metabolized to aliphatic sulfides, disulfides
or mercaptans, which caused the OF. Park
et al. (1972b) also noted that feeding vetch
had an influence on lamb flavor. The vetch-
fed lambs had a sweeter and stronger meat
flavor.
Off-Flavors Due to Chemical
Changes In The Food
Foods contain a number of constituents
that may either react with other food con-
stituents or simply degrade to produce OF
components. The major reactions leading to
OF include lipid oxidation, nonenzymatic
browning, enzymatic action and photo-
catalyzed reactions. This chapter will
present some examples arising in foods from
these reactions.
Lipid Oxidation
Lipid oxidation is, with few exceptions
(e.g., American milk chocolate and deep fat
fried flavor), a detrimental reaction. This
reaction is probably the most common one
leading to OF in foods during storage.
While dry foods are most susceptible to OF
from lipid oxidation, nearly all foods are
susceptible to deterioration via this reac-
tion. Frankel (1985) has presented a review
of the chemistry of lipid oxidation and
Grosch (1982) a review of lipid oxidation as
it relates to OF production. The review of
Grosch (1982) is an exceptionally well-done
offering directly related to the subject
matter, and is highly recommended to the
reader for detail beyond what is presented
here.
Lipid oxidation (LO) typically involves
the reaction of molecular oxygen with un-
saturated fatty acids via a free radical mech-
anism. The mechanism may be presented as
follows:
fast
R. + 0 2 -----~ROO.
~----
slow
ROO. + RH '1 ~ ROOH
ROOH ~ flavor and nonvolatiles
where RH is unsaturated lipid; R a lipid
radical; and ROO a lipid peroxy radical.
One can see that this is a self-propagating
reaction, i.e., once started, it continues
itself. It is interesting that an initial radical
will produce about 100 hydroperoxides
before its termination occurs (Bolland and
Gee 1946). Lipid hydroperoxides are very
unstable and break down to produce shorter
chain volatile flavor compounds. These
primary reaction products can undergo
further oxidation if unsaturated, or sec-
ondary reactions to yield a host of OF
volatiles. These final products are generally

aldehydes, ketones, acids, alcohols, hydro-
carbons, lactones, or esters. The unsaturated
aldehydes and ketones have the lowest
sensory thresholds and are, therefore, most
often credited with being responsible for
oxidized flavors. The metallic taint in
oxidized butter, for example, has been
attributed to oct-1-ene-3-one (Stark and
Forss 1962).
An insight into the factors that enhance
lipid oxidation will help one understand why
different food products develop oxidized
OF. The number and type of double bonds
in a fatty acid have a strong influence on rate
of LO. Fatty acids containing three or more
double bonds are extremely prone to oxi-
dation. In some food applications (e.g.,
dehydrated coffee whiteners), the linolenic
acid must be selectively hydrogenated in
order to permit an acceptable shelf life. The
presence of any linolenic acid in the coffee
whitener would limit shelf life to probably
less than 3 months.
Trace metals, particularly copper, cobalt
and iron, greatly increase the rate of LO and
influence the direction of peroxide decom-
position (Love 1985). These metals function
both to reduce the induction period and
increase reaction rate by decomposing the
hydroperoxides. As little as 0.3 ppm iron or
0.01 ppm copper will result in oxidized OF
in soybean oil (Dutton et al. 1948). The iron
may also come from heme in meats. This
aspect of metal catalysis will be discussed in
connection with warmed-over OF in meats.
There is substantial literature indicating a
strong relationship between water activity
and rate of LO (Labuza 1971). Very dry
products (below the monolayer) or inter-
mediate moisture products are very sus-
ceptible to LO. Dry foods, such as dry milk,
potatoes, potato chips and dry cereals, are
particularly susceptible to LO because they
have substantial area for oxygen exposure,
are permeable to oxygen and may be at
water activities (less than the monolayer) so
that oxidation rate is high.
Lipid oxidation rate is temperature
dependent. While LO may be initiated by
Off-Flavors in Foods 127
enzymes (e.g., lipoxygenase), it most often
is a "pure" chemical reaction responding to
reaction temperature. The higher the
temperature, the faster the rate of LO. As
will be discussed later, light is an effective
initiator of LO. The shorter wavelengths are
higher in energy and, therefore, are more
effective in enhancing the rate of LO.
A final factor determining rate of LO is
the presence of antioxidants (Houlihan
and Ho, 1985; Sherwin 1985). Most of the
vegetable oils contain some tocopherols,
which are quite effective antioxidants. The
amount of natural (or added synthetic)
antioxidant will influence rate of LO.
If one considers the factors that influence
rate of LO, one can see that very dry pro-
ducts high in polyunsaturated fatty acids
are most likely to develop OF due to LO.
However, one must also recognize that
virtually all foods contain sufficient lipid to
develop OF via LO. It is only a question of
whether some other mode of product failure
occurs before LO becomes significant. It is a
question of time.
While we usually think of LO in terms of
dry milk, breakfast cereals and snacks,
occasionally, we do find fish and meats
developing OF due to oxidation. Fish are
very susceptible due to their very highly
unsaturated fatty acids. Mendenhall (1972)
reported significant oxidation in fresh mullet
and bluefish after 3 and 5 days storage,
respectively. However, most fresh fish spoil
via microbiological means before oxidation
becomes significant. Frozen fish have a
sufficiently long shelf life, so that oxidation
becomes the major mode of deterioration.
While other meats are not nearly as sus-
ceptible to oxidation, one occasionally finds
oxidized frozen meats, particularly those
imported from foreign countries where the
meat has been stored for several months
during shipping, etc.
It should be mentioned that foods con-
taining carotenoids also undergo oxidative
deterioration. Carotenoids contain two end
groups (often cyclic) joined by a series
of conjugated trans double bonds. The
128 Source Book of Flavors
oxidation of carotenoids yields highly
unsaturated compounds plus cyclic deriva-
tives of the carotenoids. Ayers et al. (1964)
were the first to identify alpha-ionone, beta-
ionone and beta-ionone-5,6-epoxide as OF
components of dehydrated carrots. The
ionones have a floral character and are
typically used in the formulation of rasp-
berry flavorings. If dehydrated yellow or red
vegetables (containing carotenoids) are to
be used in a food product, an antioxidant
must be used to provide adequate shelf life.
Off-flavors occur due to oxidation of the
carotenoids in products such as dry carrot
cake mixes and foods containing dehydrated
tomato products.
It is also interesting that frozen tomato
products, e.g., pizza, will undergo sub-
stantial carotenoid deterioration during the
average distribution and storage system. It
is, in fact, carotenoid deterioration that
typically limits the shelf life of frozen pizzas.
Warmed-over flavor (WOF) is an OF
associated with precooked meats (Tims and
Watts 1958). This OF is generally accepted
as being due to the oxidation of intramus-
cular phospholipid fatty acids. Oxidation
proceeds at a very rapid rate following
heating of the meat due to denaturation of
heme proteins and destruction of cellular
structure, thereby permitting intimate
mixing of cellular constituents. While the
reaction is probably catalyzed by both heme
and nonheme iron, the nonheme iron is
considered to be of greater importance.
WOF can be inhibited by the same methods
that are used for lipid oxidation. This in-
cludes the use of metal chelators, primary
and secondary antioxidants, vacuum pack-
aging, etc. This subject has been reviewed
in detail by Asghar et al. (1988) and
Younathan (1986).
Nonenzymatic Browning
While nonenzymatic browning (NEB) is
very important to the production of desir-
able flavors, it is also a primary source of
undesirable flavors in foods. Whether one
wishes to say that canned peas have an OF
due to the thermal processing is a matter of
semantics. Canned foods do not taste like
their fresh counterparts. The primary
reason for a flavor change is NEB, which
occurs during the canning process. Virtually
any food product that undergoes substantial
heat treatment develops a flavor from NEB.
It is somewhat interesting that the
browning reaction which occurs during
storage is undesirable, while that which
occurs during heating (e.g., toasting of
cereal) is desirable. Why is it that a loaf of
bread does not get a better flavor as it is
stored? Browning is occurring in the bread
during storage and browning produced
much of the characteristic flavor of the
bread. The reason, of course, goes back to
reaction kinetics. The NEB reaction is ex-
ceedingly complex with a host of possible
pathways. The particular pathways active
during NEB depend on many factors, in-
cluding water activity, reactants present,
temperature and pH. The primary differ-
ence between developing desirable flavors
via NEB as contrasted to developing OF
during storage is temperature. At storage
temperatures, the reactions leading to
toasted, roasted, nutty and meaty flavor
compounds are not favored and, therefore,
these notes disappear from the product
during storage. Unfortunately, the NEB
pathways leading to stale, sour green sulfury
notes can and do progress at typical storage
temperatures. Therefore, OFs develop in
foods during storage due to NEB. Like lipid
oxidation, nearly all foods have sufficient
reactants (reducing sugars and amino acids)
for NEB to occur, so NEB will result in an
OF unless some other mode of deterioration
occurs before NEB becomes significant.
The OF due to NEB are most typically
characterized as being "stale" in character.
Stale is one of the more nebulous terms
used in sensory evaluation. Stale is a
rather nondescript term denoting a lack
of fresh character. Benzothiazole and
0-aminoacetophenone are two compounds
believed to be formed via NEB, and which
contribute to stale flavor. These compounds
 Off-Flavors in Foods 129

were found in stale, dry milk by Parks et al.
(1964). The 0-aminoacetophenone along
with some furans were also found to be
partially responsible for the "gluey" flavor
of old casein (Ramshaw and Dunstone
1969). 0
sulfur compounds (thiols, sulfides, disulfides
and 3-methylthiopropanal) make t~e~
primarily responsible for the charactenshc
odor of activated flavor in milk.

Beer and Champagne

While OFs due to NEB are qmte com-
Off-flavors due to light exposure have also
mon few studies other than those noted
have' been successful in identifying the been reported in champagne (Charpentier
and Maujean 1981) and beer (Kuroiwa and
components responsible for NEB staleness.
Hashimoto 1961). Tressl et al. (1980) and
Andrews (1987) have provided reviews of
Photo-Induced Off-Flavors
the "sunstruck" flavor in beer (as well as
Some unique OF may be produced via
other OF in this beverage). Like dairy
photo-catalyzed reactions in foods. "Skun-
products, the photo-induced changes in
kiness" in beer and "burnt feathers" in
beer flavor are complex, involving photo-
dairy products are two of the unique ex-
oxidation of lipids, photo-catalyzed decar-
amples of OF in foods due to light exposure.
boxylation and deamination of amino acids
and hydrolysis of the isohumulones. Upon
Milk
light exposure, beer will take on an initial
Light-induced (activated) OF in m~lk are
OF often characterized as being "skunky."
again becoming more common m the
This skunky OF is attributed to the photo-
United States. The OF due to light ex-
catalyzed degradation of the isohumulones
posure at one time was very common. Milk
(Hashimoto 1976). The4-methyl-3-pentenoyl
was bottled in clear bottles and left on home
side chain of isohumulone is cleaved to yield
doorsteps exposed to light. Changes _in
2,7-dimethyl-2,6-octadiene and 4-methyl-2-
packaging (plastic-coated paper) ~n? dis-
pentenal as major end products. In the p~e­
tribution (supermarkets) nearly ehmmated
sence of cysteine, 3-methyl-2-butene-1-thwl
this problem for several years. A recent
(prenyl mercaptan) is formed via free radical
change in packaging to clear or translucent
mechanisms. The prenyl mercaptan has a
plastic packages and brightly_ illumina_ted
sensory threshold of 0.005 ppb in water and
dairy display cases has resulted m the revival
0.05 ppb in beer. This mercaptan is respon-
of this OF. Activated OFs in dairy products
sible for the skunky OF.
are actually due to two concurrent chemical
Control of this OF is typically accomp-
reactions in the milk: lipid oxidation and
lished by packaging the beer in light im-
protein (amino acid-peptid~) degradat~on
permeable bottles or cans. The alternative is
(Dimick 1982). Amino acid degradation
to use hops that have had the iso-a-acids
produces an OF characterized as being
(isohumulones) reduced to their saturated
"cabbagy ," "burnt protein" or "burnt
counterparts. Reduced a-acids will not
feathers" in nature. Lipid oxidation pro-
form the objectionable thiols. They will,
duces rather typical cardboard and then
however, still undergo photo-catalyzed
metallic notes. The activated flavor initially
cleavage into "green" OF and result in a
predominates (2-3 days); however, card-
somewhat less objectionable OF (Tressl
boardy/metallic notes dominate later and
et al. 1980).
the milk would be judged as "typically
oxidized" after a few days of exposure.
Amino acid degradation is light-activated Enzymatic Flavor Changes
and riboflavin-catalyzed. While all of the One must remember that all foods were
amino acids undergo this degradation, the once living tissues. These tissues depended
extremely low sensory thresholds of the on enzymes for metabolism and subsequent
130 Source Book of Flavors
growth. Therefore, foods contain a variety
of enzymes. While many are inactivated by
processing or inactive due to inadequate
conditions for functioning (e.g., low water
activity, temperature, and/or pH), some
foods contain active enzymes that may cause
OF to develop in the food product. The
three enzymes most commonly associated
with OF in foods are lipoxygenase, lipase
and various proteases.
Lipoxygenase
Lipoxygenase is an enzyme that will attack
cis-cis double bonded, methylene inter-
rupted fatty acids (Gardner 1989). This
enzyme initiates lipid oxidation by ab-
stracting a hydrogen radical from the fatty
acid. Once lipid oxidation has been initiated
by this enzyme, the process of oxidation
follows the typical auto-oxidative process
leading to OF, which has been previously
described in this chapter.
Lipoxygenase enzymes are quite common
to plant tissues. The legumes (especially
soybeans) contain substantial quantities of
lipoxygenase enzymes. The beany flavor of
soybeans is believed to be due to lipoxy-
genase activity in the bean once tissue
damage has occurred (Rackis et al. 1972;
Sessa and Rackis 1977). The reversion
flavor of soybean oil is also believed to be
due to lipoxygenase activity in the oil. Hsieh
et al. (1981) have shown 2-pentyl furan to be
the oxidation product responsible for this
OF.
Lipoxygenase also plays a role in the
deterioration of frozen vegetables. Many
vegetables must be blanched prior to frozen
storage in order to inactivate lipoxygenase
enzymes that otherwise result in oxidized
OF (Whitfield and Shipton 1966).
Lipase
Off-flavors may arise from lipase activity
in foods. Lipolyzed flavor is due to the
hydrolysis of fatty acids from triglycerides.
Since lipase occurs quite widely in food
products, one would expect to find lipolyzed
OF more commonly than encountered.
The major reason lipolyzed OF is not
encountered more frequently is that most
lipids in foods contain only mid- to long-
chain fatty acids. These fatty acids (> 12
carbons) are too large to make a significant
contribution to either odor or taste. There-
fore, the only foods where lipolysis pro-
duces significant OF are those that contain
short chain fatty acids (e.g., dairy or tropical
oils such as coconut).
The OF arising from lipase activity in
dairy products is characterized as being
"butyric," "goaty," and/or "bitter" in
nature (Shipe 1980). There appear to be two
lipases in dairy products: one associated
with the fat globule membrane and the
other with the proteins. While the point is
controversial, it seems that these two lipases
are identical, but occur associated with
different constituents of the milk. Milk
lipases are highly specific for the primary
positions of the triglyceride. Unfortunately,
nature has also shown a preference to put
the most sensorially significant fatty acids
(i.e., butyric and caproic acids) in the
primary positions.
The lipases of milk are rather unique in
that they are inactive until activated by
some treatment (the exception being rare
that a cow will produce spontaneously
rancid milk). Activation of the lipase
enzyme system may be accomplished in
several different ways. Occasionally, fluc-
tuations in temperature such as cooling,
warming and then cooling, will cause the
lipase to become active. Mechanical agita-
tion or foaming can also activate the lipase
systems. This was a particular problem
when pipeline milking systems were initially
introduced. Homogenization of raw milk is
especially effective in producing lipolyzed
flavor. In a matter of seconds, the milk will
become so acidic it will nearly burn the
mouth. The milk fat globule membrane is
inadequate to cover the new surface gen-
erated upon homogenization of the milk.
This unprotected fat is particularly sus-
ceptible to lipase attack.
It is of interest that lipase activity can

be influenced by the presence of certain
chemicals (Chandran and Shahani 1964).
Aureomycin, penicillin, streptomycin and
terramycin were shown to provide 7.6-49.8
percent inhibition of lipase.
While dairy products may become
lipolyzed due to indigenous enzymes, the
lipases may also be from outside sources.
Bacterial activity, spices and some fruits
contain lipases that may attack the trigly-
cerides of milk.
The other foods subject to lipolyzed OF
are those containing tropical oils, e.g.,
coconut. Coconut contains lauric acid (C 12 )
as a major fatty acid that tastes soapy when
hydrolyzed from the triglyceride. While
coconut does not contain a significant
amount of lipases, coconut is often used in
foods with other ingredients which do con-
tribute lipases. It should be mentioned that
lipases are reasonably heat stable enzymes.
They will often survive a thermal treatment
that one would expect to be adequate to
denature the lipase.
One food product where "soapy" flavors
are a problem is the pina colada beverage.
Pina colada is an alcoholic drink based on
coconut and pineapple juice. The pineapple
is an excellent source of quite heat-stable
lipases. If one encounters a "soapy" OF in a
food product, the first step would be to
search the ingredients for coconut oil and
then a source of enzyme.
Proteolytic Enzymes
Bitterness in foods is an additional OF that
may occur due to enzyme activity. In this
case, we are considering bitterness arising
from proteolytic activity on food proteins.
Murry and Baker (1952) are often credited
with being the first to determine that this
bitterness was due to short chain peptides.
Bitter peptides have been found to pro-
duce OF in soy products (Fujimaki et al.
1968; Noguchi et al. 1970; Arai et al. 1970).
Arai (1980) pointed out that most of these
peptides have leucine at the C-terminal end.
Otherwise there appears to be little simi-
larity between peptide structures. Zein
Off-Flavors in Foods 131
(Wieser and Belitz 1975); casein (Matoba
et al. 1969, 1970; Clegg et al. 1974; Huber
and Klostermeyer 1974); and Cheddar
cheese (Hamilton and Hill 1974) have also
been found to develop bitterness due to
peptides.
Probably the largest amount of work on
bitterness due to peptides has focused on
aged cheeses (Dulley and Kitchen 1972;
Harwalkar and Elliott 1971; Emmons et al.
1962; Harwalkar 1972; Richardson and
Creamer 1973). Proteolytic activity in the
cheese comes from the rennin, starter
organisms and/or contaminating micro-
organisms. Rennin initially breaks down a
portion of the protein into large peptides.
These peptides then are further degraded
into small peptides, which may cause bitter-
ness unless they are further metabolized by
the starter organisms (Lawrence et al.
1978). Therefore, starter failure or retar-
dation via chemicals or contaminating
organisms may end up causing bitterness in
the cheese. The proper starter organisms
and their growth is essential to minimize the
possibility of bitterness during aging of
cheese (Sullivan et al. 1973).
Microbial Off-Flavors
Microorganisms (MO) are a common source
of OF in foods. If the product is not sterile
(via heating or irradiation) or preserved
via antimicrobial agents (e.g., humectants
or chemical preservatives), microorganisms
may grow in the product and produce OF.
Off-flavors may arise in food products via
microbial sources in several different ways.
The OF may be the result of a planned
fermentation going wrong. The fermented
product may then develop an OF. An
example of this would be a starter culture
failure in a cheese vat. Failure of the starter
culture would result in poor acid production
and the opportunity for the growth of other
organisms. These contaminating organisms
often result in bitterness and unclean OF.
This type of OF is possible in virtually all
types of fermented foods. Only through
132 Source Book of Flavors
very careful handling of the starter cultures
and manufacture of the fermented products
can this problem be minimized.
A second way in which microorganisms
may produce OF in foods is somewhat
indirect. Enzymes from lysed MO can
catalyze reactions in foods leading to OF.
Microbial enzymes are frequently quite
stable to heat denaturation. Therefore, a
thermal process may kill the MO but leave
active enzymes (e.g., lipases or proteases),
which can produce OF (Shipe 1980; Tressl
et al. 1980). One can appreciate that a food
may develop an OF in this manner, but yet
show very low viable cell counts. The low
viable cell count could mislead the inves-
tigator into believing that the OF was not
due to MO.
The final means by which MO can pro-
duce OF in foods is the most common. That
is from growth in the food and contamina-
tion with primary or secondary metabolic
products. Fresh fish (Reineccius 1979) and
dairy products (Shipe 1980) are two foods
that are very susceptible to OF from micro-
bial sources. Fresh fish is generally con-
sidered to have very little odor. However, if
fish is stored above freezing temperatures,
the fish develops a "fishy" OF initially,
which later becomes putrid and foul in
character. Fish is particularly susceptible to
microbial growth since the fish muscle has
substantial soluble material and cells tend to
lyse once the fish has been killed. The fish
muscle provides a rather ideal growth
medium for MO.
The "fishy" OF is primarily due to the
generation of trimethylamine via bacterial
action (Davies and Gill1936; Stansby 1962).
Trimethylamine is formed from trimethyl-
amine oxide, which is a natural constituent
of fish muscle. This reduction is accomp-
lished through bacterial enzymes and in-
volves a coupled oxidation of lactic acid to
acetic acid and C02 (Watson 1939). The
latter stages of fish spoilage involve the
production of various nitrogen- and sulfur-
containing compounds. These compounds
produce putrid sulfury notes in the fish.
It should be noted that different MO vary
in their ability to produce OF in foods. The
ability to produce an OF is dependent upon
the metabolites produced and excreted into
the growth medium (food) by the MO.
Work on OF in fish demonstrated this very
nicely. Herbert and Shewan (1976) have
shown that gram-negative bacteria of the
genera Pseudomonas, Achromobacter, and
Vibrio are most often responsible for OF in
fresh fish. Within these genera, only a few
species can cause spoilage odors. Adams et
al. (1964) found that typically less than 10
percent of the bacterial population present
on fish can cause OF. This should make one
cautious in concluding that high plate counts
(or the converse) necessarily mean an OF
came from microbial sources. It is the
specific organisms and populations that are
significant in determining the contribution
to OF.
Shipe (1980) and Badings (1991) have
reviewed some of the OF which may occur
in milk due to MO. Prior to wide usage of
pasteurization and refrigeration, milk would
most commonly spoil due to Streptococcus
lactis growth. This would result in an acid/
sour OF. Pasteurization quite effectively
kills S. lactis and their growth is not favored
by storage at refrigeration temperatures so
this organism (and OF character) is no
longer a common means of spoilage.
Today, the psychrotrophic bacteria are
typically responsible for OF in milk. These
MO can multiply at or below 7°C so they
will grow at typical refrigeration tempera-
tures. Even though pasteurization destroys
these MO, they do produce substantial
quantities of heat-stable lipases and pro-
teases that may produce OF later during
storage. They also are common postpas-
teurization contaminants that will grow in
the milk and produce OF due to metabolic
activity. The OF arising from psychrotro-
phic bacteria are often characterized as
being unclean, foreign, fermented or bitter.
Two quite characteristic OF found
occasionally in milk are fruity and malty
OF. Fruity defects have been traced to the

TABLE 4-4. OtT-flavors due to microbial spoilage: bakery products
Food Type of Spoilage
Cakes Bacteria
Cakes: angel cakes; Molds
apple tarts; marzipan
Cakes Lipolytic bacteria
Apricot jam Bacteria producing
butyric acid from sugar
Fresh cream Bacteria
Cream Lipolytic bacteria
Cream B. cereus
Chocolate tea-cakes Osmophilic yeasts
Biscuits Molds
presence of Pseudomonas fragi. Pseudo-
monas fragi produces a lipase that initially
hydrolyzes short-chain fatty acids from the
milk lipids and then esterifies these acids
to their corresponding ethyl esters. Ethyl
butyrate and ethyl caproate have been
found to be the OF compounds responsible
for this defect (Shipe et al. 1978).
Malty OF occurs occasionally in milk that
has had some temperature abuse (storage at
10°C or above). The malty OF is caused
by Streptococcus lactic subsp. maltigenes
(Bradfield and Duthie 1966) or Lacto-
bacillus maltaromicus (Morgan 1976). The
malty character itself is due primarily to
3-methyl butanal production from leucine.
Additional examples of OF produced in
foods from MO are provided by Goldenberg
and Matheson (1975). A summary of OF
they have encountered at Marks and Spencer
is presented in Table 4-4. It is quite obvious
from their tabulation that OF due to MO
can occur in a wide variety of products.
Summary
Some of the OF which have been found to
occur in foods has been discussed in this
chapter. Unfortunately, the occurrence of
OF is quite common and the causes are very
Off-Flavors in Foods 133
Comments
Off-flavor due to "bad" egg; either use of poor-
quality egg or careless handling during or after
thawing of frozen eggs.
Mold due to contamination by flour dust in bakery.
"Soapy" off-flavor in coconut.
Inadequate processing or inadequate cleaning or
washing of equipment.
Contamination by yogurt.
"Cheesy" off-flavor due to growth of lipolytic
bacteria either in milk or during processing before
pasteurization.
Causes "bitter" flavors.
Causes fermentation and "beery" off-flavors.
Musty flour used and not examined before use.
diverse. It is impossible to present a detailed
discussion of all the OF reported in the
literature. In some cases, the source of
the OF has never been found. Despite the
sophisticated instrumentation available to
the flavor chemist, identification of OF in
foods is literally like "looking for a needle
(one or two OF compounds) in a haystack
(the normal flavor profile of the food)."
When one appreciates the very low sensory
thresholds one may encounter in OF flavor
compounds [e.g., bis-(2-methyl-3-furyl)-di-
sulfide, 2 parts in 10 14 parts water; Buttery
et al. 1984], the task of finding and then
identifying the OF becomes very formi-
dable. Hopefully this chapter provides a
better appreciation for the diversity and the
host of OF sources in foods.
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5:153.
Chapter 5
Process Flavors
Charles Manley
INTRODUCTION
Flavors may be produced by a large variety
of methods, from the purely synthetic ap-
proach, to the extraction of volatile com-
ponents from materials of botanical origin.
Science and technology have led us to more
sophisticated ways of creating flavors. An
area of knowledge that has developed into a
major commercial venture for the flavor
industry is the production of process flavors.
The term "process flavor" has been used to
define a group of flavors or flavoring in-
gredients that are produced from precursor
materials via some type of processing
technique(s). The major processing tech-
niques in use today are thermal processing
and enzyme modification. Both techniques
have been in commercial use for approxi-
mately 25 years and currently represent a
significant part of the flavors industry's
commercial and research activities. A
summary of the general types of process
flavors is given in Table 5-1.
What makes this area of flavor chemistry
different from the traditional methods is the
relationship of the development of the
aroma profiles to knowledge of natural,
chemical or biochemical pathways that are
known to create aromas. The difference
between the occurrence of the flavors in a
natural system (e.g., meat, nuts, cheese and
butter) and in a process flavor is the intel-
ligent selection of precursors and processing
conditions that allow for the optimum
production of the aroma profile. These
flavors have a close relationship to their
natural food-derived counterparts.
Three major factors that support the
success of these flavors and flavoring in-
gredients are inherent in process flavor
technology. First, because the creation of
the process flavor is based on chemical and
biochemical knowledge of the original food,
its flavor profile is very close to that of the
food it is duplicating. The use of synthetic
chemicals to produce a flavor generally
exaggerates the flavor profile.
Second, because the flavor is produced
from selected precursors and not necessarily
the total food, a great degree of control on
its production and economy of manufacture
may be gained. Typically, less than 0.1
percent of a powerful aroma is necessary to
be present in a food to act as a flavor. This is
particularly true in the savory/meat flavor
area where some of the flavoring com-
ponents have odor thresholds in the part per
billion and trillion level! The definition of
a flavor captures the notion that it is a
powerful material whose significant function
139
140 Source Book of Flavors
TABLE 5-1. Summary of the types of process flavors
Mechanism Flavor type
Thermally generated Processed (reaction)
flavor
Chemical hydrolysis Hydrolysates
Controlled of oxidation Fat flavors
Autolysis-Enzyme Autolysates
conversion with
endogenous
enzymes
Enzymolysis Enzyme modified
Fermentation Flavor
is flavor and not nutrition or functionality
(Food and Drug Administration 1990)'.
Third, because the materials are pro-
duced via "natural" mechanisms such as
roasting, fermentation and enzymolysis, the
final flavor may qualify as a natural flavor or
flavoring ingredient. This is particularly true
if the precursor is a traditional food or food
component, and the processing conditions
are those used in traditional food pre-
paration and the resulting product qualifies
as a flavor. Newer, more nontraditional uses
of process flavor technology come under
more discussion when the term "natural" is
to be applied. Both the industry and the
regulatory groups have been considering a
new definition of the term "natural." As
of this publication, there has been no
resolution of the issue.
During the last 20 years, several hundred
patents on process flavors have been
granted around the world (see Heath 1981
and Chapter 14 of this text). However, no
single patent has provided a rigid speci-
fication for the thermally processed flavor.
Recently, the International Organization of
Flavor Industries (IOFI) has established a
guideline for the manufacture of process
flavors [International Organization of
Flavor Industries, 1990; see Appendix 5.1].
As noted in their guidelines and in the
patent literature, the basic compounds used
to create a process flavor are amino acids
(particularly the sulfur-containing ones),
reducing sugars, thiamine (vitamin B1), and
known synthetically produced components
from the Maillard reaction (i.e., dialde-
hydes). Many of the resultant components
of the reactions have been isolated and
identified. These compounds were then
synthesized and patented for use as a syn-
thetic flavoring ingredient. Major com-
pounds are pyrazines, thiazolines, fur-
anones, furans, polysulfide compounds
(thianes) and thiophenes.
The two major divisions of process flavors
are the thermally processed flavors and
flavors produced by enzymatic modification.
THE THERMALLY
PROCESSED FLAVORS
(MEAT AND SAVORY FLAVORS)
The use of thermal methods for flavor
development is nearly as ancient as man
himself. The use of fire in preparing food
has been estimated to be upward of 10,000
years old. However, it is only in recent
history that the chemistry of thermally
induced flavor development has become
well understood.
The first thermally produced flavoring
material can be traced to the production of a
product called hydrolyzed vegetable protein
or, more commonly, HVP. It was developed
by Julius Maggi, a Swiss chemist, during
the last century (Manley 1989). The first
chemical understanding of the development
of flavors by heat is associated with the
work of Dr. Louis Camille Maillard of the
University of Nancey (France) from 1912 to
1936. Significant symposia have been held
on the subject of the "Maillard reaction"
mechanism (appropriately named for its
discoverer, but some 15 years after his
death) in the development of aromatic
materials from precursors consisting of
amino acid and reducing sugars (Hodge
1976; Waller and Feather 1983; Kawamura
1985; Fujimaki, Namiki, and Kato 1986;
Buckholz 1989; and Finot et al. 1990). A
fundamental discussion of these mechanisms
can be found in one of the more recent sym-
 Process Flavors 141

posia on the subject (Parliment, McGorrin,
and Ho 1989).
The basic challenge to the scientist in
producing thermally generated flavors is in
the understanding and selection of the
precursor materials and processing con-
ditions. Although the "Maillard reaction" is
a major pathway for aroma development,
other chemical pathways also make signi-
ficant contributions to aroma formation.
Table 5-2 reviews the types of thermally
driven chemical mechanisms that make
significant contributions to aroma produc-
tion. The major literature cited will help in
understanding the chemical mechanisms
and, to some degree, the usefulness of the
aroma profile generated.
Although there is a very diverse amount
of chemistry related to thermal processing,
it is reported that the heterocyclic aromatics
generated during the reactions are the most
interesting and useful in the preparation of a
flavor (Vernin 1982). These compounds are
also generally the most difficult to produce
by chemical synthesis.
Although the patent literature is full of
references on the manufacture of thermally
produced flavors, only approximately 45 are
used in commercial production (Buckholz
1989). Table 5-3 indicates the more signi-
ficant patents protecting the manufacture of
process flavors.
The key aromatic compounds of value
in creating meat-like, cooked and roasted
flavors are the heterocyclic in nature. Table
5-4 lists the types of compounds, their
typical aroma character and their ranges of
threshold values. Many of these chemicals
have been produced by synthetic chemistry
and have been approved as GRAS (Gen-
erally Recognized As Safe) by FEMA's
(Flavor and Extract Manufacturer's As-
sociation) Expert Panel or by the FDA. The
variety of materials are numerous and their
odor thresholds have a very dynamic range.
Fors (1981) has prepared a fine review of
many of the sensory properties of the
volatile Maillard reaction products.
There are various types of process flavors
used either singly or in combination with
other similar materials to produce the final
commercially available flavor. The major
types are discussed below.
Protein Hydrolysates
As mentioned earlier, hydrolyzed vegetable
proteins (hydrolysates/HVP) were the first

TABLE 5-2. Mechanisms for thermal development of flavor

Reaction types Major precursor(s) Typical aroma resultant Major literature review

"Maillard" Amino acids and Various Waller 1983

reducing sugars
Strecker degradation Amino acids and Aldehyde Parliment 1989
reducing sugars
Condensation Dicarbonyl compounds Pyrazines Maga 1982
from sugar and amino
acids or ammonia
Sulfur addition Furanone compound +5' Thiazoles Van den Ouweland
Nucleotides w/sulfur Thiazolines 1975
containing material Shu 1989
Decomposition Thiamine (vitamin B1) Thiazoles Werkhoff et al. 1990
Thiazolines Guntert et al. 1990
Thiofurans
Oxidation Unsaturated fatty acids Unsaturated aldehydes Nawar 1989
Hydrolysis Vegetable and animal Pyrazines ( +) plus Manley 1981
protein complex mixture
Cyclo-Dehydration Sugars 5 Hydroxy-Furfural + Hodge 1967
142 Source Book of Flavors

TABLE S-3. Mlijor thermal process flavor patents (see Chapter 15)

!-Cysteine May 1960*

USA 2,934,435
Furaneol Vanden
!-Cysteine Ouweland
USA 3,904,655
Chicken Chuy
Protein/thiamine USA 4,081,565
2-hydroxy Weiner
Ethylammonium USA 3,645,754
Hydrogen Sulfide
3-methyl butanol
Xylose 60-180°C Roast beef Baugher
!-cysteine 3min USA 3,930,046
HVP
HVP l00°C/2 hrs Beef Van
!-cysteine xylose Pottelsbughi
Malic acid USA 3,716,380
Guanylate
Yeast autolysate Beef USA 2,109,084
HVP, lactic acid
Fried onion ll5°C Onion Huth
40min USA 3,424,592
• Original processed flavor patent

TABLE S-4. Threshold ranges of key aromatic compounds in process flavors

Key aromatic Range of thresholds

compounds Range of flavor types (in water)

Thiazolines Roasted 3 ppm to 0.003 ppb

Cooked onion
Meaty
Pyrazines Roasted 25 ppm to 0. 006 ppb
Green
Popcorn
Nutty
Furanones Caramel 1 ppm to 0.03 ppb
Meat-like
Furans Sweet-burnt 5ppm to 6ppb
Rum-like
Green
Aldehydes Fruity green 15 ppm to 0.2 ppb
Poly sulfide compounds- Onion/garlic 50 ppb to 2 ppb
e.g., thianes
Thiophenes Fried onion 200 ppb to 1 ppb
Mustard-like

process flavors. These materials are pro- acid hydrolysis of the protein to amino acids
ducts of acid hydrolysis of proteins (usually and from the heating steps. During the
of plant origin, but can be from animal processing, the residue carbohydrate in the
protein). They acquire their flavor from the protein source is reacted and also generates

some aroma. The manufacturer of HVP
is able to adjust the flavor profile of the
resulting material by the degree to which the
material has been processed, the substrate
used (protein source) and resultant cleanup
of the raw hydrolysate. These steps include
the use of activated carbon, to remove some
color and harsh flavor notes, and the pre-
cipitation of hydrophilic amino acids (bitter
amino acids) and the general aging of the
material (Manley 1981).
The resulting material can have many
flavor characteristics from roasted-bitter to
mild-brothy. HVP's have been used for
many years as the basis of building meat-like
flavors. They contribute not only aroma
notes, but also taste character. The taste
contribution is related to the amount of salt
and monosodium glutamate (MSG). MSG
results from the glutamic acid in the protein,
and the salt is the product of hydrolysis
(HCl) and its neutralization.
The Umami (taste enhancing) properties
of MSG are well-known and, in fact, early
hydrolysates (particularly produced from
wheat) were produced specifically to isolate
the MSG for use as a flavor enhancer in
foods. This was the industry practice until
the late 50's, when fermentation methods
proved to be more economical.
Yeast and Autolyzed Yeast Extracts
Yeast products and, in particular, their
autolyzed extracts (generally referred to
as autolyzed yeast extract AYE) are in-
gredients quite similar to HVP. In a sense,
these are the earliest of process flavorings
based on the use of enzymes to create a
flavor profile. In the case of AYE, the
endogenous enzymes are used to break
down the yeast components (proteins,
nucleotides, vitamins and carbohydrates) to
substrates useful in creating aromas during
heating. More recent practice by manu-
facturers of AYE and process flavors is to
add enzymes, not native to the yeast, to
develop specific flavor and taste profiles.
The substrates available in a yeast make
Process Flavors 143
it an ideal candidate for processing into
meat or savory flavorings. The protein
content is high, and it contains certain other
components, such as thiamine (vitamin B1),
nucleic acids and sulfur-containing amino
acids, all of which can generate strong flavor
profiles when heat activated. One such
component of a thermal reaction in yeast is
bis (2-methyl-3-furyl)-disulfide:
s-s
rc(){J
0 0
It has been found to have an aroma
threshold of 2 parts in 1014 parts of water
(Buttery 1984, Hartman 1984).
The nucleic acids themselves are useful
as flavor enhancers in savory flavors. The
flavor-enhancing properties of these ma-
terials are well documented (Boudreau
1979, Cagan 1979, Yamaguchi 1979).
Yeast and AYE find use directly in
compounded flavors for their inherent
flavor profile, as well as being used in
complex process flavor systems where
amino acids, thiamine and nucleic acids are
reacted to produce strong aromas.
Basic Process Flavorings
The early process flavorings were based on
the reaction of selected components such
as thiamine, amino acids, reducing sugars
and hydrolysates. The first commercially
available process flavors were essentially
sophisticated hydrolysates. These materials
are still the "workhorses" of the industry.
They are materials used to bring more
character to a savory flavor. They usually
produce a general meaty, roasted, or
cooked note (Ames 1985). They are con-
siderably more intense than the basic HVP
or AYE and deliver more aroma character.
Complex Process Flavorings
The simple process flavors are useful in
generating nonspecific aromas. The more
144 Source Book of Flavors
recent generation of process flavor devel-
opment has focused on the production of
species specific aroma profiles. The use of
very specific precursors and thermal pro-
files allows for the generation of specific
chemicals known to be necessary for creat-
ing the aroma of a certain species of cooked
animal meat. Chemicals, such as the dienals,
generated from the thermal breakdown of
unsaturated fats and fatty acids, create
strong chicken aroma (Van den Ouweland
1980). High amounts of the amino acid
proline allow for the generation of bread
and/or cracker notes (Schieberle 1989;
Tressl, Helak, and Martin 1985; Yong et al.
1989).
This technology requires the chemical
knowledge of the actual foods and their
processing conditions. The substrates and
processing conditions may be very complex.
It is an area of development that is very
close to food itself. In fact, the development
of gravies, roux and many basic sauces are
the classical analogy in the food preparation
area to the process flavor. Much of the
knowledge in this area is not covered in
patents, but is maintained as trade secrets
by the companies manufacturing the flavors.
Because of their complexity, it is generally
very difficult to reproduce these flavors
without specific knowledge of the formu-
lation and processing steps. In some cases,
the final products use meat, meat and
vegetable protein, or fat that has been
enzymatically converted to thermally re-
actable precursor materials prior to the
thermal processing step(s).
As noted above, many of the aromatic
materials used in creating meat and savory
flavors, which have been generated by
thermal processing, have been synthesized
and approved as GRAS.
The Final Flavor
The final commercial flavor may be a mix-
ture of any of the flavors or flavoring in-
gredients noted above with the addition
of carriers, antioxidants, solvents, other
TABLE 5-5. Optional materials used in the manu-
facture of reaction flavors
Sodium chloride Antioxidants
Monosodium glutamate Modified starch
Ribotides (5'nucleotide) Gums
Maltol and ethyl maltol
TABLE 5-6. Food products using meat and savory
flavors
Soups Sausages
Gravies Syrups
Sauces Pot pies
Snacks
Meat products Beverages
Boullions Toppings
Broths Confectionery products
flavors, flavor adjuncts and flavor enhancers.
These materials are noted in Table 5-5.
These flavors have seen significant sales
growth in the past 15-20 years. The esti-
mated sales volume of these materials in
1990, including HVP and AYE, is estimated
to be in the $250 million range (Manley
1991). They find use in a great array of final
food products as noted in Table 5-6.
Now let us turn our attention to the use of
enzymes and microorganisms in the pro-
duction of dairy flavors.
ENZYME MODIFICATION AND
FERMENTATION-THE
DAIRY FLAVORS
Dairy products are some of the oldest of
man's foods and are certainly one of the
most important classes of food for nutrition.
There is a great array of dairy products
based upon the species of animal used for
the milk, the processing conditions and the
enzymes and/or microorganisms used to
develop the desired texture and flavor
character. Table 5-7 notes the types and
some of the specific dairy products available
around the world. It is interesting to note
that the types of dairy products available are
 Process Flavors 145

TABLE 5-7. Types of dairy products available on the the world are the cow, goat, water buffalo
world market and sheep.
Milk Milk is a very complex natural material
• Fresh containing fats, sugars (mainly lactose),
• Pasteurized proteins (such as lactalbumin) and salts
•UHT (such as calcium phosphate). The taste and
• Canned aroma of fresh milk is minimal, with most
Cream of the taste coming from the fat and salt
Butter system. The aroma is faint, but is due to
• Ghee (Buffalo Milk) a combination of feed notes inhaled by
• Margarine (Imitation) the cow and directly tansferred to the
Cultured Products milk and cooked notes coming from the
• Yogurt pasteurization process.
• Butter Milk Milk fat is the major source of flavors
• Acidophil us Milk
• Bulgarian Milk
particularly when the milk is processed
• Yakult further or is treated with enzymes or micro-
• Leben organisms. Table 5-8 notes the types of fats
• Kifur and lipid material contained in milk fat.
Ice Cream The fatty acid composition of milk lipids is
Cheeses
also very complex and unique among food
• Fresh Soft Low-Fat Cheese products. Over 60 fatty acids have been
• Cream/Neufchatel reported in cows' milk (Herb 1962). Quan-
• Gouda/Munster tities of butyric, caproic, caprylic and capric
• Port du Salut (Flavored) acids (fatty acids with 4, 6, 8, and 10 carbon
• Brie/Camembert
• Blue Cheeses
atoms respectively) are unique to milk and
• Goat Cheese of great importance in the development of
• Emmental dairy flavors. For example, the oxidation of
• Cheddar unsaturated octadecadienoic acid (linoleic
• Parmesan/Romano acid) leads to the formation of 4-cis-heptenal
• Whey/Ricotta
that has been reported as a cream-like flavor
component in milk and butter (Haverkamp-
Begeman 1964). Small amounts of free
strongly related to national and ethnic butyric acid are important to butter flavor as
references. In many cases, that reference is well as to most cheese flavors. One should
specific to the geographic or ethnic niche.
For example, Yakult in Japan and Kifur in
TABLE S-8. Fats and lipids in milk
Russia are dairy products which are little
known outside their principal area of con- Range of occurrence (%)
sumption, whereas, butter, Cheddar cheese Type of fats in cow's milk
and yogurt have found nearly world-wide Triglycerides 97.0-98.0
consumer acceptance. Diglycerides 0.25-0.48
The creation of dairy flavors has been Monoglycerides 0.015-0.038
closely related to the understanding of the Keto acid glycerides 0.85-1.28
precursor chemistry (substrate) and pro- Aldehydo glycerides 0.011-0.015
Glyceryl ethers 0.011-0.023
cessing (biochemical conversion) to create Free fatty acids 0.10-0.44
desirable aromatic chemicals. The universal Phospholipids 0.2-1.0
substrate for dairy products is milk. Al- Cerebrosides 0.013-0.066
though milk may come from any of many Sterols 0.12-0.4
mammals, its most common sources around [Kurtz 1965]
146 Source Book of Flavors

also note that milk fat contains a small
amount of bound hydroxy and keto acids,
which are readily hydrolyzed by either
microbiallipases or theraml treatment. Free
hydroxy acids readily cyclize into lactones
and the keto acids degrade into methyl
ketones.
The mechanisms of flavor development
are reviewed in Table 5-9. This table is an
indication of the complexity that was noted
above. A number of comprehensive reviews
on these mechanisms exist in the literature
(Manley 1991, Vernin 1982).
In order to get a better understand-
ing of the nature of dairy flavors, it is
best to review categories that relate to
specific flavor profiles or routes of flavor
development.
TABLE 5-9. Mechanisms of dairy flavor formation
Thermally Directed Reactions
• Maillard reactions
• Sulfur release
• Triglyceride hydrolysis
• Oxidation of unsaturated fatty acids
• Caramelization (high temperature)
Enzymatically Directed Reactions
• Lipases-release of fatty acids and hydroxy fatty
acids for lactone formation
• Esterases-same as lipases
• Proteases-release of peptides for aged taste of
cheeses
Microbiologically Directed Reactions
• Lactic-producing organisms' lactic acid taste-pH
change
• Molds-Roquefort-blue cheese with methyl
ketones
• Propionbacteria-Swiss type with propionic acid

pasteurization step (15 seconds at 72°C) or

Milk and Cream Flavors
These flavors are representatives of dairy
products that are minimally processed.
Typically, they are heat treated in either a
ultrahigh temperature treated (UHT-a
few seconds at 135°C to 150°C). This ther-
mal exposure gives rise to flavor develop-
ment from:

TABLE 5-10. Milk and cream aroma components

Component Flavor Note

Fatty acids Milk taste components

4-cis-heptenal Cream-like
Methyl ketones Low levels-(below threshold)
together give cream-like; also
cause stale off-flavor at higher
levels
Lactones (high carbon #8-12) Cooked-butter notes
Coconut flavor character
Maillard reaction products Heated milk produces caramel notes
Dimethyl sulfide (from s-methyl methionine Malty or cowy flavor detect in milk
sulfonium salt) from cow's diet
Oxidation of Lipids (Aldehydes and "Card-boardy" off odor-defect
Ketone e.g., hexenal and 1-octen-3-one)
Degradation of methionine producing Sunlight defect
methional, methyl sulfide, dimethyl
sulfide and dimethyl disulfide
Sugars Sweeteners
Diacetyl Buttery notes
Lactic acid Sourness
ClO and C12 Sweet
Fatty acids Cream
Butyric acid Higher levels give rancidity note and
character
 Process Flavors 147

• Degradation of thermally liable pre- product, acetaldehyde. There is no agree-

cursors found in milk.
• Product of sugar/protein (amino acid)
reactions.
• The release of sulfur-containing com-
ponents.
• Degradation and mild oxidation of tri-
glycerides in fat.
Table 5-10 outlines the aromatic com-
ponents generated that are related to a
specific flavor profile in creating milk or
cream flavor. This is one of the most de-
licate of flavor profiles, and one that needs
the skilled flavor chemists to blend the
chemical components or materials from
processing to achieve an acceptable final
flavor.
Cultured Dairy Flavors
ment on the acetaldehyde values that give
optimum flavor effect (Groux 1973). Levels
from 13 to 41 ppm have been reported as
optimum (Badings 1980, Green 1982).
The last compound of flavor interest in
cultured milk products is diacetyl: a meta-
bolite of citrate by the action of Streptococci
or Leuconostoc organisms (Collins 1972).
This component contributes strongly to a
buttery-type flavor at levels of 1-2ppm
(Steinholt 1971).
Butter Flavor
Butter is a product of the concentration of
the fat in the milk by mechanical separation.
The resultant product is a water in oil emul-
sion with a reasonably mild characteristic
flavor. During the process, a small portion

Cultured products are some of the first

products developed from milk. Originally, TABLE 5-11. Recent butter/cheese flavor patents
fermentation occurred naturally to milk set (see Chapter 14)
aside for later consumption. The spoilage
Brief description Patent citation
organisms in the milk produced the proper
conditions for the presentation of the final Butter oil/lipase-blue Shay et al. 1990
cultured product. The basic fermentation is cheese-like EP357812
due to lactic acid bacteria. Originally, the Lactones from lipids for Haring 1989
margarine EP321055
fermentation was performed with a mixed Diketone precursors as a Doornbos 1988
or "unknown" culture or "back-slop"; butter-like flavor EP293957
modern technology has developed the pure Heated fatty acids at 150-475°C Chen 1988
cultures with their predictable performance to give a dairy flavor EP295509
potentials. Hydrolyzing butter and coconut Shukunobe1988
oil with lipases J 63240755
The major flavor and taste component in Butter/cream/cheese flavor from Tojo 1988
these products is the lactic acid produced fat treated with lipases from J 64002549
by the fermentation of the sugar by the Chromobacterium
bacteria. The preferred metabolite, in flavor Green notes from soybean with Kanisawa 1988
terms, is the L ( +) Lactic acid (Kielwein lipases USA4769243
Acetyllacetic acid is converted to Unilever 1987
1979). The D (-) enantiomer has a harsh diacetyl during baking NL8601078
off-flavor note. The acid note is the most Lipolyzed butter fat by Chang 1987
significant one in this category. One excep- Leuconostoc cremoris USA4670267
tion is the product from Russia, called Sugar and butter heated at lzzo 1987
Kifur, which undergoes a secondary fer- 150-250°F to produce aqueous USA4684532
soluble butter flavor
mentation to create ethyl alcohol. This Omega-alkenyl methyl ketone MeijiFoods
product is often called, with good reason, for butter flavor J 59039822
the "Champagne of Milk" (Shahani 1983). Lipolyzed cultured cream Bakal1983
The flavor of yogurt is also influenced USA 4414229
by the amount of another fermentation J = Japan EP = Europe NL = Holland
148 Source Book of Flavors

of the fats are broken down to fatty acids by
enzymes. Lactones are also formed from the
small amount of <>-hydroxy acids occurring
in the milk fat. The y-lactones may also form
from the unsaturated C18 fatty acids via
hydration and ~-oxidation.
The major flavor components used to
create butter flavors are diacetyl, lower
carbon number fatty acids and higher
carbon number lactones. Some of the flavor
notes in sweet cream butter may be due to
the deca and dodecanoic acids (Ramshaw
1974) and the methyl ketones (Langler
1965).
Margarine, an imitation butter, is one of
the major uses for butter flavors. Because
margarine is used in cooking, it is desirable
to create a flavor that generates a butter
flavor upon heating. The heated butter
flavor is due to the thermal generation
of certain flavor components (usually
lactones). Certain lactone precursors have
been synthesized so that margarine may
have the same flavor profile as butter after
heating. A number of patents have been
issued that cover butter flavor; some signi-
ficant ones are summarized in Table 5-11.
Cheese Flavors
The many varieties of cheese represent
centuries of cultivation of the art of cheese
making, with its creation of many different
flavors, tastes and textures. The different
types of cheese are the result of many types
of microorganisms (yeast, bacteria and
mold) working together with the basic milk
sources (which are typically cow's, goat's or
sheep's milk).
The basic families of cheeses are noted in
Table 5-12 with their corresponding flavor
character noted and the major components
contributing to their aroma profile. By far,
the most popular cheese in the USA is
Cheddar cheese. It is an English invention
that uses a unique process, "cheddaring,"
introduced to repress the growth of spoilage
organisms by piling and repiling blocks of
warm cheese curd in the cheese vat, leading
to rapid increase of lactic acid. During this

TABLE 5-12. Components related to specific cheese flavor character

Component Cheese Variety Flavor Note

Small peptides Swiss Sweet taste

Gouda/Muenster
Fresh milk components Cream Cheese Mild milk
Neufchatel
Small peptides, proponic acid Emmental Sweet taste low level
(<1%)
4-mercapto-4-methyl Pentanone-2 Gouda Fatty note as a defect
Bitter-hydrophilic peptides Aged Higher amount of
Cheddar peptides related to
rough aging
character
Acetic acid Sharp Sharp character
Cheddar
Medium chain fatty acids (C6 to Mild Overall cheddar
CIS) Cheddar character
Methanethiol Aged note Aged note (threshold
Cheddar at 0.02ppb)
Acetylpyrazine 2-methoxy-3-ethyl Aged Aged note-nutty
pyrazine Cheddar (microbial origins)
Relatively large amount of CS and Blue Background aroma
CIO saturated fatty acids
Methyl ketone Blue Characterizing aroma

period, the rapid increase in acid destroys
the coliform (spoilage) bacteria.
Aged cheese, particularly Cheddar, owes
most of its taste character to the peptides
formed during curing. These components
contribute to the bitter and umami taste of
the aged product. The sharpness is generally
related to the release of acetic acid during
the ripening process. The medium-chain
fatty acids (C6 to C18) that are released
during the ripening process have also been
shown to be important in Cheddar cheese
flavor character (Bills and Day 1964).
Creation of Dairy Flavors
The significant aroma and taste components
discussed above may be blended to produce
various dairy flavors. These components
may be generated by chemical synthesis,
extraction from natural material or pro-
duced by biotechnology (enzymolysis or
fermentation).
The major chemicals found in dairy
flavors have been synthesized and placed on
the FEMA or FDA GRAS List. Other
materials such as starter cultures (concen-
trated diacetyl), enzyme modified cheese
and other fermentation products are al-
lowed. All of these materials allow the
flavor chemist to create the specific dairy
flavor profiles for use in a variety of food
products.
REGULATORY ISSUES
General regulatory issues related to flavors
are covered in another section; however,
the specific issues related to savory flavors
and dairy flavors need some discussion in
this section. These flavors are generally
regulated, over all, by the Food and Drug
Administration under either the GRAS
(21 CFR section 172.510-172.590) or the
natural flavor section (21 CFR section
101.22). Natural flavor claims can be
made when the flavor is made from natural
substrate by methods indicated in the
regulation.
Process Flavors 149
When the savory flavors are produced
with amounts of meat or meat by-products
exceeding 2 percent of the flavor, their
production comes under the supervision of
the US Department of Agriculture's Meat
Inspection Department (MID). Flavor man-
ufacturing facilities that produce flavorings
with meat/poultry or their by-products must
have their plants qualified as a USDA-
inspected plant and have USDA field in-
spection.
A flavor not containing the maximum
allowed meat/poultry or by-product may
also come under USDA's regulations when
the flavor is used by a meat- or poultry-
producing plant that is under USDA MID
inspection. As an aid to having the flavor
qualified for use in such a plant, it is useful
to have the formulation reviewed by the
Proprietary Mix Committee (PMC) of
USDA in Washington, D.C. A standard
form for submission of information for
review of the flavor's formula can be ar-
ranged by writing the chairman of the
Proprietary Mix Committee, Food Safety
and Inspection Service of the United States
Department of Agriculture at 300 12th St.
SW, Washington, D.C. 20250-3700.
There are specific ingredients used to
make savory and dairy flavors that must be
identified to the PMC during the formula
review procedure. Table 5-13 indicates
those ingredients that need to be acknowl-
edged in a formula disclosure to the PMC.
The basis of the disclosure is to indicate
to the consumer the presence of any of
the following materials: (1) materials of
religious or ethnic interest (Kosher); (2)
materials of health concern in terms of
allergic activities (proteins); (3) materials
TABLE 5-13. Materials used in process flavorings
that must be labeled
• Proteinaceous materials
• Food materials
• Functional (in final product) ingredients
• Fats or oils
• Materials that are under religious review
150 Source Book of Flavors
that are personal aversions (MSG); and (4)
materials that have water binding capa-
bilities or make a significant nutritional
contribution to the final food.
The new regulation regarding labeling of
flavors for USDA products was issued in
1990 (US Department of Agriculture 1990).
APPENDIX 5.1. IOFI Guidelines for the production and labeling of
process flavors
I. INTRODUCTION
Process flavorings are produced by heating
raw materials that are foodstuffs or con-
stituents of foodstuffs in similarity with the
cooking of food.
The most practical way to characterize
process flavorings is by their starting ma-
terials and processing conditions, since the
resulting composition is extremely complex,
being analogous to the composition of
cooked foods. They are produced every day
by the housewife in the kitchen, by the food
industry during food processing and by the
flavor industry.
The member associations of IOFI have
adopted the following Guidelines in order to
assure the food industry and the ultimate
consumer of food of the quality, safety
and compliance with legislation of process
flavorings.
II. SCOPE
1.1 These Guidelines deal with thermal
process flavorings; they do not apply to
foods, flavoring extracts, defined flavor-
ing substances or mixtures of flavoring
substances and flavor enhancers.
1.2 These Guidelines define those raw
materials and process conditions that
are similar to the cooking of food, and
which give process flavorings that are
admissible without further evaluation.
At the time of this text's publication, the
FDA had not made changes to its regulation
regarding these products. It is believed that
such changes will be made shortly so that
one should review the regulation regarding
the current rules for making and labeling
these flavors.
III. DEFINITION
A thermal process flavoring is a product
prepared for its flavoring properties by
heating food ingredients and/or ingredients
permitted for use in foodstuffs or in process
flavorings.
IV. BASIC STANDARDS OF GOOD
MANUFACTURING PRACTICE
Chapter 3 of the Code of Practice for the
flavor industry is also applicable to process
flavorings.
V. PRODUCTION OF PROCESS
FLAVORINGS
Process flavorings shall comply with national
legislation and shall also conform to the
following:
A. Raw Materials for Process Flavorings
Raw materials for process flavorings shall
consist of one or more of the following:
4.1.1 A protein nitrogen source:
-Protein nitrogen containing foods
(meat, poultry, eggs, dairy products,
fish, seafood, cereals, vegetable
products, fruits, yeasts) and their
extracts.
 Process Flavors 151

-Hydrolysis products of the above, Suitable carriers, antioxydants, pre-

autolyzed yeasts, peptides, amino
acids and/or their salts.
4.1.2 A carbohydrate source:
-Foods containing carbohydrates
(cereals, vegetable products and
fruits) and their extracts.
-Mono-, di- and polysaccharides
(sugars, dextrins, starches and
edible gums).
4.1.3 A fat or fatty acid source:
-Foods containing fats and oils.
-Edible fats and oils from animal,
marine, or vegetable origin.
-Hydrogenated, transesterified and/
or fractionated fats and oils.
-Hydrolysis products of the above.
4.1.4 Materials listed in Appendix Table
A5-1.
4.2 Ingredients of process flavorings.
4.2.1 Natural flavorings, natural and nature-
identical flavoring substances and
flavor enhancers, as defined in the
IOFI Code of Practice for the flavor
industry.
4.2.2 Process flavor adjuncts
serving agents, emulsifiers, stabilizers
and anticaking agents listed in the lists
of flavor adjuncts in Annex II of the
IOFI Code of Practice for the flavor
industry.
B. Preparation of Process Flavorings
Process flavorings are prepared by pro-
cessing together raw materials listed under
4.1.1 and 4.1.2 with the possible addition of
one or more of the materials listed under
4.1.3 and 4.1.4.
4.3.1 The product temperature during
processing shall not exceed 180°C.
4.3.2 The processing time shall not ex-
ceed 1/4 hour at 180°C, with corre-
spondingly longer times at lower
temperatures.
4.3.3 The pH during processing shall not
exceed 8.
4.3.4 Flavorings, flavoring substances and
flavor enhancers (4.2.1) and process
flavor adjuncts (4.2.2) shall be added
only after processing is completed.

APPENDIX TABLE AS- I. Materials used in processing

Herbs and spices and their extracts

Water
Thiamine and its hydrochloric acid salt
Ascorbic acid
Citric acid
Lactic acid
Fumaric acid
Malic acid
Succinic acid
Tartaric acid
The sodium, potassium, calcium, magnesium, and ammonium salts of the above acids
Guanylic acid and Inosinic acid and its sodium, potassium and calcium salts
Inositol
Sodium, potassium- and ammoniumsulfides, hydrosulfides and polysulfides
Acids, bases and salts as pH regulators:
Acetic acid, hydrochloric acid, phosphoric acid, sulfuric acid
Sodium, potassium, calcium and ammonium hydroxyde
The salts of the above acids and bases
Polymethylslloxane as antifoaming agent (not participating in the process).
152 Source Book of Flavors
C. General Requirements
for Process Flavorings
4.4.1 Process flavorings shall be prepared in
accordance with the General Prin-
ciples of Food Hygiene (CAC/Vol
A-Ed.2(1985)) recommended by the
Codex Alimentarius Commission.
4.4.2 The restrictive list of natural and
nature-identical flavoring substances
of the IOF I Code of Practice for the
flavor industry applies also to process
flavorings.
D. Labeling
The labeling of process flavorings shall
comply with national legislation.
5.1 Adequate information shall be provided
to enable the food manufacturer to
observe the legal requirements for his
products.
5.2 The name and address of the manu-
facturer of the distributor of the process
flavoring shall be shown on the label.
5.3 Process flavor adjuncts have to be
declared only in case they have a tech-
nological function in the finished food.
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Chapter 6
Biotechn ology for the Production
of Flavoring Materials
Susan Harlander
WHY BIOTECHNOLOGY?
There has been considerable interest in
the past decade in the potential use of
biotechnology as an alternative to conven-
tional extraction or chemical synthesis for
the production of "natural" food ingre-
dients. Biotechnology has been defined as a
collection of technologies that employ
biological or living systems (microorgan-
isms, plants or animals) or specific com-
pounds derived from these systems, for the
production of industrial goods and services.
The primary biotechnological techniques
that relate to the production of flavors
include: (1) plant cell and tissue culture
(PTC); (2) microbial fermentation; and,
(3) bioconversion of substrates using whole
microbial or plant cells or enzymes.
Despite the expense involved in devel-
oping biotechnology-based flavor produc-
tion systems, there are several forces driving
this approach. Health-oriented consumers
are concerned over the possible adverse
health effects of certain artificially produced
food additives; thus, there is increasing
preference for "natural" products. Flavors
derived from plant tissue culture systems,
microbial fermentation, or bioconversion
might be perceived to be more natural than
their chemically synthesized equivalent. The
public is also concerned about residues of
pesticides and herbicides used routinely in
agricultural production of plants used for
food and food ingredients. Tissue culture-
derived products circumvent the need for
such chemicals.
Consumer perception alone, however, is
not sufficient to motivate industry to pursue
biotechnological alternatives for flavor
production. Other motivating factors in-
clude erratic supply of raw materials due to
unfavorable weather conditions, seasonal
or crop variations, natural calamities or
political instabilities in the growing region.
Quality and consistency of flavoring agents
dramatically influences final product quality
and consumer acceptance. Enhanced flavor
production is not a high priority of plant
breeders; thus, genetic improvement via
classical plant breeding is not currently a
mechanism used for increasing yield of
flavor compounds or improving consistency
of the final product.
Flavor production systems based on PTC,
microbial fermentation, or bioconversion
overcome many of these limitations, and
provide the industry with consistent quality,
theoretically unlimited production capacity,
and, ultimately, reduced cost. Further,
enhanced yields are possible by control
155
156 Source Book of Flavors
of biosynthetic pathways and regulatory
mechanisms. It may also be possible to
produce new compounds or convert low-
value substances into high-value compounds
by biotransformation. Since flavors are
generally expensive compared to other
ingredients of processed foods, if biotech-
nology can compete economically with
traditional methods, industry will adopt
biotechnology-based systems.
DEFINITION OF "NATURAL"
According to the Code of Federal Regu-
lations 101.22.a.3 "natural flavor" or
"natural flavoring" means:
the essential oil; oleoresin; essence or extractive;
protein hydrolysate; or distillate of any product
of roasting, heating, or enzymolysis, which
contains the flavoring constituents derived from a
spice, fruit of fruit juice, edible yeast, herb, bark,
bud, root, leaf or similar plant material, meat,
seafood, poultry, eggs, dairy products, or
fermentation products thereof, whose significant
function in food is flavoring rather than nutrition.
This definition includes not only animal
or plant derivatives, but also includes
enzymatic and fermentation processes.
A natural flavor must be produced from
natural starting materials and the end
product must be identical to something
already known to exist in nature. Thus,
biocatalytic, but not chemical transforma-
tion of natural substances can be legally
labeled as natural. Any flavoring substances
not derived from these substrates are de-
fined as "artificial flavors."
It is apparent that this definition of
"natural" is broad and that the fine points
are subject to legal interpretation. For
example, although it is clear that flavors
derived by enzymatic action and fermen-
tation would be considered "natural" by
the U.S. Food and Drug Administration
(FDA), it is unclear at the present time if
plant tissue culture-derived flavors could be
classified as such.
PLANT TISSUE
CULTURE-DERIVED FLAVORS
As is illustrated in Chapter 8, plant ma-
terials are used as sources of many flavor
compounds. It is generally recognized that
plant compounds that are not required for
normal plant growth and development
by the metabolic pathways common to all
plants are referred to as secondary meta-
bolites. Flavor compounds are considered
secondary metabolites and are generally
produced in highly differentiated tissues
under specific growth conditions. The flavor
of a particular fruit or vegetable may be due
to literally tens or even hundreds of com-
pounds, many of which are present at trace
levels; however, frequently complex flavor
compositions are characterized by the
presence of one or a few high-impact com-
pounds. In addition, a characteristic odor
may be a consequence of a specific mole-
cular stereospecificity.
Plant tissue culture may provide alter-
natives to whole plants as biological sources
of flavor compounds. PTC is a technique
that allows plant cells to be grown in solid or
liquid medium, in much the same manner as
microorganisms are currently grown in the
laboratory. As illustrated in Fig. 6-1, tissue
explants from virtually any part of a living
plant (meristems, roots, leaves, or imma-
ture fruits) can be aseptically transferred to
solid media containing nutrients (a carbo-
hydrate source, mineral salts, vitamins) and
various plant growth regulators (phyto-
hormones such as auxins and cytokinins).
These explants proliferate into undiffer-
entiated cell masses called calli. Calli can be
propagated on appropriate growth media
that allows regeneration of whole plants
(A), or they can be transferred into liquid
culture media and grown as suspension
cultures (B).
De novo synthesis of flavor compounds
Plant cells are totipotent, meaning that
every cell, regardless of its source, has the
 Biotechnology for the Production of Flavoring Materials 157

A B

TISSUE EKPLRNT
leaf disc
shoot
root
Immature fruit

CALLUS FORMATION
proliferation of
undifferentiated
cells
EMBRYOGENESIS
end
DIFFERENTIATION

shoots~ LIQUID
SUSPENSION
roots~ CULTURE

!
REGENERATION
Of PLANTS
m BIORERCTOR

PRODUCTION Of
SECONDARY
METRBOLITES

FIGURE 6-1. Plant tissue culture technology (A) micropropagation and (B) liquid
suspension culture. (Hong and Harlander 1989)

potential to redifferentiate to normal plants under normal cultivation conditions. Under

with roots, shoots, leaves and flowers and
the complete range of biosynthetic path-
ways. All the genetic information is present
in cells grown in suspension culture; the
challenge according to Zenk (1990), a
pioneer in the PTC area, is to "obtain in
these suspension cells chemical differentia-
tion without morphological differentiation."
Although plant cells readily express those
enzymes involved in primary metabolism, in
most cell culture systems the products of
secondary metabolism will not be expressed
the right environmental conditions, sus-
pension cultures are capable of producing
secondary metabolites. Finding the right
conditions is a time-consuming and em-
pirical process, and there appears to be
no general pattern in the induction of
secondary product formation even within
cell cultures derived from members of the
same genus.
Once induction and production are
optimized, cultures can be grown in large-
scale bioreactors to produce useful sec-
158 Source Book of Flavors

TABLE 6-1. Examples of Secondary Metabolites Produced by PTC

Product Plant specie Yield (g/1)

Berberine Coptis japonica 7.0

Rosmarinic acid Coleus blumei 5.6
Shikonin Lithospermum erythrorhizon 3.5
J atrorrhizine Berberis stolonifera 3.3
Anthraquinones M orinda citrifolia 2.5
Galium vernum 1.7
Ajmaline Rauvolfia serpentina 2.0
Raucaffricine Rauvolfia serpentina 1.6
Shikimic acid Galium mollugo 1.2
Cinnamoylputrescine Nicotiana tabacum 1.0
Zenk (1990)

ondary metabolites at concentrations far secondary metabolites of interest, several

in excess of those produced by the differ- techniques have been used to induce flavor
entiated plant. Examples of secondary production by suspension cultures. Because
metabolites produced by PTC in excess of the pathways and regulation of secondary
1 g per liter of culture media are provided in metabolism are poorly understood, most of
Table 6-1. Unfortunately, the majority of the methods for induction of secondary
plants that produce biotechnologically metabolism have been selected empirically
interesting compounds of interest to the and include (1) manipulation of culture
food industry, including all plants producing medium composition, (2) manipulation of
scent compounds synthesized in glands, are environmental factors, (3) addition of
recalcitrant to induction of de novo flavor exogenous elicitors, and (4) induction of cell
biosynthesis. differentiation.
Successful production of secondary
metabolites at levels that compare favorably Manipulation of Culture Medium
with microbial fermentations and are equi- Composition
valent or in excess of levels produced by the The traditional approach for inducing
fully differentiated plant include the follow- secondary product accumulation in PTC is
ing strategies proposed by Zenk (1990): to manipulate the culture medium. Com-
ponents of the medium most frequently
1. Use of high-producing, differentiated examined include the effect of various
plants for the establishment of callus; phytohormones, and the type and concen-
2. Application of modern analytical tration of carbon, nitrogen and phosphate in
methods (e.g., radio- and enzyme the media.
immunoassay, fluorescence-activated The type, concentration and ratio of
cell sorter, etc.) for the quantitation of phytohormones significantly affects the
secondary products; growth and secondary metabolism of cul-
3. Selection of high metabolite-producing tured cells. The growth regulator, 2,4-
variant strains from a given population dichlorophenoxyacetic acid (2,4-D) has an
of cells; and, inhibitory action on the synthesis of a range
4. Establishment of specific production of secondary metabolites. Other phyto-
media, different in composition from hormones such as indoleacetic acid (IAA)
growth media. and naphthalene acetic acid (NAA) tend to
promote cell differentiation and/or result in
Since undifferentiated callus and cell low growth rates. While studying the effect
suspension cultures rarely produce the of different phytohormones on flavor pro-
 Biotechnology for the Production of Flavoring Materials
duction in undifferentiated celery tissue
culture, it was noted that replacing 2,4-D
with IAA initiated low-level production of
phthallide, the main flavor compound of
celery.
Carbon, nitrogen and phosphate in PTC
media are utilized for the synthesis of cell
constituents, as well as the formation of
intermediates and end products. Common
carbon sources used in PTC media include
sucrose, glucose and fructose. Increasing
the concentration of sucrose from 2 percent
to 4 percent increased polyphenol pro-
duction in rose cell suspension cultures.
Accumulation of secondary metabolites can
be influenced by the type and concentration
of nitrogen (ammonium and/or nitrate) used
to supplement the media. Increasing the
nitrate concentrations from 25 percent of
the normal complement to 100 percent
resulted in a progressive diminution of
ethanol-soluble phenolics in tobacco cell
suspension cultures. Phosphate limitation
increased accumulation of anthocyanin in
Catharanthus roseus cultures; increasing the
phosphate concentration enhanced the
production of anthraquinones in cultures of
Morinda citrifolia and indole compounds in
C. roseus suspension cultures.
Manipulation of Environmental Factors
Plant cells are highly influenced by environ-
mental factors: light, osmotic pressure,
gaseous atmosphere, pH and temperature
all influence secondary metabolite produc-
tion in PTC. It is well-known that secondary
metabolism in higher plants is influenced by
photoperiod; light also appears to be critical
for the formation of secondary metabolites
by PTC. Exposure of Ruta graveolens cell
cultures to light resulted in dramatic effects
on the proportions of volatile compounds:
alaphatic ketones and esters characteristic
of the leaves dominated in light-grown
cultures, whereas maintenance in the dark
led to the formation of irregular monoter-
penes typically found in the root. Light also
influences the production of anthocyanin
and betalain in suspension cultures; in some
159
cases, the specific wavelength of light used is
also critical.
Increased osmotic pressure, induced by
the addition of nonmetabolizable com-
pounds to the media, can influence produc-
tion of secondary metabolites. Pear fruit
suspension cultures initiated senescence
and produced ethylene in a medium con-
taining mannitol, a nonmetabolizable sugar
alcohol. Mannitol also induced an increase
in indole alkaloid production by cells of
C. roseus. A high concentration of carbon
dioxide in the atmosphere enhanced the
production of isobutanol, ethyl butyrate,
ethanol and ethyl acetate by apple and
grape cell cultures. The effect of carbon
dioxide was thought to be due to alterations
of intracellular pH. Temperature of incuba-
tion also influences production of secondary
metabolites; the effect of temperature
cycling (day/night temperature cycles ex-
perienced by plants in the natural environ-
ment) as a trigger of secondary metabolism
is a relatively unexplored area.
Addition ofExogenous Elicitors
Attack of cultured plant cells by micro-
organisms can induce the production of
antimicrobial secondary metabolites. The
microbe-derived molecules that stimulate
secondary metabolism have been called
"elicitors" and include glycan polymers,
glycoproteins, low-molecular-weight organic
compounds, and bacterial and fungal cell
walls. Abiotic elicitors include ultraviolet
irradiation, salts of heavy metals and vari-
ous chemicals. Fungal polysaccharides have
been used to induce alkaloids from Ruta
graveolens and phenylpropanoids from
Phaseolus vulgaris. Components of essential
oils, which are secondary metabolites pro-
duced by the degradation of fatty acids and
amino acids, possess antimicrobial activity.
The formation of essential oils may actually
be a defense against microbial attack and
produced in response to a microbial elicitor.
160 Source Book of Flavors

Induction of ceU differentiation for Catharanthus roseus for the produc-

If the above procedures are ineffective at
inducing secondary metabolite production,
it may be that cell differentiation is a re-
quired prerequisite. For example, essential
oils are not produced from suspension
cultures of lemon, peach, avocado, and mint
because the tissue lacks the oil glands that
are necessary for synthesis. Similarly,
volatile oils are not produced in undiffer-
entiated tissue cultures of a variety of herbs
(anise, fennel, and peppermint), celery or
onion. By manipulating the growth media,
calli can be induced to differentiate into
various organs, including roots or embryos.
Hairy root cultures have been established
tion of pharmacologically active indole
alkaloids. Some special problems, however,
are encountered when attempting to fer-
ment differentiated cell cultures in large
scale. Hairy roots are very sensitive to shear
stress and tend to adhere to the sides of the
fermentation vessel. Because mechanical
stirring cannot be used, nutrient and oxygen
gradients form in the vessel. Appropriate
bioreactor systems must be designed for
large-scale production of differentiated cell
cultures. Although the use of differentiated
cell cultures for the production of flavor
compounds is limited, some success has
been achieved. Flavor compounds have

TABLE 6-2. Biotransformation by Plant Cell Cultures

Substrate Product Cell type

Terpenoids
(-)-Menthol (-)-Menthol b-D-gentiobioside Eucalyptus perriniana
(+)-Menthol (+)-Menthol b-D-gentiobioside E. perriniana
(-)-Borneol (-)-Borneol b-D-gentiobioside E. perriniana
Alkaloids
(RS)-Reticuline (- )-(S)-Cheilanthifoline Papaver somniferum
(-)-Codeinone (-)-Codeine P. somniferum
14-Hydroxycodeinone 14-Hydroxycodeine P. somniferum

Amines
y-Glutamate Camellia sinensis
Ethylamine Theanine C. sinensis

Phenolics
(RS)-2-Phenylpropionic acid ~-D-Glucopyranosyl2-phenyl­ Dioscoreophyllum
propionate (glucosyl ester) cumminsii
Nicotiana tabacum
Carthamus tinctorius
Daucus carota
Panax ginseng
Ethyl 6-0-2-phenylpropionyl-b-D- Aconitum japonicum
glucopyranoside
6-0-2-Phenylpropionyl-D-glucose Glycyrrhiza echinata
~-D-Fructofuranosyl6-0-2-phenyl­ Coffea arabica
propionyl-a-D-glucopyranoside
(sucrose ester)
Phenylacetic acid Phenylacetic acid sucrose ester C. arabica
6-0-Phenylacetyl-D-glucose A. japonicum
Ethyl6-0-phenylacetyl-b-D- G. echinata
glucopyranoside
Tropic acid Tropic acid glucosyl ester N. tabacum
P. ginseng
Tropic acid sucrose ester C. arabica

Furuya (1988)
 Biotechnology for the Production of Flavoring Materials 161

been demonstrated to be produced follow- vaune

ing partial differentiation in certain herbs,
celery, onion, cocoa and peppermint. ~ L-Cystelne
Biotransformation of Flavor Precursors t
t
s-alkyi-L-cystelne sulfoxide
Callus and suspension cultures possess a allilnase
considerable potential for the formation of
secondary metabolites; however, the for-
mation of flavor compounds frequently fails +
Sulfenic acid
to occur. This may be due to the absence of
differentiated cells in cell cultures as dis-
cussed above. However, recent evidence
~
Thiosulfinate
indicates that in some cases the nonpro-
ducing cells contain the enzyme systems
necessary for formation of secondary
~
Thlosulfonate, mono-, di-, trlsulfides
metabolites. The apparent ineffectiveness FIGURE 6-2. Biogenesis of onion flavor. (Hong and
of the enzyme systems may result from Harlander 1989)
physical separation of substrates and
enzymes within the cell or inhibition of
specific enzymes in the pathway. Alterna-
Phenylalanine Valine
tively, the product may be degraded in situ
by oxidative systems.
The lack of end products of a pathway
does not exclude the possibility that in-
dividual enzymes within the metabolic
Ferulic acid Isobutyric acid
pathway are active. This has indeed been
demonstrated to be the case. As illustrated
in Table 6-2, suspension cultures can be
used to perform specific biotransformations.
Oxidation, reduction, glycosylation, esteri- Vanlllylamlne a-methyl 6-nonenolc acid
fication, methylation, isomerization and
optical resolution of racemic mixtures by
plant cell cultures have been observed.
Capsaicin
Onion Flavor FIGURE 6-3. Biogenesis of capsaicin. (Hong and
The proposed biosynthetic pathway for Harlander 1989)
onion flavor development is shown in Fig.
6-2. Limited success has been achieved with
generation of onion flavor by PTC. The studies using radioactive amino acids and
flavor in onion is produced from precursors cysteine derivatives confirmed the synthesis
that are hydrolyzed by the enzyme alliinase. of intermediates in the secondary pathway.
Cultured onion cells were not capable of
producing flavor compounds; however, Capsaicin Production
supplementation with precursors resulted in Capsaicin, the major component respon-
the generation of onion flavor, suggesting sible for the characteristic pungent flavor of
that the enzyme alliinase was present in the chili pepper, is synthesized from the amino
culture but that the pathways for synthesis acids phenylalanine and valine (Fig. 6-3).
of precursors were not functional. Further Extensive studies on capsaicin production
162 Source Book of Flavors
from callus and liquid suspension cultures
have demonstrated only very low levels
of production. Immobilization of cells
increased yields of capsaicin 2 to 3 orders of
magnitude higher than that produced by
liquid suspension cultures over a 5- or
10-day period. Addition of isocapric acid
or phenylalanine to immobilized cells or
suspension cultures also resulted in the
induction of capsaicin.
Vanillin Production
Natural vanilla flavor is produced from the
cured vanilla bean by a laborious and costly
procedure involving enzymatic and chemical
processes. There is a great deal of interest in
producing vanilla-like flavor compounds by
PTC and some commercial success has been
demonstrated. The metabolic pathway for
the production of the primary precursors of
vanilla flavor, vanillin and vanillic acid,
is well understood. Since this pathway is
generally very active in plant cell cultures, it
has been possible to produce vanillin by de
novo synthesis of vanilla PTC. Cells can be
Acid
f)
ATP, CoA
FIGURE 6-4. Biosynthetic pathway for ester production in strawberry fruits.
(Hong et al 1990)
immobilized for large scale production of
vanillin.
Strawberry Flavor
Strawberry (Fragaria ananassais) is one of
the most popular fruits because of its flavor
and scent. Over 200 volatile compounds
in strawberry have been identified. The
majority of these volatiles are esters,
organic acids, carbonyls, alcohols, lactones
and furans. The biosynthetic pathway for
ester production in strawberry is illustrated
in Fig. 6-4. Our laboratory has been inves-
tigating the development of a liquid sus-
pension culture system for production of
flavor and anthocyanin. Supplementation of
suspension cultures with short-chain fatty
acids and a-keto-acids as precursors resulted
in the formation of ethyl butyrate and butyl
butyrate; supplementation with a-keto-
valerate resulted in the formation of butanal
and butanol. No aroma compounds were
produced in unsupplemented or heat-
treated suspension cultures. The results
indicated that esterase, decarboxylase,
carbohydrates, amino acids, etc.
1 biosynthesis
alpha-keto acids
pyruvate decarboxylase
(TPP, Msf+)
(pH 6.0-6.5)
aldehydes
NAD(P)H ~
NAD(P) 2 ~ alcohol dehydrogenase (ADH)
alcohols
acyi-CoA ---1
+ esterase (pH 5.5-6.0)
ADP
esters
 Biotechnology for the Production of Flavoring Materials 163

and alcohol dehydrogenase might exist in Challenges in the Application of

strawberry cell cultures. PTC for Flavor Production
Despite the numerous applications of PTC
for the production of plant-derived flavor
Bioreactor Systems for Plant Cells
compounds, industrial applications have
been limited for the following reasons:
Although the growth of plant cells in sus-
pension culture is analagous to traditional
1. In contrast to microorganisms with cel-
bacterial fermentation systems, plant cells
lular doubling times of 20 to 40 min
offer unique challenges. The slow growth
plant cells grow slowly, with doublin~
rates and long fermentation cycles produce
times ranging from 20 to 200 hrs. Con-
a significant contamination problem for
sequently, the batch cycle time for plant
large-scale fermentation of PTC. Plant cells
cells can range from 15 days to 2-3
are sensitive to shear force; therefore,
months. It is difficult to maintain sterility
gentle mixing systems are required. More-
during these extended growth cycles.
over, secondary metabolites are present at
2. Relatively low volumetric yields are
relatively low concentrations and maximum
attained in most PTC systems when
production is not necessarily associated with
compared to microbial fermentations.
rapid growth of the cells. Culturing can
3. In most cases, the biosynthetic pathways
b~ accomplished in traditional stirred-jar
and regulatory mechanisms are not well
?wreactors as long as the agitation rate
understood in plant systems, and the
IS low: Airlift bioreactors are generally
optimum growth of plant cells does not
recogmzed as the most appropriate for plant
necessarily correlate with the maximum
cell suspension cultures because of the low
yield of secondary metabolites.
shear force. However, insufficient mixing at
4. Many secondary metabolites are pro-
low aeration rates or high cell densities can
duced following cell differentiation, and
be a problem. Rotating drum bioreactors
at the present time there is no universal
improve mixing properties and oxygen
trigger to uncouple chemical differentia-
transfer rates, and operate to cause signi-
tion from morphological differentiation.
ficantly less shear force than other bio-
5. The ability of plant cells to produce
reactor designs.
desirable metabolites may be lost or
An alternative to suspension cultures
regained during growth in cell culture
involves immobilization of plant cells.
making it difficult to control the stabilit;
Immobilization facilitates cell-to-cell con-
of PTC.
tact (partial structural organization), which
6. Low yields and ease of contamination
has been implicated as a potential factor in
result in higher production costs for
secondary metabolite production. Plant cells
manufacture of secondary metabolites
can be immobilized between membranes
using PTC. Economics of production are
or in hollow fiber bioreactors; covalently
the primary barrier to commercialization
bo~nd onto porous beads; or entrapped in
of PTC systems for flavor production.
algmate, agarose, agar, carrageenan or
gelatin. The major advantages of immo-
These challenges will need to be over-
bilized systems are the rate of nutrient
c?me if PTC i~ to become an economically
transport through the supporting material
VIable mechamsm for production of flavors
heterogeneity of microenvironments estab~
for the food industry.
lished within the bioreactor, and secretion
of intracellular secondary products into
the liquid phase where they can be easily
removed from the system.
164 Source Book of Flavors
FERMENTATION-DERIVED
FLAVORS
Microbial Production of Total Flavors
For thousands of years, products such as
cheese, yogurt, sausage, bread, wine and
beer have been produced, preserved and
flavored by means of microorganisms.
These classical fermentation systems lead to
the production of complex flavor composi-
tions as a result of microbial metabolism.
Certain of the lactic acid bacteria used for
the production of fermented dairy products
are capable of producing lactic acid and
the volatile compounds, diacetyl and
acetaldehyde. These compounds are pro-
duced during the fermentation as a result of
microbial metabolism and are responsible
for the characteristic buttery flavor and
aroma of certain fermented dairy products.
Diacetyl gives cottage cheese and butter-
milk their buttery aroma; acetaldehyde is
the important volatile of yogurt aroma.
Diacetyl and acetaldehyde are intermediate
products that undergo further catabolism
so their presence in the final product may
be reduced. A product that is a distillate
of the fermentation of milk or whey by
Lactococcus lactis subsp. diacetylactis is sold
commercially as starter distillate and can
be added to dairy products as a flavor
enhancer.
In addition to the generation of flavor
compounds, dairy starter cultures also
produce enzymes that break down the
protein (casein) and fat in milk, resulting in
the generation of peptides and various
chain-length fatty acids. These compounds
contribute to the flavor and aroma of dairy
products and are particularly important
during the aging process for Cheddar
cheese. Although fermented dairy pro-
ducts, as well as other fermented foods,
are characterized by microbially generated
flavors, the flavor-producing potential of
these organisms has rarely been systema-
tically analyzed or exploited.
Despite the literature containing numer-
ous references to the production of flavor or
aroma by microorganisms (Welsh, Murray
and Williams 1989), there are few if any
actual complete flavorings produced by
this approach. There are several reasons
for this. First, the aroma compounds are
typically present in the ppm levels. This
results in very uneconomical production and
recovery of the aroma (Scharpf et al. 1986).
Second, there are concerns for the legal
status of the organisms used in flavor gen-
eration. (If the organisms are not GRAS,
there is little probability of achieving FDA
approval to produce a flavoring material
using this organism.) Third, it is rare that a
flavoring suits the end customer without
substantial "tailoring." It would be very
difficult for the flavor company to change
the flavor profile of a flavoring made by a
fermentation to suit the customer. Thus,
there is a much stronger incentive for the
flavor industry to use fermentation to
produce individual flavor chemicals, which
then gives them the freedom to use each
chemical in many flavorings as well as tailor
make an individual flavoring to suit the
consumer.
Autolysates of Whole Cells
as Flavoring Agents
Autolysates or hydrolysates of whole cells,
particularly yeast cells, may be used as
flavor enhancers or flavorants, especially
as savory flavors. Yeast autolysates are
produced by the use of the cell's own
endogenous enzymes. These enzymes are
primarily carbohydrases and proteases that
rupture the cell walls and digest the cyto-
plasmic components. The digestion process
may be aided by heat, mechanical disrup-
tion, or addition of salt, sugar, or chemicals.
Spent brewer's yeast and baker's yeast are
often used as substrates for the production
of autolysates. Yeast may also be grown
on controlled media prior to hydrolysis to
product products with specific desired flavor
attributes. The flavor enhancement charac-
teristics of yeast autolysates are related to
the high concentration of glutamic acid,
 Biotechnology for the Production of Flavoring Materials 165

known for its meaty flavor characteristics
and flavor enhancement properties, in yeast
protein.
Microbial Production of
Pure Flavor Chemicals
Because of their size, metabolic diversity
and relatively simple growth requirements,
microorganisms (bacteria, yeasts and molds)
have been used commercially for the pro-
duction of a vast array of compounds, from
simple sugars and amino acids to relatively
complex proteins, polysaccharides, hor-
mones, pigments and flavors and aromas.
For many of these compounds, chemical
synthesis is not possible and living cells
possess the relatively complex metabolic
pathways essential for their biosynthesis.
The production of these compounds by
microorganisms is accomplished via fer-
mentation, usually a batch process in which
microorganisms are grown in large tanks or
vats (fermenters) on relatively simple and
inexpensive sources of carbon and nitrogen,
and sometimes vitamins, minerals or other
micronutrients. Flavors and aromas are
secondary metabolites usually present in
relatively low concentrations, and must be
purified and concentrated from the fer-
mentation broth. Compounds may be
produced inside the cell or secreted into
the medium; the operations required for
product recovery and purification are
somewhat simpler for substances that are
secreted.
Microorganisms naturally produce a large
number of chemicals that have pleasant
aromas or flavors. Some examples are pro-
vided in Table 6-3. Traditional mutation

TABLE 6-3. Microbiological Production of Aroma and Flavor Chemicals

Compounds Aroma/flavor notes Microorganism

Anisaldehyde Anise-like Trametes sauvolens

Benzaldehyde Almond-like T. sauvolens
Benzyl alcohol Fruity Phellinus igniarius
P. laevigatus
P. tremulus
Cinnamic acid methyl ester Fruity, jasmine Inocybe corydalina
Citronellol Rose-like Ceratocystis variospora
Trametes odorata
Citronellyl acetate Fruity, rose-like Ceratocystis variospora
Gamma-decalactone Peach C. moniliformis
Sporobolomyces odorus
Diacetyl Buttery Lactococcus lactis subsp.
diacetylactis
Ethyl benzoate Fruity Phellinus igniarius
Ethyl butyrate Fruity Lactobacillus casei
Pseudomonas fragi
L. diacetylactis
Geranial Rose-like Ceratocystis variospora
Linalool Floral C. variospora
Phellinus igniarius
Methyl benzoate Fruity P. tremulus
Methylphenylacetate Honey-like Trametes odorata
Methyl salicylate Wintergreen Phellinus igniarius
6-Pentyl-alpha-pyrone Coconut-like Trichoderma viride
Tetramethylpyrazines Nutty Corynebacterium
glutamicum
p-Tolualdehyde Almond-like Mycoacia uda
Neidleman (1989)
166 Source Book of Flavors

TABLE 6-4. Usage Level of Selected Flavor Compounds

Annual Usage
Compound (kg/annum) Organoleptic Note

ALIPHATIC COMPOUNDS
Acids
Lactic 1,395,240 Acidic
Stearic 79,728
Butyric 26,636 Cheesy
Alcohols
Glycerol 3,714,600
Isopropyl 72,118
cis-3-hexen-1-ol 4,847 Natural green topnotes
Esters
Ethyl butyrate 137,259 Fruity, pineapple
Isoamyl acetate 73,839 Strong fruity, banana
Ethyllaurate 34,881 Fruit
Ethyl propionate 34,881 Fruity odor, rum
Carbonyls
Acetaldehyde 147,687 Etheral, pungent
Acetoin 7,882 Pleasant, buttery
Diacetyl 25,368 Buttery
Others
Allyl isothiocyanate 15,311 Mustard-like
Eucalyptol 3,969 Characteristic odor
Maltol 4,524 Caramel-like
AROMATIC COMPOUNDS
Alcohols
Benzyl 71,121 Weak, slightly sweet odor
Esters
Methyl salicylate 139,977 Sweet, phenolic odor
Methyl anthranilate 27,768 Orange blossom odor
Methyl benzoate 4,847 Strong, dry fruity odor
Carbonyl
Vanillin 475,650 Vanilla
Benzaldehyde 156,738 Bitter almond
Cinnamaldehyde 141,366 Spicy odor, cinnamon
Phenylacetaldehyde 8,182 Sweet-green odor
Others
Eugenol 14,043 Spicy, clove odor
1-(4-hydroxy phenyl) 5,073 Sweet, fruity, raspberry
3-butanone

and selection techniques have been used
empirically to increase production levels of
desired flavor compounds. Mutations at
specific points in the metabolic pathway
may cause the accumulation of a metabolic
intermediate or may direct carbon flow
down an alternate pathway to products of
greater value. A mutation may decrease the
susceptibility of a microorganism to end
product inhibition with the overall result
being increased production. In addition,
fermentation and nutritional parameters can
be optimized to enhance productivity.
Industrial production of single flavor
 Biotechnology for the Production of Flavoring Materials 167

TABLE 6-4. Continued

Annual Usage
Compound (kg/annum) Organoleptic Note

TERPENES
Acyclic monoterpenes
Citra! 58,890 Strong, sweet lemon
Linalool 10,353 Light, sweet, fresh citrus
Citronella! 7,972 Sweet, rose-like
Cyclic monoterpenes
D-Limonene 68,403 Lemon-like
Menthol 44,348 Mint flavor
Carvone 20,702 Herbal or spicy mint
D-Camphor 19,075 Penetrating, minty

LACTONES
11-Dodecalactone 5,753 Peach-like
11-Decalactone 4,801 Intensely fruity, peach
y-Nonalactone 3,112 Coconut-like
Welsh et al. (1989)

TABLE 6-5. Microbially Produced Lactones

Microbe Lactones

Candida globiformis 5-Decanolide

C. pseudotrpoicalis
Ceratocystis moniliformis
Cledosporium butyri
lschnoderma benzionum
Pityrosporum sp.
Plyporus durus
Saccharomyces cerevisiae
S. fermenti
S. fragilis
Sporabolomyces odorus
Trichaderme viride
5-Decanolide
4- and 5-Decanolide
5-Decanolide
4-Butanolide, 4-pentanolide, 4-hexanolide, 2-hexen-4-
olide, 4-heptanolide, 2-hepten-4-olide, 4-octanolide,
2-octen-4-olide
4-Hexanolide, 4-heptanolide, 4-octanolide,
4-nonanolide, 4-decanolide, 4-dodecanolide,
4-dodecanolide
4-Butanolide, 4-pentanolide, 3-penten-4-olide,
4-hexanolide, 2-hexen-4-olide, 5-hexen-4-olide,
5-hexanolide, 2-hepten-4-olide, 4-heptanolide,
2-, 5-, and 6-octen-4-olide, 4-octanolide, 2-nonen-4-
olide, 2-decen-4-decanolide, 4-methoxy-6-methyl-
2H-pyran-2-one
5-Decanolide
4-butanolide, 5-ketohexan-4-olide
5-Decanolide
4-Decanolide, 5-decanolide, cis-7-decen-5-olide,
cis-6-dodecen-4-one
6-(pent -1-enyl)-a-pyrone, 6-pentyl-a-pyrone

compounds by microbial fermentation will be paid for a natural label. It seems

becomes economically feasible only when reasonable to focus on those chemicals for
there is high demand for a specific chemical, which one or more of these criteria apply
alternative sources and/or methods of when developing microbial fermentation
production are very expensive or a premium systems. Table 6-4 provides usage levels of
168 Source Book of Flavors
some important flavor compounds used in
the food industry. In many cases, micro-
organisms capable of producing these
compounds have been identified and
characterized. An excellent review by
Welsh, Murray and Williams (1989) pro-
vides numerous examples of specific flavor
compounds produced by microbial fer-
mentation. The following will discuss the
approach used for the production of some
flavor compounds via fermentation.
Lactones
Lactones are the character impact com-
pounds in coconut, peach and apricot
flavors. They also may play a significant role
in the flavor of many other food flavors
(e.g., heated dairy products). A number of
microorganisms will produce lactones;
however, the yields are generally low-
a few mg/1 or less (Table 6-5). While a
number of valuable lactones can be pro-
duced via microbial fermentations, the low
level of production severely limits their
commercial use. The exception is the use of
various Candida species for the biocon-
FIGURE 6-5. Lactone biosynthesis. (Murray et al 1988)
version of ricinoleic acid to 4-decanolide
(Okui, Uchiyama and Mizugaki, 1963).
Ricinoleic acid is the major fatty acid in
castor oil (80 percent). Candida species will
hydrolyze the ricinoleic acid from the tri-
glyceride and then via P-oxidation, degrade
it to 5-ketodecanoic acid (Fig. 6-5). The
yeast will reduce the keto acid to the cor-
responding hydroxy acid which can be
lactonized by dropping the pH and heating.
This process has been commercialized by
Farbood and Willis (1983) with claims of 5 g
lactone/liter fermentation.
Esters
A second area of commercial viability is the
production of esters by the yeast Candida
uti/is (Armstrong 1986). Candida uti/is was
found to ferment glucose to ethyl acetate
when grown on a medium limited in iron
(Fig. 6-6). In later work, they found that
ethanol could be converted into either ethyl
acetate or acetaldehyde, depending on the
initial concentration of alcohol (Fig. 6-7).
Armstrong (1986) postulated that the
acetyl-CoA formed from glucose or ethanol
?-keto-dodecanoic acid
5-keto-decanoic acid
I reduction
5-hydroxy-decanoic acid
5-decanolide
 Biotechnology for the Production of Flavoring Materials 169

~ 10.0
~ .0 ~ 0
c:
.Q .o" ---a-- g lucose (%wlv)
<G ·····IJJr··· ethanol
§
0 5.0 - -o-- A620
Ll.
----+-- acetic acid (10X)
0
:::> "'"""+"""' ethyl acetate
"0
0
ci:
0. 0 P-L.....--T='--r--.::!ir-:-.....-...,.---.----,- ..--...,.----.
0 2 4 6 8 10
Time (d)

sc:
glucose {% w /v)
ethanol
.Q
<G A620
§ acetic acid (10X)
0
Ll.
ethyl acetate
0
:::>

e
"0

Q._

0
0 2 4 6 8 10
Time (d)

100
"0
Q)
>= 80
(ij Ethyl Acetate
()
60 Ace taldehyde
~0
Q) 40
r.
1-
20
0
0~
0
0 2 4 6 8 10 12
Ethanol (giL)
FIGURE 6-7. Acetaldehyde production. (Armstrong et al1989)

could not enter the glyoxylate cycle when be limited, and thus the acetyl-CoA was
iron was limiting. The TCA cycle utilizes instead shunted into a reaction with ethanol
iron-containing enzymes (e.g., succinate to form ethyl acetate. Armstrong (1986)
dehydrogenase and aconitase) which would also found that when the level of ethanol
170 Source Book of Flavors
CH 3 - (CH 2 )4 -C-CH 2 -C-SCoA
CH 3-(CH 2k C-CH 2 -C-OH
FIGURE 6-8. Biosynthesis of the ketone, 2-heptanone. (Murray et a! 1988)
exceeded 3.5 percent, acetaldehyde accu-
mulated as the end product. He explained
this accumulation by noting that acetalde-
hyde is formed from ethanol before acetic
acid and thus will accumulate in the cell.
Acetaldehyde is known to inhibit acetyl-
CoA synthetase, which catalyzes the for-
mation of acetyl-CoA from acetic acid.
Therefore, higher levels of ethanol result in
higher levels of acetaldehyde, which in turn
inhibit acetyl-CoA formation and shuts
down ethyl acetate synthesis.
Ketones
Ketones are important contributors to
the flavor of cheeses, particularly the
mold-ripened cheeses (e.g., blue and
Camembert). Of the ketones, the C3 to C11
methyl ketones are of the greatest signi-
ficance. The methyl ketones are formed
from the lipids of milk fat through hydro-
lysis (lipase), ~-oxidation and addition of an
acyl group followed by decarboxylation to
yield a methyl ketone of one less carbon
(Fig. 6-8).
The production of blue cheese and
Camembert cheese flavors using submerged
Penicillium fermentation has been the
subject of several papers and patents (Jolly
! ~--00
II
CH 3 (CH 2) 6 -C-OH octanoic acid
0 0
II II
B-keto-octanyl CoA
I thioester hydrolase
0
II
t 0
II
B-keto-octanoic acid
! d--~
II
0
CH 3-(CH 3 )4-C-CH3 2-heptanone
and Kosikowski 1975; Watt and Nelson
1963; Dwivedi and Kinsella 1974; Kanisawa
and Itoh 1984; Okumura and Kinsella 1985;
Knight 1963; Luksas 1973). Blue cheese
flavor concentrates have been manufactured
using whey that has been supplemented with
fats, oils or specific fatty acids and fer-
mented with Penicillium roqueforti. Cheese
flavor concentrates containing up to 10
times the amounts of ketones normally
found in blue cheese have been produced in
this manner (Watt and Nelson 1963).
Aldehydes
Aliphatic, aromatic and terpenoid alde-
hydes are important contributors to the
flavor of many foods (e.g., fruits, fermented
dairy products and vanilla). Aldehydes are
typically synthesized by microorganisms as
intermediates in the formation of alcohols
from keto acids. While the aldehydes are
normally reduced to alcohols, the use of
fast-fermenting yeast strains, high fermen-
tation temperatures, the presence of readily
available nutrients and good aeration during
fermentation promote the accumulation of
aldehydes (Welsh, Murray and Williams
1989).
Most of the work on producing aldehydes
 Biotechnology for the Production of Flavoring Materials
via biotechnology has focused on the bio-
conversion of alcohols to the corresponding
aldehyde. An example of the bioconversion
of ethanol to acetaldehyde via Candida utilis
has been discussed earlier in this chapter
(section on esters). It is of interest that as
much as 13 g acetaldehyde/1 have been
achieved using a semicontinuous fermen-
tation process with Candida utilis (Murray
et al. 1988). Even higher concentrations
(35 g/1) of acetaldehyde have been produced
using P. pastoris (Duff and Murray 1988).
The alcohol oxidase system of P. pastoris
was found to have a low substrate specificity
and was active with the Cz-C6 primary
alcohols as well as benzyl alcohol. Since
both benzyl alcohol and benzaldehyde have
limited water solubility, only 5 g/1 benz-
aldehyde was formed in 17 hr. The low yield
of benzaldehyde was improved upon by
using purified alcohol oxidase and catalase
in a hexane bulk phase. In this system, 45 g/1
benzaldehyde was produced in 8 hr. (Duff
and Murray 1989).
Alcohols
Few alcohols are of flavor significance,
the exceptions being leaf alcohol (Cis-3-
hexenol) and 1-octene-3-ol (mushroom
flavor). Alcohols are more significant for
their role as precursors of esters. While the
production of alcohols via biotechnology is
reviewed by Welsh, Murray and Williams
(1989), a brief summary of work on pro-
ducing C8 alcohols (mushroom flavors) will
be presented.
The production of C8 alcohols by fungi
is quite common. Octan-3-ol, oct-1-en-
3-ol, and oct-1,5-dien-3-ol have been
found to be produced by Trichothecium
roseum (Vanhaelen, Vanhaelen-Fastre and
L-menthol L-menthylacetate
/!. {40%) (10%)
50%
L-menthone
~ D-neomenthol --+ D-neomenthyl glucoside
50% (5%) (glucosyl (45%)
transferase)
FIGURE 6-9. Pathway for conversion of L-menthone to L-menthol. (Tivedi 1986)
171
Geeraerts 1978). Penicillium caseiocolum
and P. camemberti have been found to
produce oct-1-en-3-ol, oct-1,5-dien-3-ol and
octan-3-ol (Karahadian, Josephson and
Lindsay 1985). It is suggested that these
alcohols are produced from their cor-
responding methyl ketones by various
dehydrogenases.
Production of L-menthol
The world demand for L-menthol is in
excess of 3,000 tons annually (Trivedi
1986). This flavorant is produced by Mentha
piperita and recovered by distillation. Dur-
ing the early flowering stage, L-menthone
is synthesized and is partially converted to
L-menthol (Fig. 6-9) as the plant reaches
full bloom. The final production of L-
menthol in the process reaches only about
40 percent of the potential since nearly 50
percent of the L-menthone is converted
to D-neomenthol and ultimately to D-
neomenthyl glucoside by a competing
enzyme system and an additional 25 percent
of the L-menthol is converted to L-menthyl
acetate. A strain of Pseudomonas putida
(YK2) has been shown to efficiently catalyze
the conversion of L-menthone to L-menthol.
This organism has been used to ferment
plants that have been harvested early when
high levels of the L-menthone are present
(Trivedi 1986). Thus, much higher yields of
menthol are obtained.
Schindler and Smith (1982) have re-
viewed the literature on using biotechnology
for the isolation of optically pure L-menthol
from the racemic mixture produced by
normal chemical synthesis. Ornata et al.
(1978, 1980, 1981) have accomplished
steriospecific hydrolysis of DL-menthol
succinate by Rhodotorula minuta var.
172 Source Book of Flavors
texensis. They immobilized the yeast and
used water-saturated hexane as the solvent.
Omuta et al. (1978, 1980, 1981) found a
conversion rate of 72.6 percent yielding
L-menthol of 100 percent optical purity.
The half-life of this system was estimated at
53-63 days.
Summary
Many of the processes reported in the
literature for flavor compound production
via fermentation are not commercially
feasible due to very low product yields.
Thus, while the literature contains a great
deal of information on the production of
flavor compounds via biotechnological
processes, few have commercial potential at
this time. In the case of the bioconversions
discussed in this chapter, one must recall
that the motivation to use these biocon-
versions is to produce a flavorant that is
"natural" by FDA definition. Therefore,
the starting material for the bioconver-
sion must be "natural" and available at
reasonable cost.
Overall, one must be concerned about
regulatory laws when considering bio-
technology and flavors. The incentives for
using this technology for flavor production
are the current labeling laws and FDA
guidelines for producing natural flavors.
The microorganisms that have been shown
to produce many flavor compounds are not
considered GRAS by the FDA, and their
use for this purpose may not be permitted.
TABLE 6-6. Major Enzyme Classes
Class
Hydro lases
Oxido-reductases
lsomerases
Transferases
Lyases
Ligases
Taken from Neidleman (1986)
Since substantial investment is required
in both research and production equip-
ment, the uncertainty of legal status is a
major obstacle to biotechnology for flavor
production.
Additionally, any change in the labeling
laws that removes the incentive for labeling
a product as "natural" would negate the
advantage of producing most flavor com-
pounds via biotechnology. The European
Community will be making such a change in
the labeling laws in 1992 and could provide
incentive for the U.S. to follow suit.
ENZYMATIC BIOCONVERSION
In microbial fermentation, substrates are
converted to products by enzymes present
within microbial cells. Enzymes are specific
proteins produced by living cells that
catalyze biochemical reactions. These bio-
catalysts, in crude or purified form, have
been widely used as processing aids in
the food industry. For example, enzymes
are used in cheesemaking (rennet, pro-
teases, lipases), wine and juice production
(pectinases), high fructose corn syrup
production (glucose isomerase), lactose
reduction (lactase), and aspartame pro-
duction (thermoase).
Enzymes are attractive catalysts for
large-scale production of flavors and fra-
grances as reactions can be carried out at
ambient temperature and physiological pH.
In addition, the high selectivities associated
Function
Hydrolysis of C- C, C- N, C- 0, etc. bonds
Oxidation-reduction involving oxygenation hydrogen atom
addition
Isomerization, racemizations
Transfer of acyl, sugar, phosphoryl, methyl, aldehydic,
ketonic or sulfur-containing groups from one molecule to
another
Addition to or formation of C = C, C = 0, C = N bonds
Formation of C- C, C- 0, C- S, C- N bonds with
ATP or other nucleoside triphosphate cleavage
 Biotechnology for the Production of Flavoring Materials 173

with enzymatic reactions are useful for desired flavor chemical transformations.
the production of enantiomerically pure Microbes known to possess specific enzymes
compounds. Enzymes can also be used as or enzyme pathways can be grown, har-
biocatalysts to convert natural, flavor- vested and suspended in an environment
less substrates to flavors and fragrances. that limits further growth. Addition of
Enzymes act on a number of different sub- precursor to resting cells and bioconversion
strates and carry out a vast number of to flavor compounds overcomes some of the
reactions, including esterifications, trans- limitations of pure enzyme systems. Living
esterifications, lactonizations and hydro- cells are capable of regenerating cofactors
lyses. Many of the flavor compounds listed required for certain enzymatic reactions,
in Tables 6-3 and 6-4 can be produced by as well as maintaining the proper redox
enzyme-mediated reactions. The major potential necessary for bioconversion and
enzyme classes are listed in Table 6-6. protecting enzymes and their cofactors from
Many enzymes, including lipases, ester- oxygen and trace metals.
ases, and proteases, mediate degradative There are, however, a number of limi-
processes; however, manipulation of the tations in the use of whole cells for bio-
reaction media can result in a shift of the conversion processes. Maintenance of
thermodynamic equilibrium to favor the viability and metabolic activity, and removal
synthetic capabilities of these enzymes. This of cells following the reaction, can be prob-
shift allows ester or peptide-linkage forma- lematic. In some cases, whole cells can be
tion and has been obtained through the use immobilized onto a matrix which helps
of nonaqueous organic solvent systems. stabilize the cells and eliminates the need to
Numerous organic solvent systems have remove them from the reaction system.
been developed for large-scale synthesis
of esters involving lipase- and protease-
Enzymatically Catalyzed
mediated esterifications (one such process
will be described in detail later in this Welsh, Murray and Williams (1989) have
section). provided a comprehensive review of flavor
There are some disadvantages in using production via enzymatically catalyzed
pure enzymes for production of flavor com- reactions. Therefore, only a sampling of the
pounds. Enzymes are frequently unstable literature will be discussed below.
and are subject to inactivation by chemical, Armstrong, Gillies and Yamazaki (1989)
physical and biological factors. Many have published a summary of their efforts
enzymes require cofactors, such as NAD or
an energy-rich substrate such as ATP, which TABLE 6-7. Ester production by immobilized C.
are difficult to regenerate. Enzymatic cylindracea lipase using a range of
reactions are slower than chemical reactions substrates
and yields are frequently lower. Enzymes
Ester (M) Conversion
are frequently used in batch processes
where they cannot be recovered and used Ethyl propionate 0.19 76
again, making their use relatively expen- Ethyl butyrate 0.25 100
sive. This limitation can be overcome by Ethyl hexanoate 0.09 44
Ethyl heptanoate 0.21 84
immobilizing enzymes onto solid surfaces;
Ethyl octanoate 0.26 100
immobilized enzymes can be used over Ethyllaurate 0.13 52
and over again in continuous processes, Ethyl isobutyrate 0.18 72
which are much less expensive than batch Ethyllsovalerate O.oi 3
reactions. Isobutyl aectate 0.06 25
An alternative to using isolated enzymes Isoamyl acetate 0.06 24
Isoamyl butyrate 0.22 91
is the use of whole cells to accomplish the
174 Source Book of Flavors
I References
I Anonymous. 1987. Bioprocess. Techno/. 9(9):6.
NON-POLAR SOLVENT /
/ WATER
ESTER._ /
ACID/._/~
ALCOHOL-/ ~ RS
I Berger, R.G. and Drawert, F. 1987. Biotech-
I nology in flavour research: achievements,
LIPASE
ESTER + H20 ~~ ALCOHOL + ACID
FIGURE 6-10. Production of esters in a non-
aqueous lipase system. (Armstrong et al1989)
to produce esters using enzymatically
catalyzed reactions. They have immobilized
lipase from C. cylindracae and used water-
saturated heptane as the solvent. The
conversion efficiencies of various alcohols
and acids to their corresponding esters is
presented in Table 6-7. The conversion rates
are generally quite good. This work pro-
vides an example of how the functioning of
an enzyme may be dramatically altered
when it is placed in a nonaqueous solvent.
Lipases normally function to hydrolyze
esters rather than form them. Yet in this
nonaqueous solvent they formed esters very
efficiently from alcohols and acids. Arm-
strong, Gillies and Yamazaki (1989) explain
this change in functioning due to the re-
versal of the equilibrium when operated in a
nonaqueous system (Fig. 6-10). As esters
are formed, they migrate into the heptane
phase away from the water-saturated en-
vironment of the enzyme. Alcohols and
acids are more soluble in the water-saturated
enzyme environment and thus concentrate
near the enzyme. Armstrong, Gillies and
Yamazaki (1989) cited some studies where
supercritical C0 2 was used as the solvent.
They observed extremely rapid reaction
rates (270-fold increase relative to the same
enzyme in an aqueous system). This plus the
advantage of simple recovery from the
extracting solvent makes C02 a good choice
in the future.
Armstrong, D.W., Gillies, and Yamazaki, H.
1989. Natural flavors produced by biotech-
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Trends and Developments, ed. R.G. Buttery,
F. Shahidi, and R. Teranishi, pp. 105-120,
Washington D.C.: American Chemical
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needs and perspectives. In: Flavour Science &
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Wiley & Sons.
Drawert, F. 1990. Impact-compounds and stra-
tegies for their biotechnological synthesis.
Food Biotechnol. 4(1):25-37.
Duff, S.J.B. and Murray, W.D. 1988. Production
and application of methylotrophic yeast
Pichia pastoris. Biotechno/. Bioeng 31:44.
Duff, S.J.B. and Murray, W.D. 1989. Oxidation
of benzyl alcohol by whole cells of Pichia
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and nonaqueous reaction media. Biotechnol.
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Dwivedi, B.K. and Kinsella, J.E. 1974. Con-
tinuous production of blue-type cheese flavor
by submerged fermentation of Penicillium
roqueforti. J. Food Sci. 39:620.
Farbood, H. and Willis, B. European Patent No.
PCT 100072, 1983.
Furuya, T. 1988. Production of useful com-
pounds by plant cell cultures-de novo
synthesis and biotransformation. Yakugaku
Zasshi 108(8):675-696.
Gatfield, I.L. 1986. Generation of Flavor and
Aroma Components by Microbial Fermen-
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In Biogeneration of Aroma, eds. T.H. Par-
liment and R. Croteau, pp. 310-322. ACS
Symposium Series #317. Washington D.C.:
American Chemical Society.
Hong Y.C. and Harlander, S.K. 1989. Plant
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Champaign, IL: American Oil Chemists'
Society.
Hong, Y.C., Huang, L.-C., Reineccius, G.A.,
Harlander, S.K., and Labuza, T.P. 1990.
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Cult. 21:245-251.
Jolly, R. and Kosikowski, F.W. 1975. Blue
cheese flavor by microbial lipases and mold
spores utilizing whey powder, butter and
coconut fats. J. Food Sci. 40:285.
Kanisawa, T. and ltoh, H. 1984. Production of
methyl ketone mixture from lipolyzed milk fat
by fungi isolated from blue cheese. Nippon
Shokuhin Kogyo Gakkai-Shi. 31:483.
Karahadian, C., Josephson, D.B., and Lindsey,
R.C. 1985. Volatile compounds from Penicil-
lium sp. contributing musty-earthy notes to
Brie and Camembert cheese flavors. J. Agric.
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Knight, S. U.S. Patent No. 3,100,153. 1963.
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Chapter 7
Natural Flavoring Materials
Foods and other processed consumable
products are formulated to have, among
other desirable attributes, an attractive
flavor. This is achieved by the use of ingre-
dients that are either intrinsically flavorful
or produce flavors during the processing or
cooking, supplemented as necessary by the
addition of flavorings or of materials that
stimulate the sense of taste (e.g., salt,
sweeteners, acidulants and bittering agents),
or produce other gustatory effects (e.g.,
pungent spices, etc.).
Many plant materials are excellent sources
of flavors and are either used directly in
food products or processed to recover their
aromatic constituents in a more convenient
form for incorporation into flavorings (see
Table 7-1 for the processing of plant ma-
terials). Plant materials contain both volatile
and nonvolatile constituents, which affect
their odor and/or flavor profiles as well as
their sensory impact. The volatile constitu-
ents are what gives to the plant its distinctive
odor, whereas the nonvolatile constituents
are either inert (e.g., cellulose) or influence
some gustatory reaction (e.g., bitterness,
pungency, astringency, etc.) sometimes
coupled with a physiological effect (e.g.,
coffee, cocoa leaves). The intensity and qual-
ity of these effects show very wide variations
176
between plant families and species. Al-
though, qualitatively, the specific aromatic
profiles remain recognizable and within
acceptable limits, a quantitative variation is
often observed between different crops and
batches of the same plant material and also
between the various parts of the plant that
may be used. Because of this variation it
is difficult to be precise in describing the
aromatic effects of plant materials, and
assessment is generally a matter of judg-
ment of acceptability for a particular use.
Classification
Classification of plant materials has been
discussed by Arctander (1960), who con-
cluded that an obvious botanical classifica-
tion produces too many anomalies, several
sensory misalliances and the loss of many
related aromatic effects. For practical pur-
poses, it is better to consider plant materials
in the groups best recognized by the flavor-
ist, and bring together those plants having
some odor or flavor relationship (Heath
1978, 1981). Arctander devised a sensory
classification based on 88 groups with cross-
references to other related groups. This
involved a vocabulary of terms describing
odor types.
 Natural Flavoring Materials 177

TABLE 7-1. Natural raw materials and flavoring products

Source Prime Process/Products Secondary Process/Products
Alliaceous vegetables Mechanical extraction Evaporation (open or under vacuum)
Cocoa Citrus peel oils Fruit juice concentrates
Coffee Fruit juices Fruit pastes
Fruits (citrus, stoned Distillation Soft extracts
or soft) Essential oils Dehydration
Herbs and spices Co-distillation with alcohol Dried herbs
Mushrooms/fungi Aroma distillates Fruit powders
Nuts Essences Re-distillation or fractional
Resins Extraction with solvents distillation
Vanilla (a) Solvent remains in product Concentrated essential oils
Vegetables Decoctions Terpeneless essential oils
Other plant materials Tinctures Isolates
Essences Adsorption on silica gel
(b) Solvent completely removed Terpeneless citrus oils
Oleoresins
Extracts
Concretes/ absolutes

Merory (1968) adopted a much simpler
sensory classification. This has been mod-
ified and elaborated (as shown in Table 7-2)
to introduce the idea of sensory impact with-
out attempting to produce a precise group-
ing of similar attributes.
References relating generally to the topics
covered in this chapter are presented here.
References pertaining to specific flavoring
materials (but not necessarily used in the
text) are provided at the end of each section
that follows.
References: General Flavoring
Arctander, S. 1960. Perfume and Flavor Ma-
terials of Natural Origin. Steffen Arctander,
Elizabeth, N.J.
Ashworth, P.R. 1990. Food Flavorings. New
York: Van Nostrand Reinhold.
Bremness, L. 1988. The Complete Book of Herbs.
New York: Viking Studio.
British Herbal Medicine Association. 1990.
British Herbal Pharmacopoeia. London:
Dorset.
Budavari, S., O'Neil, M.J., Smith, A., and
Heckelman, P.E. 1989. The Merck Index: An
Encyclopedia of Chemicals, Drugs, and Bio-
logicals. Eleventh Edition. Rahway, N.J.:
Merck & Co., Inc.
Committee on Codex Specifications. 1981. Food
Chemicals Codex. 3rd Edition. Washington,
D.C.: National Academy Press.
E.O.A. 1976. Essential Oil Specifications and
Standards. New York: Essential Oil Associa-
tion of U.S.A.
Furia, T.E. and Bellanca, N. 1975. Fenaroli's
Handbook of Flavor Ingredients, 2nd Edition,
Vol. 1 and 2. Cleveland: C.R.C. Press.
Gildermeister, E. and Hoffman, F.R.1965-1967.
The Essential Oils, Vol. I- VII. Akademie-
Verlag, Leipzig, E. Germany. (German)
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. D. New York: Van Nostrand Co.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. New York: Van
Nostrand Reinhold.
Heath, H.B. 1981. Source Book of Flavors. West-
port: Van Nostrand Reinhold.
Hui, Y.H. 1991. Encyclopedia of Food Science
and Technology. New York: Wiley.
Kirk, R.S. 1991. Pearson's Composition and
Analysis of Foods. 9th Edition. New York:
Wiley.
Merory, J. 1968. Food Flavorings, 2nd Edition.
AVI Publishing Co., Westport, Conn.
Pharmaceutical Society of Great Britain. 1979.
The Pharmaceutical Codex. London: Phar-
maceutical Press.
Prakash, V. 1990. Leafy Spices. Boca Raton,
Fla.: CRC Press.
Stobart, T. 1982. Herbs, Spices and Flavorings.
Woodstock, Vt.: Overlook Press.
United States National Formulary, 15th Edition.
1980. Washington, D.C.: American Pharma-
ceutical Association.
United States Pharmacopoeia, 20th Edition.
1980. Rockville, Md.: United States Phar-
macopoeial Convention.
178 Source Book of Flavors

TABLE 7-2. Classification of plant materials using sensory impact as a factor

AROMATIC Cinnamon bark Benzaldehyde-like

Coriander Almond, bitter
Strong Impact Licorice root Apricot kernel
Warmly Aromatic Cherry bark, wild
Manna
Angelica root/seed Vanilla Peach kernel
Calamus root Plum kernel
Sweetly Camphoraceous
Chamomile, Roman Coumarin-like
Sweet basil
Lovage root Tarragon (estragon) Tonka bean
Valerian Woodruff
Anisic
Zedoaria Anise Alliaceous/sulphurous
Sweetly Balsamic Asafetida
Basil
Juniper Garlic
Fennel
Laurel berry Star Anise Leek
Myrtle Onion
Carvone-like
Spicy Caraway
Celery seed BITTER
Dill
Cubeb Strong
Spearmint
Cumin Agaric
Cineolic
Dalmatian sage Aloe
Bay laurel leaf
Sassafrass Chiretta
Rosemary
Turmeric (curcuma) Quassia wood
Spanish sage
Thymol-like Wormwood
Phenolic
Ocimum spp. (thymol type) Bay leaf, West Indian Medium
Savory Cinnamon leaf Centuary herb
Thyme Clove bud/leaf/stem Colomba root
Mentholic Pimento (allspice) Holy thistle
Mentha arvensis Cinchona bark
Peppermint Mild Impact Simaruba bark
Woody Sweetly Floral
Elecampane root Arnica flower Mild
Pimpinella root Chamomile, German Angostura bark
Peppery /pungent Elder flower Cascarilla bark
Black pepper Guaiac wood Curacao peel
Capsicum Lavender Hop
Galanga root Orris root Orange peel, bitter
Ginger Tansy Yarrow
Grains of Paradise Citrus STIMULANT
Grapefruit
Medium Impact Coffee
Lemon
Sweetly Aromatic Cola nut
Lime
Cardamom Tea
Orange
Carob Tangerine (Mandarin)
Cassia bark

ALLIACEOUS FLAVORS related to the alliaceous vegetables, asa-

The alliaceous group of flavoring materials is
of particular interest. It includes several very
well-known plants, the tuberous rootstocks,
bulbs and, in some cases, the leaves of which
are used in food for nutritional, textural
and flavoring purposes. The most important
members of this group are chives, garlic,
leeks and onion. Although not botanically
foetida also has a strong alliaceous char-
acter and is considered in this group. (See
Fenwick and Hanley 1985a,b).
Asafoetida
Gum asafoetida is an oleo-gum-resin exu-
date from the fleshy rhizomes and stems of
 Natural Flavoring Materials 179

Ferula asa-foetida L., F. foetida (Bunge) and F. rubricaulis (Boiss., which is used
Regel, F. rubricaulis Boiss., and probably medicinally.
others of the 60 or so species of Ferula, Some commercial samples, often in the
members of the Umbelliferae that grow in form of a paste, may consist of gum mixed
Afghanistan, N.W. India, Iraq and Turkey. with various diluents such as gypsum, cereal
It has a strong, persistent, alliaceous odor flours, etc. The genuine material should
with a warm sweet balsamic undertone and contain 40-64 percent resin consisting of
a characteristic bitter back-note, which is asoresino-tannol both free and combined
not disagreeable in dilution but in its natural with ferulic acid, 25 percent of gums, and
form is objectionably strong. 6-19 percent of essential oil. Raghavan et
The plants grow from a perennial root- al. ( 1974) studied 17 commercial samples
stock to a height of 1.5 to 3m. Numerous and published analytical data for both genu-
schizogenous ducts in the cortical tissues ine and compounded materials; the follow-
contain a milky emulsion that exudes when ing data are presented in Table 7-3.
the plant is cut. The oleo-gum-resin is ob-
tained as a translucent exudate by cutting Oil ofAsafoetida
off the stems close to the crown; the juice The volatile oil obtained by distilling gum
hardens and is scraped off. The commercial asafoetida is of little commercial value, al-
gum is usually contaminated with pieces of though small lots are available.
stem, sticks, earth and other extraneous filth.
Gum asafoetida occurs as opaque grayish- Constituents
white or yellowish translucent rounded or Very little work has been carried out to
flattened tears, 12 to 25 mm in diameter and establish the chemical composition of oil
often in agglomerate masses. Raghavan et of asafoetida. Guenther (1948-1952) re-
al. (1974) recognize 17 species of Ferula as ported the presence of the following com-
of commercial importance. The trade classi- pounds: pinene, 2-butyl propenyl disulfide
fies these into two main types: Asafoetida (about 40 percent), several disulfides with
hing- derived mainly from F. alliacea Boiss., boiling points between 92-127°C (about
F. narthex Boiss. and F. asa-foetida L., used 20 percent) said to be responsible for the
mainly in flavoring, and Asafoetida hingra- disagreeable odor, diallyl disulfide and
obtained from F. foetida (Bunge) Regel, about 20 percent of an unidentified com-
ponent. Later work by Abraham et al. (1982)
demonstrated the presence of three major
TABLE 7-3. Analytical data for genuine and com- disulfides: 2-butylpropenyl disulfide, 2-
pounded gum asafoetida commercial butyl-3-methylthioallyl disulfide, and 1-(1-
samples methylthiopropyl) 1-propenyl disulfides.
Genuine Compounded Rajanikanth, Ravindranath and Shan-
% % karanarayana (1984) have also identified
dimethyl trisulfide, 2-butyl methyl disulfide,
Moisture 5.0-13.7 7.0-18.0 2-butyl methyl trisulfide, di-2-butyl disulfide,
Total ash 4.3-29.4 1.1-9.2
Acid-insoluble ash 0.4-9.0 0.1-6.1
di-2-butyl trisulfide, di-2-butyl tetrasulfide
Starch 1.8-20.1 5.2-61.8 and di-1-butyl trisulfide. Some effort has
Sulfur 3.3-12.3 2.8-7.8 focused on terpenes and numerous have
Extractives in: been identified to date (Ashraf and Bhatty
Ethanol 10.0-74.2 1.7-49.8 1979). Lawrence (1985) has reviewed the
Acetone 5.1-64.2 1.0-52.0 research related to flavor compounds in this
Petroleum ether 2.3-7.8 0.5-29.9 product.
Ethylene dichloride 7.8-76.8 1.7-50.0
Volatile oil 8.2-19.6 0- 8.2
180 Source Book of Flavors

Chives Flavoring Forms

Chives used in food as a flavoring and as a
Dehydrated Garlic Powder
garnish are the hollow thin green stems of
It is a cream to creamy /white powder pre-
the alliaceous bulb, Allium schoenoprasum
pared by the dehydration of selected cloves
L. The plant grows wild throughout northern
of garlic, and has a strongly persistent and
Europe, Canada and northern United
characteristic odor and flavor when rehy-
States, but is most widely cultivated as a
drated. The flavor character is retained well
pot herb. It has a pleasantly delicate onion-
on storage but, as garlic powder is very
like flavor, which is strongest in the young,
hygroscopic, containers should be kept well
freshly chopped leaves. The flavor is lost on
closed or the product becomes hard and
dehydration, but can be retained for several
lumpy and loses its flavoring strength. The
months under frozen storage. Hashimoto,
comparison of flavor level between fresh
Miyazawa and Kameoka (1983) and Kallio
and dehydrated garlic is approximately 1 : 5.
et al. (1990) have reported on the flavor
Garlic powder is widely used in some types
volatiles in chives.
of European dry sausages, salami, etc., and
if used with discretion, it produces a distinct,
Garlic pleasing and not overpowering flav_or .. The
dehydrated product is not necessanly tdeal
Garlic has been used as a food and medici-
as a flavoring, since many of the finer aro-
nally for all of recorded history. It is ~he
matic components are lost during dehydra-
compound bulb of Allium satiuum L., ~htch
tion, the overall profile changes due to
comprises numerous small hard whtte or
partial caramelization of the sugars present,
pale pink- to mauve-skinned bulbs, gener-
and the enzymatic potential for producing
ally known as "cloves," enclosed within a
further aromatic constituents is reduced
white membranous outer casing. The num-
(Moreira-Hernandez, Villegas and Cabrera,
ber and size of the individual cloves are
1986 and 1987). Garlic powder tends to have
variable as is the flavor, ranging from mild
a "boiled" note that is not present in the
and sweet to almost overpoweringly strong
fresh material.
and pungent, depending on the variety and
source. Garlic is grown universally in tem-
perate regions and is available commerciall~ Garlic Salt
as the dried bulb, which has little odor until This is a mixture of garlic powder and salt;
crushed or cut (Carson 1987). an anticaking agent such as starch or trical-
Garlic contains about 0.1 to 0.25 percent cium phosphate may be present to maintain
of volatile constituents, formed enzymatic- free-flowing properties. Standardized dis-
ally when the cloves are crushed; these can persions of garlic oil (usually at 0.1 to 0.25
be recovered as so-called oil of garlic by percent) on salt or other suitable edible
distillation. The flavor of garlic is widely carriers are also available for use in blended
appreciated in cooking, but it sh_ould be seasonings and are generally preferred.
remembered, particularly by those mvolv~d
in any kind of sensory assessment, that tts
Encapsulated Garlic Flavors
odor is very persistent, may taint the breath
These are generally spray-dried products
long after its ingestion, and be objectionable
containing garlic oil and/or garlic oleoresin
and distracting to others taking part in any
or extract encapsulated either in gum acacia
sensory evaluation.
or a modified starch. The flavoring strength
of these products depends on the manu-
facturer and range from equal to 10 times
stronger than that of garlic powder.

Oil of Garlic
This is obtained by the distillation of crushed
fresh garlic cloves.
Specification in EOA No 180, FCC III
(1981) A reddish-orange oil; specific grav-
ity (25° /25°C) 1.040 to 1.090; refractive index
(20°C) 1.5590 to 1.5790. The EOA specifica-
tion points out the importance of the sen-
sory quality of this oil.
Constituents Garlic oil contains allyl
compounds that are absent from onion oil.
Brodnitz (1971) reported that diallyl thiosul-
finate is the major component in solvent-
extracted garlic and that this compound is
the source of the following constituents: allyl
alcohol (5.4 percent), methyl allyl disulfide
(1.2 percent), diallyl disulfide (5.7 percent),
dimethyl trisulfide (2.4 percent), methyl allyl
trisulfide (1.5 percent), diallyl trisulfide (1.0
percent), and, in addition, two fractions
(representing about 78.9 percent) of the ex-
tract were investigated by NMR and thought
to be diallyl disulfide (66 percent), diallyl
sulfide (14 percent) and diallyl trisulfide (9
percent). Garlic oil constituents have been
reviewed by Whitaker (1976), Block (1985)
has discussed the chemistry of onion and
garlic, Maarse and Visscher (1989) and Whit-
field and Last (1990) have presented over-
views on the volatiles in garlic. Garlic has
received substantial attention in the research
community since it has been proposed to be
an anticarcinogen.
Oleoresin Garlic
This is a dark brown soft extract prepared
by the vacuum concentration of the ex-
pressed juice and the aqueous extraction of
the press-cake. It contains about 5 percent
garlic oil. The flavoring strength is about
two to three times that of fresh garlic and
eight times that of garlic powder, although
the determination of these equivalents is
very difficult other than directly in an end-
product.
Leek
Leek (Allium porrum L.) is popularly re-
garded more as a very flavorful vegetable
Natural Flavoring Materials 181
than as a source of flavor per se. It is widely
eaten throughout Europe and Canada, but
is less popular in the United States. The
plant is a biennial having a thick bulbous
base and tightly packed leaves, which form
the fleshy "stem" of the vegetable. The inner
leaves and the lower parts of the outer leaves
are etiolated by exclusion of light during
growth. The flavor is much more delicate
than onion and has a pleasant green charac-
ter. The American wild leek is Allium
tricoccum L.
Leek Oil
Obtained by the distillation of freshly crushed
whole leek in a yield that may vary widely
between 0.005 and 0.02 percent, depending
on the wetness and maturity of the vege-
tables at the time of distillation. Schreyen et
al. (1976) identified 67 components in steam-
distilled leek oil and concluded that propane-
thiol, allyl methyl sulfide, methyl propyl
sulfide, dipropyl disulfide and methyl propyl
trisulfide had distinctive leek-like odors.
Coley-Smith (1986) has done additional
work on leek flavor.
Onion
One of the oldest known and most important
of the alliaceous vegetables is the bulb of
onion, Allium cepa L. This is grown as a
commercial crop in Egypt, Japan, the United
States (California, Texas and New York)
and, to a lesser extent, in most European
countries and Mexico. The hollow tubular
leaves die at the end of the growing season,
leaving a hard-fleshed bulb with a thin outer
scaly layer. The shape may be oblong, flat,
globe or oblate, and the color brown, white
or red depending on the variety and source
(Carson 1987).
Onion is a biennial, although the common
variety is grown as an annual propagated
either from seed or from small bulbs called
"sets." The Egyptian onion (A. cepa var.
vivaparum) produces small bulbs or top-sets
in the flower head.
There are many varieties of A. cepa,
182 Source Book of Flavors
which are classified according to their dry-
solids content and pungency. Many com-
mercial crops are raised specifically from
cultivars to satisfy market requirements (i.e.,
domestic use, pickling, canning, dehydra-
tion, etc.), with care being necessary during
their husbandry as the plants are liable to be
attacked by several diseases affecting qual-
ity and keeping properties.
Onions have little smell until the tissues
are cut or bruised. Once this takes place, the
enzymatic reaction results in a complex mix-
ture of sulfides that may be recovered as so-
called "oil of onion" by distillation. The
amount recoverable depends on the variety
and ripeness of the onions used, but averages
0.02-0.03 percent.
F favoring Forms
Dehydrated Onion
The dehydration of onions to produce onion
powder and pieces of various sizes is now a
major activity in California, Japan, Egypt
and some central European countries. The
onions are first flame peeled, washed to
remove the burnt outer skin, and then
mechanically sliced onto a perforated belt.
The drying is carried out in a tunnel drier,
the hot air circulating through the holes in
the conveyor belt. Onions enter the system
with a moisture content of about 80 percent
and are dehydrated to about 4 percent. The
dehydrated product may be sold as such,
kibbled to various mesh sizes, or milled to a
moderately fine powder. All of these prod-
ucts, particularly onion powder, absorb
moisture and must be packed and retained
in well-closed containers preferably having
an impervious liner.
Onions are dehydrated without blanching
so that they retain their essential flavoring
character. As a consequence, the products
usually have a high microbiological count
due to the presence of thermophilic spores
that survive the drying temperature. The
nature of these bacteria was investigated by
Vaughn (1970), who concluded that no single
microbial index for onion and garlic prod-
ucts was possible, and that specifications
for microbiological quality should reflect the
end use as well as defining the test method
used.
Several methods have been proposed for
the assessment of the flavoring strength and
pungency of both fresh and dehydrated
onions. There is good correlation between
the enzymatically produced pyruvic acid,
odor strength and pungency (Carson 1987).
The relative flavor strength of fresh and
dehydrated onion is difficult to determine,
as the two profiles are quite different. How-
ever, it is generally accepted that onion
powder is about ten times stronger than
fresh onion.
Toasted Dehydrated Onion
Onions contain reducing sugars whose quan-
tity present depends on the variety and/or
conditions of storage. These may undergo a
Maillard reaction during the latter stages of
dehydration unless the drying temperature
is successively reduced as the pieces pass
through the tunnel drier. High temperatures
result in an over-brown product having a
marked toasted note. There is a demand for
toasted onion products that have the odor
and flavor associated with sauteed onions.
They are available in both powder and kib-
bled form in qualities ranging from lightly
to heavily toasted. Manufacture is from al-
ready dehydrated onion by further heat pro-
cessing at 100° -175°C (212°- 350°F) for
periods up to 30 hr.
Some onion varieties (e.g., White Sweet·
Spanish, Southport White Globe) may readi-
ly be toasted to produce uniformly colored
and flavored products. Other varieties (e.g.,
Creole) give excellent pale-colored dehy-
drated onion, but are unsatisfactory for
toasting. This is due to variations in the
content of reducing sugars; the low sugar
content varieties (8-10 percent dry weight)
are hard to toast, with the high sugar con-
tent types (30-45 percent dry weight) prod-
ucing the best products. In some onions, the
reducing sugars are unevenly distributed so
the resulting toasted products are unevenly

colored. Spraying the dehydrated difficult-
to-toast material with the juice of easy-to-
toast onions is suggested as a method of
overcoming this problem.
Onion Salt
This is a mixture of onion powder and salt,
often with an anticaking agent such as starch,
tricalcium phosphate or silicon oxide, to
maintain dry free-flowing properties. Stan-
dardized dispersions of onion oil, with or
without onion extract, are available for use
in blended seasonings. The flavoring strength
of these products should be determined from
the manufacturer.
Encapsulated Onion Flavors
Onion oil encapsulated by spray drying in
gum acacia or a modified starch is available
as a flavoring ingredient. The strength of
these products depends on the manufacturer
and may range from equal to ten times
stronger than onion powder.
Onion Juice/Extract (Oleoresin)
Onion juice carries all of the available flavor,
actual and potential, and is a good basis for
the preparation of a water-miscible onion
flavoring. The juice is obtained by hydraulic
pressing of the washed onions. This presents
some difficulties, owing to the flat laminate
cellular structure that tends to make the
tissues slide rather than rupture. To obtain
a good recovery it is usually necessary to
employ multiple pressings with adequate
water washing. Even when the expression
is apparently complete, the dry press-cake
may still yield a further quantity of extractive
after boiling with water.
Normally, the freshly recovered juice is
flash heated at 140°-160°C and immediately
cooled to 40°C. This ensures its preservation
until sufficient bulk is available for concen-
tration in a vacuum falling-film evaporator
to a product having a minimum of 75 per-
cent dry solids. At this concentration, the
concentrated juice is pale-brown in color,
has a strong fresh-onion odor, and a sweetish
Natural Flavoring Materials 183
flavor free from the bitterness present in the
unheated juice.
The concentrated juice may be further
evaporated in a vacuum stirrer-pan until the
dry solids content is 80-85 percent. The
additional heat applied induces further non-
enzymatic browning, the resulting product
being a soft dark-brown extract having a
markedly cooked/toasted onion character.
For uniformity and ease of handling, this
extract may be mixed with propylene glycol,
lecithin and glucose to give a stable, semi-
fluid, so called "oleoresin onion" that may
be up to ten times stronger than the flavor of
onion powder. By altering the base material,
an oil-dispersible version is possible.
Oil of Onion
This is obtained by the distillation of crushed
fresh onions that have been allowed to stand
for some hours before distillation. As onion
oil constituents are partially water-soluble, a
special recovery technique is necessary to
achieve a high-quality oil in a yield of about
0.02 to 0.03 percent, depending on the type
of onion and the season.
Specification in EOA No 183, FCC ll1
(1981) An amber-yellow to deep-amber
oil; some samples may show a crystalline
deposit; specific gravity (25° /25°C) 1.050 to
1.135; refractive index (20°C) 1.5495 to
1.5695. The EOA specification points out
that the sensory quality of this oil is of more
importance than physical characteristics.
Constituents The chemical composition
of onion oil, obtained either by direct dis-
tillation of the crushed bulbs or from the
expressed juice, has been the subject of
many studies (Carson and Wong 1961;
Brodnitz and Pollock 1970; Boelens et al.
1971; Whitaker 1976; Freeman and Wenham
1975; Kallio et al. 1990; Lancaster,
McCallion and Shaw 1984 and 1986;
Lancaster and Shaw 1989). In earlier works,
the following compounds were reported as
present: hydrogen sulfide, n-propyl mercap-
tan, ethyl alcohol, n-propyl alcohol, iso-
propyl alcohol, methyl disulfide, methyl
n-propyl disulfide, n-propyl disulfide, methyl
184 Source Book of Flavors
trisulfide, methyl n-propyl trisulfide, n-
propyl trisulfide, acetaldehyde, propionalde-
hyde, n-butyraldehyde, acetone, methyl
ethyl ketone. More recent studies using
GLC/MS have identified: methyl-1-propyldi-
sulfide, 3,4-dimethylthiophene, cis-methyl-
1-propenyl disulfide, transmethyl-1-propenyl
disulfide, di-1-propyl disulfide, cis 1-propyl
propenyl disulfide, trans-1-propyl propenyl
disulfide, methyl-1-propyl trisulfide, and di-
1-propyl trisulfide. Since this work, numer-
ous additional compounds have been identi-
fied. The interested reader should go to
Maarse and Visscher (1989) for a more
detailed listing of flavor compounds.
Galletto and Bednarczyk (1975) have
determined the relative flavor contribution
of the various components, and concluded
that methyl propyl disulfide, methyl propyl
trisulfide and di-propyl trisulfide are primar-
ily responsible for the characteristic flavor of
onion together with three other components,
which were not unidentified.
Quality Assessment of Allium Extracts
Onion and garlic extracts, unlike spice
oleoresins that are extracted with organic
solvents, contain water whose residual level
may influence their use in end products and
also their stability on storage. Salzer (1975)
has examined the quality assessment of
allium extracts and recommends the deter-
mination of: (a) water content by azeotropic
distillation with xylol, (b) reducing and total
sugar content, (c) color value using a suit-
able comparator, and (d) aromatic com-
ponents assessed by a gas chromatographic
method using an internal standard and
determined as either dipropyl disulfide
(onion) or diallyl disulfide (garlic).
References: Alliaceous Flavors
Abraham, K.O., Shankaranarayana, M.L.,
Raghavan, B., and Natarajan, C.P. 1982.
Odorous compounds of asafetida. VII. Isola-
tion and identification. Ind. Food Pack. 36(5):
65-76.
Abraham, K.O., Shankaranarayana, M.L.,
Raghavan, B., and Natarajan, C.P. 1979.
Asafoetida. IV. Studies on volatile oil. Indian
Food Pack. 33(1):29-32.
Andres, C. 1981. Encapsulated concentrates re-
tain full-flavor-profile balance. Food Process.
42(12):57.
Argentina, Instituto Argentino de Racionalizac-
ion de Materiales. 1986. Essential oils. Onion
oil. Argentinian-Standard; IRAM-SAIPA.
Block, E. 1985. The chemistry of garlic and
onion. Sci. Amer. 252(3):114-119.
Boelens, M., de Valois, P.J., Wobben, H.J., and
van der Gen, A. 1971. Volatile flavor com-
pounds from onion. 1. Agric. Food Chern.
19:984-999.
Brodnitz, M.H. 1971. Flavor components of gar-
lic extract. 1. Agric. Food Chern. 19:273-275.
Brodnitz, M.H. and Pollock, C.L. 1970. Gas
chromatographic analysis of distilled onion
oil. Food Techno/. 24(1):78-80.
Carson, J.F. and Wong, F.F. 1961. The volatile
flavor components of onions. 1. Agric. Food
Chern. 9:140-143.
Carson, J. F. 1987. Chemistry and biological prop-
erties of onions and garlic. Food-Rev. Inter-
national 3(112):71-103.
Coley-Smith, J.R. 1986. A comparison of flavor
and odor compounds of onion, leek, garlic
and Allium fistulorum in relation to germina-
tion of sclerotia of Sclerotium cepivorum. Plant
Pathol. 35(3):370-376.
Collin, H.A. and Musker, D. 1988. Allium com-
pounds. (Phytochemicals in plant cell cul-
tures). Cell Cult. Somatic Cell Genet. 5:475
Fenwick, G.R. and Hanley, A.B. 1985a. The
genus Allium. I. CRC Crit. Rev. Food Sci.
Nutrit. 22(3):199-271.
Fenwick, G.R. and Hanley, A.B. 1985b. The
genus Allium. II. CRC Crit. Rev. Food Sci.
Nutr. 22(4):273-377.
Freeman, G.G. and Whenham, R.J. 1975. A
survey of volatile components of some Allium
species in terms of S-alk(en)yl-L-cysteine
sulphoxides present as flavour precursors. 1.
Sci. Food Agric. 26(12):1869-1886.
Galletta, W.G. and Bednarczyk, A.A. 1975.
Flavor contribution of individual volatile com-
ponents of the oil of onion. 1. Food Sci.
40:1165-1167.
Gunther, E. 1948-1952. The Essential Oils, Vol.
I-VI. D. New York: Van Nostrand Co.
Hanley, A.B. and Fenwick, G.R. 1985. Culti-
vated alliums. 1. Plant Foods 6(4):211-238.
Hashimoto, S., Miyazawa, M., and Kameoka,

H. 1983. Volatile flavor components of chive
(Allium schoenoprasum L.). J. Food Sci.
48(6):1858-1859.
Heath, H. 1983. The microbiology of onion prod-
ucts. Food Flavour. Ingred. Pack. Process.
5(1):22-27.
Kallio, H., Tuomola, M., Pessala, R., and Vilkki,
J. 1990. Headspace GC-analysis of volatile
sulfur and carbonyl compounds in chive and
onion. In Flavour Science and Technology,
eds. Y. Bessiere and A.F. Thomas, pp. 57-
60. New York: John Wiley & Sons.
Lancaster, J.E. and Shaw, M.L. 1989. Gamma-
glutamyl peptides in the biosynthesis of S-
alk(en)yl-L-cysteine sulphoxides in Allium.
Phytochem. 28(2):455-460.
Lancaster, J.E., McCallion, B.J., and Shaw,
M.L. 1984. The levels of S-alk(en)yl-1-cysteine
sulfoxides during the growth of the onion
(Akkuyn ceoa L.). J. Sci Food Agric. 35(4):
415.
Lancaster, J.E., McCallion, B.J., and Shaw,
M.L. 1986. The dynamics of the flavor precur-
sors, the s-alk(en)yl-1-cysteine sulphoxides,
during leaf blade and scale development in the
onion (Allium cepa). Physiol. Plant. 66(2):
293.
Lawrence, B.M. 1981. Progress in Essential Oils:
Asafoetida Oil. Perf. Flav. 6(1):37.
Lawrence, B.M. 1985. Progress in Essential Oils:
Asafoetida Oil. Perf. Flav. 10(1):43.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food: Qualitative and Quanti-
tative Data. TNO-CIVO Analytical Food Insti-
tute: Zeist.
Miething, H. 1988. HPLC analysis of the volatile
oil of garlic bulbs. Phytother. Res. 2(3):149.
Moreira-Hernandez, T., Villegas, M.l., and
Cabrera-Rabi, L. 1987. Browning and cooked
flavour of garlic during dehydration. Tecno-
logia-Quimica 8(1):31-36, 86.
Moreira-Hernandez, T. and Villegas, M.l. 1987.
Effect of water activity on stability of freeze-
dried garlic flakes. Tecnologia-Quimica 8(4):
32-38, 86.
Moreira-Hernandez, T., Villegas, M.l., and
Cabrera-Rabi, L. 1986. Effect of drying tem-
perature on the quality of dehydrated garlic.
Evaluation of odour and pungency. Tecno-
logia-Quimica 7(4):35-42, 86.
Naito, S., Yamaguchi, N., and Yokoo, Y. 1981.
Studies on natural antioxidant. II. Antioxida-
tive activities of vegetables of Allium species.
Natural Flavoring Materials 185
J. Japan. Soc. Food Sci. Techno/. 28(6):
291-296.
Raghavan, B., Abraham, K.O., Shankaran-
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Asafoetida. V. Asafoetida products and
flavour losses during cooking and frying.
Indian-Food-Packer 33(3):11-14.
Raghavan, B., Abraham, K.O., Shankaran-
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C.P. 1974. Asafoetida. II. Chemical composi-
tion and physiochemical properties. Flavour
Ind. 5:179-181.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. /. Int. Flavours Food
Additives 6:151-157; II. Ibid. 206-210; III.
Ibid. 253-258.
Sass-Kiss, A., Petro-Turza, M., Szarfoeldi-
Szalma, 1., Pino, J., and Rosado, A. 1989.
Investigation of the volatile oil of Mako
onions. Nahrung 33(5):413-421.
Schreyen, L., Dirinck, P., Van Wassenhove, F.,
and Schamp, N. 1976. Volatile flavor com-
ponents of leek oil. J. Agric. Food Chern.
24(2):336-341.
Schreyen, L., Dirinck, P., Van Wassenhove, F.,
and Schamp, N. 1976. Analysis of leek vola-
tiles by headspace condensation. J. Agric.
Food Sci. 24:1147
Shankaranarayana, M.L., Raghavan, B.,
Abraham K.O., and Natarajan, C.P. 1973.
Volatile sulphur compounds in food flavours.
CRC Crit. Rev. Food Techno/. 4(3):395-435.
Teleky-Vamossy, G. and Petro-Turza, M. 1986.
Evaluation of odour intensity versus concen-
tration of natural garlic oil and some of its
individual aroma compounds. Nahrung 30(8):
775-782.
Vaughn, R.H. 1970. Incidence of various groups
of bacteria in dehydrated onions and garlic.
Food Techno/. 24(2):83-85.
Whitaker, J.R. 1976. Development of flavor,
odor and pungency in onion and garlic. Adv.
Food Res. 73-133.
Whitfield, R. and Last, M. 1991. Volatile Com-
pounds in Foods and Beverages. New York:
Marcel Dekker.
Yu, T.H., Wu, C.M., Liou, Y.C., and Chen,
S. Y. 1988. Flavor retention of garlic powders.
Food-Sci.-China 15(3):296-303.
186 Source Book of Flavors
BITTERING AGENTS
Although the taste sensation of bitterness is
generally disliked and in most foods is con-
sidered undesirable, there are several prod-
ucts in which the bitter attribute is both
characteristic and desirable (e.g., beer, cer-
tain alcoholic beverages such as vermouth
and aperitifs, tonic water and other "mixer"
products, etc.) and others in which some
element of bitterness is necessary to achieve
a desirable flavor balance (e.g., seasonings).
Bitterness is, of course, only one aspect of
the total profile and the use of the term
"bitters" in a generic sense as applied to
flavoring essences has a different connota-
tion from the description "bitter" applied as
a flavor attribute to other types of products.
Many classes of chemical compounds have
an inherent bitter character (Belitz and
Wieser 1985). Among the most intense of
these are the alkaloids, which are nitro-
genous bases that occur in many families of
plants. They are usually present as salts
associated with acetic, oxalic, lactic, malic,
tartaric, citric, or of special acids charac-
teristic of certain species of plants. Many of
the alkaloids have powerful physiological
actions, many being toxic (e.g., strychnine),
others pungent (e.g., piperine), stimulant
(e.g., caffeine) or analgesic (e.g., mor-
phine), etc.
For centuries, plant materials have been
used as a source of alcoholic extracts for the
formulation of bittering essences and the
compounding of herb blends to give distinc-
tive profiles for aperitifs and liqueurs; it is
an art stretching far back into history, but
still retained in many well-known products
made traditionally. Bitter products have
been used medicinally for generations as is
well attested by many old "herbals." Bitters
are generally distinguished according to the
level of their aromatic constituents. Where
these predominate the products are classed
as "aromatic bitters"; where the aroma is
relatively low they are called "strong bit-
ters." Most of the established bittering com-
positions would be regarded as well balanced
between these two extremes. Most bitter
liqueurs consist of the appropriate flavoring
essence in a base comprising alcohol, sugar
and water. The ratio of these ingredients
differs, but the alcohol content of the fin-
ished product generally lies between 23 and
32 percent by volume and the sugar between
6 and 20 percent, but mostly about 10 per-
cent. Many liqueurs, although originating
very long ago, are still proprietary products
whose composition is still strictly guarded,
with the designation registered and pro-
tected. Examples of bitters are quoted in
Pharmaceutical Formulas, Vol. 2, 12th Edi-
tion (1953), Chemist and Druggist, 28 Essex
St., London, WC 2, England. The principal
sources of bitter flavorings are listed in Table
7-4. The products used are generally alco-
holic percolations of finely ground plant
materials, which may be blended before
extraction and modified by the addition of
essential oils.
References: Bitters
Belitz, H.-D. and Wieser, H. 1985. Bitter com-
pounds: Occurrence and structure-activity re-
lationships. Food Rev. Inter. 1(2):271-354.
COCOA AND CHOCOLATE
The consumption of confectionery products
has increased continuously in the U.S.
despite the general trend of calorie con-
sciousness. The annual consumption of con-
fectionery products has increased from
16.1lb/person in 1980 to 20.5lb/person in
1990. Of the confectionery products sold
($9,081,592), chocolate-based products ac-
count for the major share ($6,240,284). In
addition to the chocolate sold as confec-
tionery products, a significant amount of
chocolate is consumed as other products
(e.g., chocolate coatings, cocoa, chocolate
chips and syrups). This market amounted to
about $1,409,908 in 1990.
The principal raw material used in making
cocoa powder and chocolate is the cacao
 Natural Flavoring Materials 187

TABLE 7-4. Natural bittering agents

Volatile Oil
Plant Source Botanical Classification Part Used Content Principal Constituents
(%)
Aloe Aloe chinensis, A. vera or Conc.leaf trace Aloin, emodin, trioxymethyl
A.perryi juice anthraquinone, gallic acid
Angelica Angelica archangelica or Root, seed 0.3-1 Cyclopentadecanolide, diacetyl,
A. atropurpurea furfural, angelic acid
Angostura Cusparia febrifuga Bark Cusparine, cusparidine, galipin,
galipoidine
Anise Pimpinella anisum or Fruit 1.5-6 Anethol, methyl chavicol
Illicium verum (China
star anise)
Artichoke Cynara scolymos or Leaves
C. cardunculus
Balm Oemon balm) Melissa officina/is Flowering herb 0.02-0.1 Geraniol, linalool, citronellol,
ci tronellal, ci tral
Buckbean Menyanthes trifoliata Leaves
Burdock Arctium lappa Herb, root and 0.15-0.3
seed
Calamus (sweet Acarus calamus Rhizome 0.8-3.5 Eugenol, methyleugenol
flag)
Calisaya Cinchona calisaya Bark
Calumba (columba) Jateorrhiza palmata Root about0.005 Columbin
Camomile, German Matricaria chamomilla Flower 0.3-1 Chamazulene, apigenine,
umbelliferone methyl ether,
caprinic acid
Camomile, Roman Anthemis nobilis Flower 0.3-1 n-Butyl isobutyrate, n-butyl
and isoamyl esters of angelic
and metacrylic acids
Caroba Jacaranda lancifoliata Leaves
Cascariila Croton elutaria Bark 1.5-3 Cascarillin, vanillin,
cascarillic acid
Centaury, minor Centaurium umbellatum Flowering herb Gentiopicrin, erythrocentaurin
(Erythraea centaurium) Oleanolic acid
Chicory Cichorium intybus Root
Chiretta Swertia chirata Entire plant Chiratin, ophelic acid
Cinchona Cinchona succirubra Bark Quinine, quinidine, cinchonidine
and other spp cinchonine, tannins
Colocynth Citrullus colocynthis Dried pulp Colocynthin, resins
Cubeb Piper cubeba Unripe fruit 8-18 Cube bin, piperine, cubebic
acid
Dandelion Taraxacum officinale Root Taraxacin, asparagin, resins
Dittany Dictamnus a/bus Root, bark
Dittany of Crete Origanum dictamnus Flowering herb
Elder Sambucus nigra Flower, bark about0.05
Elecampane lnula helenium Root Inulin, helenin
Fennel Foeniculum vulgare Fruit 4-6 Anethole, fenchone, methyl
chavicol, anisic acid
Galangal Alpinia officinarum Root 0.5-1 Methyl cinnamate, cineol,
camphor
Gentian Gentiana lutea Root trace Gentiopicrin, gentianic acid
Germander Teucrium chamaedrys Flowering
herb
Germander, golden Teucrium polium Herb
Holy thistle Carbenia benedicta Herb
Hop Humulus lupulus Flower 0.5-0.9 Lupulin (containing humulone,
lupulone, isohumulone,
isolupulone, lactaric acid,
cerotic acid
Horehound Marrubium vulgare Herb
Hyssop Hyssop us officinalis Flowering 0.3-0.9 Hyssopin
herb
Imperato ria Peucedanum osthruthium Rhizome
Juniper Juniperus communis Fruit 0.5-2.5 Terpenes
Kola Cola vera Seed Caffeine, kolanin
Licorice Glycyrrhiza glabra Root Glycyrrhizin, asparagin,
malic acid
 188 Source Book of Flavors

TABLE 7-4. Continued

Volatile Oil
Plant Source Botanical Classification Part Used Content Principal Constituents
(%)
Lovage Levisticum officinale Root 0.3-1
Mace Myristica fragrans Arillode 10-13
Myrrh Commiphora malmo[ and Oleo-gum- 3-8
other spp resin
Nutmeg Myristica fragrans Seed 6.5-8
Orange, bitter Citrus aurantium, var. amara Peel Limonin
Pellitory Anacyclus pyrethrum Root
Pickly ash Xanthoxyum americanum Berry, bark
Quassia Picaena excelsa Wood Quassin, neoquassin,
picrasmin
Rhubarb Rheum palma tum ana other Root Rhaponticin
spp
Sarsaparilla Smilax aristolochiaefolia Root Sarsaponin, parillin,
and other spp smilagenin
Sassafras Sassafras albidum and Root 6-9 Note: in U.S.A. and other
other spp countries, Sassafras must be
free of saffrole for use in food.
Simarubra Simarubra officina/is Root, bark
Squaw vine Mitchella repens Herb
Tansy Tanacetum vulgare Flowering herb 0.1-0.3 Thujone, camphor, borneol
Thyme Thymus vulgaris Herb 0.3-2.6 Thymol
Valerian Valeriana officinal is, Root 0.5-1 1-Bornyl isovalerate
V. wallichii
Virginia snake Aristolochia serpentaria Root 1-2
root
Wormwood Artemisia absinthium Flowering herb about0.5 Absinthin
Yarrow Achillea millefolium Flowering herb about0.25
Zedoary Curcuma zedoaria Root, bark 0.1-0.3

bean. Cacao beans are the seeds of TABLE 7-5. Major sources of cacao bean
Theobroma cacao L., a tree that grows in
(%)
most countries within the tropical belt where
temperatures range between 25° and 30°C, West Africa (Ghana, Ivory Coast,
there is high humidity (90-100 percent) and Nigeria, Cameroon) 68
adequate ground water. The pods holding South America (Brazil, Colombia,
Venezuela) 18
the beans develop in clusters on the trunk West Indies (Dominican Republic,
and main branches of the tree. In size and Trinidad) 2.5
shape, cacao beans resemble shelled Mexico 2
almonds; there are 25-50 beans in each New Guinea 2
Others (including Sri Lanka, Java, 7.5
pod. Commercially, cacao beans are desig-
Haiti, Kenya, Costa Rica)
nated according to their country of origin or
the port of export. Table 7-5 lists the major
sources of production.
The individual sources and commercial growing variety originating in Venezuela and
names of cacao beans are given in Table 7-6 now widely distributed because it is more
and domestic imports of cocoa beans in 1990 disease-resistant. The Crillo are large beans
are presented in Table 7-7. There are two having a sweet taste and little bitterness,
main varieties of cacao: Crillo, which has while the Forestero have purple kernels and
been cultivated in South America for cen- a marked bitterness. In commerce, the fol-
turies, and Forestero, derived from the wild- lowing terms are used: cacao, when refer-
 Natural Flavoring Materials 189

TABLE 7-6. Sources and types of cacao beans tree. In the Amazon and the Rio de la Plata
Commercial Type of
water area of Brazil grow over a hundred
Source Designation Bean million trees. Among the varieties of cacao
Brazil Bahia Forestero are the Bahia beans, which are of outstand-
Cameroon Douala Forestero ing quality; then Para cacao beans, which
Congo Vandeloo Forestero
Dominican Sanchez Forestero have a very mild chocolate flavor. Ecuador
Republic beans produce the finest cocoa. The beans
Ecuador Arriba Forestero
Guayaguil Forestero have a unique aroma and a characteristic
Machala Forestero chocolate flavor that is difficult to obtain
Ghana Accra Forestero
Nigeria Lagos Forestero from other beans.
Phillipines Maripipi Forestero The cacao varieties are known as Arriba,
Trinidad Port of Spain Forestero
Venezuela Caracas Crillo Machala, or Calao Guayaquil cacao. The
Maracaibo Crillo Arriba beans have a greater value than the
Porto Cabello Crillo
Machala beans. Machala cacao beans are
smaller and have a more bitter taste than
Arriba beans.
Venezuela also grows some of the finest
ring to the tree and its natural products; cacao. Its varieties are known as Caracas,
cocoa, to describe the manufactured prod- Carupano and Puerto Cabello. Caracas
uct used to make a beverage or as a pow- beans are large and the taste is of a strong
dered flavoring; chocolate, to describe the chocolate flavor. Carupano beans have a
manufactured product in a solid form. harsher chocolate flavor, but otherwise are
similar to Caracas beans. Puerto Cabello
beans have a reddish-brown color and sweet
Cacao chocolate flavor. Costa Rica beans have a
mild flavor and a characteristic aftertaste.
The finest cacao beans are grown in South Trinidad has the most important cacao pro-
America, which is the home of the cacao duction in the West Indies. The beans have

TABLE 7-7. Major sources of cocoa beans and volume imported into the U.S.
during 1990 (Source: United States Department of Agriculture
Foreign Agriculture Service)

Origin/countries Quantity (metric tons) Value

Honduras 1,793 1,952,732

Dominican Republic 43,742 40,604,742
Trinidad and Tobago 1,626 4,283,160
Colombia 1,350 1,840,850
Ecuador 38,868 45,902,597
Brazil 47,327 49,721,485
Malaysia 21,011 19,508,745
Singapore 1,700 1,473,132
Indonesia 35,000 32,602,822
Korea, Republic of 1,200 1,020,000
Papua New Guinea 10,850 10,445,338
Ivory Coast 85,763 102,754,389
Ghana 28,309 36,873,991
Nigeria 16,024 14,776,111
Total World 337,195 $367,041,858
190 Source Book of Flavors

a very good flavor. Grenada produces some roasting play an important part in flavor
very good cacao. Jamaica beans have an development. Chemical decomposition pro-
aromatic flavor. However, the taste is rather duces new and aromatic substances, which
bitter and harsh. Haiti beans are small with are important components of the complete
little flavor. San Domingo or Samana cacao chocolate flavor. Dehydration, oxidation
has a bitter flavor. Cuban cacao is of good and solubility changes take place in the
quality. Mexican beans are large and the tannins and bitter astringent substances. Un-
flavor of the nibs is mild. African cacao pleasant volatile materials, including hydro-
beans from the Gold Coast of Africa are carbons, ketones, volatile acids (butyric,
called Accra beans, after the name of the acetic), pungent organic bases and amine
port from which they are exported. Accra products of protein, are driven off. Any
beans form the basis for many chocolates, lipase present that would cause fat instability
especially the cheaper types. Nigeria is an- is destroyed. Water, of course, is lost and
other cacao-producing country. The Nigerian starch dextrinized, the latter contributing to
beans resemble Accra beans in appearance the definite increase in water-soluble matter
and flavor. The Cameroons grow cacao after roasting. The bean loses any last trace
beans that are small with kernels of bitter of gumminess, becomes dry and brittle,
taste. Other African cacao is grown in Sierra and of such a nature that it can be easily
Leone, Kenya, Tanzania and Uganda. Sri ground. Probably the most subtle and least
Lankan cacao beans are round and light- understood chemical changes take place
colored with a delicate taste and aroma. during the conching operation. This action,
Java, like Sri Lanka, produces cacao beans although mild, is prolonged and serves to
of the highest quality. remove the last traces of harsh flavor and
unpleasant volatile acids as well as some
Cocoa Production other organic substances. Final oxidation of
The ripe cacao pod weighs about a pound astringent tannin substances takes place.
and is filled with a pale pink, soft, sweet Moisture content is further reduced and
pulp, in which the beans are embedded. The fluidity increased. At somewhat elevated
beans are very bitter due to the presence of temperatures, a definite but very mild
tannins. They are altered by fermentation, caramelization may be achieved, producing
which makes the finished product palatable. distinctive flavor effects. Thus, conching
During fermentation, changes occur in the brings about the final chemical changes in
beans. The color changes to brownish red the chocolate. Commercial cacao beans
and the bitter taste almost disappears. consist of an outer shell and an inner kernel,
After fermentation, the beans still con- called the nib, which is surrounded by a thin
tain about 33 percent moisture and this must skin. The average cacao bean is composed
be reduced, desirably to 6-8 percent mois- of more than 54 percent cocoa butter, cocoa
ture by drying, to obtain a product that can matter and cocoa shell.
be stored. During the drying process, air
continues to penetrate the bean and enzy- Cocoa Powder and Cocoa Butter
matic oxidation is completed, resulting in a In the milling process, the nibs are finely
further reduction in the astringency and a ground and the butter is released from the
formation of the precursors that later, dur- cells, the effect being the production of a
ing roasting, give rise to the typical chocolate free-flowing liquor of rich dark color and
flavor and aroma. The process of roasting heavy aroma. In this form, it is known to the
and preparation for chocolate production manufacturer as "chocolate liquor," and is
is fully described by Minnifie (1989), Hui the basic material from which the manufac-
(1991) and Beckett (1988). turer produces other chocolate products.
Chemical changes that take place during Some of it is cooled and solidified into cakes,

which are sold to the consumer as "baking
chocolate."
To manufacture cocoa powder and cocoa
butter, the heated chocolate liquor is placed
in hydraulic presses, where it is subjected to
a pressure of approximately 6,000 lb per sq
in. This pressure forces some of the cocoa
butter through a retaining medium that holds
back the solid mass. The cocoa butter is
filtered and used by the manufacturer in
several ways. It is used in making "sweet
chocolate" and "milk chocolate," or it may
be made into various forms and be sold
for confectionery, pharmaceutical or other
sundry uses.
Cocoa butter has certain unique prop-
erties, such as being one of the most stable
edible fats, having a pleasant flavor and
aroma, and combining well with other con-
fectionery ingredients. Furthermore, it is
solid and easy to handle at ordinary room
temperature, yet it liquifies at body
temperature.
Constituents of Cocoa
After removal of cocoa butter from the cacao
nib, a brown mass of cocoa matter remains,
which contains purine, theobromine and
caffeine, enzymes, carbohydrates, and tan-
nins. Theobromine gives cocoa stimulating
properties like caffeine does for coffee. The
most important constituents, however, are
the tannins. They determine the color and
contribute substantially to the taste of cocoa.
Other constituents of cocoa matter are
starch, up to 0.50 percent sugar, and min-
erals. The sugar fraction consists largely of
glucose and fructose. The ash of cocoa mat-
ter contains mineral salts, including potas-
sium phosphate.
Cocoa shell comprises about 12.5 percent
of the bean and contains theobromine, color-
ing matter, mineral constituents and other
substances.
Breakfast and Dutch Processed Cocoa
The mass that is left in the hydraulic press
after the cocoa butter has been removed is
in the form of large hard cakes. It is reduced
Natural Flavoring Materials 191
to its final usable form by pulverizing it into
a very fine powder. It is then packed into
containers and sold to the consumer as
"breakfast cocoa," and also to confectioners,
bakers, ice cream manufacturers and others.
"Dutch processed cocoa" is made by
treating the beans, nibs, or chocolate liquor
with an alkaline solution, such as sodium
bicarbonate, to bring out color and accom-
plish flavor modifications. The amount of
alkali that can be used is specified and con-
trolled by the U.S. Government. Other than
the use of alkali, Dutch processed cocoa
is made similarly to American processed
cocoa.
Types of Cocoa
Semi-cocoa, which contains 32 to 45 per-
cent fat and possesses a chocolate-like flavor.
High-quality cocoa, which contains from
25 to 35 percent fat and is used in ice creams,
beverages, icings and chocolate syrups.
Breakfast cocoa, which contains not less
than 22 percent fat. It is used in chocolate
biscuits and crackers, cakes and fudge.
Semi-dry cocoa, which generally contains
from 15 to 18 percent fat and is used for
cocoa-milk drinks, chocolate-flavored des-
serts, chocolate pies and chocolate-flavored
syrups.
Dry cocoa, which contains from 10 to
12 percent fat. It is generally used in the
preparation of chocolate milk beverages.
Very dry cocoa, which contains from 6.5
to 7. 75 percent fat and is used for imitation
chocolate coatings by incorporating sugar
and a vegetable oil, usually coconut oil. It is
also used as dusting powder in confectionery.
Defatted cocoa, which contains from 0.5
to 3.0 percent fat and is used as dusting
powder and in the preparation of imitation
chocolates.
pH Values of Cocoa
Cocoa is quite hygroscopic due largely to
the fact that during the roasting process a
major portion of the starch present in the
raw nibs is converted into dextrins under the
influence of heat. These dextrins show a
192 Source Book of Flavors

great affinity for moisture when incorporated TABLE 7-8. Composition of chocolate liquor
into a batter that must be compensated for
(%)
by a reduction in flour.
Cocoa products may vary in pH from 5.2 Moisture 1.70
to as high as 8.8 for heavily Dutched cocoa. Fat 54.00
The pH of natural cocoa products, which Theobromine 1.08
Caffeine 0.42
include chocolate liquor and cocoa powder, Other nitrogen substances 0.42
is generally within the range of 5.2 to 6.0. Pure starch (by diastase) 8.21
This variation in pH is attributable to the Crude fiber 2.65
variable amounts of different organic acids Other carbohydrates 17.32
and other acid-reacting substances that are Total ash 3.04
Water-soluble ash 0.72
present. The pH of Dutched cocoas is in- Water-insoluble ash 2.32
fluenced by the type and amount of alkali Acid-insoluble ash O.Q2
used, the normal range being from 6.0 to
8.8. Natural cocoas, being acid in character,
require the use of baking soda. The acidity formula for the sake of economy, care must
of the cocoa liberates carbon dioxide gas be used to prevent a corresponding decrease
from the sodium bicarbonate and thereby in the quality of the product. To maintain
aids in aerating the batter. At the same time the same desirable texture and keep quality
the acidity is neutralized with an improve- in the fudge, an allowance should be made
ment of the cocoa color. An increase in the for the difference in fat content of the cocoa
alkalinity causes a deterioration of flavor at and chocolate liquor. Approximately 58lb
a pH above 8.0. of cocoa and 42lb of some added fat can be
used in place of 100 lb of chocolate liquor.
However, the same fine flavor will not be
Chocolate Liquor
obtained by use of the cocoa and, further-
Chocolate liquor is made directly from the more, if some fat other than cocoa butter is
cocoa bean by grinding the roasted bean. It used, caution should be observed so that the
contains a high level of cocoa butter and shelf life of the fudge is not shortened, due
thus is a much "richer" product than cocoa to the greater tendency towards rancidity
(Table 7-8). of these fats as compared to cocoa butter.
Occasionally, some Dutch process cocoa
may be used to obtain a certain minimum
Chocolate Fudge color and flavor at the lowest cost. In
A good chocolate fudge should have a dis- general, the color and flavor of these pro-
tinct, fine chocolate flavor, good texture, a ducts will not compare with those where a
pleasing appearance and long shelf life. An higher percentage of a milder cocoa is used.
average chocolate fudge will contain about Where cocoa is used, it is usually cooked in
5 percent nonfat cocoa material on a dry with sugar, glucose and other ingredients.
basis. This corresponds to 6 percent or Chocolate liquor either can be handled this
11 percent chocolate liquor. Some fudges way, or, at least with smaller batches, added
contain approximately 20 percent fat. after the batch has cooked and before
Either cocoa or chocolate liquor may be it cools. This cooking of the cocoa may
used. The cocoa may be high, medium, or destroy some of the flavor due to the cocoa's
low fat, and may be either American or tendency to burn. This may be another
Dutch process. So far as flavor is concerned, reason why fudges made from liquor have a
the finest result will be obtained by the use finer flavor. If the chocolate liquor is used, it
of a good-quality chocolate liquor. If cocoa is added after the batch has cooled.
is substituted for chocolate liquor in a There are other uses for cocoa powder,

including such items as chocolate-flavored
syrups, chocolate-flavored puddings, flavor-
ing for tobacco, pharmaceutical prepara-
tions, instant cocoa coatings of the summer
type, and as an ingredient in numerous
household recipes.
Chocolate
The most popular chocolate product in the
U.S. is the milk chocolate bar. Chocolate
liquor, pure fluid whole milk and powdered
sugar are the basic ingredients for this item.
After these ingredients have been mixed,
the mixture is then passed through a series
of large steel roll refiners, where an intense
shearing and rubbing action reduces the
mass to a uniform paste that is so smooth
that the coarsest particles will be less than
50 J.l in size. This smoothness is one of
the necessary characteristics that makes
chocolate a delight to the palate, but this is
not enough. To further improve the pro-
duct, it is then processed for about 72 hr in
machines called "conches," in which the
chocolate is pushed back and forth by a
mechanical device (e.g., steel roller). By
this action, any rough edges on the fine
chocolate particles are smoothed off,
desirable flavor is further developed and
the entire mass is blended together most
intimately. It is in the conches that the
delicate flavor effects we have come to
expect from fine chocolate are developed.
After conching, the viscosity of the
chocolate is adjusted to the point where it is
most easily handled, and it is then cooled
and cast into bars, blocks and other forms.
Almonds, peanuts, or other ingredients can
be added before casting, if desired. "Sweet
chocolate" and "semisweet chocolate" are
processed similarly to milk chocolate except
that no milk is used. A good deal of sweet
and semisweet chocolate is sold to con-
fectioners for making chocolate-covered
candies. Increasingly large amounts of
semisweet chocolate are being used by the
consumer to make cookies, candy, cakes
and other items.
Natural Flavoring Materials 193
Flavor Constituents
Flavor aspects of cocoa and chocolate are
discussed in several sources, including the
texts noted earlier by Minifie (1989) and
Beckett (1988), as well as by Wood and Lass
(1985) and Flament (1989). The best source
for a listing of flavor compounds (and a
bibliography of research on flavor) found in
cocoa is Maarse and Visscher (1989).
Cocoa Powder Extenders and Replacers
Cacao beans are a major trading commodity
and prices are inevitably subject to wide
market variability. During 1977, the world
price of cacao beans rose to record heights,
reaching approximately three times the
price prevailing three years earlier. The
following comparisons of average price per
pound on the New York market may be of
interest: 1971, 26.8 ¢; 1972, 32.2 ¢; 1973,
64.4¢; 1974, 98.1¢; 1975, 74.8¢; 1976,
$1.09; and 1977, $2.15. At these prices,
users of cocoa powder reexamined formula-
tions and attempted to hold to ingredient
costs. The flavor industry responded to
market needs by developing replacers for
cocoa powder and cocoa butter.
Cocoa replacers took various forms,
including imitation and reaction flavors as
well as the use of related natural products,
e.g., carob and malted barley/roasted malt
blends. The difficulty of creating an exact
match for cocoa powder or cocoa butter is
the achievement of the correct balance
of color, textural properties and flavor.
While imitation flavors can reproduce the
aroma components of cocoa, they generally
lack the roundness, fullness and textural
properties of cocoa. Reaction flavors have
proven to be more effective than imitation
flavors since they can be formulated and
processed to more completely simulate the
complexity of a true cocoa. Additionally,
reaction flavors can be labeled in the U.S.
as being "natural," which is an important
consideration in the marketplace. Reaction
flavors can be relatively simple as is demon-
strated in the flavor outlined in Table 7-9.
194 Source Book of Flavors
TABLE 7-9. Chocolate reaction flavor
Leucine 0.5g
Tyrosine 1.5g
Serine 1.5g
Valine l.Og
Tannic acid (Quercus Spp.) l.Og
Vanilla extract (2X) 3.0ml
Fructose 5.0g
Propylene glycol 105.0ml
The above ingredients are mixed in a
round-bottomed flask, which is then fitted
with a water-cooled condenser. The solu-
tion is heated at l20°C in an oil bath, with
sufficient stirring for 30 min. Cool the solu-
tion and evaluate the sensory character at a
1 percent level both in water and sugar
water.
The texture of cocoa powder is best
reproduced by carob, the fruit of the carob
or locust tree, Ceratonia siliqua L., which
grows in most Mediterranean countries and
has been used as a food for centuries. In the
Bible, it is called Locust and from its use
acquired the name St. John's Bread. The
trees bear long flat dark-brown pods, which
are harvested and dried, the seeds removed
and the deseeded pieces roasted, milled and
blended. Carob powder looks like and has
the texture of cocoa powder, with a sweetly
aromatic, slightly malt-like flavor. It con-
tains 45-50 percent of natural sugars, 0.5-2
percent fat but only 4-6 percent of protein.
It does not contain any theobromine or
caffeine, whereas cocoa powder contains
about 2 percent and 0.15 percent, respec-
tively, of these alkaloids. Carob bean is
classified as GRAS. A carob bean extract,
which is a semifluid product, is available for
use where this form is more applicable.
Flavorings based on carob powder found
some acceptance as partial or total replace-
ments for cocoa powder in a wide spectrum
of end products. However, as the price
of cocoa declined in the following years,
the use of carob as a cocoa replacer also
declined. Carob is not cocoa and thus
proved to be an inadequate substitute for it.
The major use of carob today is as a flavor-
ing material in itself or as a cocoa substitute
for those who for some reason do not want
to consume cocoa (e.g., avoid theobromine).
Blends of spray-dried malted barley
and roasted malt extracts have also been
suggested as the basis for a limited replace-
ment of cocoa powder (35-50 percent).
They typically were used with natural or
artificial chocolate flavorings. An added
advantage is claimed, as malt is a natural
flavor enhancer.
References: Cocoa and Chocolate
Baigrie, B.D. and Rumbelow, S.J. 1987.
Investigation of flavour defects in Asian cocoa
liquors. J. Sci. Food Agric. 39(4):357-368.
Beckett, S.T. 1988. Industrial Chocolate Manu-
facture and Use. New York: A VI.
Bertram, H.T. 1979. Chocolate, cocoa and their
substitutes. Snack Food Oct., 26-27:51.
Blenford, D.E. 1983. St. John's bread = carob.
Food Flavour. Ingred. Pack. Process. 5(10):
23-25.
Carlin, J.T., Lee, K.N., Hsieh, O.A.L., and
Hwang, L.S., and Ho, C.-T. 1986. Com-
parison of acidic and basic volatile compounds
of cocoa butters from roasted and unroasted
cocoa beans. J. Am. Oil Chern. Soc. 63(8):
1031.
Chaveron, H., Guyot, B., Hashim, L., Pezoa,
H., and Pontillon, J. 1989. Formation
and evolution of mathylpyrazines during
cocoa roasting. Developments in Food
Science. Flavors and Off-Flavors '89, ed.
G. Charalambous, pp. 305-319. Amsterdam:
Elsevier.
Dimick, P.S. and Hoskin, J.M. 1981. Chemico-
physical aspects of chocolate processing-a
review. Can. /nst. Food Sci. Techno/. J.
14(4):269.
Flament, I. 1989. Coffee, cocoa, and tea. Food
Rev. Internat. 5(3):317-414.
Gill, M.S., Macleod, A.J., and Moreau, M.C.
1985. Aroma components of cocoa beans.
Dev. Food Sci. 10:261.
Hui, Y.H. 1991. Encyclopedia of Food Science
and Technology. New York: John Wiley &
Sons.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food. pp. 950-952.
Netherlands: Grafische Industrie Kreon,
Zeist.
 Natural Flavoring Materials 195

TABLE 7-10. U.S. per capita consumption of specified beverages

1970 1980 1982 1984 1986 1988 1990

Item (Gallons)

Soft drinks" 22.7 34.2 35.6 38.8 42.1 46.0 47.5

Coffeeb 35.7 27.4 26.6 26.4 25.8 25.4 25.2
Beer 18.5 24.3 24.4 23.9 24.1 23.7 23.4
Milk 22.8 20.6 19.7 19.7 19.9 19.3 19.0
Teab 5.2 7.3 7.5 7.2 7.3 7.4 7.2
Bottled water 2.7 3.3 4.0 5.7 7.2 8.8
Juices 6.5 6.9 6.8 6.6 7.3 7.1 6.9
Powdered drinks 6.0 6.0 6.4 6.0 5.2 5.3
Wine" 1.3 2.1 2.2 2.3 2.4 2.2 2.0
Distilled spirits 1.8 2.0 1.9 1.9 1.7 1.6 1.4
a. Preliminary; b. Based on 3-year moving average; c. Includes wine coolers beginning 1984.
Source: Beverage Industry Magazine.

TABLE 7-11. Commercial sources of green coffee beans then a wine, a medicine and, finally, a
Country Percentage of Commercial beverage. In the beginning, the dried coffee
of origin World Supply Designation berries were crushed and mixed with fat to
Brazil :to Santos form food balls. Then a wine was made from
Paranas
Minas the raw beans and dried skins. The roasting
Colombia 25 Medillins of the beans began in the 13th century. The
Armenias
Manizales beverage was introduced from Arabia into
Africa 9 Turkey in 1554; Venice in 1615, France
Ethiopia Djimmas
Harrars in 1644, England and Vienna in 1650, and
Congo Oicru North America in 1668.
Angola Ambriz
Mexico 6 Coatepecs Coffee has become a major beverage in
Oaxacas many parts of the world. While coffee con-
Tapachulas
Honduras 4 Co pans sumption was the highest on a per capita
Guatemala 4 Antiguas basis among beverages twenty years ago, it
All other sources 12
(about 20 coun- still is number two, trailing soft drinks by a
tries) considerable margin (Table 7-10).

Minifie, B.W. 1989. Chocolate, Cocoa, and The Green Bean

Confectionery: Science and Technology; 3rd
Edition. New York: Van Nostrand Reinhold.
Ney, K.H. 1989. Cocoa off-flavours. Gordian.
89(9): 169.
Silwar, R. 1988. Gas chromatographic-mass
spectrometeric investigation of cocoa aroma.
Quantitative determination of steam volatile
aroma constiuents. Cafe Cocoa. 32(3):243.
Wood, G.A.R. and Lass, R.A. 1985. Cocoa.
London: Longman.
COFFEE
The word coffee comes from the Arabic
word "qahwah." Coffee was first a food,
Coffee is derived from a small evergreen
tree or shrub of which there are two main
species, Coffea arabica L. and C. robusta
L.; a third species, C. !iberica L., is of little
commercial importance. Coffee grows in
highlands in the tropics at 2,000 to 6,000ft
above sea level where the day temperature
is about 70°F and there is adequate ground
water. The crimson fruits contain two seeds,
the adjacent sides of which are flattened and
embedded in a pulpy mass. All the outer
material is discarded during preparation
for market, leaving the cleaned greenish-
196 Source Book of Flavors

TABLE 7-12. Green coffee: Total production in TABLE 7-13. Composite analysis of green coffee
selected countries• in thousands of Mgper
60Kg bagsb Component (%) 100gm
Water 8-12
Region and Country 1990/91 Oil (ether extract) 4-18
Unsaponifiable 0-2
North America: Nitrogen 1.8-2.5
Costa Rica 2,680 Protein 1 9-16
Caffeine 0-2
El Salvador 2,500 2-8
Chlorogenic acid
Guatemala 3,440 Trigonelline 1-3
Honduras 1,665 Ash: 2.5-4.5
Mexico 4,550 Calcium 85-100
To talc Phosphorus 130-165
17,730 3-10
Iron
South America: Sodium 4
Brazil 28,000 Manganese 1-45
Colombia 14,500 Rudidium traces
Copper traces
Equador 1,900 traces
Fluorine
Peru 1,300 Tannin 2
Venezuela 1,100 Caffetannic acid 8-9
To talc 47,555 Caffeic acid 1
Pentosans 5
Africa: Starch 5-23
Cote d'Ivoire 4,500 Dextrin 0.85
Ethiopia 3,000 Sucrose 5-10
Kenya 1,600 Reducing sugars 0-5
Cellulose 10-20
Madagascar 1,000 Hemicellulose 20
Uganda 3,000 Lignin 4
To talc 19,375 Vitamins (present in small amounts):
Asia and Oceania: Carotene, thiamin, riboflavin, folic
acid, niacin, pantothenic acid,
India 3,500 citrovorum factor, B-6, and B-12.
Indonesia 6,900 Choline: 60 mg per 100 gm.
Papua New Guinea 1,000
1,300
1 Amino acides from portein: alanine, aspartic acid, glu-
Philippines tamic acid, glycine, leucine, phenylalanine, serine, thre-
Thailand 1,000 onine, valine, cystine, methionine, and proline.
Vietnam 1,350
To talc 15,270
Grand Totalc 99,930 Composition of Green Coffee
The composition of green coffees changes as
a. Coffee marketing year begins about October in some
countries and April or July in others. the fruit develops on the trees, and later
b. One bag= 132.276 pounds.
as it is processed by different techniques
c. Total includes other countries not listed above.
(Table 7-13). Green coffee, if stored dry
Note: Production estimates for some countries include cross-
border movements. and away from disagreeable odors, will
retain its flavor potential for three years or
more. However, the color may be affected
yellowish seeds as the coffee beans of within a year, even in dry storage. The
commerce. moisture content must be kept below 10
The principal commercial sources and percent to prevent flavor deterioration and
commercial names of green coffee beans unpalatability.
are given in Table 7-11 and the countries
exporting to the U.S. market are listed in Coffee Roasting
Table 7-12. The exact differences between
coffee from various sources has never been Green coffee is devoid of aroma. A water
precisely determined. Analytical data that infusion is bitter and unpalatable. The
has been published do not provide adequate green beans must be heated under carefully
characterization in respect of origin. controlled conditions to bring about the

desired changes in chemical composition.
This process, called "roasting," is actually a
mild pyrolysis during which some of the
components are decomposed at rates in
accordance with their relative stabilities
toward the heat applied. During the pro-
cess, the green coffee, at first slowly, then
more rapidly, loses its greenness and takes
on the familiar brown color. The decrease in
greenness with increase in temperature has
been measured and can be used as a guide
for controlling the process. As the tempera-
ture approaches 400°F, the beans begin
to pop and expand to nearly twice their
original volume. By this time, much of the
flavor has been developed. Finishing the
roast now requires only a few minutes.
The roasting process is stopped abruptly
by a short water quench and rapid air cool-
ing at a precise temperature end point,
varying within a range of 390° to 450°F,
depending upon the knowledge the operator
has acquired from previous experience. He
knows that he must heat it to a specific
brown color, which is related to both rate of
heating and final temperature, in order to
develop those flavor characteristics most
acceptable to consumers. By this very artful
but indirect method, he is able to set up
controls on flavor formation.
The moisture content of the beans is
reduced to about 2 to 3 percent during roast-
ing. There is a total loss in weight of about
16 percent. This loss is made up of original
moisture and of volatile decomposition pro-
ducts. Seven or 8 percent of the dry green
coffee is decomposed and lost. The color
of the beans changes to brown, and their
volume increases from 50 to 100 percent.
The acidity of aqueous solutions increases to
a maximum and then decreases as roasting
progresses; lightly roasted coffees have the
highest acidity. The aromatic properties
change drastically.
From the proximate analyses it appears
that the protein and fat are very stable. The
greatest losses occur in the carbohydrate
and caffetannic groups. Much of the de-
crease in weight is due to decomposition of
Natural Flavoring Materials 197
sucrose and chlorogenic acid. A study of
nitrogen distribution in green and roasted
coffee hydrolysates shows that a slight
decrease in total nitrogen is accounted for
by relatively large decreases in the basic and
nonbasic fractions of aqueous extracts.
Amino acid analysis indicates that some
acids are much more stable than others and
that those in a fraction extractable with
water undergo considerable decomposition.
Tannins, including chlorogenic acid, are
partially decomposed in direct relation
to the degree of roast. Approximately 50
percent of both chlorogenic acid and true
tannin is lost in a heavy roast. While the
decomposition of trigonelline depends upon
the degree of roast, it is estimated that loss
is about 15 percent. Data relating to the
caffeine content of green and roasted coffee
indicate that this component is quite stable.
Losses that do occur are more likely related
to sublimation than decomposition.
The effect of roasting on coffee oil
is conflicting. Several studies report no
appreciable loss or change in components.
The values for the ether extract are almost
independent of variety; they differ after
roasting with variety and degree of roast. It
is generally conceded that phosphatides,
which are found in green beans in amounts
ranging toward 2Vz percent, are almost
completely destroyed.
Research has been much more concerned
with the volatile constituents in an effort
to discover the dominant factors in coffee
aroma.
Instant (Soluble) Coffee
The market for instant coffee in the US has
been gradually decreasing with time (Table
7-14). While its use is increasing in other
countries worldwide, currently it has less
than 20 percent of the US coffee market.
World production of instant coffee is on the
order of 400 million lb annually.
Instant or soluble coffee is prepared in a
battery of column extractors in which the
finely ground roasted beans are extracted
198 Source Book of Flavors
TABLE 7-14. United States: Coffee consumption by types, 1960-1991 (Cups per
person per day)
Year All coffee
1960 2.77
1970 2.57
1980 2.02
1990 1.73
1991 1.75
Source: ICO, United States of America Coffee Drinking Study- Winter 1990 and the National
Coffee Association's United States of America Coffee Drinking Study- Winter 1991.
countercurrently with water under pressure
at 175°C (350°F) for a period of about 4 hr.
This results in an almost complete recovery
of solubles. The initial concentrate is then
either spray-dried to give the familiar
free-flowing powder or freeze-dried and
agglomerated to give a product looking
more like ground coffee. In order to improve
the "fresh perked" coffee aroma of these
products, it is usual to incorporate about 0.2
percent of recovered coffee oil, either by
spraying onto the surface of the powder or
by incorporation into the concentrate prior
to freeze drying. The resulting products are
packed under an inert gas in order to retain
their distinctive aromatic properties. The
characteristics of these products and a fuller
treatment of their manufacture are given
by Nair and Sivetz (1973), Sivetz (1974),
Wrigley (1988) and Pieterse and Sihis
(1988).
Coffee Flavor
There has been substantial research on
the flavor of coffee. Excellent sources of
information include the annual internal
symposium on coffee (see reference list) as
well as reviews (Flament 1983; Tressl1989),
the tabluation of flavor compounds found
in coffee (Maarse and Visscher 1989) or
individual research publications, some of
which are noted in the reference portion of
this section.
Coffee Substitutes
In 1977, the world price of coffee beans rose
very sharply and gave rise to a demand for
Regular Soluble Decaffeinated
2.21 0.56 0.08
1.91 0.66 0.15
1.39 0.62 0.34
1.42 0.29 0.36
1.46 0.27 0.32
coffee substitutes. Numerous alternatives
were developed based on roasted cereals
(e.g., corn), soybeans or other edible plants
and seeds together with caramel color,
sugar and a small percentage of acidulant
(e.g., malic acid). Caffeine was incorporated
if desired and imitation coffee flavoring
was added to give a fuller coffee-flavored
product. While some of these substitutes
were capable of producing an acceptable
beverage, they never gained a significant
market share and have largely disappeared
from the market.
References: Coffee
Akieda, T. and Kato, T. 1987. Analysis of aroma
components in coffee flavour. Reports of the
Central Customs Laboratory f Kanzei Chua
Bunsekishohoj. No. 27:17-23.
Amorim, H.V., Josephson R.V., Hamonniere,
M., Ducruix, A., Pascard, Billy, C., Zuluaga,
Vasco, T., Poisson, J., Berndt, W., Meier,
Cabell, E., Bonilla, V.C., Quijana, R.-M.,
Kurz, G., Martinez, Villalba B., and Smith,
R.F. 1976. 7th International Colloquium on
the Chemistry of Coffee. Hamburg, 9-14June
1975. pp. 571. Paris, France; ASIC.
Anon. 1989. Extracting a natural coffee flavour.
Food Process. UK. 58(5):15.
Becker, R., Doehla, B., Nitz, S., Vitzthum,
O.G., Clifford, M.N., Kazi, T., Kellard, B.,
Birch, G.G., Maier, H.G., Stegen, G.H.D.
van der, Duijn, J. van, Cammenga, H.K.,
Steppuhn, M., Bothe, H., Bradbury, A.G.W.,
Halliday, D.J., Pictet, G.A., Brunner, G.,
and Gabel, P.W. 1987. Programme 12th
International conference on coffee science.
pp. 54. Paris, France; Association Scientifique
Internationale du Cafe.

Becker, R., Doehla, B., Nitz, S., and Vitzthum,
O.G. 1988. Identification of the "peasy" off-
flavor note in central African coffees. Colloq.
Sci. Int. Cafe.
Clifford, M.N., Ohiokpehai, 0., Menezes, H.
de, Cros, E., Fourny, G., Vincent, J.C.,
Kappeler, A.W., Baumann, T.W., Clarke,
R.J., Maier, H.G., Kazi, T., Tchana, E.,
Jacquet, M., Guyot, B., Macdonald, I.A.,
Macrae, R., Dentan, E., Illy, A., Gabel,
P.W., Hinrichsmeyer, K., Cammenga, H.K.,
Adomako, D., and Smith, R.F. 1986. 11th
International scientific colloquium on coffee.
Lome, 11-IS February I985. pp. 696.
Paris, France; Association Scientifique
Internationale du Cafe.
Dart, S.K. and Nursten, H.E. 1985. The changes
in the volatile components of instant coffee
with storage. Dev. Food Sci. 10:239-252.
Elmore, J.S. and Nursten, H.E. 1990. A com-
parison of the headspace extracts of instant
and ground coffee. Flavour Science and
Technology, eds. Y. Bessiere and A.F.
Thomas, pp. 203-208. West Sussex: John
Wiley & Sons.
Flament, I. 1989. Coffee, cocoa, and tea. Food
Rev. Internat. 5(3):317-414.
Flament, I. and Chevallier, C. 1988. Analysis of
volatile constituents of coffee aroma. Chern.
Ind. 18:592.
Flament, I. 1983. Coffee, cocoa and tea flavors:
a review of present knowledge. Colloq. Int.
Aromes Aliment. 82.
Fung, V.A., Cameron, T.P., Hughes, T.J.,
Kirby, P.E., and Dunkel, V.C. 1988.
Mutagenic activity of some coffee flavour
ingredients. Mutation Research, Genetic
Toxicology Testing. 204(2):219-228.
Gutmann, W., Werkhoff, P., Barthels, M., and
Vitzthum, O.G. 1979. Comparison of the
aromatic substances of Arabusta, Arabica,
and Robusta coffee beans by the "headspace
technique." 8th International Scientific
Colloquium on Coffee. pp. 153-161. Bremen,
Federal Republic of Germany; Hag AG.
Hahn, D., Oliveira, J.S., Vilar, H., Ferreira,
L.A.B., Fragoso, M.A.C., Aguiar, M.C.,
Cruz, M.J.R., Goncalves, M.M., Coste, R.,
Rostolan, J. de, Lopes, F., Santos, A. Cdos,
Matos, N., Martins, L., Teixeira, A.L.,
Mexia, J.T., Chassevent, F., Dalger, F.,
Graca, J.A.B. da, and Pereira, M.M. 1973.
5th International Colloquium on the Chemistry
Natural Flavoring Materials 199
of Green and Roasted Coffees and their
Derivatives, Lisbon, 14-19 June 1971.
pp. 435. Paris, France, Author.; Association
Scientifique Internationale du Cafe.
Ito, H., Atsuta, S., Shibata, K., Shimoda, M.,
and Osajima, Y. 1983. Studies on the aroma
of coffee. 3. Standard aromagram of roast and
ground coffee and changes during storage.
Nippon Shokuhin Kogyo Gakkaishi 30(3):
133.
Kulaba, G.W. 1981. Coffee processing research:
a review. Kenya Coffee. 46(549):351-360.
Liardon, R. and Spadone, J.C. 1985. Coffee
aroma investigation by combined capillary
GC headspace and multivariate statistics.
Colloq. Sci. Int. Cafe. 11:181.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food. pp. 950-952.
Netherlands: Grafische lndustrie Kreon,
Zeist.
McCamey, D.A., Thorpe, T.M., and McCarthy,
J.P. 1990. Coffee bitterness. Dev. Food Sci.
25:169.
Nair, J.H. and Sivetz, M. 1973. Coffee and Tea.
In Food Dehydration, Vol. 2. W.B. Van
Arsdel. Westport, Conn.: A VI Publishing Co.
Pieterse, M. and Silvis, H.J. 1988. The World
Coffee Market and the International Coffee
Agreement. Wageningen: Pudoc Pub.
Quijano, Rico M., Paoletti, R., Cantaluppi, S.,
Pfrunder, R., Wanner, H., Frischknecht,
P.M., Baumann, T.W., King, C.J., Adams,
M.R., Dougan, J., Zuluaga, Vasco, J.,
Tabacchi, R., Wilhelmsen, L., Tibblin, G.,
Elmfeldt, D., Svaerdsudd, K., Wedel, H.,
Heyden, S., Spindel, E., Arnold, M., Cusack,
B., Wurtman, R.J., Wurzner, H.P., Smith,
R.F., Clarke, R.J., Watson, A.G., and
Rolz, C. 1980. 9th International Scientific
Colloquium on Coffee. pp. 835. Paris, France;
ASIC.
Sivetz, M. 1974. Coffee. In Encyclopedia of Food
Technology, eds. A.H. Johnson and M.S.
Peterson. Westport, Conn.: AVI Publishing
Co.
Smith, R.F., Ribeiro, F.A., Xabregas, J.,
Gomes, V., Santos, A. Cdos, Nogueira, C.,
Concalves, A., Mexia, J.T., Vidal, V.A.C.,
Ferreira, L.A.B., Fragoso, M.A.C., Peralta,
M.F., Silva, M.C.C., Rebelo, M.C., Lopes,
M.H., Oliveira, E.F., Vilar, H., Aguiar,
M.C., Pereira, A. Jr., Pereira, M.M.,
Campos, L.S., Rodrigues, J.M.L., Horman,
200 Source Book of Flavors
I., and Viani, R. 1973. 5th International
Colloquium on the Chemistry of Green
and Roasted Coffees and their Derivatives,
Lisbon, 14-19 June 1971. pp. 435. Paris,
France, Author.; Association Scientifique
Internationale du Cafe.
Szente, L. and Szejtli, J. 1986. Molecular
encapsulation of natural and synthetic coffee
flavor with b-cyclodextrin. J. Food Sci. 51(4):
1024.
Tress!, R. 1989. Formation of flavor components
in roasted coffee. In Thermal generation of
aromas, eds. T.H. Parliment, R.J. McGorrin
and C.-T. Ho, pp. 285-301. ACS Symposium
Series. 409. Washington, D.C.: American
Chemical Society.
Tress!, R. and Silwar, R. 1981. Investigation
of sulfur-containing components in roasted
coffee. J. Agric. Food Chern. 29:1078-1082.
Vitzthum, O.G., Weisemann, C., Becker, R.,
and Hoehler, H.S. 1990. Identification of an
aroma key compound on robust coffees.
Cafe, Cocoa, The 34(1):27.
Wrigley, G. 1988. Coffee. New York: Wiley.
Yamanishi, T. 1981. Flavor Research. Tea,
coffee, cocoa and other beverages. Food Sci.
7:231.
ESSENTIAL OILS
A wide range of plant materials contain
essential or volatile oils-the two terms are
used synonymously. These oils are primarily
responsible for the characteristic aroma
of the plant material, are generally com-
plex mixtures of organic chemicals and
are insoluble in water. Essential oils may
be recovered by distillation, mechanical
expression, solvent extraction, enfluerage
and adsorption, depending on the nature
of the plant material, the quantity of oil
present and the relative stability of the
various components (Hui 1991). Many
essential oils are available commercially;
some of them have been discussed under the
headings "alliaceous flavors" and "herbs
and spices"; however, far more than these
are used in the formulation of flavorings,
seasonings, etc., and even more in the
compounding of fragrances.
Manufacturing Methods
The individual oils are described in stan-
dard texts such as Guenther (1948-1952),
Arctander (1960) and Fenaroli's Handbook
of Flavors (Furia and Bellanca 1975). The
processing techniques used in their prepara-
tion are discussed in the chapter of this text
on flavor manufacturing, but briefly include
the following:
Steam Distillation
Steam is passed through a bed of the plant
material (previously comminuted to an
appropriate particle size to allow for good
steam penetration), the volatilized essential
oils are carried over in the steam, are con-
densed and separate as an upper layer or
lower layer in the condensate, depending on
the specific gravity of the oil. The water
layer has a distinctive odor and may be
either reboiled in order to recover the en-
trained or soluble components or, in certain
instances, used directly as an aromatic
water.
Expression (or Pressing)
This technique is used for fruit peels rich in
oils, such as orange, lemon, lime and other
citrus fruits. The selected whole fruits
are first washed and then crushed between
rollers or automatically handled in specially
designed extractors, which recover both
juice and oil concurrently. The liberated oil
is washed with a spray of water and the oil
separated by means of a centrifuge. The
highest quality citrus oils are those that have
had least contact with water.
Solvent Extraction
This technique involves the treatment of
floral material that is too sensitive for normal
distillation techniques. The collected flowers
are placed in tiers on perforated plates in a
suitable extraction vessel and the selected
solvent allowed to percolate through until
the mass is exhausted. The solvent is

recovered by distillation under vacuum and
the residue contains the essential oil.
Enfleurage
Enfteurage is a long-establishe d method of
extraction of delicate floral aromas by solu-
tion and adsorption into fat. The odorous
fat is extracted with a solvent to recover the
essential oil and the residual fat may be used
in the making of scented soaps.
Adsorption Techniques
These techniques involve the passage of
heated air or inert gas over the aromatic
material and then through activated carbon.
The essential oil components are adsorbed
onto the charcoal and may be recovered by
solvent extraction.
Concrete
This is the semisolid mixture of essential oil
and fatty-waxy materials that remain after
the removal of solvent from the enfleurage
process.
Absolute
Obtained by the solution of a concrete in
alcohol, then chilling and filtering to remove
the waxes. The alcohol is removed by dis-
tillation to produce the absolute.
Isolate
A pure chemical substance separated from
natural products by physical or chemical
means (e.g., eugenol from clove leaf oil).
Essential Oil Specifications
Specifications for many essential oils, con-
cretes and absolutes have been published,
with the following being the main sources:
Fragrance Materials Association (previously
the Essential Oil Association of U.S.A.);
International Standards Organization; na-
tional standards organizations; Food Chemi-
cals Codex; the national pharmacopoeia s
and other official references. The limits
quoted in the various specifications may not
exactly correspond, and it is necessary to
Natural Flavoring Materials 201
ensure strict compliance with any given
standard where this is part of the title or is
a condition of sale (e.g., Oil of Peppermint
U.S.P.).
References: Essential Oils
Arctander, S. 1960. Perfume and Flavor Materials
of Natural Origin. Elizabeth, N.J.: Steffen
Arctander.
Bhattacharyya, S.C., Sen, N., and Sethi, K.L.
1989. 11th International Congress of Essential
Oils, Fragrances and Flavours. Proceedings
in 5 Volumes. New Delhi: Rekha Printers.
British Herbal Medicine Association. 1990.
British Herbal Pharmacopoeia. London:
Dorset.
Committee on Codex Specifications. Food
Chemicals Codex. 3rd Edition. Washington,
D.C.: National Academy Press.
Duverneuil, G., Valente, M. 1983. Robust,
original laboratory apparatus for determining
essential oil contents by distillation. Fruits.
38(3):201-207.
EOA. 1976. Specifications and Standards. New
York: Essential Oil Association of U.S.A.
Inc.
Furia, T.E. and Bellanca, N. 1975. Fenaroli's
Handbook of Flavor Ingredients, 2nd Edition,
Vol. 1 and 2. Cleveland: C.R.C. Press.
Galli, A., Franzetti, L., and Briguglio, D. 1985.
In vitro antimicrobial activity of essential oil
and extracts of spices used in foods. lndustrie
Alimentari. 24(227):463-466.
Guenther, E. 1948-1952. The Essential Oils,
Vol. 1-VI. D. New York: Van Nostrand Co.
Heath, H.B. 1983. Spices and aromatic extracts,
influence of technological parameters on
quality. 'Colloque G international G sur G les
G aromes G alimentaires G.' pp. 138-176.
London: Bush Boake Allen.
Heath, H.B. 1973. Herbs and spices for food
manufacture. Tropical Products Institute
Conference Papers. pp. 39-48. Bush Boake
Allen Ltd., Ash Grove, Hackney, London E8
4RH, UK.
Heath, H.B. 1972. Herbs and spices for food
manufacture. Trap. Sci. 14(3):245-259.
Hui, Y.H. 1991. Encyclopedia of Food Science
and Technology. New York: John Wiley &
Sons.
International Organization for Standardization,
1984. Spices, condiments and herbs-
202 Source Book of Flavors

determination of volatile oil content. swollen receptacle in strawberry). With

International Standard; ISO 6571-I984, pp. 4. exceptions, common fruits are consumed
Koller, W.D. 1988. Problems with the flavour fresh for dessert purposes. The ones not
of herbs and spices. In Developments in sold on the domestic market are used as a
Food Science, Frontiers of Flavor, ed. G. source of valuable products in processed
Charalambous, pp. 123-132. Amsterdam:
foods, the following being of particular
Elsevier Science Publishers.
Lawrence, B.M. 1978-1989. Essential Oils,
interest:
1976-1978, Parts 1 & 2, 1979-1980, 1981- a. Fruit pieces, pulp and puree.
1987. Wheaten: Allured Publishing Corp. b. Dehydrated fruit.
Lawrence, B.M. 1976-1978. Recent progress in c. Fruit juice and concentrates.
essential oils. (A regular article dealing with
d. Fruit powders.
several oils each issue.) Perfum. Flavor. 1,
(1), 1-5; (2), 17-20; (3), 45-46; (4), 31-34;
e. Jellies, jams and preserves.
(5), 11-15; (6), 31-34. Ibid 2, (I), 3-7; (2), Nuts are also fruits, but they will be
29-32; (3), 53-56; (4), 32-35; (6), 36-41; discussed separately as they form a clearly
(7), 4450. defined group. Botanically, fruits are varied,
Pafumi, J. 1986. Assessment of the micro-
but may be classified as shown below.
biological quality of spices and herbs. J. Food
Protect. 49(12):958-963.
Page, B.D. and Kennedy, B.P.C. 1975. Deter- Berries-Fruit in which the edible part is
mination of methylene chloride, ethylene pulpy and juicy containing numerous seeds:
dichloride, and trichloroethylene as solvent
residues in spice oleoresins, using vacuum Black currant Huckleberry
distillation and electron capture gas chroma- Blackberry (Bramble) Kiwi fruit
tography. J. Assoc. Offic. Analyt. Chern. Blueberry Loganberry
58(5):1062-1068. Boysenberry Raspberry
Pharmaceutical Society of Great Britain. Cranberry Red currant
1979. The Pharmaceutical Codex. London: Gooseberry Strawberry
Pharmaceutical Press.
United States Pharmacopoeia, 20th Edition.
1980. United States Pharmacopoeial Conven-
Citrus-Fleshy edible part is segregated
tion, Inc., Rockville, Maryland. into sections surrounded by a thick skin,
Zaika, L.L. 1988. Spices and herbs: Their anti- which itself contains strongly aromatic
microbial activity and its determination. J. essential oil:
Food Safety. 9(2):97-118.
Zuercher, K. and Hadorn, H. 1981. Equilibrium Citron Lime
moisture content and essential oil content of Grapefruit Mandarin (Tangerine)
commercial spices. Statistical evaluation of Kumquat Orange
data for approximately 750 samples. Deutsche Lemon
Lebensmittel Rundschau. 77(7):239-245.
Stoned Fruit-Fruit contains a single
seed (the stone or pit) surrounded by a
FRUIT FLAVORS
fleshy pericarp, which is normally the edible
Fruits are the matured ovary with or without part:
seeds and, in some cases, parts of the flower
previously associated with it. The wall of the Apricot Peach
fruit developed from the wall of the ovary is Cherry Plum
called the pericarp and may be either dry or Damson
fleshy. It is the fleshy pericarp that forms the
edible part of most fruits. Other associated Grapes-Small multiseeded or seedless
tissues are of value in certain fruits (e.g., fruits that grow on vines in clusters.

Melons-Characteristically large fruit
containing either a mass of seeds in the
center of a soft pulpy flesh or embedded
throughout a watery cellular flesh:
Canteloupe Musk melon
Honeydew Watermelon
Pomes-Fruit in which the body is
formed by an elongation and swelling of the
receptable surrounding the seed capsule:
Apple Quince
Pear
Tropical Fruits-These embrace many
fruit forms, but for convenience are classed
together:
Avocado Mango
Banana Pineapple
Date Pomegranate
Fig
The flavorist is not so interested in the
botanical aspects and prefers to group those
fruits of value in foods as flavorants more
simply as described below.
Simple Fruits
Dry: Pericarp dry and hard
a. Dehiscent (split open when ripe)
Legume-Splits along two edges
(peas, beans)
Follicle-splits along one edge
Capsule-splits variously (cardamom)
b. lndehiscent (do not split when ripe)
Achene (strawberry)
Grain (cereals)
Nut (almond, hazel, etc.)
Samara (winged seeds)
Fleshy: Pericarp mostly or entirely soft pulp
True berry (date, eggplant, grape, red
pepper, tomato)
Hesperidium (citrus fruits)
Drupe (almond, apricot, cherry, coconut,
olive, peach, plum)
Natural Flavoring Materials 203
False berry (cucumber, squash, melon,
cranberry, gooseberry, currant, banana)
Pome (apple, pear)
Aggregate Fruits
1. Drupelets [raspberry, blackberry (bram-
ble)]
2. Fleshy receptacle (strawberry)
Multiple Fruits
Pineapple, mulberry, breadfruit
There is some confusion over the use of
the words "fruit" and "vegetable." Many
fruits such as tomato, cucumber, eggplant,
etc., are generally regarded to be vegetables
probably because their association is with
savory food rather than sweet. By defini-
tion, fruits always develop from a flower
and are composed of one or more ripened
ovaries. Any edible plant materials that
are not so derived are strictly vegetables
(e.g., celery stalk). One vegetable that is
popularly regarded as a fruit is rhubarb,
which is the fleshy petiole of the leaf.
The structure of a particular fruit depends
on its botanical origins, but most edible
fruits consist of a skin or peel enclosing
the soft pulpy tissues in which may be
embedded one or more seeds. From a flavor
point of view, it is the fleshy pericarp that is
of most interest as these structures contain
the juice comprising sugars such as glucose,
fructose and sucrose, along with enzymes,
fruit acids, coloring matter and, in some
fruits, phenolic bodies including tannins.
The hard seeds are of little value as a source
of flavor, but stoned fruits give rise to
benzaldehyde when the stone or pit is
cracked open and subjected to hydrolytic
conditions.
There is a correlation between sugar
content, color, acidity and flavor as the fruit
ripens. The flavor usually develops to its
fullest aroma when the sugar content is at its
maximum and the color of the skin or peel is
at its brightest. When the fruit becomes
204 Source Book of Flavors

overripe, the color turns dull, the sugar centrated, applying first the fractional dis-
balance changes and the flavor loses its tillation at atmospheric pressure to obtain
volatile freshness. an alcoholic flavor distillate with a yield of
up to 2 percent of the input of juice put into
the still. The distillation is then interrupted
Fruit Juice and Flavor
and the juice cooled rapidly. The con-
Expressed fruit juice does not contain the centrate is then followed by a vacuum dis-
flavor of the whole fruit. The characteristic tillation. The condensates are fractionated
volatile aroma responsible for the distinctive to separate flavor and to recover alcohol.
profile is present in freshly processed juice The flavor yield of the distillation at atmo-
in less than 0.07 part per thousand and less spheric pressure and the first flavor fraction
in any juice that has been subjected to heat of the vacuum distillation are then combined
treatment. Only a compounded blend of with the concentrate. The mixture is a flavor
expressed juice and aromatic constituents concentrate containing the almost fully
recovered from the rest of the fruit will captured aroma of the fruit.
produce the flavor normally associated with This type of manufacture of fruit flavor
the whole fruit. The effect of concentrating concentrate requires a steam-heated water
fruit juices is of importance to the flavorist jacket covering about two-thirds of the still,
(see Hui 1991, Nelson and Tressler 1980, which can be used for heating as well as for
Ting and Rouseff 1986). cooling. The water jacket should contain
a steam coil. Also required is a properly
Concentration by Vacuum Distillation installed dephlegmator with a controlled
Evaporation of water from expressed fruit reflux ratio along with three receivers and a
juices and flavoring extracts by vacuum dis- condenser of suitable capacity. The vacuum
tillation yields concentrated soluble solids pump must be capable of keeping a constant
and extractive matter with little flavoring. pressure. Juice and flavoring extract will be
The aromatic substances are stripped from agitated vigorously during the flavor distilla-
the juice or flavoring extract during the tion at atmospheric pressure and during the
vacuum distillation. They separate in the concentration by vacuum distillation. The
form of vapor, part of which is recovered by agitator should have its propellers fan out in
condensation while the more volatile part a semicircle along the walls of the still and
is lost. Thus, the condensed material after reach up to the end of the heating jacket.
vacuum distillation retains only a part The vacuum in many of the stills used for
of the original flavor. Coupled with the concentration of fruit juices and flavoring
concentrated extractive matter, a flavor extractives should be kept at about 28 in.
concentrate is obtained that is similar in for best results. The flavor strength of con-
character but weaker in volatile components centrated flavor is proportional to the
to the flavor of the fruit from which it is degree of concentration. The peak of flavor
made. Fruit juices and extracts of cherry, strength is reached when expressed juice
raspberry, apple, and Concord grape will and fruit extractives are concentrated in
not be greatly changed by heating at boiling conventional vacuum stills to a final yield
temperature for a short period of time. of 25lb of fruit per gallon of fruit flavor,
Expressed juices and flavoring extracts of that is, after concentrated juice and flavor
fruit containing 15 percent alcohol will boil distillates are combined. The temperature
at 85°-90°C (188.6°-197.2°F). Kept at of the fruit juice and flavoring extract in
this temperature for about 10 or 15 min., the still rises with increased concentration
expressed fruit juices will retain extractive and often reaches 80°C (176°F) and more,
matter and color, but lose volatile aroma depending on the extractive matter and
by evaporation. Fruit flavors have been con- sugar content of the juice or fruit extrac-

tives. The agitation in conventional stills is
not turbulent enough to prevent changes of
aroma and taste resulting from the increased
heat of the concentrated medium. Besides
deterioration of flavor, the color may
caramelize with growing concentration if the
temperature is permitted to rise above 60°C
(140°F).
Concentration by Freezing
Concentration by freezing will yield a
superior fruit flavor. The freezing tempera-
ture during concentration varies from - 10°
to 0°F. Sugar added to fruit makes freez-
ing of alcoholic fruit juices and flavoring
extracts difficult.
Votator Continuous-Freeze
Concentration Process
The chief objective in concentration of food
products is to produce a concentrate that
retains as much as possible of the "natural"
odor and flavor. Concentration by freezing
results in a superior product that has not
FEED BLEND
TANK
.
'"' fiT
LOW CONCENTRATION
I e
If(: EQUIPMENT SUPPLIED BY VOT ATOA
FIGURE 7-1. Votator continuous freeze concentration system. (Heath 1981)
Natural Flavoring Materials 205
been subjected to any degrading effects of
high temperatures, long processing time, or
contact with foreign materials. The same
advantages apply to concentration of many
heat-sensitive nonfood products.
In the continuous process, the feed
is blended, slush frozen, concentrate and
crystals are separated, and the concentrated
product is sent to further processing. The ice
is then washed and discharged from the
system.
Referring to the flow diagram in Fig. 7-1,
fresh feed is pumped with pump (8) to the
feed blend tank. During its transfer to the
blend tank, the fresh feed is passed through
heat exchangers (7) and (5), where it is
precooled and some ice is melted. In the
blend tank the low concentrate is mixed
with some high concentrate and the liquor
from the centrifuge (6), which is approxi-
mately equal in strength to the fresh feed.
The resulting feed blend is pumped with
feed pump (1) through the Votator Heat
Exchanger (2) where a slush containing
HIGH
CONCENTRAT AT ION
TANK
HIGH CONCENTRATION
PRODUCT
• PRODUCT
PUMP
ll EFFLUENT PUMP
Courtesy of Votator Div., Chemtron Corp.
 206 Source Book of Flavors

approximately 40 percent ice is formed. centrate that is ready for final freezing,
This slush feeds directly to the continuous freeze drying or other processing, with
centrifuge (3), which separates it into the ice subsequent savings in heat requirement
phase, which goes to the refining tank (4), and greatly increased capacity in these
and the concentrate that flows to the high operations.
concentrate tank. Some of the concentrate Among the products successfully con-
is recycled to the feed blend tank, and the centrated using the Votator continuous-
rest is pumped to product storage, process- freeze concentration process are coffee, tea,
ing or filling. · and various fruit juices and extracts.
Part of the ice in the refining tank (4) is
melted. The resulting mixture is separated, Essence Recovery Process and Full
in the refining centrifuge (6), into the refined Flavor Concentrated Fruit Juice
ice phase that goes to the ice melt tank, and The invention of the process for recovering
the liquor that is fed back to the feed blend volatile aroma, the so-called "essence
tank. The ice is melted, and the water is recovery process," from fruit juices in 1944
pumped with the pump (9) back into the was followed by improvements in equip-
original process to produce more fresh feed, ment and design in subsequent years. It
or is discarded. gradually made possible the manufacture of
On start-up there may be no concentrate full flavor fruit juices in higher concentra-
available, so fresh feed would be pumped tion. The first commercially successful
through the Votator cooler and the cen- process for the recovery of volatile aroma
trifuge; the concentrate, which would was developed for apple juice by the Eastern
probably be lower than desired product Regional Research Laboratory of the U.S.
concentration, would be recycled to the Department of Agriculture in 1944. The
blend tank until steady-state operation was process was later modified to produce other
achieved. full flavor fruit juice concentrates.
Flow rates, concentrations, and operating A feature of the process is operation at
conditions will vary considerably with atmospheric pressure that minimizes aroma
type of product. In general, the system is loss in the vent gases. Heat damage to the
designed to handle feeds having a minimum juice is avoided by high-velocity, turbulent
of 6-10 percent solids, concentrating to flow in the pre heater. Essence recovery is
40 percent solids product with no large effected by condensation of the fractionated
intermediate storage and no second stage vapors combined with scrubbing of the non-
freezing. Typical concentrations in the condensable gases before venting to the
melted ice effluent from the system without atmosphere.
washing are 0.5 to 1.0 percent dissolved
material. Washing the centrifuge cake will Fruit Flavors with Other
reduce this concentration. However, the Natural Flavors (WONF)
economics of processing a particular pro-
duct, and reuse of the effluent will dictate Food and Drug Administration Regulations
the amount of washing justifiable. The regulations of the Federal Food, Drug
By using highly efficient, low-volume, and Cosmetic Act specify that fruit flavors
scraped surface heat exchangers and a new that are fortified with other natural flavors
technique for washing the ice produced, may be labeled as such, provided that at
Votator has eliminated the bulky equipment least 51 percent of the flavor strength is
and high hold-up volumes associated with derived from the fruit after which they are
those processes, which require crystal grow- named. Fortification of fruit flavors with
ing. In addition, the system incorporates extractives, distillates of other fruit or
energy savings and produces a chilled con- botanical ingredients, and essential oils adds

taste and aroma as well as increased color.
However, it does not increase the strength
of the original flavor of the fruit from which
it is derived. With the exception of cherry,
the fortification of fruit flavors with other
natural flavors may add a more or less
successful likeness, but does not necessarily
intensify the original aroma.
Measurements of Flavor Strength
Expressed juice differs in flavor strength
from an alcoholic extract derived from the
same fruit. One gallon of juice and flavoring
extract obtained from 10 lb. of fruit and
added alcohol is equal in flavor strength
to about 1.5 gal. of juice that has been
expressed from 10-12lb. of fruit.
Flavor evaluation by taste-made each
year after harvest by using both expressed
juices and alcoholic flavoring extracts of all
types of fruit commonly processed in the
manufacture of fruit flavors-showed, in
general, that 10 gal. of an alcoholic flavoring
extract derived from 10 lb. of fruit per gallon
of yield are required in a 100-gal. mixture
with water to identify a fruit flavor, while
about 15 gal. of juice are necessary to
identify the type of fruit from which the
juice has been expressed without the aid of
an alcoholic extraction. Thus, the threshold
of identification is to be considered basically
the measure that specifies the flavor strength
of an expressed juice or of a fruit flavoring
extract.
In compliance with the regulations of the
Federal Food, Drug and Cosmetic Act, the
specification of 51 percent flavor strength
derived from the fruit is equivalent to 5.1 gal.
of alcoholic flavoring extract obtained from
51 lb. of freshly picked or frozen fruit and is
mixed with 94.9 gal. of water to a 100 gal.
yield. It is also equivalent to 7.65 gal. of
juice expressed from 76.5 to 91.8lb. of
freshly picked or frozen fruit in a mixture
with water to a 100-gal. yield.
Fruit Pieces, Pulp and Puree
The increasing demand for all-natural
flavorings, particularly in such products as
Natural Flavoring Materials 207
ice cream and yogurt, has lead to a demand
for sliced fruit pieces, pulp and puree,
which may be incorporated not only for
their textural contribution but also for their
intrinsic flavor value. Such products are
normally canned and pasteurized without
additives, although sugar may be added
as a partial preservative. Compounded
flavorings, based on fresh or canned fruit
together with natural topping essence or
the appropriate imitation flavoring, color
and other permitted additives, are avail-
able from specialist manufacturers. These
may be added directly to the ice cream or
yogurt mix as appropriate to the desired
texture and nature of the end product. They
may be offered in unit packs, canned and
pasteurized, or in deep-freeze packages. To
ensure compliance with labeling regulations
of many countries, it is necessary for the
user to obtain a clear declaration of com-
position of such products, particularly the
presence of imitation topping flavors and
color.
Flavor and Processing
While individual fruits will be discussed
in the following sections, more general
information on the chemistry, processing
and formation of flavor can be found
in texts. The biochemistry of fruits and
vegetables is covered by Sinclair (1984),
Friend and Rhodes (1981), and Hulme
(1971). The processing of fruit and fruit
products is covered in the Encyclopedia
of Food Science and Technology (Hui
1991) as well as the coming Kirk-Othmer
Encyclopedia of Chemical Technology (25
volumes to be published/four volumes per
year beginning in 1991). Information on
the formation of fruit flavor and the flavor
compounds in fruit can be found in reviews
provided by Morton and Macleod (1990),
Maarse (1991), and Maarse and Visscher
(1989). The reference section of this chapter
contains complete citations of these works
as well as a sampling of the related literature.
208 Source Book of Flavors

Juice and Concentrate Tables

TABLE 7-15. Fruit juice and concentrate yields

Single Strength Juice Concentrated Fruit Juice

Brix Wt. of fruit to produce Brix Fold Wt. fruit to 1 gallon

1 gallon juice juice concentrate

Apple Juice 12° 12.5# 70° 7X 87.5#

Blackberry Juice 10° 13# 45° 5X 65#
Cherry Juice Montmorency 130 13# 68° 6X 78#
Cherry Juice Morello 14° 13# 68° 5.8X 75.4#
Grape Juice Concord 15° 12.5# 68° 5.6X 70#
Raspberry Juice Red 10.6° 12.5# 43° 5X 62.5#
Raspberry Juice Black 11.10 14# 47° 5X 67.5#
Strawberry Juice go 10.5# 34° 5X 52.5#

TABLE 7-16. How to reconstitute fruit juice concentrate to make standard juice

Gallons std. juice from one gallon concentrate

Brix of Concentrate 25 30 35 40 45 50 55 60 65

Apple 2.0 2.5 2.9 3.4 3.9 4.4 4.9 5.5 6.1
Hackberry 2.7 3.3 3.9 4.6 5.2 5.9 6.7 7.4 8.2
Cherry 1.8 2.3 2.7 3.1 3.6 4.1 4.6 5.2 5.7
Currant 2.5 3.1 3.7 4.3 5.0 5.6 6.3 7.1 7.8
Concord Grape 1.8 2.2 2.7 3.1 3.6 4.1 4.6 5.1 5.7
Elderberry (10 Brix) 2.7 3.3 3.9 4.6 5.2 5.9 6.7 7.4 8.2
Black Raspberry 2.4 3.0 3.5 4.1 4.7 5.3 6.0 6.7 7.4
Quince 2.0 2.5 2.9 3.4 3.9 4.5 5.0 5.6 6.1
Red Raspberry 2.5 3.1 3.7 4.3 5.0 5.6 6.3 7.1 7.8
Strawberry 3.3 4.1 4.9 5.8 6.6 7.5 8.4 9.4 10.4

SPECIFIC FRUIT PRODUCTS through yellow to red. The pulpy flesh

Apple
Apples are the fruit of Malus sylvestris
Mill., and are probably the most widely
distributed of the edible fruits. Com-
mercial crops are produced in Argentina,
Australia, Austria, Bulgaria, Canada,
France, Germany, Hungary, Italy, Japan,
Netherlands, Poland, Spain, the United
Kingdom and the United States.
The apple is a more or less spherical
pome of variable size formed by the enlarge-
ment of the receptacle, which becomes
fleshy and surrounds the carpels containing
the brown seeds. In most varieties, the skin
is smooth and varies in color from green
is usually white, but may be yellowish or
pinkish in some varieties.
The physical and chemical changes in
apples prior to and during harvest proceed
so slowly that it is almost impossible to
select any measure or index of maturity.
Apples are commonly sprayed with chem-
icals to control chewing insects such as the
codling moth and apple maggot. Various
types of machines and counteracting chem-
ical ingredients are used in washing the
fruit.
Most apples are graded before being
sold. Most states have grading laws for
apples, which require that all apples sold
in closed containers must be marked as to
TABLE 7-17. True fruit extracts from extracts

x =Volume of b =Volume of
Concentrate Essence Per y =Volume of Formulations to Make
Concentrate a= Pounds of Representing Fold of Gallon Essence Per 1 Gallon True Fruit
Product Fold Fruit per Gallon 251bs. Fruit Essence Concentrate Gallon Extract Extract

70° Apple Juice 7X 84 38.1 oz. 150 6.0oz. 1.8oz. 38.1 oz. 70° Apple
1.8oz. 150X Essence
25.6oz. 95% alcohol
Water-q.s. 1 Gal.
43° Blackberry Juice 5X 67.5 47.5oz. 100 6.4oz. 2.38oz. 47.5 oz. 43° Blackberry
2.38oz. 100X
Essence
25.6oz. 95% Alcohol
Water- q.s. a Gal.
68° Concord 5.6X 70 45.7oz. 100 7.2oz. 2.63oz. 45.7 oz. 68° Grape
2.38oz. lOOX Essence
25.6oz. 95% Alcohol
Water-q.s. 1 Gal.
68° Cherry Juice 6X 78 41.0oz. 100 7.68oz. 2.46oz. 41 oz. 68° Cherry
2.46oz. 100X Essence
25.6oz. 95% Alcohol
Water-q.s. 1 Gal.
45° Red Raspberry 5X 62.5 51.2oz. 100 6.4oz. 2.56oz. 51.2oz. 45° Raspberry z
~

Juice 2.56oz. 100X Essence

....
~
..,
25.6oz. 95% Alcohol a
Water-q.s. 1 Gal. ::!1
~

47° Black Raspberry 5X 67.5 47.4oz. 100 6.4oz. 2.37oz. <

0
47.4 oz. 47° Raspberry
::l.
Juice 2.37 oz. 100X Essence ::l
(]Q
25.6oz. 95% Alcohol
Water-q.s. 1 Gal. a:::
~
....
0
34° Strawberry Juice 5X 52.5 6l.Ooz. 100 6.4oz. 3.05oz. 61 oz. 34° Strawberry ::l.
~
3.5 oz. 100x Essence r.;;
25.6oz. 95% Alcohol
Water-q.s. 1 Gal. N
0
\0
210 Source Book of Flavors

variety., grade, size range or count of the

fruit in the box; quantity of the contents or
the net weight; and the name and address of
the packer or repacker.

Apples Used for Drying,

Canning, and Freezing
Apples possessing good cooking qualities
are most desirable for preparing dried,
canned, and frozen products. Grades of
apples used for processing vary from field-
run fruit to culls of an arbitrarily establish-
ed minimum size. Apples purchased from
packing houses will consist of definite
grades. The factors governing the quality of
apples for fresh market use apply equally
in determining their quality for processing.
The major portion of apples used in process-
ing are obtained from fresh fruit packing
houses and, therefore, have been washed to
remove spray residue and are free from Courtesy ol The Fitzpatrick Co.

decay. Most apples prepared for preserva- FIGURE 7-2. The Fitzpatrick comminuting
tion are peeled by machines that pare the machine. (Heath 1981)
fruit mechanically. Bits of skin, bruises and
defects remaining after the peeling opera-
tion are removed by hand. The fruit is then
sliced or cut to the desired form. From 25 to
45 percent of the fruit is lost in the peeling,
coring, and trimming operations, depending
on the size and condition of the fruit.

Apple Juice
Fresh apple JUICe is subject to rapid fer-
mentation. In the United States, the early
distinction between the fresh and the Courtesy ol The Fitzpatrick co.
fermented juice was made by simply term-
FIGURE 7-3. Dismantled comminuting chamber
ing the respective products as cider or showing blade chamber with hammer-like carvings.
fresh cider, and hard or fermented cider. (Heath 1981)
Generally, apple juice is the product that
contains less than 0.5 percent alcohol,
by volume, regardless of its method of
preservation. Products containing more
than 0.5 percent and less than 8 percent
alcohol, by volume, are termed ciders.

Preparation
Apples to be used for juice are inspected. FIGURE 7-4. Comminuting sieves numbers 1, 2, 3,
Decayed and badly damaged fruit is re- 4, 5. (Heath 1981)
 Natural Flavoring Materials 211

moved. The fruit is thoroughly washed it has been found economical to press in
to remove dirt and to reduce the micro- two stages. The pomace is usually passed
organisms on the surface. By thus reducing through a pomace picker and transferred to
the initial inoculation of the juice with storage bins for further processing.
organisms, greater stability to fermenta- Utmost cleanliness is required in operat-
tion is obtained during processing and the ing a press room to assure that undesirable
quality of the juice is improved. To obtain off-flavors are not imparted to the juice.
the maximum juice yield, it is necessary to Besides frequent washing of the equipment
disintegrate the apple tissues (Fig.7-2-7-4). to remove accumulated pulp and spilled
Flavor constituents and vitamins con- juice, special attention is given to the cloths
centrated directly beneath the skin are and racks. Unless they are periodically
expressed more completely after thorough washed and aired, this equipment tends to
disintegration. impart a musty, stale flavor to the juice.
Apple juice flows from the press as an
Maceration amber fluid; it may darken slightly within a
Maceration consists of holding the milled few minutes after pressing. The change in
fruit for a period of 12 or more hrs. before color during pressing is caused by enzymatic
pressing, but it is not used in the commercial browning of the juice. The nature of con-
manufacture of unfermented apple juice. ventional apple presses and delays inherent
Maceration results in a more fully flavored in methods of pressing the pulped fruit
juice, but leaves a harsh aftertaste. How- make it impossible to retain the natural
ever, the maceration for 24 hrs. of 35 to color of the apple juice unless special pro-
40 lb. of presscake per 100 gal. of juice cesses are used.
yields an improved flavor. The natural apple color and flavor in the
juice can be retained by the use of ascorbic
Pressing acid. Chilled apples are ground rapidly and
Several types of presses are used to remove an apple juice solution of ascorbic acid is
the juice from the pulp (Fig. 7-5). With sprayed on the pomace during milling at a
the exception of small home presses, which rate of 6 to 12 g of ascorbic acid per bushel
usually operate by means of a screw, of apples (40- 45lb. ). After pressing, the
practically all apple juice is pressed with juice is dearated, flash pasteurized, and
power-driven hydraulic presses, which sealed in containers as rapidly as possible to
vary in size and style. The most common avoid darkening.
procedure for pressing juice is to make a Beside soluble constituents responsible
single pressing, after which the pomace is for its flavor , aroma and color, freshly
separated from the cloths. In some cases, pressed juice also contains more or less
suspended solids ranging in size from lumps
through cellular pulp, to finely divided,
dispersed colloidal material. The larger
pieces are usually removed from the juice by
screening at the press.
Removal of suspended solids by direct
filtration is difficult because of mucilaginous,
hydrophilic gums and pectinous materials
contained in freshly pressed juice. Many of
the suspended solids are colloidal and reten-
Courtesy of Hubert C. Stollenwork, Inc. tive filters are required to produce a clear
FIGURE 7-5. The pneumatic Willmess presser. product.
(Heath 1981) A number of enzyme preparations have
212 Source Book of Flavors
been employed to clarify apple juice. Their
action depends on their ability to hydrolyze
colloidally suspended material into either
more or less soluble substances.
Commercial preparations of enzymes,
available in the United States as "Pectinal,"
are sufficiently potent to permit the rapid
handling of large quantities of juice. Gelatin
is usually added to these preparations to
facilitate precipitation and stabilize the
enzymes in solution. The colloidal system of
the juice is so completely broken down that
the juice may be rapidly filtered without
difficulty from clogging. The delicate, mild
flavor of the juice makes clarification with-
out a flavor change difficult.
The effect of enzyme treatment on apple
juice varies with the preparations used. Off-
flavors may be contributed to the juice unless
the enzyme preparation is freed from such
flavors during manufacture. Commercial
preparations of pectin-decomposing en-
zymes are available that do not contribute
noticeable flavor, and their principal effect:
on the juice is to reduce viscosity through
decomposition of pectin substances.
Filtration
To effect complete removal of suspended
material from clarified apple juice, it is
necessary to filter or centrifuge the juice
(Fig. 7-6). Filtration reduces the viscosity
and alcohol-insoluble fractions of the juice.
The loss in viscosity may be restored,
FIGURE 7-6. Type R semi-automatic Funda-filter
station. (Heath 1981)
if considered desirable, by replacing the
pectin lost during clarification. Losses in
other constituents that contribute to the
flavor and properties of apple juice depend
on the type of clarification treatment used,
but in general these changes are not great.
Filtration also has the effect of removing
microorganisms from juice.
Carbonation
Clarified and filtered juice may be car-
bonated in equipment used for the carbona-
tion of water by the carbonated beverage
industry, provided corrosion-resistant met-
als have been used in those parts that come
in contact with the juice. About two and a
half times as much carbon dioxide as apple
juice has been suggested as suitable for this
beverage. A higher carbonation is desired
for very sweet juice than for highly astringent
juice.
Although carbonated apple juice has
been described as comparable in flavor
appeal to other carbonated beverages,
commercial production of this product is
limited.
Blends with Other Fruit Juices
The fresh, but mild, fruit flavor of apple
juice serves as an ideal base and is relatively
inexpensive to produce in comparison with
juices prepared from other fruits.
Preservation
Apple juice not intended for immediate
consumption must be subjected to some
preservation process to prevent spoilage.
The most important commercial method of
preservation is pasteurization. The most
satisfactory method for preserving the fresh
flavor of apple juice is by freezing. Juice
preserved in this manner need not receive
any heat treatment, and flavor changes
that occur in canned juice during storage
at higher temperatures are retarded.
Chemicals used in the commercial preserva-
tion of apple juice are confined principally
to sodium benzoate, sulfurous acid includ-
ing its salts, and C02 •

Concentration
The term "juice concentrate" is usually
applied to fruit juices that have been con-
densed by the removal of water and which,
when rediluted with water, resemble the
original juice in composition. Concentrated
juices are usually unpalatable because of
their high acid content. The term syrup is
generally applied to products prepared from
juice with the addition of sugar, or in which
the acid has been neutralized sufficiently
to make it palatable in a concentrated
form.
Concentration by Vacuum Distillation
To retain the natural flavor of fresh apple
juice, it is necessary to concentrate the juice
by evaporation at temperatures sufficiently
low to minimize chemical changes.
One of the principal problems encoun-
tered in the concentration of apple juice
by evaporation is the loss of volatile,
aromatic flavor constituents, and con-
centrates prepared by atmospheric or
vacuum evaporation are practically devoid
of the characteristic aroma of fresh apple
juice. Among the methods developed for
recovering these flavor constituents, one
consists of passing the first vapors removed
during the evaporation process through
a cold concentrate obtained by previous
evaporations. Another consists of stripping
the juice of aromatic constituents by a
preliminary passage through a vacuum pan
and condensing this first vapor for return to
the final concentrate. In both methods, it is
necessary for the concentration of the juice
to be carried beyond that desired in the final
product because of the dilution by the
aromatic fraction.
The most efficient process for recovering
the volatile flavor constituents from apple
juice is the process of stripping these
substances from juice by heating in an
evaporator to obtain a 10 percent, flash
vaporization that removes all of the volatile
substances. The condensate is then treated
in a fractionating column where the volatile
flavoring constituents can be concentrated
Natural Flavoring Materials 213
up to 150 times that of the original juice at
atmospheric pressures.
The more complete removal of volatile
constituents, which is obtained by the rapid
evaporation, and their subsequent enrich-
ment through fractional distillation make
it possible to prepare full-flavored apple
juice concentrates. When reconstituted with
water, they are indistinguishable in taste
and aroma from fresh apple juice. This
process for recovering and concentrating the
volatile, aromatic components of apples has
also proven to be a practical method for the
commercial preparation of volatile fruit
concentrates from a variety of fruits.
In the United States, apple essence
manufacture is subject to regulation by
the Bureau of Internal Revenue, Treasury
Department, because minute traces of
alcohol usually present in the juice are con-
centrated to above 0.5 percent by volume of
essence.
Concentration by Freezing
The process of concentration by freezing
avoids the danger of damaging the flavor of
the juice by heat, and losses in volatile,
aromatic constituents are held to a very low
point. Extensive commercial development
of freezing concentration has been handi-
capped because of difficulties in practical
application and the cost of the process.
Concentration by reverse osmosis
The application of reverse osmosis for the
concentration of apple juice and subsequent
aroma recovery has been discussed by
Matsura et al. (1975), Sheu (1987), Chua et
al. (1987) and Moresi (1988). Details of
commercial apple processing are discussed
in various texts such as Hui (1991).
Apricot
The apricot (Prunus armenliaca L.) is an
almost spherical fruit, 1-2 in. in diameter,
with a single seed surrounded by a stone
and a fleshy pericarp. The orange-yellow
colored skin is nearly smooth. Commercial
 214 Source Book of Flavors
crops of apricot are produced in Australia,
Hungary, many Mediterranean countries,
South Africa and the United States
(California, Utah and Washington produc-
ing products with the best flavor). The
Royal, Tilton and Blenheim varieties are
the most suitable for juicing and flavor
production. Dried apricots are of value
for dessert products and lib. of dried
fruit is derived from 4-7lJzlb. of fresh
apricots. The flavor is significantly reduced
by dehydration; almost all of the charac-
teristic top notes are lost, the main flavor
being due to nonvolatile acids (mainly malic
and citric acids), overlaid with the aromatic
products of the Maillard reaction.
The fruit ripens slowly, during which the
composition of the constituents changes
significantly and the total acidity falls as the
sugar content increases. Apricot has a more
distinctive and characteristic flavor profile
than peach, which it resembles.
Avocado
Avocado (Persea americana Mill.) is a large
pear-shaped fruit (hence the name Avocado
pear) with a rough leathery green skin con-
taining one large seed. Three types are
recognized commercially, depending on
their source: Mexican, Guatemalan and
West Indian. In addition, there are many
hybrid varieties (e.g., Fuete) of commer-
cial importance. Avocados produced in
California are of the Fuete (Oct.-Mar.)
or Hass (Apr.-Aug.) vanetJes, being
intermediate between the Mexican and
Guatemalan types and enabling fruit from
this source to be available almost all year.
Avocado is unusual in that the fruit may be
left on the tree until required as no softening
occurs until the stem is broken. The Fuete
variety remains green when fully ripe,
but the skin of the Hass variety changes to
black. Avocados from Florida are mostly
hybrids of the West Indian variety. The
fleshy mesocarp is the part that is edible.
This consists of tissue containing special oil
cells carrying from 8 to 35 percent lipids,
depending on the variety.
Banana
The banana is the fruit of several Musa
species, primarily Musa paradisiaca L. (the
plantain), M. paradisiaca var. sapientum
Kuntz. (the common banana) and M.
calvendishii L. (the dwarf banana). The
thick skin of unripe bananas is green and
it is in this stage that they are normally
harvested and picked for shipment. As
the fruit ripens, the skin turns yellow and
then brown as it overripens or is in any
way damaged. On the plant, bananas are
grouped together as "hands" attached to
a central stem. The number of individual
bananas in a "hand" is variable. Bananas
grow throughout the tropics, but are com-
mercial crops in Central and South America,
the West Indies, the Canary Islands and
West Africa. Bananas are of value in desserts
and cut pieces are used in flavored yogurt,
etc. The fruit has a distinctive but mild
flavor and the pulp is of little direct value as
a source of flavor in processed foods.
Blackberry (Bramble)
The fruit of several species of Rubus are
popularly known as berries, but botanically
are aggregates of drupelets more or less
firmly attached to a receptacle. The black-
berry or bramble is the fruit of Rubus
allegheniensis L., which grows wild through-
out the eastern part of North America and
in Europe. Cultivated vanetJes (e.g.,
Bedford Giant, Himalayan Giant) are gen-
erally larger, have fewer seeds, and a much
better flavor when ripe than the wild black-
berries, although the flavor of these can
be much enhanced by a short fermentation
period. Blackberries are a dessert fruit, but
may also be made into jam and jelly.

Black Currant
See Currant
Blueberry
Blueberry is a widely known and pleas-
antly flavored fruit from several species of
Vaccinium, but mainly from V. corymbosum
L. The fruit is a many-seeded berry, about
1 em. in diameter with a smooth blue-black
skin usually with a bloom. There are three
types of blueberry grown commercially in
the United States: Highbush, Lowbush and
Rabbiteye [a species, V. ashei, Read, which
will grow on soil unsuitable for the other
varieties].
This is a dessert fruit that is popular
for breakfast in North America and
Scandinavia. It is also much appreciated in
sauces, pies and certain baked goods, and is
gaining wide acceptance in yogurt. The fruit
is not suitable for juicing.
Boysenberry
Boysenberry (Rubus ursinus Cham. &
Schlecht, var. Ioganobaccus Bailey) is a
trailing plant not unlike loganberry. The
fruit consists of drupelets firmly attached to
a receptacle and is very dark red in color.
Cherry
Cherries are the fruit of Prunus auium
L. (sweet cherry) or P. cerasus L. (sour
cherry). There are five main types: (a)
Mozzard (wild sweet cherry); (b) Heart
(var. Juliana Koch), which is heart-shaped
and has a soft pulp; (c) Bigarrean (var.
duracina Koch), which is hard-fleshed; (d)
Duke (P. gondouinii Rehd.), having a soft
acidic pulp; and (e) Sour (P. cerasus L.),
which is soft-fleshed and acidic. The color of
these varieties varies from pale cherry-red
to dark red to almost black.
Growing on shrubs and trees of moderate
size in temperate regions of both hemi-
spheres, cherries, both of the sweet and sour
varieties, have become the most commonly
Natural Flavoring Materials 215
cultivated of all the tree fruits in North
America. The cherry is a well-flavored
subacid fruit and is used for the preparation
of preserves, syrups, in the manufacture of
liqueurs and, to a large extent, in carbonated
beverages.
Types of Cherries
English Morello Cherries
In the manufacture of cherry flavor, prefer-
ence is given to the English Morello variety.
Besides its pronounced fruity note and
extractive richness, Morello cherries yield
a desirable shade of red coloring charac-
teristic of cherry. They are the last of the
cherry fruit to mature and are generally
harvested about the first of August.
Montmorency Cherries
Montmorency cherries yield a juice of bright
red color and a faint fruity flavor in the
juice. The flavor and coloring of cold
expressed Montmorency cherry juice fade
out after a short period of storage. How-
ever, the expressed juice from preheated
Montmorency cherries retains an intensified
aroma and color. The fruit is fully ripe for
harvest by the middle of July.
Sweet Cherries
The West Coast of the United States pro-
duces large quantities of sweet cherries.
Their aroma and taste do not have any of
the characteristics of the sour cherries,
which are useful in the manufacture of
flavors. Sweet cherries lack acidity. Their
seeds develop little or no cherry or
benzaldehyde flavor after hydrolysis.
Dalmatian Cherries
Dalmatian cherries are named after their
place of origin, Dalmatia, a region of
Yugoslavia. They are imported in semidried
form, packed in wooden kegs of lOOlb. or
50 kg., net weight. Extractives of partly
dried Dalmatian cherries are often used
to blend with cherry flavors. However,
Dalmatian cherries should be processed
216 Source Book of Flavors

no later than three months after drying. Bitter Almond (Amygdala amara)
They develop mold and become wormy on The volatile oil of cherry seed is identical
prolonged storage. Dalmatian cherries to that of bitter almond; both contain
should be soaked and extracted with a mix- amygdalin. Oil of bitter almond is often
ture of cherry juice and alcohol to substitute used to substitute for benzaldehyde obtained
for the juice, which drains off and partly by hydrolysis of cherry seeds.
evaporates during drying. After extrac- The principal constituents of bitter almond
tion, the exhausted Dalmatian cherries and are fixed oil, the glucoside amygdalin, and
pitted seeds are ground and subjected the enzyme emulsion. After removal of the
to hydrolysis to develop benzaldehyde. fixed oil, the cake of the bitter almonds is
Alcohol is added and the mixture distilled mixed with warm water at 55°C (131°F),
at atmospheric pressure. The condensate allowed to hydrolyze, and is then subjected
is then fractionated and yields a very fine to steam distillation. The distilled oil con-
cherry and benzaldehyde flavor. tains more than 80 percent benzaldehyde,
partly in a free state but mainly in combina-
Wild Cherry tion with a small amount of hydrocyanic
The wild cherry is a small fruit with a acid. The latter is removed chemically by
delicate aroma and a faintly bitter taste. The heating the distilled oil with a sulfite, or with
skins and kernels of wild cherries yield a slaked lime and an iron salt, and then the
more pronounced fruit and benzaldehyde mass is redistilled. Oil of bitter almond is
flavor than those of any other variety heavier than water. Oil of bitter almond is
of cherry. Wild cherries are harvested in also derived from the seeds of the apricot.
limited quantities to satisfy only advance The oil derived from the seeds of the
orders. They are sold in dried form. Wild almond tree is imported mainly from
cherries should be extracted with the juice southern France, Spain, and Italy. It is
of other cherries. They will yield a delicious obtainable in two varieties: one containing
flavor. hydrocyanic acid besides benzaldehyde, the
other being free from Prussic (hydrocyanic)
acid, often labeled in abbreviated form-
Cherry and Benzaldehyde Flavor FFPA.
Oil of bitter almond is colorless and will
Wild Cherry Bark acquire a yellow color with storage. It will
Wild cherry bark is the dried stem bark oxidize on exposure to air to form benzoic
derived from the wild, or black cherry acid crystals, and should therefore be
tree, Prunus serotina, which grows through- kept in tightly closed and completely filled
out the northern and central United States. containers.
The chief constituent of the bark is d-
mandelonitrile glucoside or prunasin Cherry Kernel Oil
(C 14H 17N06 ), which has properties similar There is no production in the United States.
to the amygdalin of almond seed. The other
constituents are benzoic, trimethylgallic and Cherry Pit Distillate
p-coumaric acids, tannins, and volatile oil. This is a flavor obtained by subjecting the
If ground or pulverized, wild cherry bark coarsely ground seeds of the cherry pits to
is treated with warm water of about 55°C hydrolysis, followed by its distillation with
(131°F) and enzymes will hydrolyze prunasin alcohol and water.
to benzaldehyde, glucose and hydrocyanic
acid. The latter is removed chemically or Kirschwasser
is lost during the distillation. Distillation Kirschwasser is made by fractional distilla-
yields a flavor similar to Kirschwasser. tion of a fermented mash of cherries and

crushed seeds. The increased tempera-
ture of the mash during the fermentation
hydrolyzes the amygdalin of the seeds to
benzaldehyde . A 50 to 55 percent alcohol
content of the distillate yields the best
aroma of Kirschwasser.
Expressed Cherry Juice and
Flavoring Extract
Cherry fruit flavors are made mainly from
frozen pitted or unpitted fruit. The expressed
juice of frozen cherries has the same natural
aroma and bright color of the cold pressed
juice of fresh fruit. Complete thawing of
frozen cherries is to be avoided since thaw-
ing subjects the frozen fruit to oxidation,
which results in damage to both its fresh
volatile aroma and its color. The proper
procedure in the manufacture of cherry fruit
flavor requires that alcohol be added to the
partly defrosted cherries before further
processing. It is also advisable to process
fruit by treatment with a pectic enzyme
prior to the addition of alcohol or by its
addition to the expressed juice, in order to
hydrolyze the pectins. The enzyme serves to
convert the pectins partly into soluble sugars
and also serves to precipitate pectic acid .
Expressed cherry juice should be stored
in stainless-steel containers to avoid ex-
posure to air and to aid in the precipitation
and settling of proteins, carbohydrates and
other suspended matter.
Centrifugal Clarification of Cherry
Juice and Flavoring Extracts
The clarification of fruit juices and of
flavoring extracts can be accomplished by
settling or sedimentation , by filtration, and
by centrifugal clarification. The centrifugal
clarification is related to sedimentation
methods. In the latter instance , the force of
gravity is used to separate the solid material
from the lower specific gravity liquid in
which it is dispersed, or the heavier liquid
from a lighter liquid, with each type of
material settling in accordance with its
specific gravity.
In the case of centrifugal clarification,
Natural Flavoring Materials 217
this action is speeded up by the centrifugal
force developed by rotation. This force,
when expressed in terms of gravity, is many
times greater than gravity. The solid will
move horizontally farthest from the center
of rotation, the water will form a layer next
to the solid, and finally the oil will form a
third layer.
Westfalia KG clarifiers have been
designed particularly for use in the flavor-
ing extract industry (Fig. 7-7). The KG
clarifier bowl is divided into several annul
chambers through which the liquid passes
progressively, thus removing the solids in
gradual stages governed by the size and
specific gravity of the particles . As soon as
the material to be clarified enters the bowl,
it is subjected to centrifugal forces , which
remove the biggest and heaviest particles
in the first chamber. Smaller and lighter
particles are removed in each successive
chamber, with the lightest and smallest
being removed in the final, outer chamber,
where the centrifugal force is greatest.
In this way, even the finest particles are
trapped and removed.
Separation of Volatile Aroma
and Concentration of Juice
Filtered fruit juice, e.g., Morello cherry
juice, is pumped (follow flow diagram in
FIGURE 7-7. Westphalia clarifier. (Heath 1981)
218 Source Book of Flavors

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Courtesy of Food Engineering

FIGURE 7-8. Flow diagram of the essence recovery process. (Heath 1981)

Fig. 7-8) from the feed tank (1) at a rate
controlled by the rotameter (2) into the
preheater (3), where temperature of the
juice is raised sufficiently to flash into vapor
in the vaporizer (4), a fraction containing all
aromatics and volatiles.
In the centrifugal-type separator (5) juice
and essence-bearing vapor are separated,
the former routed to the juice concentrating
system, the latter to essence concentrating
equipment. The vapor flowmeter (6) pro-
vides a gauge for regulating steam to the
prevaporizer, thus regulating vapor volume.
Vapor now enters a three-part fractionating
column (7) with stripping, rectifying and
reboiling sections.
In the surface condenser (8), the
aromatic-containing fraction is condensed
and subcooled, a portion removed as 150-
fold essence, and the remainder returned
for refluxing to the top of the fractionating
column. Essence concentration is deter-
mined by controlling the draw-off rate of
essence in relationship to juice feed rate, as
indicated on the rotameter (9).
The last three-coil unit (10) in the essence
recovery system is ammonia refrigerated.
Here, essence is cooled before removal
from the system, and noncondensable vent
gases are cooled before they are back-
washed in the scrubber, and "bottom"
liquid is cooled before introduction to the
top of the scrubber. Juice from the separator
(5) is cooled to evaporator temperature in
the flash tank (11) under relatively high
vacuum aided by recirculation. The "falling
film" type evaporator is designed for low
operating volume and minimum juice reten-
tion time. Evaporator level is instrument-
controlled.
From the evaporator, vapor and con-
centrate discharge into a separator (12),
with vapor then entering the barometer
condenser (13) while the concentrate is
recirculated by a pump (14) and a portion is
withdrawn to finished product storage at
desired density.
Cooling and flashing are aided by re-
circulation of a portion of the cooled juice.
Natural Flavoring Materials 219
The unique recirculation method has the
additional advantage of preventing foaming.
The lower section of the flash chamber is
extended to provide a feed surge-tank to
supply the evaporator.
Retention time of juice in the evaporator
is reduced to a minimum by means of a unit
of the "falling film" type. This type of
evaporator not only removes any possibility
of overheating the juice, but also reduces
to a minimum the volurrie of juice in the
system.
Minimum operating level in the evap-
orator is automatically maintained by a
pneumatic, differential-pressure type in-
strument that throttles an air-operated,
diaphragm-type juice-feed valve at the inlet
to the evaporator. Juice is recirculated
in the unit by means of a pump, a portion
of juice being withdrawn at the desired
product density and then delivered to
storage.
Since the essence solution is stable and
relatively free from deterioration under
normal storage, the volatile aroma and
flavor constituents may be added to the con-
centrate at the time of packaging.
In this production, the volatile aroma is
separated in two fractions, each of 100-fold
strength representing 100 gal. of juice. The
first fraction, yielding 72 gal., has 0. 9 percent
alcohol and 0.036 percent benzaldehyde. A
second fraction of 13 gal. of 100-fold essence
is obtained; it contains no alcohol but 0.052
percent benzaldehyde.
The cherry juice concentrate produced as
indicated above has a soluble solids of 41 o
Brix. This concentrated juice should be
put into stainless-steel drums and stored
at freezing temperature in a cold-storage
warehouse. Acids may separate to the
bottom of the container of frozen con-
centrate. However, with the defrosting
of the juice the acid dissolves easily. In
using frozen concentrated cherry juice, it is
advisable to add alcohol before complete
thawing to avoid fermentation.
220 Source Book of Flavors
Full Flavor Formula
A full flavor concentrated Morello cherry
juice consisting of concentrated soluble
solids of 41° Brix and additions of both
fractions of the separated volatile aroma
requires the following per one gallon of
mixture: 3.55 percent of the first fraction of
the volatile essence, 0.43 percent of the
second fraction, and 96.02 percent of the
concentrated juice of 41° Brix.
Flavor Property
One gallon of the full flavor concentrated
juice is equivalent in aroma, flavor strength,
natural color, solids, and acid, to about
4 gal. of hot expressed juice from 44lb. of
Morello cherries.
Flavor Measurements
A flavor test made in 100 parts water shows
a threshold of perception of 1.5 percent;
color: faint; threshold of identification: 2.5
percent; color: distinct.
Concentration to 68° Brix
The concentrated juice of 41° Brix can
be treated with Pectinol and filtered. The
filtered juice can then be further con-
centrated. Two gallons will yield 1 gal. of
a 68° Brix concentrate. The concentrated
juice can be filled in stainless-steel drums
and stored in cold storage at 1.7°C (35°F).
The taste of the concentrate of 68° Brix
will not change in five years. Also, the color
of this concentrate retains its dark red shade
and brilliancy. It can be assumed that this
concentrate may remain stable indefinitely.
The 68° Brix Morello cherry juice is more
economical to use than the 41 o Brix con-
centrate. No separation of acids occurs in
the 68° Brix concentrate if it is stored at
room temperature.
The high concentration of the 68° Brix
juice also permits storage at room tempera-
ture and makes it possible to partially use
a storage drum without endangering the
remainder of the contents.
Full Flavor Formula
One gallon of full flavor concentrated juice
made from 68° Brix concentrate and the
aromatic fractions requires 5.24 parts of the
first fraction of the volatile aroma, 0.86 parts
of the second fraction of volatile aroma, and
93.90 parts of 68° Brix concentrate.
Flavor Profile
One gallon of the full aromatic concentrated
Morello cherry juice is equivalent, in
aroma, flavor strength, natural color, solids,
and acid, to 8 gal. of hot expressed juice
from 88lb. of Morello cherries.
Flavor Measurements
A test made in 100 parts of water has a
threshold of perception of 0.75 percent;
color: faint; threshold of identification: 1.25
percent; color: distinct.
Hot expressed juice, to some extent,
helps to intensify the coloring matter; how-
ever, the heat largely inactivates enzymes
in the seed in the kernel and destroys the
volatile freshness of the flavor. Fruit should
not be heated if it is used in the production
of fruit flavors.
Citrus Fruits
The citrus family is one of enormous com-
mercial importance not only for its nutritious
and flavorful edible fruits, but for several
other valuable aromatic products derived
from the leaves and flowers of these plants
(e.g., Oil of Petitgrain, Oil of Neroli).
Citrus fruits have a common structure
and consist of: (a) a variously colored peel
or rind whose outer layer contains numer-
ous oil sacs or glands (flavedo) filled with a
highly aromatic essential oil; (b) a spongy
layer (albedo) containing pectinous matter;
(c) an inner pulp or flesh whose spindle-
shaped cells are separated into segments
surrounded by a thin membrane; these cells
contain the juice; (d) seeds may or may not
be present in the segments; (e) a central
core of tissue similar to the albedo. In citrus

JUICe processing, the segment membranes
and the inner core tissues are called "rag."
The following citrus fruits are of major
importance in flavoring.
Citron
The oblong-oval fruit of Citrus medica L.
looks not unlike a large lemon, about 8 in.
long and having a thick yellow skin. This
fruit is cultivated in California, Florida and
Puerto Rico. It is inedible in the raw state,
but the skin yields an aromatic essential oil
and the sliced fruit may be fermented in
brine prior to steeping in sugar solution to
make "candied peel," which is widely used
in cake and other bakery products.
Grapefruit
The large fruit of Citrus paradisi Macf.,
is known also as Pomelo. This spherical,
smooth, yellow-skinned fruit is 4-6 in. in
diameter and has white or pink-colored
flesh, with or without seeds, depending on
the variety. The grapefruit has an acid,
sometimes bitter, taste with a pleasing
and refreshing flavor. The natural juice is
canned or may be concentrated and frozen.
Grapefruit is a commercial crop in Florida,
California, Texas, Arizona, the West Indies
and North Africa (Morocco).
Kumquat
Originating in China and Japan, the fruit
of Fortunella margarita Swingle, was intro-
duced into the United States and has gained
some popularity. Kumquat may be made
into preserve or candied for use in baked
goods.
Lemon
Lemons are universally popular and are
produced commercially throughout the
Mediterranean region (particularly in Sicily,
Israel and Greece), California and, to a
limited extent, in Florida. They are the
familiar yellow oblong-oval fruits of Citrus
limon L., about 2Yz-4in. long with a well
defined nipple-like end. The fruit is very
acidic, although some sweet varieties are
Natural Flavoring Materials 221
known. They are harvested while still green
and allowed to ripen under controlled con-
ditions to enhance the flavor.
The peel contains a highly aromatic
essential oil containing about 2 percent
citral (quantity dependent upon the growing
region). The production of this oil has been
reviewed by Guenther (1948-1952). Several
bitter principles have been isolated from
lemon seeds and these will be further dis-
cussed in the section on lemon flavor.
Lemon juice is used as the basis for soft
drinks and in food processing. The natural
juice may be canned or frozen. Excess pro-
duction is used as a source of citric acid.
Lime
Limes are the small round-oval, yellow
to yellowish-green, thin-skinned fruits of
Citrus aurantifolia Swingle. The juice is very
acidic but has a pleasant aromatic character,
which makes it suitable for the produc-
tion of a refreshing beverage. Limes are
cultivated in Italy, Mexico, the West Indies
(Jamaica) and Florida, but are also found in
many tropical regions of the Orient.
Mandarin
[See Tangerine]
Orange
The fruit of Citrus sinensis Osbeck is the
popular sweet orange, whereas the bitter
orange, grown mainly in Spain, is from C.
aurantium L. The sweet orange is roughly
spherical, 2-4 in. in diameter and charac-
teristically orange-colored. The thick skin is
smooth, but slightly pitted due to the oil
cells just below the surface. Seeds may or
may not be present. Oranges are picked
before they are fully ripe. The maturity
is determined by the ratio of total soluble
solids, mainly sugars, to the acid content of
the expressed juice (referred to as the Brix
Acid Ratio). Certain oranges remain green
when ripe; some have an orange color while
still immature. There seems to be no rela-
tionship between the color, flavor and
maturity of citrus fruits.
222 Source Book of Flavors
Sweet oranges are a commercial crop
in the United States (California, Florida
and Texas), Italy, Spain, Portugal, Israel,
South Africa, the Azores, West Indies and
Australia. California oranges are avail-
able throughout the year, whereas Florida
oranges are best between October and June.
Numerous varieties of sweet orange are
cultivated; the principal ones are Valencia,
Parson Brown, Hamlin, Pineapple, Jaffa,
Len Gin Gong and Seedlings. Valencia
oranges (a late-fruiting variety grown on
lemon rootstock) are considered to have
the most acceptable balance of acidity,
sweetness and aromatic quality.
Tangerine
Tangerines (Mandarins or Satsumas) are the
small fruit of Citrus reticulata Blanco, (C.
mandarensis Loureiro) with a dry loose skin
and readily parted segments. Tangerines are
cultivated in the United States (California,
Florida and Texas), Guinea, West Africa,
Italy and Brazil.
Citrus Products
Citrus Fruit Juices
The juices of lemon, grapefruit, lime and
bergamot have a yellowish-green color,
while orange and tangerine juice are deep
orange in color. The characteristic aroma
and flavor of freshly expressed juice is due
mainly to aromatic constituents of the juice
but also, in part, to minute droplets of skin
oil that inevitably are present. The com-
position of the aromatics in the juice and in
the essential oil is different; this will be
discussed in a later section on citrus flavors.
The aromatic profile of citrus juices changes
considerably shortly after the juice is
expressed.
The production of citrus juices has been
described by Nagy, Shaw and Veldhuis
(1977), Heath (1978), and Ting and Rouseff
(1986).
Citrus Oils
The readily recognizable aroma of the
several species of Citrus is due to the
presence of essential oil contained in
numerous oval balloon-shaped oil sacs or
glands situated irregularly and at various
depths below the surface or cuticle of
the peel (the flavedo). A summary of the
characteristics of these essential oils follows.
These essential oils are obtained by
mechanical expression from the peel of the
fresh fruit. The precise machinery and pro-
cessing techniques used differ considerably,
not only between the various fruits handled
but also between the main growing regions.
Even with high pressures, some of the
essential oil is not recovered and only dis-
tillation of the finely disintegrated fruit peel
will give the total yield. Citrus oils are
adversely affected by high temperatures and
the flavor quality of the distilled oil is far
inferior to that of oils obtained by cold
expression. With the exception of lime oil,
every effort is made to separate the citrus
. juice and oil during recovery. Inevitably,
not only oil but other proteinaceous,
cellulosic and pectinous debris are expelled
along with the oil during mechanical press-
ing. This results in an emulsion that is very
difficult to separate and requires centrifuga-
tion to achieve a viable recovery of the
emulsified oil. The problem has largely
been overcome under automatic pro-
cessing conditions. Although somewhat
dated, the methods and plant described by
Guenther (1948-1952) are still generally
used, although specific machinery may have
been updated. Techniques used for the
recovery of volatile oils from citrus are
summarized below:
Manufacturing
Sponge Pressing The separated half
peels are hand-pressed, the extruded oil
being collected in sponges. This laborious
method gives a high-quality oil, but has
been largely discontinued.
Machine Pressing Two main types of
machine are used. Sfumatrici: automatic
pressing of the separated peels after removal
of juice and pulp; they can handle about 11/2
metric tons per hour. Pellatrici: Machines
 Natural Flavoring Materials 223

are designed to handle the whole fruit with Characteristics of Citrus Peel Oils
the oil being released by rotary rasping of (EOA 1976; Guenther 1948-1952)
the surface. Large machines can handle 2
metric tons per hour. The separated oil Grapefruit
emulsion is continuously removed from the Yield: 1.3 to 1.8lb. per ton
machines by a controlled recycling water Source: Florida, Hawaii, Texas
spray; the coarse separated liquors are Sp. Gr. 25°/25°C: 0.848 to 0.860
allowed to stand to achieve some prime Opt rotation at 20°C: +91° to +96°
separation of clear oil; the remaining RI at 20°C: 1.4745 to 1.4780
emulsion is centrifuged to give a further Evaporation residue: 5 to 10%
yield and the final intractable fraction is Aldehyde content (as decyl aldehyde) 1.4
distilled to give a lower grade of oil. to 1.6%
Combined Juice/Oil Presses Machinery
developed in the United States citrus Lemon-Cold pressed
regions is designed for the automatic extrac- Yield: 6 to 7lb. per ton.
tion of juice and oil as a single operation Source: Italy, California, Arizona
without any admixture of the products. Sp. Gr. 25°/25°C: 0.846 to 0.855
Several systems have been developed, Opt rotation at 20°C: +57° to +78°
including: (1) The fruit is halved, the juice RI at 20°C: 1.4730 to 1.4755
reamed out and the cleaned peels subjected Evaporation residue: 1.5 to 2.2%
to pressure between fluted rollers. (2) The Aldehyde content (as citra!): 1.7 to 5%
surface of the whole fruit is first grated, the
oil being removed by jets of water; at the Lemon-Distilled
same time, a hollow pipe is inserted into the Yield: 14lb. per ton
base of the fruit and the juice extracted by Source: California
pressure. Sp. Gr. 25°/25°C: 0.842 to 0.856
Distillation of Lime Oil In spite of the Opt rotation at 20°C: + 55° to + 75°
considerable lowering of quality, lime oil RI at 20°C: 1.470 to 1.475
has traditionally been produced as a by- Aldehyde content (as citra!): 1 to 3.5%
product of lime juice processing. The oil is
recovered by distillation of the acid liquors Lime-~xpressed
obtained by crushing the whole fruit. The Yield: 7lb. per ton
flavor of this oil is distinctly different from Source: West Indies, Mexico
that of cold-pressed oil (Azzouz, Reineccius Sp. Gr. 25°/25°C: 0.872 to 0.881
and Moshonas 1976). Opt rotation at 20°C: +35° to +41°
Citrus oils are characterized by having RI at 20°C: 1.4820 to 1.4860
a very high percentage of terpenes and Evaporation residue: 10 to 14.5%
relatively low percentages of aromatic Aldehyde content (as citral): 4 to 8%
oxygenated compounds. The chemical com-
position of citrus oils will be discussed in Lime-Distilled
a later section dealing with the individual Yield: 4 to 7lb. per ton
citrus flavors. The aromatic characteristics Source: West Indies
of citrus oils have been described by Heath Sp. Gr. 25°/25°C: 0.855 to 0.963
(1978) and physico-chemical standards Opt rotation at 20°C: +34° to +47°
are published in EOA Specifications and RI at 20°C: 1.4745 to 1.4770
Standards. Aldehyde content (as citra!) 0.5 to 2.5%
The essential oils obtained by distillation
of the leaves and flowers of citrus plants are Orange-Bitter
discussed in the section on essential oils. Source: Sicily, Spain, West Indies, Russia
224 Source Book of Flavors
Sp. Gr. 25°/25°C: 0.845 to 0.851
Opt rotation at 20°C: +88° to +98°
RI at 20°C: 1.743 to 1.475
Evaporation residue: 2.5 to 5%
Aldehyde content (as decyl aldehyde) 0.3
to 1%
Orange-Sweet, cold pressed
Yield: 1.5 to 3lb. per ton
Source: Brazil, California, Florida, Italy resulting oil is designated "terpene-free" or,
Sp. Gr. 25°/25°C: 0.842 to 0.853
Opt rotation at 20°C: +94° to +99°
RI at 20oC: 1.4723 to 1.4750
Evaporation residue: 2 to 5.5%
Aldehyde content (as decyl aldehyde): 0.5 are removed as well as the terpenes, then
to 2.7%
Orange-Sweet, distilled
Source: California
Sp. Gr. 25°/25°C: 0.840 to 0.844
Opt rotation at 20°C: +94° to +99°
RI at 20°C: 1.471 to 1.4~4
Aldehyde content (as decyl aldehyde): 1 due to their presence that the essential oils
to 2.5%
Tangerine (Mandarin)
Yield: 4 to Sib. per ton
Source: Florida, Brazil, Italy
Sp. Gr. 25°/25°C: 0.844 to 0.854
(Italy: 0.847 to 0.853)
Opt rotation at 20°C: +88° to +96°
(Italy: +63° to + 78°)
RI at 20°C: 1.4731 to 1.4752
(Italy: 1.4730 to 1.4770)
Evaporation residue: 2.3 to 5.8%
(Italy: 2 to 5%)
TABLE 7-18. Composition of citrus oils (Heath, 1981)
Oil
Lemon
Sweet orange
Bitter orange
Lime (distilled)
Tangerine (Mandarin)
Grapefruit
Aldehyde content (as decyl aldehyde) 0.8
to 1.9%
(Italy: 0.4 to 1.8%)
Terpeneless and Concentrated Citrus Oils
Citrus oils are characterized by a high
percentage of terpene hydrocarbons (Table
7-18). lfthe monoterpenes are removed, the
more usually, "terpene less." However, it
still contains the sesquiterpenes as well as
any oxygenated aromatic components. If,
by further processing, the sesquiterpenes
the oil is said to be "sesquiterpeneless." In
many cases, the sesquiterpene content of
the oil is relatively low so that the two terms
have come to be used synonymously.
The outstanding characteristic of the
terpene hydrocarbons is their comparative
insolubility in diluted alcohol, and it is
themselves are but poorly soluble in this
solvent. These compounds oxidize readily
and tend to resinify with a deterioration of
odor and flavor. On standing, the degree of
resinification leads to a thickening of the oil
and a considerable reduction in its solubility.
The terpenes possess little intrinsic flavor
value although it is probably not true to
say that they have no flavoring effect. The
profile of deterpenated citrus oils is sig-
nificantly flatter and lacks the characteristic
freshness associated with the complete oil
(Heath 1978).
Principal
Terpenes (%) Compounds Oxygenated (%)
About 90 Citral1.7-5.0
About 90 n-Decylic aldehyde 0.9-3
90-92 n-Decylic aldehyde 0.8-1
Linalyl acetate 2-2.5
75-80 n-Decylic aldehyde 1-5
95-96 Methyi-N-methyl anthranilate 1
About 90 n-Decylic aldehyde 1-2

Terpeneless citrus oils are of particular
value where solubility and long shelf life are
required in an end product. The removal of
the terpenes inevitably results in a con-
centration of the remaining oxygenated
flavoring constituents, and the commercial
claims for the degree of concentration may
be misleading, depending on the basis of
assessment.
The concentration of a terpeneless oil
may be calculated in several different ways.
The most common method is to state con-
centration in terms of the reduction in
volume that the oil undergoes. For example,
if the original oil is reduced in volume by a
factor of five, it it a five-fold oil. Obviously,
the fold does not correspond to flavor
strength (i.e., a five-fold oil is not neces-
sarily five times stronger than a single-fold
oil), but only the degree of volume reduc-
tion. The level of concentration may also be
calculated from the ratio of the principal
constituent in the concentrated oil to that of
the prime oil from which it was made. For
example, with terpeneless lemon oil, the
citral content of a concentrated oil may be
quoted as 40-45 percent, while that of the
natural oil varies between 4-4.5 percent.
This would indicate a ten-fold concentration
that is not borne out in practice, the effec-
tive flavoring power being much higher than
this. The practice of selecting just one com-
ponent fails to take into account the other
components that may significantly affect the
flavor quality and strength-components
that may have a far greater contribution to
the overall profile than that of the selected
compound. The actual yield of terpeneless
or concentrated oil obtained from a known
weight of whole oil is the best basis for
stating the degree of concentration achieved.
Comparative evaluation in an end product is
probably the only really satisfactory way of
establishing the actual concentration and,
hence, the relative commercial value of the
product. Specifications for terpeneless and
concentrated citrus oils should be procured
from the manufacturer.
Natural Flavoring Materials 225
Cranberry
The American cranberry, which is the fruit
of Vaccinium macrocarpon A it., resembles a
small cherry in appearance, the berries
being red throughout. The European
variety (V. oxycoccus L.) is an even smaller
fruit. The fruit is fleshy and firm, and
matures late in the fall. It is extremely
acid and thus is not commonly eaten raw.
The principal varieties are Early Black,
McFarlin and Howes. Cranberries are
cultivated in Massachusetts, New Jersey,
and the Pacific Northwest. Cranberries con-
tain citric acid, benzoic acid, quinic acid and
pectin, and have little characteristic volatile
flavor.
Cranberry juice is prepared by heating
the fruit with water. The heat softens the
berries, the fruit is then comminuted and
the juice is centrifuged or pressed out.
A yield of about 100 gal. of red juice is
obtained from 1,250 lb. of cranberries.
The presence of pectins in cranberry juice
causes the extractive matter and soluble
solids present to gel. Pectinol is added to
the expressed juice to dissolve the pectins.
Cranberries are seldom used in flavors, but
are popular for the preparation of sauces,
jelly and juice (Aurand 1989).
Currant
Currants are classified into three species
based largely on color:
White and red currant-Ribes satiuum
Syme
European black currant-R. nigrum L.
American black currant-R. americnna
Mill.
Currants grow in clusters or "strings"
bearing a variable number of berries. The
fruit in the cluster ripens at different times,
the berry farthest from stem being the ripest.
Normally, whole clusters are picked and
not the individual berries, so that the degree
of ripeness in any gathering will be variable.
226 Source Book of Flavors
White currants differ from red in color
and they generally lack flavor. Red currants
have a pleasant aroma, an agreeable level of
acidity and are popular as a dessert fruit.
Black currants, freshly harvested, do not
have a pleasant odor or flavor, but after a
slight fermentation the aroma modifies and
the flavor assumes a richly pleasing and
quite characteristic profile, which is very
popular in the United Kingdom and Europe
but much less so in North America.
Currants are used in the production of
jam, jelly and juice, the latter being com-
mercially prepared in the United Kingdom
by a cold pectic enzyme method as a basis
for a hot or cold beverage.
Damson
See Plum
Date
Dates are the sticky elongated berries of
Phoenix dactylifera L., a palm that grows
throughout North Africa, Iran, Iraq and
many other dry semitropical regions. The
variety that grows in California is the Deglet
Noir, a semisoft fruit with a nonsticky skin.
The fruits are light brown in color, but
darken on storage. The commercial product
is dehydrated, usually at a low temperature,
to retain maximum flavor quality.
Dates contain a high percentage of
sugar either as invert or as sucrose, whose
level is maximum just before ripening. They
retain their quality best if stored between
-zooc and -10°C (0° to 10°F). Normally,
moisture-proof packages are used to min-
imize deterioration during storage at room
temperatures.
Fig
Figs are among the oldest fruits known to
man. The fig is a pear-shaped fruit of Ficus
carica L., and what one calls the fruit is in
fact the swollen receptacle whose inner wall
is lined with numerous minute seeds-the
true fruit. Figs show considerable varia-
tion in size, color and form, but all are
green when unripe and may be white, brown
or purplish-colored when ripe. The trees
normally produce two crops a year, in very
early and late summer; in some regions a
third crop is possible. The trees live and
fruit for upward of 50 years.
Figs are cultivated in most Mediterranean
countries and the Middle East, the following
varieties being recognized: Adriatic, Black
Mission, Calimyrna and Kadota. Figs are a
dessert fruit, but may be canned or dried for
use in certain baked goods. An aqueous
extract of figs with added sugar (syrup of
figs) is used medicinally as a mild laxative.
Gooseberry
There are two main varieties of gooseberry:
American gooseberry Ribes hirtellum Michx.
-a reddish spherical berry, smooth-
skinned, 1-2 em. in diameter.
European gooseberry Ribes grossularia L.-
a larger, greenish-yellow fruit with a
hairy skin. Another species, R. uva-
crispa, is also recognized.
Gooseberries are used mainly for making
jam and in pie fillings. They are available
commercially as fresh fruit, canned or
frozen.
Grape
Grapes thrive in the middle belt of the tem-
perate zones. In the northern hemisphere,
there is extensive viticulture in France,
Italy, Switzerland, Greece, Spain and the
United States. In the southern hemisphere,
South Africa, Australia, New Zealand and
South America all have well-established
wine producing industries. Grapes grow in
bunches on the vines, the fruit ranging from
greenish-yellow through deep ruby red to
black in color, depending on the species and
variety.
Grape Types
Grapes are classified into two major groups
having a significant flavor difference:

American Grape
Vitus labrusca L.-the wild grape.
V. Iabruscana Bailey-grown in eastern
and central north-eastern regions of North
America.
V. rotundifolia L.-the Muscadine
grape, grown in south-eastern regions where
conditions are hot or humid.
European Grape
Vitus uinifera L.-the European wine
grape, having a longer berry and a thinner
skin than the American species. This grape
is also suitable for dessert use. It is grown
throughout Europe and in the wine regions
of South Africa and Australia.
The grape varieties suitable in the manu-
facture of flavors are: Concord, a blue-black
and round grape, which is pleasing in flavor
when fully ripe. Worden, a black grape,
whose skin is sweet and whose center is tart.
Catawba, a red grape of very good flavor.
Delaware, also a red grape with a sweet
flavor. Muscat of Alexandria, a white, large
grape with a thick tough skin, having a
pleasing flavor, and used chiefly for raisins.
Sultana, also a white grape but seedless. It is
also used for raisins.
Guava
The fruit of the tropical tree Psidium
guajaua L., is known throughout every
tropical region worldwide. The following
varieties are valued for their pleasing sugar/
acid/pectin balance: Costa Rica, Chamach
and Feijoa. The esteemed Strawberry
guava is derived from another species, P.
cattleianum L.
Guava juice is very acidic and is too tart
and strongly flavored for direct use, but is
suitable for dilution with a sugar syrup
to make a carbonated beverage. Guava is
eaten as a dessert, but the numerous minute
seeds give it an unpleasant "sandy" texture.
The fruit is used to make jam and jelly as
well as for blending with other tropical fruits
to make a punch base.
Natural Flavoring Materials 227
Huckleberry
The common black huckleberry is the
fruit of Gaylussacia baccata Koch. It is
not really a berry, but a ten-celled drupe.
Huckleberries grow abundantly in the
northeastern United States and eastern
provinces of Canada. The fruit is used in
pies and in some baked goods. It is available
commercially as fresh, dried, frozen or
canned.
Kiwi Fruit
Kiwi fruit is a brown, ovoid, hairy fruit
(Actinida chinensis) cultivated and exported
from New Zealand. The inner flesh is pale
green with several lines of embedded dark
brown seeds that are soft and edible. The
flavor of the fruit is sweetly aromatic, some-
what reminiscent of a blend of melon and
gooseberry.
Mango
Mangoes are the fruits of the large tropical
evergreen tree, Mangifera indica L., and
are the most popular fruit throughout the
Orient. Mango grows extensively in India
and increasingly in Southeast Asia, Hawaii,
most Pacific islands, Australia, West Indies
and in many parts of the African continent.
The leathery-skinned fruit is roughly ovoid
but laterally compressed, and varies con-
siderably in size, shape, color and flavor.
The fleshy edible pulp is yellow, very juicy
and has a distinctive aromatic profile, which
will be discussed in a later section.
Indian mangoes (varieties are Badami,
Raspuri and Neelam) generally contain
more sugar than those grown in Florida
(where the varieties are Haden, Irwin, Zill,
Kent and Keit). The sugar/acid balance
changes during ripening, although this is
not a good criterion of ripeness or quality
(Hulme 1971).
The fruit is widely eaten raw and is also
made into chutney, jelly and conserves.
228 Source Book of Flavors
Melon
Melons are mostly eaten as mature dessert
fruits, although other members of the botan-
ical family Cucurbitaceae are non-dessert
fruits (e.g., cucumber, gherkin, squash
and pumpkin). From a flavor point of view,
there are two types of melons which have
many varieties and cultivars: muskmelon
( Cucumis melo L. )-canteloupe, honey-
dew; and watermelon ( Citrullus lanatus
(Thunb.) Mansf.) Melons display a wide
range of appearance, size and shape, having
an external skin which may be smooth,
ridged or reticulate. The edible flesh ranges
from a compact solid texture with a cen-
tral cavity containing numerous seeds
(canteloupe) to a more open cellular
structure containing embedded seeds
(watermelon). The flavor of these two
groups is distinctly different and changes
significantly during the ripening process.
Olive
The olive tree (Olea europaea L.) is
indigenously widespread throughout the
Mediterranean region and has become
established in California, Australia and
South Africa where the climate is suitable.
The olive is a fleshy drupe having a soft
flesh surrounding a hard stone or pit. It is
roughly oblong, with a green skin when
unripe changing to purple or black when
fully ripe. The pulp of the unripe fruit is
very bitter due to a glucoside, oleuropein,
but mellows as the fruit ripens. The pulp is
characterized by a high oil content (6-25
percent), depending on the variety and
harvest season.
Olives are most popularly consumed
as pickled green olives either natural or
depitted and stuffed with a savory filling.
In the "Spanish type" the bitterness is
removed from the unripe fruit by treatment
with a diluted lye solution (1.5-2.5 percent
sodium hydroxide) followed by a water
wash before pickling in a brine (9° to 11 o
Baume). During the period in the brine the
heated olives undergo a lactic fermentation.
The pickled olives are finally sorted and
packed into containers. The "California
style" product uses olives which are much
riper, otherwise a poor-flavored product
results. In the case of black olives, an oxida-
tion stage is necessary after the initial lye
treatment to oxidize the phenolic pigments
present. Californian olives are normally
packed in cans in a 3 percent sodium chloride
solution.
The processing of olives for the recovery
of olive oil has been described by Martinez-
Suarez and Mendoza (1986), who quote
numerous references to the extensive litera-
ture on this widely used edible oil.
Papaya
Papaya is the succulent fruit of the large
tropical palm-like plant Carica papaya L.
This branchless plant is crowned by deeply
lobed leaves and bears on the upper part of
the stem numerous fruits, which are melon-
like and may range from 3 to 20 in. in
length. The very juicy flesh is deep yellow to
orange-colored. The hard black spherical
seeds are present in a central cavity.
Papaya has a sweet taste and an agree-
able flavor, which is not very pronounced.
The unripe fruit has a white milky juice
that contains the enzyme papain. This is
collected commercially and purified for use
as a meat tenderizer.
Passion Fruit
There are several hundred species of the
genus Passiflora, the large berries of some
species being edible. In the United States,
Passion flower grows extensively from
Virginia to Florida and in Texas. The prin-
cipal species is Passiflora incarnata L., the
very distinctive flowers of which give way
to a greenish-yellow highly aromatic fruit
about 2 to 8 in. in diameter. Some species
are known as granadillas, whose fruit are
generally very large and may weigh up
to Sib. These include: giant granadilla

(P. quadrangulais); purple granadilla (P.
edulis); yellow granadilla (P. laurifolia).
Another species, P. maliformis, is the sweet
calabash of the West Indies. The fruit has a
brittle rind and numerous flat seeds in a
gelatinous edible pulp that is slightly acidic.
Peach
Peaches are the delectable fruits of Prunus
persica Batsch, which grows widely in
the United States (California, Georgia,
Maryland, New Jersey, Washington,
Massachusetts, New York and Florida),
Spain, France, Italy, Argentina, Australia,
Chile, New Zealand and South Africa.
The fruit is spherical, 1-3 in. in diameter,
with a hairy skin and a marked groove on
one side. The fleshy pulp surrounds a hard,
deeply pitted stone whose kernel contains
about 40 percent of fixed oil. There are two
classes of peaches: clingstone and freestone,
depending on whether the pulp adheres to
the pit or may be separated freely. They are
further classed as white or yellow, depend-
ing on the color of the flesh. There are
numerous commercial named varieties,
among which Elberta freestone has the out-
standing flavor. Nectarines (var. nectarina
Maxm.) are smooth-skinned peaches.
The ripe fruit is hand picked for use
as a dessert, but may be canned, frozen or
made into preserves. Fresh peaches may
be skinned and deep frozen, but undergo
very rapid browning due to the presence of
oxidizable tannins and oxidase enzymes.
There has been some very good flavor work
on peach demonstrating the detrimental
effect of picking the fruit immature. (Morton
and MacLeod 1990).
Dried Peaches
Only ripe fruit is used for drying. Dried
peaches darken in color rapidly on storage
in a warm place having a low humidity.
Peach fruit color is often prepared by simple
alcoholic extraction of dried peaches whose
flavor has deteriorated and color darkened
by high temperature storage.
Natural Flavoring Materials 229
Pear
The common pear (Pyrus communis L.)
probably originated in eastern Asia, but
has been known for centuries throughout
Europe and has long been established in
North America. The varieties under cultiva-
tion run into thousands; some are regional,
others are widespread, and all differ widely
in size, shape, color, texture, consistency
and particularly in aroma and flavor. These
latter attributes depend to a large extent
on the variety and state of ripeness. The
following are the principal varieties of
commercial value: Bartlett, William, Butter
Hardy, Cornice, Kaiser, Abate, Butter
Morettini and Conference.
Pears are a popular sweet dessert fruit,
both from their appealing flavor and nutri-
tional value. A considerable part of the
commercial crop is used for canning, usually
in a light sugar syrup, or for the making of
preserves, jelly, candied fruit and puree. A
small proportion is dried.
Pear Puree
Large quantities of sound pears having
a desirable flavor but not of a sufficient
quality for canning are processed into pear
nectar, puree or concentrate. Most com-
mercial operations make little attempt
to recover the finer aromatic fractions,
which are largely lost in conventional open
evaporation systems.
Pineapple
The pineapple (Ananas cosomus Merr.) is a
large fruit composed of many six-sided
berries arranged spirally and embedded in
the juicy pulp of the swollen stem. The so-
called fruit carries a crown of spiny leaves
and may grow to a weight of 6kg. (14lb.).
The plant is a native of Brazil and its early
Spanish name "pina" was given because
the fruit resembles a pine cone. The plants
bear one fruit, which may take up to two
years to mature. It is cultivated throughout
the tropical regions of the world with
230 Source Book of Flavors
major commercial plantations in Hawaii,
the Phillipines, Taiwan, Malaysia, South
Africa and Australia, with other centers in
Florida, Puerto Rico and East Africa.
The fruit contains citric and malic acids
and a relatively low level of sugars, whose
percentage rapidly increases as the fruit
ripens. The largest part of the flavor is
derived from the outer tissues or peel,
although some flavor is distributed in the
pulp. The flavor profile varies considerably
with the season, the summer crop being
sweeter and more aromatic than the winter
crop.
Pineapple is used extensively as a dessert
fruit, but considerable quantities are pre-
pared in various forms for canning and are
juiced. The production of pineapple juice is
described by Mehrlich (1971).
Plum
There are several species of plum that are
interesting as a source of flavor:
European Plum: Prunus domestica L. is
a roughly spherical fruit, about 11/2 in. in
diameter with a smooth thin skin that
readily peels.
Damson: P. domestica L., var institia
Baily is a fruit about %in. in diameter,
having a blue-black skin.
Greengage: P. domestica L., var italica
Schneid. is a much larger fruit with a
yellowish-green skin.
Japanese Plum: P. salicina L. is a spher-
ical ovoid fruit with a pointed apex 2-3 in.
long in total. It is yellow, light red, or pale
green in color.
There are many varieties of plum, the
color of the fruit varying from red through
yellow, and from green to blue/black. The
pulpy flesh of ripe plums is firm but sweetly
juicy. The main flavor is carried in a waxy
material present on the surface of the skin.
Certain species of plum are particularly
satisfactory for drying; these are marketed
as prunes and provide a good source of an
acceptable flavor.
Pomegranate
The pomegranate is the roughly spherical
red fruit of Punica granatum L. It has a thin
but tough rind packed with angular seeds
surrounded by a juicy pulpy mass. The ripe
fruit yields a red juice, which is sweet and
has a rich pleasing but overly acidic flavor.
Care must be taken in juice processing to
avoid the inclusion of tannins derived from
the rind and "rag." The edible portion
must be removed without undue contact
with the husk and the juice expressed from
the halved or quartered fruit.
Pomegranate fruit flavor is used in the
preparation of grenadine syrup for cocktails
and other mixed drinks.
Raisin
About 85 percent of the grapes dried are
of the Thompson Seedless variety, also
known as the Sultanina; the seeded variety
being known as the Muscat. The grapes are
harvested when the juice has attained a Brix
reading of between 24° and 25° at which
time the grapes are dried.
Bleached raisins are prepared by dipping
in a warm alkaline solution to check the
skins. They are then rinsed and dried on
trays in the sun. Raisins are also bleached
with sulfur dioxide. Four pounds of fresh
grapes are required to yield one pound of
raisins.
Raisin Oil
Raisin oil is obtained from the seeds of
Muscat grapes, which are removed before
drying the grapes for raisins. The oil is used
primarily for coating raisins to prevent them
from sticking together. The treatment with
oil renders the raisins soft and pliable for
a longer period of time, makes them less
subject to insect infestation and improves
their appearance.
Raspberry
There are two groups of raspberry: red or
yellow raspberry-Rubus idaeus L. or R.

strigosus Michx.; and black raspberry-R.
occidentalis L. The purple raspberry is
a hybrid of these species although some
authorities quote it as a separate species,
R. neglectus. The fruit is an aggregate
of drupelets firmly held together on the
receptacle from which they separate when
the fruit is ripe and harvested. Raspberries
grow in several northern regions of the
United States (New York, Ohio, Michigan,
Oregon and Washington) and throughout
Europe. Ripe raspberries for processing as a
source of flavor should be handled quickly
after picking as softening develops rapidly
with loss of flavor quality. The fruit should
be picked and cleaned to ensure the absence
of leaves, stems, receptacle parts, etc., all of
which may give rise to unpleasant off-notes.
Raspberries are consumed as dessert fruits
and are available commercially in canned
and frozen packs as well as in the form of
jam or jelly. The fresh flavor undergoes
considerable modification on heating; this
topic will be discussed in a later section
dealing with raspberry flavors.
Sloe
Sloe or blackthorn is a spiny shrub
(Prunus spinosa L.) native to Europe and
now cultivated in the United Kingdom.
Another plant, Crategus uniftora (or
C. tomentosa), is often given the same
name. In the United States, the black haw
(Vibernum prunifolium) is also known
as sloe. The genuine fruit is bluish-black,
about 2 em. in diameter, with a bloomed
skin. It has an acidic pulp that is used in the
flavoring of sloe gin.
Strawberry
The true fruits of the strawberry, derived
from several species of the genus Fragaria,
are the numerous small achenes embedded
in the reddish surface of the swollen fleshy
receptacle which is generally regarded
as the fruit. There are at least eight recog-
nized species of strawberry. The so-called
Natural Flavoring Materials 231
wild strawberry (Fragaria vesca L. and F.
semperflorens L.), which grows in wooded
and mountainous areas in Europe and
North America, has smaller, darker-colored
fruits with a more pronounced aroma than
the fleshy cultivated varieties that are grown
more for their appearance and size than for
their flavor. The main varieties are F. elatior
and F. collina (Europe); F. virginiana
(North America); F. chiloensis-Duchene
(Chile, Mexico, United States). The
numerous varieties of strawberry grown
commercially in the United States are dis-
cussed by Wolford (1974).
Several varieties of strawberries are cul-
tivated in Georgia, Tennessee, Maryland,
Virginia, Florida, Louisiana, California and
the northwestern states, and are grown for
different uses; some are used for preserving
and freezing, others for flavor, and still
others for color. California now grows
approximately one-half of the United States
production.
Strawberries deteriorate quickly due
to local bruising and the rapid growth of
surface molds. Juice designated for use in
flavorings should be mixed immediately
with alcohol to above 18 percent ethanol
content. The addition of sugar at a ratio of 3
to 1 or 4 to 1 to freshly picked strawberries
assists in preserving the flavor.
In the production of flavor, partially
defrosted or fresh strawberries are quickly
ground and their seeds slighly sheared to
yield a pronounced strawberry flavoring
extract. The fruit is mixed with alcohol
either before or immediately after grinding.
The distillation at atmospheric pressure
of pressed strawberry residue yields a very
fine flavor in the first fraction at an alcohol
content of 65 to 80 percent.
Strawberry fruit flavors that are con-
centrated by the freezing method com-
pletely hold the freshness of volatile aroma
and the brilliance of color. The finished
flavor should be kept in cool (not cold)
storage.
The berries are picked in the early morn-
ing when the fruit is cool, the stems usually
232 Source Book of Flavors
being pinched off in picking. The fruit is
then rapidly washed to rid the berries of
sand and reduce the risk of mold growth
and fermentation. The color and flavor of
strawberries remain fresh when they are
kept frozen or cold packed.
The Corvallis, Marshall, Clark Seedling,
Redheart and Ettersberg strawberries are
used for freezing. The flavor and ice cream
industries use the Marshall, Blakemore and
Klondike varieties, which have a high flavor
and deep red color.
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Sheu, M.J. 1987. Applications of ultrafiltration
and reverse osmosis for apple juice clarifica-
tion and concentration. Dissertation Abstracts
international 47(8):3185-3186: Order No.
DA8625735.
Sinclair, W.B. 1984. The Biochemistry and
Physiology of the Lemon and other Citrus
Fruit. Oakland: Univ. of California.
Sole, P. 1989. Banana processing. United States
Patent. 4 874 617.
Takeoka, G.R., Guentert, M., Flath, R.A.,
Wurz, R.E., and Jennings, W. 1986. Volatile
constituents of kiwi fruit (Actinidia chinensis
Planch. ). J. Agric. Food Chern. 34(3):
576-578.
Tateo, F. 1990. Production of concentrated
orange oils using a thin film evaporator. J.
Essent. Oil Res. 2(1):7-13.
Temelli, F., Chen, C.S., and Braddock, R.J.
1988. Supercritical fluid extraction in citrus oil
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Ting, S.V. and Rouseff, R.L. 1986. Citrus Fruits
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Williams, A.A. 1983. The flavour of non-citrus
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HERBS AND SPICES
It is a little difficult to appreciate that at one
time the economy of whole communities
was based on the trade in spices, the use of
which is almost as old as man himself. Upon
this trade was built the wealth of such cities
as Venice and Alexandria and, with the
opening up of the sea routes under the
restless exploration of the Portuguese,
the prosperity of these trading communities
became doomed. Throughout history, the
country that controlled the spice trade
was the richest and most powerful in the
world. In the 19th century, Great Britain's
maritime prowess established her as the
leader of this lucrative trade, but dominance
in this trading activity has changed hands,
and the United States is now the prime
figure in world spice buying, with New York
as its center. With the vast increase in trade
in other food commodities, raw materials,
manufactured goods and services, the
relative importance of spices has declined
and now represents something less than 0.1
percent of the total world trade. Although
minute, this does not mean that the spice
trade is no longer of importance or interest.
The interests of companies engaged in
handling spices are actively represented by
the American Spice Trade Association, 580
Sylvan Ave., Englewood Cliffs, N.J. This
Association provides up-to-date informa-
tion on importations, market trends, etc.,
for its members, as well as producing
articles on herbs and spices of general
TABLE 7-19. Unites States: Imports of specified condiments, seasonings, and flavoring materials, 1989-1990

Item 1989 1990

Metric tons 1,000 dollars Metric tons 1,000 dollars

Allspice (Pimento) 1,128.2 1,827.3 1,012.1 1,700.5

Anise 1,105.9 1,177.0 984.3 1,589.0
Basil 1,991.6 2,469.9 1,831.5 2,657.4
Capers 1,246.3 7,856,6 1,384.6 7,641.9
Capsicum or red peppers:
Anaheim & ancho 1,263.3 2,373.5 1,501.8 3,096.1
Other 13,215.9 28,211.6 11,692.6 20,660.5
Ground 4,192.0 4,053.5 6,760.0 5,066.9
Paprika 4,196.8 7,494.1 4,117.8 7,539.0
Caraway 3,446.0 2,507.2 3,084.2 2,162.2
Cardamom 163.6 544.9 220.1 1,081.7
Cassia & Cinnamon 14,414.0 36,395.6 10,921.1 22,253.3
(ground) 382.4 893.5 715.0 1,460.7
Celery seed 2,901.3 2,210.8 2,202.7 1,630.5
Cloves 1,134.4 2,328.5 1,850.8 3,645.0
Coriander 2,417.8 1,229.9 2,160.6 1,070.0
Cumin 4,707.2 4,539.3 4,670.6 4,672.3
Curry & curry powder 476.1 1,442.8 428.4 1,279.6
Dill 614.6 529.3 592.9 513.0
Fennel 2,809.9 2,964.1 2,903.0 3,769.1
Garlic (dehydrated) 3,195.8 3,917.0 6,272.0 8,582.6
Ginger (including fresh) 4,955.5 5,146.1 5,793.9 6,569.5
(ground) 470.0 424.5 1,356.7 1,576.1
(sweet) 187.3 370.6 214.3 512.4
(candied) 252.3 701.8 220.2 764.5
Laurel (Bay) leaves, Thyme 1,656.3 3,006.8 1,465.3 2,987.2
(other than crude)" 44.8 54.5 44.3 42.9
Mace 294.0 1,862.8 295.7 1,650.2
Mint leaves 25.4 41.3 87.6 143.4
Mustard Seed 46,515.5 12,631.3 55,625.3 17,812.2
(ground) 3,736.0 3,646.5 3,721.1 3,970.7
(prepared) 3,227.5 5,580.0 3,210.1 5,926.7
Nutmegs 1,915.1 11,073.0 1,710.9 5,088.6
Onions (dehydrated) 1,371.3 1,115.0 2,534.6 3,553.1
Origanum 3,386.3 5,529.3 4,689.7 7,336.9
(other than crude) 1,019.0 1,015.5 469.8 622.7
Parsley (manufactured) 268.2 560.9 332.7 959.4
Pepper, black 31,818.8 77,261.4 32,979.6 58,609.5
(white) 5,549.0 16,914.7 5,721.1 10,381.9
(ground) 385.7 1,035.1 735.2 1,693.4
Poppy seed 4,160.3 3,718.7 3,354.8 2,953.4
Saffron 8.5 3,258.7 19.4 3,213.2
Sage 2,043.7 6,832.7 1,656.4 4.742.4
Sesame Seed 40,514.1 39,961.7 42,878.8 56,869.0
Thyme (other than crude) 70.9 123.4 31.3 89.0
Turmeric 2,147.1 1,807.2 1,691.1 1,374.5
Vanilla beans 1,107.4 46,125.3 975.2 47,757.9
Mixed spices, other 4,538.4 8,559.1 1,828.0 5,612.2
Total 226,671.5 373,924.3 238,949.2 354,954.2
Spice oleoresins:
Paprika 351.8 14,468.2 433.6 19,012.6
Black pepper 131.9 2,976.1 190.4 3,951.2
Other 455.2 5,455.9 402.5 7,299.0
Total 938.9 22,900.2 1,026.5 30,262.8
"Excluding thyme.
Source: U.S. Department of Commerce.
236 Source Book of Flavors
interest to users, methods of analysis of
spices and advice on spice standards, etc.
The membership of ASTA reaches into
more than 30 countries around the world
that send spices to the U.S. market. Every
function in the production and marketing
of spices is represented, from growers and
shippers overseas to importers, brokers,
agents, grinders, processors, domestic
growers and associated organizations in the
United States. All the activities of ASTA
are designed to promote an orderly trade
and high standards of quality for spices sold
in the United States.
There are some 36 well-recognized and
widely used herbs and spices. The bulk
of the world trade in these commodities is
concentrated in only a very few of them;
black and white pepper is by far the most
important in dollar value. Of the remaining
spices, the greatest trade is carried out
in clove, nutmeg, cardamom, cinnamon
(cassia), ginger, mace and allspice. Accurate
statistics are difficult to obtain as spices
are frequently not recorded separately in
national import/export figures. In addition,
there is not complete agreement as to
what shall be classified as a "spice." In
the United States, dehydrated vegetable
seasonings and vanilla beans are also
included in the figures. The data for imports
into the United States, published by the
Foreign Agricultural Service, USDA and
provided by ASTA, is given in Table 7-19.
Most of the spices still come from the East
as they have for centuries, but many are
now being cultivated in the United States
and in South American countries. The
United States still draws heavily on Europe
for herbs and on Africa, India and the
East Indies, and South and Central America
for spices and aromatic seeds.
The United States now supplies a
significant portion of its spice needs via
domestic production, and California is by
far the major source. If one includes the
dehydrated vegetables such as onion and
garlic powders, then California provides
more tonnage of products for America's
spice shelves than any other area of the
world. ASTA reports that California is a
major producer of dehydrated onion and
garlic as well as paprika, chili peppers and
red pepper. This state also has commercial
cultivation of basil, tarragon, dillweed,
sage, rosemary, marjoram, chervil and
savory herbs material.
According to ASTA sources, the latest
figures available show that spice consump-
tion in the United States is continuing to
increase far in excess of population growth.
In the last five years, the average annual
consumption of spices was 694,414,000
pounds as compared with 561,654,000
pounds in the previous five years. This is
nearly a 25 percent increase in consump-
tion. Consumption in 1990 was estimated
at 795,485,000 pounds-a healthy growth
from the previous year (742,485,00 pounds).
The "firepower" spices led the increase; red
pepper was up over 14 million pounds, while
black and white pepper were up another 3.3
million pounds. In the 1980's, the big gainers
were fennel seed (145 percent), capsicum
(hot) peppers (143 percent), cloves (94 per-
cent), oregano (82 percent) and basil (80
percent).
With few exceptions, spices as prime
commodities generally constitute only a
small item in the trade of the producing
country. Again, accurate figures are not
readily available as many are consumed
locally and there is a considerable entrepot
trade, which distorts actual import and
export statistics. In two countries, spices
are of vital importance to the economy:
Tanzania (Zanzibar) clove accounts for a
large proportion of the country's revenue as
this one crop supplies something like two-
thirds of the world's requirements of about
l2Vz thousand tons per annum; Granada
nutmeg and mace provide almost half of the
country's revenue. If one includes vanilla as
a spice, then this is the second largest dollar-
earner in the Malagasy Republic. It can
readily be appreciated why such countries
seek mutual aid, and why farmers are very
anxious to find alternative crops and are not

desirous of continuing the cultivation and
handling of spices at barely profitable world
market prices.
Spices, usually in the whole form as
exported, are brought into the United States
through ports on both seaboards, but by far
the largest volume comes into the port
of New York. In an excellent booklet on
"Spice Processing" ASTA describes the
several stages entailed in importing spices.
When foreign-grown spices arrive at an
American port, they must pass through
several checkpoints before release for use
or domestic sale. Inspectors of the Food
and Drug Administration (FDA) draw and
inspect samples. Members of ASTA also
have the facility to draw representative
samples of the imports and may have them
analyzed by independent laboratories for
use in the event of any claims or arbitration.
During this period, the goods are tem-
porarily warehoused by the importer who
purchased them. Shipments that fail the
FDA inspection or do not meet with govern-
ment or industrial standards must either be
cleaned further under strict FDA surveil-
lance to meet the requirements or be
shipped back to origin at the expense of the
importer. When cleared, the spice lots are
available for sale to the processor and may
be removed from the docks. Similar arrange-
ments exist in other major spice trading
centers such as London and Amsterdam.
Spice Products
Spices generally do not yield their distinc-
tive flavors if added to food in their whole
state and they must, therefore, undergo
some preliminary treatment in order to
release the aromatic components. On the
domestic scale, individual spices may be
purchased whole and then ground or com-
minuted as required; or they may be already
ground, often preblended as a seasoning,
ready for direct culinary use. Most herbs
may be used freshly gathered or, because of
seasonal availability, used in the dried form.
Natural Flavoring Materials 237
After drying, the more aromatic parts are
separated from the less flavorful woody
stems, etc., by rubbing over a coarse screen.
The broken leaves, floral parts and other
aromatic tissues are blended, graded and
are then ready for sale as such or are further
ground to a coarse powder. The flavor of
freshly ground spices is far superior to that
of the ready-ground products, as the latter
may have undergone a lengthy shelf-life
before purchase. The flavor of freshly
gathered herbs is significantly different from
that of the dried material. Commercially,
the processing of spices is undertaken by
manufacturers wholly or partly specializing
in these commodities. Very few end users
purchase and process their own spices,
and most prefer to use the following com-
mercially available types of products,
depending on their specific application:
a. Ground spices
b. Sterilized and ground products spice
c. Essential oils
d. Oleoresins
e. Dispersed spices
f. Solubilized spices
g. Encapsulated spice
h. Blended seasonings
i. Liquid spice flavorings
j. Curry powders
k. Unit-pack complete seasonings
Quality Standards
Before any processing takes place, it is
necessary to establish the quality of the
spice material. The examination and tests
carried out by government officials at the
port of entry are designed to ensure that the
lots are what they purport to be, are of at
least the minimal standard of cleanliness
and freedom from undesirable filth and
unacceptable extraneous matter, and are
safe for use in food products. These results
are not communicated to the buyer who
must himself establish the precise quality of
the raw material purchased. Heath (1968)
reviewed the evaluation of herbs and spices
under the categories given in Table 7-20.
 238 Source Book of Flavors
TABLE 7-20. Tests applied to the evaluation of herbs,
spices, and products derived from them
Whole Spices and Rubbed (Broken) Herbs
Macroscopical and sensory characters including: mor-
phology, color, odor, fracture, etc.
Freedom from molds, insect, animal and other damage.
Determination of nature and quantity of extraneous
matter and filth.
Ground Spices
Macroscopical and sensory characters.
Microscopical characters.
Determination of: sieve classification, extraneous mat-
ter and filth, crude fiber, total ash, acid-insoluble
ash, water-soluble ash, moisture content, volatile oil
content (followed by an examination of the essential
oil), alcohol or other specified solvent-soluble matter
(followed by an examination of the extractives),
nonvolatile ether or methylene chloride extractive,
cold water-soluble extractive, content of specific
components.
Sensory evaluation of odor and flavor.
Spice Essential Oils
Macroscopical and sensory characters.
Determination of: specific gravity or weight per mil-
liliter, refractive index, optical rotation, solubility in
alcohol of a specified strength, solubility character-
istics in other solvents as applicable, acid value, ester
value, saponification value, content of alcohols, al-
dehydes, esters, ketones, etc., as applicable, evapora-
tion residue (citrus oils).
Examination by: gas-liquid chromatography, thin-layer
chromatography, infrared spectrophotometry, ultra-
violet spectrophotometry.
Spice Oleoresins and Extracts
Macroscopical and sensory characters.
Determination of: volatile oil content (followed by an
examination of the essential oil), solvent residue
tests, solubility characteristics, content of specific
components, determination of special sensory char-
acteristics (color, pungency).
Dispersed Spice Products
Macroscopical and sensory characters.
Determination of: volatile oil content (followed by an
examination of the essential oil), soluble aromatic
extractives (followed by their examination), inert
base components, content of specific components,
special characters, sieve classification.
Microbiological examination (as applicable).
Note: Tests are selected to ensure a sound basis of judge-
ment of the quality and authenticity of the ma-
terial under examination. The test report should
indicate the test method used where this is neces-
sary.
Source: Heath (1968)
The specific test methods used are defined
by AOAC (1984), ASTA (1978) and ISO.
Standards for spices are not the subject of
legislation in most countries and the figures
quoted in Table 7-21 represent materials
of good average quality. Spices and spice
products purchased to specific standards
must, of course, comply in all respects
(Table 7-22). The testing of raw materials
is a costly exercise and many buyers insist
that a protocol or certificate of analysis
accompany the goods to reduce unnecessary
replication of testing.
Whole Spices
The use of whole spices in food processing
is limited as they are not a ready source
of flavor. However, they do improve the
appearance of certain products. Domes-
tically, bay leaves are often added to a
ragout or stew and cloves are inserted into
ham and baked apples. On the commercial
scale, caraway seeds are incorporated into
cakes, crackers and bread, peppercorns
are used, uncrushed, in certain European
sausages, poppy and sesame seeds are
liberally scattered over the surface of bakery
products not only to improve their appear-
ance but to give an attractive nutty flavor
and an added crunchy texture. In the
presentation of food dishes, fresh green
parsley herb is widely used as an attractive
garnish. With these few exceptions, herbs
and spices are normally milled to a powder
before use.
In handling whole spices and broken
herbs, adulteration, sophistication or sub-
stitution is not so easy, but in ground spices
and other derived products, in particular
the spice blends, substitution of materials
of different origin or even of a different
botanical entity can occur, generally when
price is considered to be of more importance
than quality or where a specific flavoring
effect is required. The principal sources of
spices and a list of their common uses are
given in Table 7-23.
Ground Spices
In natural spices the aromatic components
are retained within a protective cell wall.
This gives to the whole spice a long shelf life
so long as certain basic storage conditions
are observed. The process of grinding
partially breaks down the cellular structure,
initiates the slow release of flavoring in-
gredients and makes the spice more readily
dispersible in food products. Even very fine
grinding does not disrupt all the cells, so
 Natural Flavoring Materials 239

TABLE 7-21. Characteristics of good average quality spices1

Volatile
Acid-insol Crude Oil
Total Ash (HCI)Ash Fibre Moisture (avg content)
Spice (max%) (max%) (max%) (max%) (%v/w)
Allspice (pimento) 5.0 0.4 25.0 8.0 3.0-4.5
Anise 9.0 1.5 1.5-3.5
Anise, China star 5.0 3.0
Basil, sweet 15.0 1.0 8.0 0.4
Bay laurel, sweet 4.5 0.5 30.0 9.0 4-10
Capsicum (cayenne) 8.0 1.25 28.0 7.0 nil
Caraway 8.0 1.0 18.0 9.0 2.5-7.5
Cardamom seed (decorticated) 8.0 3.0 30.0 9.0 4-10
Cassia/ cinnamon 5.0 2.0 20.0 10.0 0.5-4.0
Celery 10.0 2.0 2.5-3.0
Cinnamon (C.zeylanicum) 5.0 2.0 10.0 0.5-1.0
Clove 6.0 0.5 10.0 8.0 15-20
Coriander 7.0 1.0 25.0 9.0 0.4-1.0
Cumin 9.5 1.0 7.0 9.0 2.5-4.5
Dill 10.0 3.0 2-4
Fennel 9.0 1.0 14.0 7.5 4-6
Fenugreek 28.0 6.0 trace
Ginger, Jamaican 7.0 2.0 8.0 10.0 1-3
Mace 3.0 0.5 10.0 6.0 12-15
Marjoram, sweet 13.0 4.0 22.0 10.0 about1
Mustard, black 5.0 1.5
Nutmeg 3.0 0.5 5.0 8.0 6.5-15
Origanum 8.5 1.0 10.0 about3
Paprika 6.0 0.4 23.0 nil
Pepper, black 7.0 1.0 11.0 12.0 2.0-4.5
Pepper, white 2.0 0.3 5.0 12.0 1.5-2.5
Poppyseeed
Rosemary 12.0 4.0 6.0 0.5-2
Saffron 7.5 1.0 14%losson
drying
Safflower (Mexican saffron)
Sage, Dalmatian 10.0 1.0 10.0 1.5-2.5
Savory about 1
Sesame
Star anise 5.0 3.0
Tarragon (estragon)
Thyme 8.0 2.0 9.0 1.5-1.8
Turmeric (curcuma) 7.0 0.5 6.0 9.0 4-5
1 Detailed specifications giving maxima and/or minima values for specific requirements differ considerably between
importing countries and reference should be made to the currently accepted standards. Figures are generally quoted
on the material as received but recent international specifications are calculated on a "dry weight" basis as
appropriate. Test methods and several comparative tables of specifications are quoted by Pearson (1976).

that ground spices do retain a considerable high-speed disintegrators, hammer mills,

degree of their original stability during
storage and are better able to withstand
high-temperature processing (e.g., baking)
than many of the extracted processed spice
products.
Spice grinding calls for considerable
expertise in the handling of different types
of milling equipment called for to cope
with the wide spectrum of physical forms
encountered in the herbs and spices (Table
7-24). The milling of these aromatic mate-
rials is carried out with as little grinding as
possible so that the equipment ranges from
pin mills, plate mills, roller mills and ball
mills to slow-speed vertical and horizontal
buhrstone mills in a whole range of sizes and
capacities. Most high-speed mills generate
considerable heat and involve rapid air
movement, both of which may result in the
loss or degradation (oxidation) of valuable
volatile constituents from the spice dur-
ing its comminution. This is reflected in
specifications for ground spices, which
usually state a lower requirement for essen-
tial oil content than that for the unground
material.
 240 Source Book of Flavors
TABLE 7-22. Specific requirements for individual spices
Spice Test result
Allspice (pimento) Quercitannic acid (calculated from
the total oxygen absorbed by the
aqueous extract):
minimumS%.
Capsicums Pungency (expressed as Scoville
units) range: 12,000 to 130,000.
May also be quoted as capsaicin
content-150,000 Scoville units =
1% capsaicin.
Nonvolatile ether extractive:
minimum 15%. Starch: maxi-
mum 1.5%.
Clove Quercitannic acid (calculated
from the total oxygen absorbed
by the aqueous extract):
minimum 12%.
Clove stems: maximum 5%.
Volatile ether extract:
minimum 15%.
Ginger Starch: minimum 42%.
Lime (CaO): maximum 1%.
Cold-water extractive:
minimum 12%.
Total ash 7% of which not less
than 2% is water-soluble.
Ginger, limed Calcium carbonate:
maximum4%.
Total ash: maximum 10%.
Mustard, black Volatile oil (calculated as allyl
isothiocyanate): minimum 0.6%.
Saffron Yellow styles and other foreign
matter: maximum 10%.
Traditionally, the huge horizontal and
vertical stone mills, as well as fluted steel
roller mills operate at lower speeds and,
being cooler, reduce volatile losses. This
is of particular value in a widely used com-
modity such as ground black or white
pepper, where both aroma and pungency
are desirable attributes. Pepper mills gener-
ally consist of paired series of horizontal
corrugated steel rollers revolving at dif-
ferent speeds (usually in the ratio of 1:3,
with the higher-speed roller turning at
1000 rpm). The pepper passes down through
the rollers and the resulting powdered
material is fed into the sifters. Any pepper
that does not pass through the desired
screen is automatically returned for regrind-
ing. Stone milling is still preferred for high-
quality ground spices such as white pepper.
Various techniques have been developed
to minimize the heat formed during grind-
ing. Several designs for mills are based on
prechilling, water-cooling or refrigeration of
the grinding chamber, all aimed at main-
taining the spice at a temperature below
35°C (97°F). Cohodas (1969) patented a
process for the cyrogenic milling of spices
in which the spice stock and a gaseous
refrigerant (e.g., nitrogen at -l25°C) are
fed into the milling head at a constant rate.
The resulting ground spice and vapor dis-
charge was maintained at 25°C throughout
the process. Under such conditions, even
delicate herbs like sage show no signs of
discoloration and retain an excellent odor
and flavor.
Several spices require special handling:
Spices having a high volatile and/or fixed oil
content (e.g., nutmeg, mace, clove, allspice,
coriander and celery seed) are difficult to
reduce to a fine powder in a single opera-
tion. These spices are frequently first re-
duced to a very coarse powder by passage
through a slow-speed breaker or cutter mill
and are then ground to the desired fineness
in a second stage process.
Ground white pepper may be milled
directly from white pepper or normal black
pepper may be used as a source of this
product. In the latter case, the dark outer
skin is first removed from the peppercorns
by a process of decortication in a special
mill. Different grades of ground decorticated
(white) pepper are produced by a series of
decortications as necessary.
Cardamoms are commercially handled
as whole fruits or capsules whose tough
pericarps are almost flavorless. It is the
highly aromatic seeds that constitute the
real spice. For extraction or distillation,
the whole fruit is milled, but for sale as
ground cardamom the spice must be decorti-
cated and the seeds freed before milling.
The degree of fineness to which spices are
ground depends on the nature of the spice
itself and its ultimate application (i.e., for
extraction and distillation coarsely ground
materials are required; for direct use in
seasonings a finer product should be used).
Generally, it is necessary to compromise
to achieve the optimum balance between
available and retained flavor and at the
TABLE 7-23. Uses and chief producing areas of herbs and spices

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Aniseed Turkey, Spain, Syria

Basil France
Bay (Laurel) Turkey
** **
Caraway Netherlands * ** ** * *** * ** *** ***
Cardamom India, Guatemala
***
Cassia China * ** * ** * * * ** **
Capsicum and Cayenne Kenya, West Africa *
Celery India, France * * * **
Chervil France * * * * * *
Cinnamon Ceylon, Seychelles
*** ** ** *
Clove Zanzibar
Coriander Russia, Rumania, Morocco
** *** * *
Cumin Iran, India, Morocco * *
** * * *
Dill India, W. Germany *
Fenngreek India, Egypt. Morocco * *
Fennel India, Argentine, Germany
** * ** * *
Garlic Egypt. Italy * *** ** ** *
Ginger Jamaica, W. Africa, India
**
Mace West Indies. Indonesia
* * * * ** **
Ma.joram France
** ** **
Mustard U.K., Germany, France *
Nutmeg West Indies, Indonesia
** ** ** ** *** *** ** ** ** z
Onion Egypt, Hungary, Greece, U.S.A. ~
Oregano Mexico .....
.:
* ***
Origanum France, Spain, Greece
** *** *** *** *** *** ** * ** ....
Paprika Hungary, Spain, Morocco
** a
Parsley U.K.. Europe, U.S.A. :!1
** ** ** ** * ** ** **
Pepper Indonesia, Malaysia, India, Brazil
~
**
Pimento (Allspice) Jamaica, Mexico 0
* ** ** ** ** ** ** * **
Rosemary Spain * * * * * ::::!.
Sage Yugoslavia, Italy, Spain, U.K. Jg
Tarragon France
* **
Thyme France, Spain ~
~
*** *** ** *** *** *** *** ** ***
Turmeric India, Haiti
(D
** *
::::!.
** ** ** ** * ** ** **
Source: Heath (1966)
a
fJ'

~
......
 242 Source Book of Flavors

TABLE7-24. The physical character of herbs and spices Sifters are available in several designs
Physical and consist of one or more mechanically
Form Herbs and Spices oscillated screens of metal or bolting
Barks Can ella, cassia, cinnamon cloth, the sieving characteristics of which
Bulbs Garlic, onion are defined in international and national
Flower buds Caper, cassia buds, clove
Flowers Mexican saffron (safflower) standards.
Flower parts Most spices are ground to pass through a
(stigmas) Saffron
Fruits Allspice (pimento berry), angelica, U.S. Standard Testing sieve No. 20 to No.
anise, capsicum, caraway, carob, 60 mesh, or, in other countries, through
celery, coriander, cubeb, cumin, dill,
fennel, juniper berry, nutmeg, the equivalent national standard screens.
pepper (black and white), star anise, The term "mesh" applies to the number of
vanilla
Fruit part openings per linear inch measured from
(ariiJ Mace center to center of parallel wires. The
Leaves Bay laurel, basil, marjoram,
origanum, peppermint, sage, savory, aperture of the opening is, of course, deter-
spearmint, tarragon, thyme mined by the diameter of the screen wire or
Rhizomes Galangal, ginger, turmeric
Roots Angelica, calamus, horseradish, other material used. Screens may be either
sassafras of stainless steel, copper, silk, nylon or
Seeds Black cumin, cardamom, fenugreek,
grains of paradise, mustard (black polyester; the choice of material depends on
and white), poppy, sesame the nature of the ground spice or other
vegetable matter to be sieved. Oily spices
such as nutmeg and mace readily clog sieves
same time maintain an adequate degree of and may require brushing through or even
flavor stability to give an acceptable shelf- double sieving, first through a coarse mesh
life. Depending on the type and size of the and then through a fine mesh, to achieve the
internal screening in the mill, the initial desired product in a reasonable time.
grinding operation produces a powder with To ensure batch uniformity, ground
a wide range of particle sizes, depending spices must be remixed after sieving.
on the relative hardness of the constituent Several combined sifting/blending machines
tissues. It is necessary to sift this product are available for this purpose. Finely milled
to provide a powder with the desired fine- spices are advantageous in use as they blend
ness or to comply with a specified sieving more completely with other ingredients in a
specification. food mix, are less liable to show as unsightly

TABLE 7-25. Specifications for fineness of ground vegetable materials

All to Pass Sieve Maximum to Pass Through

Through Aperture
Sieve No. mJ.I % Sieve No.

United States
Very coarse 8 2380 20 60
Coarse 20 841 40 60
Medium coarse 40 420 40 80
Fine 60 250 40 100
Very fine 80 171 100 80
Great Britain
Coarse 1700 1700 40 355
Medium coarse 710 710 40 250
Medium fine 355 355 40 180
Fine 180 180 100 180
Very fine 125 125 100 125
Sources: U.S. Pharmacopoeia, 20th Edition (1980); National Formulary, 15th Edition (1980); British Pharmacopoeia
(1980).
 Natural Flavoring Materials 243

specks and more rapidly release flavor into TABLE 7-26. Microbiological contamination in spices
the end product. However, they do tend to Bacteria and Molds
lose volatiles more rapidly than medium or Colonies per Gram
coarsely ground material and must be stored Suspension Plated and
in well-closed containers; in most cases, Spice Incubated at
ground spices are supplied in fiber kegs 37·c Room Temp
having tightly fitting lids. Storage in multi-
layered paper sacks having an impervious Ground cayenne pepper 2,190,000 1,220,000
Ground celery seed 1,150,000 10,000
lining is also satisfactory, but not so good Ground cinnamon 8,000 600
once the sack has been opened. Ground clove 190 0
Ground coriander 410,000 80,000
The degree of fineness of ground spices Ground ginger
and other vegetable materials is defined in (Jamaican) 60,000 2,000
Ground nutmeg 1,200 700
most pharmacopoeias as well as in interna- Ground black pepper 10,400,000 1,300,000
tional standards. The designation of sieves Ground white pepper 42,000 9,000
Ground sage herb 550,000 70,000
differs in the United States and Europe, and Ground thyme herb 35,000 30,000
reference should be made to the respective Onion powder
(Californian) 6,000 0
specifications for details. The principal Onion powder (Egyptian)
requirements are given in Table 7-25.
Spice manufacturers may adopt their own
empirical classification and the following is with a relative humidity of 55-65 percent
representative of commercial standards for (max), out of direct sunlight, and away from
ground spices: radiators or cold floors and clear of damp
outside walls subject to condensation.
Coarse Over 30% retained on a No.30 The advantages and disadvantages of
U.S. sieve using ground herbs and spices in food pro-
Medium Less than 30% retained on a cessing have been discussed by Heath
No.30 U.S. sieve; (1978).
more than 50% retained on a
No.60 U.S. sieve Sterilized Spices
Fine Less than 2% retained on a No.30 A long-held objection to the use of ground
U.S. sieve; spices in food processing is their poor
less than 35% retained on a hygienic quality. The figures quoted in
No.60 U.S. sieve Table 7-26 demonstrate the degree of
Very fine 50% to pass through a No.100 microbial contamination and show the wide
U.S. sieve variability encountered between different
spices. This is not surprising when one con-
The moisture content of ground spices is siders the tropical and semitropical origins
of importance to both their stability and of these materials. Practically no attempt is
flavor value; they must be dry enough to made to limit contamination either during
prevent mold growth and the development growth or preparation for market. With
of a musty odor and flavor, and yet be moist certain spices, either handled in consider-
enough to retain the optimum odor and able bulk (e.g., black pepper) or under
flavor character. Ground spices generally strict government control (e.g., clove in
fall within the range 8-10 percent. Tanzania), the exporter does carry out a
High ambient storage temperatures can cleaning process to remove grosser forms of
cause flavor loss, caking and often undesir- contamination prior to bagging for ship-
able color changes, particularly in ground ment. This usually involves a blowing or
herbs, so that stocks should be stored at a winnowing operation to remove heavy
temperature between 10-l5°C (50-60°F), stones or light extraneous matter. But, even
 244 Source Book of Flavors
where this cleaning or garbling is carried
out, bags of spices are often stored for
extended periods in dockside warehouses
where they are exposed to the ravages of
rodents and insects. As the ambient climate
is frequently very humid, many spices may
become mold-contaminated during this
period and develop heavy mold growths
during subsequent shipment. A wide range
of microorganisms have been identified
in imported spices (Krishnaswamey 1974;
Julseth and Deibel 1974; Baxter and
Holzapfel 1982; Powers, Lawyer and
Masuoka 1975). These include saprophytic
bacteria, thermophilic bacteria and spores,
yeasts and molds. The majority of these
organisms are not necessarily harmful to
health, but may contribute to the spoilage of
food products in which spices are used as
ingredients. Economically, it is not practical
to prepare beforehand for market the
unground spices that have a significantly
lower bacterial count than ground spices.
The nature of the spices, the customs and
character of the producing countries and
the general conditions prevailing through-
out their handling lead one to conclude
that there is little in the way of improved
handling and storage that can be achieved.
In spite of this, the problem, so far as the
food technologist is concerned, is still one
of reducing the initial bacterial load in the
processed food without in any way affecting
the aroma and flavor of the end product.
Two solutions are possible: the use of
sterilized spices or of seasonings based on
essential oils and/or oleoresins.
Heat Treatment
The microbial load of spices may be reduced
using heat treatment, chemical treatment
or irradiation (Weber 1980). Heat is an
obvious way to sterilize any material, but as
herbs and spices are highly aromatic they
are liable to incur damage by such a process.
Direct heat treatment is likely to result in a
15 to 20 percent loss of available flavor
and may be accompanied by unacceptable
changes in flavor quality and color. The heat
sterilization of spices, is, therefore, of no
commercial interest.
Chemical Treatment
Early work on the vapor sterilization of
spices was largely an extension of the pro-
cess of fumigation employed to control
insect infestation. The treatment of whole
spices with chemicals such as formaldehyde,
carbon disulfide and chloropicrin has only a
limited value, as these gases often impart
undesirable odors and/or flavors to the
treated spices. Gaseous treatment of whole
spices is also imprecise in its sterilizing effect
owing to the variability of effective penetra-
tion of the gases at lethal levels.
The treatment of spices with ethylene
oxide or a mixture of ethylene oxide and
carbon dioxide (90: 10) has been a com-
mercial process for many years. The process
consists of spreading the spice in a suitable
chamber, which is then evacuated. The
temperature of the material is raised to 60°C
(140°F), at which temperature the volatile
loss is less than 1 percent. A predetermined
quantity of the sterilizing gases is then
introduced and the conditions maintained
until sterilization is complete. The time
interval, as well as other processing condi-
tions, vary with the spice and its physical
character. Under the Food Additives
Amendment (21 CFR Section 121.1076),
the treatment time when using propylene
oxide is limited to 4 hrs. at a temperature
not exceeding l25°F (50°C). Under Sections
120.151 and 121.1232, the use of ethylene
oxide is not so precisely defined. At the
completion of the sterilization cycle, the
gases are withdrawn and the space sparged
with air several times before returning to
normal atmospheric pressure. The material
is tested for residual ethylene oxide or other
sterilant as appropriate, and it is claimed
that no residual gas can be detected under
these processing conditions. In the United
States, the limit of residual propylene oxide
is 300ppm and of ethylene oxide is 50 ppm.
From a bacteriological point of view this
method is extremely effective in reducing
 Natural Flavoring Materials 245

TABLE 7-27. Effect of ethylene oxide treatment on microbial load in capsicums

Untreated Treated

Type Min. Max. Min. Max.

Paprika 180,000 22,900,000 300 8,200

Cayenne 13,000,000 <10 1,900
Red pepper (chillies) 73,000 600,000 <10 3,200

Effect of Fumigation on Bacterial Count, pH, and Color of Ground Paprika

Lovibond reading
Bacterial count
Treatment per gram pH Red Yellow Blue

Unfumigated 1.6 X 106 5.5 11.0 11.9 1.5

control
Etox 2.0 X 104 5.7 11.0 10.6 1.2
(1 ,000 g/m 3 /6 hr)"
Etox 4.1 X 103 5.3 11.0 12.0 1.3
(1,000 g/m 3 /6 hr)h
Etox 8.7 X 103 5.8 11.3 10.7 1.3
(1 ,000 g/m 3 /16 hr)"
Etoxicant 9.8 X 103 5.5 11.0 12.0 1.3
(1 ,000 g/m 3 /16 hr)b
"90% Ethylene oxide + 10% carbon dioxide.
h50% Ethylene oxide + 50% methyl formate.

the bacterial load to acceptable levels, if
not to complete sterility (Table 7-27). The
concentration of gases used rarely penetrates
sufficiently to kill all of the bacteria and
bacterial spores present, nor does the tech-
nique get rid of rodent hairs and other
extraneous filth which, however sterile, are
still objectionable in a finished food pro-
duct. It is found that spices treated in
this manner do have a somewhat different
profile from the untreated material. Many
of the sterilants are also to some extent
solvents and there is a loss of essential oil
content due to the combined effect of this,
and the need to carry out the process with
some heat and under vacuum.
Irradiation
Irradiation for the sterilization of spices has
been studied for several years. Irradiation is
desirable for the treatment of spices and
herbs since it is very effective in killing
microorganisms and leaves no chemical
residue. While high levels of irradiation will
induce changes in flavor, it has been found
that doses of 1 to 2 Mrads have no sig-
nificant effect on spice quality (Gottschalk
1977). Since cost of treatment increases with
dosage, minimum dosage is determined
based on material treated, microbial load
and types of treatment.
The major drawbacks of irradiation are
the cost of treatment, regulatory status
and consumer perception of the process.
Despite the advantages of irradiation, these
issues will limit use of the process for some
time.
Essential Oils
With the exception of the capsicums, all
herbs and spices depend on their content of
essential oil for their distinctive character
(which may range from less than 1 percent
in many of the herbs to 18 percent in clove
buds). These steam-distillable components
may be recovered from the mass of inert
cellular matter by distillation of the ground
material or from the freshly harvested herb.
246 Source Book of Flavors
It is well recognized that spices also contain
nonvolatile components, which may make
a significant contribution to their overall
flavoring effect-e.g., black pepper in
which the essential oil is bland and pleas-
ingly aromatic, whereas the nonvolatile
fraction extracted with a suitable solvent
is highly pungent due to the presence of
piperine and related compounds. In ginger,
the essential oil gives the characteristic
aroma, but lacks the intense pungency
of the complex of nonvolatile compounds
present in this spice. Turmeric contains up
to 5 percent of a highly aromatic essential
oil, but the distinctive yellow coloring
matter is in the nonvolatile fraction.
Essential oils are complex mixtures of
chemicals whose relative proportions are
usually characteristic of a given spice, but
may vary depending on the species, source
and environmental conditions during
growth, harvesting and preparation of the
spice for market. For any specific spice the
essential oil constituents vary within much
narrower limits, depending more on distilla-
tion technique and conditions used in its
recovery. Steam-distilled essential oils
rarely contain all the odoriferous aromatics
present in the original spice, as some of
these are high-boiling chemicals that are
difficult to distill; others are unstable and
undergo change during the process; and a
few are water soluble and are lost in the
aqueous distillate.
Distillation of Herbs and Spices
The distillation of aromatic plant materials
has been well described in the literature
(Guenther 1948-1952; Gildermeister and
Hoffman 1965-1967, Ames and Matthews
1968, Provatoroff 1973 and Ashurst 1991),
and is also discussed in detail later in this
text (Flavor Manufacturing, Chapter 11).
Therefore, only a brief discussion of the
process as it applies to spices is necessary
here.
There are three types of prime distillation
of aromatic plant materials: (a) water dis-
tillation, (b) water and steam distillation,
and (c) steam distillation, differing only in
the method of handling and the type of stills
used.
Water Distillation The plant material in
the still is entirely covered with water, which
is then brought to the boil. The still contents
are continuously stirred throughout the dis-
tillation. The method is used for materials
that tend to agglomerate and compact when
steam-distilled but is not suitable for spices
containing starch (e.g., ginger).
Water and Steam Distillation The prep-
ared material is supported on a grid fixed
over a layer of water in the bottom of the
still. The water is boiled by a steam jacket
and the steam produced in the still is satu-
rated and at low pressure.
Steam Distillation The prepared mate-
rial is supported in layers on grids set
at intervals in a still body. Live steam is
injected into the bottom of the still. The
method uses superheated steam at higher
than atmospheric pressure. This is the tech-
nique most widely used in the distillation of
spice essential oils.
The aqueous/oil distillate is separated
continuously as it leaves the condenser, and
the aqueous fraction may be returned to the
still via a special trap or lead into a re-boiler
unit as a source of further steam. As the
condensed water is saturated with essential
oil components, the recycling leads to a
higher yield and a more balanced final pro-
duct. Dissolved oil also may be recovered
by extraction of the aqueous distillate with
successive washing of an immiscible solvent,
which is then removed under high vacuum.
Green Herbs
Freshly harvested green herb crops (e.g.,
peppermint, spearmint, sage, etc.) vary
considerably in their moisture content, and
the distillation conditions are influenced by
the way in which the cut herb is handled
prior to loading into the still. Excessively
wet material is difficult to distill and yields
oil very slowly. This makes the complete
recovery expensive in steam use and un-

acceptably long. Most herbs are allowed to
field dry in the sun for several hours before
distillation, although it is recognized that
this could lead to both volatile losses and a
change in the character of the oil.
The stills used are purpose designed and
are of about 250kg. capacity. They have
removable tops to allow for easy load-
ing onto a grid designed so that the spent
material can be hoisted clear as a single load
at the end of the distillation. Live steam
is injected into the still through a per-
forated coil and this may be supplemented
by reboiling the aqueous distillate.
Owing to the very considerable acreages
involved and the need to handle large
tonnages of freshly harvested herb quickly,
the distillation of peppermint in the United
States calls for special equipment. The herb
is cut and allowed to dry (mint hay) for
several hours before distillation. The larger
farmers handle the crop speedily as the mint
reaches maturity. The dried chopped herb is
loaded into trucks, the body of which is the
still itself. On return to base, the canopy or
distilling head is lowered onto the truck,
firmly bolted down and the steam pipe
connected so that distillation proceeds in
situ. Distillation takes about 1Vz to 2 hrs.,
although the bulk of the available oil is
recovered in the first 15-20min. When the
herb is exhausted, the truck is disconnected
and the spent material is tipped out for later
use as a field dressing or manure.
The yield of essential oil from freshly cut
herbs is usually quoted as kilograms per
hectare or pounds per acre, rather than as
a percentage that depends entirely on the
state of dryness of the cut material at the
time of distillation.
Dried Herbs and Spices
Essential oils are found in special cells,
glands or ducts located in several parts of
the plant tissues, sometimes confined to
particular structures and often throughout
the whole plant. The essential oil can be
released from these intact cells only by a
process of slow diffusion so that distillation
Natural Flavoring Materials 247
of unbroken material is necessarily slow.
For most herbs and spices, it is necessary
to comminute the dried material before dis-
tillation, breaking open as many cells as
possible to allow ready access of steam and a
more rapid rate of recovery. The degree of
comminution is dictated by the nature of the
herb or spice:
Flowers, leaves, broken herbs: no com-
minution is necessary.
Seeds and fruits: crushed by rollers.
Roots, rhizomes, stems, barks: disintegrated
to a coarse powder.
In all cases, distillation of the com-
minuted material should be carried out
immediately to reduce volatile losses to a
minimum.
The production of high-quality spice
essential oils depends on the careful selec-
tion and grading of the raw materials as well
as on establishing their authenticity. There
is considerable overlapping of certain
botanical entities, particularly among the
herbs that readily form hybrids. This, added
to the ever-present vagaries of climate,
habitat and cultural environment, makes
selection of material for distillation a dif-
ficult and exacting responsibility. This
emphasizes the need for careful sampling
and analytical control of all raw materials.
Another complication arises in that many
spice-bearing plants produce essential oils in
different parts of their structure (e.g., clove
oil is present in the flower buds, leaves
and stems). These oils may be similar in
character and constitution (e.g., angelica
root and seed, pimento berry and leaf) or
entirely different (e.g., cinnamon bark
and leaf). The use of these alternative oils
is widespread and the industry has long
produced blends of essential oils to suit
specific manufacturers' needs for both flavor
and cost. The admixture of oils from dif-
ferent sources offers considerable opportu-
nities to create new flavoring effects and is
quite acceptable, so long as the product is
248 Source Book of Flavors
correctly labeled and the products are what
they purport to be.
Rectification of Peppermint Oil
Natural peppermint oil is obtained by
the direct steam distillation of the freshly
harvested and wilted herb. When freshly
distilled, the oil has a rank unpleasant
sulfurous character with somewhat "weedy"
overtones. This profile quickly modifies on
standing, but is not radically improved
unless the oil is redistilled or rectified. This
vacuum redistillation is required for an oil
to comply with the USP specification for
peppermint oil.
The process of rectification certainly
improves the aromatic quality of the original
oil, but it is not just an expedient for turning
a poor-quality oil into a good one. Rectifica-
tion, in effect, concentrates an oil and in so
doing may accentuate any abnormalities or
in balance of constituents, making the profile
worse rather than better. Rectification is
carried out to varying degrees depending on
the intended end use of the product. In the
case of peppermint, the "single rectified"
or "double distilled" oil involves vacuum
distillation of the natural oil with rejection
of the last 2-4 percent remaining in the still.
These residues are normally resinous and
foul-smelling. "Double rectified" or "triple
distilled" peppermint oil involves only one
distillation process in which the first frac-
tions of the distillate, up to whatever
percentage is considered necessary but
usually 5-10 percent, are rejected as well as
the final 2-5 percent of still residues.
The process of rectification is fully
described by Guenther (1948-1952).
Quality of Spice Essential Oils
Many herb and spice essential oils are
recovered from imported materials under
carefully controlled conditions in modern
still-rooms. Many of the major flavor manu-
facturers in Europe and the United States
as well as several specialist houses have
extensive distillation facilities. Some oils,
however, are distilled under relatively
primitive field conditions in the producing
regions (e.g., cassia oil). Such products are
often of indifferent quality and may vary
greatly from lot to lot. It is usual to purchase
such essential oils on sample only and
to carefully compare the bulk against the
forward sample before final acceptance.
Specifications for essential oils are given in
many pharmacopoeias; and the standards of
EOA, as well as several international and
national standards. Such specifications
generally include:
Description: the source material.
Physical appearance: nature and color of
oil.
Specific gravity 15°/15°C (or weight per
milliliter at 20°C): in EOA specifications
a temperature factor is also quoted to
allow for determinations at other more
appropriate ambient temperatures.
Optical rotation at 20°C.
Refractive index at 20°C.
Solubility in alcohol of a designated strength:
in terms of volumes of solvent to produce
a clear solution.
Specific requirements: physicochemical tests
to establish the content of selected com-
ponents or groups of compounds.
In addition to these tests, a sensory
assessment, particularly of the aroma,
against a control sample is an essential
prerequisite of acceptance.
These tests have proved more than
adequate over many years, but with the
advent and wide application of instrumental
methods of analysis, essential oils are now
frequently examined by one or more of the
following test methods: infrared spectros-
copy, ultraviolet spectrophotometry, thin
layer chromatography, high-pressure liquid
chromatography and gas chromatography.
The physicochemical and sensory charac-
ters of the herb and spice essential oils
are quoted under individual spices later in
this section. Manufacturers will supply the
specifications applicable to their range of
 Natural Flavoring Materials 249

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FIGURE 7-9. Flow sheet of paprika oleoresin production. (Govindarajan 1986)

250 Source Book of Flavors
products or will indicate, often in the title,
which published standards are met.
Spice Oleoresins
The nonvolatile flavoring constituents of
herbs and spices are recoverable by extrac-
tion. In practice, a solvent is chosen which
dissolves both the essential oil and non-
volatiles present, the resulting solvent-free
product being known as an oleoresin.
Oleoresins are prepared from selected
dried herbs and spices by extraction with a
volatile organic solvent capable of recover-
ing the optimum spectrum of volatile and
nonvolatile flavoring components. Recently
liquified gases such as carbon dioxide are
currently being used as well as the applica-
tion of ultrasonics to increase the extrac-
tion rate and yields. The most widely used
extraction process involves the following
unit operations (see Fig. 7-9).
Preparation of the Raw Material
Very few plant materials are amenable to
extraction in their natural forms and must
be first ground or comminuted to a particle
size sufficiently small to enable the solvent
to penetrate the mass completely, but not so
fine as to reduce the rate of penetration and
liquid circulation in and through the mass.
The smaller the particle size, the greater the
number of broken cells available for easy
extraction, the greater the interfacial area
and, hence, the greater the speed of achiev-
ing equilibrium and transfer of solutes. But
this is coupled with slow percolation rates
and a difficulty in recovering solvent from
the spent material (marc) at the end of the
process. The correct degree of fineness
is, therefore, of importance in achieving
maximum yields in optimum time with the
minimum of solvent. Each product to be
extracted demands individual consideration
and one cannot generalize on particle size.
Size reduction is generally a simple opera-
tion, the material being subjected to either
crushing, grinding, rolling or impact.
Certain materials such as nutmegs, which
contain about 30 percent fatty constituents
and 10-15 percent essential oil, pose prob-
lems as direct milling may result in the
production of a paste-like mass that cannot
be adequately extracted. Pepper, too, has to
be properly flaked to facilitate extraction
and reduce volatile losses during the milling.
Many natural products intended for
extraction are subjected to indifferent
handling at origin and it is absolutely essen-
tial to have suitable magnetic protectors
on any milling equipment if mechanical
damage and possible explosion or fire are to
be avoided. One would be very surprised at
the nature of metallic junk that is found in
some spices; knives, nails and even horse-
shoes are not uncommon.
Exposure of the Material to Solvent
This part of the extraction process involves
three distinct phases: (a) the addition of
the solvent and its penetration into the dry
mass; (b) the achievement of equilibrium;
and (c) the replacement of the solute with
new solvent. This may be done by packing
the dry material into a suitable extractor,
spraying the solvent onto the mass until it is
completely saturated, allowing a period of
time for maceration followed by percolation,
and the addition of new or recovered
solvent to the top of the vessel, maintain-
ing a uniform flow until the extraction is
complete.
The design of the extractor is dictated by
the quantity of material to be handled. If
this is small or if the plant is required to be
used for a range of different materials, it is
generally more economical to carry out the
extraction on a batch basis; if large tonnages
are to be extracted, particularly if these
are of one raw material, then a battery of
extractors or a continuous extraction system
is called for.
Packing of the extractor involves some
expertise so as to minimize the effects of
swelling, which will unduly restrict the
rate of flow of polar solvents or channeling,
which permits uneven extraction and poor
yields.
Extraction is normally carried out at

room temperature, although extractors may
be provided with facilities that enable the
temperature of extraction to be controlled
by a steam and/or water jacket. The solvent
may pass through the extractor under
gravity or it may be pump-circulated; in
either case, the solvent recovered from the
early runnings is recovered and returned for
circulation. This may pose a problem in the
case of water miscible or polar solvents, as
any moisture present in the herb or spice
will be extracted by the solvent and so dilute
it. This may result in the extraction of
unwanted salts, gums, etc., from the plant
material.
The system of recycling the solvent
is important and will be decided by the
solvent used, the temperature at which the
extraction takes place, the degree of heat
treatment feasible without damage to the
constituents, the established flow rate and
an acceptable drug/solvent ratio. The prin-
ciple of countercurrent flow to improve
yields is not applicable to single batch
extraction, but in continuous processing it
is common practice to mount extractors in
batteries. The solvent is pumped through a
series to achieve multiple contact extraction
and the miscella increases in concentration
as it passes from one extractor to the next in
line.
The principle of the laboratory Soxhlet
extractor has also been applied to medium-
scale extraction, although this is more
applicable to botanicals that do not contain
aromatic components adversely affected by
the temperatures involved. For successful
operation the system has to be very carefully
balanced.
As an alternative to static-bed per-
colation, two other methods have been
tried with varying degrees of success:
(a) exposure of the comminuted spice in
a modified blender-mixer followed by
removal of the miscella through a suitable
screen, (b) passage of the suspended ground
spice through an ultrasonic field followed
by separation of the solute in a continuous
clearing centrifuge. Both methods are rapid,
Natural Flavoring Materials 251
TABLE 7-28. Limits for residual solvents in spice
oleoresins
Solvent Max permitted (ppm)
Acetone 30
Methanol 50
Isopropanol 50
Hexane 25
All chlorinated solvents 30
Source: United States Federal Register (1990)-Food
Additive Regulations 173.210-173.290.
but have inherent difficulties particularly
with solvent loss and possible fire and health
hazards. In each case, a specially designed
plant is necessary and represents a high
capital outlay.
Separation of the Solute or Miscella
from the Marc
The ground material normally acts as its
own filter; the clear miscella passes directly
to a still or evaporator.
Removal of the Solvent
In the case of herbs and spices, the stripping
of the solvent from the desired extractives is
of immense importance to the quality of the
end product. In the case of highly aromatic
materials, the solvent should be evaporated
from other low-boiling constituents as
rapidly as possible at the lowest practical
temperature so as to avoid loss of or damage
to the flavor profile. For this reason, the
lower the solvent boiling point, the better.
The miscella is usually processed in two
stages: (a) the removal of some 95 percent
of the solvent in a standard falling-film,
rising-film or calandria-type evaporator; (b)
the concentrated miscella passes through
a special scrubbing, sparging and vacuum
treatment, which removes the final traces of
solvent down to the very low levels now
legislated in many countries (Table 7-28).
Solvents
The most widely used solvents in the pro-
cessing of aromatic plant materials can be
divided into two main categories-polar
and nonpolar. The polar solvents contain
hydroxy or carboxy groups, are relatively
reactive chemicals with high dielectric
252 Source Book of Flavors
constants, and are miscible with water.
The nonpolar solvents are more chemically
inert, have low dielectric constants, and are
generally immiscible with water. The polar
solvents are usually more powerful and
dissolve a much wider range of substances
than do the nonpolar solvents. In handling
large volumes of solvents, flammability and
toxicity are of major importance particularly
if there is any risk of escaping vapors.
The nonflammable chlorinated solvents are
generally more toxic and can result in
chronic poisoning, whose onset is slow,
leading to an almost imperceptible deteri-
oration in the health of workers exposed
to them in low concentrations over a long
period. The flavor of herbs and spices is
due to both volatile and nonvolatile com-
ponents, which themselves may be either
hydrophobic or hydrophylic, thus determin-
ing their relative solubility in polar and
nonpolar solvents. This determines, in turn,
which solvent will give the optimum balance
of extracted flavoring components.
Acetone and ethanol are obvious solvents
of choice, but the former is highly flammable
and requires a special flash-proof plant and
ancillaries, whereas the latter is generally
too expensive unless denatured and exempt
from duty. Both solvents are affected by
the presence of water in the ground plant
material and with constant use must be
periodically redistilled to remove the
accumulated water. Hexane has a good
solvent action on essential oils and fats, but
yields oleo resins that lack "body." It is, of
course, very highly flammable and special
precautions are necessary in handling it.
Somewhat similar results are obtained by
the use of the chlorinated solvents such as
methylene dichloride. This solvent has the
advantage of nonflammability, but is a rela-
tively high toxic hazard demanding a very
high level of safety precautions through-
out the process. Being low boiling point
materials, the removal of the chlorinated
solvents from the final oleoresin requires
much less energy than with almost all the
other solvents.
Recovery of Residual Solvent from Marc
The extracted spice (marc) is saturated with
solvent, which may be recovered by blowing
live steam or hot air through the mass in the
extractor, or by heating the spent material
in steam jacketed horizontal drums fitted
with paddles, or by passing the wet marc
through a screw-fed jacketed desolventizer.
In the first method, care must be taken to
ensure that the whole mass does not rise in
the extractor and form a tight plug, or that
channeling does not occur, as such a marc
would then carry a high level of residual
solvent in those areas untouched by the
steam or hot air stream and could pose a
hazard when the extractor is discharged. In
the other techniques, the removal of the
marc from the extractor must be achieved
within a sealed system, again to prevent fire
or health hazards. In each case, the solvent
is collected and rectified or purified as
necessary before reuse.
Disposal of Waste Matter
Waste poses a problem. The steam-wet
material is generally dumped and used as a
field manure.
The detailed techniques employed by the
specialist manufacturers of spice oleoresins
may differ somewhat from the above,
depending on the facilities available and the
range of products offered. In all cases, con-
siderable expertise is necessary to achieve
satisfactory products of a consistently high
quality.
Quality of Spice Oleoresins
The physical character of oleoresins ranges
from viscous oils to thick tacky pastes,
making their direct incorporation into food
products difficult. To assist in handling, the
more intractable oleoresins are frequently
mixed with a diluent such as propylene
glycol or a selected oil. The presence of any
such additives should be clearly indicated in
the specification for the product and on any
labels. The product should also be easily
distinguished by title from the undiluted
oleoresin.
 Natural Flavoring Materials 253

The balance of volatile oil to nonvolatile A comprehensive and critical review of

resinous matter in the oleoresin should be analytical methods for the evaluation of
similar to that of the original spice. In many seasoning extracts (oleoresins) and essential
commercially available oleoresins, this is oils from seasonings has been published by
so; but several of the major producers Salzer (1975a,b). Additional information on
have formulated a range of so-called methods for the evaluation of oleoresins is
"standardized oleoresins" having specified presented in the chapter of this text on
characteristics different from those found quality control.
in the natural spice. These products are
designed to suit some particular end use.
Their preparation involves the blending Uses of Oleoresins
of the basic oleoresin with essential oils The advantages and disadvantages of using
derived by distillation, usually but not spice oleoresins in food processing have
necessarily from the same source material. been discussed by Staniforth (1973) and
Different qualities of essential oil may Cripps (1973) and reviewed by Heath (1973,
be selected to satisfy known demands, and 1978). From these prime extractives of
the manufacturer's literature should be herbs and spices, numerous secondary pro-
consulted to confirm the analytical data ducts have been developed to provide the
on available products and their claimed food manufacturer with a comprehensive
equivalency to natural spice. range of purpose-formulated, standardized
The specifications for an oleoresin should seasonings compatible with, and able to
include the following requirements (Stahl, withstand, most all processing conditions.
1973): These products include:
Essences Prepared by the maceration
Description: a statement of the source of the ground spice materials in 70 percent
material and the presence of any addi- ethanol. The resulting product may be
tives: color; physical form. fortified with topping notes compounded
General tests of primary usefulness: from essential oils and/or oleoresins. In the
Moisture content. United States, the term "extract" is often
Solubility in defined solvents. applied to a flavoring essence, but has a
Volatile and nonvolatile ether extract. defined meaning under the Food and Drug
Volatile oil content-expressed as regulations.
ml/100 g or% v/w. Emulsions Liquid seasonings prepared
Character of recovered essential oil should by emulsifying blended essential oils and/or
be examined to include: aroma, optical oleoresins with gum acacia (Arabic) or
rotation, refractive index and, if possible, other permitted emulsifying agents. A
a gas chromatogram. stabilizer may be added to prevent cream-
Solvent residue. ing. These products may have a very limited
Specific tests applicable to certain spice shelf-life.
oleoresins: Solubilized Spices Blended essential
Capsicum: pungency in terms of Scoville oils and/or oleoresins mixed with one of the
units or capsaicin content. polysorbate esters (e.g., Polysorbate 80)
Ginger: pungency in terms of gingerol. in such a concentration as to give a clear
Paprika and Red Capsicum: color value in solution when mixed with water (Chislett
ASTA units. and Walford 1976).
Pepper (Black and White): piperine content Dispersed Spices (dry soluble spices)
by a defined method of analysis. Prepared by dispersing the standardized
Turmeric: color value in empirical units or oleoresin onto an edible carrier (e.g., salt,
curcumin content. dextrose, cracker meal, rusk, etc.) to give a
254 Source Book of Flavors
product having a flavor strength equal to
that of a good average-quality ground spice.
Encapsulated Spices Prepared from
essential oils and/or standardized oleoresins
by spray-drying with gum acacia (Arabic) or
a modified starch as the encapsulant. These
products are formulated to be 5 to 10 times
the flavoring strength of the equivalent
ground spice.
Heat-Resistant Spices Specialty prod-
ucts in which the capsules are rendered
water-insoluble and only release their con-
tained flavor at high temperatures such as
in baking.
Fat-Based Spices Blends of essential
oils and/or oleoresins in a liquid edible oil or
hydrogenated fat base, formulated for use in
such products as mayonnaise.
These products are marketed under
the manufacturer's trade names, either
as individual herbs and spices or blended
together as seasonings ready for use.
Reference should be made to the supplier's
literature and specifications to determine
the equivalent flavoring strength and
suggested use rate.
References: Herbs and Spices (General)
Akgul, A. 1989. Antioxidant properties of herbs
and spices. Turk Tarim Ormancilik Derg.
13(1):11-25.
Ames, G.R. and Matthews, W.S.A. 1968. The
distillation of essential oils. Perfum. Essent.
Oil Rec. 60(1):9-8.
Anon. 1976. ISO activities-international
standardization of essential oils. Perfum.
Flavor. 1(4):27-29.
AOAC. 1984. Official Methods of Analysis, 14th
Edition. Washington, D.C.: Association of
Official Analytical Chemists.
Ashurst, P.R. 1991. Food Flavorings. New York:
Van Nostrand Reinhold.
AST A. 1978. Analytical Methods of the
American Spice Trade Association, 3rd
Edition. Englewood Cliffs, N.J.: American
Spice Trade Association.
Baxter, R. and Holzapfel, W.H. 1982. A
microbial investigation of selected spices,
herbs, and additives in South Africa. J. Food
Sci. 47:570.
British Herbal Medicine Association. 1990.
British Herbal Pharmacopoeia. London:
Dorset.
Chislett, L.R. and Walford, J. 1976. Sorbitan
and polyoxyethylene sorbitan esters in 11 food
products. Int. Flavours Food Additives 7(2):
61-68.
Cohodas, A.M. 1969. Spice grinding process.
Can. Pat. 808, 644, Mar. 18.
Cripps, H.M. 1973. Spice oleoresins, the process,
the market, the future. Trap. Prod. Inst.
Conf. Proc., London.
Farkas, J. and Andrassy, E. 1988. Comparative
analysis of spices decontaminated by ethylene
oxide or gamma radiation. Acta Aliment.
17(1 ):77 -94.
Formacek, V. and Kubeczka, K.-H., 1982.
Essential Oils Analysis by Capillary
Gas Chromatography and Carbon-13 NMR
Spectroscopy. New York: John Wiley & Sons.
Forstreuter-Kuenstler, M. and Albert. B. 1984.
Inhibition of microorganisms with spices.
Lebensm. Gerichtl. Chern. 38(6):143-145.
Gildermeister, E. and Hoffman, F.R. 1965-
1967. The Essential Oils, Vol. I- VII.
Akademie-Verlag, Liepzig, Germany.
(German)
Gottschalk, H.M. 1977. A review on spices-
present status of decontamination technique
such as gamma radiation. In Food Irradiation
No. 7, Instituit fiir Strahlen Technologie,
Germany.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I- VI. New York: D. Van Nostrand Co.
Heath, H.B. 1966. The right way to use spices.
Food Manuf. Ingredients Surv. Jan.:45-46.
Heath, H.B. 1983. Spices and aromatic extracts,
influence of technological parameters on
quality. Colloq. Int. Aromes. Aliment. p. 138.
Heath, H.B. 1973. Herbs and spices for food
manufacture. Trap. Sci. 14:45-259.
Heath, H.B. 1968. The evaluation of herbs and
spices. Can. Inst. Food Techno!. J. 1(1):9-36.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn.:
A VI Publishing Co.
Julseth, R.M. and Deibel, R.H. 1974. Microbial
profile of selected spices and herbs at import.
J. Milk Food Techno!. 37(8):14-419.
Koller, W.D. 1988. Problems with the flavor of

herbs and spices. In Frontiers of Flavors, ed.
G. Charalambous. pp. 123-132. Amsterdam:
Elsevier.
Krishnaswamey, M.A. 1974. Microbiological
quality of certain spices. Indian Spices
11(112):6-11.
Lawrence, B.M. 1978-1989. Essential Oils,
1976-1978, Parts 1 & 2, 1979-1980, 1981-
1987. Wheaton: Allured Publishing Corp.
Lawrence, B.M. 1976. Essential oils-rearrange-
ment during distillation. Perfum. Flavor.
1(5):15.
Lawrence, B.M. 1977. Major tropical spices-
General introduction. Perfum. Flavor. 1(6):
15-19. General bibliography. Ibid. 1(6):
20-26.
Lewis, Y.S. 1973. The importance of selecting
the proper variety of a spice for oil and
oleoresin extraction. Trap. Prod. Inst. Conf.
Proc., London.
National Formulary, 15th Edition. 1980.
American Pharmaceutical Association, 2215
Constitution Ave., Washington, D.C.
Pesek, C. A., Wilson, L.A., and Hammond,
E.G. 1985. Spice quality: effect of erogenic
and ambient grinding on volatiles. J. Food
Sci. 50(3):599.
Pollock, C. 1974. Tools ofthe flavorist-essential
oils and oleoresins. Flavour Ind. 5:244-246.
Powers, E.M., Lawyer, E.R., and Masuka, Y.
1975. Microbiology of processed spices. J.
Milk Food Techno!. 38:683-687.
Provatoroff, N. 1973. Some details of the distilla-
tion of spice oils. Trap. Prod. Inst. Conf.
Proc., London.
Salzer, U-J. 1975a. Routine analysis of spice
constituents represented by a study of
extracts (oleoresins). Mitteilungsbl. GDCH-
Fachgruppe Lebensmittelchem. Gerichtl.
Chern. 29(3/4):132-153. (German)
Salzer, U-J. 1975b. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:51-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Stahl, W.M. 1973. Oleoresin quality analysis-
fact or fiction? Trap. Sci. 14:335-345.
Staniforth, V. 1973. Spices or oleoresins. A
choice? Trop. Prod. lnst. Conf. Proc.,
London.
United States Pharmacopoeia. 20th Edition.
1980. United States Pharmacopoeial Conven-
tion. Rockville. Maryland.
Natural Flavoring Materials 255
Weber, F.E. 1980. Controlling microorganisms
in spices. Cereal Foods World 25:319.
Essential Oils and Oleoresins of Herbs
and Spices (Listed Alphabetically)
Allspice (Pimento, Jamaican Pepper)
Allspice is the dried, nearly ripe fruit of
a large evergreen tree ( Pimenta dioica L.,
formerly classified as Pimenta officina/is
Lindley), which is a native of the West
Indies and parts of Central America. In
Europe, the spice is more commonly called
pimento (piment) and should not be con-
fused with pimiento or Spanish paprika. The
leaves are also aromatic and are collected
for distillation of the essential oil.
Commercial Sources
Jamaica, Mexico, Guatemala, Honduras
and Belize (in order of importance). Annual
trade is on the order of 3,000 to 4,000 tons
per year. The Mexican spice is larger than
the Jamaican, but is also inferior in quality.
The lesser quality is considered to be due
to the higher content of myrcene in the
Mexican oil (Green and Espinosa 1988).
Description
Dark reddish-brown almost globular fruit;
4-7 mm in diameter, having a rough skin
and at one end a small projection (remains
of style) surrounded by a raised ridge
(remains of calyx); opposite to this is a
circular stem scar. The fruit contains two
seeds.
Volatile Oil Content
1.3-5.3 percent. The Jamaican material is
the highest in oil content, averaging 4.1 to
5.3, followed by Grenada at 3.7 to 4.4,
Belize at 2.5 to 4.0, Honduran at 1.3 to
4.1 and Mexican at 1.4 to 2.9 (Green and
Espinosa 1988).
Sensory Character
Strongly fragrant, phenolic, reminiscent of
clove with a slightly floral backnote. The
long-held suggestion that the spice has
256 Source Book of Flavors

a nutmeg/cinnamon character is hardly TABLE 7-29. Chemical composition of pimento

justified. The flavor is strongly astringent, berry oil
warmly spicy and pungent. Compound Jamacian Mexican

Essential Oils a-pinene + a-thujene 0.27-0.52 0.15

Oil of Pimento Berry (Pimenta)-Annual myrcene 0.20-0.30 5.28
a-phellandrene 0.50-1.17
production of pimento berry oil is about 3 limonene 0.14-0.22 0.36
metric tons. Most of this oil is produced in 1,8-cineole 0.92-1.34 2.22
Jamaica (Lawrence 1985). ~-ocimene + 0.33-0.73 1.36
Specifications in EOA No. 255; FCC y-terpinene
III (1981). p-cymene 0.23-0.56 0.09
terpinolene 0.70-1.46 0.45
A colorless to reddish-yellow oil which linalool 0.15-0.16 0.27
darkens with age; specific gravity (25°C/ ~-elemene + 0.55-0.65 0.55
25°C), 1.018 to 1.048; optical rotation terpinen-4-ol
(20°C), -2° to +O.SO; refractive index isocaryophyllene + 4.25-5.39 4.04
(20°C), 1.531 to 1.54. The oil contains caryophyllene
alloaromadendrene 0.05-0.09 1.30
not less than 65 percent total phenols by a-terpineol + y-1 1.60-1.83
volume (mostly eugenol); solubility (70 ~-humulene
percent ethanol), 2 volumes sometimes with a- + ~-selinene 0.74-0.99 0.34
opalescence. y-cadinene 0.77-0.86 0.19
ar-curcumene 0.13-0.21 0.07
methyl eugenol 2.90-13.11 27.50
Oil of Pimento Leaf Approximately 30
caryophyllene oxide + 0.31-0.54
metric tons of pimento leaf oil are produced caryophyllene
worldwide. While Guatemala and Mexico aldehyde
produce small quantities of the oil, most ~-caryophyllene 0.43-0.58
(>95 percent) is produced in Jamaica alcohol
eugenol 68.75-78.23 49.12
(Lawrence 1985). chavicol 0.24-0.46 1.21
Specifications in FCC III (1981).
* not detected
A pale yellow to light brownish yellow oil
which darkens on storage; specific gravity
(25°C/25°C), 1.037 to 1.050; optical rotation
(20°C), oo to -3°; refractive index (20°C), ~-ocimene, p-cymene, terpinolene, a-
1.531 to 1.536. The oil contains 80 per- copaene, linalool, a-gurjunene, terpen-4-ol,
cent to 91 percent total phenols (mostly ~-caryophyllene, alloaromadendrene, a-
eugenol); solubility (70 percent ethanol) 2 humulene, a-selinene, a-muurolene, 0-
volumes often with opalescence. cadinen, eugenyl methyl ether, eugenol,
The odor and flavor of pimento leaf oil is iso-eugenol. A sensory assessment of the
much coarser than those of the berry oil. It effluent gas from the GLC revealed 23 trace
is used to blend with the genuine berry peaks or no detectable peaks but areas of
oil and is frequently mixed with cheaper positive aromatic response.
clove stem and leaf oils, which may have
been rectified to improve their sensory Oleoresin Pimento (Allspice)
characters. A brownish-green to dark green oily fluid
Constituents Chemical Composition of oleoresin. Two grades are available:
Pimento Berry Oil (Table 7-29) (Green and
Espinosa 1988):
Volatile Oil Content Suggested Use Rate
Pimento leaf oil contains: a-pinene, (ml per 100 g) (%)
sabinene, a-phellandrene, limonene, 1,8- 45-50 4-6
cineole, cis-~-ocimene, y-terpinene, trans- 60-66 3
 Natural Flavoring Materials 257

References: Allspice TABLE 7-30. Specifications of oil of angelica root

Green, C.L. and Espinosa, F. 1988. Jamaican and seed
and Central American Pimento (Allspice; Seed oil
Root oil
Pimenta Diocia): Characterization of flavour
differences and other distinguishing features. Appearance Pale yellow to Light yellow
In Flavors and Fragrances: A World Perspec- deep amber
tive, eds. B.M. Lawrence, B.D. Mookherjee, Sp. Gr. 0.850-0.88 0.853-0.876
andB.J. Willis, pp. 3-20. New York: Elsevier. (25°C/25°C)
Lawrence, B.M. 1985. Essential oils-World Optical oo to +46° +4° to+ 16°
production. Perfum. Flavorist 10:1-16. rotation
(20°C)
Oberdieck, R. 1989. Allspice. Fleischwirtschaft 1.4800-1.4880
RI (20°C) 1.4735-1.4870
69(3):320-330, 380. Ester value 10-65 14-13
Pino, J., Rosado, A., and Gonzalez, A. 1989. Acid value min7 min3
Analysis of the essential oil of pimento berry Solubility 1 ormorevol 4or morevol
(Pimenta dioica). Nahrung 33(8):717-720. (90% with
Salzer, U.J. 1977. The analysis of essential oils ethanol) opalescence
and extracts (oleoresins) from seasonings-A
critical review. CRC Crit. Rev. Food Sci.
Nutr. 9(4):345-373.
defined ridges of which the outer 2 form
Angelica membranous wings.
Angelica is the root and seeds of a tall
Umbelliferous plant (Angelica archangelica Volatile Oil Content
L., alternatively classified as Archangelica
officinaiis Hoffm.) indigenous to northern Root-0.3 to 1 percent
Europe. The root and seeds are little used as Seed-0.5 to 1.5 percent
a spice, but as the source of the essential oil.
The fresh stems are often crystallized and Sensory Character
colored green for use in cake decoration and Strongly penetrating, musky, earthy odor;
flavoring. In the United States, the root of flavor is bittersweet and warmly pungent.
purple stem angelica (Angelica atropurpurea The seed oil has a similar but more delicate
L.) and, in India, the root of A. glauca profile, and is sweeter than the root oil.
Edgew., are used as a source of essential
oil, but both are inferior to the genuine Oil of Angelica Root and Seed
material. Specifications in EOA No. 96 (root)
and No. 97 (seed); FCC III (1981).
Commercial Sources
Angelica seed oil and root oil are produced Constituents
in Belgium, the Netherlands, United The chemical composition of angelica root
Kingdom and Hungary. Annual production oil has been investigated by Taskinen and
was estimated at less than 400k (seed oil) Nykanen (1975) and the following con-
and about 300 k (root oil) in 1984 (Lawrence stituents reported:
1985).

Description a-pinene (24.0%)

camphene (1.3%)
sabinene (0. 76%)
Root-Short pieces, 2.5 to 5 em in length, a-phellandrene and myrcene (7.6%)
with numerous rootlets. limonene (13.2%)
Seed-Greyish-white, oval, separated cis-ocimene (1.25%)
mericarps; 6-7 mm long, having 5 well- trans-ocimene (2.68%)
terpinolene (0.16%)
258 Source Book of Flavors

caryophyllene (0.04%) presented conpositional data on tap and

~-bisabolene (0. 72%) lateral root oils of both var. sativa and
o-cadinene (0.50%) var. norvegica. The tap and lateral root oils
cuparene (0.10%)
linalool (0.01%)
differed slightly in composition. The major
trans-p-menth-2en-1-ol (0.24%) differences were in the amounts of a-
trans-verbenol (0.64%) pinene, sabinene, p-cymene, cryptone, and
cis-piperitol (0.05%) ~-bisabolene. Varities differed primarily in
0-cymen-8-ol (0.18%) the relative amounts of a-pinene, sabinene,
cuminyl alcohol (0.02%)
~-phellandrene, and p-cymene. More recent
elemol (0.18%)
bornyl acetate (0. 76%) data on composition and 13 C NMR analysis
trans-pinocarvyl acetate (0.17%) has been presented by Formacek and
bornyl isovalerate (0.07%) Kubeczka (1982).
trans-verbenyl acetate (0.17%)
tridecanolide (0.45%)
octanal (0.01%)
References: Angelica
cuminyl alcohol (0.02%) Formacek, V. and Kubeczka, K.H. 1982.
a-thujene (trace) Essential Oils Analysis by Capillary Gas
~-pinene (1.25%) Chromatography and Carbon-13 NMR
.i-3-carene (10.1%) Spectroscopy. New York: John Wiley & Sons .
a-terpinene (0.07%) Forsen, K. 1979. Aroma constituents of Angelica
~-phellandrene (10.1%) archangelica variations in the composition of
y-terpinene (0.11%) the essential oil of strains of var. norvegica
para-cymene (9.8%) and var. sativa. Rep. Kevo Subarcttic Res. Stn.
a-copaene (1.91%) 15:1-7.
germacrene D (0.26%)
Lawrence, B.M. 1976. Progress in essential oils.
a-muurolene (1.20%)
curcumene (0.06%) Angelica oils. Perfum. Flavor. 1(6):31.
trans-sabinene hydrate (0.01%) Lawrence, B.M. 1981. Progress in Essential Oils.
cis-p-menth-2-en-1-ol (0.31%) Angelica root oils. Perf. Flav. 6(3):46.
cis-verbenol (0.10%) Lawrence, B.M. 1982. Progress in Essential Oils.
a-phellandren-8-ol (0.40%) Angelica oils. Perf. Flav. 7(2):35.
trans-carveol (0.11%) Lawrence, B.M. 1985. Essential oils-World
p-cymen-8-o1 (0.31%) production. Perfum. Flavorist 10:1-16.
a-copaen-11-ol (0.46%) Saarinen, L. 1987. Separation of essential aroma
~-eudesmol (0.21%)
compounds from angelica root and fir twigs.
trans-verbenylacetate (0.46%)
Dep. of Food Chern. & Tech., Univ. of
cis-carvyl acetate (0.05%)
trans-carvyl acetate (0.03%) Helsinki, Helsinki, Finland. Thesis.
isoamyl isovalerate (0.02%) Taskinen, J. and Nykanen, L. 1975. Chemical
pentadecanolide (0.37%) composition of angelica root oil. Acta Chern.
tetradecanal (0.02%) Scand B29(7):757-764.
cryptone (0.05%) Taskinen, J. 1975a. 12-Methyl-ro-tridecanolide, a
humulene monoxide (0.41%) new macrocyclic lactone from angelica root
oil. Acta Chern. Scand. B29:637-638.
Taskinen, J. 1975b. A new sesquiterpene alcohol
Trace quantities of the following com-
of the copaene series from angelica root oil.
pounds were also reported: terpen-4-ol, Acta Chern. Scand. B29:999-1001.
trans-piperitol, heptyl isovalerate, octyl
isovalerate, heptadecanolide, nonanal,
pentadecanal, 2-decanone. Anise
Later work by Taskinen (1975a,b) re- Anise is the dried ripe fruit (incorrectly
sulted in the isolation of a new sesquiterpene called seeds) of an annual Umbelliferous
alcohol, cis-acopaen-8-ol and a new macro- plant (Pimpinella anisum L.), which is
cyclic lactone, 12-methyl-4-tridecanolide native to Egypt and the Mediterranean
in angelica root oil. Forsen (1979) has region.

Commercial Sources
France, Germany, Spain, USSR, Bulgaria,
Turkey, Cyprus, Tunisia, Mexico, India and
China.
Description: Greenish-grey to dull
yellowish-brown tapering ovoid mericarps;
2-5 mm in length; surface covered with very
short hairs and bearing ten light-colored
ridges.
Volatile Oil Content
1.5-6 percent.
Fixed Oil Content
About 20 percent.
Sensory Character
Characteristically anisic, sweetly aromatic
odor and flavor.
Oil of Anise (Aniseed)
Spain (6 tons) and Egypt (1 ton) are the
major manufacturers of aniseed oil. It is
estimated that worldwide production of
this oil was about 8 metric tons in 1984
(Lawrence 1985).
Specifications in FCC III (1981).
A colorless to faintly yellow oil which, on
cooling to about 15° -19°C, solidifies due to
the crystallization of anethole.
Specific gravity (25°C/25°C), 0.980 to
0.990; optical rotation (20°C), oo to -2° but
FCC permits + 1o; refractive index (20°C),
1.552 to 1.560; solubility (90 percent
ethanol) 1.5 to 3 vol. The congealing point
should lie between 15° and 19°C.
Constituents The composition of anise
oil of Turkish origin has been reported by
Tabacchi et al. (1974) and commercial oils
by Embong et al. (1977) and Lawrence
(1980). Formacek and Kubeczka (1982)
have presented data on composition and 13C
NMR analysis of anise oil. The results of
Lawrence (1980a) are presented below:
a-pinene (0.17 percent)
camphene (0.07 percent)
~-pinene (0.01 percent)
sabinene (0.01 percent)
myrcene (0.02 percent)
Natural Flavoring Materials 259
ii- 3-carene (trace)
a-phellandrene (0.09 percent)
a-terpinene (0.02 percent)
~-phellandrene +
1,8-cineo1e (0.06 percent)
cis-ocimene (0.02 percent)
trans-ocimene + acetoanisole (0.94 percent)
y-terpinene (0.01 percent)
p-cymene (0.08 percent)
terpinolene (trace)
linalool (0.18 percent)
terpinen-4-ol (trace)
a-terpineneol (0.12 percent)
methyl chavicol (1.02 percent)
trans-~-farnesene (trace)
cis-anethole (2.29 percent)
trans-anethole (85.00 percent)
safrole (0.58 percent)
anisaldehyde (0. 91 percent)
The fact that the cis-anethol content was
circa 2.3 percent and not the usual 0.2-0.4
percent indicates that the oil was prob-
ably diluted with a coupage containing
synthetic anethole, acetoanisole and possibly
anisaldehyde. The reason for this deduction
is that synthetic anethole contains 2-3 per-
cent of cis-anethole (Lawrence 1980a).
Oleoresin Anise
Description a yellowish-green to
orange-brown fluid oleoresin.
Volatile oil content 15 to 18 ml per
lOOg.
Suggested use rate 7.5 to 9 percent.
The presence of a large quantity of fixed
oil in this product limits its shelf life and
the addition of a permitted antioxidant is
advised.
References: Anise
Embong, M.B., Hadziyev, D., and Molnar, S.
1977. Essential oils from spices grown in
Alberta. Anise oil (Pimpinella anisum). Can.
1. Plant Sci. 57(3):681-688.
Formacek, V. and Kubeczka, K.-H. 1982.
Essential Oils Analysis by Capillary Gas
Chromatography and Carbon-13 NMR
Spectroscopy. New York: John Wiley & Sons.
Lawrence, B.M. 1980a. Progress in Essential
Oils. Anise oil. Perf. Flav. 8(3):65.
Lawrence, B.M. 1980b. Progress in Essential
Oils. Anise oil. Perf. Flav. 8(4):63.
260 Source Book of Flavors
Lawrence, B.M. 1976. Progress in essential oils.
Anise. (A monthly review). Perfum. Flav.
1(4):31; 2(3):56.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Shukla, H.S. and Tripathi, S.C. 1987. Anti-
fungal substance in the essential oil of anise
(Pimpinella anisum L.). Agric. Bio. Chern.
51(7): 1991-1993.
Tabacchi, R., Garnero, J., and Buil, P. 1974.
Contribution to the study of composition of
the essential oil of Turkish anise. Riv. /tal.
Essenze Profumi Pianti Off. 56:683-697.
(French)
Anise, China Star
Star anise is the dried fruit of a tall ever-
green tree (Illicium verum Hook.) that
is native to southern China and northern
Vietnam. Although some of the spice is
available on the market, most is used as a
source of the essential oil; in some provinces
the leaves and young stems are also dis-
tilled, but these give an inferior essential oil.
Commercial Sources
Southern China, North Vietnam, Hainan.
Description
The fruit is star-shaped and consists of eight
carpels joined centrally. The central column
is attached to a short thick stem. The dark
reddish-brown carpels are up to 20 mm long,
are boat-shaped and often irregularly devel-
oped; being brittle, they readily break apart
so that many fruits are incomplete. Each
carpel contains a single shiny, hard, light-
brown seed.
Volatile Oil Content
2.5 to 3.5 percent on fresh fruit; 8-9 percent
on dried material. Fixed oil content: about
20 percent.
Sensory Character
Characteristically anisic, sweetly aromatic
odor. The profile of star anise oil is similar
to that of the Pimpinella oil, and the two are
equally acceptable and interchangeable in
use.
Oil of Star Anise
Sources The major producing countries
for star anise oil (also known as Badiane oil)
are China (70 tons) and Vietnam (15 tons).
Total worldwide production of this oil was
estimated at between 85 and 90 metric tons
in 1984 (Lawrence 1985).
Specification in FCC III (1981). A
colorless to pale yellow oil which crystallizes
to a solid mass on cooling to about 15° to
19°C; specific gravity (25°C/25°C), 0.980 to
0.990; optical rotation (20°C), oo to -2°;
refractive index (20°C), 1.553 to 1.557;
solubility (90 percent ethanol), 1.5 to 3 vol.
The congealing point should lie between 15°
and 19°C.
Constituents
Recent work has been reviewed by Cu
et al. (1988) and is presented in Table 7-31.
References: Anise, China Star
Cu, J.Q., Perineau, F., and Goepfert, G. 1990.
GC/MS analysis of star anise oil. J. Essent. Oil
Res. 2(2):91-92.
Formacek, V. and Kubeczka, K.H. 1982.
Essential Oils Analysis by Capillary Gas
Chromatography and Carbon-13 NMR
Spectroscopy. New York: John Wiley & Sons.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Martin, G.J., Janvier, P., and Mabon, F. 1985.
Deuterium NMR identification of anetholes
[in star anise]. A factor analysis study of Site-
specific Natural Isotope Fractionation (SNIF-
NMR). Analusis 13(6):267-274.
Balm (Lemon Balm)
Balm is the dried and broken flowering tops
and leaves of a herbaceous plant (Melissa
officina/is L.), which grows wild and is
cultivated in Europe and parts of North
America.
Commercial Sources
France, Italy and Morocco.
Volatile Oil Content
About 0.1 percent on the freshly harvested
herb (Furia and Bellanca 1975).
 Natural Flavoring Materials 261

TABLE 7-31. Constituents of oil of star anise

Compound Yunnan Chinese Vietnam

a-pinene 0.57 2.07 0.62

~-pinene 0.05 0.22 0.05
sabinene 0.05 0.24
o-3-carene 0.34 0.93 0.24
myrcene 0.12 0.40 0.08
a-phellandrene 0.08 0.48 0.44
p-cymene 0.18 0.20 0.11
limonene + 1,8-cineole 2.98 10.44 0.68
linalool 0.42 1.03 2.34
terpinen-4-ol 0.38
a-terpineol 0.11 0.23 0.20
methyl chavicol 0.34 0.56 6.65
cis-anethole 0.42 0.11 0.39
anisaldehyde 4.48 0.38 0.62
trans-anethole 85.46 79.93 86.06
copaene 0.04 *
anise ketone 1.02 *
caryophyllene 0.11 0.38 0.46
trans-~-bergamotene 0.14 *
cis-a-famesene 0.09 *
trans-~-famesene 0.08
trans-methyl isoeugenol 0.06
~-bisabolene 0.05
nerolidol 0.12
methyl anisate 0.09
feniculin 0.5
* Not detected

Sensory character resultant sensory properties. The different

Pleasantly citrus, lemony odor with an
aromatic and slightly bitter taste.
References: Balm
Furia, T.E. and Bellanca, N. 1975. Fenaroli's
Handbook of Flavor Ingredients, 2nd Edition,
Vol. 1 and 2. Cleveland: C.R.C. Press.
types of oils are discussed by Lawrence
(1988), and Gulati and Sinha (1989). A very
simplified classification is presented below:
Sweet basil (European type)-Cultivated in
southern France, Italy, Hungary, Belgium,
Spain and Poland as well as in the United
States.

Basil, Sweet Exotic basil (Reunion type)-Cultivated in

Sweet basil is the dried and broken flower-
ing tops and leaves of a herbaceous plant
( Ocimum basilicum L.), which is native to
India and Iran but is now widely cultivated
in southern Europe and in the United States
(California). There are some 150 species of
Ocimum, which readily hybridize so that
basil exists in several distinct varieties and
closely related species. This results in a
wide variety of types of essential oils which
may be very different in composition and
the Comoro Islands, the Seychelles and in
the Malagasy Republic.
Two other species of basil, used locally
but of minor commercial interest, are also
recognized:
Bulgarian basil (methyl cinnamate type),
possibly derived from Ocimum canum
Simms (Guenther 1948-1952), which
grows in West Africa, the East Indies and
Indonesia.
262 Source Book of Flavors

Java basil (eugenol type) from Ocimum
gratissimum L., which grows in Java and the
Pacific Islands.
Description
The fresh herb is a small erect plant growing
to 15-50cm high; the ovate green leaves are
opposite and have a slightly serrated margin.
The clusters of flowers are small, white to
purple, and appear from May to September.
In the United States (California), the com-
mercial product is harvested, the leaves and
flowering tops carefully dried under con-
trolled conditions to retain their full color
and aroma prior to being broken and
screened to the desired particle size. In
Europe, the cut herb is normally sun dried
and may result in a less aromatic and
browner product.
The dried rubbed herb is brownish-green
in color and consists of a mass of brittle,
curled and folded leaves together with
broken leaves and floral parts.
Volatile Oil Content
1.5-3 percent.
Sensory Character
The aromatic profiles of the different vari-
eties make them readily distinguishable-
the European type is sweetly floral, linalool-
like with an anisic back-note; the Exotic
type has a distinctive camphoraceous and
strongly anisic character (Heath 1978).

TABLE 7-32. Constituents of Ocimum basilicum

o. basilicum o. basilicum var. minimum

Compound Leaf Stem Flower Leaf Stem Flower

a-pinene 0.28 0.35 0.21 0.22 0.51 0.43

camphene 0.01 0.01 0.01 0.04
~-pinene 1.18 0.06 0.30 0.27 0.30 0.65
sabinene 0.33 0.35 0.20 0.01 0.12 0.28
myrcene 1.17 0.37 0.24 0.57 0.74 0.91
a-terpinene 0.04 0.18 0.04 0.01 0.03
limonene 0.69 0.15 0.93 0.46 0.54 0.41
~-phellandrene 0.10 0.44 0.04 0.01
1,8-cineole 8.05 11.20 2.59 2.00 0.77 4.03
y-terpinene 0.37 0.80 1.57 0.18 0.04 0.12
ocimene 4.02 0.07 2.88 1.56 0.96 4.22
p-cymene O.Q7 0.06 0.07 0.01 0.10
terpinolene 0.09 0.09 0.04 0.03
citronella! 0.01 0.01 0.04 0.15
linalool 6.78 1.60 24.63 0.74 0.84 1.47
methyl thymol 0.44 0.15 0.27 0.14 0.22
caryophyllene 6.06 7.18 6.20 5.85 12.22 9.92
terpinen-4-ol 0.62
methyl chavicol 35.03 4.91 41.80 17.72 9.02 27.69
citronellyl
acetate 0.14 0.34 0.31 O.Q7 0.20 0.02
neral 0.30 0.02 0.13 0.35 0.80 0.43
a-terpineol 0.12 0.05 0.15 0.15 0.45 0.02
a-terpinyl acetate 1.15 8.16 2.34 1.12 2.94 2.77
geranial 0.72 1.66 0.88 0.88 2.89 0.70
citronellol 0.05 0.17
nero! 0.02 0.01 0.10
geraniol 0.01 0.02 O.Q7
methyl eugenol 30.53 3.36 4.48 64.25 52.23 42.90
eugenol 0.35 53.08 5.91 0.44 3.54
 Natural Flavoring Materials 263

TABLE 7-33. Major components of various Ocimum basilicum

Chemotypes"

Compound (Ia) (lb) 2(a) 2(b) 3(a) 4(a)

1,8-cineole 3.2 4.6 1.4 2.7 2.4 3.4
cis-ocimene 0.1 0.3 0.2 0.1 trace trace
trans-ocimene 0.6 5.4 1.0 2.2 0.4 trace
camphor 0.2 1.8 0.3 4.3 0.9 1.8
linalool 0.5 4.8 83.9 51.6 0.6 6.2
methyl chavicol 85.3 49.0 0.4 0.7 1.5 5.0
geraniol trace trace 0.3 22.8 trace trace
methyl eugenol 1.9 19.2 trace trace 67.7 0.3
trans-methyl cinnamate trace trace trace trace 0.3 64.0
eugenol trace 0.2 0.5 trace 2.0 trace
"Chemotypes of Ocimum basilicum with a single biosynthetic pathway:
Type 1. (a) methyl chavicol-rich
(b) methyl chavicol > methyl eugenol
Type 2. (a) linalool-rich
(b) linalool > geraniol
Type 3. (a) methyl eugenol-rich
Type 4. (a) methyl cinamate-rich

Essential Oils Odor harshly camphoraceous, heavy,

Basil oils are produced primarily in the spicy, phenolic.
Comores (6 tons), Madagascar (2 tons), Constituents Chemical composition of
USA (1 ton), Albania (1 ton) and Egypt (1 leaf, stem and flower oils of Ocimum basili-
ton). Lesser quantities are produced in a cum (Table 7-32).
number of other countries. It is estimated One must note that there is a wide varia-
that worldwide production in 1984 was tion in basil oil, depending on the source of
about 14 metric tons (Lawrence 1985). the starting material. This is very evident
from the table below.
Oil of Sweet Basil (European Type) Major components of various Ocimum
Specifications in FCC III (1981). A basilicum selections (single biosynthetic
pale yellow to greenish-amber oil; specific pathways) (Table 7-33).
gravity (25 C/25 C), 0.90 to 0.920; optical
rotation (20°C), -5 to -15°; refractive Oleoresin Basil
index (20°C), 1.483 to 1.493; ester value is A dark green pasty to semifluid oleoresin.
about 10 and the ester value after formyla- Two grades are available (Table 7-34).
tion 140 to 180. Odor: Sweetly anisic,
cooling, floral. References: Basil, Sweet
Oil of Exotic Basil (Reunion Type) Chittenden, F.J. and Synge, P.M. 1951.
Specifications in EOA No. 120; FCC Dictionary of Gardening, A Practical
III (1981). A light yellow oil; specific gravity
(25°C/25°C), 0.952 to 0.973; optical rota- TABLE 7-34. The two grades of oleoresin basil
tion (20°C) -2 to +2°; refractive index
Volatile Oil Suggested Volatile Oil
(20°C) 1.512 to 1.519; acid value, max 1; Content Use Rate in Dispersion
saponification value, 4 to 10; ester value (ml/100 g) (%) (%)
(after acetylation), 25 to 45; solubility (80
percent ethanol), 4 vol, (propylene glycol), 40 2 0.8
42-48 0.42-0.48
20 vol.
264 Source Book of Flavors
Encyclopaedia of Horticulture. Oxford: The
Clarenden Press.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
Gulati, B. and Sinha, G.K. 1989. Studies on
Some Important Species of Ocimum. In
Essential Oils, Fragrances and Flavours, Vol.
4 Chemistry, Analysis and Structure, eds.
S.C. Bhattacharyya, N. Sen and K.L. Sethi.
New Delhi: Oxford & IBH Publishing Co.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn.:
AVI Publishing Co.
Lawrence, B.M., Hogg, J.W., and Harney, P.M.
1972. Essential oils and their constituents. IX.
The oils of Ocimum sanctum and 0. basilicum
from Thailand. Flavour Ind. 3:47-49.
Lawrence, B.M. 1978. Progress in essential oils.
Basil. Perfum. Flav. 3(5):36-38.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Lawrence, B.M. 1988. A further examination of
the variation of Ocinum basilicum L. In
Flavors and Fragrances: A World Perspective,
eds. B.M. Lawrence, B.D. Mookherjee, and
B.J. Willis. New York: Elsevier.
Mairapetyan, S. 1979. Productivity and quality of
the essential oil of ordinary basil grown under
open-air hydroponic conditions. Bioi. Zh.
Arm. 32:691.
Purohit, P.V. and Khanna, P. 1983. Production
of essential oil from callus cultures of ocimum
basilicum L. Basic Life Sci. 22:377.
Bay Laurel, Sweet Bay
Sweet bay laurel is the dried leaves of
an evergreen tree (Laurus nobilis L.),
which grows throughout the Mediterranean
region. The black ovoid fruits are some-
times used in nonalcoholic beverages. There
is no relationship between the leaves of
sweet bay laurel and those of cherry laurel
( Prunus laurocerasus L.), which contain
hydrocyanic acid, smell strongly of bitter
almond and are, in consequence, poisonous;
nor with those of West Indian bay (Pimenta
racemosa Mill.), which have a strong clove-
like aroma when crushed.
Commercial Sources
Italy, Turkey, Cyprus, Yugoslavia,
Morocco, Greece, France, Spain, China and
the former Soviet Union.
Description
Dark green to brownish-green, smooth
surfaced leaves, elliptical-lanceolate in
shape of variable size but averaging between
8-10 em long and 2-3 em wide. They are
pointed at both ends and have a short stalk.
The margin is never entirely serrated.
The fresh leaf is characteristically fragrant
when crushed but dried-out leaves lack this
character.
Volatile Oil Content
0.5 to 3 percent.
Sensory Character
Sweetly aromatic, camphoraceous, cineolic
odor and a sweetly spicy flavor.
Oil of Sweet Bay (Laurel Leaf)
Laurel leaf oil is produced in a number
of countries, including Yugoslavia, Italy,
Turkey, Portugal, Morocco, the USSR and
Albania. However, significant quantities are
produced only in the USSR (2 tons) and
Albania (1 ton). Worldwide production
was estimated to be 4 metric tons in 1984
(Lawrence 1985).
Specification in EOA No. 119; FCC III
(1981). A light yellow to yellow oil; specific
gravity (25°C/25°C), 0.905 to 0.929; optical
rotation (20°C), -10 to -19°; refractive
index (20°C), 1.465 to 1.470; acid value,
max. 30; saponification value, 15 to 45;
solubility (80 percent ethanol), 1 vol.
Constituents Chow et al. (1965) studied
the terpenes present in sweet bay oil;
Teisseire (1966) reported the composition
as: terpenes (22 percent), linalool (8-11
percent), and 1,8-cineole (35 percent).
Skrubis (1972) reported on an oil of Greek
origin and Buttery et al. (1974) examined a
laboratory distilled oil and found:
a-pinene (12%) camphene (2%)
~-pinene (6%) sabinene (5%)
myrcene (1%) a-phellandrene (0.5%)
 Natural Flavoring Materials 265

a-terpinene (0.5%) limonene (4%) odor properties. J. Agric. Food Chern. 22:
y-terpinene (1%) p-cymene (2%) 773-777.
terpinolene (0.3%) 1,8-cineole (30%) Chow, P.N., Mot!, 0., and Lukes, V. 1965. On
linalool (11%) terpinen-4-ol (3%) terpenes. Ch. XXII. Hydrocarbons from the
a-terpineol (6%) a-terpinyl acetate (10%)
methyl eugenol (4%) oil of laurel leaves. Coli. Czech. Chern.
eugenol (2%)
Commun. 30:917-919.
Heath, H. 1973. Herbs and spices-a bib-
liography. I & II. Flav. Ind. 4(1):24-26;
Hogg et a!. (1974) isolated and identified
4(2):65-69.
dehydro-1 ,8-cineole as present. The most Hogg, J.W., Terhune, S.J., and Lawrence,
recent investgation was by Zola and Garnero B.M. 1974. Dehydro-1-8-cineole: A new
(1977), who compared the composition of monoterpene oxide in Laurus nobilis oil.
oils from Yugoslavia, Morocco, Spain and Phytochemistry 13:868-869.
France, demonstrating the following range Lawrence, B.M. 1978. Progress in essential oils.
of figures: terpenes (16-26 percent), 1,8- Bay laurel. (A monthly review). Perfum.
cineole (37.2-44.1 percent), terpinen-4-ol Flavor. 2(5):46-48.
(2.38-4.6 percent), a-terpineol (1.6-4.61 Lawrence, B.M. 1985. Essential oils-World
percent), a-terpinyl acetate (6.11-10 production. Perfum. Flavorist 10:1-16.
percent), and eugenol, methyl eugenol and Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
acetoeugenol together (2.13-9.78 percent).
oils from seasonings. I, II & III. Int. Flavours
Lawrence (1978) has tabulated the detailed
Food Additives 6:151-157; 6:206-210; 6:
results. 253-258.
Skrubis, B.G. 1972. Seven wild aromatic plants
Oleoresin Sweet Bay (Laurel) growing in Greece and their essential oils.
A dark olive-green semifluid oleoresin. The Flavour Ind. 3:566-568.
following grades are available (Table 7-35). Teisseire, P. 1966. Contribution to the knowl-
The GC evaluation of the essential oil edge of essential oil of noble laurel leaf.
recovered from oleoresin bay laurel has Recherches 15:85-86.
been reported by Salzer (1975). The con- Zola, A. and Garnero, T. 1977. The essential oil
tent of 1,8-cineole, a-terpinyl acetate of noble laurel. Riv. /tal. Essenze Profumi
and eugenol derivatives were chosen as a Pianti Off. 59:374-378. (French)
measure of flavor quality.
Bay, Westlndian
Rererences: Bay Laurel West Indian bay is a shrub (Pimenta
Akguel, A., Kivanc, M., and Bayrak, A. 1989. racemosa (Mill.) J.W. Moore also classi-
Chemical composition and antimicrobial fied as Pimenta acris Kostel), which is
effect of Turkish laurel leaf oil. J. Essent. Oil indigenous to this region.
Res. 1(6):277-280.
Buttery, R.G., Black, D.R., Guadagni, D.G., Commercial Sources
Ling, L., Connolly, G., and Teranishi, R. Dominica, Puerto Rico, St. Thomas and
1974. Californian bay oil. I. Constituents, several other of the Caribbean islands. The
leaves are not a normal article of the spice
TABLE 7-35. The grades of oleoresin sweet bay trade, and are gathered and distilled locally
Volatile Oil for their essential oil.
Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%) Volatile Oil Content
1 to 3 percent.
15-20 15-18 2.25-3.6
25-30 12-15 3-4.5 Oil of Bay, West Indian
32-36 3 0.96-1.08
72-80 1.5 1.08-1.2
A total of 18 metric tons of bay oil was
estimated to have been produced in 1984.
266 Source Book of Flavors

Dominica produced over 90 percent of this Rererences: Bay, West Indian

oil (Lawrence 1985). Analytical Methods Committee. 1975. Applica-
Specification in: EOA No. 251; FCC tion of gas-liquid chromatography to the
III (1981). analysis of essential oils. Part IV. Deter-
A yellow to dark-brown oil; specific mination of eugenol in oil of bay (Pzrnenta
gravity (25°C/25°C), 0.950 to 0.990; optical racernosa Mill.). Analyst 100:593-600.
rotation (20°C), 0 to -3°; refractive index Buttery, R. 1974. California Bay oil. I. Con-
stituents, odor properties. II. Biological
(20°C), 1.507 to 1.516. The oil should con-
effects of constituents. J. Agric. Food Chern.
tain between 50 and 65 percent of phenols 22:793.
by volume; solubility (90 percent ethanol) 1 Buttery, R.G., Black, D.R., Guadagni, D.G.,
vol sometimes with slight opalescence. Ling, L.C., Connolly, G., and Teranishi, R.
1974. California bay oil. I. Constituents, odor
Odor properties. J. Agric. Food Chern. 22(5):
Harshly aromatic and sharply penetrating. 773-777.
Lawrence, B.M. 1977. Progress in essential oils.
Constituents Bay, West Indian. Perfurn. Flavor. 1(1):3;
Lawrence (1982) has reviewed the literature 2( 4):36.
on West Indian Bay oil. He has summarized Lawrence, B.M. 1980. Progress in Essential Oils.
Bay Oil. Perf. Flav. 5(2):33-34.
the work of Peyron (1980), who identified
Lawrence, B.M. 1982. Progress in Essential Oil.
the following components: West Indian Bay Oil. Perf. Flav. 7( 4):41-49.
Lawrence, B.M. 1985. Essential oils-World
a-pinene (0.1-0.3%) production. Perfurn. Flavorist 10:1-16.
~-pinene (0.1%) Peyron, L., Acchiardi, J., Bignotti, D., and
a-phellandrene (0.4%) Pellerin, P. 1980. Baies de Pimenta dioca.
1,8-cineole (0.2-2.0%) VI/I International Congress of Essential Oils.
trans-~-ocimene (0.4-2.1%) Paper No. 128.
p-cymene (0.1-0.5%)
methyl heptenone (0.7%)
copaene (0.2%) Black Cumin
linalool (1.7-3.0%) The dried seeds of the annual plant (Nigella
caryophyllene (0.9%) satiua L.), which is a member of the butter-
neral (0.5%) cup family and not botanically related to
methyl chavicol (0.3%)
eugenol (38- 75%)
genuine cumin ( Cuminum cyminum).
sabinene (0.3%)
myrcene (13.9-31.6%) Commercial Source
limonene (1.4%) India.
~-phellandrene (0.1%)
3,octanone (1.0-1.1%)
terpinolene (0.1-0.3%)
Description
3-octanol (0.5-0.6%) Small dull black, angular, wedge-shaped
1-octen-3-ol (1.0-1.3%) seeds; 2-3mm long and having a rough
terpinen-4-ol (0.3%) surface.
a-amorphene (0.1%)
a-terpineol (0.1-0.8%)
geranyl acetate (0.8%)
Volatile Oil Content
chavicol (11-21%) 0.5 to 1.5 percent.

Some samples of West Indian bay oil
contain phenols in excess of 65 percent; such
oils are suspect and may have been mixed
with oils of clove leaf or stem.
Sensory Character
Strongly characteristic and disagreeable
odor, somewhat reminiscent of naphthalene
and to some slightly fennel-like. The flavor
is sharp and acrid.

Black Mustard
See Mustard, Black.
Black Pepper
See Pepper, Black and White.
Canella (White Cinnamon)
Canella is the bark of an evergreen tree
(Canella winterana Gaertn.), which is native
to Florida and the West Indies.
Commercial Source
Bahamas, Jamaica, Cuba.
Description
Simple quills or cut bark pieces of variable
size; light buff-colored, the outer surface
being roughly scarred, the inner surface
having longitudinal striations and often pale
to white patches.
Volatile Oil Content
About 1 percent, but the bark is not distilled
commercially.
Sensory Character
Pleasantly aromatic, the odor being remi-
niscent of allspice; the flavor is distinctly
pungent and too bitter for normal use as a
spice.
Constituents
The essential oil contains: eugenol, cineole,
a-pinene and caryophyllene.
References: Canella
Adams, R.P. and Zanoni, T.A. 1990. Essential
oils of plants from Hispaniola. III. The leaf
oil of Canella winterana (Canellaceae).
J. Essential Oil Res. 2(4):163-165.
Sherif, M.K., Awadallah, R.M., and Amrallah,
A.H. 1980. Determination of trace elements
of Egyptian crops by neutron activation
analysis. III. Trace elements in African tea,
ginger, canella bark, black pepper, sesame,
lady's fingers, jew's mallow, tomatoes,
cucumber and marrow. J. Radioanalyt. Chern.
57(1):53-60.
Natural Flavoring Materials 267
Caper
Capers are the flower buds of a shrub
(Capparis spinosa L.) found in the Medi-
terranean region and parts of southern Asia.
As available commercially, capers are
normally pickled in a vinegar or vinegar/salt
solution. The unripe seeds of the garden
nasturtium (Tropaeoleum majus L.) are
sometimes used as an alternative, but these
are more sharply pungent and do not have
the characteristic flavor of capers.
References: Caper
Castro, Ramos-R-de and Nosti-Vega, M. 1987.
The caper (Capparis spinosa L. ). Grasas-y-
Aceites 38(3):183-186.
Bremness, L. 1988. The Complete Book of
Herbs. New York: Viking Studio.
Capsicum
(Note: Paprika is also a capsicum, but will
be described under a separate heading).
Capsicums, known under innumerable
names both commercially and in domestic
use, are the fruits of the genus Capsicum,
which is indigenous to Central and South
America and the West Indies, but is now
cultivated in many of the warmer regions of
the world. They are in the same natural
order (Solanaceae) as potatoes, tomatoes
and eggplant. Capsicums are derived from
three main species, namely:
Capsicum annuum L.
C. minimum Mill.
C. frutescens L.
There is much confusion and far from total
agreement on their botanical classification.
The fruits vary considerably in size, shape,
color and pungency, depending more upon
environmental conditions and the devel-
opment of varietal cultivars than on any
specific botanical differences.
The large fleshy fruits, which are more or
less devoid of pungency, are eaten more as a
vegetable or as a source of an interesting
flavor than as a spice. These are derived
from C annuum var. grossum Sendt. They
are a rich source of vitamin C.
 268 Source Book of Flavors

Irrespective of their size and shape,
capsicums are berries having 2 to 4 ovular
cavities divided by a white fleshy septum
which is joined at one end. The numerous
seeds, which are 2-4 mm in diameter
and are discoid, are either free within the
cavity or attached to the central septum or
placenta. The seeds account for about 50
percent of the weight of the fruit.
Capsicums most used as spice are all
more or less pungent and cannot be judged
by their appearance, although the larger
fruits are generally less pungent than the
very small varieties. They differ consider-
ably in size from as small as 5 mm up to
15 em in length and from 2 mm to 7 em at
their widest part. The pods are roughly
conical according to variety, with a blunt
base and a pointed apex; some have a short
stalk or peduncle attached. Some varieties
are almost globular in shape. The color may
vary from deep brownish-red, through
bright scarlet, and yellow to dirty greenish-
yellow. The pericarp of the freshly har-
vested pods is usually smooth and shiny, but
the dried fruits are laterally compressed and
often have a deeply wrinkled skin. The odor
is generally characteristic and pleasant,
particularly in the sweet varieties, although
the more pungent types are acrid and
sternutatory. The taste ranges from mild
to intensely pungent and burning. The
varieties of commercial interest in the spice
trade are listed in Table 7-36.
Govindarajan and coworkers (1985,
1986a,b, 1987, 1991) have published ex-
ceedingly comprehensive reviews of the
Capsicums. These reviews have covered the
history, botany, cultivation and primary
processing (Part 1), processed products,
standards, world production and trade (Part
2), chemistry, of the color, aroma, and
pungency stimuli (Part 3), evaluation and
quality (Part 4), and impact on physiology,
pharmacology, nutrition, and metabolism;
structure, pungency, pain and desensitiza-
tion sequences (Part 5).
Types of Capsicum
Barbecue Spice Barbecue spice is
a variation of chili powder. Ground or
crushed red pepper comes from capsicum
grown in the Carolinas, California, Louisiana
and Turkey.
Crushed red pepper is an ingredient
in many Mexican and Italian dishes. It is
often called "pepperonirosso" or "pizza
peppers."

TABLE 7-36. Capsicum varieties of commercial interest

Capsaicin
Common Name and Content
Botanical Source Description (Mathew et al. 1971B)
African chillies Brown-red pods mixed with yellowish to dirty Very pungent;
(C. frutescens) greenish yellow pods; 8-15 mm long, 3-6 mm 0.8-0.85%,
Mombasa wide; shiny to dull wrinkled pericarp; often very some samples
dusty and sternutatory. up to 1%.
Nigerian Bright red tapering pods; 1.2-3.5 em long, Pungent, 0.6%
4-6 mm wide; shiny wrinkled pericarp.
Cayenne pepper Dark to bright red tapering pods with blunt apex; Pungent
(C. fru tescens or 2-6 em long, 10-15 mm wide; shiny wrinkled
C. boccatum) pericarp; yellow seeds.
Japanese Hontaka Orange-red to dark red tapering pods; compressed; Pungent, 0.33%
2.5-5 em long, 7-15 mm wide. Shiny wrinkled
pericarp.
Louisiana Sport pepper Deep red to orange tapering pods; 2.5-6 em long;
smooth bright, shiny pericarp.
Mexican ancho Maroon tapering, flattened pods; 9-11 em long, Very pungent
6-7 em wide, shiny wrinkled pericarp; short
curved peduncle.
Tabasco Bright red, small, clean, conical fruits; 2.5-5 em Very pungent
long; smooth, shiny pericarp; yellow seeds.

Cayenne Pepper The name Cayenne
derives from a municipality in French
Guiana, on the northern coast of South
America. Cayenne pepper (Capsicum
frutescens, C. baccatum, and other species
of capsicum) is cultivated in the tropical
parts of South America, Central America,
Africa, India and Japan. The color is dark to
bright red, the color of the seeds yellow.
Normally, they are dried shiny pods, flat,
and wrinkled. The aroma is characteristic
and pleasant. The taste is sharp, biting and
pungent. There is no volatile oil in cayenne.
The seeds are acrid and pungent. Ground
cayenne pepper is very irritating. The
pungency factor enables the hot peppers to
be used partially as replacement for black
pepper. The principal uses are in frank-
furters, bologna, Mexican sausage, smoked
country sausages, and in sausages which are
marketed in the South. It is also used as
flavoring for meat, fish and sauces.
Pimiento Among the other capsicum
varieties is pimiento, not to be confused
with pimento or allspice. It is principally
used for spot color purposes in meat loaves
and in certain national specialties. Pimiento,
Pimienton, or Spanish paprika has the
characteristics of that grown in Spain.
Chili Pepper and Chillies Chili pepper
is produced in large quantities in California.
It resembles paprika. Chili pepper or chillies
is a small whole red, very pungent, dried
ripe capsicum fruit. Tabasco chillies are
small, extremely pungent peppers used in
making cayenne pepper for pickling pur-
poses and in the manufacture of tabasco
sauce. The principal use of chili pepper is as
an ingredient of chili powder.
Volatile Oil and Extractives
Capsicums do not contain any volatile oil,
but yield 20 to 30 percent of extractive in 60
percent ethanol and about 10 percent in
acetone. Most specifications require not less
than 15 percent of nonvolatile ether extract.
It contains 4 to 16 percent of fixed oil,
depending on the percentage of seeds
present in the sample.
Natural Flavoring Materials 269
Constituents
Capsicums have three main attributes:
Aroma Although used primarily for
their pungent effect, capsicums do have a
distinctive aroma that is particularly pleasing
in the sweet varieties. The aromatic con-
stituents have been investigated by Buttery
et al. (1969) and by Hayman and Aurand
(1971). The following compounds have
been identified in tabasco pepper: 3-methyl-
1-pentanol, n-hexanol, cis-3-hexanol, meth-
yl salicylate, 3-methyl-1-pentyl-2-methyl
butyrate, 3-methyl-1-pentyl-3-methyl buty-
rate, 4-methyl-1-pentyl-3-methyl butyrate,
4-methyl-1-pentyl-n-valerate, n-hexyl-3-
methyl butyrate, n-hexyl, n-valerate, iso-
amyl isovalerate, 4-methyl-1-pentyl isobuy-
rate, 4-methyl-1-pentyl-4-methyl valerate,
4-methyl-1-pentyl-n-caproate and benzal-
dehyde.
The bell pepper aroma is characterized by
2-methoxy-3-alkylpyrazines (Seifert 1970)
and by 4,5-dialkylthiazoles (Buttery et al.
1976). The significance of volatiles to the
aroma of various capsicums has been re-
viewed by Govindarajan, Rajalakshmi and
Chand (1986).
Pungency The pungent component
of capsicums is due to seven homologous
branched-chain alkyl vanillylamides called
capsaicinoids (Fig. 7-10). Three additional
straight-chain analogs have also been
identified, but are considered to contribute
little to the pungency of the capsaicins
(Govindarajan, Rajalakshmi and Chand,
1986).
In the traded capsicums (C. annuum var.
annuum), capsaicin generally comprises
between 33 and 59 percent of the capsaic-
inoids with dihydro-capsaicin between
30 and 51 percent, nordihydro-capsaicin
between 7 and 15 percent and the remainder
less than 5 percent. The fruits from C.
frutescens have a greater proportion of the
two primary capsaicinoids (capsaicin and
dihydro-capsaicin, totally 77-90 percent)
and less of the other homologs. The total
amount of capsaicinoids present in the
capsicums varies greatly depending upon
 270 Source Book of Flavors

H,C"'Off= JlR
HO

R Name Abb. Mol.wt.

Branched, unsaturated

~ Capsaicin c 305

Homocapsaicin I HCI 319

~
~ Homocapsaicin II HC II 319

Branched, saturated
Nord ihydrocapsaicin I NOC I 293

~ Nordihydrocapsa icin II NOCII 293

~ Oihydrocapsaicin DC 307

~ Homodihydrocapsa icin I HOCI 321

~ Homodihydrocaps aicin II HOC II 321

Saturated, analogs
~ Octoyl N- vanillylamide ov 279

~ Nonoyl N- vanillylamide NV 293

~
Decrl N-vanillylamide ov 307

FIGURE 7-10. Capsaicinoids-capsaicin, homologs and analogs. (Govindarajan et

a!. 1987)

the member of the family. There is from
0.001 to 0.01 percent in paprika to 0.1 to > 1
percent in the chillies (Govindarajan,
Rajalakshmi and Chand, 1986).
The relative pungency of the capsaici-
noids was first studied by Nelson (1919),
and he noted that capsaicin and dihydro-
capsaicin are about equal in pungency with
the other capsaicinoids being much less
pungent.
Pure capsaicin is a white crystalline
compound that melts at 65°C and is volatile
above this temperature. It produces a
dangerously irritating vapor (Mathew et al.
1971b).
Color The color of capsicums is a mix-
ture of carotenoids, principally capsanthin
(C40 Hs 8 03) together with carotene, capso-
rubin, zeaxanthin, cryptoxanthin and lutein.
The chemistry of the pigments found in
capsicums was extensively reviewed by
Govindarajan (1986b) and its measure-
ment in a later review by Govindarajan,
Rajalakshmi and Chand (1986).
Oleoresin Capsicum (Red Pepper)
Depending on the source of the capsicum
and the solvent used, the yield of oleoresin
is about 8-10 percent. The method of
production is described in detail by
Govindarajan (1986a). As noted under
the following heading, a wide range of
 Natural Flavoring Materials 271

oleoresin capsicum is offered commercially, has since been widely applied. Scoville units
differing in capsaicin content (pungency) are defined as the greatest dilution, ex-
and in color value. pressed as the denominator of the dilution
Specification: EOA No. 244. factor, at which a pungent sensation is
This is a clear greenish-orange to dark perceived under the stated test conditions
red viscous fluid oleoresin, which may form (i.e., a limiting dilution of 1 in 25,000 is
a slight deposit on long storage. It should be equivalent to 25,000 Scoville units). Gillette,
well mixed before use. The pungency and Appel and Lego (1984) have proposed a
color are normally standardized by the different method to determine pungency.
addition of an edible oil or the oil derived They use a trained panel to evaluate the
from capsicum seeds. pungency of a standardized concentration of
The EOA specification requires a mini- product (e.g. 0.25 g of fruit powder dis-
mum of 480,000 Scoville units for oleoresin solved in 100 g hot water then making an
capsicum and 240,000 for oleoresin red 8,000-fold dilution in the presence of Poly-
pepper. These are coupled with a color sorbate 80). The panel then compares
value of not more than 4,000 and 20,000, the pungency of the sample to that of a
respectively. reference, marking the intensities on a
The following grades are available 15-cm line scale. The values obtained are
commercially (Table 7-37). converted to Scoville Heat Units.
The above figures are taken from manu- Numerous papers have been published
facturer's literature and specifications. It is establishing correlations between sensory
likely that other products having a different methods for determining pungency and in-
balance between pungency and color value strumental methods of determining capsaici-
are offered to suit particular requirements. noids. These methods and their correlation
It is recommended that lib. of regular to sensory results have been compre-
pungency oleoresin will replace 20 lb. of a hensively reviewed by Govindarajan,
good grade ground cayenne pepper in a Rajalakshmi and Chand (1986).
seasoning. Scoville Test Method The Scoville test
method is published as an international
Determination of Pungency standard (ISO 3513-1977) and as a British
The pungency of capsicums and of products Standard (BS 4585, Part 7; 1977) for appli-
made from them is generally rated in terms cation to ground chilies. The following
of Scoville units. This sensory method was procedure is suggested for the evaluation of
originally described by Scoville in 1912 and oleoresins of capsicum or red peppers:
Accurately weigh 0.200 g of the well-
TABLE 7-37. The grades of oleoresin capsicum mixed oleoresin sample into a 50-ml volu-
metric flask, add 95 percent ethanol, shake
Scoville Capsaicin
Units Content Color Units
well and adjust to the mark. Allow any
insoluble matter to settle. Prepare a stan-
1,630,000- 12.75-14.0% A brownish-red dard solution by diluting O.lOml of the test
1,825,000 oleoresin not color solution to 100 ml with a 5 percent solution
standardized
1,000,000
of sucrose in water (equivalent to a dilution
Not color standardized
500,000 Max3,500 of 1: 250,000). Present 5 ml of the standard
350,000 16,000 solution to each of five panel members with
305,000 2.4% 15,800 instructions to swallow all at once and note
200,000 3,500 whether or not there is a pungent sensation
160,000 20,000
147,000 in the throat. A just perceptible positive
27,900
sensation in the throats of three out of five
272 Source Book of Flavors

assessors at this dilution is equal to 250,000
Scoville heat units.
The ISO method requires a series of
dilutions to be made bracketing the antici-
pated pungency of the sample; the assess-
ment is carried out from the weakest to the
strongest until a pungency is detected.
A lapse of at least 30 minutes should be
allowed before any repeat pungency tests
are carried out.
The Scoville rating can be equated to
capsaicin content; one manufacturer of
oleoresin capsicum quotes 1 percent of
capsaicin as equivalent to 127,000 Scoville
units, but Mathew et al. (1971A) quotes
150,000 Scoville units.
Capsaicinoid Content As noted earlier,
many methods of determining the cap-
saicinoid content of capsicum products
have been published and reviewed by
Govindarajan, Rajalakshmi and Chand
(1986). After an initial extraction of the
pungent and coloring components, the
mixed extractives must be separated using
either column, paper, gas-liquid, thin-layer
or high-performance liquid chromatography
and the capsaicin fraction quantitatively
evaluated. Some excellent correlations to
Scoville Heat Units have been obtained, as
is evident from Fig. 7-11.
Color Value
The EOA requires oleoresin capsicum to
contain a maximum of 4,000 color units
(ASTA) and for oleoresin red pepper a
maximum of 20,000 units, determined by
the method described under oleoresin
paprika (EOA No. 239). Most manufac-
turers have adopted the same basis for
specifying the color units. (Note that
methodology for the determination of
color in capsicums has been reviewed by
Govindarajan, Rajalakshmi and Chand,
1986).

, .... u ·- 0·11

-... IO r • 0·11 i IU JS

•
.! 40
:
•
·==
:II> 30
0
u
ut
20

10

0·1 0·£ O·S 0·5

Total c:apsaicinoids bJ HPLC,•Io

FIGURE 7-11. Regression of Scoville value on percent total regression

capsaicinoids by HPLC. (Govindrajan et al. 1987)

The method consists of preparing a 1 in
10,000 solution of the well-mixed sample
in acetone and determining its maximum
absorbance within the range 450-470 nm.
The observed reading is multiplied by a
factor of 61,000 to give color units. This
factor gives results that equate with those
obtained by an alternative visual method of
evaluation. (e.g., optical density = 0.26;
0.26 x 61,000 = 15,800 color units).
References: Capsicum
Almela, L., Lopez-Roca, J.M., Candela, M.E.,
and Alcazar, M.D. 1990. Separation and
determination of individual carotenoids
in a Capsicum cultivar by normal-phase
high-performance liquid chromatography.
J. Chromatog. 502(1):95-106.
Atanda, 0.0., Akano, D.A., and Afolabi, J.F.
1990. Mycoftora of dry "tatase" pepper
(Capsicum annuum L.) stored for sale in
Ibadan markets. Letters Appl. Microbia.
10(1):35-37.
Biacs, P.A., Daood, H.G., Pavisa, A., and
Hajdu, F. 1989. Studies on the carotenoid
pigments of paprika (Capsicum annuum L.
var. Sz-20). J. Agric. Food Chern. 37(2):350-
353.
British-Standard; BS 4585. 1989. Methods of test
for spices and condiments. Part 7. Deter-
mination of Scoville index of chillies.
Buttery, R.G. et al. 1976. Some 4,5-dialkyl-
thiazoles with potent bell pepper-like aromas.
J. Agric. Food Chern. 24:1-3.
Buttery, R.G., Seifert, R.M., Lundin, R.M.,
Guadagni, D.G., and Ling, L.C. 1969.
Characterization of some volatile constituents
of bell peppers. J. Agric. Food Chern. 17:322-
1327.
Curl, A.L. 1962. The carotenoids of red bell
peppers. J. Agric. Food Chern. 10:504-509.
Ekumdayo, 0., Laakso, 1., Adegbola, R.M.,
Oguntimein, B., and Sofowora, A. 1988.
Essential oil constituents of ashanti pepper
(Peper guineense) fruits (berries). J. Agric.
Food Chern. 36(5):880.
Gillette, M.M., Appel, C.E., and Lego, M.C.
1984. A new method for sensory evaluation of
red pepper heat. J. Food Sci. 49:1028.
Govindarajan, V. and Ananthakrishna, S. 1974.
Paper chromatographic determination of
capsaicin. Flavour Ind. 5:176-178.
Govindarajan, V.S. 1985. Capsicum-produc-
Natural Flavoring Materials 273
tion, technology, chemistry and quality. I.
History, botany, cultivation and primary
processing. Crit. Rev. Food Sci. Nutr. 22:109.
Govindarajan, V.S. 1986a. Capsicum-pro-
duction, technology, chemistry and quality.
II. Processed products, standards, world
production and trade. Crit. Rev. Food Sci.
Nutr. 23:207.
Govindarajan, V.S. 1986b. Capsicum-produc-
tion, technology, chemistry and quality. III.
Chemistry of the color, aroma and pungency
stimuli. Crit. Rev. Food Sci. Nutr. 24:245.
Govindarajan, V.S., Rajalakshmi, D., and
Chand, N. 1987. Capsicum-production,
technology, chemistry and quality. IV.
Evaluation of quality. Crit. Rev. Food Sci.
Nutr. 25:185.
Govindarajan, V.S. and Sathyanarayana, M.N.
1991. Capsicum-production, technology,
chemistry and quality. V. Impact on phy-
siology, pharmacology, nutrition and meta-
bolism; structure, pungency, pain and desen-
sitization sequences. Crit. Rev. Food Sci.
Nutr. 29:435.
Kawada, T. and Iwai, K. 1988. Development
and use of active principles of spices.
Cayenne pepper. Up-to-Date-Food-Pro-
cessing fShokuhin-Kaihatsu]; 23(6):28-31.
Maga, J.A. 1975. Capsicum. C.R.C. Crit. Rev.
Food Sci. Nutr. 6:177-199.
Mathew, A.G., Lewis, Y.S., Jagadishan, R.,
Nambudiri, E.S., and Krishnamurthy, N.
1971a. Oleoresin of capsicum. Flavour Ind.
2(1):23.
Mathew, A.G., Lewis, Y.S., Jagadishan, R.,
Nambudiri, E.S., and Krishnamurthy, N.
1971b. Capsaicin. Flavour Ind. 2:691, 693-
695.
Nelson, E.K. 1919. Vanillyacylamides. J. Am.
Chern. Soc. 41:2121.
Pichard, H., Caude, M., Morin, P., Richard, H.,
and Rosset, R. 1990. Identification of pepper
essential oil constituents by various chromato-
graphy-spectroscopy couplings. Analusis
18(3): 167-178.
Pino, J., Rosado, A., and Gonzalez, A. 1989.
Analysis of the essential oil of pimento berry
(Pimenta dioica). Nahrung 33(8):717-720.
Salzer, U-J. 1975a. Routine analysis of spice
constituents represented by a study of extracts
(oleoresins). Mittelungsbl. GDCh-Fachgruppe
Lebensmittelchem. Gerichtl. Chern. 2g, (3/4):
132-153. (German)
Salzer, U-J. 1975b. Analytical evaluation of
 274 Source Book of Flavors
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6, 151-157. II. Ibid. 6, 206-210.
III. Ibid. 6, 253-258.
Seifert, R.M. 1970. Synthesis of some 2-
methoxy-3-alkylpyrazines with strong bell
pepper-like odors. J. Agric. Food Chern.
18:246-249.
Sumathikkutty, M.A., Rajaraman, K.,
Padmakkumari, K.P., Narayanan, C.S., and
Mathew, A.G. 1984. Analysis of oils from
commercial grades of pepper. Indian Perfum.
28(3):119.
Van Gernert, L.J., Nijssen, L.M., and Maarse,
H. 1981. Improvements of the Scoville
method for the pungency determination of
black pepper. In Flavour '81, Weurman
Symp., 3rd. ed. P. Schreier, pp. 211. Berlin:
Walter de Gruyter.
Verghese, J. 1989. On the isolation of oleoresin
black pepper by steam distillation-cum-
solvent extraction and tailoring of oleoresin.
Perfum. Flav. 14(6):33.
Wood, A.B. 1987. Determination of the pungent
principles of chillies and ginger by reversed-
phase high-performance liquid chromato-
graphy with use of a single standard sub-
stance. Flav. Frag. J. 2(1):1-12.
Caraway
Caraway is the dried ripe fruits (incorrectly
called seeds) of a biennial Umbelliferous
plant (Carum carvi L.), which is native to
Europe but common throughout Asia and
North Africa.
Commercial Sources
The Netherlands, the former Soviet Union,
Syria, Poland, Bulgaria, Romania, Yugo-
slavia, Morocco and India.
Description
Light brown to dark brown separated
mericarps, free from stalk; 4-6 mm long,
curved and tapered at one end. The surface
bears 5 yellowish longitudinal ridges.
Volatile Oil Content
3-7 percent. Fixed oil content: About 15
percent Sensory character: Agreeably fresh,
aromatic, slightly minty odor, pleasantly
fruity, cooling taste with distinctly bitter,
astringent effect if the fruit is chewed.
Oil of Caraway
Worldwide production of caraway oil in
1984 was estimated at about 10 metric tons.
The Netherlands, Poland and Egypt were
the primary suppliers of this oil (Lawrence
1985a).
Specification in FCC II (1972); BP
(1980); NF XV (1980).
Colorless to very pale yellow oil be-
coming more yellow on exposure to light;
specific gravity (25-C/25°C), 0.900-0.910
(some commercial specifications quote as
high as 0.940); optical rotation (20°C), +70°
to +80°; refractive index (20°C), 1.484 to
1.488; the oil should contain not less than 50
percent by volume of ketones calculated as
carvone.
Constituents Salveson and Baerheim-
Svendsen (1976), Rothbacher and Suteu
(1975), Lawrence (1980, 1982/8311985b),
Fleisher and Fleisher (1988), and Formacek
and Kubeczka (1982) have reported on the
composition of caraway oil. The results of
Lawrence (1980) are presented below:
a-thujene (trace)
a-pinene (0.1%)
camphene (trace)
f3-pinene (trace)
sabinene (0.1%)
myrcene (0.1%)
germacrene D (0.1%)
a-phellandrene (trace)
a-terpinene (trace)
Iimonene (49.8%)
f3-phellandrene (trace)
y-terpinene (0.1%)
p-cymene (trace)
terpinolene (trace)
octanal (trace)
linalool (0.1%)
cis-p-menth-2-en-1-ol (trace)
terpinen-4-ol (trace)
trans-dihydrocarvone (0.6%)
cis-dihydrocarvone (0.2%)
neodihydrocarveol + ll-3-carene (trace)
carvone (47.1%)
dihydrocarveol (trace)
isodihydrocarveol (trace)

neoisodihydrocarveol (trace)
cis-p-mentha-2,8-dien-1-ol (trace)
trans-carveol (0.4%)
cis-carveol (0.2%)
nonanal (trace)
Oleoresin Caraway
A greenish-yellow fruit oleoresin which,
when prepared directly from caraway,
contains 20-25 percent volatile-like oil and
65-75 percent of fixed oil.
The available grades are shown in Table
7-38.
In view of the high percentage of fixed
oil in this product, it is usual to add the
maximum permitted amount of antioxidant.
References: Caraway
El-Deeb, S.R., Karawaya, M.S., Wahba, S.K.,
and Ebeid, F.M. 1962. The examination of oil
of caraway by gas-liquid partition chromato-
graphy. U.A.R. J. Pharm. Sci. 3(1):63-79.
(Chern. Abstr. 6, (8):9351a.)
Fleisher, A. and Fleisher, Z. 1988. The essential
oil of annual Carum carvi L. grown in Isreal.
In Flavors and Fragrances; A World Prespec-
tive, eds. B.M. Lawrence, B.D. Mookherjee,
and B.J. Willis. New York: Elsevier.
Formacek, K. and Kubeczka, K.H. 1982. Essen-
tial oils analysis by capillary chromatography
and carbon-13 NMR spectroscopy. New York:
John Wiley & Sons.
Haelvae, S., Hirvi, T., Maekinen, S., and
Honkanen, E. 1986. Yield and glucosinolates
in mustard seeds and volatile oils in caraway
seeds and coriander fruit. I. Yield and
glucosinolate contents of mustard (Sinapis
sp., Brassica sp.) seeds. J. Agric. Sci. Finland
58(4): 157-162.
Haelvae, S., Hirvi, T., Maekinen, S., and
Honkanen, E. 1986. Yield and glucosinolate
of mustard seeds and volatile oils of caraway
seeds ad coriander fruit. III. Yield and
volatile oils of coriander fruit ( Coriandrum
sativum L.). J. Agric. Sci. Finland 58(4):169-
173.
International Organization for Standardization.
1987. Oil of caraway (Carum carvi Linnaeus).
International-Standard; ISO 8896:1987.
Lawrence, B.M. 1976. Progress in essential oils.
Caraway. (A monthly review). Perfum. Flav.
1(2):17; 2(1):3.
Natural Flavoring Materials 275
TABLE 7-38. The grades of oleoresin caraway
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%)
60 5-7 3-4.2
63-70 2.51 6-1.75
Lawrence, B.M. 1980. Progress in essential oils.
Caraway. Caraway oil. Perfum. Flav. 5(4):6-
16.
Lawrence, B.M. 198211983. Progress in essential
oils. Perfum. Flav. 7(6):20.
Lawrence, B.M. 1985a. Progress in essential oils.
Perfum. Flav. 10(1):43.
Lawrence, B.M. 1985b. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Rothbacher, H. and Suteu, F. 1975. Ketone
fraction of caraway oil. Parfum. Kosmet.
56(1):1-4. (German)
Rothbacher, H. and Suteu, F. 1974. Origin and
formation of carvone in oil of caraway. Planta
Med. 26:283-288.
Salveson, A. and Baerheim-Svendsen, A. 1976.
Gas-liquid chromatographic separation and
identification of the constituents of caraway
seed oil. Planta Med. 30:93-96.
Wichtmann, E.M. and Stahl-Biskup, E. 1987.
Composition of the essential oils from cara-
way herb and root. Flav. Frag. J. 2(2):83-89.
Cardamom
Cardamoms are the dried, nearly ripe fruits
of Elettaria cardamomum (L.) Maton
var. miniscula Burkhil;, a member of the
Zingiberaceae and native to India. Other
species, including Amonum subuletum, A.
aromaticum and A. xanthioides, which grow
in India, have been described by George
(1974) and Mitra (1975).
Commercial Sources
India (Malabar, Mangalore and Mysore),
Sri Lanka, Guatemala, Costa Rica and El
Salvador.
Description
The commercial spice is the whole fruit
consisting of a tough, fibrous capsule en-
closing a tightly packed mass of dark
276 Source Book of Flavors

reddish-brown to almost black seeds. rotation (20°C), +22" to +44°; refractive

The capsule may be in its natural state
or bleached. The unbleached capsule is
brownish-green to pale yellowish-green and
may carry numerous brown warts on its
surface; the bleached spice is usually
selected for its "bold" appearance and
is creamy white. The three-sided, oval
capsules are 7.5 to 15 mm in length and
about 7.5mm wide. The surface is smoothly
wrinkled and striated longitudinally.
The seeds, which constitute the desired
part of the spice, are hard, irregularly
angular and about 2 mm long. They are
usually retained in the capsule until required
as they rapidly lose aroma.
Volatile Oil Content
3-8 percent (seeds).
Sensory Character
Sweetly aromatic, penetrating, camphor-
aceous-cineolic odor; pleasantly full, warm
flavor with a marked pungency.
Oil of Cardamom
Cardamon oil is produced in limited quan-
tity in Sri Lanka, India and Guatemala.
Total worldwide production was esti-
mated to be less than 4 metric tons in 1984
(Lawrence 1985).
Specification in EOA No. 289, FCC II
(1972), NF XV (1980).
A colorless to very pale yellow oil that
darkens when exposed to light; specific
gravity (25°C/25°C), 0.917 to 0.947; optical
index (20°C), 1.463 to 1.466; solubility (80
percent ethanol), 1 to 2 vol.
Types of Cardamom Oil Cardamom oil
can be produced from one of three types of
cardamom:
Malabar type- Elettaria cardamomum
Maton var. miniscula Burkhill syn. E. car-
damomum Maton var. a-minor Thwaites;
cv. Malabar; cv. Malabar-Ceylon (Sri
Lanka); E. repens (Sonner) Baill.
Mysore type-Elettaria cardamomum
Maton var. miniscula Burkhill syn. E.
cardamomum Maton var. a-minorThwaites;
cv. Mysore; cv. Mysore-Ceylon (Sri Lanka);
E. repens (Sonner) Baill.
Ceylon (Sri Lanka) type-Elettaria
cardamomum Maton var. P-major Thwaites
syn. E. major Thwaites; cv. "Long wild
cardamom"; E. ensal (Gaestn.) Abeywick.
Composition of Cardamom Oil The
chemical composition of oil of cardamom
has been investigated by numerous re-
searchers. As with all of the essential oils,
composition depends upon the source of
the oil. The major oil constituents from
different sources have been summarized by
Pieribattesti, Smadja and Mondon (1988)
and are presented in Table 7-39.
More detail can be found on cardamom
oil composition by consulting the review of
Lawrence (1983). A detailed list of con-
stituents in various oils determined by
Bernhard et al. (1971) is presented in Table
7-40.

TABLE 7-39. Constituents of cardamom oil

Compound Malabar Type Ceylon Mysore Type Indian Reunion

a-pinene 0.7 0.7 1.4 1.5 1.4

sabinene and ~-pinene 4.6 3.8 3.2 3.0 3.3
limonene 1.7 2.2 2.4 11.6 6.0
1,8-cineole 26.5 36.0 41.0 36.0 44.6
Jinalool 3.7 3.5 0.4 3.0 1.8
linalyl acetate 7.7 2.6 1.6 2.5 o:r
a-terpineol 1.0 1.0 0.8 2.6 3.4
a-terpineol acetate 34.5 30.0 30.0 31.3 29.2
Lewis et al. (1966, 1967); Lawrence (1983)
 Natural Flavoring Materials 277

TABLE 7-40. Constituents of cardamom oil

Malabar type (1) Malabar type (1) Mysore Ceylon Commercial

(Sri Lanka) (Guatemala) type type (2) Oil

a-Pinene 1.10 0.71 1.40 13.00 0.59

Camphene (3) 0.02 0,03 0.04 0.13 0.01
Sabinene 2.50 3.40 3.10 4.90 1.2
beta-Pinene (3) 0.20 0.34 0.20 4.90 0.19
Myrcene (3) + 1.80 1.50 1.10 2.50 0.37
a-terpinene (3)
a- Phellandrene trace 0.01 trace 0.42 trace
Limonene 0.02 0.12 0.14 2.10 0.28
1,8-Cineole 31.0 23.4 44.0 3.3 51.30
Methyl heptenone (3) 0.04 0.09 0.05 3.1 0.07
gamma-Terpinene 0.04 0,07 0,07 11.2 0.08
trans-Sabinene 0.12 0.34 0.10 22.2 0.03
hydrate (3)
Linalool 2.10 4.5 3.0 3.70 1.40
Camphor (3) trace 0.01 trace 0.35 0.03
~-Terpineol (3) trace 0.04 0.06 0.13 0.13
+citronella! (3)
Borneol (3) trace 0.03 trace trace trace
Terpinen-4-ol 0.14 0.28 0.87 15.3 0.88
a-Terpineol 1.40 1.90 1.50 0.86 3.30
Geranial (3) 0.09 0.08 0.07 0.48 0.06
Citronellol trace 0.04 trace 0.01 0.02
Nero! 0.02 0.04 0.06 0.78 0,07
Linalyl acetate 3.30 6.30 3.10 0.31 0.74
Neral (3) 0.16 0.15 0.19 1.30 0.13
Geraniol 0.27 0.38 0.25 0.34 0.57
Terpinen-4-yl aceteate trace 0.02 trace 1.70 0.09
Ascaridole (3) 0.02 0.02 0.01 0.05 0.03
a-Terpinyl acetate 52.5 50.70 37.00 0.14 34.60
Neryl acetate 0.09 0.09 0.02 0.03 0.05
Geranyl acetate 0.08 0.13 0.15 1.50 0.18
Bisabolene (3) 0.09 0.83 0.07 0.44 0.05
+trans-nerolidol (3)
cis-Nerolidol (3) 0.23 1.60 0.28 0.37 0.65
Farnesol (3) 0.01 0.06 0.02 0.05 0.01
(I) Probably Mysore type
(2) Long wild cardamom
(3) Identification by retention time

Oleoresin Cardamom Salzer (1975) recommends the deter-

A dark green to golden-brown fluid mination of esters in the recovered volatile
oleoresin. The following grades are oil as a measure of the flavoring quality of
available: the oleoresin.

Volatile Suggested Volatile Oil References: Cardamom

Oil Content Use Rate in Dispersion Bernhard, R.A., Wijesekera R.O.B., and
(m11100g) (%) (%) Chichester, C.O. 1971. Terpenoids of car-
52-58 4 2.08-2.32 damom oil and their comparative distribution
70 4 2.8 among varieties. Phytochem. 10:177-184.
278 Source Book of Flavors
George, K.U. 1974. The cardamom plantation
industry. Development and prospects of spice
industry in India. Symp. Proc. Mysore, India.
Govindarajan, V.S., Narasimhan, S.,
Raghuveer, K.G., and Lewis, Y.S. 1982.
Cardamom-production, technology, chemis-
try, and quality. CRC Crit. Rev. Food Sci.
Nutr. 16(3):229-326.
International-Standard; ISO 4733. 1981. Oil of
cardamom.
Lawrence, B.M. 1976. Progress in essential oils.
Cardamom. (A monthly review). Perfum.
Flavorist 1(5): 11.
Lawrence, B.M. 1983. Progress in essential oils.
Perfum. Flavorist 8(4):63.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Mitra, C.R. 1975. Important spices of India.
IV. Cardamoms (Elettaria cardamomum,
Amomun subulatum, A. aromaticum, A.
xanthioides, Zingiberaceae). Riechst. Aromen
Koerperpflegem. 25(11):326. (German)
Pieribattesti, J.C., Smadja, J., and Mondon,
J.M. 1988. Composition of the essential oil of
cardamom (Elettaria cardamomum Maton)
from Reunion. Dev. Food Sci. 18:697-706.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts ( oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Sankarikutty, B., Sreekumar, M.M., Narayanan,
C.S., and Mathew, A.G. 1988. Studies on
microencapsulation of cardamom oil by spray
drying technique. J. Food Sci. Techno!. India
25(6):352-356.
Sarath-Kumara, S.J., Packiyasothy, E.V., and
Jansz, E.R. 1985. Some studies on the effect
of maturity and storage on the chlorophyll
content and essential oils of the cardamom
fruit (Elettaria cardamomum). J. Sci. Food
Agric. 36(6):491-498.
Cassia
See Cinnamon.
Cassia Buds
Of the Cinnamomum genus, the cassia and
cinnamon species are of the greatest com-
mercial significance. Large amounts of Celery
C. cassia (Chinese cassia) are grown in the Celery is the dried ripe fruit (incorrectly
southeastern provinces of China. C. loureirii called seed) of a herbaceous Umbelliferous
is native to China and Japan and is the
source of Saigon cinnamon or cassia.
C. buramanni is cultivated in Sumatra and
produces a product known as Batavia or
Korinji cinnamon. The designation of a
product as being either "cinnamon" or
"cassia" may not be universally agreed
upon. The reader is encouraged to read the
section of this chapter on cinnamon for a
better overall view of these products.
While bark or leaves may be used for
distillation to obtain a cinnamon oil, the
buds are used to obtain a cassia oil.
Description
Grayish-brown fruits of variable size, but
about 6-10 mm long and 5 mm wide at their
tops. The buds consist of a hard reddish-
brown seed, smooth and embedded in a
dark cup formed by the calyx. Only the
upper surface of the seed is visible. The
calyx is wrinkled and narrows into a thick
stalk.
Sensory Character
The aroma is cassia-like and agreeably
spicy; the flavor is sweet, somewhat warmly
pungent.
Volatile Oil Content
About 2 percent, containing about 80
percent cinnamic aldehyde. Cassia buds are
useful as a convenient form of adding
cinnamon flavor to sweet pickles and other
dishes where small amounts of the whole
spice are needed.
References: Cassia Buds
Lawrence, B.M. 1978. Progress in essential oils.
Cassia. (A monthly review). Perfum. Flavorist
3(1):54; 3(3):54.
Senanayake, U.M. and Wijesekera, R.O.B.
1989. The Volatiles of the Cinnamomum
Species. 11th International Congress of
Essential oils, Fragrances and Flavors. Oxford
Pub.: New Delhi, India. pp. 103.
 Natural Flavoring Materials 279

plant (Apium graveolens L.) that is native to Sensory Character

southern Europe. The green or etiolated
fresh stems are also widely eaten as a
vegetable and as a source of flavor in many
food products.
Commercial Sources
Southern France, the Netherlands, India,
United Kingdom and United States
(California).
Description
Separated flat to slightly curved mericarps,
some with stalks attached; very small,
usually less than 1 mm in length, surface has
five well-defined ridges that are visible on
magnification.
Volatile Oil Content
2.5-3 percent
Fixed Oil Content
About 15 percent
Warm, sweetly spicy aroma, which is slightly
penetrating; the flavor is warmly aromatic
and slightly burning.
Oil of Celery
India is the major supplier of celery seed
oil (20 metric tons). Smaller amounts are
produced in China, Egypt, France, the
United Kingdom and the USA to total
about 25 metric tons in 1984 (Lawrence
1985a).
Specification in BOA No. 85; FCC II
(1972). A yellow to greenish-brown oil;
specific gravity (25°/25°C), 0.872 to 0.910;
optical rotation (20°C), +48° to + 78°;
refractive index (20°C), 1.480 to 1.490; acid
value max 3.5; saponification value 35 to 75;
solubility (90 percent ethanol), 6 to 8 vol
with some opalescence.
Constituents Wilson (1970), Salzer
(1975), Fehr (1979), Formacek and
Kubeczka (1982) and Lawrence (1985b)

TABLE 7-41. Compounds of celery oil

Compound Fruit Flowers Leaf Stem Root

3-methyl-4-ethyl-hexane 0.1 0.3 16.7

a-pinene 0.1 0.5 0.2 0.5 1.0
camphene trace 0.1 trace 0.1 0.7
P-pinene 0.5 1.3 0.1 0.7 3.6
sabinene trace 0.1 trace
myrcene 1.2 14.8 33.6 11.5 0.8
a-terpinene trace trace 1.2
limonene 68.5 38.8 26.3 37.3 9.3
cis-P-ocimene 18.9 14.1 18.5 7.3
y-terpinene + trans-P-ocimene 0.1 1.8 2.2 6.8 18.2
p-cymene trace 0.5 0.5 1.7 13.2
terpinolene 0.1 0.4 0.2 trace 5.5
n-pentylcyclohexadiene 0.9 3.0 1.0 0.8 0.1
allo-ocimene 1 trace 0.2 0.3 0.5 0.1
allo-ocimene 2 trace 0.1 trace trace 0.4
n-pentylbenzene 1.7 0.2 trace trace 0.1
terpinen-4-ol trace 0.2 0.1 0.1 0.9
p-elemene + caryophyllene 0.5 1.5 1.4 1.7 0.7
a-humulene trace trace trace trace trace
a-terpineol 0.7 0.7 0.3 0.2 5.0
p-selinene 8.0 5.6 3.7 2.4 0.2
n-butylidene phthalide 8.0 1.3 0.9 0.6 0.5
n-butyl phthalide 0.2 1.9 6.2 11.9 0.5
ligustilide 0.2 0.6 0.2 0.3 1.2
3a,4-dehydroisobutyl-idene phthalide 6.5 2.9 3.2 1.3 trace
280 Source Book of Flavors

TABLE 7-42. The grades of celery oleoresin von Sellerie (Apium graveoloens L.) Phar-
mazie 36:374-376.
Volatile Oil Suggested Volatile Oil Formacek, V. and Kubeczka, K.H. 1982. Essen-
Content Use Rate in Dispersion
(ml/ 100 g) (%) (%) tial Oils Analysis by Capilllary Gas Chromato-
----------------- graphy and Carbon-13 NMR Spectroscopy.
9-11 3.5-6 0.31-0.66 Nt!w York: John Wiley & Sons.
12 3 0.36 Knight, D.W. and Pattenden, G. 1975. Synthesis
10-14 3 0.3-0.42 of alkylidene phthalide constituents of celery
40-45 3 1.2-1.35 odour and model for freelingyne. J. Chern.
Soc. Perkin Trans. No. 7:635-640.
Lawrence, B.M. 1985a. Essential oils-World
have reported on the constituents of celery production. Perfum. Flavorist 10:1-16.
oil. Fehr (1979) has studied the composition Lawrence, B.M. 1985b. Progress in essential oils.
of various organs of Apium graveolens L. Perfum. Flavorist 10(5):93.
var. graveolens and his data are presented in MacLeod, A.J., MacLeod, G., and Subramanian,
Table 7-41 (from Lawrence 1985b). G. 1989. Volatile aroma constituents of celery.
Phytochem. 27(2):373-375.
MacLeod, G. and Ames, J.M. 1989. Volatile
Oleoresin Celery
components of celery and celeriac. Phytochem.
A dark to light green fluid oleoresin. The 28(7):1817 -1824.
oleoresin extracted from the crushed seeds Miyazawa, T. 1988. Development and use of
contains about 25 percent of essential oil extracts. Vegetable (e.g., onion, garlic, carrot,
and about 60 percent of fixed oil. Four grades celery) extracts. Up-to-Date-Food-Processing-
are available (Table 7-42). [Shokuhin-Kaihatsu]; 23(7):51-55.
Salzer (1975) comments that the oil re- Salzer, U-J. 1975. Analytical evaluation of
covered from the oleoresin differs from that seasoning extracts (oleoresins) and essential
obtained by direct distillation of the seeds oils from seasonings. I. Int. Flavours Food
owing to some loss of d-limonene, but that _Additives 6:151-157. I_I. Ibid. 6:206-2~0. .
this it not a disadvantage as the flavoring, Wilson: C.W. 1970. Relative recovery and Identi-
ficatiOn of carbonyl compounds from celery
components are thereby concentrated, a!- t. 1 .1 1 "' d s . 35 .766 _ 768
. I f essen Ja 01 . . roo c1. . .
though the overa II pro fi le IS ess resh. The
flavor obtained from the seed oil or oleoresin
does not compare well with that of the fresh Cinnamon
vegetable form. The synthesis of alkydiene- The cinnamon of commerce is the dried
phthalide constituents of celery odor has inner bark of several species of the genus
been reported by Knight and Pattenden Cinnamomum, which are large evergreen
(1975). trees found in tropical rain forest regions
of the world (Senanayake and Wijesekera
References: Celery 1989). The designation of this spice is in-
Cu, J.Q., Zhang, Z.J., Pu, F., Perineau, F., volved: in the United Kingdom, the term
Delmas, M., and Gaset, A. 1990. GC/MS and "cinnamon" is taken to mean only the bark
GC/FTIR analysis of the essential oil of celery of Cinnamomum zeylanicum Nees., from
seed. J. Essen. Oil Res. 2(1):1-5. Sri Lanka (commonly called Ceylon Cin-
DePooter, H.L., Coolsaet, B.A., Dirinck, P.J.,
namon); in the United States, the designa-
and Schamp, N.M. 1985. GLC of the head-
space after concentration on Tenax GC and of tion "cinnamon" may include both C.
the essential oils of apples, fresh celery, fresh zeylanicum and C. cassia (L.) Blume,
lovage, honeysuckle and ginger powder. In (whereas in the United Kingdom this latter
Essential Oils and Aromatic Plants, eds., A.B. species is known only as "cassia.") The
Svendsen and J.J.C. Scheffer, pp. 67-78. source and designations of the many cin-
Netherlands: Martinus Nijhoff. namon species and varieties currently
Fehr, D. 1979. Untersuchung uber Aromastoffe handled in the spice trade are listed in Table

TABLE7-43. Species and designations of commercial
grades of cinnamon and cassia barks
Botanical Source Common Source Names
Cinnamomum True cinnamon
zeylanicum Nees. Ceylon, Seychelles cinnamon
C.cassia (L.) Blume Cassia lignea
Chinese, canton, Kwangtung,
Kwangsi, Yunnan, Honan,
Chinese Junk cassia or
cinnamon
C. loureirii Nees. Cassia lignea
Saigon, Vietnam, Danang,
Annan, Tonkin cinnamon or
cassia
C. burmanii Blume Cassia vera
Indonesia, Padang, Batavia,
Korintje, Korintoji, Java,
Macassar, Timor cassia or
cmnamon
7.43. The main types will be described under
four headings: Ceylon cinnamon, China
cassia-cinnamon, Saigon cinnamon and
Batavia cinnamon.
Ceylon Cinnamon
"True" cinnamon is the dried inner bark of
the shoots of the coppiced shrub C. zeylani-
cum Nees., which is indigenous to and culti-
vated in Sri Lanka. The trees are cut to
within a few inches of the ground and the
long shoots which form are cut down, usually
twice a year (in May and November), when
they reach 1 to 2 meters in length; the
bark is stripped off the shoots longitudinally,
the outer cork and inner woody tissues re-
moved by scraping; the strips are pressed
and packed, smaller within larger, and dried
to form a compound quill. They are graded
according to size, color and aromatic quality
ranging from 00000 (the highest grade) to 0
(the coarsest grade) together with waste ma-
terial, which is offered as quillings, feather-
ings and chips. The gradings were described
by Lawrence (1967). In the Seychelles, the
bark is collected every two years and may be
much thicker. From this source, the quills
are usually simple and much thicker than
the normal compound quills.
Commercial Sources Sri Lanka, India,
the Seychelles. The Malagasy Republic and
Brazil are also increasingly important
sources of this spice.
Natural Flavoring Materials 281
Description Single or double, closely
packed cylindrical compound quills in
lengths up to about 1 meter and about 1 em
in diameter. The outer surface is smooth,
dull and characteristically yellowish-brown,
marked with pale striations; cork is absent
except around small branch scars. The inner
surface is darker and also longitudinally
striated. The bark is about 0.5 mm thick, but
the Seychelles material may be up to 1 mm
thick. It is very brittle.
Volatile oil content 0.5 to 2 percent.
Sensory characters Sweetly aromatic,
warmly and characteristically spicy aroma
with a sweetly spicy flavor and a slightly
pungent, burning character.
Oil of Cinnamon Bark
Derived principally by the steam-distillation
of trimmings and chips. It was estimated
that worldwide production of cinnamon bark
oil (all sources and types except cassia oil)
was only 5 metric tons in 1984 (Lawrence
1985).
Specification in EOA No 87, FCC II
(1972), USP XX (1980), BP (1980).
A yellow oil that darkens and turns red-
dish brown with age; specific gravity (25°/
25°C), 1.010 to 1.030; optical rotation
(20°C), -2° to 0; refractive index (20°C),
1.573 to 1.591; solubility (70 percent
ethanol), 3 or more vol; aldehyde content
55 to 78 percent calculated as cinnamic
aldehyde.
Constituents
The composition of cinnamon bark oil was
investigated by Wijesekera eta!. (1974) and
the following components reported:
a-pinene (0.2%)
p-cymene (0.55%)
caryophyllene (1.35%)
a-terpineol (0.4%)
cinnamic aldehyde (74.0%)
eugenol (8.8%)
1,8-cineole (1.65%)
linalool (2.3%)
a-humulene (0.2%)
282 Source Book of Flavors

cuminaldehyde (0.25%) the seams of containers) and from rosin or

cinnamylacetate (5.1%) rosin oils, which are not unusual adulterants.
benzyl benzoate (1.0%)
Specifications in: FCC II (1972). A yel-
lowish to brownish oil, which darkens and
together with much smaller quantities of
thickens with age; specific gravity (25°t25°C),
several other terpene hydrocarbons and
1.045 to 1.063; optical rotation (20°C), -1°
camphor, acetoeugenol, piperitone, gera-
to + 1o; refractive index (20°C), 1.602 to
niol, safrole and cinnamyl alcohol.
1.614; solubility (70 percent ethanol), 2 vol;
The findings of Zurcher et al. (1974) are
total aldehydes, min 80 percent calculated
at considerable variance with these results
as cinnamic aldehyde.
and are commented on by Lawrence (1976-
Constituents The chief component of
1978).
cassia-cinnamon oil is cinnamic aldehyde (80
to 95 percent) together with cinnamyl ace-
China Cassia-cinnamon tate, cinnamic acid, benzaldehyde, methyl
This is the dried inner bark of C. cassia salicylaldehyde, methyl o-coumaraldehyde,
(L.) Blume, which is cultivated in southern salicylaldehyde and coumarin. About 40
China, Burma and Vietnam. The wood is components have been reported in this oil
cut and the thick bark removed and allowed (ter Heide 1972), whose value as deter-
to sun dry for one day; the inner layers minants of flavor quality is discussed by
are scraped away and the cleaned bark is Salzer (1975).
allowed to dry fully, during which time it
curls inward to form a channel. Saigon Cinnamon
Description Single or double rolls of The dried bark of C. loureirii Nees., which
bark about 25 to 40cm long, 1 to 2cm in is cultivated in Vietnam, is the principal
diameter and about 1 to 4 mm thick. The source.
unscraped bark is grayish and has a rough Description Single or double quills vary-
surface with an irregular, coarse appearance; ing in length from 15 to 20 em. The bark
the scraped bark is smooth, light reddish- differs considerably in appearance from
brown in color (darker than "true" cinna- grayish-brown pieces, 1 to 4 em in diameter
mon), but may have patches of grayish and about 5 mm thick to much thinner bark
outer cork. The commercial grades are very only about 1 mm thick. In the thicker pieces,
variable. the outer surface is very rough, showing
Volatile Oil Content 1.0 to 2.5 percent. numerous branch scars; the thinner bark has
Sensory Character Sweet spicy odor, a smooth almost shiny surface, free from
which is much coarser but fainter than that cork, and carrying longitudinal wavy ridges.
of Ceylon cinnamon; the flavor is warmly Volatile Oil Content 1 to 4 percent.
spicy with a harsh pungency and a slight Constituents: Kameoka et al. (1975)
burning effect. Not so pleasing as "true" have reported the following constituents in
cinnamon. the oil of C. loureirii of Japanese origin:
Oil of Cassia The main commercial a-pinene (0.5 percent), camphene (1.3 per-
source of this essential oil is China (160 tons/ cent), ~-pinene (0.2 percent), limonene (0.6
yr. in 1984-Lawrence 1985), but some percent), 1,8-cineole (2.3percent),p-cymene
high-quality oil, mostly for perfumery use, is (0.3 percent), linalool (4.9 percent), ben-
distilled in the United Kingdom from im- zaldehyde (0.4 percent), camphor (0.4
ported bark. The imported oil is usually percent), bornyl acetate (1.0 percent), a-
rectified in Europe or in the United States. terpineol (1.4 percent), hydrocinnamic
This is particularly necessary to ensure free- aldehyde (1.6 percent), cinnamic aldehyde
dom from lead contamination (derived from (78.1 percent), cinnamyl acetate (3.9 per-
 Natural Flavoring Materials 283

cent), cinnamic acid (1.0 percent). They also TABLE 7-44. Grades of cinnamon oleoresin
reported the presence of coumarin in the
Volatile Oil Suggested Volatile Oil
ether extract. Content Use Rate in Dispersion
(ml/100 g) (%) (%)
Batavia Cinnamon
This is thought to be the dried bark of 23-27 4 0.92-1.08
65 6 3.9
C. burmanii Blume, cultivated in parts of
Indonesia and exported from Jakarta.
Description: Reddish-brown double
TABLE 7-45. Characteristics of cinnamon leaf oils
quills 15 to 45 em long, about 2 em in dia-
meter and 1 to 5 mm thick; the bark is Sri Lanka Seychelles
smooth, straight, generally free from rough
Sp. Gr. 1.030 to 1.0501 1.040 to 1.060
cork and has no wavy lines.
(25°/25°C}
Optical + 1° to -2° 0 to -2°
Oleoresin Cinnamon rotation
Various types of cinnamon may be used for (20°C}
the production of the oleoresin, but care RI (20°C) 1.529 to 1.537 1.533 to 1.540
Solubility 1.5vol with 1 vol with
must be taken in the selection of the solvent. (70% opalescence opalescence
Polar solvents such as acetone produce a ethanol) on dilution on dilution
good extraction, but the resulting oleoresin Eugenol 80to88% 87to96%
rapidly polymerizes into an intractable plas-
tic-like solid when the solvent is removed.
This may be prevented by adding propylene Cinnamon Leaf Oils
glycol or glycerin to the final product. The The essential oil obtained by the steam distil-
nonpolar solvents recover the essential oil lation of the leaves of C. zeylanicum Nees.,
and some of the nonvolatile components, is available commercially and is imported
but the product lacks "body" and the color direct from Sri Lanka (90 tons) and India
is only poorly recovered. A satisfactory alter- (5-10 tons) as well as several minor regions
native for the production of dispersions for (e.g., Seychelles-1 ton), (Lawrence 1985).
use in seasonings is the use of a very finely It differs considerably from cinnamon bark
ground powdered polymerized oleoresin, oil as its main constituent is eugenol, hence
which has the full cinnamon color and much the aroma is that of clove rather than cinna-
of the richer spicy notes of the profile to- mon. The oils from Sri Lanka and the
gether with oil of cassia-cinnamon as the Seychelles differ in physicochemical charac-
main source of the characteristic topnotes of ters and this is reflected in the following
the flavor. specification:
The oleoresin may be a deep reddish- Specification in EOA No. 56; FCC II
brown to greenish-brown color and is gener- (1972).
ally a viscous fluid. The available grades are A light to dark brown oil having the
shown in Table 7-44. characters shown in Table 7-45.
Salzer (1975) discussed the evaluation of Constituents Wijesekera et al. (1974)
oleoresin cinnamon and concluded that reported the following components:
determination of the volatile oil content fol-
lowed by the GC examination of the re- a-pinene (0.2%)
covered oil in terms of cinnamic aldehyde, p-cymene (0.35%)
eugenol and benzaldehyde, or alternatively linalool (1.5%)
the direct determination of total aldehydes a-humulene (0.2%)
and coumarin content, were the best piperitone (0.1%)
methods for the flavor quality assessment. cinnamic aldehyde (1.3%)
284 Source Book of Flavors
eugenol (87 .0%)
cinnamyl alcohol (0.6%)
1,8-cineole (0.15%)
a-ylangene (0.25%)
caryophyllene (1.85%)
a-terpineol (0.15%)
safrole (0.65%)
cinnamyl acetate (0.8%)
acetoeugenol (1.0%)
benzyl benzoate (2.67%)
together with much smaller quantities of
several other terpene hydrocarbons, gera-
niol, methyl cinnamate and ethyl cinnamate.
References: Cinnamon
Archer, A.W. 1988. Determination of cinnamal-
dehyde, coumarin and cinnamyl alcohol in
cinnamon and cassia by high-performance
liquid chromatogaphy. J. Chromatog. 447(1):
272-276.
Cherukuri, S.R., Hansukhani, G., and Kapak-
kamannil, C.J. 1988. Stable cinnamon-flavored
chewing gum composition. European-Patent-
Application; EP 0 273 857 A2 (EP0273857 A2)
Warner-Lambert Co.
Dutta, A.B. 1961. A chemical method for dis-
tinguishing cinnamon from cassia. J. Assoc.
Off Anal. Chern. 44:639-640.
Formacek, V. and Kubeczka, K.H. 1982. Essen-
tial oils analysis by capillary chromatography
and carbon-13 NMR Spectroscopy. New York:
John Wiley & Sons.
Freeman, C.C. 1985. Brine saturation technique
for extracting light filth from ground cinna-
mon: intralaboratory study. J. Assoc. Offic.
Anal. Chern. 68(6):1093-1094.
Heide, R.T. 1972. Qualitative analysis of the
essential oil of cassia ( Cinnamomum cassia,
Blume). J. Agric. Food Chern. 20:747-751.
Hicks, C.L. and Abdullah, C. 1987. Photoxida-
tion of cinnamon oil. J. Food Sci. (4):1041-
1046.
Kameoka, H., Ogi, K., and Hirao, N. 1975.
The constituents of the essential oil of Cinna-
momum loureirii Ness. Kinki Daigaku
Rokogakubu Kenkyo Hokoku 10:47-51.
Karapinar, M. and Aktug, S.E. 1986. Microbio-
logical quality of ground cinnamon: incidence
of Bacillus cereus. Mitteilungen-aus-dem-
Gebiete-der-Lebensmitteluntersuchung-und-
Hygiene 77(4):520-527.
Lawrence, B.M. 1967. A review of some of the
commercial aspects of cinnamon. Perfum.
Essent. Oil Rec. 58:236-241.
Lawrence, B.M. 1976-1978. Progress in essen-
tial oils. Cinnamon. (A monthly review). Per-
fum. Flavorist 1(4):31; 1(6):32; 2(3):53; 2(5):
44; 3(3):55; 3(4):55-56.
Lawrence, B.M. 1969. Determination of the
botanical origin of the cinnamons of commerce
by thin-layer chromatography. Can. Inst. Food
Techno/. 1.2:178-180.
Lawrence, B.M. 1985. Essential oils-World pro-
duction. Perfum. Flavorist 10:1-16.
Paovalo, C. and Chulasiri, M.U. 1986. Bacterial
mutagenicity of fractions from chloroform ex-
tracts of Ceylon cinnamon. J. Food Protect.
49(1):12-13.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives fi:151-157. II. Ibid. 6:206-210. IJI.
Ibid. 6:253-258.
Senanayake, U.M. andWijesekera, R.O.B.1989.
11th International Congress of Essential oils,
Fragrances and Flavours. New Delhi, India,
eds. Bhattacharya, S.C., Sen, N., and Sethi,
K.L. pp. 103.
Senanayake, U.M. eta!. 1978. Volatile constitu-
ents of cinnamon (Cinnamomum zeylanicum)
oils. J. Agric. Food Chern. 26(4):522-524.
Smith, A.E. 1986. International trade in cloves,
nutmeg, mace, cinnamon, cassia and their
derivatives. Report, Tropic. Dev. Res. Instit.
G193, ix + 161pp. ISBN 0-85954-203-3.
Tateo, F. and Chizzini, F. 1989. The composition
and quality of supercritical C0 2 extracted cin-
namon. J. Essen. Oil Res 1(4):165-168.
Way, R.M. 1985. Volatile oil analysis of cassia
bark (cinnamon): Investigation of systematic
errors. J. Assoc. Offic. Anal. Chern. 68(4):
622-625.
Wijesekera, R.O.B., Jeyawardene, A.L., and
Rajapakse, L.S. 1974. Volatile constituents of
leaf, stem and root oils of cinnamon, Cinna-
momum zeylanicum. J. Sci. Food Agric. 25:
1211-1220.
Wijesekera, R.O.B. 1978. The chemistry and
technology of cinnamon. C.R.C. Crit. Rev.
Food Sci. Nutr. 10(1):1-30.
Zurcher, K., Rardon, H., and Strack, Ch. 1974.
The examination of cinnamon by gas chroma-
tography. Mitt. Geb. Lebensmittelunters. Hyg.
65:440-452. (German)

Clove
Cloves are the dried unopened flower buds
of Syzygium aromaticum (L.) Marr and
Perry! (previously classified as Eugenia
caryophyllus (Spreng.) Bullock and
Harrison, E. caryophyllata Thunberg or E.
aromaticus (L.) Bailley), which is a large
tree native to Amboyna and other Moluccan
islands. The flowers are borne in clusters at
the end of short stalks. The unopened buds
are initially white, turning to green and
finally scarlet at which time they are gathered
by hand, sun dried, during which they change
to the familiar dark reddish-brown color,
and are then ready for grading prior to
shipment. Poorer grades of cloves may con-
tain "blown cloves," which are the expanded
flowers from which the petals and stamens
have been detached. Clove stalks as well as
"mother cloves," which are the ripening
fruits, may also be present. In many specifi-
cations for clove, the amount of stalk is
limited to a maximum of 5 percent. All of
these adulterants contain less volatile oil
than the genuine spice. The leaves and
flower stalks (stems) are also aromatic and
are normally harvested and distilled for their
essential oil.
Commercial Sources
Tanzania (Zanzibar and Pemba), Malagasy
Republic, Malaysia (Penang) and Sri Lanka.
Amboyna cloves generally command a
higher price than those from other sources,
although they are not so large as those from
Penang.
Description
Dried cloves have a characteristic appear-
ance and are 10-17.5mm long; the lower
portion is a four-sided, slightly flattened
hypantheum, which is crowned by four thick
acute sepals surrounding a paler spherical
head of unexpanded flower petals. The
hypantheum will exude essential oil when
indented with the fingernail.
Volatile Oil Content
15 to 20 percent, consisting mainly of
eugenol (85-95 percent), depending on the
Natural Flavoring Materials 285
method of distillation (Moyler and Heath
1988).
Constituents
In addition to the essential oil, cloves con-
tain about 13 percent of tannins (quercitan-
nic acid) and about 10 percent of fixed oil.
Depending on the source, they yield 6-12
percent of nonvolatile ether extract.
Sensory Character
Strong, spicy, warmly phenolic odor and a
pungent, medicinal flavor accompanied by
some astringency.
Clove Oils
Three different clove oils, as well as in-
numerable blends that also may contain cin-
namon leaf oil, are offered commercially.
These are oil of clove bud, clove leaf and
clove stem. The latter two oils are frequently
rectified to improve their overall profile.
They are also a commercial source of
eugenol.
Oil of Clove Bud Obtained by the dis-
tillation of clove buds either in the produc-
ing region or from imported cloves.
Specification in FCC II (1972), USP
XX (1980), BP (1980). Colorless to pale
yellow oil; specific gravity (25°/25°C) 1.038
to 1.060; optical rotation (20°C), -1° 30' to
0; refractive index (20°C), 1.527 to 1.535;
solubility (70 percent ethanol), 2 vol; total
phenols (as eugenol), min 85 percent by
volume.
Constituents Deyama and Horiguchi
(1971) investigated the chemical composi-
tion of clove bud oil and reported the follow-
ing constituents:
eugenol (80.87%)
eugenyl acetate (7 .33%)
a-ylangene (0.43%)
2-heptanone (0.07%)
caryophyllene (9 .12%)
a- & ~-humulene (1.66%)
m-methoxy benzaldehyde (0.39%)
benzyl alcohol (0.07%)
286 Source Book of Flavors
together with traces of benzylaldehyde and
chavicol. The BPC (1973) suggests that the
presence of furfural is probably the cause of
the oil darkening with age and of methyl
pentyl ketone as the source of the fruity
notes in the profile.
Oil of Clove Leaf Obtained by steam
distillation of clove leaves usually in the pro-
ducing area.
Specification in EOA No. 55, FCC II
(1972).
When freshly distilled, this is a very pale,
straw-colored oil, which rapidly darkens and
turns brown with age. It may become almost
black if in contact with iron. Such an oil
needs redistillation before use. Specific
gravity (25°/25°C), 1.036 to 1.046; optical
rotation (20°C), 0 to - 2°; refractive index,
1.531 to 1.535; solubility (70 percent
ethanol), 2 vol; total phenols (as eugenol),
84-88 percent by volume.
Oil of Clove Stem Obtained by the steam
distillation of clove flower stems gathered
with the spice at the time of harvesting.
Specification in EOA No. 176, FCC II
(1972).
Yellow to dark brown oil, depending on
age; specific gravity (25°/25°C), 1.048 to
1.056; optical rotation (20°C), -1.SO to 0;
refractive index (20°C), 1.534 to 1.538; solu-
bility (70 percent ethanol), 2 vol; total
phenols, 89 to 95 percent by volume.
Sensory Character The odor of both
clove leaf and clove stem oils is much less
fruity than the bud oil, although the rectified
leaf oil is more comparable. Generally, the
leaf and stem oils are coarser and less accept-
able than the distinctly fruit-spicy character
of the genuine bud oil. The profiles are
discussed by Heath (1978).
Oleoresin Clove
Derived from clove buds, although the
prime oleoresin may be subsequently
blended with clove stem and leaf oils to
satisfy specific demands. A brownish-green
to greenish-brown viscous to fluid oleoresin.
Three oleoresins are available commercially
(Table 7-46).
TABLE 7-46. Commercially available clove
oleoresins
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%)
70 6 4.2
70-76 6 4.2-4.56
90-95 10 9.0-9.5
Salzer (1975) recommends the deter-
mination of volatile oil content and sub-
sequent assay of eugenol content as the
measure of quality.
References: Clove
Deyama, T. and Horiguchi, T. 1971. Studies on
the components of essential oil of clove,
Eugenia caryophyllata, Thumberg. Yaku gaku
Zasshi 91:1383-1386.
Formacek, V. and Kubeczka, K.H. 1982.
Essential oils analysis by capillary chroma-
tography and carbon-13 NMR Spectroscopy.
New York: John Wiley & Sons.
Gaydou, E.M. and Randriamiharisoa, R.P.
1987. Multidimensional analysis of gas
chromatographic data, application to the dif-
ferentiation of clove bud and clove stem
essential oils from Madagascar. Perf Flav.
12(5) :45-51.
Gopala-Krishnan, M., Nirmala, M., and
Mathew, A.G. 1982. Changes in the com-
position of clove oil during maturation. J.
Food Sci. Techno!. India 19(5):190-192.
Gopalakrishnan, M., Narayanan, C.S., and
Mathew, A.G. 1984. Sesquiterpene hydro-
carbons from clove oil. Lebensm.-Wiss.
Techno!. 17(1):42-43.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn.,
A VI Publishing Co.
Imbert, M.P. 1983. The preservative properties
of spice extracts prepared from cinnamon,
clove and nutmeg. Proc. 6th Internat. Con-
gress Food Sci. Techno. 1:51-52.
Lawrence, B.M. 1977-1978. Progress in essen-
tial oils. Clove. (A monthly review). Perfum.
Flavorist 2(5):44-45; 3(4):56.
Mat-Isa, A. and Nazarifah, I. 1986. Quality
of clove bud and clove bud oil. MARDI-
Research-Bulletin 14(2): 148-153.
 Natural Flavoring Materials 287

Moyler, D. and Heath, H. 1988. Liquid Carbon
Dioxide Extraction of Essential Oils. In
Flavors and Fragrances: A World Perspective,
eds. B.M. Lawrence, Mookherjee, B.D. and
Willis, B.J. New York: Elsevier. pp. 41.
Muchalal [Mukhalal], M. and Crouzet, J. 1985.
Volatile components of clove essential oil
(Eugenia caryophyllus Spreng): neutral frac-
tion. Agric. Bioi. Chern. 49(6):1583-1589.
Narayanan-Gopalakrishnan, Shanti, P.P.V., and
Subrahmanian-Narayanan, C. 1990. Com-
position of clove (Syzygium aromaticum) bud
oil extracted using carbon dioxide. J. Sci.
Food Agric. 50(1):111-117.
Randriamiharisoa, R.P. and Gaydou, E.M.
1987. Sesquiterpenes of clove bud oil (Eugenia
caryophyllus Spreng) from Madagascar.
Lebensm. -Wiss. Techno/. 20(3):121-122.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavour Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Coriander
Coriander is the dried nearly ripe fruit of the
annual Umbelliferous plant ( Coriandrum
sativum L.), which is native to the
Mediterranean region and now cultivated in
many temperate countries.
Commercial Sources
Morocco, Romania, Argentina, France,
Italy, the Netherlands, Yugoslavia, the
former Soviet Union, Turkey, India,
Mexico. Much smaller quantities are pro-
duced in the United Kingdom and United
States.
much paler wavy, longitudinal ridges; there
is a depression at the base and 5 small teeth
(calyx) and a conical stylopodium at the
apex. The sizes are variable according to
source (Table 7-47).
Fixed Oil Content
About 13 percent.
Sensory Character
Warm, sweet, fruity odor; warmly spicy,
sweetly fruity flavor with slight floral back-
note.
Oil of Coriander
Specification in FCC II (1972), USP
XX (1980), BP (1980). Commercial sources
USSR, Poland and Hungary. A colorless to
pale yellow oil; specific gravity (25° /25°C),
0.863 to 0.875; optical rotation (20°C), +8°
to + 15°; refractive index, 1.462 to 1.472;
solubility (70 percent ethanol), 3 vol.
Constituents The results of various
investigations into the chemical composition
of coriander oil have been discussed by
Lawrence (1977, 1981/82, 1984). The results
of Taskinen and Nykanen (1975) are
presented in Table 7-48 together with
trace quantities of myristicin, a-thujene, a-
phellandrene, .il-3-carene, cis- and trans-
ocimene, heptadecane, nero!, geraniol,
octadecane and dodecanol.
TABLE 7-48. Chemical composition of coriander oil

Description a-pinene, (6.5%) camphene (0.39%)

~-pinene (0.27%) sabinene (0.15%)
Yellowish-brown globular schizocarps, myrcene (0.65%) y-terpinene (0.05%)
which readily split into two mericarps; 3- limonene ( 1. 7%) ~-phellandrene (0.05%)
5 mm in diameter with 8 straight and 10 y-terpinene (10.1%) p-cymene (3.7%)
terpinolene (0.1%) nonanal (0.07%)
TABLE 7-47. Sources and sizes of coriander linalool oxide (0.08%) decanal (0.31%)
linalool (65.0%) camphor (5.0%)
Fruits per Volatile Oil caryophyllene undecanal (0.06%)
Source Gram (avg.) Content(%) terpinen-4-ol (0.31%) trans-2-decanal (0.07%)
borneol (0.13%) a-terpineol
Russia 130 0.8-1.2 decanal dodecanal (0.46%)
Argentina 110 0.3-0.8 citronellol (0.02%) geranyl acetate (2.6%)
Morocco 75 0.3-0.6 geraniol (1. 7%) trans-2-dodecenal (0.44%)
 288 Source Book of Flavors
TABLE 7-49. Commercially available coriander
oleoresins
Volatile Oil Recommended Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%)
40 31.2
38-42 1.5 0.57-0.63
87-93 1.0 0.87-0.93
Oleoresin Coriander
Obtained by the extraction of imported
coriander seeds. The prime extract has a
high fixed oil content (about 90 percent) and
a low volatile oil content (about 5 percent),
which makes it an unstable source of this
flavor. Most commercial oleoresins are
blended with essential oil of coriander, the
amount present being determined by the
end use. Commercially available oleoresins
are shown in Table 7-49.
Salzer (1975) recommends the deter-
mination of the linalool content of the
recovered essential oil as a measure of the
flavoring quality.
References: Coriander
Formacek, V. and Kubeczka, K.H. 1982.
Essential Oils Analysis by Capillary Chroma-
tography and Carbon-13 NMR spectroscopy.
New York: John Wiley & Sons.
Haelvae, S., Hirvi, T., Maekinen, S., and
Honkanen, E. 1986. Yield and glucosinolate
of mustard seeds and volatile oils of caraway
seeds and coriander fruit. III. Yield and
volatile oils of coriander fruit ( Coriandrum
sativum L.). J. Agric. Sci. Fin. 58(4):169-173.
Lawrence, B.M. 1977. Progress in essential oils.
Coriander. (A monthly review). Perfum.
Flavorist 2(3):53-50.
Lawrence, B.M. 198111982. Progress in essential
oils. Perfum. Flavorist 6(6):43.
Lawrence, B.M. 1984. Progress in essential oils.
Perfum. Flavorist 9(2):23.
Macleod, A.J. and Islam, R. 1976. Volatile
flavour components of coriander leaf. J. Sci.
Food Agric. 27:721-725.
Mostafa, M.M., EI-Zalaki, M.E., Zaki, M.S.,
and Moussa, S.H. 1986. Quality attributes of
Egyptian coriander seeds and oils. Egypt. J.
Food Sci. 14(1):101-110.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavour Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Tashinen, J. and Nykanen, L. 1975. Volatile
constituents obtained by the extraction with
alcohol-water mixture and by steam distilla-
tion of coriander fruit. Acta Chern. Scand.
B29:425-429.
United Kingdom, British Standards Institution.
1990. Herbs and spices ready for food use.
Part 6. Specification for coriander seeds
(whole and ground). British-Standard; BS
7087: Part 6: 1990.
Cumin
Cumin is the dried ripe fruit of a small
annual Umbelliferous plant (Cuminum
cyminum L.), which is native to northern
Egypt and the Mediterranean region. There
is a distinct difference between the flavor
of cumin and its relative, caraway. The
Germans call both seeds "kummel"; the
French use the same word for cumin, but
caraway is "cumin des pres or carvi"; the
Spanish call cumin "camino" and caraway
"carvi."
Commercial Sources
Morocco, Cyprus, Egypt, India, Mexico and
China.
Description
A mixture of united and separated meri-
carps; light yellowish-brown, elongated-
ovoid; 3-6 mm in length. The surface has
5 primary ridges alternating with 4 less
distinct secondary ridges bearing numerous
short hairs. Some fruits have a short attached
stalk.
Volatile Oil Content
2-4.5 percent. Fixed oil content: About
10 percent.
Sensory character
Very strong, characteristic odor and warmly
aromatic flavor, somewhat reminiscent of
caraway.

Oil of Cumin
The major producers of cumin oil are
Spain (4 tons) and Egypt (3 tons). A small
amount of oil is also produced in the USSR,
Morocco and Algeria to total about 8 metric
tons per year (Lawrence 1985).
Specification in EOA No 1115, FCC II
(1972).
A colorless to pale yellow oil; specific
gravity (25°/25°C), 0.905 to 0.925; optical
rotation (20°C), +3° to +8°; refractive
index, 1.501 to 1.506; solubility (80 percent
ethanol), 8 vol: aldehydes (as cuminic
aldehyde), 45 to 52 percent.
Constituents There have been numer-
ous studies into the chemical composi-
tion of cumin (Varo and Heinz 1970;
Shankaracharya and Natarajan 1971;
Kumar and Baslas 1978; Lawrence 1980,
1987, El-Wakeil et al. 1986). The results of
Varo and Heinz (1970) are presented below.
a-pinene (0.5%)
myrcene (0.3%)
limonene (0.5%)
1,8-cineole (0.2%)
p-menth-3-en-7-al (0.7%)
p-mentha-1,3-dien-7-al (5.6%)
caryophyllene (0.8%)
B-bisabolene (0.9%)
B-pinene (13.0%)
p-cymene (8.5%)
B-phellandrene (0.3%)
Ll-terpinene (29 .5%)
cuminic aldehyde (32.4%)
cuminyl alcohol (2.8%)
B-farnesene (1.1%)
together with much smaller quantities of
a-phellandrene, a-terpinene, cis and
trans sabinene, myrtenol, a-terpineol and
phellandral.
The relative significance of components
to the odor and flavor profile was reported
by Tassan and Russell (1975), who con-
firmed that the characteristic cumin odor is
due principally to the aldehydes present
(i.e., cuminic aldehyde, p-menth-3-en-7-al
and p-mentha-1,3-dien-7-al).
Natural Flavoring Materials 289
TABLE 7-50. Commercially available cumin
oleoresins
Volatile Oil Recommended Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%)
50 5 2.5
65 5 3.25
63-70 2 1.26-1.40
Oleoresin Cumin
A brownish-yellowish-green fluid oleoresin.
The commercially available oleoresins are
shown in Table 7-50.
References: Cumin
El-Wakeil, F., Khairy, M., Morsi, S., Farag,
R.S., Shibata, A.A., and Badel, Z.M.A.
1986. Biochemical studies on the essential oils
of some fruits of the Umbelliferae family.
Siefen-0/e-Fette-Wachse 112:77-80.
Koedam, A., Scheffer, J.J.C., and Svendsen,
A.B. 1979. Comparison of isolation proce-
dures for essential oils. II. Ajowan, caraway,
coriander and cumin. Zeitsch. Lebensm.
Unter. Forsch 168(2): 106-111.
Kumar, P. and Baslas, R.K. 1978. Chemical
examination of essential oil of Cuminium
cuminium L. Indian Perf. 22(3):164-165.
Lawrence, B.M. 1976. Progress in essential
oils. Cumin. (A monthly review). Perfum.
Flavorist 1(3):45.
Lawrence, B.M. 1980. New trends in essential
oils. Prefum. Flav. 5(4):6-16.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Lawrence, B.M. 1987. Progress in essential oils.
Prefumer & Flavorist 12(2):67.
Shankarakutty, S., Sumathikutty, M.A., Bhat,
A.V., and Mathew, A.G. 1978. Studies on
extraction of oils and oleoresins from cumin,
fennel and fenugreek. lndian-Arecanut,
-Spices-&-Cocoa-1. 2(2):25-30.
Shankaracharya, N.B. and Natarajan, C.P. 1971.
Chemical composition and uses of cumin.
Indian Food Packer 25(6):22-28.
Tassan, C.G. and Russell, G.F. 1975. Chemical
and sensory studies on cumin J. Food Sci.
40:1185-1188.
Varo, P.T. and Heinz, D.E. 1970. Volatile
components of cumin seed oil. J. Agric. Food
Chern. 18:234-238.
290 Source Book of Flavors

Dill (1984) has studied the effect of growing

Dill is the dried ripe fruits of a small annual altitude on the composition of dill oils. A
or biennial herb (Anethum graveolens L.) comprehensive study on dill oil has been
indigenous to Egypt and the Mediterranean published by Brunke and Rojahn (1984),
region. Indian dill is derived from another their results are presented below.
species (Anethum sowa. Roxb.). All parts of
the plant are aromatic. In the United States, a-pinene (0. 77%)
Hungary, Poland and Bulgaria, the green toluene (trace)
herb, with seeds set but not yet ripened, is undecane (0.02%)
harvested and distilled to produce the oil of ~-pinene (0.04%)
dill weed, which is extensively used in the sabinene (0.06%)
pickling of cucumbers (dill pickle). Com- myrcene (0.06%)
mercial sources are the United Kingdom, a-phellandrene (20.62%)
India and the United States. dihydrocarvyl acetate (0.05%)
carvone (28.99%)
Description trans-carvyl acetate (0.02%)
Light brown, oval, united mericarps; 3- trans-~-ocimene (trace)
5 mm long, about 2 mm wide. Each mericarp p-cymene (1.66%)
has 3 well-defined longitudinal ridges and 2 terpinolene (0.07%)
pale yellowish-brown wing-like lateral ribs, cis-3-hexenol (trace)
which give it a very distinctive appearance. fenchone (trace)
u-p-dimethyl styrene (0.07%)
Volatile Oil Content cis-1, 2-limonene epoxide (0.04%)
2.5-4% (seeds) containing d-carvone trans-1, 2-limonene expoxide (trace)
(40-60%). 3, 9-epoxy-p-menth-1-ene (5.04%)
terpinen-4-ol (trace)
Sensory Character cis-dihydrocarvone (1.40%)
Sweetly aromatic odor; warm, sharp flavor trans-dihydrocarvone (0.05%)
slightly reminiscent of caraway. limonene (32.89%)
~-phellandrene (2.44%)
Oil of Dill Seed p-menthatriene (0.23%)
Approximately 2.5 metric tons of dill seed cis-~-ocimene (0.04%)
oil were produced worldwide, coming from y-terpinene (trace)
the USSR, Hungary, Poland, Bulgaria and isodihydrocarveol (0.52%)
Egypt in 1984 (Lawrence 1985). neoisodihydrocarveol (0.62%)
Specification in EOA No. 158 trans-carveol (0.06%)
(European oil), FCC II (1972) (European cis-carveol (0.08%)
oil), BP (1980). p-menth-1-en-9-ol (0.02%)
A pale yellow oil; specific gravity (25°/ carvacrol(0.04°/o)
25°C), 0.890 to 0.915; optical rotation epoxide myristicin (0.05%)
(20°C), + 70 to +82°; refractive index, 1.483
to 1.490; solubility (80 percent ethanol), 2 Oil of Indian Dill Seed
vol; ketones (as carvone), 42 to 60 percent. Obtained by the steam distillation of
Constituents The chemical composition crushed Indian dill (Anethum sowa Roxb.)
of dill seed oil has been reviewed by Specification in EOA No. 159 (Indian),
Lawrence (1981, 1985/1986). Pust (1976) FCC II (1972) (Indian).
has presented data on the composition of A pale yellow to light brown oil; specific
dill oils obtained from fruit, plant and roots gravity (25°/25°C), 0.925 to 0.980; optical
of dill grown in Germany. Huopalahti rotation, +40° to +58°; refractive index

(20°C), 1.486 to 1.495; solubility (90 percent
ethanol), 0.5 vol; ketones (as carvone) 20 to
30 percent.
Constituents Indian dill seed oil is dis-
tinguished from the European oil by the
presence of dillapiol in the former and its
almost total absence in the latter. The
chemical composition of Indian dill seed
oil (incorrectly identified as Anethum
graveolens) was investigated by Miyazawa
and Kameoka (1974), and their results are
presented below.
a-pinene (1.3%)
y-terpinene (0.1%)
terpinen-4-ol (0.1%)
cis-dihydrocarvone and caryophyllene
(0.8%)
trans-dihydorcarvone (16.6%)
trans-anethol and trans-carveol (0. 7%)
geraniol (0.2%)
limonene (5.9%)
decanal (0.2%)
P-elemene (0.1%)
carvone (20.9%)
dillapiole (52.5%)
together with much smaller quantities of
a-phellandrene, a-terpinene, p-cymene,
nonanal, P-terpineol, hydrocarveol, and
cis-carveol.
Oil of Dill Weed
In 1984, approximately 140 metric tons of
dill weed oil were produced worldwide. The
USA (70 tons), Hungary (35 tons) and
Bulgaria (20 tons) were the major producers
(Lawrence 1985).
Dill weed oil is obtained by the steam
distillation of freshly harvested tops of
European dill (Anethum graveolens).
According to Guenther (1948-1952), the
yield in the United States is about 20-30 lbs.
per acre.
Specification in EOA No. 58, FCC II
(1972) (American).
A pale yellow oil; specific gravity (25°/
25DC), 0.884 to 0.900; optical rotation,
(20°C), +84° to +95°; refractive index,
Natural Flavoring Materials 291
TABLE 7-51. CommerciaUy available dill oleoresins
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(mlllOOg) (%) (%)
10 4-6 0.4-0.6
70 5 3.5
60-65 2.5 1.5-1.62
The following dill weed oleoresin is also offered:
30-40 3 0.9-1.2
1.480 to 1.485; solubility (90 percent
ethanol), 1 vol with some opalescence;
ketones (as carvone), 28 to 45 percent.
Guenther quotes figures for ketones as low
as 12 percent, and the FCC notes that oils
obtained early in the season may show lower
figures for carvone, specific gravity, and
refractive index but higher figures for
optical rotation.
Oleoresin Dill
Obtained by the extraction of European dill
seed; the prime oleoresin contains fixed oil
(about 65 percent) and volatile oil (about 20
percent). Without the addition of a per-
mitted antioxidant this product has a poor
shelf life.
The oleoresin is a greenish to pale amber
fluid, depending on the degree of blending.
The oleoresins that are available com-
mercially are shown in Table 7-51.
Quality assessment Salzer (1975) has
discussed the quality evaluation of dill
oleoresin and concludes that the volatile
oil recovered is both a quantitative and
qualitative measure of the flavoring value.
The oils from European and Indian seeds
are readily distinguishable both organ-
oleptically and by GC.
References: Dill
Ateeque, A., Misra, L.N., and Nigam, M.C.
1990. A dihydrobenzofuran from Indian dill
seed oil. Phytochem 29(6):2035-2037.
Belafi-Rethy, K., Kerenyi, E., and Kolta, R.
1974. Composition of domestic and foreign
essential oils. III. Components of dill oil. Acta
Scient. Hung. 83(1):1-13. (Hungarian)
Belafi-Rethy, K., lglewski, S., and Kerenyi, E.
292 Source Book of Flavors
1971. Determination of the components of
several essential oils by gas chromatography
and spectrometry. Proc. 2nd Conf Physics
Chern. I:243-248.
Brunke, E.J. and Rojahn, W. 1984. The absolute
configuration of dill ether, an organoleptically
important constituent of dill. Dragoco Rept.
3:59-66.
Clark, R.J. and Menary, R.C. 1984. The effect of
harvest date on the yield and composition of
Tasmanian dill oil (Anethum graveolens L.).
J. Sci. Food Agric. 35(11):1186-1190.
Embong, M.B., Hadziyev, D., and Molnar, S.
1977. Essential oils from spices grown in
Alberta. Dill seed oil, Anethum graveolens L.
(Umbelliferae). Can. Inst. Food Techno!. J.
10:208-214.
Georgiev, E.V. eta!. 1978. On the changes of dill
oil during storage. Riv. /tal. Essenze Profumi
Piante Off. 60(5):307-313. (Italian)
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
Huopalahti, R. and Linko, R.R. 1983. Com-
position and content of aroma compounds in
dill, Aneth urn graveolens L., at three different
growth stages. J. Agric. Food Chern. 31(2):
331-333.
Huopalathi, R. 1984. Effect of latitude on the
composition and content of aroma compounds
in dill Anethum graveolens L. Lebensmitt.
Wissenschaft. Techno!. 17:16-19.
Huopalahti, R. 1985. The content and com-
position of aroma compounds in three dif-
ferent cultivars of dill, Anethum graveolens,
L. Zeitsch. Lebensm. Unters. Forsch 181(2):
92-96.
Huopalahti, R. 1983. Effect of latitude on the
composition and content of aroma compounds
in dill, Anethum graveolens. In Instrumental
Analysis of Foods, Vol. 1, eds. G. Chara-
lambous and G. Inglett, pp. 57. New York:
Academic Press.
Huopalahti, R., Kesaelahti, E., and Linko, R.
1985. Effect of hot air and freeze drying on
the volatile compounds of dill (Anethum
graveolens L.) herb. J. Agric. Sci. Finland
57(2):133-138.
Huopalahti, R. and Kesalahti, E. 1985. Effect of
drying and freeze-drying on the aroma of
dili-Anethum graveolens cv. Mammut. In
Essential oils and aromatic plants, eds. A.B.
Svendsen and J.J.C. Scheffer, pp. 179-184.
New York: Acedemic Press.
Huopalahti, R. 1986. Gas chromatographic and
sensory analyses in the evaluation of the
aroma of dill herb, Anethum graveolens L.
Lebensm.-Wiss. Techno!. 19(1):27-30.
Lawrence, B.M. 1977-1978. Progress in essen-
tial oils. Dill. (A monthly review). Perfum.
Flavorist 2(2):29-30; 2(5):46; 3(2):46.
Lawrence, B.M. 1981. Progress in essential oils.
Perfumer & Flavorist 6(1):37.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Lawrence, B.M. 1985/1986. Progress in essential
oils. Perfumer & Flavorist 10(6):29.
Miyazawa, M. and Kameoka, H. 1974. The
constitution of the essential oil of dill seed.
J. Japan. Oil Chern. Soc. 23(11):746-749.
(Japanese)
Paeaekkoenen, K., Malmsten, T., and
Hyvoenen, L. 1989. Effects of drying method,
packaging, and storage temperature and time
on the quality of dill (Anethum graveolens L. ).
J. Food Sci. 54(6):1485-1495.
Pundarikakshudu, K. and Bhavsar, G.C. 1990.
The effect of seed and foliar treatment of
ascorbic acid on the yield and composition of
Indian dill (Anethum sowa Roxb.). J. Essen.
Oil Res 2(3): 133-135.
Pust, U. 1976. Untersuchungen ber die Ather-
ischen Ole in wurzel Kraut und Fructen
verscheidener Seseleinae (A Piaceae). PhD
Thesis, University of Hamburg.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts ( oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Singh, A., Randhawa, G.S., and Mabey, R.K.
1987. Oil content and oil yield of dill
(Anethum graveolens L.) herb under some
agronomic practices. Acta. Horticult 208:51-
60.
Estragon
See Tarragon.
Fennel
Fennel is the dried ripe fruits of a tall
Umbelliferous plant (Foeniculum vulgare
Mill.), which is native to the Mediterranean
region but now grows in most temperate
countries. The whole plant is aromatic and
the fresh string-like leaves have a culinary
 Natural Flavoring Materials 293

value, both as a source of flavor and as a Sensory Character

garnish. Pleasantly aromatic, anise-like odor; strong
flavor that differs somewhat with variety
Commercial Sources and source.
France, Germany, Italy, India, Japan and There are two principal varieties of
the United States. fennel: "bitter" and "sweet." Bitter fennel
is a synonym for the most common variety.
Description Sweet fennel is also known as French or
Greenish to pale yellowish-brown, oval- Roman fennel and is derived from F.
oblong, united mericarps; 4-10 mm long, vulgare var. dulce (Mill.) Thellung. The
many with a small stalk attached; the sur- volatile oil from this variety contains no
face has 5 yellowish longitudinal ridges. fenchone and is more anisic and sweeter
in character than that of bitter fennel.
Volatile Oil Content Florence fennel is grown for its bulbous
2.5-6 percent containing about 50 percent stalk bases and is used as a vegetable.
of anethole and 20 percent of fenchone.
Oil of Fennel
Fixed Oil Content Bitter fennel oil is produced in Egypt,
About 10-20 percent. Portugal, Morocco, China, Argentina,

TABLE 7-52. Constituents of oil of fennel

Sample(%)

Compound 2 3 4

u-thujene + a-pinene 11.73 15.86 0.73 1.95

~-fenchene O.Q3 0.09 O.o2 0.06
alpha-fenchene 0.04 O.Q7
camphene 0.49 0.70 0.06 0.20
beta-pinene 1.63 4.15 0.06 0.59
sabinene 0.27 0.21 0.22 0.10
delta-3-carene 0.15 0.32 0.16
myrcene 1.80 3.13 0.11 0.87
alpha-phellandrene 3.48 10.88 1.96
alpha-terpinene 0.05 0.08 0.03
limonene 10.33 28.58 5.72 21.03
1,8-cineole + beta-phellandrene 1.61 3.44 0.27 0.51
cis-beta-ocimene 0.42 1.28 0.04 0.29
gamma-terpinene 1.28 0.36 0.10 0.31
trans-beta-ocimene 0.11 0.41 0.02 0.10
p-cymene 0.87 1.34 1.65 0.68
terpinolene 0.17 0.21 0.01 0.13
fenchone 14.65 11.80 9.04 7.99
camphor 0.21 0.13 0.20 0.16
linalool O.Ql 0.01 0.35
terpinen-4-ol 0.04 0.08 0.23
methyl chavicol 2.34 1.44 5.07 2.28
alpha-terpineol (?) 0.18 0.51 0.10
cis-anethole 0.16 0.08 0.24 0.73
trans-anethole 47.56 14.48 67.30 5.12
anisaldehyde 0.24 0.08 6.98 0.97
Legend: I. Hungarian fennel oil; 2. Spanish fennel oil; 3. Rectified fennel oil; 4. Sweet fennel oil.
294 Source Book of Flavors

TABLE 7-53. Commercially available fennel
oleoresins
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/lOOg) (%) (%)
50 5 2.5
52-58 1 0.52-0.58
Spain, Italy and China. Less than 5 metric
tons come from these countries annually.
Sweet fennel oil is primarily produced in
Spain, the USSR, Bulgaria and Italy. Small
quantities are produced in Australia, France
and Yugoslovia. Worldwide production
is estimated at 25 metric tons in 1984
(Lawrence 1985).
Specification in FCC II (1972).
A colorless to pale yellow oil, which may
crystallize and may require warming and
mixing before use; specific gravity (25/25 C),
0.953 to 0.97; optical rotation (20°C), + 12°
to +24°; refractive index (20°C), 1.528 to
1.538; solubility (90 percent ethanol), 1 vol.
Consituents Lawrence (1981) has
reviewed the composition of fennel oil.
Detailed reports on the composition of
fennel oil have been presented by Karlsen
et al. (1969), Paukov et al. (1971), Masada
(1976), Kraus and Hammerschmidt (1980),
and Formacek and Kubeczka (1982).
Formacek and Kubeczka (1982) have com-
pared the oils from Spain and Hungary as
well as the bitter, rectified and sweet oils
(Table 7-52).
Oleoresin Fennel
The commercially available oleoresins are
shown in Table 7-53.
References: Fennel
Abdullah, N. et al. 1978. The effect of fertilizer
treatments on yield of seed and volatile oil of
fennel (Foeniculum vulgare Mill.). Pharmazie
33(9):607-608.
Akguel, A. and Bayrak, A. 1988. Comparative
volatile oil composition of various parts from
Turkish bitter fennel (Foeniculum vulgare var.
vulgare). Food Chern. 30(4):319-323.
Embong, M.B., Hadziyev, D., and Molnar, S.
1977. Essential oils from spices grown in
Alberta. Fennel oil (Foeniculum vulgare var.
dulce). Can. J. Plant Sci. 57(3):829-837.
Formacek, K. and Kubeczka, K.H. 1982.
Essential Oils Analysis by Capillary Chromato-
graphy and Carbon-13 NMR Spectroscopy.
New York: John Wiley & Sons.
International-Standard; ISO 7927-1: 1987.
Fennel seed, whole or ground (powdered). I.
Bitter fennel seed (Foeniculum vulgare P.
Miller var. vulgare). Specification.
Karlsen, J., Baerheim Svendsen, A., Chingova,
B., and Zolotovitch, G. 1969. Studies on the
fruits of Foeniculum species and their essen-
tial oil. Planta Med. 17:283-293.
Kraus, A. and Hammerschmidt, F.J. 1980. An
investigation of fennel oils. Dragoco Rept.
(112):3-12.
Lawrence, B.M. 1979. Progress in essential
oils. Fennel. (A monthly review). Perfum.
Flavorist 4(5):10.
Lawrence, B.M. 1981. Progress in essential oils.
Perfum. Flavorist 6(2):59.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Masada, Y. 1976. Fennel oil, In Analysis of
essential oils by gas chromatography. New
York: Halsted Press.
Paukov, V.N. et al. 1971. Study of the essential
oils of Foeniculum officina/is by capillary
chromatography. Conf Proc. Inst. Organ
icheskoi Khimii AN SRR, Botanicheskii sad
AN MSSR Kishinev, USSR.
Shankarakutty, S., Sumathikutty, M.A., Bhat,
A., and Mathew, A.G. 1978. Studies on
extraction of oils and oleoresins from cumin,
fennel and fenugreek. Indian-Arecanut,
-Spices-&-Cocoa-J. 2(2):25-30.
Verghese, J. 1988. Fennel. Indian-Cocoa,
-Arecanut-&~Spices-J. 12(2):39-43.
Vladov, R. et al. 1964. Composition of Bulgarian
fennel oil obtained from the fruits of sweet
fennel (Foeniculum dulce Mill.). Riechst.
Aromen Korperpflegem. 14:350-351.
(German)
Fenugreek
Fenugreek is the dried seed of an annual
leguminous plant (Trigonella foenum-
graceum L.), which is thought to be native

to the Mediterranean region but is now
cultivated in many other countries, both as a
food crop and as a flavor component in
curry powders.
Commercial Sources
France, Germany, Morocco, Egypt, India
and the United States.
Description
Angular, oblong-rhomboidal seeds; brown-
ish-yellow in color with a deep furrow run-
ning obliquely across one side, 3-5 mm long
and 2-3 mm wide.
Volatile Oil Content
Less than 0.02 percent. Fixed oil content
7-10 percent.
Sensory Character
The freshly ground seed has a pleasant,
peculiar odor very reminiscent of maple.
The flavor of the alcoholic extract is
markedly meaty with a sweet maple-like
note and slightly burnt-sugar like.
Extract of Fenugreek
All the aroma and flavor components of
fenugreek are recoverable by alcoholic
extraction of the crushed seeds. The
desolventized extract is dark brown to
greenish-y~llow-brown and is a viscous fluid
to a soft paste, depending on the degree of
heat used in its preparation. Fenugreek
extract and/or an alcoholic tincture may be
used in the formulation of imitation maple
and rum flavorings as well as in sweet
pickles.
References: Fenugreek
Abd-El-Hamide, M.F., Atallah, R.K., Moussa,
Z.A. 1984. Chemical studies on Egyptian
fenugreek ( Trigonella foenurn-graecurn) seed.
Ann. Agric. Sci. -Ain-Shams-Univ 29(1):43-
60.
El-Mahdy, A.R. and El-Sebaiy, L.A. 1985.
Preliminary studies on the mucilages ex-
tracted from okra fruits, taro tubers, jew's
mellow leaves and fenugreek seeds. Food
Chern. 14(4):237-249.
Natural Flavoring Materials 295
El-Mahdy, A.R. and El-Sebaiy, L.A. 1985.
Proteolytic activity, amino acid composition
and protein quality of germinating fenugreek
seeds (Trigonella foenurn-graecurn L.). Food
Chern. 18(1):19-33.
Faruq, M.O., Alam, M.N., Hossain, M.E.,
Chowdhury, J.U., and Monzoor-i-Khuda, M.
1982. Investigations on Trigonella foeneurn-
graecurn (fenugreek) seed. Bangladesh-I. Sci.
Indust. Res. 17(3/4):246-251.
Giraron, P., Sauvaire, Y., Baccou, J.C., and
Bessiere, J.M. 1986. Identification of 3-
hydroxy-4,5-dimethyl-2(5H)-furanone in aro-
ma volatiles of fenugreek seeds (Trigonel/a
foenurn graecurn L.). Lebens.-Wiss. Techno/.
19(1):44-46.
Ginger
The ginger of the spice trade is the dried
rhizome of a tuberous perennial (Zingiber
officinale Roscoe) thought to be of Asiatic
origin, but now grown in almost all tropical
countries that have a rich well-watered soil.
The growing and harvesting of ginger differs
according to its end use, which may be: (a)
as a fresh root vegetable, (b) as the basis of
preserved or crystallized confectionery
ginger or (c) as a spice. The two former uses
require the rhizomes to be harvested while
the leaves are still green and the rhizomes
fleshy and free from woody tissues; the spice
ginger is harvested after the leaves have
withered, at which time the rhizomes are
relatively hard and woody.
Dried ginger is the form used as a spice.
The suitability of different varieties grown
in India has been discussed by Muralidharan
(1974) and Mathew (1989).
Commercial Sources
China, India (Cochin, Calicut), Sierra Leone
(so-called African), Nigeria, Jamaica, Japan
and Australia (Queensland).
Description
The characteristics of dried ginger differ
very considerably with source. The principal
varieties available are listed in Table 7-54.
Jamaican Ginger Laterally flattened
296 Source Book of Flavors

TABLE 7-54. Commercial grades of dried ginger

Average
Description Odor Volatile Oil
Source Character Content% v/w.

Cochin Light brown; partially strongly 2.2

peeled on the flattened lemony
sides; cork wrinkled
and very light brown.
Jamaican Light buff color; peeled delicately 1.0
clean, hard. aromatic,
spicy
African Very dark greyish- strongly 1.6
(Sierra brown; unpeeled, cork earthy,
Leone) tissues wrinkled. harsh
Nigerian Light color; usually strongly 2.5
split and partially aromatic,
peeled. camphoraceous
Chinese Pale brown; unpeeled. mildly 2.5
aromatic,
lemony
Japanese Pale, partially peeled; weakly 2.0
often limed. aromatic,
lemony
Australian Light brown; peeled strongly 2.5
and unpeeled. lemony

branched rhizomes ("races" or "hands");
7-15 em long, 1.5-6.5 em wide and about
1.5 em thick. The branches ("fingers") arise
from the upper surface of the rhizome,
thicken, and then diminish to terminate in a
stem-scar. Good-quality material is light
buff-colored, striated longitudinally. The
fracture is fibrous.
Indian (Calicut, Cochin) Ginger Smaller
"hands" with shorter branches; partially
scraped.
African Ginger Small and dark-colored,
the outer skin is not removed.
Volatile Oil Content
1-4 percent on a dry weight basis (Connell,
1970; Mathew 1989).
Oil of Ginger
The world production of ginger oil was
estimated to have been about 55 metric tons
in 1984. India and China produced circa 20
tons, while another 10-15 tons were pro-
duced in the USA and Europe. Minor
quantities were also produced in Sri Lanka,
Jamaica and South Africa (Lawrence 1985).
Ginger oil is obtained primarily from the
steam-distillation of dried African ginger.
Specification in EOA No 13, FCC II
(1972).
A light yellow to amber-yellow liquid;
specific gravity (25°/25°C), 0.871 to 0.882;
optical rotation (20°C), -28° to -45°;
refractive index, 1.488 to 1.494; solubility
(no requirement as the oil is only sparingly
soluble in alcohol); saponification value,
max 20.
Constituents Investigations into the
chemical composition of ginger oil have
been reviewed by Lawrence (1976). The
following constituents have been reported
as present: a-pinene, camphene, ~-pinene,
sabinene, .1-3-carene, myrcene, ~-phel­
landrene, limonene, tricyclene, zingiberene,
1,8-cineole (about 7 percent), borneol,
zingiberol, methyl heptanone, citral,
n-decylaldehyde, n-nonylaldehyde. More
recent work has been done by Chen (1987),
Chen and Ho (1988), Miyazawa and
Kameoka (1988) and Chen and Ho (1989).
The sensory character and chemical
composition of different ginger oils as well
 Natural Flavoring Materials 297

as those produced by super critical C0 2 collectively called gingerol (50-70 percent).

extraction have been described by Moyler
and Heath (1988). Terhune et al. (1975) has
reported that the sesquiterpenes are of
significance in the odor profile, particularly:
cis- and trans-~-sesquiphellandrol, sesqui-
thujene, cis-sesquisabinene hydrate and
zingiberenol. Bednarczyk and Kramer
(1975) have noted that four peaks could
be used to characterize ginger oil: peak 1:
a-terpineol, neral and geraniol; peak 2:
~-sesquiphellandrene. and ar-curcumene;
peak 3: nerolidol; and peak 4: ~­
sesquiphellandrol.
Oleoresin Ginger
Obtained by the extraction of dried ginger
with acetone, alcohol, super critical C0 2 or
other appropriate solvent, which is sub-
sequently removed. The source of the
ginger is usually designated in the title. The
production of ginger oleoresin has been
described by Lewis et al. (1972) and by
Lewis (1973). The oleoresin varies within
narrow limits and on average contains
volatile oil (20-30 percent), fixed oil (about
10 percent), pungent resinous constituents
Specification in EOA No 243, BPC
1968.
A dark brown very viscous oleoresin. The
EOA specification requires volatile oil 18 to
35 ml per 100 g having an optical rotation of
-30° to -60° and RI of 1.488 to 1.497
(Table 7-55).
Constituents Oleoresin ginger has three
main groups of components: (a) volatile oil
responsible for the aroma, (b) nonvolatile
components responsible for the pungency
and (c) nonvolatile nonpungent substances.
The constituents of the volatile oil have
already been noted. The pungency of ginger
has been under investigation for at least the
past 60 years, but only recently have specific
conclusions been reached as to the chemical
nature of the compounds responsible. It has
long been held that the pungency is due to
the following related keto-alcohols together
with zingerone (Connell 1970):
(CH 2 ),CH 3
(CH,),CH,
+H 20

TABLE 7-55. Characteristics of ginger oleoresins

OH OH
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion Gingerol Shogaol
(ml/100 g) (%) (%) (where n = 4,6, or 8)
(Connell and Sutherland 1969)
African Ginger
min 25 3.75 min 0.94 (CH,),CH,
30-38 5 1.5-1.9
30-40 4-6 1.2-2.4
25-35 6 1.5-2.1 +C,H,OH +CH,(CH,),CHO
(alcoholic
extract)
Jamaican Ginger
min 25 2.5 min 0.63 OH
25-35 4 1.0-1.4 OH
30-35 4-6 1.2-2.4 Paradol Zingerone
23-35 6 1.38-2.1
(alcoholic
Connell (1970) has discussed the chem-
extract)
istry of oleoresin ginger and the changes
No designated source which take place during post-harvest prep-
30 4 1.2
min 25 3.5 min0.8
aration and ultimate extraction. The fresh
rhizomes contain only the most pungent
298 Source Book of Flavors
component, gingerol. During drying, this
compound loses water and part of it is
changed to shogaol, which has less pun-
gency. During any extraction a further
degradation takes place leading to the
formation of paradol and zingerone, all
of which reduces the original pungency.
Connell (1969) and Connell and Sutherland
(1969) reported that in ginger oleoresin the
ratio of the compounds gingerol/shogaol/
zingerone was 60/30/10.
Quality Assessment From a flavor point
of view, oleoresin ginger has two prime
attributes-essential oil content and pun-
gency. The assessment of these attributes is
discussed by Salzer (1975), who concluded
that the determination of the volatile oil
content followed by GC determination of
citral, zingiberene, ~-sesquiphellandrene
and ar-curcumene was the best method
of evaluating the flavoring quality; the
methoxyl content is suggested as a measure
of the pungency, although more precise
methods for the determination of pun-
gent components have been described by
Ananthakrishna and Govindarajan (1974),
Baranowski (1982), Chen, Rosen and Ho
(1986) and Chen, Kuo and Ho (1986). The
determination of the water content of the
oleoresin is also suggested (0.5-1 percent).
References: Ginger
Ananthakrishna, S. and Govindarajan, V. 1974.
The determination of the principles of ginger.
Lebensm. Wissen. Techno/. 7:220
Bednarczyk, A.A. and Kramer, A. 1975. Iden-
tification and evaluation of the flavor signi-
ficant components of ginger essential oil.
Chern. Senses Flavor 1:377-386.
Baranowski, J.D. 1986. Changes in solids,
oleoresin, and (6)-gingerol content of ginger
during growth in Hawaii. Hort Sci. 21(1):145-
146.
Baranowski, J.D. 1985. High-performance liquid
chromatographic separation of pungency
components of ginger. J. Chromatog. 319(3):
471-474.
Beek, T.A.-van, Posthumus, M.A., Lelyveld,
G.P., Phiet, H.V., and Yen, B.T. 1987.
Investigation of the essential oil of Viet-
namese ginger. Phytochem 26(11):3005-3010.
Chen, C.C., Kuo, M.C., Wu, C.M., and Ho,
C.T. 1986. Pungent compounds of ginger
(Zingiber officinale Roscoe) extracted by
liquid carbon dioxide. J. Agric. Food Chern.
34(3):477-480.
Chen, C.C. and Ho, C.T. 1987. Gas chromato-
graphic analysis of thermal degradation
products of gingerol compounds in steam-
distilled oil from ginger (Zingiber officinale
Roscoe). J. Chromatog. 387:499-504.
Chen, C.C. 1987. Studies on ginger oil (Zingiber
officinale Roscoe) extracted by liquid carbon
dioxide. Dissertation-Abstracts-Internal. -B;
48(3):608-609: Order no. DA8714461,
208pp.
Chen, C.C., Rosen, R.T., and Ho, C.T. 1986.
Chromatographic analysis of gingerol com-
pounds in ginger ( Zingiber officinale Roscoe)
extracted by liquid carbon dioxide. J. Chro-
matog. 360(1):163-173.
Chen, C.C., Kuo, M.C., and Ho, C.T. 1986.
High performance liquid chromatographic
determination of pungent gingerol com-
pounds of ginger (Zingiber officinale Roscoe).
J. Food Sci. 51(5):1364-1365.
Chen, C.C., Kuo, M.C., Wu, C.M., and Ho,
C.T. 1988. Studies on ginger oil extracted by
liquid carbon dioxide. Food Sci. China
13(3/4): 188-197.
Chen, C.C. and Ho, C.T. 1988. Gas chromato-
graphic analysis of volatile components of
ginger oil (Zingiber officinale Roscoe) ex-
tracted with liquid carbon dioxide. J. Agric.
Food Chern. 36(2):322-328.
Chen, C.C. and Ho, C.T. 1989. Volatile com-
pounds in ginger oil generated by thermal
treatment. In Thermal Generation of Aromas
ACS Symp. Ser. 409, eds. T.H. Parliment,
R.J. McGorrin, and C.-T. Ho, 366-375.
Washington, D.C.: American Chemical
Society.
Connell, D.W. 1970. The chemistry of the
essential oil and oleoresin of ginger (Zingiber
officinale Roscoe). Flav. Ind. 1(10):677-693.
Connell, D.W. and Sutherland, M.D. 1969.
A re-examination of gingerol, shogaol and
zingerone, the pungent principles of ginger
( Zingiber officinale Roscoe). Aust. J. Chern.
22:1033-1043.
Connell, D.W. 1969. The extraction of ginger.
Food Techno/. Austr. 21:570.
Damayanthi, K.S., Radha, R., and

Kalyanaraman, V. 1982. Volatile oil and
oleoresin from fresh ginger. In Proceedings
of the National Seminar on Ginger and
Turmeric, eds. M.K. Nair, T. Premkumar,
P.N. Ravindran, and Y.R. Sarma, pp. 194-
197. Calicut: MM Press.
Farthing, J.E. and O'Neill, M.J. 1990. Isolation
of gingerols from powdered root ginger by
countercurrent chromatography. J. Lig.
Chromatog. 13(5):941-950.
Kandiah, M. and Spiro, M. 1990. Extraction of
Ginger rhizome: kinetic studies with super-
critical carbon dioxide. Internal. J. Food Sci.
Techno/. 25(3):328-338.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Lawrence, B.M. 1984. Major tropical spices-
Ginger (Zingiber officinale Rose.). Perf. Flav.
9(5):1-40.
Lawrence, B.M. 1976-1978. Progress in essen-
tial oils. Ginger. (A monthly review). Perf.
Flav. 1(1):2; 1(6):32; 2(5):46.
Lee, Y.B., Kim, Y.S., and Ashmore, C.R. 1986.
Antioxidant property in ginger rhizome and
its application to meat products. J. Food Sci.
51(1):20-23.
Lewis, Y.S., Mathew, A.G., Nambudiri, E.S.,
and Krishnamurthy, N. 1972. Oleoresin
ginger. Flav. Ind. 3(2):78-81.
Lewis, Y.S. 1973. The importance of selecting
the proper variety of a spice for oil and
oleoresin extraction. Trop. Prod. Inst. Conf.
Proc., London.
Macleod, A.J. and Pieris, N.M. 1984. Volatile
aroma constituents of Sri Lankan ginger.
Phytochem. 23(2):353-359.
Mathew, A.G. 1989. Oil and Oleorosin from
Indian Spices. In Chemistry Analysis and
Structure: Proceedings of 11th International
Congress Essential oils, fragrances and flavors,
eds. S.C. Bhattacharyya, N. Sen, and K.L.
Sethi.
Miyazawa, M. and Kameoka, H. 1988. Volatile
components of Zingiberis rhizoma (Zinigiber
officinale Roscoe) Agric. Bioi. Chern. 52:
2961-2963.
Moyler, D.A. and Heath, H.B. 1988. Liquid
carbon dioxide extraction of essential oils. In
Flavors and Fragrances: Proceedings of the
lOth International Congress of Essential Oils,
eds. B.M. Lawrence, B.D. Mookherjee, and
B.J. Willis. Amsterdam: Elsevier.
Muralidharan, A. 1974. Suitability of different
Natural Flavoring Materials 299
varieties of ginger for the spice trade. Devel-
opment and Prospects of Spice Industry in
India. Symp. Proc. Mysore, India, Mar. 1974.
Paulose, T.T. 1973. Ginger cultivation in India.
Trop. Prod. lnst. Conf. Proc., London.
Pooter, H.L., de, Coolsaet, B.A., Dirinck, P.J.,
and Schamp, N.M. 1985. GLC of the head-
space after concentration on Tenax GC and of
the essential oils of apples, fresh celery, fresh
lovage, honeysuckle and ginger powder. In
Essential Oils and Aromatic Plants, eds. A.B.
Svendsen and J.J.C. Scheffer, pp. 67-77.
Netherlands: Martinus Nijhuff.
Salzer, U.-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:151-157. 11./bid. 6:206-210. III.
Ibid. 6:253-258.
Shanthi, N. and Govindarajan, V.S. 1978.
Evaluation of spices and oleoresin-VI-
pungency of ginger components, gingerols
and shogaols and quality. J. Food Techno/.
13(1):31-36.
Smith, R.M. 1982. Analysis of the pungent
principles of ginger and grains of paradise by
high-performance liquid chromatography
using electrochemical detection. Chromatog.
16:155-157.
Spiro, M., Kandiah, M., and Price, W. 1990.
Extraction of ginger rhizome: kinetic studies
with dichloromethane, ethanol, 2-propanol
and an acetone-water mixture. lnternat.
J. Food Sci. Techno/. 25(2):157-167.
Suga, T. and Sakamura, W. 1988. Development
and use of active principles of spices. Ginger.
Up-to-Date-Food-Processing-[Shokuhin-Kai-
hatsu); 23(6):36-39.
Terhune, S.J., Hogg, J.W., Bromstein, A.C.,
and Lawrence, B.M. 1975. Four new sesqui-
terpene analogs of common monoterpenes.
Can. J. Chern. 3:3285-3293.
Wood, A.B. 1987. Determination ofthe pungent
principles of chillies and ginger by reversed-
phase high-performance liquid chromato-
graphy with use of a single standard substance.
Flav. Frag. J. 2(1):1-12.
Yusof, N. 1990. Sprout inhibition by gamma
irradiation in fresh ginger (Zingiber officinale
Roscoe). J. Food Proc. Pres. 14(2):113-122.
Zamora, Z.G. and Valle, M.J.-del. 1981.
Extraction and evaluation of oleoresin from
fresh and dried ginger (Zingiber officinale
Roscoe). Up-Home-Econ. J. 9(1):11-18.
300 Source Book of Flavors
Grains of Paradise
Grains of Paradise, Guinea grains or
Melegueta pepper are the seeds of an
herbaceous perennial (Aframonum mele-
gueta (K.) Schum or A. granumparadisi (K.)
Schum), which grow in West Africa. The
plants are closely related to cardamom. The
seeds are borne in orange-red capsules.
Commercial Source
Ghana.
Description
Reddish-brown, pyramid-shaped seeds with
a shiny surface; the seed-stalk scar shows as
a paler area at one end.
Volatile Oil Content
0.5 to 1 percent. The oil is not distilled
commercially.
Sensory Characters
Slight but pleasing aromatic odor; very
agreeable flavor and a marked pungency.
Mace
See Nutmeg/Mace.
Marjoram, Sweet
Marjoram is the dried leaves and floral
parts of Majorana hortensis Moench, (also
classified as Origanum majorana L.), an
herb which is native to southern Europe and
the Mediterranean region. It is now widely
cultivated throughout Europe, North
Africa, India and both North and South
America.
Commercial Sources
Southern France, Germany, Romania,
Hungary, Greece, Tunisia and the United
States.
Description
The dried broken herb consists of whole and
broken pale grayish-green, elliptical leaves
covered on both surfaces with fine whitish
hairs. Numerous oil glands are visible under
a hand lens. Whole and/or broken floral
parts may be present.
Volatile Oil Content
0.3 to 1 percent.
Sensory Character
Sweet marjoram is pleasantly aromatic
and fragrant; the flavor is warmly spicy,
herbaceous but not overly green with a
bitter, slightly pungent back-note.
Oil of Sweet Marjoram
Commercial sources of marjoram oil are
Morocco, Egypt, Tunisia, Bulgaria, Spain,
South Africa, Hungary and Italy. World
production was estimated to be about 30
metric tons (Lawrence 1985).
Obtained by distillation of the dried
herb. The oil recovered from Spanish or
Portuguese marjoram is different and is de-
scribed under Origanum (Wild Marjoram).
Specification in EOA No 76.
A yellow to greenish-yellow oil; specific
gravity (25°/25°C), 0.890 to 0.906; optical
rotation (20°C), + 14° to +24°; refractive
index (20°C), 1.470 to 1.475; solubility (80
percent ethanol), 2 vol; acid value, max 2.5;
saponification value, 23 to 40; saponification
value after acetylation, 68 to 86.
Constituents The composition of mar-
joram oil has been reviewed by Lawrence
(1976, 1984). Granger et al. (1975) inves-
tigated the chemical composition of mar-
joram oils and concluded that two types
may be distinguished, depending on their
content of either cis-sabinene hydrate or
terpen-4-ol as the main constituent of the
oil. Lawrence (1976) considered these com-
pounds to be biogenetic variations and has
drawn attention to the findings of Salehiana
and Netieng (1973). The compounds that
have been reported as present by Lawrence
(1984) are shown in Table 7-56.
Nykanen (1986) has reported on the vola-
tiles in marjoram oil grown in Finland. The
composition of an alcoholic co-distillation of
marjoram herb was reported by the same
workers.
 Natural Flavoring Materials 301

TABLE 7-56. Constituents of marjoram oils TABLE 7-57. Commercially available marjoram
oleoresins
North American
Marjoram Oils Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
Compound A B c (ml/100g) (%) (%)
a-pinene 0.8 0.6 0.7 4-10 7-9 0.28-0.9
f3-pinene 0.1 0.2 0.3 20-25 5 1.0-1.25
sabinene 1.7 2.9 4.9 40 3 1.2
myrcene 1.0 0.8 0.8 40-45 3 1.2-1.35
a-phellandrene 0.3 0.3 trace
a-terpinene 6.2 3.0 0.9
limonene 0.7 0.8 0.8
f3-phellandrene 2.8 1.1 0.9 Original composition of marjoram flavor and
1,8-cineole its changes during processing. J. Agric. Food
cis-ocimene 0.3 0.1 trace Chern. 36(5):996-1003.
y-terpinene 10.0 7.6 2.4 Fischer, N., Nitz, S., and Drawert, F. 1987.
trans-ocimene
p-cymene
Original flavour compounds and the essential
2.5 3.5 2.5
terpinolene 3.1 1.3 0.7 oil composition of marjoram (Majorana
a-p-dimethylstryrene trace trace trace hortensis Moench). Flav. Frag. J. 2(2):55-61.
trans-sabinene hydrate 4.2 0.7 7.6 Gecan, J.S., Bandler, R., Glaze, L.E., and
linalool 15.3 8.9 38.9 Atkinson, J.C. 1986. Microanalytical quality
cis-sabinene hydrate of ground and unground marjoram, sage and
cis-p-menth-2-en-1-ol 2.3 2.4 1.6 thyme, ground allspice, black pepper and
linalyl acetate 2.0 2.4 2.9 paprika. J. Food Protection. 49(3):216-221.
terpinen-4-ol 29.0 48.2 18.1 Granger, R., Passet, J., and Lamy, J. 1975. On
caryophyllene 1.0 2.8 1.1 the essences called "marjorlaine." Riv. Ita/.
trans-p-menth-2-en-1-ol 0.6 1.4 0.4
terpinen-4-yl acetate Essenze Profumi Pianti Off. 57:446-454.
3.0 0.2 trace
a-humulene trace 0.2 trace (French)
a-terpineol 7.0 7.1 4.3 Koller, W.D. 1986. Influence of the extraction
a-terpinyl acetate 0.6 0.7 0.1 conditions of C0 2 high-pressure extraction on
neryl acetate 0.1 0.4 trace composition of the head-space gas and odour
bicyclogermacrene 2.8 0.9 0.1 of the extracts of comminuted marjoram.
trans-piperitol Lebensm.-Wissen. Techno/. 19(1):56-58.
geranyl acetate 0.1 0.6 trace Lawrence, B.M. 1984. Progress in essential oils.
trans-anethole trace trace trace Marjoram oil. Perf. Flav. 9(1):49.
p-cymen-8-ol trace 0.3 0.1 Lawrence, B.M. 1976-1977. Progress in essen-
caryophyllene oxide 0.2 0.1 0.3
spathulenol tial oils. Marjoram. (A monthly review). Perf.
0.8 trace 0.9
elemol 0.1 0.2 trace Flav. 1(2):18; 1(6):33-34; 2(2):31.
Lawrence, B.M. 1985. Essential oils-World
production. Perfum. Flavorist 10:1-16.
Nykanen, I. 1986. High resolution gas
Oleoresin Marjoram chromatographic-mass spectrometric deter-
A dark green viscous to pasty oleoresin. mination of the flavour composition of mar-
The commercially available oleoresins joram (Origanum mariorma L. ) cultivated
are shown in Table 7-57. in Finland. Z. Levbensm. Unters Forsch.
182:267-272.
Oberdieck, R. 1990. Marjoram. Fleischwirtschaft
References: Marjoram, Sweet 70(4):391-428.
Dent, R.G. and Glaze, L. 1985. Extraction of Oberdieck, R. 1983. Analysis of volatile aroma
light filth from unground marjoram: Col- substances in herbs and spices, e.g., mar-
laborative study. J. Assoc. Offic. Anal. Chern. joram. Fleischwirtschaft 63(10): 1631-1634.
68(5):899-901. Ravid, U., Bassat, M., Putievsky, E., Ikan, R.,
Fischer, N., Nitz, S., and Drawert, F. 1988. and Weinstein, V. 1987. Determination of the
 302 Source Book of Flavors

enantiomeric composition of ( +)-terpinen-4- Various mints are available in the dried

ol from sweet marjoram Origanum majorana broken form, which consist of dark green
L. using a chiral lanthanide shift reagent. crumpled, shriveled whole and/or
broken
Flav. Frag. J. 2(1):17-19. leaves. The aroma and flavor of the dried
Salehiana, A. and Netieng, G. 1973. The essen-
herb bears little resemblance to that of the
tial oil of marjoram from Provence (com-
parison with oils from other sources). Trav. fresh herb.
Soc. Pharm. Montpellier. 33:329-334.
(French) Reference: Mint, Culinary
Taskinen, J. 1974. Composition of the essential Lawrence, B.M. 1976. Progress in essential oils.
oil of sweet marjoram obtained by steam dis- Mint (A monthly review.) Perf. Flav. 1(1):3;
tillation and by extraction and distillation with 1(2):18; 1(5):12.
alcohol-water mixture. Acta Chern. Scand.
B28: 1121-1128. Mustard
Vernon, F., Richard, H., and Sandret, F. 1978. Mustard is the seed of
several species of
Marjoram essential oil (Majorana hortensis
the family Cruciferae, which includes such
Moench.) in Egypt. Perfum. Cosmet. Aromes
21(May/June):85-88. (French) vegetables as cabbage, cauliflower, turnip,
swede, radish, horseradish, watercress, etc.
Marjoram, Wild A pungent flavor is associated with many of
See Origanum. these substances, due in most cases to the
presence of sulfur compounds. The main
Mint, Culinary commercial varieties are:
Domestically grown mints represent a very
wide spectrum of varieties and strains, the White (or yellow) mustard-Sinapis alba L.
following being the main species involved: (or Brassica alba Boissier).
Black (or brown) mustard-Brassica nigra
M. viridis L. (Garden mint) (L.) Koch.
M. rotundifolia L. (Apple mint) Indian mustard-Brassica juncea (L.)
M. gentilis var. variegata (American apple Cosson (or Hook. and Thoms.)
mint)
M. spicata var. crispata (Curly mint) The plants are native to Europe and are
now widely cultivated throughout Europe,
The flavoring characteristics of these India, North Africa and both North and
various mints show considerable variation, South America, which provide the main
depending on source, environment during commercial sources.
growth, time of harvesting, postharvest
handling conditions, etc. The nature of the White Mustard
aromatics present is considerably changed A herbaceous annual plant, which grows to
by drying and the broken herb available for about 60 em (2ft.) in height, bears bright
domestic use bears little resemblance to yellow flowers that develop into cylindrical
the freshly picked leaves. Mint is widely hairy pods filled with yellowish seeds.
appreciated as a flavorful jelly or vinegar- Description Roughly globular, hard,
based sauce for use with certain meats, yellowish seeds 2 mm in diameter; the seed-
potatoes and peas. Normally, a fresh sprig coat, though apparently smooth, is minutely
of mint contains an essential oil that is still in pitted; odorless even when crushed in the
the process of developing, so that the flavor presence of water; mucilagenous when
obtained from it will be very different from soaked in water. The taste is pungent.
that of the mature leaf. An essential oil Constituents White mustard seeds con-
distilled from immature mint leaves is not tain: fixed oil (about 30 percent), mucilage
stable and changes rapidly in aromatic in the seed-coat and proteins (about 25
profile. It is not available commercially. percent), but no starch. The pungency is
 Natural Flavoring Materials 303

due to the presence of a crystalline glycoside The chemistry of this enzymatic reac-
sinalbin which is decomposed by the enzy- tion has already been discussed in an
matic action of myrosin in the presence of earlier section. Further details may be
water: found in reviews by MacLeod (1970),
Shankaranarayana et al. (1972), Schutte
(1974) and Shankaranarayana et al. (1982).
Mustard Oil
+ C"H,20,;+
glucoseMustard oil may be obtained by the distilla-
C,"H2.NO,, tion of a warm aqueous macerate of com-
HSO. minuted black mustard seed press-cake.
p-hydroxy benzyl acid sinapine Commercially, most "mustard oil" is
iso-thiocyanate sulfate
prepared synthetically and this is included in
the title.
p-Hydroxy benzyl iso-thiocyanate is a Specification in FCC III (1981).
yellow oily liquid having a very strong A colorless to pale yellow oil having
pungency and is a vesicant. an intensely irritating and pungent odor.
It contains not less than 93 percent of
Black Mustard allyl iso-thiocyanate, determined by the
A herbaceous plant, which grows to about method described in the FCC based on the
1m (3ft.) in height with a mass of small reaction of the iso-thiocyanate radical with
yellow flowers that produce four-sided pods silver nitrate. Other methods have been
having a sharp beak. The pods contain 10- described in the literature (Latrasse and
12 dark brown seeds. Vangheesdaele 1972; Shankananarayana
Description Roughly globular, hard, et al. 1972; Suntag and Kainz 1976).
reddish-brown to almost black seeds about 1 In view of its intensely irritating and
to 1.5 mm in diameter (smaller than white lachrymatory nature, every precaution
mustard seed); the seed-coat is minutely should be taken in handling mustard oil and
pitted. The dried seeds are odorless, but no attempt made to evaluate it other than in
when crushed in the presence of water they dilution.
quickly produce a strongly irritating and
Indian Mustard
pungent odor of allyl iso-thiocyanate.
The plant is similar to that of black mustard,
The taste is initially bitter, but almost
but the seeds are larger and browner. This
immediately intensely pungent.
species is cultivated in the southern USSR
Constituents Black mustard seeds con-
and India.
tain: fixed oil (about 28 percent), proteins
(about 30 percent), together with some References: Mustard
mucilage. The pungency is due to the Anon 1970. Mustard. Flav. Ind. 1(9):596-598.
presence of the glycoside sinigrin which, Bhalla, K. and Punekar, B.D. 1975. Incidence
in the presence of water, is decomposed and state of adulteration of commonly con-
enzymatically by myrosin to give allyl iso- sumed spices in Bombay city. II. Mustard,
thiocyanate. The seeds contain 0.5 to 1 black pepper, and asafoetida. Indian J. Nutri.
percent of volatile oil calculated as allyl Dietetics 12(7):216-222.
iso-thiocyanate: Chikkaputtaiah, K.S., Shankaranarayana, M.L.,
and Natarajan, C.P. 1971. Volumetric deter-
?·SOa·K
mination of allyl isothiocyanate in black
CoH,,O,·SoC:NCH,CH:CH,
mustard (Brassica nigra). Flav. Ind. 2(10):
"' ----CH,:CH·CH2·NCS + C.H,.O. + KHSO, 591-593.
N·O·SO,.·K Freeman, G.G. and Mossadeghi, N. 1972.
II
CoH, ,O,·S·C·CH,CH:CH, Influence of sulphate nutrition of flavour com-
sinigrin allyl iso·thiocyanate ponents of three cruciferous plants: radish
304 Source Book of Flavors
(Raphanus sativus), cabbage (Brassica
oleracea capitata) and white mustard (Sinapis
alba). J. Sci. Food Agric. 23(3):387-402.
Germany, Federal Republic of, Bundesgesund-
heitsamt 1989. Analysis of foods. Determina-
tion of the content of allyl mustard oil in
mustard. 2 pp. Berlin; Beuth Verlag GmbH.
Kishima, 1., Shibata, Y., and Ina, K. 1970.
Volatile components of Japanese horseradish
and black mustard. J. Food Sci. Techno!.
[Nihon Shokuhin Kogyo Gakkaishi] 17(8):
361-363.
Klepacka, M., Rutkowski, A.; Cwalina, A. 1983.
Characteristics of thioglucosidase from white
mustard and rapeseeds. Acta Alimentaria
Polonica. 9(114):23-29.
Kojima, M.; Hamada, H., and Toshimitsu, N.
1986. Comparison of volatile sulphur com-
pounds in the hydrolysates of wasabi, horse-
radish and black mustard on the market. J.
Japan. Soc. Food Sci. Techno[. [Nippon
Shokuhin Kogyo Gakkaishi]. 33(3):199-205.
Latrasse, A. and Vangheesdaele, G. 1972.
Determination of allyl cyanide in mustard
paste. Ann. Falsif. Expert. Chim. 65(697):
29-36.
MacLeod, A.J. 1970. The chemistry of vegetable
flavour. Flavour Ind. 1:665-672.
Peterka, S. and Fenwick, G .R. 1988. The use of
flash chromatography for the isolation and
purification of glucosinolates (mustard oil
glycosides). Fett Wissenschaft Techno/. 90(2):
61-64.
Raghavan, B., Shankaranarayana, M.L.,
Nagalakshmi, S., and Natarajan, C.P. 1971.
Volumetric determination of p-hydroxybenzyl
isothiocyanate in sinalbin (p-hydroxy-
benzylglucosinolate) and in white mustard
seed (Sinapis alba L.) J. Sci. Food Agric.
22(10):523-525.
Schutte, L. 1974. Precursors of sulfur-containing-
compounds. C.R.C. Crit. Rev. Food Techno/.
pp. 457-506.
Shankaranarayana, M.L., Nagalakshmi, S.,
Raghavan, B., and Natarajan, C.P. 1971.
A titrimetric method of determination of
p-hydroxybenzyl isothiocyanate in white
mustard (Sinapis alba L.). Agric. Bio. Chern.
35(6):959-961.
Shankaranarayana, M.L. et al. 1972. Mustard-
varieties, chemistry, analysis. Lebensm. Wiss.
Techno[. 5:191-197.
Shankaranarayana, M.L., Nagalakshmi, S.,
Raghavan, B., and Natarajan, C.P. 1972.
Oxidometric method of determination of allyl
isothiocyanate in black mustard (Brassica
nigra L.) with chloramine-T. Flav. Ind. 3(2):
75-77.
Shankaranarayana, M.L., Raghaven, B.,
Abraham, K.O., and Natarajan, C.P. 1982.
Sulphur compounds and flavours. In Food
Flavours. Part A. Introduction, eds. I.D.
Morton and A.J. MacLeod, pp. 169-281.
New York: Elsevier.
Suntag, G. and Kainz, G. 1976. Contribution to
the analysis of preservatives. Determination
of iso-thiocyanates. Mikrochim. Acta 1(1 ):
107-112. (German)
Szakacs, Dobozi M., Halasz, A., Kozma,
Kovacs, E., and Szakacs, G. 1988. Enhance-
ment of mustard oil yield by cellulolytic pre-
treatment. Appl. Microbia. Biotech. 29(1):
39-43.
Tokumasu, S., Kanada, I., and Kato, M.
1985. Dormancy and mustard oil (allyl-
isothiocyanate) content in seeds of Brassica
juncea Czern. et Coss. and B. carinata Braun.
J. Japan. Soc. Hart. Sci. 54(1):75-81.
Nutmeg/Mace
Nutmegs and mace are derived from the
fruit of a bushy tree (Myristica fragrans
Houttyn), which is a native of the "Spice
Islands" (Moluccas and Banda Island) but
now naturalized in the West Indies and Sri
Lanka. Papuan nutmegs and mace are also
commercial products, but are obtained from
M. argentea Warb. The nutmegs are much
inferior and less aromatic than either
East or West Indian nutmegs; the mace is
acrid and fatty. Bombay wild nutmeg
(M. malabarica Lan.) is the source of a
grade of mace that is almost tasteless.
The yellowish-green fruit is peach-like,
although the size is very variable. When
ripe, the fruit falls from the tree, splits open
to reveal a shiny brown nut containing
a single seed (the nutmeg of commerce),
tightly surrounded by a mesh of bright
scarlet arilode, which when dried becomes
mace. The female trees bear fruit all the
year round. In most areas, the fruit is
allowed to fall naturally; the nutmegs
with their arilus are gathered by hand

and separated, the soft fibrous pulp being
allowed to rot. A limited amount of the pulp
is used to make a confection, but it is not of
real commercial value. As nutmegs are very
liable to insect damage, they are often
allowed to remain in the shell until required
for shipment, at which time the shell is
cracked and discarded.
Commercial . sources East Indies:
Malaysia (Penang), Indonesia (Sumatra,
Siau, Java, Banda Island, Moluccas,
Celebes), West Indies (Granada, St. Vin-
cent, Trinidad) and Sri Lanka.
Nutmeg
Description Grayish-brown, broadly or
slightly elongated ovoid seeds; 2-3 em long
and 1.5-2cm in diameter. The exterior
surface is longitudinally wrinkled and in
some grades the furrows may appear white
due to a dressing of lime (a practice which is
on the decline). A transverse cut reveals
a characteristic marbled appearance.
Nutmegs are graded on size, designated
as the number per pound weight (e.g.,
60-80's, 90's, llO's and 130's) and on
their freedom from damage (i.e., broken,
wormy, etc.). These latter grades are
usually reserved for volatile oil distillation,
wormy nutmegs being much easier to distill
owing to the absence of fixed oil. Most
of the nutmegs imported for extraction are
undamaged, but are not sorted.
Volatile oil content 7-16 percent.
Fixed oil content About 35 percent.
Sensory character Warmly spicy: West
Indian nutmegs are fresh, light and sweetly
spicy; East Indian nutmegs are heavy and
camphoraceous (Heath 1978).
Mace
Mace is prepared by removing, flattening
and sun drying the two-bladed scarlet arilus.
During the drying period the color changes
to reddish-golden-yellow and the texture
becomes horny and brittle. The ratio of
nutmeg to mace by weight is approximately
25:1.
Natural Flavoring Materials 305
Commercial sources Grenada, Penang
and Banda Island, Sri Lanka.
Description Orange (East Indian) to
pale brownish-yellow (West Indian),
smooth, shiny, flattened, irregular branched
pieces up to 4 em long. The texture is horn-
like and very brittle. Mace is graded accord-
ing to size and color.
Papuan and Bombay mace are reddish-
brown in color and are joined to form a solid
base with short curved branches at the tip
only.
Volatile oil content 7-14 percent.
Fixed oil content About 30 percent.
Sensory character Fresh, light spicy
odor with warm, bitter flavor (Heath 1978).
Oil of Nutmeg
The character of nutmeg oil is determined
by the source of the nutmeg. Two main
types are recognized commercially: East
Indian and West Indian. An intermediate
type produced in Sri Lanka is of increasing
importance.
Commercial Sources The majority of
nutmeg oil is produced in Indonesia (120
tons) and Sri Lanka (30 tons), with a small
amount produced in India (5 tons). Nutmeg
oil is also produced in the United States and
United Kingdom primarily from Indonesian
nutmegs, and Belgium and the Netherlands
from Grenadan nutmegs. Lawrence (1985a)
has estimated worldwide production of
nutmeg at 180 metric tons. The oils are
generally classified as being either East
Indian or West Indian type with the Sri
Lankan oils being intermediate.
TABLE 7-58. Characteristics of oil of nutmeg
East Indian West Indian
Sp. Gr.
(25°/25°C) 0.880-0.910 0.854-0.880
Optical rotation
(20°C) +8° to +30° +25° to +45°
RI (20°C) 1.474 to 1.488 1.469 to 1.476
Solubility
(90% ethanol) 3 vol 4 vol
306 Source Book of Flavors

TABLE 7-59. Chemical composition of nutmeg oils

West Indian East Indian Sri Lankan

(%) (%) (%)

a-Pinene 10.6-12.6 18.0-21.2 13.0

Camphene 0.2 0.2-0.4 0.3
~-Pinene 7.8-12.1 9.3-17.7 9.0
Sabinene 49.6-50.7 15.4-44.1 47.9
Myrcene 2.5-2.8 2.2-2.9 0.7
a-Phellandrene 0.4-0.6 0.4-1.0 3.8
a-Terpinene 0.8-1.9 0.8-2.5 trace
Limonene 3.1-3.3 2.7-3.6 4.1
1,8-Cineole 2.3-2.5 1.5-3.2 3.5
y-Terpinene 1.9-3.1 1.3-6.8
p-Cymene 0.7-3.2 0.3-2.7
Terpinolene 1.2-1.7 0.6-2.6 1.0
trans-Sabinene hydrate 0.3-0.8 0.3-0.6
Copaene 0.3 0.2-0.3
Linalool 0.4-0.9 0.2-0.9
cis-Sabinene hydrate 0.2-0.7 0.2-0.6
cis-p-Menth-2-en-ol 0.1-0.4 0.1-0.5 0.8
Terpinen-4-ol 3.5-6.1 2.0-10.9
cis-Piperitol 0.4-0.5 0.3-0.5 0.5
Safrole 0.1-0.2 0.6-3.2 0.3
Methyl eugenol 0.1-0.2 0.5-1.2
Eugenol 0.2 0.3-0.7 0.2
Elemicin 1.3-1.4 0.3-4.6 1.6
Myristicin 0.5-0.8 3.3-13.5 3.8

Specification in FCC III (1981)
(Myristica oil), BP (1980), NF XV (1980).
A colorless or pale yellow oil having the
characteristics shown in Table 7-58.
Constituents The chemical composition
of nutmeg oils has been the subject of
reviews by Lawrence (1976, 1981, 1985b).
Compositional data are presented from
Baldry et al. (1976) on East and West
Indian oil, and Sarath-Kumara, Jansz and
Dharmadasa (1985) on Sri Lankan oil
(Table 7-59).
Additional work has been done on the
composition of nutmeg oil by the Analytical
Methods Committee of the Analytical
Division of the Royal Institute of Chemistry
(1984), but the reader is encouraged to
consult Lawrence (1985b) for comments on
these data.
Oil of Mace
Obtained by the steam distillation of mace
in the East and West Indies, the character of
the volatile oil depends on the source. The
specification for Mace Oil in EOA No. 182
gives figures similar to those for Nutmeg Oil
EI and WI in FCC II (1972). In the trade,
little difference is made between the two
oils, although mace oil is invariably more
highly priced.
Nutmeg Butter
The mixed fixed and volatile oils of nutmeg
may be recovered by hot pressing to give a
product commercially known as "nutmeg
butter."
The yield is about 25-30 percent, the
product containing trimyristicin (70 per-
cent), volatile oil (13 percent), fats (4
percent), resins (2 percent), together with
other nonsaponifiable components. Salzer
(1975) reports the following ratios:
Nutmeg Butter saturated fats 90 per-
cent; unsaturated fats 10 percent.
Mace Butter Saturated fats 40 percent;
unsaturated fats 60 percent.
 Natural Flavoring Materials 307

TABLE 7-60. Commercially available nutmeg TABLE 7-61. Commercially available mace
oleoresins oleoresins

Volatile Oil Suggested Volatile Oil Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion Content Use Rate in Dispersion
(ml/100 g) (%) (%) (ml/lOOg) (%) (%)

25-30 7.6 1.9-2.3 8-24 10 0.8-2.4

55-60 8-10 4.4-6.0 40-45 6-8 2.4-3.6
80 6 4.8 50 7.5 3.75
80-90 5 4.0-4.5 50-56 7.5 3.75-4.2

Oleoresin Nutmeg Seven Essential Oils. Analyst 109:1343-1360.

Oleoresin nutmeg is obtained by the solvent
extraction of ground East or West Indian
nutmegs, the aromatic character of the pro-
duct being determined by the source. It is a
pale yellow to golden-yellow viscous to fluid
oleoresin, which may be clear and oily or
opaque and waxy, but becoming clear on
warming to 50°C.
The commercially available oleoresins
are shown in Table 7-60.
Oleoresin Mace
Obtained by the solvent extraction of mace.
of either East or West Indian origin.
Specification in EOA No 241.
A clear amber or dark red fluid oleoresin.
The EOA specification requires the
oleoresin to contain 20-50 ml/100 g of
volatile oil having an optical rotation of -2°
to +45° and a refractive index of 1.469 to
1.500.
The commercially available oleoresins
are shown in Table 7-61.
Quality Assessment of Nutmeg and
Mace Oleoresins
The quality assessment of oleoresins of
nutmeg and mace was discussed by Salzer
(1975); the ratio of a-pinene, myristicin and
safrole are recommended as characterizing
attributes.
References: Nutmeg/Mace
Analytical Methods Committee, 1984. Applica-
tion of Gas-Liquid Chromatography to the
analysis of Essential oils. XI. Monographs for
Archer, A.W. 1988. Determination of safrole
and myristicin in nutmeg and mace by high-
performance liquid chromatography. J.
Chrornatog. 438(1):117-121.
Baldry, J., Dougan, J., Matthews, W.S.,
Nabeny, J., Pickering, G.R., and Robinson,
F.V. 1976. Composition of flavor of nutmeg
oils. Int. Flavours Food Additives 7:28-30.
Baldry, J., Dougan, J., Matthews, W.S.,
Nabeny, J., Pickering, G.R., and Robinson,
F.V. 1974. Chemical composition and flavor
of nutmegs of different geographical origins.
4th Int. Congr. Food Sci. Techno[. Proc.
la:38-40.
Damhoeri, A., Hosono, A., Itoh, T., and
Matsuyama A. 1985. In vitro mutagenicity
tests on capsicum pepper, shallot and nutmeg
oleoresins. Agric. Bio. Chern. 49(5):
1519-1520.
Davis, D.V. and Cooks, R.G. 1982. Direct
characterization of nutmeg constituents by
mass spectrometry-mass spectrometry. J.
Agric. Food Chern. 30(3):495-504.
Gecan, J.S., Bandler, R., Glaze, L.E., and
Atkinson, J.C. 1983. Microanalytical quality
of ground and unground oregano, ground
cinnamon and ground nutmeg. J. Food
Protect. 46(5):387-390.
Greene, L.M. 1989. Nutmeg emulsion and
process for making same. United States
Patent. 4:832-974.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn. AVI
Publishing Co.
lmbert, M.P. 1983. The preservative properties
of spice extracts prepared from cinnamon,
clove and nutmeg. Proceedings of the 6th
International Congress of Food Science and
Technology. 1:51-52.
308 Source Book of Flavors
International Organization for Standardiza-
tion 1985. Oils of sassafras and nutmeg-
Determination of safrole and cis- and trans-
isosafrole content-Gas chromatographic
method on packed columns. International
Standard; ISO 7355-1985, 4pp.
Joseph, J. 1980. The nutmeg-its botany,
agronomy, production, composition, and
uses. J. Plant. Crops. 8(2):61-72.
Lawrence, B.M. 1976. Progress in essential oils.
Nutmeg. (A monthly review.) Perf Flav.
1(4):33.
Lawrence, B.M. 1981. Progress in essential oils.
Perf Flav. 6(3):46-49.
Lawrence, B.M. 1985a. A review of the world
production of essential oils. Perf Flav.
10(5): 1-20.
Lawrence, B.M. 1985b. Progress in essential oils.
Perf. Flav. 10(4):45.
Oberdieck, R. 1989. Mace and nutmeg.
Fleischwirtschaft. 69(11):1648-1664, 1707.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Sarath-Kumara, S.J., Jansz, E.R., and
Dharmadasa, H.M. 1985. Some physical and
chemical characteristics of Sri Lankan nutmeg
oil. J. Food Sci. 36:93-100.
Schenk, H.P. and Lamparsky, D. 1981. Analysis
of nutmeg oil using chromatographic
methods. J. Chromatog. 204:391-395.
Sholto-douglas, J. 1971. Nutmeg and mace-
culture and field production. Flavour Ind.
2:573-574.
Smith, A.E. 1986. International trade in cloves,
nutmeg, mace, cinnamon, cassia and their
derivatives. Report, Tropical Development
and Research Institute. G193, ix + 161pp.
ISBN 0-85954-203-3.
Oregano (Mexican Sage)
Several botanicals are classified as
"oregano," the various species differing
significantly in aromatic quality and in
commercial value. The word "oregano"
is Spanish for marjoram and the herb is
sometimes called wild marjoram or pot
marjoram-the designations are so con-
fused that it is extremely difficult to establish
just what botanical entity is involved. The
truer classifications are probably:
Mexican oregano (Mexican sage)-Lippia
species, usually Lippia graveolens HBK.
European oregano (Greek oregano)-
Origanum species, mostly Origanum
vulgare L.
Other genera include Coleus, Lantana
and Hyptio. Some authorities feel that the
designation "oregano" should not be taken
to refer to any one species, but to a par-
ticular spice flavor derived from plants of
several species in different parts of the
world. Oregano is particularly important in
Mexican cuisine and in Italian pizza, the
characteristic flavor of which is now interna-
tionally popular.
Whole Spice
Commercial Sources Greece and Mexi-
co are the major sources but also Japan,
Turkey, Lebanon, Dominican Republic and
Portugal.
Description Mexican sage is the dried,
light green, ovate curled or folded leaves;
6-8 mm long; some with short petioles.
Sensory character Strongly aromatic,
camphoraceous odor; warmly pungent,
bitter herbaceous flavor (Heath 1978).
Oleoresin Oregano (Mexican Sage)
Only one manufacturer offers this particular
oleoresin:
Volatile oil Suggested Volatile oil
content use rate in dispersion
(ml/100 g) (%) (%)
36-44 4 1.44-1.76
References: Oregano (Mexican Sage)
Akguel, A., and Kivanc, M. 1988. Inhibitory
effects of selected Turkish spices and oregano
components on some foodborne fungi. Inte. J.
Food Microbia. 6(3):263-2681.
Benjilali, B., Richard, H.M.J., and Baritaux, 0.
1986. Study of essential oils of two species of

Moroccan oregano Origanum compactum and
Origanum elongatum. Lebens. Wiss. Techno/.
19(1):22-26.
Fernandez, J.E., Krivoruchco, D.D., and
Mitschelo, O.J. 1984. Microbiological study
of species. I. Oregano. Revista Argentina de
Microbiologia. 16(3):111-118.
Fleisher, A. and Sneer, N. 1982. Oregano spices
and Origanumchemotypes. J. Sci. Food
Agric. 33(5):441-446.
Gecan, J.S., Bandler, R., Glaze, L.E., and
Atkinson, J.C. 1983. Microanalytical quality
of ground and unground oregano, ground
cinnamon and ground nutmeg. J. Food
Protect. 46(5):387-390.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn. AVI
Publishing Co.
Kikuzaki, H., and Nakatani, N. 1989. Structure
of a new antioxidative phenolic acid from
oregano (Origanum vulgare L.). Agric. Bio.
Chern. 53(2):519-524.
Lawrence, B.M. 1984. The botanical and
chemical aspects of oregano. Perf. Flavor.
9(5):41-51.
Nakatani, N. and Kikuzaki, H. 1987. A new
antioxidative glucoside isolated from oregano
(Origanum vulgare L.). Agric. Bio. Chern.
51(10):2727-2732.
Rhyu, H.Y. 1979. Gas chromatographic charac-
terization of oregano and other selected spices
of the labiate family. J. Food Sci. 44(5):
1373-1378.
Stahl, W.H. et a!. 1969. Differentiation of
geographic origin of spices. II. Oregano by
gas chromatography. J. Assoc. Off. Anal.
Chern. 52:1184-1189.
Origanum (Wild Marjoram)
The botanical classification of herbs known
as "origanum" is involved and Arctander
(1960) proposed a grouping that is widely
accepted. This includes:
Origanum: Coridothymus capitatus Rchb.
(alternatively classified as Thymus
capitatus Hoffm. and Link.) and other
species of Thymus or Origanum the
volatile oils of which contain 60 to 75 per
cent of total phenols consisting mainly of
noncrystallizable carvacrol.
Natural Flavoring Materials 309
Wild Marjoram: Either Origanum vulgare
L. or Thymus masticina L.
Whole spice
Commercial Sources Lawrence (1978)
lists the following sources of commercial
value:
Greece: from Origanum heracleoticum L.
Italy: from 0. gracile L.
Morocco: from 0. uirens Hoffm. and Link.
Spain: from Coridothymus capitatus Rchb.
Syria: from 0. maru L. (also classified
as Majorana maru (L.) Briq.) or 0.
syriacum.
Wild European: from 0. vulgare ssp.
vulgare L.
Description A mixture of dried, light
green ovate leaves, many curled or folded;
3-4 mm long with small purplish floral
parts.
Volatile oil content Depending on
seasonal conditions, the fresh herb contains
about 0.9 percent of oil (Guenther 1948-
1952).
Sensory character Strongly aromatic,
the aromatic profile depending on the
type (Heath 1978). The flavor is warmly
phenolic, richly herbaceous and somewhat
bitter.
Origanum Oil
Sources The most important sources
for this oil are Albania (3 tons), Spain (3
tons), and Yugoslavia (1 ton). Turkey and
Portugal also produce some oil. The world
production was estimated to be 8 metric
tons in 1984 (Lawrence 1985).
Specification in EOA No. 142. FCC III
(1981).
A yellowish-red to dark brownish-red oil,
which may be rectified to a colorless to pale
yellow oil; specific gravity (25°/25°C), 0.935
to 0.960; optical rotation (20°C), -2° to
+3°; refractive index (20°C), 1.502 to 1.508;
solubility (70 percent ethanol), 2 vol with
310 Source Book of Flavors

some opalescence on dilution; total phenols, TABLE 7-62. Percentages of constituents of oils of
60 to 75 percent by volume. origanum
Constituents The numerous reports on ---------------------------------
Thymol Carvacrol
the chemical composition of origanum oils (%) (%)
from different sources have been reviewed
and the constituents tabulated by Lawrence Greek origanum 5 7.5
Turkish origanum 0.8 83
(1978, 1981). Numerous investigators have
Spanish origanum 18 4.5
studied the composition of marjoram oil Italian 60 9
(Maarse and Van Os, 1973; Masada 1976;
Rhyu 1979; Oberdieck 1981; Brosche 1981;
Lawrence 1981). TABLE 7-63. Commercially available origanum
oleoresins

a-thujene (0.2%) Volatile Oil Suggested Volatile Oil

13-pinene (0.2%) Content Use Rate in Dispersion
myrcene (0.8%) (mlllOOg) (%) (%)
a-terpinene (3.4%) 17-20 13-15 2.2-3
f3-phellandrene (0. 9%) 27-30 8-10 2.2-3
cis-ocimene (0.1%) 42-46 1.5 0.6-0.7
p-cymene (3.2%)
a-p-dimethyl styrene (0.1%)
linalool (1.0%) The ratios shown in Table 7-62 for thymol
linalyl acetate (2.2%) and carvacrol are of value in assessing the
terpinen-4-ol (46.1%) sensory characters of oils of origanum.
caryophyllene (2.6%)
a-humulene (0.2%) Oleoresin Origanum
a-terpinyl acetate (0.2%) There are no specifications for this oleoresin
but the following are available commercially
bicyclogermacrene (1.1%)
p-cymen-8-ol (0.1%) (Table 7-63).
Quality Assessment Salzer (1975) has
elemol (0.2%)
discussed the criteria for assessing the
a-pinene (0.6%)
quality of oleoresins of origanum and thyme
sabinene (2.8%)
and recommends the determination of total
a-phellandrene (0.3%)
phenols and a GLC examination of the
limonene (0.8%)
recovered essential oil.
1,8-cineole (0.1%)
a-terpinene + transocimene (7 .6%)
References: Origanum (Wild Marjoram)
terpinolene (1.1%)
Akguel, A. and Bayrak, A. 1987. Constituents of
trans-sabinene hydrate (0. 7%) essential oils from Origanum species growing
cis-sabinene hydrate (7. 8%) wild in Turkey. Planta Medica. 53(1):114.
cis-p-menth-2-en-1-ol (2.4%) Arctander, S. 1960. Perfume and Flavor Materials
terpinen-4-yl acetate (0.2%) of Natural Origin. Elizabeth, N.J.: Steffen
trans-p-menth-2-en-1-ol (1.6%) Arctander.
a-terpineol (7 .6%) Benjilali, B., Richard, H.M.J., and Baritaux, 0.
neryl acetate (0.4%) 1986. Study of essential oils of two species of
geranyl acetate (0.6%) Moroccan oregano Origanum compactum and
caryophyllene oxide (0.1%) Origanum elongatum. Lebens. Wiss. Techno/.
19(1):22-26.
Brosche, T., Vostrowsky, 0., Gemeinhardt, F.,
Asmus, U., and Knobloch, K. 1981. Uber
die komponenten des atherischen Ols aus

Marjorana hortensis Moench. Z. Naturforsch.
36:23-29.
Carmo, M.M., Frazao, S., and Venancio, F.
1989. The chemical composition of Portuguese
Origanum vulgare oils. J. Essen. Oil Res.
1(2):69-71.
El Keltawi, N.E., Abdou, R.F., and Bishay,
D.W. 1985. Comparative studies on growth
and volatile oil contents of some induced
mutants of Origanum majorana. In Essen-
tial Oils and Aromatic Plants, eds. A.B.
Svendsen and J.J.C. Scheffer, pp. 191-197.
Netherlands: Martinus Nijhoff.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
Harvala, C., Menounos, P., and Argyriadou, N.
1987. Essential oil from Origanum dictamnus.
Planta Medica. 53(1):107-109.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. Westport, Conn. AVI
Publishing Co.
Lawrence, B.M. 1985. A review of the world
production of essential oils (1984). Perf. Flav.
10(5):1-20.
Lawrence, B.M. 1981. unpublished information.
Lawrence, B.M. 1978. Progress in essential oils.
Origanum. (A monthly review.) Perf. Flav.
2(5):48-50.
Maarse, H. and Van Os, F.H.L. 1973. Volatile
oil of Origanum vulgare ssp. vulgare. I.
Qualitative composition of the oil. Flavour
Ind. 4:477-481. II. Oil content and quantita-
tive composition of the oil. Ibid. 4:481-484.
III. Changes in composition during matura-
tion. Ibid. 5:278-281.
Masada, Y. 1976. Analysis of Essential Oils by
Gas Chromatography and Mass Spectrometry.
New York: John Wiley & Sons Inc.
Oberdieck, R. 1981. Ein Beitrag zur kenntnis
und Analytik von Majoran (Marjorana
hortensis Moench.). Deutsch. Lebensmitt-
Rundschau 77:63-74.
Putievsky, E., Ravid, U., and Husain, S.Z. 1985.
Differences in the yield of plant material,
essential oils and their main components dur-
ing the life cycle of Origanum vulgare L.. In
Essential Oils and Aromatic Plants, eds. A.B.
Svendsen and J.J.C. Scheffer, pp. 185-189.
Netherlands: Martinus Nijhoff.
Putievsky, E., Ravid, U., and Dudai, N. 1988.
Phenological and seasonal influences on
essential oil of a cultivated clone of Origanum
vulgare L.. J. Sci. Food Agric. 43(3):225-228.
Natural Flavoring Materials 311
Rhyu, H.Y. 1976. Gas chromatographic charac-
terization of oregano and selected spices
of the labiatae family. J. Food Sci. 44:
1373-1378.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleo resins) and essential
oils from seasonings. I. Int. Flavours Food
Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Sarer, E., Scheffer, J.J.C., Janssen, A.M., and
Baerheim, Svendsen, A. 1985. Composition
of the essential oil of Origanum majorana
grown in different localities in Turkey. In
Essential Oils and Aromatic Plants, eds. A.B.
Svendsen and J.J.C. Scheffer, pp. 209-212.
Netherlands: Martinus Nijhoff.
Sendra, J.M. and Cunat, P. 1980. Volatile
constituents of the Spanish origanum
(Coridothymus capitatus) essential oil.
Phytochem. 19(7):1513-1517.
Vokou, D., Kokkini, S., and Bessiere, J.M.
1988. Origanum onites (Lamiaceae) in
Greece: distribution, volatile oil yield, and
composition. Econ. Botany. 42(3):407-412.
Paprika
Paprika is the ground dried ripe fruits of
Capsicum annuum L., cultivated in Central
and Southern Europe and in North and
South America. The commercial product is
usually a moderately fine powder prepared
in the country of origin. The main varieties
are offered under three categories, namely
sweet, semisweet and pungent. In each
there are several grades and qualities,
depending on the relative proportions of
color-rich pericarp and diluents such as
peduncles, calices, placental tissue and
seeds included in the grinding mix.
Whole Spice
Commercial Sources Hungary, Bulgaria,
Spain, Portugal and the United States, with
limited quantities available from Chile and
Argentina.
Description A bright rich dark red to
brownish-red powder having a pleasantly
agreeable odor and a sweet to mildly
pungent taste, depending on the source and
grade.
312 Source Book of Flavors
Constituents Although paprika has a
definite flavor and a degree of pungency
depending on the grade, it is valued as a
spice primarily for its coloring properties.
The colored constituents are carotenoids
present at about 0.3 to 0.8 percent in the
fruit. They comprise: capsanthin (35-60
percent), capsorubrin (18 percent), a- and
~-carotene (8-23 percent), zeaxanthin
(8-10 percent), cryptoxanthine (3-5 per-
cent) and lutein (8-10 percent) (Benedek
and Mecs 1971).
The chemistry of these components
will be further discussed in the section on
natural coloring materials.
Oleoresin Paprika
Specification in EOA No. 239.
A deep red somewhat viscous liquid
pourable at room temperature. The EOA
specification requires the oleoresin to have
a stated color value between 40,000 and
100,000 units, determined either visually or
instrumentally by the methods described.
Most manufacturers supply oleoresin
paprika with designated color values within
the range 30,000 to 100,000 units; the most
widely used is 40,000 and 80,000CU pro-
ducts. Care must be exercised in assessing
the relative worth of products just on
the quoted numerical color value as the
accepted methods of assessment do differ:
EAO No. 239 absorbance at 458nm arbi-
trary factor 61,000
ASTA Method MSD-10 absorbance at
462 nm arbitrary factor 66,000
Quality Assessment Salzer (1975) has
pointed out that the spectrophotometric
absorption maximum for a solution of
oleoresin paprika in acetone lies between
450 and 475 nm and that the ratio of red:
yellow color components is approximately
85 : 15. The former gives a direct measure of
the total available color (tinctoral power),
whereas the latter is a better indication of
the tint produced in an end product.
References: Paprika
Beatus, Y., Raziel, A., Rosenberg, M., and
Kopelman, I.J. 1985. Spray-drying micro-
encapsulation of paprika oleoresin. Lebens.
Wiss. Techno/. 18(1):28-34. III. Ibid. 6:
253-258.
Benedek, L. and Mecs, J. 1971. The components
of paprika. Konserves Paprikaipar 1:61.
Geister, H. 1989. Paprika oleoresin-pure.
Fleischwirtschaft. 69(9):1380-1382.
International Organization for Standardization.
1989. Ground (powdered) paprika. Deter-
mination of total natural colouring matter
content. International Standard; ISO 7541:
1989, 3pp.
Oberdieck, R. 1988. Paprika. Fleischwirtschaft.
68(9):1086-1096, 1152.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavour Food
Additives 6:151-157. II. Ibid. 6:206-210.
Zilberboim, R., Kopelman, I.J., and Talmon, Y.
1986. Microencapsulation by a dehydrating
liquid: Retention of paprika oleoresin and
aromatic esters. J. Food Sci. 51(5): 1301-1306.
Parsley
Parsley is a biennial Umbelliferous plant
( Petroselinum satiuum Hoffm.) or P. ctispum
(Mill.) Nyman, which is widely cultivated
in most temperature countries. The freshly
cut green leaves are extensively used as a
culinary garnish and as a source of flavor;
the herb is dried and rubbed. The seeds
(fruits) are used as a source of volatile oil.
Commercial Sources
Europe (France, Germany, Hungary),
North Africa (Tunisia, Morocco), North
and South America.
Sensory Character
Parsley herb has an agreeable aromatic,
freshly herbaceous and quite characteristic
odor. The oil distilled from the freshly cut
herb has the same profile, but that from the
seeds is much less pleasant, having a harsh
terpeny character.
Parsley Herb
Description Green curled whole and/or
 Natural Flavoring Materials 313

broken segmented leaves, some with short P-Bisabolene (0.5%)

stalks. o-cadinol (0.6%)
Volatile Oil Content The fresh herb myristicin (20.6%)
contains less than 0.1 percent of volatile oil, *tentative identification
but up to 0.25 percent if the herb is allowed methylhexadiene* (0.3%)
to mature until the seeds are set but not a-pinene (5.1%)
ripe. toluene (trace)
Oil of Parsley Herb Obtained by hexanal (0.1%)
the steam distillation of the fully mature sabinene (0.3%)
herb, including the immature seeds. Less myrcene (4.3%)
then 2 metric tons were estimated to have a-terpinene (trace)
been produced in Hungary, the United P-phellandrene (12.4%)
States, South Africa, Egypt and the United cis-P-ocimene (trace)
Kingdom in 1984 (Lawrence 1985). trans-P-ocimene (0.1%)
Specification in EOA No. 293, FCC III terpinolene (2.1%)
(1981). cis-3-hexenol (0.1%)
A yellow to light brown oil; specific a-cubebene (0.2%)
gravity (25°/25°C), 0.908 to 0.940; optical copaene (trace)
rotation (20°C), + 1o to -9°; refractive caryophyllene (0.4%)
index, 1.503 to 1.530; acid value, max 2. y-elemene (0.1%)
Constituents Lawrence (1986) has cryptone (0.1%)
reviewed the research related to the com- y-cadinene (0.5%)
position of parsley leaf oil. Composition a-elemene (1.0%)
has been studied by Kasting et al. (1972), 2-p-tolylpropan-2-ol (0. 7%)
Vernon and Richard (1983) and MacLeod elemicin (0.3%)
et al. (1985). The results of MacLeod et al. apiole (18.3%)
(1985) are presented below:
MacLeod et al. (1985) noted that B-
methyl alcohol + phellandrene, terpinolene, a-p-dimethyl
dimethylsulphide (0.1%) styrene, p-mentha-1 ,3,8-triene, myristicin
a-thujene (0.1%) and apiole have aromas characteristic of
camphene (0.2%) parsley leaf.
P-pinene (1.8%)
o-3-carene +xylene* (0.2%) Parsley Seed
a-phellandrene (0. 7%) Description Minute joined or separated
limonene (3.6%) mericarps, light brown in color; 2-4 mm
2-pentylfuran (0.1%) long and about 1 mm wide; pale ridges are
y-terpinene (0.4%) visible under magnification.
p-cymene (1.4%) Volatile Oil Content 2-7 percent.
p-mentha-1, 8-triene (9 .2%)
a-p-dimenthylstyrene (7 .2%) Oil of Parsley Seed
benzaldeyde (trace) Obtained by the steam distillation of the
P-elemene (0.1%) ripe fruits. Approximately 5 metric tons
phenylacetaldehyde (0.1%) were produced in the United Kingdom,
a-terpineol (1. 7%) Egypt, Poland, the Netherlands, France and
dimethylbenzofuran * (trace) India in 1984 (Lawrence 1985).
2-(p-tolyl) propanal (0.3%) Specification in EOA No. 139, FCC III
p-methylacetopheneone + (1981).
P-sesquiphellandrene (trace) A yellow to light-brown oil; specific
314 Source Book of Flavors

gravity (25°/25°C), 1.040 to 1.080; optical trans-~-ocimene (0.02)

rotation (20°C), -4° to -10°; refractive u-p-dimethyl styrene (0.18)
index (20°C), 1.513 to 1.522; acid value, 1,3,8-p-menthathriene (0.03)
max 4; saponification value, 2 to 10; solu- p-menthatrieneol isomer (1.34)
bility (80 percent ethanol), 6 vol possibly p-menthatriene isomer (1.50)
with opalescence. p-menthatrienol isomer(-)
Constituents Parsley seed oil com- a-terpineol (0.12)
position has been reviewed by Lawrence trans-dihydrocarveol (-)
(1981/82). Formacek and Kubeczka (1982) a-terpinyl acetate (0.03)
and more recently, Shaath et al. (1988) have ~-bourbonene (-)
reported on the composition of parsley seed ~-elemene (-)
oil. The results of Shaath et al. (1986) on the trans-~-farnesene (0.10)
composition of Egyptian parsley seed oil are germacrene D (-)
presented below: a-selinene (trace)
sesquiphellandrene (-)
a-thujene (0.19) unknown sesquoterpene alcolol (-)
camphene (0.11) 1,2,3,6-tetra methylcaratol (0.14)
~-pinene (10.78)
8-3-carene (-) n-butyl phthalide (-)
a-terpinene (0.03) sedanenolide (0.12)
limonene (6.57) benzyl benzoate (-)
cis-~-ocimene (0.02) various fatty acid esters
y-terpinene (0.44)
terpinolene (0.05) Oleoresin Parsley
phenylentane (-) Normally prepared from parsley seed, the
cryptone (-) prime oleoresin is blended with parsley herb
borneol (0.16) oil to give the characteristic profile of the
terpinen-4-ol (0.07) fresh herb.
cis-dihydrocarveol (-) The commercially available oleoresins
carvone (0.03) are shown in Table 7-64.
a-copaene (-)
bornyl acetate(-) References: Parsley
~-caryophyllene (0.09) Ashraf, M., Ahmad, R., Mahmood, S., and
ar-curcumene (0.02) Bhatty, M.K. 1980. Studies on the essential
~-selinene (-) oils of the Pakistani species of the family
myristicin (13.27) Umbelliferae. XL VIII. Petroselium crispum
elemicin (4.61) (Miller), Hills (Eng. parsley) oil of the green
caryophyllene oxide (0.05) plant. Pakistan f. Sci. Ind. Res. 23(3/4):128-
allylbenzene (0.68) 129.
dellapiole (-) TABLE 7-64. Commercially available parsley
apiole (36.30) oleo resins
sedanolide (2.84)
Volatile Oil Suggested Volatile Oil
unknown diterpene Content Use Rate in Dispersion
~-pinene (16.48) (ml/100 g) (%) (%)
sabinene (0.31)
myrcene (0.73) Seed
6-14 10 0.6-1.4
a-phellandrene (0.02) Blended
p-cymene (0.55) 12-15 3 0.36-0.45
~-phellandrene (0.65)

Formacek, K. and Kubeczka, K.H. 1982.
Essential oils analysis by capillary chromato-
graphy and carbon-13 NMR Spectroscopy.
New York: John Wiley & Sons.
Golubev, V.N., Bondar', S.N., and Kalandadze,
V.V. 1987. Distribution of S-methylmeth-
ionine in parsley and celeriac. Izvestiya
Vysshikh Uchebnykh Zavedenii, Pishchevaya
Tekhnologiya. No. 3:95-96.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
Kasting, R., Andersson, J., and Sydow, E.
von 1972. Volatile constituents in leaves of
parsley. Phytochem. 11(7):2277-2282.
Lawrence, B.M. 1981. Parsley oils: Leaf, Seed
and Herb in Progress in Essential Oils. Perf.
Flav. 6(6):46-48.
Lawrence, B.M. 198111982. Progress in essential
oils. Perf Flav. 6(6):43.
Lawrence, B.M. 1986. Progress in essential oils.
Perf. Flav. 11(2):75.
Lawrence, B.M. 1976. Progress in essential oils.
Parsley Leaf. (A monthly review). Perf. Flav.
1(1):3.
MaLeod, A.J., Snyder, C.H., and Subramanian,
G. 1985. Volatile aroma constituents of
parsley leaves. Phytochem. 24(11):2623-
2627.
Nitz-S, Kollmannsberger-H, Spraui-MH, and
Drawert-F. 1989. Oxygenated derivatives of
menthatriene in parsley leaves. Phytochem.
28(11):3051-3054.
Philippon, J., Rouet, Mayer M.A., Fontenay,
P., and Duminil, J.M. 1986. Storage time
and temperature in relation to stability of
chlorophylls, colour, and total release of
volatiles in frozen parsley. Sci. des Aliments.
6(3):433-446.
Shaath, N.A., Griffin, P., Dedeian, S., and
Paloympis, L. 1988. The chemical com-
position of Egyptian parsley seed, absolute
and herb oil. In Flavors and Fragrances: a
World Perspective Proceedings of the lOth
International Congress of Essential Oils, eds.,
B.M. Lawrence, B.D. Mookherjee and B.J.
Willis, pp. 715-729. New York: Elsevier.
Simon, J.E. and Quinn, J. 1988. Characteriza-
tion of essential oil of parsley. J. Agric. Food
Chern. 36(3):467-472.
Vernon, F. and Richard, H.M.J. 1983. Volatile
constituents of essential oil of curly parsley
(Petroselinum hortense, Hoff.). Leben.
Wissen. Techno[. 16(1):32-35.
Natural Flavoring Materials 315
Pepper (Black and White)
Black and white pepper of commerce
consists of the dried unripe berries of Piper
nigrum L., a vine-like plant that originated
in the western Ghats of India, but now has
spread to many tropical regions having the
correct environment. For the preparation of
black pepper, the berries are harvested
while they are still immature and green,
then the whole berries are sun-dried, during
which they change color to almost black and
the pericarp becomes deeply wrinkled.
White pepper is prepared from berries that
are somewhat riper, gathered as their color
is changing to yellow but before they
become red; the berries are water-soaked in
hessian sacks to loosen the soft pericarp,
which is then removed by friction. The
washed kernels are sun-dried. A white
pepper may also be prepared from whole
black pepper by mechanically removing the
brown outer hulls (decortication).
There are other spices known as
"pepper," most prominent among which
are:
Red pepper Capsicum annuum L.,
(Capsicums) and other species
Jamaica pepper Pimenta dioicil (L.)
(Allspice or Pimento) Merrill.
Japanese pepper Zanthoxyum piperatum
Melegueta pepper DC.
(Grains of Paradise) Amonum melegueta V.
Californian pepper Schinus molle L.
Commercial Sources India, Malaysia,
Singapore, Indonesia, Cambodia, Vietnam,
Sri Lanka, Brazil and West Africa. The
commercial varieties are listed in Table
7-65. These do not represent discretely
different products, but rather are com-
mercial "types" obtained by blending
innumerable batches of pepper either grown
in the country of origin or imported from
neighboring sources. There is a considerable
entrepot trade in pepper.
Sensory Character Pepper has a two-
fold use in seasonings; it imparts a mildly
 316 Source Book of Flavors

TABLE 7-65. Commercial varieties of black and white pepper

Vola tile Oil Piperine
Content Content
Commercial Country of Exported %v/w (UV)
Designation Origin Growing Region from low avg high %w/w
Black pepper
Malabar India Malabar coast (Karnataka Bombay 1.5 4.0 5.0 1.9-6.0
Mangalore and Kerala), Mysore,
Tellicherry Travancore and Western
Aleppey Madras
Lam pong Indonesia Lam pong, Sumatra Padang 1.5 3.3 4.0 3.0-5.5
Singapore Singapore Singapore, Malaysia, Singapore 2.0 3.0 4.0 3.0-5.5
Cambodia; there is
considerable entrep6t
trade with Sarawak
Vietnam Saigon
Saigon
Sarawak Sarawak Kuchingand 2.3 3.5 4.0 5.0-6.0
via Singapore
Siam Siam Southeast Siam Bangkok and
via Singapore
Ceylon Sri Lanka Colombo 2.0 2.8 3.5 4.5-5.5
Malagasy Malagasy Tamatave
Republic
Brazil Brazil
White Pepper
Muntok Indonesia Banka, Korintiji 4.5-5.0
Sarawak Sarawak Belantong, Kuching Kuchingand 5.0-6.0
Djambi via Singapore
Brazil Brazil

aromatic and characteristic flavor and also a White Pepper

distinctive "bite" or pungency, different
from that produced by capsicum. It is the
volatile oil content that contributes the
aroma and the nonvolatile constituents,
mostly piperine, which are the source of
the pungency. The unique value of pepper
lies in the combined effects of these two
attributes. It is the balance between them
that distinguishes peppers from different
sources, and of different grades or qualities.
Indian peppers are generally very aromatic,
whereas those from Malaysia and Indonesia
are less aromatic but distinctly more pun-
gent. Brazilian pepper, most of which is
imported into the United States, is not
unlike the best grades from Singapore,
having a well-balanced odor and flavor
profile.
Volatile Oil Content See Table 7-65.
Fixed Oil Content 2-9 percent, the
composition of which has been investigated
by Salzer (1975).
Description Light yellowish-gray globu-
lar kernels of pepper berries; 3.5 to 6 mm in
diameter; surface is smooth and may be
more or less obviously striated; flattened at
one end with a small indentation and having
a protruberance at the opposite end. Each
peppercorn contains a single seed, the
internal appearance being white and mealy.
Black Pepper
Description Dark brown to almost
black globular berries; 3.5-6 mm in di-
ameter; the surface is deeply wrinkled in a
characteristic network; the remains of the
stigma are visible as a short point. Each
peppercorn contains a single seed, the
internal appearance being white and mealy.
Oil of Black Pepper
Sources Lawrence (1985a) estimated
world production of black and white pepper
 Natural Flavoring Materials 317

oil at about 8 metric tons in 1984. The TABLE 7-66. Constituents of pepper
primary sources of this oil were India
Volatile Oil Piperine
(5 tons) and Sri Lanka (1.5 tons). Small (% v/w) (% w/w)
amounts were produced in the United
Kingdom and France from imported spice. Brazilian 29-33 35-46
Specification in EOA No. 102, FCC III Lam pong 29-34 43-48
Malabar 32-44 42-53
(1981). Sarawak 31-37 43-47
A colorless to slight greenish-colored oil;
specific gravity (25°/25°C), 0.864 to 0.884;
optical rotation (20°C), -1 o to - 23°; re-
fractive index (20°C), 1.4795 to 1.4880; ~-bisabolene (2.0%)
solubility, (95 percent ethanol) 3 vol. o-cadinene (0.5%)
Constituents The chemical composition cis-y-bisabolene (0. 7%)
of black pepper oil has been the subject of ar. curcumene (0.6%)
much research over many years. The most piperitone (0.8%)
important aspects have been reviewed cubebol (0.1%)
by Lawrence (1976, 1981, 1985b). The elemol (0.6%)
chemical composition of black pepper oil of y-eudesmol (0.1%)
Indian origin as reported by Lawrence a-bisabolol (0.1%)
(1981) is presented below.
A number of other compounds were also
a-pinene (9.0%) identified as trace components. They are:
a-thujene (1.8%)
camphene (0.1%) a-cubebene
~-pinene (10.4%) o-elemene
sabinene (19.4%) cis-~-bergamontene
o-3-carene (5.4%) trans-~-bergamontene
myrcene (2.2%) ledene
a-phellandrene (1. 7%) a-muurolene
a-terpinene (0.3%) zingiberene
limonene (17.5%) nero I
~-phellandrene + geraniol
1,8-cineole (4.0%) myrtenol
y-terpinene (0.5%) borneol
trans-sabinene hydrate (0.2%) trans-carveol
citronella! (0.1%) trans-pinocarveol
linalool (0.5%) methyl citronellate
terpinen-4-ol (1.0%) a-selinene
a-terpineol (0.2%) calamenene
phellandral (0.2%) mathyl geranate
p-cymene (1.3%) a-terpinyl acetate
terpinolene (0.3%) terpinen-4-yl acetate
copaene (0.5%) camphor
cis-a-bergamotene (0. 7%) pinocamphone
a-bisabolene (0.6%) isopinocamphone
trans-a-bergamotene (0.2%) cis-dihydrocarvone
caryophyllene (14. 7%) carvotanacetone
humulene (0.5%) ~-cube bene
trans-~-farnesene (0.7%) ~-elemene
318 Source Book of Flavors

a-humulene Oleoresin Black Pepper

~-selinene Obtained by the solvent extraction of
sesquisabinene crushed black pepper, the nature of the
cis-sabinene hydrate oleoresin is determined by the raw material
trans-p-menth-2-en-1-ol selected and the solvent used. The oleoresin
myrtenal contains both the volatile oil and nonvolatile
benzaldehyde pungent components together with a vari-
trans-anethole able amount of fixed oil, resins, coloring
methyl carvacrol matter and possibly some sugars, etc. The
2-undecanone average yield of oleoresin lies between 10
pinol and 15 percent.
methylheptenone Specification in EOA No. 240.
dehydro-1, 8-cineole This ranges from a dark green, olive
terpinolene epoxide green or olive drab viscous fluid to cheese-
carvone like oleoresin, the physical character de-
trans-limonene epoxide pending on the ratio of volatile oil to
caryophyllene oxide crystalline piperine. The piperine in fluid
cis-nerolidol oleoresins usually crystallizes on standing to
cubenol give a coarse grainy deposit and an upper
epi-cubenol clear green oily layer. Such oleo resins must
viridiflorol be gently warmed and thoroughly remixed
~-bisabolol to ensure uniformity before use. A homo-
T-muurolol genous oleoresin may be prepared by the
addition of permitted diluents, such as
Jansz et al. (1984) have reported on the propylene glycol or a fatty oil followed by
composition of a standard Sri Lankan cul- mechanical homogenization. This process
tivar of black pepper and the Analytical gives the so-called "pourable" oleoresins.
Methods Committee (1984) of the Royal Composition Pintauro (1971) quotes
Institute of Chemistry has studied the the following ranges for volatile oil and
composition of black pepper oil of Sarawak piperine content of oleoresins prepared
origin. from pepper from different sources (Table
7-66).

TABLE 7-67. Piperine content

uv Kjeldahl Suggested Content

Volatile Oil Method Method Use Rate
(ml/100 g) (%) (%) (%)

Fluid oleoresins
18-20 35-40 50-55 4-7
min 20 min 55 4.5
20-22 min 48
20-33 (not specified) 4.7
23-30 53-57 4.56
Solid oleoresins
18-20 50-55 55-60 7
Pourable oleoresins
9-11 18-20 22-25 5-6.6
12-15 26-29 8-9
15-17 min 50

The EOA specification requires the
oleoresin to contain 15 to 35 ml per 100 g of
volatile oil having and optical rotation of
-1 o to -23° and a refractive index of 1.479
to 1.489. The piperine content shall be not
less than 55 percent by the Kjeldahl total
nitrogen method.
The commercially available oleoresins
are shown in Table 7-67.
Quality Assessment The flavoring qual-
ity of oleoresins of black pepper is judged
on both the essential oil and pungency; the
color is of little consequence, owing to the
very small use rate although some manu-
facturers offer an oleoresin from which
some of the natural chlorophylls have
been removed (so-called "decolorized"
oleoresin).
Volatile Oil Content The quantitative
determination of the volatile oil content is
a prime measure of its flavoring power
and the quality can be judged by sensory
assessment and GC examination of the
recovered oil. The ratio of delta-3-carene +
~-pinene + sabinene: caryophyllene is used
by Salzer (1975) as an indicator of the
source of the pepper; the physical characters
of the oil quoted in the EOA specification
give a good indication of the presence of any
additives.
Pungency Whereas there are few
problems in specifying the volatile oil
content, that of piperine as a measure of the
available pungency is open to considerable
misunderstanding due to the different
methods of analysis employed and the signi-
ficantly different results obtained.
Piperine may be determined by one of
the following methods: (a) As total nitrogen
(Kjeldahl) as described in AOAC method
2.23 or ASTA method No. 12.0 using the
formula to convert to piperine:
(ml N/10 HCL consumed)
% piperine = 2.851 weight of sample (g)
(b) Calorimetrically by the method of the
ASTA No. 13.0 using a chromotropic acid/
sulfuric acid reaction. (c) By alkaline
Natural Flavoring Materials 319
hydrolysis followed by distillation of the
piperidine and its quantification by acidi-
metric titration, as proposed by Labruyere
(1966). (d) Spectrophotometrically as
described in EOA No. 240, based on the
absorbance of piperine in an ethylene di-
chloride solution at 341-342nm, or in
ethanolic solution at 343 nm.
In all cases, the results are quoted in
terms of piperine although this is only one of
the pungent components, albeit 98 percent.
Pruthi (1970) critically examined the various
methods and Salzer (1975) established the
relative reproducibility of the several
methods and strongly recommended the
use of (c), while admitting that (d) was
both simple and speedy in use. In pur-
chasing oleoresins of black pepper for which
piperine contents are quoted, it is desirable
to establish what method of analysis was
used or the figures may be misleading.
The Pungency of Pepper
The principal pungent component of black
pepper has long been established as the
alkaloid piperine, although more recent
investigations have shown that several other
related alkaloids may also contribute to
varying extents. The chemistry of these
pungent components has been extensively
reviewed by Govindarajan (1977, 1986). It
has been established that the isomers of
piperine have almost no pungency and that
the slow. photoisomerization observed in
solutions of piperine explain the observed
reduction in the pungency of pepper pro-
ducts under certain conditions. It is sug-
gested that old samples of pepper may
contain relatively large amounts of the
almost nonpungent isomer isochavicine,
which is determined as "piperine" by the
normal methods of analysis. The various
isomers of piperine are:
0
/O~CH==CH-cH=CH-!-Q
H,c, 0 ~
320 Source Book of Flavors
Relative pungency
Piperine trans-trans 5 1989. Pepper (Piper nigrum Linnaeus), whole
Isopiperine cis-trans
Ioschavicine trans-cis 1 pepper. International Standard. ISO 959-2:
Chavicine cis-cis 2
The minor alkaloids present in pepper
include: piperitine, piperanine, piperylin,
piperolein A and piperolein B (Salzer
1975). In terms of Scoville units, the
following relationships are of interest
(Govindarajan 1977) (Table 7-68).
TABLE 7-68. Pungent compounds in various spices
Pungent Scoville
Compound Present in Units
Capsaicin Capsicums 30 million
Piperine Pepper 200,000
Shogaol Ginger 160,000
Paradol Melegueta pepper 100,000
Gingerol Ginger 80,000
References: Pepper (Black and White)
Analytical Methods Committee. 1984. Applica-
tion of gas-liquid chromatography to the
analysis of essential oils. Part XI. Monographs
for seven essential oils. Analyst 109:1343-
136.
Debrauwere, J. and Verzele, M. 1976a. Con-
stituents of pepper. IV. The hydrocarbons of
pepper oil. J. Chromatogr. Sci. 14:296-298.
Debrauwere, J. and Verzele, M. 1976b. New
constituents of the oxygenated fraction of
pepper essential oil. J. Sci. Food Agric.
26:1887-1894.
Gecan, J.S., Bandler, R., Glaze, L.E., and
Atkinson, J.C. 1986. Microanalytical quality
of ground and unground marjoram, sage and
thyme, ground allspice, black pepper and
paprika. J. Food Protect. 49(3):216-221.
Geeta, H. and Kulkarni, P.R. 1987. Survey of
the microbiological quality of whole, black
pepper and tumeric powder sold in retail
shops in Bombay. J. Food Protect. 50(5):401-
403.
Govindarajan, V.S. 1977. Pepper: Chemistry,
technology and quality evaluation. C.R. C.
Crit. Rev. Food Sci. Nutr. 9(2):115-225.
Govindrajan, V.S. 1986. Capsicum-produc-
tion, technology, chemistry and quality. III.
Chemistry of the color, aroma and pungency
stimuli. Crit. Rev. Food Sci. Nutr. 24:245.
International Organization for Standardization
or ground. Specification. Part 2. White
1989, 8pp.
Jansz, E.R., Balachandran, S., Packiyasothy,
E. V., and Ratnayake, S. 1984. Effect of
maturity on some chemical constituents of Sri
Lankan pepper (Piper nigrum 1. ). J. Sci. Food
Agric. 35:41-46.
Lavruyere, B. 1966. Determination of pungent
constituents of Piper nigrum, L. J. Agric.
Food Chern. 14:469-472.
Lawrence, B.M. 1981. Major Tropical Spices-
Pepper (Piper nigrum L.). In Essential Oils
I979-I980. Wheaton: Allured Publishing
Corp.
Lawrence, B.M. 1976. Progress in essential oils.
Pepper (A monthly review). Perf. Flav.
1(5):13-14.
Lawrence, B.M. 1985a. A review of the world
production of essential oils. Perf. Flav.
10(5):1-20.
Lawrence, B.M. 1985b. Progress in essential oils.
Perfum. Flav. 10(2):51-57.
Mathai, C.K. 1988. A modified extraction and
estimation method [for determination] of
oleoresin and piperine in black pepper (Piper
nigrum L.) berries. Indian Spices. 25(2/3):3-
5.
Patil, R.T. 1989. Drying studies on black pepper
(Piper nigrum L.). J. Food Sci. Techno!.,
India. 26(4):230-231.
Pintauro, N. 1971. Oleoresin pepper. In Flavor
Technology. Park Ridge: Noyes Data Corp.
Pruthi, J.S. 1970. Analytical techniques for the
determination of piperine/pungent principles
in black and white pepper-a critical ap-
praisal. Indian Oil Soap J. 36:167-177.
Rathnawathie, M. and Buckle, K.A. 1984. Effect
of berry maturation on some chemical con-
stituents of black, green and white pepper
(Piper nigrum L.) from three cultivars.
J. Food Techno!. 19(3):361-367.
Sajid, H., Nageswara, S.P., and Swamy,
G.Y.S.K. 1988. Monitoring ethylene di-
bromide residue in Indian black pepper by gas
liquid chromatography using electron cap-
ture detector. Indian J. Techno!. 26(8):403-
404.
Salzer, U-J. 1975. Analytical evaluation of
seasoning extracts (oleoresins) and essential
oils from seasonings. I. Int. Flavours Food

Additives 6:151-157. II. Ibid. 6:206-210. III.
Ibid. 6:253-258.
Vidal, J.P. and Richard, H. 1987. Preparation of
a black pepper oleoresin by extraction with
supercritical C0 2 or a C0 2 /ethanol blend. Sci.
Aliments. 7(3):481-498.
Weaver, K.M., Luker, R.G., and Neale, M.E.
1984. Rapid quality control procedure for the
determination of Scoville heat units and the
detection of chillies in black pepper, via
high-performance liquid chromatography.
J. Chromatog. 301(1):288-291.
Weaver, K.M., Neale, M.E., and Laneville, A.
1988. Liquid chromatographic method for
determination of piperine in Piper Nigrum
(black and white pepper). J. Assoc. Offic.
Analytical Chern. 71(1):53-55.
Peppermint
True peppermint consists of the aerial parts
of the perennial herb Mentha piperita L.,
usually harvested when in flower. Most of
the crop is cultivated for distillation of the
essential oil with only a very small propor-
tion being dried for culinary use. Two
varieties are extensively cultivated, i.e.,
black mint and white mint. The former is
preferred as it gives a better yield of oil, but
there are now so many regional varieties
and cultivars that these original classifica-
tions mean very little. The cultivation and
distillation of peppermint in the United
States, which is the major source, has been
described by Quarre (1975) and Green
(1975). The dried broken herb is used in
Germany and other parts of Europe for
making mint tea; it should not be confused
with culinary mint for making of mint sauce.
Peppermint is one of the world's most
popular flavors, being used in a wide range
of sugar confectionery, chewing gum and
chocolate fillings as well as in pharmaceu-
ticals and liqueurs (e.g., creme de menthe).
For these purposes, the volatile oil is used in
one of the following forms: (a) Natural-
the prime distillation of the leaves and
flowering tops of the freshly harvested herb;
(b) Rectified (or double distilled)-a
redistillation of the prime oil in which the
last 2-5 percent of the still residue is
Natural Flavoring Materials 321
rejected; or (c) Double rectified (or triple
distilled)-a rectification in which the first
fractions of distillate up to whatever per-
centage is deemed necessary, but usually
5-10 percent, are rejected as well as the last
2-4 percent of still residue.
For most purposes, the single rectified oil
is used. The triple distilled oil is preferred
for use in liqueurs, where solubility is an
important attribute, and in cream fillings,
where a good clean peppermint flavor
coupled with long shelf life is necessary.
Sensory Character The odor and flavor
profiles of the various grades of peppermint
oil have been determined by Heath (1978).
Oils of Peppermint
Commercial Sources United States-
90 percent of that produced (Midwest,
Oregon, Yakima, Wash.), the former Soviet
Union, France, Yugoslavia, Hungary, Italy,
Bulgaria and South Africa. Annual produc-
tion was estimated at 2,000 metric tons in
1984 (Lawrence 1985).
Specifications The following speci-
fications are widely applied:
Oil of Peppermint, Natural-EGA No. 1
Oil of Peppermint (rectified)-FCC III
(1981), BP (1980), USP XX (1980).
Oil of Peppermint (triple distilled)-usually
complies with the above specifications
with the exception of the menthol con-
tent, which may be up to 10 percent
higher.
A colorless to pale yellow oil having the
following physicochemical characteristics:
EOA No. 1: specific gravity (25°/25°C),
0.896 to 0.908; optical rotation (20°C), -18°
to -32°; refractive index (20°C), 1.459 to
1.465; total alcohols (as menthol), min 50
percent; total esters (as menthyl acetate),
min 5 percent; solubility (70 percent
ethanol), 3 vol. BP 1980: weight per ml
(20°C), 0.897 to 0.910 g; optical rotation
(20°C), -16° to - 30°; refractive index
(20°C), 1.460 to 1.470; free menthol, min
45 percent; total esters (as menthyl acetate,
322 Source Book of Flavors

TABLE 7-69. Constituents of peppermint oils

Compound Kennewick Michigan Bulgaria

a-pinene 1.64 1.34 1.13

camphene 0.02 0.01
~-pinene 1.97 1.65 1.40
sabinene 0.93 0.77 0.61
myrcene 0.41 0.33 0.41
a-terpinene 0.46 0.43 0.06
limonene 2.61 2.44 2.19
1,8-cineole + ~-phellandrene 7.75 7.02 4.97
cis-~-ocimene 0.51 0.41 0.37
y-terpinene 0.68 0.68 0.11
trans-~-ocimene 0.13 0.11 O.Q7
p-cymene 0.11 0.24 0.08
terpinolene 0.18 0.18 0.04
3-octanol 0.33 0.30 0.50
trans-sabinene hydrate 1.01 1.14 0.15
menthone 17.27 23.14 31.64
menthofuran 7.37 2.48 2.68
isomenthone 2.53 3.08 6.86
linalool 0.30 0.31 0.36
menthyl acetate 3.80 3.69 6.66
neomenthol 3.10 3.25 2.57
caryophyllene 0.14 2.24 1.26
iso-isopulegol (t) 0.79 0.78 0.61
menthol 38.24 38.01 26.78
pulegone 1.63 1.38 3.78
a-terpineol 0.14 0.15
germacrene D 1.33 1.27 0.84
piperitone 0.35 0.46 1.04
viridiftorol 0.13 0.15 0.07

4.0 to 9.0 percent; solubility (70 percent Oil of Cornmint (Mint)

ethanol), 4 vol.
Constituents The chemical composition
of peppermint oils has been reviewed by
Lawrence (1984, 1986). The composition of
two North American oils and one European
oil are presented in Table 7-69 (Formacek
and Kubeczka 1982):
The composition of stored peppermint
(3 yrs. old) shows major changes in men-
thone (16-36 percent) and menthol (46.2-
30.8 percent) as well as lesser changes in
pulegone (0.1-0.7 percent), piperitone
(0.8-1.6 percent), isomenthone (2.5-5.5
percent), and 1,8-cineole (MacLeod 1968).
The differences in peppermint oils and the
reasons for these differences are discussed
in detail by Murray et al. (1988).
Oil of cornmint is obtained from Mentha
arvensis L. var piperescens, and known
officially in the United States as "mint oil,"
"corn oil" or "field mint oil" and must be so
designated when used in any food products.
In commerce, it is widely known as pepper-
mint oil, and is distinguished by its source
(e.g., Brazilian Peppermint Oil). Corn mint
grows wild in China and parts of Japan,
but is now widely cultivated in both these
countries as well as in Taiwan (Formosa),
Brazil, Argentina, India and South Africa.
When freshly cut, the distilled oil contains
60-80 percent of menthol and is usually
solid at room temperature. This prime oil is
immediately "dementholized" by freezing
to recover about 40 percent of the available
 Natural Flavoring Materials 323

1-menthol, which is then purified for sale as TABLE 7-70. Constituents of cornmint oil
such. The residual oil still contains 45-55
Chinese Japanese Brazilian
percent of total alcohols (as menthol). The
ester content of this oil differs significantly a-Pinene 4.30 2.04 3.19
with source; Japanese mint oil contains Camphene 0.80 0.03 0.06
10-12 percent, Chinese about 2 percent ~-Pinene 4.46 1.96 2.73
sabinene 1.61 0.75 1.06
but up to 10 percent, and Brazilian 5-20 myrcene 2.10 0.85 1.43
percent of menthyl acetate. Limonene 5.75 7.14 9.58
1,8-Cineole 1.11 0.24 0.28
Blended Peppermint Oils cis-Ocimene 0.04 0.14 0.22
Blended oils, to satisfy particular flavoring y-Terpinene 0.04
trans-Ocimene 0.07 0.10 0.26
needs, are offered commercially. These oils P-Cymene 0.07 0.07
may be designated with a supplier's code Terpinolene 0.07
number. In view of the considerable cost 3-0ctanol 2.42 0.73 0.38
differential between genuine piperita pep- Menthone 16.31 26.43 31.12
permint and arvensis mint oils, the price Isomenthone 12.10 7.26 6.81
Linalool 0.16 0.41 0.08
bracket is often a very good indication of the Menthyl acetate 1.80 3.38 3.04
relative proportions of these oils present. Neoisopulegol 1.42 0.85 0.98
Where arvensis oil is used in a blend the title Neomenthol 4.08 3.26 2.51
should indicate this, often by the use of Caryophyllene 0.59 1.25 1.25
WONF (With Other Natural Flavors). Isopulegol 1.17 0.38 0.47
Iso(iso )pulegol 0.80 0.25 0.16
Constituents of Cornmint Oil The com- Menthol 33.66 34.68 28.77
position of cornmint oil has been reviewed Pule gone 0.41 1.31 0.63
by Lawrence (1983). He has summarized a-Terpineol 0.32 0.27
much of the research on cornmint oils and Germacrene D 0.46 0.41 0.75
made some observations about new hybrids Pi peri tone 0.58 3.82 2.43
being developed. The newer hybrids were
developed as a better source of menthol. A
result of the hybridization is that cornmint Emberger, R. and Hopp, R. 1987. Synthesis
oils are available with trans-sabinene and sensory characterization of menthol
hydrate, menthofuran and viridiftorol, enantiomers and their derivatives for use in
nature identical peppermint oils. Speciality
which typically are absent from cornmint
Chemicals. 7(3):193-201.
and have been used as indicators of corn-
Formacek, K. and Kubeczka, K.H. 1982.
mint oil being used to adulterate peppermint Essential oils analysis by capillary chromato-
oil. graphy and carbon-13 NMR spectroscopy.
Table 7-70 is from Formacek and New York: John Wiley & Sons.
Kubeczka (1982). Fraisse, D., Suon, K.N., Scharff, C., Vernin, G.
Vernin, G., Zamkotsian, R.M., and Metzger,
References: Peppermint J. 1985. Essential oils of curled mint. GC-MS
Clark, R.J. and Menary, R.C. 1984. Estimation Analysis-Specma Bank. Parfums, Cosmet.,
of peppermint oil constituents by capillary gas Aromes 65:71-75.
chromatography. J. Chromatog. 294:525- Green, R.J. 1975. Peppermint and spearmint
526. production in the United States: Progress and
Clark, R.J. and Menary, R.C. 1981. Variations problems. Int. Flavours Food Additives
in composition of peppermint oil in relation to 6:246-247.
production areas. Economic Botany. 35(1): Heath, H.B. 1978. Flavor Technology: Profiles,
59-69. Products, Applications. New York: AVI
Daffertshofer, G. 1981. Mentha piperata and Publishing Co.
Mentha arvensis, peppermint oils. Gordian. Kerven, G.L., Dwyer, W., Duriyaprapan, S.,
81 (112):8-11. and Britten, E.J. 1980. A semimicro ap-
324 Source Book of Flavors

paratus for essential oil determination of Commercial Sources

multiple mint samples by steam distillation.
J. Agric. Food Chern. 28(1):162-164.
Lawrence, B.M. 1979. Progress in essential oils.
Peppermint. (A monthly review). Perf. Flav.
4(5):13.
Lawrence, B.M. 1983. Progress in essential oils.
Commint oil. Perf. Flav. 8(2):61.
Lawrence, B.M. 1984. Progress in essential oils.
Perf. Flav. 9(5):87.
Lawrence, B.M. 1985. A review of the world
production of essentiai oils. Perfum. Flav. 10:
1-16.
Lawrence, B.M. 1986. Progress in essential oils.
Perf. Flav. 11(1):29.
Lawrence, B.M., Shu, C.K., and Harris, W.R.
1989. Peppermint oil defferentiation. Perf.
Flav. 14(6):21.
Murray, M.J., Marble, P., Lincoln, D., and
Hefendehl, F.W. 1988. Peppermint oil quality
differences and the reasons for them. Flavors
and Fragrances: A World Perspective Devel-
opments in Food Science, eds. B.M. Lawrence,
B.D. Mookherjee and B.J. Willis 189-210.
Amsterdam: Elsevier Science Publishers BV.
Quarre, J. 1975. Cultivation of mint in the
U.S.A. Parfum. Cosmet. Aromes 2 (Mar./
Apr.):27-30, 33-35. (French)
Royal Society of Chemistry. 1988. Application of
gas-liquid chromatography to the analysis of
essential oils determination of octen-3-ol
in oils of peppermint and mint. Analysist
113(4):657.
Pimento
See Allspice.
Poppy
The seeds of Papaver somniferum L., an
annual herbaceous plant that is indigenous
to Asia.
TABLE 7-71. Constituents of rosemary oil
France, Germany, Hungary, India, the
Netherlands, Poland and United States.
Description
Slate-colored (called "blue" commercially)
to almost white seeds; hard, kidney-shaped
with an intricately ridged surface visible
under magnification: about 1 mm long. The
seeds contain about 0-60 percent of a fixed
oil and are widely used in the baking in-
dustry for their pleasantly nutty odor and
flavor.
References
Anon 1985. Poppy seed as a raw material and its
use in fillings. Zucker und Suesswarenwirt-
schaft. 38(1):19-20.
Grosch, W. Laskawy, G. 1984. Contribution of
linoleic acid to the bitter taste of poppy seeds
(Papaver somniferum). Zeits. Lebens. Unters.
Forschung. 178(4):257-259.
Rosemary
Rosemary is the dried leaves of a small
evergreen shrub (Rosmarinus officina/is L.),
which is a native of southern Europe.
Commercial Sources Spain, France,
Portugal, Yugoslavia and the United States
(California).
Description Tightly incurled, pine
needle-like, brownish-green leaves; 2-
2.5cm long.
Volatile Oil Content l- 2 percent.
Sensory Character Light, sweetly aro-
matic and cineolic odor; the flavor is warmly
camphoraceous, herbaceous and bitter.

Compound Tunisian Moroccan Spanish u.s.

alpha-pinene 10.3-11.6 7.2-7.5 19.1-26.9 8.3-32.5
camphene 4.0-4.3 4.3-4.6 7.0-9.9 4.0-9.9
beta-pinene 4.9-7.7 4.9-5.0 4.3-7.7 1.4-9.1
limonene 2.0-4.8 1.2-1.8 2.9-4.9 2.6-4.5
1,8-cineole 40.1-44.4 41.1-43.1 17.0-25.1 4.8-28.2
camphor 9.9-12.5 11.0-13.5 12.7-20.7 1.4-46.5
bornyl acetate 1.0-1.2 1.0-l.l 0.4-1.6 0.3-14.3
borneol 2.8-4.2 2.9-3.2 2.4-3.4 0.9-17.3

Oil of Rosemary
Sources Lawrence (1985) has noted
that the annual production of rosemary oil
has decreased from about 500 metric tons to
less than 250 metric tons in 1984. The major
producers of rosemary oil are Spain (130
tons), Morocco (60 tons) and Tunisia (50
tons). Limited amounts of oil were pro-
duced in India, the former Soviet 'Dnion,
Yugoslavia, Portugal and Turkey.
Specification in EOA No. 287, FCC III
(1981), BP (1973).
A colorless to pale yellow oil; specific
gravity (25°/25°C), 0.894 to 0.912; optical
rotation (20°C), -5° to + 10°; refractive
index (20°C), 1.464 to 1.476; esters as
bornyl acetate, minimum 1.5 percent; total
alcohols as borneol, minimum 8 percent;
solubility (90 percent ethanol), 1 vol.
Constituents The composition of rose-
mary oil has been discussed by Lawrence
(1986) and Boelens (1985). Boelens (1985)
has included a very broad treatment of
the Spanish oil including history, botany,
essential oil production, physiochemical
properties, chemical composition, olfactory
properties, applications and trade. While
Table 7-71 lists the amounts of the major
constituents of rosemary oil (Lawrence
1983), more detail on the composition of
Spanish (Barranco et al. 1980), USSR
(Abbasov et al. 1982) and Romanian
(Hodisan 1984) oils can be found in the
literature as noted.
Oleoresin Rosemary
A green to brownish-green semisolid to
pasty oleoresin, which is fluid when warmed
TABLE 7-72. Commercially available rosemary
oleoresins
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/100g) (%) (%)
3-5 14 0.42-0.70
max 10 4 max0.4
10-15 4-7
0.4-1.05
34-40 3.5 1.19-1.4
Natural Flavoring Materials 325
to 50°C. The commercially available oleo-
resins are shown in Table 7-72.
Natural Antioxidants in Rosemary and Sage
Rosemary and sage herbs when used in
seasonings are known to contain antioxidant
constituents, which contribute to the reten-
tion of a good red color in processed meats
(Chipault et al. 1956; Klingenberg and
Verstrynge 1989). The volatile oils have
been shown not to contain these constituents
and hence do not have an antioxidant pro-
perty, but they are present in the oleoresins.
Unfortunately, these two spices have a high
level of aroma and flavor components that
limit their use level to a restricted range of
products. Chang et al. (1977) reported a
patented process for the solvent extraction
of rosemary and sage herbs followed by the
vacuum-steam or molecular distillation of
the extract in an edible oil or fat carrier to
give a colorless, bland, natural antioxidant
in a yield of about 5 percent when methanol
is used as the solvent. It is claimed that
this natural antioxidant at 0.02 percent is
superior to the permitted synthetic anti-
oxidants (e.g., BHA, BHT, etc.) and that
the action is enhanced by the addition of
0.05 percent ascorbic acid. The chemical
nature of the components responsible for
this antioxidant property has not yet been
established.
References: Rosemary
Abbasov, R.M., Mishurova, S.S., Malinovskaya,
T.A., and Bakshieva, S.S. 1982. Study of
Rosemary Oil in Apsheron. Deposited
Document VINITI 786-83, 6pp.
Barranco, R., Carrasco, J., Martin, E., and
Frasquet, F. 1980. Etude comparative entre
les huiles essentielles de romain sylvestre et
cultive. Paper No. 110, 8th International
Essential Oil Congress, Cannes.
Berset, C., Trouiller, J., and Marty, C. 1989.
Protective effect of the oleoresin of rosemary
(Rosmarinus officina/is L.) and of several
other antioxidants on beta-carotene in ex-
trusion cooking. Lebens. Wissen. Techno!.
22(1):15-19.
Boelens, M.H. 1985. The essential oil from
326 Source Book of Flavors
Rosmarinus officina/is L. Perf Flav. 10(5):
21-38.
Chang, S.S., Matijasevic, B.O., Hsieh, O.A.L.,
and Huang, C.L. 1977. Natural antioxidants
from rosemary and sage. J. Food Sci. 42:
1102-1106.
Chiqault, J.R. et a!. 1956. The antioxidant
properties of spices in foods. Food Techno/.
10:209.
Hodisan, V., Popescu, H., and Lazar, M. 1984.
Volatile oil of Rosmarinus officina/is L. of
Romanian origin. C/uju/. Med. 57:374-377.
International Organization for Standardization
1988. Oil of rosemary (Rosmarinus officina/is
Linnaeus). International Standard. ISO 1342:
1988, 10pp.
Klingenberg, A. and Verstrynge, L. 1989.
Rosemary extract, a natural antioxidant.
Voedingsmidde/entechnologie. 22(18):36-37.
Koedam, A., Scheffer, J.J.C., and Baerheim,
Svendsen, A. 1980. Comparison of isolation
procedures for essential oils. VI. Rosemary
and sage. Riechstoffe, Aromen, Kosmetica.
30(10):271-276.
Lawrence, B.M. 1977. Progress in essential oils.
Rosemary. (A monthly review.) Perf. Flav.
2(4):34.
Lawrence, B.M. 1982/1983. Progress in essential
oils. Perf. Flav. 7(6):20.
Lawrence, B.M. 1985. A review of the world
production of essential oils. Perf. Flavorist
10:1-16.
Lawrence, B.M. 1986. Progress in essential oils.
Rosemary oil. Perf. Flav. 11(2):75.
Tucker, A.O. and Maciarello, M.J. 1986. The
essential oils of some rosemary cultivars. Flav.
Frag. J. 1(4/5):137-142.
Saffron
Saffron is the dried stigmas of a crocus
(Crocus satiuus L.) that is cultivated in
several European countries, principally in
Spain and France, northern India and
China. The reddish-lilac flowers appear in
October and each has a long bright red
stigma. Usually, the whole flowers are
gathered and the stigmas removed by hand;
these are then dried to form the commercial
spice (Sampathu, Shivashankar and Lewis
1984). The yield is small and it takes 30,000
to 35,000 hand-picked blooms to give just
lib. of dried saffron. Genuine saffron
should not be confused with safflower
(Mexican saffron), which is the tubular
florets of Carmanthus tinctorius L., an
annual thistle-like plant that grows in
central Mexico.
Commercial sources Spain (Valencia,
Alicante), France, China.
Description Loosely matted, fila-
mentous mass of dark-red to reddish-brown
stigmas; 2-2.5 em long; yellow styles may
sometimes be present.
Sensory Character Saffron has an
intense, characteristic odor that is not to
everyone's liking; the flavor is delicate with
a sharply bitter back-note. Safflower lacks
the flavor characters of genuine saffron.
Saffron is valued primarily for its water-
soluble yellow coloring matter.
Constituents Saffron contains (a) a
highly aromatic essential oil (0.5-1 percent),
the monoterpene aldehydes and isophorone-
related compounds, which were investigated
by Zarghami et al. (1971) and Solinas and
Cichelli (1988); (b) picrocrocin, a colorless
bitter glucoside of an aldehyde, safranal,
and (c) crocin, a bright yellow digentiobiose
ester. Crocin and picrocrocin are believed to
originate from a ~-carotene type percursor
(Fieser and Fieser 1956) to give compounds
::r·
having the following structural formulas:
YH, ~H, YH,
~c=cHCH==cH&z...cHcH==cHCH==cc~HCH
Ct2H2t0to
O<:tzH:nOto
crocin gentiobiose
CsHuOs·O
glucose
picrocrocin
The carotenoid composition of saffron
was investigated by Pfander and Wittwer
(1975) and Solinas and Cichelli (1988). The
bitter principle in safflower, matairesinol

monoglucoside, was examined by Palter
and Lundin (1970); the coloring matter
present is reported as saffron-yellow (about
30 percent) and saffron-red (about 0.5
percent).
References: Saffron
Fieser, L.F. and Fieser, M. 1956. Organic
Chemistry, 3rd Edition. New York: Reinhold
Publishing Corp.
International Organization for Standardization.
1980. Saffron-Specification. International-
Standard. ISO 3632:1980, 9pp.
Kamikura, M. and Nakazato, K. 1984. Com-
parison of the natural yellow colours extracted
from saffron (Crocus sativus Lin~) and
gardenia fruit (Gardenia jasminoides Ellis).
Bulletin of the National Institute of Hygienic
Sciences [Eisei-Shikenjo-Hokoku]. 103:157-
160.
Lewis, Y.S., Sampathu, S.R., Shivashankar, S.,
and Natarajan, C.P. 1981. Quality evaluation
of saffron. Indian Cocoa, Arecanut & Spices
Journal. 4(4):113-115.
Palter, R. and Lundin, R.E. 1970. A bitter prin-
ciple of safflower matairesinol monoglucoside.
Phytochem. 9:2407-2409.
Sampathu, S.R., Shivashankar, S., and Lewis,
Y.S. 1984. Saffron (Crocus sativus L.) cultiva-
tion, processing, chemistry and standard-
ization. CRC Critical Reviews in Food Science
and Nutrition. 20(2):123-157.
Solinas, M. and Cichelli, A. 1988. HPLC analysis
of the constituents responsible for the colour
and aroma of saffron. Industrie-Alimentari.
27(262):634-639, 648.
Sage
Many Salvia species and varieties are known
in commerce simply as "sage," being dif-
ferentiated by the name of the place from
which they were derived: The following are
the most important of these:
Dalmatian sage (Salvia officina/is L.)
English sage (S. officina/is L.)
Greek sage (S. triloba L.)
Spanish sage (S. lavandulaefolia [L.] Vahl.)
Dalmatian Sage
Sage is the dried leaves of a small perennial
shrub (Salvia officina/is L.) native to the
Natural Flavoring Materials 327
Mediterranean region, where it grows pro-
fusely on the rocky hillsides of the Adriatic
coast of Yugoslavia and Albania.
Commercial Sources Yugoslavia (Dal-
matia), Albania, Turkey, Italy, the former
Soviet Union.
Description Grayish-green to silvery-
gray elongated oval to lanceolate whole or
broken leaves; 5-7.5 em long; fragments of
petioles and short pieces of stalk may be
present. The leaf surface is covered with fine
short hairs giving the dried herb a fluffy,
matted appearance. The appearance of
other varieties of sage may be different,
many not having the characteristic woolly
texture of Dalmatian sage, being hard and
brittle (e.g., English sage).
Volatile Oil Content 1.5-3 percent.
Sensory Character Strongly fragrant,
warmly aromatic, camphoraceous odor; the
flavor is distinctive, heavy and thujone-like.
Oil of Dalmatian Sage
Sources The annual production of
Dalmatian sage oil was estimated as being
about 40 metric tons in 1984 (Lawrence
1985). Albania (25 tons) and Yugoslavia (15
tons) are the major producers of this oil.
Specification in EOA No 44, FCC III
(1981).
A pale yellow to greenish-yellow oil;
specific gravity (25°/25°C), 0.903 to 0.925;
optical rotation (20°C), +2o to +29°; refrac-
tive index (20°C), 1.457 to 1.469; solubility
(80 percent ethanol), 1 vol; saponification
value, 6 to 20; ester value after acetylation,
25 to 60; ketones as thujone, minimum 50
percent.
Constituents Lawrence has provided
several recent reviews on the composition of
sage oil (Lawrence 1981, 1983, 1985, 1986).
Data on the composition of Dalmatian sage
as published by Formacek and Kubeczka
(1982) is given below:
cis-salvene (0.64%) trans-salvene (0.10%)
tricyclene (0.23%) a-pinene+ ~-thujene
(3.88%) camphene (7.37%) ~-pinene
(2.33%) sabinene (0.12%) myrcene
(1.14%) a-phellandrene (0.06%)
328 Source Book of Flavors

TABLE 7-73. Constituents of Greek sage oils

Compound Arcadoa Thesprotia Cefallonia Chios Crete Lesvos Rhodes Syros

a-pinene 5.0 ~.7 5.2 4.8 4.3 4.4 3.8 6.7

camphene 7.5 0.8 5.5 0.4 0.5 0.6 0.4 2.5
P-pinene 10.7 6.4 3.0 8.8 9.3 6.2 6.8 4.2
myrcene 0.6 2.7 3.5 3.4 3.3 6.7 3.4
1,8-cineole 38.8 65.1 56.7 59.4 62.2 65.7 66.2 58.2
thujone 5.3 4.2 4.6 1.4 5.5 4.5 12.1 58.2
camphor 23.8 5.5 15.5 10.4 3.9 1.7 1.9 14.2
linalool 1.5 1.2 1.0 0.4 1.4 2.9
isopulegol 2.2 0.6 0.3 0.8 0.3 trace 0.6
isoborneol 0.7 0.1 0.4 1.8
linalyl acetate 0.1 0.6 0.3 0.1 0.3 0.5 0.4 0.7
bornyl acetate 0.3 0.2 0.1 0.1 0.3 0.3 0.4 0.6
citronellyl acetate 0.5 0.1 0.5 0.1 0.6 0.4 0.1 0.3
caryophyllene 1.2 2.4 1.3 7.3 4.5 4.5 2.2 1.4

a-terpinene (0.20%) limonene (3.24%) data presented in Table 7-73 are of Greek
1,8-cineole (11.34%) terpinolene (0.30%) oils (S. triloba) obtained from different
a-thujone (25.88%) B-thujone (2.69%) districts or islands of Greece (Katsiotis and
a-copaene (0.14%) camphor (22.80%) Iconomu 1984).
linalool (0.48%) bornyl acetate (1.23%) Oleoresin dalmatian sage A dark green
B-caryophyllene (3.29%) a-humulene to brownish-green viscous oleoresin. The
(5.31%) borneol+ a-terpinyl acetate prime oleoresin contains about 10 percent
(3.55%) 8-cadinene (0.23%) cis-B-ocimene volatile oil, but most commercial products
(0.07%) y-terpinene (0.39%) p-cymene contain additional distilled essential oil.
(0.64%) caryophyllene oxide (0.13%) Propylene glycol may be used to give a more
viridiftorol (0.83%) readily handled product to a maximum of 37
percent in the oleoresin. The oleoresins
Further information on the composition available commercially are shown in Table
of S. officicalis oil-Yugoslavian origin 7-74.
(Pitarevic 1984; Kustrak et al. 1984) and Propylene glycol, lecithin, mono-, di- and
Hungarian origin (Lemberkovics, Petri and triglycerides may be present as specified by
Tamas 1988)-and S. triloba oil-Greek the manfacturer.
origin (Katsiotis and Iconomu 1984) and Antioxidant Properties of Sage-See
Turkish origin (Buil et al. 1977)-is avail- Rosemary.
able as noted in the cited references. The
Spanish Sage
TABLE 7-74. Commercially available Dalmatian This herb is a relatively minor article of
sage oleoresins
commerce that is distilled mainly in the
Volatile Oil Suggested Volatile Oil growing region (Granada, Murcia, Almeria
Content Use Rate in Dispersion and Jaen) (Guenther 1948-1952).
(ml/100 g) (%) (%) Oil of Spanish Sage Obtained by the
25-30 6-9 1.5-2.7 distillation of the freshly harvested leaves of
30-32 5 1.5-1.6 S. lauandulaefolia or S. hispanorum Lang.
30-40 3.3 0.99-1.32 in a yield of about 0.7 percent. It was
48-52 not specified estimated that about 5 metric tons were
min65 5.5 min 3.58 produced worldwide in 1984 (Lawrence
65-70 2 1.3-1.4
1985).
 Natural Flavoring Materials 329

TABLE 7-75. Constituents of Spanish sage oil

a-thujene (0.2%) linalool + linalyl acetate +

a-pinene (8.6%) a-gurjunene +
camphene (7.0%) cis-a-bergamontene (3.6%)
~-pinene (4.5%) bornyl acetate +
sabinene (1.3%) trans-a-bergamotene (1.6%)
myrcene (3.2%) geraniol (0.4%)
limonene (4.5%) terpinen-4-ol +
1,8-cineole + cis-ocimene (23.2%) caryophyllene + aromadendrene (1.0%)
trans-ocimene (0.4%) li-terpineol +
y-terpinene (trace) allo-aromadendrene (0.1%)
p-cymene (1.9%) camphor (20.1%)
terpinolene (trace) cis-sabinyl acetate (3.0%)
cis-,cis-allo-ocimene (0.1%) cis-sabinol + a-humulene +borneol (0.3%)
a-p-dimethylstyrene (0.3%) a-terpineol (trace)
trans-sabinene hydrate (0.5%) a-terpinyl acetate (11.2%)
li-cadinene (0.4%)
a-cubebene (trace) ar. curcumene (0.4%)
copaene (trace) nero! (0.1%)

Specification in EOA No. 71, FCC III
(1981).
A colorless to very pale yellow oil; specific
gravity (25°/25°C), 0.909 to 0.932; optical
rotation (20°C), -3° to +24°; refractive
index (20°C), 1.468 to 1.473; saponification
value, 14 to 57; saponification value after
acetylation, 56 to 98; solubility (80 percent
ethanol), 2 vol.
Sensory Character Fresh, sharply pene-
trating, cineolic-camphoraceous odor; flavor
is bitter with a sharp green herbaceous
character.
Constituents The composition of
Spanish sage oil has been reviewed by
Lawrence 1984/85. The components listed
in the Table 7-75 have been reported by
Lawrence et al. (1970) (Table 7-75). More
recent work has been published by Formacek
and Kubeczka (1982).
References: Sage
Buil, P., Garnero, J., Guichard, G., and Konur,
Z. 1977. Sur quelques huiles essentielles en
provenance de Turquie. Rivista Ita/. 59:379-
384.
El Keltawi, N.E. and Croteau, R. 1987.
Influence of herbicides and growth regulators
on the growth and essential oil content of
sage. Phytochem. 26(3):675-679.
Formacek, K. and Kubeczka, K.H. 1982.
Essential oils analysis by capillary chromato-
graphy and carbon-13 NMR spectroscopy.
New York: John Wiley & Sons.
Gecan, J.S., Bandler, R., Glaze, L.E., and
Atkinson, J.C. 1986. Microanalytical quality
of ground and unground marjoram, sage and
thyme, ground allspice, black pepper and
paprika. J. Food Protect. 49(3):216-221.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
Katsiotis, S. and Iconomu, N.G. 1984. Qualitative
and Quantitative Comparative Gas-Liquid
Chromatographic Analysis of the Essential
Oil of Salvia triloba Grown in Greece. Pharm.
Acta Helv. 59:29-32.
Kustrak, D., Kuftinec, J., and Blazevic, N. 1984.
Yields and Composition of Sage Oils from
Different Regions ofthe Yugoslavian Adriatic
Coast. J. Nat. Prod. 47:520-524.
Lawrence, B.M., Hogg, J.W., and Terhune, S.J.
1970. Essential Oils and Their Constituents.
III. Some New Constituents in the Essential
Oil of Salvia lavandulaefolia Vahl. J.
Chromatog. 50:59-65.
Lawrence, B.M. 1971. Essential oils and their
constituents. IV. Some new trace constituents
in the essential oil of Salvia officina/is L.
Parfum. Cosmet. Savons Fr. 1(May):256-
259. (French)
Lawrence, B.M. 1977-1978. Progress in essen-
tial oils. Sage. (A monthly review.) Perf. Flav.
2(4):41, 2(5):50.
330 Source Book of Flavors

Lawrence, B.M. 1981. Progress in essential oils. TABLE 7-76. Constituents of oil of savory
Perf. Flav. 6(2):59.
North
Lawrence, B.M. 1983. Progress in essential oils.
Compound Europe Canada Africa
Perf Flav. 8(1):61.
Lawrence, B.M. 198411985. Progress in essential a-thujene 3.1 1.8 4.2
oils. Perf. Flav. 9(6):61. camphene trace trace 6.3
Lawrence, B.M. 1985. A review of the world P-pinene 0.4 0.2 0.8
production of essential oils Perfum. Flavorist myrcene 2.8 1.7 0.5
10:1-16. a-terpinene 0.4 3.8 0.6
Lemberkovics, E., Petri, G., and Tamas, J. 1988. limonene 5.3 0.2 1.1
y-terpinene 60.3 34.1 2.1
Gas chromatographic determination of mono-
p-cymene 4.5 5.3 3.7
and sesquiterpenes in some commercial
terpinolene trace trace 0.1
Hungarian essential oils. In Flavors and 1-octen-3-ol trace 0.1 0.1
Fragrances: A World Perspective. Proceedings camphor 3.3
of the lOth International Congress of Essen- linalool 0.1 0.1
tial Oils, eds. B.M. Lawrence, B.D. bornyl acetate 1.7
Mookherjee, and B.J. Willis, pp. 243-247. terpinen-4-ol 0.5 1.2 11.2
New York: Elsevier. methyl carvacrol 0.2 0.8 0.3
Maciarello, M.J. 1990. Essential oils of cultivars borneol trace 0.1 34.0
of Dalmatian sage (Salvia officinalis L.). a-terpineol trace 0.1 0.3
P-bisabolene 0.2 0.7 0.8
J. Essent. Oil Tes. 2(3):139-144.
a-humulene 0.1
Mazza, G. 1988a. The aroma of clary sage. I. 1>-cadinene trace 0.8
trace
Identification of volatiles in the essential oil p-cymene-8-ol 0.2 trace
and in aqueous/alcoholic infusions of the caryophyllene oxide trace 0.5
flower tips. Sci. Aliments. 8(4):489-510. 10-epi(a)-cadinol 0.6
Mazza, G. 1988b. The aroma of clary sage. II. thymol trace 0.2 22.5
Identification of volatiles in the essential oil carvacrol 18.2 50.4 3.4
and in aqueous/alcoholic infusions of the
leaves. Sci. Aliments. 8(4):511-522.
Shelef, L.A., Naglik, O.A., and Bogen, D.W. distilled to give about 0.25 percent of essen-
1980. Sensitivity of some common food-borne tial oil. Most commercial samples are of
bacteria to the spices sage, rosemary, and
summer savory.
allspice. J. Food Sci. 45(4):1042-1044.
Verzar, Petri, G., Then, M., and Meszaros, S.
1985. Formation of essential oil in clary sage Commercial Sources
under different conditions. In Essential Oils Southern France, Germany, Spain, Italy,
and Aromatic Plants, eds. A.B. Svendsen and United Kingdom, United States (Midwest).
J.J.C. Scheffer, pp. 199-202. Netherlands:
Martinus Nijhoff. Description
The dried herb consists of brownish-green,
Savory whole infolded leaves; 4-5 em long with
There are two distinct species of savory some stem fragments. Surface oil glands are
herb: Summer savory is derived from visible under magnification.
Satureia hortensis L., an annual plant
cultivated throughout France and the Oil of Savory (Summer Savory)
Mediterranean region, harvested when in Sources Lawrence (1985) estimated
flower in June/July and distilled to give that fewer than 0.5 metric tons of savory oil
about 0.2 percent volatile oil. Winter savory were manufactured in 1984. The primary
is derived from Satureia montana L., a small producing countries were France (400 kg),
hardy shrub that grows wild in southern Hungary (400kg), Spain, the Netherlands,
France, harvested when in bloom and the USSR and Yugoslovia.

Specification in EOA No. 197, FCC III
(1981).
A light yellow to pale brown oil; specific
gravity (25°/25°C), 0.875 to 0.954; optical
rotation (20°C), -5° to +4°; refractive index
(20°C), 1.486 to 1.505; phenols as carvacrol,
20 to 57 percent; saponification value, max
6; solubility (80 percent ethanol), 2 vol.
Sensory Characters Warmly aromatic
odor reminiscent of thyme and origanum;
the flavor is sharp and herbaceous.
Constituents Lawrence (1981) has
reviewed the chemical composition of
summer savory oil. He reported identifying
the constituents shown in Table 7-76.
References
Heath, H. 1974. Herbs and spices-a biblio-
graphy. VIII. Saffron and safflower; sage;
savory. Flav. Ind 5(3/4):79-81.
Lawrence, B.M. 1981. Progress in essential oils.
Savory oil. Perf. Flav. 6(4):73.
Lawrence, B.M. 1985. A review of the world
production of essential oils. Perf Flav. 10(5):
1-20.
Sesame
The sesame of commerce is the hulled seeds
of an annual herbaceous plant (Sesamum
indicum L.), which is native to Asia. The
unhulled seeds vary in color from yellowish-
white to brown to almost black, but it is the
hulled seeds that are widely used in the
baking industry.
Description
The hulled seeds are clean, creamy white,
oval and compressed; 2-3mm long and
having a minute protruberance at one end.
They are shiny, smooth and somewhat
slippery to the touch.
Sensory Characters
Sweetly nutty odor and flavor.
Fixed Oil Content
44-54 percent. Sesame seed oil is claimed to
have antioxidant properties when added to
Natural Flavoring Materials 331
other fats (Triebold and Aurand 1963) due
to the presence of sesamol, the glycoside
of which, sesamolin, is found in the
unsaponifiable matter of sesame seed oil:
sesamol
References: Sesame
El-Sawy, A.A., Soliman, M.M., and Fadel,
H.M. 1988. Identification of volatile flavour
components of roasted red sesame seeds.
Grasas-y-Aceites 39(3): 160-162.
El-Sharkawy, A.A., Rady, A.H., Mostafa,
M.M., and Kandil, S.H. 1986. Changes in
main components of raw and roasted peanut
and sesame seeds. I. Oil properties, fatty acid
composition, hydrocarbons and sterol con-
stituents. Egyptian J. Food Sci. 14(1):13-22.
Parry, J.W. 1969. Spices, Vol. 1 and 2. New
York: Chemical Publishing Co.
Spearmint
The designation "spearmint" is applied
commercially to several species and varieties
of the genus Mentha possessing a distinct
and characteristic odor profile. The plants
resemble those of peppermint, and are culti-
vated and harvested in a similar manner.
The main species and varieties are: Mentha
spicata (L.) Huds. var. tenuis Mich. (USA),
formerly classified as Mentha viridis L.; var.
trichoura Briq. (UK); var. crispata Benth.
(Germany and Japan); Mentha verticillata
L. var. strabola Briq. (the former Soviet
Union) (Guenther 1949). Scotch mint (M.
cardiaca Gerard ex Baker) is also cultivated
in the United States. Most of the crop is
distilled in the growing region, but some
herb is dried and rubbed for domestic use.
Small crops are grown and harvested spe-
cially for use in mint sauce and jelly.
Oil of Spearmint
Obtained by the steam distillation of the
332 Source Book of Flavors
fresh herb harvested when in bloom and
usually redistilled or rectified before use.
Sources According to Lawrence (1985)
two types of spearmint oil are produced in
the United States: a Scotch oil and various
native oils. The U.S. was estimated to have
produced about 1000 metric tons of the
combined oils in 1984. In addition, China
(300 tons), Italy, Brazil, Japan, France, and
South Africa produced significant amounts
of oil.
Specification in EOA No 57, FCC III
(1981).
A colorless to very pale straw-colored oil;
specific gravity (25°/25°C), 0.917 to 0.934;
optical rotation (20°C), -48° to -59°; re-
fractive index, 1.484 to 1.491; ketones, min
55 percent; solubility (80 percent ethanol),
1 vol.
Sensory Character Sharply fresh green
minty odor; flavor is warm, smoothly
aromatic and herbaceous.
Constituents The composition of spear-
mint oil has been discussed by Lawrence
(1976). A more recent study on the major
constituents of Scotch spearmint (Mentha
gentilis f. cardiaca (Sm.) Briq.) has reported
a-pinene (1.2 percent), ~-pinene (1.1 per-
cent), sabinene (0.9 percent), myrcene
(1.5 percent), limonene (19.7 percent),
1,8-cineole (2.8 percent), 3-octanol (3.1
percent), (- )-carvone (54.6 percent), trans-
carveol (5.8 percent) and cis-carveol (1.7
percent) (Shimizu et al. 1990). Additional
work has been reported by Maffei, Codignola
and Fieschi (1986).
References: Spearmint
Association Francaise de Normalisation. 1986.
Essential oils. Essential oil of spearmint
(Mentha spicata). French Standard NF T 75-
245:6pp.
Canova, L. 1972. The composition of Scotch
spearmint oil. Ann. Acad. Brasil. Cienc. 44
(suppl):273-277.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I-VI. New York: D. Van Nostrand Co.
International Organization for Standardization.
1988. Oil of spearmint (Mentha spicata
Linnaeus). International-Standard. ISO 3033:
1988. 4 pp.
Lawrence, B.M. 1976. Progress in essential oils.
Spearmint. (A monthly review.) Perf. Flav.
1(1):34.
Lawrence, B.M. 1985. A review ofthe world pro-
duction of essential oils. Perf. Flav.10(5):1-20.
Maffei, M., Codignola, A., and Fieschi, M. 1986.
Essential oil from Mentha spicata L. (spear-
mint) cultivated in Italy. Flav. Frag. J. 1(3):
105-109.
Misra-LN; Tyagi-BR; Thakur-RS. 1989.
Chemotypic variation in Indian spearmint.
Planta-Medica 55(6):575-576.
Murray, M.J., Faas, W., and Marble, P. 1972.
Effects of plant maturity on oil composition of
several spearmint species grown in Indiana
and Michigan. Crop-Sci 12(6):723-728.
Shimizu, S., Shibata, H. and Maejima, S. 1990.
A new monoterpene glucoside l-menthyl6'su-
O-acetyl-beta-D-glucoside in Mentha arvensis
var. piperascens Mal. I. Studies on terpene
glucosides in Mentha plants. Journal of
Essential Oil Research. 2(1):21-24.
Shimizu, S., Shibata, H., Karasawa, D. and
Kozaki, T. 1990. Studies on terpene glycosides
in Mentha plants. II. Carvyl- and dihydro-
carvyl-beta-D-glucosides in spearmint. Jour-
nal of Essential Oil Research. 2(2):81-86.
Star Anise
See Anise.
Sweet Basil
See Basil.
Sweet Bay
See Bay Laurel.
Sweet Marjoram
See Marjoram, sweet.
Sweet Savory
See Savory.
Ta"agon (Estragon)
Tarragon is the dried leaves and flowering
tops of Artemisia dracunculus L., a small
herbaceous perennial native to Asia. There
are two recognized varieties of this species
-Russian and French; the latter is pre-
 Natural Flavoring Materials 333

ferred and is the one grown in the United TABLE 7-77. Commercially available tarragon
States. oleoresins

Volatile Oil Suggested Volatile Oil

Commercial Sources Content Use Rate in Dispersion
Southern France, United States. (ml/100 g) (%) (%)

12-15 2-3 0.24-0.45

Description
The dried herb consists of green lanceolate
leaves with in-curled edges, about 4 em long
and 3-3.5mm wide.
Volatile Oil Content
The fresh herb yields about 1.5 to 2.5
percent of essential oil, but this is reduced to
about 0.8 percent in the dried herb.
Sensory Character
Characteristic, delicately spicy, anisic odor;
the flavor is herbaceous and basil-like.
Oil of Tarragon (Estragon)
Oil of tarragon is obtained by the steam
distillation of the fresh herb harvested when
in bloom. Approximately 8 metric tons were
produced in Italy in 1984 (Lawrence 1985).
Limited quantities were also produced in
Morocco, Yugoslovia, Hungary and South
Africa to bring world production to about 10
metric tons.
Specification in EOA No. 121
(Estragon), FCC III (1981).
A pale yellow to amber oil; specific
gravity (25°/25°C), 0.914 to 0.956; optical
rotation (20°C), + 1.SO to +6.SO; refractive
index, 1.504 to 1.520; acid value, max 2;
saponification value, max 18; solubility (90
percent ethanol), 0.5 to 1 vol.
Constituents The chemical composition
of tarragon oil was reviewed some time ago
by Lawrence (1977, 1979). Thieme and Tam
(1972) identified the following constituents in
tarragon oil: a-pinene, camphene, ~-pinene,
limonene, cis-ocimene, transocimene,
methyl chavicol, p-methoxy cinnamic
aldehyde, £-4-carene, a-phellandrene and
linalool. Later work by Zarghami and
Russell (1973) confirmed these compounds
and reported in addition: cis- and trans-
alloocimene, linalool, butyric acid, geraneol,
14-18 0.35-0.43
2.5
1,2-dimethoxy-4-allyl benzene and eugenol.
Methyl chavicol is reported as the major
component (about 65 percent). The syn-
thetic version of this compound is some-
times used to extend the natural oil, but
such compounded oils are generally "thin"
by comparison and air off very quickly
(Heath 1978).
Oleoresin Tarragon
A dark green viscous oleoresin. The oleo-
resins available commercially are shown in
Table 7-77.
References: Tarragon (Estragon)
Heath, H.B. 1974. Herbs and spices-A biblio-
graphy. IX. Tarragon; thyme; turmeric. Flav.
Ind. 5(5/6): 123-124.
Heath, H.B. 1978. Flavor Technology: Profiles,
Products, Applications. New York: AVI
Publishing Co.
Lawrence, B.M. 1985. A review of the world
production of essential oils. Perf. Flav. 10(5):
1-20.
Lawrence, B.M. 1977. Progress in essential oils.
Tarragon. (A monthly review.) Perf. Flav.
2(3):5G.
Tateo, F., Santamaria, L., Bianchi, L., Bianchi,
A. 1989. Basil oil and tarragon oil: composi-
tion and genotoxicity evaluation. J. Essen. Oil
Res. 1(3):111-118.
Thieme, H., Tam, N.T. 1972. Examination of
the formation and composition of essential oil
of Satureia hortensis L., S. montana L. and
Artemisia dracunculus. L. Pharmazie 27:255-
265. (German).
Vostrowsky, 0., Michaelis, K., Ihm, H., Zintl,
R., Knobloch, K. 1981. Components of
essential oil from tarragon (Artermisia
dracunculus L.). Ueber die Komponenten des
aetherischen Oels aus Estragon (Artemisia
334 Source Book of Flavors

dracunculus L.). Zeitsch. Lebens. Unters. 90 percent of the thyme oil produced in the
Forsch. 173(5):365-367. world comes from Spain (Lawrence 1985).
Zarghami-NS; Russell-OF. 1973. The vola- Additional oil comes from Yugoslavia,
tile constituents of tarragon (Artemisia dra- Morocco, Portugal and Israel.
cunulus). Chemie-Mikrobiologie- Technologie-
Specification in EOA No. 286.
der-Lebensmittel 2(6): 184-186.
A colorless to deep reddish-colored oil;
specific gravity (25°25°C), 0.910 to 0.935;
Thyme optical rotation (20°C), oo to -3°; refractive
The botanical source of so-called "thyme" is index (20°C), 1.495 to 1.505; total phenols,
somewhat involved. Commercial thyme min 40 percent by volume; solubility (80
herb is the dried leaves of a perennial percent ethanol), 2 vol.
herbaceous plant, which may be either Constituents The chemical composition
Thymus vulgaris L., T. zygis L. or other of thyme oils has been reviewed by
closely related species. These plants are Lawrence (1981, 1982, 1984). The chemical
native to southern Europe and are found in composition of thyme oil derived from
many local varieties. They are characterized Thymus vulgaris (one sample) and Thymus
by producing an essential oil containing at zygis (five samples) of Spanish origin is
least 40% total phenols, of which 90% is presented below (Mateo et al. 1979).
thymol (Arctander 1960). Wild thyme is Weisner and Weisner (1980) noted that
derived from T. serpyllum L. and Moroccan Thymus pannonicus of Czechoslovakian
thyme from T. satureioides Cass. The dif- origin yielded an oil very similar to that of
ferentiation of these species is discussed by T. vulgarus. Agarwal and Mathela (1978)
Lawrence (1977). and Razdan and Koul (1975) have published
information on the chemical composition of
Commercial Sources wild thyme oil (Thymus serpyllum). (Table
Spain, France, Portugal, Italy, Germany, 7-78).
Morocco, Algeria, Egypt and the United
States.
TABLE 7-78. Constituents of wild thyme oil
Description Thymus Thymus
Dried thyme herb consists of brownish- Compounds vulgaris zygis
green to gray-green small in-curled leaves
a-pinene 5.1 0.9-6.6
with a few stem fragments; 2-5 mm long. camphene 11.4 0.4-8.0
Surface oil glands are visible under ~-pinene 2.8 0.3-2.1
magnification. sabinene 0.6 0.0-1.0
myrcene 5.4 0.7-5.2
Volatile Oil Content limonene 3.0 0.3-1.6
1,8-cineole 33.0 0.2-14.2
2-5 percent. y-terpinene 6.1 3.4-13.0
p-cymene 6.8 9.1-22.4
Sensory Character camphor 14.5 0.0-11.3
Sweetly aromatic, warmly pungent odor; Iinalool 0.9 2.2-4.8
the flavor is sharp, rich, warmly phenolic. linalyl acetate 0.0 0.0-0.9
caryophyllene 0.9 0.3-2.0
a-terpineol 1.5 0.0-1.5
OilofThyme borneol 3.5 0.6-7.5
Two types are recognized commercially- allo-aromadendrene 0.0 0.0-0.1
Red and White. The former is the natural terpinen-4-ol 2.4 0.0-1.7
distillate; the latter is a redistilled red thyme methoxycarvacrol trace trace-3.0
thymol trace 11.7-61.1
oil; although compounded oils are fre- carvacrol 0.0 0.4-20.6
quently offered under this title. More than

TABLE 7-79. Commercially available thyme
oleoresins
Volatile Oil Suggested Volatile Oil
Content Use Rate in Dispersion
(ml/100 g) (%) (%)
max 10 5 max 0.5
50 4 2
54-60 0.75 0.40-0.45
Herisset et al. (1973) noted that in the oil
of T. vulgaris, thymol and terpinen-4-ol
predominate; in that of T. zygis and T.
serpyllum, thymol, linalool and linalyl
acetate are the major components; whereas
in T. satureioides there is a high a-terpineol
and borneol content. This last component
was used by Richard et al. (1975) to detect
the admixture of Moroccan and French
thyme oils, as the latter does not normally
contain a significant amount of this
compound.
Oleoresin Thyme
A green to brownish-green semisolid,
pasty oleoresin, which becomes fluid when
warmed to 50°C. The prime oleoresin
contains about 10 percent of volatile oil, but
most commercial products are admixed with
distilled oil to give a much higher content.
The preparation of thyme extracts was
described by Kala et al. (1976).
The oleoresins available commercially
are shown in Table 7-79.
References: Thyme
Agarwal, 1., and Mathela, C.S. 1978. Chemical
composition of essential oil of Thymus
serpyllum L. Proc. Nat. Acad. Sci. (India),
48A:144-146.
Aktug, S.E. and Karapinar, M., 1986. Sensitivity
of some common food-poisoning bacteria to
thyme, mint and bay leaves. Internal. J. Food
Microbia. 3(6):349-354.
Arctander, S. 1960. Perfume and Flavor Materials
of Natural Origin. Elizabeth: Steffen
Arctander.
Benjilali, B., Hammoumi, M. and Richard, H.
1987. Chemical polymorphism of essential oil
Natural Flavoring Materials 335
or Moroccan thyme. I. Characterization of
constituents. Sci. Aliments 7(1):77 -91.
Benjilali, B., Hammoumi, M., M'hamedi, A.,
and Richard, H. 1987. Chemical composition
of essential oils of various Moroccan thyme
varieties. II. Principal component analysis.
Sci. Aliments. 7(2):275-299.
Bestmann, H.J., Erler, J., Vostrovsky, 0. 1985.
Extraction of thyme with liquid C0 2 on a
laboratory scale. Zeits. Lebens. Unters.
Forsch. 180(6):491-493.
Farag, R.S., Badei, A.Z.M.A., and El-Baroty,
G.S.A. 1989. Influence of thyme and clove
essential oils on cottonseed oil oxidation.
J. Amer. Oil Chern. Soc. 66(6):800-804.
Heath, H. 1974. Herbs and spices-A biblio-
graphy. IX. Tarragon; thyme; turmeric. Flav.
Ind. 5(5/6):123-124.
Herisset, A. et a!. 1973. Differentiation of
several essential oils of similar composition.
VIII. Oils of Thymus species. Plantes Med.
Phytother. 7:34-47. IX. The gas chromato-
graphy of oil of thyme. Ibid. 7:114-120.
International Organization for Standardiza-
tion. 1985. Whole thyme (Thymus vulgaris
Linnaeus )-Specification. International-Stan-
dard; ISO 6754-1985.
Lawrence, B.M. 1985. A review of the world
production of essential oils. Perf. Flav. 10(5):
1-20.
Lawrence, B.M. 1982. Progress in essential oils.
Thyme oil. Perf. Flav. 7(2):35.
Lawrence, B.M. 1976-1978. Progress in essen-
tial oils. Thyme. (A monthly review). Perf.
Flav. 1(3):45, 2(1):5-6, 3(2):48-49.
Lawrence, B.M. 1981. Progress in essential oils.
Perf. Flav. 6(5):27.
Lawrence, B.M. 1984. Progress in essential oils.
Perf. Flav. 9(2):23.
Mateo, C., Morera, M.P., Sanz, J., and
Hernandez, A. 1979. Estudio analitico de
aceites esenciales procedentes de plantas
Espanolas 1. Especies del genero Thymus.
Rivista !tal. 60:621-627.
Razdan, T.K. and Koul, G.L. 1975. Composition
of wild thyme oil. Riechst. Aromen
Koerperpflegem. 25:166, 168. (German).
Richard, H., Benjilali, B., Banquour, N., and
Baritaux, 0. 1985. Study of various essential
oils from Moroccan thyme. Lebensm. -Wiss.
Techno!. 18(2):105-110.
Stahl-Biskup, E. 1986. Essential oil of
Norwegian thyme species, II. Thymus
336 Source Book of Flavors
pulegioides. Planta-Medica 52(3):233-235.
Wiesner, I. and Wiesner JR., I. 1980. Is it
possible to replace common thyme with local
species? Nase Liecive Rastliny 17(1):8-11.
Turmeric (Curcuma)
Turmeric is the dried cleaned rhizomes of
Curcuma tonga L., a member of the Ginger
family and native to China and the East
Indies.
Commercial Sources
Southern China, India (Madras, Aleppey),
Malaysia, Indonesia (Java), Sri Lanka,
Jamaica and Haiti.
Description
Deep yellow to orange-yellow roughly
cylindrical rhizomes; 2.5 to 8 em long and up
to 1.5 em thick. Some have tuburcle-like
protruberances; most have tapering ends.
The surface is rough with numerous annular
ridges. The texture is hard and breaks
cleanly to reveal an orange-colored, waxy
and resinous interior.
The color of powdered turmeric varies
from lemon-yellow (Madras) to orange-
yellow (Aleppey). In the United States, the
latter is preferred as it holds its color better
when the product is exposed to sunlight.
Sensory Character
Strongly penetrating, heavy, spicy odor;
the flavor is bitter but aromatic with some
pungency. The spice is used both for its
flavor and coloring attributes, particularly in
pickle processing.
Constituents
Turmeric contains three prime components:
(a) volatile oil, which is orange-yellow and
slightly fluorescent (1.5-6 percent); (b) a
yellow coloring matter, curcumin, which
is 1,7 bis (4-hydroxy-3-methyoxyphenyl)-1,
6-heptadien-3,5-dione, also known as
diferuloyl methane (0.2-0.5 percent) and
(c) starch.
Curcumin The pure compound is an
orange-yellow crystalline powder, insoluble
in water but soluble in alcohol and glacial
acetic acid. It is pH sensitive and becomes
reddish-brown in alkaline solution.
Turmeric Essential Oil Investigations
into the chemical composition of turmeric
oil are limited (Lawrence 1982). The oil
consists of a-phellandrene (1.0 percent),
sabinene (0.6 percent), 1, 8-cineole (1.0
percent), borneol (0.5 percent), zingiberene
(about 25 percent), f3-sesquiphellandrene,
ar-curcumene and bisabolene (about 6
percent), turmerone and dehydroturmerone
(about 58-60 percent), and some a- and
y-altanone.
HaCo~H-CH2-C-CH=C(CHa
I II CHa
CHa 0
turmerone
0
<:""'"CHa
HaC lH--<:!H2~~--<::H== 'cHa
CHa 0
dehydroturmerone
Oleoresin Turmeric
Obtained by the solvent extraction of finely
ground turmeric, the nature of the extract
ranges from a viscous oily fluid to a pasty
semisolid to a hard amorphous solid which
may be powdered, depending on the solvent
selected. , The prime oleoresin contains
15-25 percent volatile oil as well as the
coloring matter. As the essential oil is highly
aromatic and not required in many products
in which the oleoresin is used as a coloring
agent, many commercial oleoresins are
further processed to remove all or part of
the essential oil, so enhancing the coloring
power. The dispersion of oleoresin turmeric
in pickle brines and vinegar poses problems.
To overcome them, the oleoresin may be
mixed with a solubilizing agent (e.g.,

Polysorbate 80), which not only gives a
product that mixes with water to give a clear
solution but also provides a uniform free-
flowing oleoresin that is easy to handle.
Care must be taken in using such oleoresins;
in the United States, the FDA has placed a
tolerance of 0.05 percent of Polysorbate 80
in pickles 172.840 (c) (3), which must not be
exceeded. Oleoresin turmeric is generally
sold on color value.
Specification in EOA No. 271.
A deep red to orange-red viscous fluid
oleoresin, but may be semifluid and butter-
like to pasty, depending on the solvent used.
Most commercial oleoresins are mixed with
a diluent such as propylene glycol or are
solubilized by admixture with a polysorbate.
The color value of the product should be
stated on the label.
Color value of oleoresin turmeric: De-
termined spectrophotometrically in a 1:
200,000 solution in ethanol at the maximum
absorbance, about 422 nm. The arbitrary
color units are obtained by multiplying the
absorbance by 20,000 (or the equivalent
factor depending on the dilution used). The
method is described in the EOA specifica-
tion as well as in the publications of the
leading manufacturers of these products.
The color may also be expressed in terms of
curcumin content, also determined as
above:
. optical density 20
curcumm percent=--"-------='----
wt of sample (g) 1.6
The following oleoresins are available com-
mercially (Table 7-80).
TABLE 7-80. Commercially available
oleoresins
Curcumin Suggested
Color Value Content(%) Use Rate(%)
12.5-14.5
38-42
1000 units
54
86-97
Natural Flavoring Materials 337
References: Turmeric (Curcuma)
Banerjee, A., Kaul, V.K., and Nigam, S.S. 1982.
Antimicrobial activity of the essential oil of
Curcuma amada Roxb. Indian J. Microbia.
22(2):154-155.
Guenther, E. 1948-1952. The Essential Oils,
Vol. 1- VI. New York: D. Van Nostrand Co.
Lawrence, B.M. 1982. Progress in essential oils.
Perf. Flav. 7(1):45.
Viasan, A.C., Menon, A.N., Rao, J.M.,
Narayanan, C.S., and Mathew, A.G. 1989.
Chemical analysis of some cultivars of
Curcuma longa Linn. J. Food Sci. Techno/.
India 26(5):293-295.
Spice and Herb Mixes
Consists of parsley, celery leaves, onion and
a sprig of thyme. The combinations may be
varied for different dishes. For example, a
good bouquet garni for lamb stew might
include parsley, thyme and a clove. The
herbs and spices are tied together or sewn in
a small cheesecloth sack. Like a tea bag, the
sack and spices are discarded. In the whole
form, they lend themselves especially to
long-cooking dishes such as soups and
stews.
Chili Powder
A blend of spices, usually chili pepper,
cumin seed and oregano. Often other spices
are added. The premixed blend has gained
in popularity in the United States. It is a
basic seasoning in all Mexican-type dishes,
including the popular chili con carne. Chili
powder is used in eggs and omelettes,
shellfish and oyster cocktail sauces, gravy
and stew seasonings, ground meats,
hamburgers, frankfurters and other pre-
turmeric pared meats.
Curry Powder
Prepared by grinding a mixture of the fol-
lowing spices: cinnamon, cumin, cardamon,
5 coriander, turmeric, cloves, red pepper,
1.5 fenugreek, allspice, black pepper, ginger,
15-20 mustard and nutmeg. Some spices can be
omitted. Curry powder is used as flavoring
in sauces, meat, fish, and egg dishes.
338 Source Book of Flavors
Indian Curry A richly spiced sauce.
The uniform rule for cooking curry is that
the freshly ground spices first be heated in
fat to develop their characteristic flavor.
The "curry stone" on which spices are pul-
verized daily is a common kitchen tool in the
Indian home.
In Bombay the so-called wide-mouthed
curry is a delicious concoction of meats,
lentils, vegetables and nuts, in a sauce
seasoned with a dozen or more spices.
Foods in Bombay are quite highly spiced
and many red chillis are used. Generally,
people prefer a sharp taste, as hot seasoning
causes them to perspire more freely, which
is most welcome in the scorching heat of
their equatorial climate.
"Korma" is a dry curry sauce and
is applied to meats in the same way as
barbecue sauce. However, the meats in a
korma sauce are marinated in yogurt before
cooking. Often, the sauce is thickened by
the addition of desiccated coconut or poppy
seed.
"Kebab" curries are pieces of meat,
onions, ginger, garlic, etc., threaded on
short skewers, then fried and afterward put
in a spiced gravy to simmer for a while.
"Kofta" curries are meatballs con-
sisting of finely ground chicken or mutton,
then cooked in a curry sauce. "Vindaloo" is
a sour curry; the meats are marinated in
well-spiced vinegar for several hours before
they are cooked.
"Malai" curry is an Indian dish of
spiced prawns baked in a whole, almost
mature coconut until the coconut meat has
dissolved and mixed with the spices.
Fine Herbes
A household name for a combination of
three or more herbs. It usually includes
parsley, chives, chervil and other herbs,
such as sage, basil and savory. The herbs
are ground fine and carefully blended. They
are used in cheeses, fish, omelettes, butter
sauces for cooked vegetables and dressings
for cold salads.
Mixed Pickling Spice
A blend of 10 to 16 different whole spices
whose proportions are balanced to create a
distinctive flavor. Mixed pickling spice is
used primarily in pickling. Wrapped in a
cheesecloth bag, it is dipped in cooking
meats, soups, and vegetables, so that their
flavors are not drawn off as quickly as with
ground spices.
Pastry Spice
A blend of cinnamon, cloves, ginger,
allspice and nutmeg. It is used for flavoring
pastries, puddings, cakes, etc.
Pickling Spice
A mixture of cassia, allspice, coriander,
mustard seed, laurel leaves, cloves, ginger,
pepper, chili peppers and cardamom seed.
Pickling spice is used for pickling and pre-
serving vegetables.
Poultry Seasoning
A mixture of pepper, ginger, mace, allspice,
cloves, marjoram, nutmeg, thyme, savory
and sage. It is used with poultry, veal and
pork.
Pumpkin Pie Spice
A blend of cinnamon, cloves and ginger.
The whole spices are ground together rather
than mixing them after grinding. It is used to
flavor pumpkin pie, spiced cookies, ginger-
bread and breakfast buns.
Sausage Seasoning
A mixture of pepper, sage, ginger, nutmeg,
cloves or allspice, and sometimes red
pepper. It is used in delicatessen meats.
LICORICE (LIQUORICE)
In its natural form, licorice is the root and
subterranean stem of several species of
Glycyrrhiza but principally (G. glabra L.,
and also two varieties: var. glanulifera
(W. & K.) Regel and Herder and var.
violacea (Boiss). The principal species is
known as "Spanish licorice" and the

glandulifera variety as "Russian licorice."
The plant is a tall perennial distributed
throughout Europe, but cultivated in Sicily,
Spain, Syria, Turkey and the southern
parts of the former Soviet Union. The lico-
rice of commerce consists of the peeled or
unpeeled dried roots cut into short cylindri-
cal pieces; they are usually whole, but may
be split longitudinally if the root is very
thick. The roots are normally collected at
3-4 yearly intervals to allow for satisfactory
growth; after cleaning, they are dried slowly
prior to bundling.
Licorice root has a sweet taste with a
slight lingering bitterness. It is often asso-
ciated with the flavor of anise and vice
versa. It is generally used in the form of an
aqueous extract; the Russian root yields
25-30 percent of water-soluble extractive.
Licorice for use in the confectionery industry
and as a source of flavor is purchased in the
form of "block juice" (often referred to
merely as licorice). This is a black, brittle
extract obtained by boiling the comminuted
root with water, separating out the insoluble
matter either by settling or centrifugation
and evaporation to a 15-20 percent moisture
content. The product is usually cast into
large blocks (hence the name). Commercial
"block juice," whose composition depends
largely on source, contains a mixture of
sugars (about 16 percent), starches and
gums (30-40 percent) and an intensely
sweet glycoside, glycyrrhizin (12-20 per-
cent, although much higher figures have
been quoted depending on the test method
used). This latter constituent is about 50
times sweeter than sucrose and its level in
"block juice" may be used as a quantitative
indicator of quality, although other attri-
butes are important (e.g., insoluble matter,
ash, etc.); and, in particular, consistency of
flavoring effect.
"Block juice" may be further vacuum-
dried and offered as drum-dried granules or
flakes, or it may be ground or spray-dried to
a low moisture content (max 5 percent) to
give a free-flowing powder. Ammoniated
glycyrrhizin contains about 80 percent of
Natural Flavoring Materials 339
the glycoside and is finding increasing
popularity as a sweetening agent.
Licorice has a characteristic odor and
flavor apart from its intrinsic sweetness. The
volatile components have been investigated
by numerous groups. A tabulation of the
volatiles identified to date is presented by
Maarse and Vischer (1989).
References: Licorice (Liquorice)
Benetti, G. and Luise, M. 1985. Determination
of glycyrrhizic acid in liquorice-based con-
fectionery products by HPLC. Bollettino-dei-
Chimici-lgienisti 36(S2):81-85.
Frattini, C., Bicchi, C., Barettini, C., and Nano,
G.M. 1977. Volatile flavour components of
licorice. J. Agric. Food Chern. 25(6):1238-
1241.
Hiraga, Y., Endo, H., Takahashi, K., and
Shibata, S. 1984. High-performance liquid
chromatographic analysis of licorice extracts.
J. Chromatog. 292(2):451-453.
Hurst, W.J., McKim, J.M., and Martin, R.A. Jr.
1983. High-performance liquid chromato-
graphic determination of glycyrrhizin in
licorice products. J. Agric. Food Chern. 31(2):
387-389.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food. pp. 950-952.
Netherlands: Grafische Industrie Kreon,
Zeist.
Petitbois, D., Hamann, Y., Lesgards, G., and
Bozzi, R. 1985. Analytical study of liquorice
products. Choice of a chromatographic
system for determination of the content of
glycyrrhizic acid and comparison with the
traditional gravimetric method. Annales-des-
Falsifications, -de-l' Expertise-Chimique-
t-Toxicologique 78(834):19-31.
Vora, P.S. 1982. High pressure liquid chromato-
graphic determination of glycyrrhizic acid or
glycyrrhizic acid salts in various licorice
products: collaborative study. J. Assoc. Offic.
Anal. Chern. 65(3):572-574.
Yahara, S. and Nishioka, I. 1984. Flavonoid
glucosides from licorice. Phytochem 23(9):
2108-2109.
MUSHROOMS AND FUNGI
Edible mushrooms form a very large group
of nonpoisonous fungi that possess a delicate
 340 Source Book of Flavors
to strong flavor, some of which are so
unusual that their acceptance is an acquired
taste. Most of the edible mushrooms
develop quite different flavors when heated,
as in the preparation of cooked foods. From
the flavorist's viewpoint, two types are of
major interest:
Common field mushroom (Psalliota
campestris, P. hortensis, P. arvensis-
formerly classified in the genus Agaricus
L., and Agaricus bisporus (Lange)
lmbach.
Honeycomb mushroom (Boletus edulis
Bull.)
There are, however, numerous other flavor-
ful mushrooms, many of which are of only
regional popularity. Three such species are:
Padi straw mushroom (Volvariella volvacea)
Shiitake (Lenzites elodes)
Truffles (Tuber melanospermum)
Bianchini et al. (1976) describe in addition:
Morels (Morchella spp.), Caesars mush-
room (Amanita caesarea), parasol
mushroom (Repiota procera), Chanterelle
mushroom (Cantharellus tubaeformis) and
oyster mushroom (Plemotus osteatus), all of
which are used in culinary practice and have
interesting flavoring possibilities.
Sensory Character
There is far too wide a spectrum of flavor-
ing effects to be specific about a pro-
file that might be described as typically
"mushroom-like." The common field mush-
room, whether it is grown out of doors
or cultivated under precisely controlled
conditions, has only a slight intrinsic odor
and flavor. The immature "button" mush-
room has a somewhat nutty character, but
this is lost as the mushroom develops.
Cooking produces a quite different flavor
profile whose nature depends on the method
and degree of heat applied, as the aromatic
products are the result of a Maillard reac-
tion. The delicate and often specifically
characteristic odor and flavor of freshly
picked mushrooms cannot be recovered
by direct organic solvent extraction; are
entirely lost by dehydration; but may be
concentrated and isolated by first gently
warming the chopped mushrooms with
water followed by pentane extraction and
microdistillation. Such a process is not
commercially viable.
Mushroom extracts are available com-
mercially. These are usually prepared from
Boletus edulis caps of Polish or South
African origin.
Constituents
Fresh mushrooms contain sugars (about 7
percent), proteins (about 3.5 percent), fats
(about 0.4 percent), some volatile com-
pounds (5-15 ppm) and water (about 88 per
cent). These constituents have been inves-
tigated by numerous workers to establish
their nature and relative values nutritionally
and as a source of the characteristic mush-
room flavor. Mushroom aroma and flavor
are of two distinctly different types: (a)
intrinsic uncooked aroma and (b) the aroma
and flavor developed by drying and cooking.
Raw mushroom aroma and flavor are due to
the presence of very low concentrations
of numerous alcohols and carbonyl com-
pounds, whereas that of dried and cooked
mushrooms is mostly determined by the
nonenzymatic browning reaction of amino
acids and sugars present in the raw material
(Whitfield and Last 1991).
Substantial work has been done on
identifying the flavor constituents of mush-
room. To date, approximately 175 com-
pounds have been identified in fresh
mushrooms (Maarse and Visscher 1989).
The most characteristic flavor constituents
of the cultivated mushroom are the unsatu-
rated alcohols (primarily 1-octene-3-ol).
The shiitake mushroom is quite different
in sensory properties from the common
mushroom and is highly valued in China and
Japan. The fresh mushroom has little flavor

or aroma, but develops on drying or
crushing. The characteristic aroma is sulfury
in nature. A total of 63 compounds have
been identified in fresh, dried or cooked·
shiitake mushroom. The major compounds Chen, C.C. and Wu, C.M. 1984. Volatile com-
identified were 1-octene-3-ol (113 mg/kg), 3-
octanone (13 mg/kg), 2-octenol (7.5 mg/ml),
Hanssen, H.P. and Klingenberg, A. 1983.
octanol (4.6 mg/kg), 1,2,4,5-tertrathiane
(9.3mg/kg), lenthionine (8.7mg/kg) and
1,2,4-trithiolane (3.1 mg/kg), (Chen et al.
1984; Chen and Ho 1986). Lenthionine is
considered to contribute the characteristic Hong, J.S., Lee, K.R., Kim, Y.H., Kim, D.H.,
flavor to this mushroom.
Mushroom Extract
Mushroom extract (sometimes called
oleoresin) is prepared by making a dilute
alcoholic extraction of selected dried Boletus
edulis caps. The product is a dark-brown,
viscous paste, which is miscible with water
and blends readily with other spice
oleoresins. It is difficult to quote an equiv-
alent use rate to fresh or dehydrated mush-
rooms as the flavor profile is so very
different. The extract has a full rich and
meaty flavor with a characteristic mushroom-
like back-note.
References: Mushrooms and Fungi
Ahn, J.S. and Lee, K.H. 1986. Studies on
the volatile aroma components of edible
mushroom. Han'guk Yongyang Siklyong
Hakhoechi 15(3):258.
Auduin, P., Vidal, J.P., and Richard, H. 1989.
Volatile compounds in the aroma of some
wild edible mushrooms: morel (Morchella
conica), wood blewitt (Lepista nuda), clouded
agaric ( Clitocybe nebalaris), and false
chantarelle (Hygrophoropsis). Sci. Aliments.
9(1):185-193.
Charpentier, B.A., Sevenants, M.R., and
Sanders, R.A. 1986. Comparison of the effect
of extraction methods on the flavor volatile
composition of the shiitake mushrooms
(Lentinus edodes) via GC/Ms and GC!FfiR.
Dev. Food Sci. 12:413.
Chen, C.C., Chen, S.D., Chen, J.J., and Wu,
C.M. 1984. Effects of pH value on the for-
mation of volatiles of shiitake (Lentinus
edodes), an edible mushroom. J. Agric. Food
Chern. 32:999-1001.
Chen, C.C. and Ho, C.-T. 1986. Identification of
Natural Flavoring Materials 341
sulfurous compounds of shiitake mushroom
(Lentinus edodes Sing). J. Agric. Food Chern.
34:830-833.
ponents of mushroom (Agaricus subrufenens).
J. Food Sci. 49(9):1208.
Determination of some important flavour
compounds in commerical mushroom concen-
trates. Zeits. Lebensm. Unters. Forsch 177(5):
333-335.
Kim, M.K., Kim, Y.S., and Yeo, K.Y. 1988.
Volatile flavour compounds of Korean
shiitake mushroom (Lentinus edodes). Korean
J. Food Sci. Techno/. 20(4):606-612.
Horns, H. and Richter, J. 1987. Production of a
natural mushroom flavour concentrate.
German Federal Republic Patent Appli-
cation. DE 35 24 473 Al.
Kibler, L.A., Kratky, Z., and Tandy, J.S.
1988. Mushroom flavour. European-Patent-
Application. EP 0 288 773 A2.
Komai, T., Mizutani, S., Gocho, S., and Hatae,
S. 1986. Manufacture of mushroom flavor.
Japanese Patent. JP 61, 293, 367.
Maga, J.A. 1981. Mushroom flavour. J. Agric.
Food Chern. 29(1):1-4.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food. Zeist: TNO-CIVO Food
Analysis Institute.
Schindler, F. 1988. Preparation of a mushroom
flavour in fungal biomass. German-Federal-
Republic-Patent-Application. DE 37 08 932
A1 (DE3708932A1).
Tressl, R., Bahri, D., and Engel, K.H. 1982.
Formation of eight-carbon and ten-carbon
components in mushrooms (Agaricus
campestris). J. Agric. Food Chern. 30(1):89-
93.
Vidal, J.P., Toulemonde, B., and Richard, H.
1986. Aroma of volatiles of the fairy ring
mushroom (Marasmius oreades). Lebensm.-
Wiss. Techno/. 19(5)353-9.
Whitfield, F.B. and Last, J.H. 1991. Vegetables.
In Volatile Compounds in Foods and
Beverages. ed. H. Maarse, pp. 203-269. New
York: Marcel Dekker.
Wu, C.M., Wu, J.L.P., Chen, C.C., and Chou,
C.C. 1981. Flavor recovery from mushroom
blanching water. In The Quality of Foods
and Beverages. Chemistry and Technology.
Vol. 1., ed. G. Charalambous, pp. 133-145.
New York: Academic Press.
342 Source Book of Flavors

TABLE 7-81. Nut composition (g/100 g)

Total
Species Moisture Protein Fat carbohydrate Fiber Ash

Almonds (raw) 4.7 18.6 54.2 19.5 2.6 3.0

Almonds (roasted) 0.7 18.6 57.7 19.5 2.6 3.5
Brazil nuts (raw) 4.6 14.3 66.9 10.9 3.1 3.3
Chestnuts (raw) 8.4 6.7 4.1 78.6 2.5 2.2
Coconut (fresh) 50.9 3.5 35.3 9.4 4.0 0.9
Coconut (dry) 3.5 7.2 64.9 23.0 3.9 1.4
Filberts (raw) 5.8 12.6 62.4 16.7 3.0 2.5
Macadamia nuts (raw) 3.0 7.8 71.6 15.9 2.5 1.7
Peanuts (raw) 5.6 26.0 47.5 18.6 2.4 2.3
Peanuts (roasted) 1.8 26.2 48.7 20.6 2.7 2.7
Pecan (raw) 3.4 9.2 71.2 14.6 2.3 1.6
Pine nuts (raw) 5.6 31.1 47.4 11.6 0.9 4.3
Pistachio nuts (raw) 5.3 19.3 53.7 19.0 1.9 2.7
Walnuts (raw) 3.1 20.5 59.3 14.8 1.7 2.3

NUTS Asia Minor and now cultivated throughout

A nut is any seed or fruit consisting of a
kernel, usually oily, surrounded by a hard
brittle shell. Many so-called nuts are
botanically not true nuts; e.g., coconut
(drupe), peanut (legume), Brazil nut
(capsule), etc. As a source of natural
flavors, nuts are generally incorporated
directly into an end product either whole,
chopped or grated as appropriate.
The Encyclopaedia Britannica lists 169
different species of nuts of commercial
value, but of these only about 10 are of
direct interest to the flavorist or food pro-
cessor. Apart from domestic consumption,
the following nuts are of importance in
baked goods and confectionery, both as a
source of flavor and for their pleasing
the Mediterranean region. Two varieties
are recognized: sweet (var. dulcis (DC.)
Koehne) and bitter (var. amara (DC.)
Focke). Almonds are a source of a bland
fixed oil, which is official in many
pharmacopoeias. Sweet almonds are used
extensively in confectionery and in some
baked goods (see Maga 1991 for a discussion
of the flavor of sweet almonds). Bitter
almonds are distinguished by containing a
cyanogenetic glucoside-amygdalin (2-4
percent), which is broken down by the
enzyme, emulsion, to yield benzaldehye,
hydrocyanic (prussic) acid and D-glucose.
V
H

textural effects (Table 7-81). The problems
associated with purchasing, handling and
the use of these ingredients has been de-
scribed by Minifie (1979), Lees and Jackson
(1973) and Maga (1991). The high level of
fat in most nuts makes them prone to oxida-
tion and thus off-flavor development (Table
7-81). The flavor properties of nuts have
been discussed by Maga (1991).
Almond
Almonds are the fruits of a deciduous tree
(Prunus amygdalus Batsch.), a native of
~ {}C,.H,O" + 2H,O-
!N
0 CHO + HCN + 2C,H 12Q 6
glucose
Commercial Sources
Spain, Portugal, France, Italy, Morocco,
Algeria, United States (California),
Australia, South Africa and China.
The almond of commerce is the pit of a
peach-like fruit containing a single seed.
The kernel contains about 54 percent fixed
oil and some 18 percent protein. The de-
oiled press-cake of bitter almonds yields
0.5-0.7 percent volatile oil.

Oil ofBitter Almond
Obtained by the distillation of the expressed
kernels of dried bitter almonds, also of
peach (Prunus persica L.) and apricot (P.
armenica L.). The de-oiled press-cake is dis-
integrated and macerated for 12 hrs. in
warm water (50-60°C) to activate the
enzymatic reaction, as the volatile oil does
not exist as such in the dried kernels. The
resulting prime oil may contain 2-5 percent
hydrocyanic acid, which must be removed
chemically before the product is redistilled
to give oil of almond FFPA (Free From
Prussic Acid).
Specification in
EOA No 215, FCC III (1981).
A colorless to pale yellow oil; specific
gravity (25°/25°C), 1.040 to 1.050; optical
rotation, zero to a max of 0.15°; refractive
index (20°C), 1.5410 to 1.5460; solubility (70
percent ethanol), 2 vol; acid value, max
8; aldehydes (as benzaldehyde), min 95
percent.
Constituents
Oil of bitter almond consists primarily of
benzaldehyde with traces of other com-
pounds that distinguish it from synthetic
benzaldehyde.
Brazil Nut
The source of Brazil nuts is a magnificent
tree that grows to about 150ft. (Bertholletia
excelsa) and bears large woody fruits which
fall at maturity, splitting to reveal 20-24
closely packed, kidney-shaped seeds with
woody wrinkled shells. These seeds are the
Brazil nuts of commerce also known as Para
nuts, castana and butternuts.
Commerical Sources
Brazil (Manaos, Para), Bolivia. Shelled
Brazil nuts contain about 65 percent fat and
17 percent protein. They are very popular
in chocolate confectionery, both whole and
chopped.
Natural Flavoring Materials 343
Flavor Properties
Maga (1991) has discussed the sensory and
analytical data available on the flavor of
Brazil nuts.
Cashew Nut
The "Pear Cashew" is an evergreen tree
(Anacardium occidentale), native to Brazil
but now cultivated in India and the West
Indies. The tree bears an overgrown pear-
shaped fruit stalk (cashew apple) to which
are attached the kidney-shaped nuts, each
having a tough skin containing a vesicant
fluid. The fruits are harvested, roasted to
destroy the irritant compound, and then
cracked open and freed from the shell.
Cashews come in different sizes and grades;
in splits, where the whole nut is split apart;
in butts, where the tip is broken off; and
in various large and small broken pieces.
Unroasted cashew nuts have a bland flavor,
but when roasted they develop a mildly
sweet character, making them a popular
dessert nut when lightly salted.
Commercial Sources
Brazil, Southern India, Sri Lanka and East
Africa.
Cashew nuts have soft, whitish, mealy
texture and contain about 44 percent fat,
20 percent protein and about 27 percent
carbohydrate.
Chestnut
Although very popular when roasted,
chestnuts, the fruits of a large tree (Castanea
sativa or one of the many species and
varieties of this genus) are not of much
value as a source of flavor. Chestnut stuffing
is traditional with turkey and a C<'nfectionery
delicacy "marons glaces" is made by
heating chestnuts in sugar of increasing
concentration.
Chestnuts are unique among the nuts in
being low in fat (8 percent) and high in
carbohydrate (78 percent). There is virtually
 344 Source Book of Flavors

no literature on the flavor properties of eye appeal. Thread coconut is used where
chestnuts. medium or short shred coconut is not
enough to meet requirements.
Coconut Creamed coconut or plastic coconut is an
emulsified coconut meat containing the
The coconut (Cocos nucifera) is a graceful solids and oils of fresh coconuts. It can be
tropical palm that flourishes throughout the used to replace coconut oil, as a fat for
sandy coastal regions of the tropics and sub- icings for coating candies, in butterscotch,
tropics. This plant provides many useful caramels, in hard candy filled center chips '
products, but most importantly the fruit, the and nougats.
coconut.
Dried coconut kernels freed from the Flavor Constituents
shell and dried, become the "copra" of It is generally agreed that fresh coconuts
commerce. On pressing, this yields 60-65 obtain their characteristic flavor from o-
percent coconut oil. The most important lactones (Maga 1991). o-Octalactone
product used in confectionery is desiccated (33ppm), o-decalactone (82ppm) and o-
coconut available in three grades-fine, dodecalactone (23 ppm) are considered
medium and coarse. Other products of to be the most important of the lactones
interest to the flavor technologist include: (Saittagaroon et al. 1984).
canned coconut in a light sugar syrup,
sweetened coconut and tenderized coconut.
Cola Nut
Coconut in Confectionery Products See Kola nut.
Coconut is used in freshly ground, sweetened
and unsweetened, dry, toasted, and creamed
Hazelnut
forms. Freshly ground coconut imparts the
best flavor and tenderness to candies. It Hazelnuts or filberts are the fruits of a low
contains from 40 to 50 percent moisture and shrub (Corylus ave/lana, C. maxima or of
should be cooked before adding it to cream several other regionally growing species of
candies. Often, fresh c:oconut is replaced this genus). The kernels are roundish or
by a desiccated or dry coconut. The two oblong and vary considerably in size. They
types of desiccated or dry coconut are have a delicate flavor and a pleasant crisp-
unsweetened and sweetened. Sweetened ness, which makes them a popular ingredient
coconut has a little more crispness than in chocolate confectionery, nougat, etc. The
unsweetened coconut. nuts imported into the United States are
Macaroon is a finely comminuted coconut smaller in size than the ones grown out of
that is used in toasted coconut macaroons, the country.
fudge and other candies that require a fine
texture. Fine coconut is often combined Commercial Sources
with freshly ground or coarser coconut Spain, Italy, France, Turkey, United States
to stiffen the mass and to keep the liquid (California), China and Japan.
portion of the candy batch evenly distrib-
uted. Medium-sized and colored coconut is Hazelnuts in Confectionery
most often used for decorative purposes. For full flavor, filberts should be lightly
Coarse coconut is used in coconut slugs. It roasted before being added to candies.
can also be colored and used as a topping. Filbert paste is a combination of sugar and
Slice of chip coconut is used as a topping for nuts, and is mixed with fondant as a center
fudge and in coconut brittles. Short shred for bonbons. It is combined with chocolate
coconut is used in candies that call for and coconut oil to add fine flavor and

texture to truffle-style confections. Filberts
mixed with cashews give a delicate nutty
flavor to many types of candy.
Flavor Constituents
There has been substantial work on the
flavor of hazelnuts (Maga 1991). How-
ever despite the identification of 305 com-
pounds, the constituents responsible for
hazelnut flavor have not been characterized
(Emberger 1985).
Kola Nut
The kola nuts (or cola nuts) of commerce
are the dried cotyledons of a tropical fruit
borne by a large tree (Cola nitida (A.)
Chev. or C. acuminata Schott and Endl.),
which grows ~ld in the forests of Sierra
Leone, northern Ghana and near the source
of the Niger. They are also cultivated in
parts of West Africa, Brazil and Indonesia
(Java). Of the two species, the larger nitida
nuts from the Ivory Coast are more valued
than the smaller acuminata nuts from
Angola, Gabon and Zaria.
The reddish-brown nuts are 2-5 em long
and about 1-3 em broad, roughly plano-
convex in shape but very variable. The
texture is hard and solid, the nuts breaking
cleanly. The odor is slight and the taste
mildly bitter and astringent.
Constituents
Kola nuts contain 1.5-2.5 percent of
caffeine, together with traces of theobro-
mine, a red dye (kola red), some fats,
carbohydrates and tannin.
Products
Kola nuts are used primarily for the pro-
duction of cola-type beverages, which
dominate the soft-drink niarket (at least in
the United States). For this application, the
kola nuts are finely ground and extracted
with 60 percent alcohol to make either a
tincture or a soft extract.
Natural Flavoring Materials 345
Pecan Nut
Pecan, a large tree of the walnut family
( Carya illinoensis Koch.) is native to North
America and grows extensively in Texas and
Oklahoma. The fruit is enclosed in a hard
fibrous husk, which splits open when ripe to
release four smooth, brown, cylindrical nuts
having pointed ends. The edible kernel has
a mildly characteristic flavor.
Commercial Sources
United States, Mexico.
The United States Government has set
standards for pecans and grades them for
foreign material, broken kernels, small
particles and dust, curing, cleanliness,
rancidity, decayed nuts, worm injury,
shriveled nuts and color.
Pistachio Nut
Pistachio is a small tree (Pistacio vera L.),
which is native to the Levant and is now
grown in Israel, Iran, Iraq, parts of India
and the former Soviet Union. Pistachio nuts
of commerce are the small whitish, thin-
shelled seeds whose kernels are pale green
in color and have a fine texture. They are
probably more widely used for their appear-
ance in nougat and other confectionery
products than for their rather delicate
flavor. The kernels are high in fat (about 55
percent).
Walnut
The walnut is a large tree (Juglans regia L.)
that is native to the region around the
Caspian Sea. It is now grown in many
countries, with some 25 useful species and
local varieties being recognized. Three
are of commercial interest: Black walnut
(Juglans nigra L.), the nuts of which are
ovoid, very rough, deeply ridged and have a
dark brown to black shell; English (Persian)
walnut (J. regia L.), having very light brown
nuts whose shells are easily broken; and
Butternut (J. cinereaL.), which has oblong,
cylindrical, thick-shelled nuts that are
346 Source Book of Flavors
sharply pointed at one end and bluntly
rounded at the base.
Commercial Sources
France (Bordeaux), Italy (Naples), United
States (California), China, South Africa,
Australia and Romania.
The walnut is contained in a green fleshy
husk from which it separates when ripe.
Walnuts are gathered, quickly washed,
cured and either slowly sun-dried or
artificially dried at 40°C to prevent their
splitting. In some regions, the nuts are
bleached to improve their appearance. The
English walnut is used extensively in con-
fectionery and bakery goods as well as a
dessert nut. Black walnuts from the eastern
United States are stronger in flavor and
are used in the manufacture of hard candy
brittles.
References: Nuts
Bonaga, G. and Giumanini, A.G. 1986. The
volatile fraction of chestnut honey. J. Agic.
Res. 25(2):113-120.
Butzenlechner, M., Rossmann, A., and Schmidt,
H.L. 1989. Assignment of bitter almond oil to
natural and synthetic sources by stable isotope
ratio analysis. J. Agric. Food Chern. 37(2):
410-412.
Delfini, C. and Stefano, R., di. 1984.
Benzaldehyde, an aroma compound re-
sponsible for the bitter almond aroma in
wines. Vignevini 11(7/8):9-10.
Eberhardt, R., Woidich, H., and Pfannhauser,
W. 1981. Analysis of natural and artificial
coconut flavoring in beverages. In Flavour '81
Weurman Symp., 3rd. ed. P. Schreier,
pp. 377-383. Berlin: Walter de Gruyter.
Emberger, R. 1985. An analytical approach to
flavor research. Cereal Foods World 30:691-
694.
Frank, H.K., Betancourt, L., and Uboldi, M.
1980. [The Brazil nut. II. Spoilage and con-
ditions for aflatoxin formation.] Die Paranuss.
II. Verderb und Bildungsbedingungen fuer
Aflatoxin. Deutsche-Lebens. Rund. 76(2):
47-50.
Frank, H.K. and Betancourt, L. 1979. [The
Brazil nut. I. Origin, production and chemical
and physical characteristics.] Die Paranuss.
I. Herkunft, Gewinnung, chemische und
physikalische Eigenschaften. Deutsche-
Lebens. Rund. 76(1):7-11.
Garrone, W., Antonucci, M., Bona, U., and
Clementi, S. 1988. Determination of hazelnut
content by means of their protein fraction
in chocolate bars, chocolates and milk con-
taining spreads. Lebens. Wissen. Techno/.
21(2):76-82.
International-Standard; ISO 6477: 1988. Cashew
kernels. Specification. International Organ-
ization for Standardization.
Jayalekshmy, A. and Narayanan, C.S. 1989.
Flavor constituents of roasted cashew nuts.
In Thermal Generation of Aromas ACS-
Symposium-Series; 409's eds. T.H. Parliment,
R.J. McGorrin, and C.-T. Ho, pp. 355-365.
Washington, D.C.: American Chemical
Society.
Kellard, B., Busfield, D.M., and Kinderlerer,
J.L. 1985. Volatile off-flavor compounds in
desiccated coconut. J. Food Sci. Agric. 36(5):
415.
Krueger, D.A. 1987. Determination of
adulterated natural bitter almond oil by
carbon isotopes. J. Assoc. Offic. Anal. Chern.
70(1):175-176.
Lees, R. and Jackson, E.B. 1973. Sugar Con-
fectionery and Chocolate Production. London:
Leonard Hill Books Ltd.
Maga, J.A. 1991. Nuts. In Volatile Components
in Foods and Beverages, eds. H. Marrse,
pp. 671-688. New York: Marcel Dekker, Inc.
Minifie, B.W. 1979. Chocolate, Cocoa and Con-
fectionery: Science and Technology, 2nd
Edition. Westport, Conn.: AVI Publishing
Co.
Ogutuga, D.B.A. 1975. Chemical composition
and potential commercial uses of kola nut,
Cola nitida, Vent. (Schott and Endlicher).
Ghana J. Agric. Sci. 8(2):121-125.
Pfannhauser, W., Eberhardt, R., and Woidich,
H. 1982. Aroma analysis in food chemistry by
GC/MS techniques: determination of natural
and artificial coconut flavor. Mikrochim.
Acta. 1(3-4):159.
Rikhter, A.A. 1980, pub!. 1981. Oxidation of
almond and walnut oils. Appl. Biochem.
Microbio. 16(4):446-450.
Saittagaroon, S., Kawakishi, S., and Namiki, M.
1984. Aroma constituents of roasted coconut.
Agric. Bioi. Chern. 48:2301-2307.
Senter, S.D., Horvat, R.J., and Forbus, W.R.

1982. GLC-MS analysis of fatty acids from
five black walnut cultivars. J. Food Sci. 47(5):
1753-1755.
Soliman, M.M.A., Osman, F., and El-Sawy,
A.A. 1981. Volatile components of roasted
pistachio-nut. Agric. Bio. Chern. 45(9):2123-
2125.
Torcol, J.V. and Dessolin, D.J. 1974. Kola nut
extraction, United States Patent. 3:818-110.
Woodroof, J.G. 1979. Coconuts: Products, Pro-
cessing, Products, 2nd Edition. Westport,
Conn.: A VI Publishing Co.
Yim, H., Kim, C.O., Shin, D.W., and Suh, K.B.
1980. Study on the storage of chestnut.
Korean J. Food Sci. Techno/12(3):170-175.
RESINS
Natural resins are exudations from trees or
other plants being formed naturally or as
the result of induced injury to the surface
tissues. As collected, many of these pro-
ducts are heterogeneous and may contain
impurities such as pieces of bark, wood,
etc., and, hence, require further processing
before they are suitable for use in flavoring
or fragrance compositions. The balsamic
resins and the oleo-gum-resins are of con-
siderable value in both flavoring and
fragrance compounding, for both their
fixative and aromatic properties. They act
as excellent blenders for other aromatic
effects, giving to the formulation a round-
ness and fullness of character. Numerous
refined and homogeneous products are
available, most of them marketed under the
manufacturer's trade name.
Balsam of Peru
See Peru Balsam under this classification.
Balsam of Tolu
See Tolu Balsum under this classification.
Benzoin
Benzoin is a balsamic resinous exudation
from the incised stem of Styrax benzoin
Natural Flavoring Materials 347
Dryand and other species of the Styrax
genus trees, which are native to Thailand
and Indonesia (Sumatra).
Commercial Varieties
Siam Benzoin
Yellowish-brown to white brittle tears
obtained from S. tonkinesis Craib.
Sumatra Benzoin
Hard brittle masses of whitish to reddish
tears embedded in a grayish-brown to
reddish-brown matrix. The source is S.
paralleloneurus Brans.
Penang (Glassy) Benzoin
Poor grades having little or no aromatic
value.
Palambang Benzoin
Poor grades having little or no aromatic
value.
Benzoin contains free benzoic and
cinnamic acids as well as their esters. The
chief alcohols present are benzoresinol and
coniferyl alcohol.
Chicle Gum
Chicle is the thickened latex of Achras
saporata L., a tree native to Mexico, South
and Central America; also from Minusops
globusa L. or M. balata Gartn. from Africa
and the West Indies.
Commercial Sources
Mexico (Yucatan), British Honduras.
The milky sap is collected by spiral
incision of the trees in a manner similar to
that used for rubber collection. The ac-
cumulated sap is bulked and evaporated to a
pasty consistency and may then be dried.
Chicle is the base for chewing gum, and its
use has been described in the literature
covering this subject.
348 Source Book of Flavors
Copaiba Balsam
Copaiba is the oleo-resinous exudation
obtained by incision of the trunk of Copaifera
lansdorfi Desf. and other Copaifera species
found in the Amazon basin and in the
northern parts of South America.
Commercial Varieties
These are usually distinguished by the name
of the town from which they are exported,
and differ considerably in appearance and
aromatic quality:
Para Copaiba
Thin, transparent, yellowish liquid with a
high volatile oil content.
Maracaibo Copaiba
Viscous, brownish-yellow, translucent fluid,
slightly fluorescent.
Maranham Copaiba
Viscous, brownish-yellow, translucent fluid,
slightly fluorescent.
The principal commercial sources are
Brazil, Venezuela and Colombia.
Kino
Kino consists of the dried juice obtained
from the incised trunk of Pterocarpus
marsupium Roxb., a tree which grows in
southern India (Malabar, Cochin) and Sri
Lanka. There are many other varieties of
kino, including: eucalyptus kino, Australian,
Botany Bay, African, West Indian, Caracas
and Myristica kinos.
The juice is collected and boiled down
to yield a dark ruby-red to reddish-brown
brittle mass, which is broken into irregular
pieces and may be dried and powdered.
Kino contains 70-80 percent kinotannic acid
together with catechol (pyrocatechin), pro-
tocatechuic acid, gallic acid and some gum.
Labdanum
Labdanum is an oleo-resinous secretion
from the leaves of several species of Cistus,
but mainly C. creticus L. and C. labaniferus
L., plants that are of the rock-rose family.
These are widely distributed over the rocky
ground of Greece, Cyprus, Crete, southern
France, Spain, Portugal and North Africa.
The gummy exudate of the hairy leaves
is either collected directly, using a special
leather rake and purified to remove
adhering sand, etc.; or alternatively, the
leaves are collected and solvent extracted.
Myrrh
Myrrh is the oleo-gum-resin obtained from
the trunks of Commiphora molmol Engl. or
C. myrrha Holmes., small trees or shrubs
which grow in Arabia, Ethiopia and Somalia.
Myrrh occurs as reddish-brown to
reddish-yellow rounded or irregular tears or
in agglomerations having an agreeable
aromatic odor and a bitter, acrid taste. It is
comprised of 25-40 percent resin, 55-60
percent gum and 2.5-8 percent volatile
oil. The oil contains eugenol, m-cresol,
cuminaldehyde, formic and acetic esters of
myrrholic acid and the sesquiterpene,
heerabolene.
Oakmoss Resin
Oakmoss resin is obtained by the solvent
extraction of Euernia pruna.stri Ach. or
E. furfuraceae Ach., which are lichens
found growing on oak, spruce and some
other trees in the forests of France,
Czechoslovakia and Italy. It is available as
either a "concrete" or an "absolute."
Olibanum (Frankincense)
Olibanum is a gum resin obtained from the
incised bark of Boswellia carterii Bindw. and
some other species of this genus. It occurs as
colorless to yellow, round to ovoid tears
having a distinctly balsamic and character-
istic odor. Two commercial qualities are
known-one is from Aden and the other
from Eritrea. The Aden is typically used for
perfumes.
 Natural Flavoring Materials 349

Composition Peyron, L., Acchiardi, J., Bignotti, D., and

Olibanum contains a gum similar to gum Pellerin, P. 1980. Comparisons des extraits
acacia (27-35 percent), resin (60-70 odorants d'encens obtenus par des tech-
percent) and an essential oil (4-7 percent) nologies diverses a partin de gommes
(Dorr 1973). The flavor constituents of d'origines geographiques differentes. Paper
No. 95, International Congress of Essential
olibanum have been reviewed by Lawrence
Oils, Cannes.
(1982). The data presented below are a
comparison of Aden and Eritrean gums
published by Oberman (1977). Oberman Opoponax
(1978) and Peyron (1980) have identified
Opoponax is a gum-resinous exudate of
additional components in olibanum.
Commiphora erythraea var. glabre.scens
Engl., a plant that grows in the desert region
Aden
of Ethiopia and Somalia. It occurs as
a-pinene (43.0%)
yellowish-brown lumps having a pleasantly
~-pinene (1.5%)
fragrant and characteristic odor with a flavor
sabinene (1.0%)
somewhat reminiscent of celery or lovage.
o-cymene (0.5%)
limonene (6.0%)
Opoponax Oil
1,8-cineole (1.0%)
Opoponax oil (sometimes known as oil of
camphene (2.0%)
Bisabolol-Myrrh) is manufactured by
p-campholenic aldehyde (1.5% )-cymene
steam distilling the sun-dried natural oleo-
(7.5%)
gum-resin opoponax. It is sweet-smelling,
verbenone (6.5%)
balsamic and somewhat spicy in character
octyl acetate (1.5%)
(Lawrence 1983). It is used to some extent
in perfume bases.
Eritrean
The following constituents have been
a-pinene (4.6%)
identified:
camphene ( 1.1%)
methoxy toluene +
o-elemene
hexyl acetate (1.5%)
a-cubebene
limonene + 1,8-ceneole (5.8%)
a-copaene
octanol (8.0%)
cis-a-bergamotene
linalool (2.5%)
~-elemene
octyl acetate (52.0%)
a-santalene
bornyl acetate (1.0%)
trans-a-bergamotene
cembrene A (2.3%)
caryphyllene
incensole (2.4%)
epi-~-santalene
incensyl acetate (3.4%)
a-humulene
y-muurolene
References
cis-a-bisabolene
Dorr, A. 1973. Frankincense, Myrrh and
~-bisabaolene
Opopanax. Dragoco Rept. 5:100-102.
Lawrence, B.M. 1982. Progress in essential oils. ar-curcumene
Perf. Flavor. 7:45-49. o-cadinene
Obermann, H. 1977. Differences in the chemistry y-cadinene
and odor of incense resins. Dragoco Rept.
11/12:260-265.
Obermann, H. 1978. Monoterpene acids as trace Maradufu (1982) used a combination
components in olibanum oil. Dragoco Rept. of techniques to identify the following
25(3):55-60. compounds in a hexane extract of C.
350 Source Book of Flavors
erythraea gum: furanodienone (1E, 4E,
-8, 12-epoxygermacra 1(10), 4, 7, 11-
tetraen-6-one), 2-acetoxyfuranondienone
(2-0-acetyl-8-, 12-epoxygermacra 1(10),
4, 7, 11-tetraen-6-one and 2-methoxyfur-
anondienone (2-0-methyll-8-, 12-wpoxyger-
macra 1(10), 4, 7, 11-tetraen-6-one.
a-Santalene and cis-a-bisabolene were
determined to be the major constituents of
the oil.
References
Lawrence, B.A. 1983. Progress in essential oils.
Opoponax oil. Perf Flav. 8(5):19.
Wenninger, J.A. and Yates, R.L. 1969. Con-
stituents of Opoponax oil: Sesquiterpene
hydrocarbons. J. Assoc. Offic. Anal. Chern.
52:1155-1161.
Peru Balsam
Balsam of Peru is a pathological product
obtained from the trunk of a large tree
(Myroxylon pereirae Royle, Klotzsch),
which grows in the lush forests of San
Salvador. The exudate is obtained by
removing a part of the outer bark, leaving
the inner bark exposed. The fluid balsam
begins to flow after about five days, is col-
lected and bulked. Further exudation is
induced by burning the wounded tissue; this
product is similarly collected and kept
separate. The wood is finally boiled to
recover a further grade of balsam. The com-
mercial product is a mixture of the various
collections and consists of a dark brown to
reddish-brown viscous liquid having an
agreeable balsamic odor and a persistent
bitter, acrid taste with some burning in the
throat.
Composition
Balsam Peru contains 53-60 percent of a
colorless oily liquid component and about
28 percent resin. The fluid fraction contains
benzyl benzoate and benzyl cinnamate and
has a markedly vanilla-like character.
Storax
Storax is a balsamic exudate induced by
bruising and wounding the bark of a tree
( Liquidamber orienta/is Mill.) found in the
forests of southwest Asiatic Turkey. The
crude balsam is grayish-brown in color and
is an opaque viscous liquid. It is usually
purified before use by solution in alcohol,
filtration, and removal of the solvent under
vacuum. The prepared material is a brown
viscous liquid having an agreeable balsamic
odor and flavor.
ToluBalsam
Balsam of Tolu is a solid or semisolid
resin obtained from the incised bark of
Myroxylon balsamum (L.) Harms., an ever-
green tree indigenous to northern South
America. The principal sources are
Colombia and Venezuela. It occurs as a soft
brownish-yellow to brown resinous solid,
which hardens on storage. It has an
aromatic, vanilla-like odor and flavor.
Balsam Tolu contains 12-15 percent
free cinnamic acid and about 8 percent free
benzoic acid together with about 8 percent
of an oily liquid component comprising
mainly benzyl benzoate and benzyl cinna-
mate. The balsam yields 2-3 percent of a
very fragrant essential oil.
References
Cherukuri, S.R., Wei, Y.C., Hriscisce, F., and
Sieke, A. 1986. Non-staling, substantially
moistureless chewing gum compositions and
improved method of preparation. United
States Patent 4 581 234.
Felton, S.M. and Kapp, I.B. 1976. Beverage
clouding agents based on natural gum resins.
United-States-Patent 3 959 510.
Lawrence, B.M. 1984. Progress in essential oils.
Perfum. Flavor. 9(1):49-60.
Lawrence, B.M. 1980. Progress in essential oils.
Perf. Flavor. 5(4):29-35.
Lawrence, B.M. 1983. Progress in essential oils.
Perfum. Flavor. 8(5):19-28.
Lawrence, B.M. 1982. Progress in essential oils.
Perf. Flavor. 7(1):45-50.
Opdyke, D.L.J. 1973. Monographs on fragrance

raw materials. Food Cosmet. Toxicol. 11(6):
1011-1077.
Opdyke, D.L.J. 1976. Monographs on fragrance
raw materials. Food Cosmet. Toxicol. 14(4):
307-338.
Riedel, H.R. 1983. Use of gums in confectionery.
Confectionery-Product 49(12):612-613.
Riedel, R. 1982. [Use of gums in confectionery
manufacture.] Wie in der Zuckerwaren-
Fabrikation der Rohstoff Gummi eingesetzt
wird. Kakao-und-Zucker 34(6):117-118.
Sato, Y., Takiguchi, T., Suzuki, S., and Suzuki,
Y. 1988. Studies on the release of !-menthol
from gum base and mechanical properties.
J. Japan. Soc. Food Sci. Techno/. [Nippon-
Shokuhin-Kogyo-Gakkaishi]. 35(2): 105-110.
Tezuka, S., Yamano, T., and Shitou, T. 1980.
Studies on natural gum resins for chewing
gum. J. Japan. Soc. Food Sci. Techno/.
[Nippon-Shokuhin-Kogyo-Gakkaishi]. 27(9):
419-425.
Unilever NV. 1980. Clouding agent. British
Patent 1 569 292.
Wei, Y.C., Cherukuri, S.R., Hriscisce, F.,
Piccolo, D.J., and Bilka, K.P. 1986.
Elastomer encapsulation of flavors and
sweeteners, long-lasting flavored chewing
gum compositions based thereon and process
of preparation. United States Patent 4 590
075.
Yakimischak, D. 1983. Chewing gum flavor
combination. United States Patent 4 385 071.
VANILLA
It took more than three centuries after
Cortez' discovery of vanilla, and its intro-
duction to commerce, to learn how to grow
it outside Mexico. It was as though the spirit
of Montezuma had rendered it infertile in
the hands of white men.
Vanilla is the fruit of an orchid. The
Totonaco Indians of Mexico, the fore-
runners of the present owners of vanilla
plantations, watched strangers take cuttings
of their vanilla, and joked about their
efforts to grow it elsewhere. It was planted
in Java and India under the same conditions
as grown in Mexico, yet it would not yield
beans.
Those who observed the cultivation pro-
cedure of the Mexican Indians recorded that
Natural Flavoring Materials 351
vanilla requires a warm and moist climate,
averaging from 23.9-29.4°C (75°-85°F) the
year around. It also requires a clay soil rich
in humus, with a mixture of shade and sun-
shine, shade predominating. The land must
be gently sloping-neither too flat nor too
steep. With this information, attempts were
made all over the world to naturalize it in
countries with similar climatic conditions,
yet these were not the only essentials of its
fertility.
It was not until 1836 that botanist Charles
Morren discovered the secret of vanilla's
reluctance to bear fruit outside of Mexico.
The reason is that the anatomy of the
flowers is such that self-pollination is im-
possible. Noting the short blooming period
of the vanilla orchid, Morren discovered
that a tiny bee of the Melipone variety
seemed to inhabit the producing regions of
Mexico. By studying the flower from the
standpoint of pollination, he noticed the
difficulties that any other insect would
have in achieving fertilization. Proposing
artificial pollination for the blossoms, he
became the first to produce vanilla pods
outside Mexico. He thus laid the founda-
tions for a new French industry, which has
paid many, many times more than the
plunder derived by Cortez' conquest of
Mexico, and broke Mexico's monopoly of
the lucrative vanilla trade.
Five years after this discovery, a former
slave, Edmond Albins, who was employed
on a vanilla plantation on the Island of
Reunion in the Indian Ocean, discovered a
practical method of manual pollination that
is used to this day. It is now accomplished by
hand; the left hand holds the flower, the
right a short wooden needle. If fruit is to be
formed, it must be carried out the moment
the flower unfolds and is undertaken daily
and repeated yearly before the harvest.
Using this process, the French soon
started vanilla cultivation on many of their
islands in the Indian Ocean, East and West
Indies, and French Oceania. The most
important producing area is the northern
part of the east coast of Madagascar. French
 352 Source Book of Flavors
vanilla beans are known as "Bourbon"
vanilla, since cultivation first started on
the Island of Reunion, east of Madagascar,
known at that time as the Island of Bourbon.
With Nossi-Be, near the northwestern tip
of Madagascar, and the nearby Comoro
Islands, they are the three important French
island territories producing vanilla. The
French contribute about three-fourths of the
world's vanilla beans. Following Morren's
discovery and in view of the increased
demand, Mexico, instead of depending
upon the bee as formerly, adopted manual
pollination as being more efficient than
nature.
The Mexicans plant vanilla by attacking a
forest with their machetes, and skillfully cut
away all but the upright young saplings of
trees with good foliage. These are called
the support trees. A shallow trench is next
scooped around each sapling, and one or
two cuttings, or slips, of the vanilla vine are
planted loosely, usually in January, and tied
to the tree. In a short time, the cuttings send
forth roots, which creep along the surface of
the ground beneath a mulch of decayed
leaves and vegetation. The upper part of the
cutting soon twines around the supporting
tree and grows in a zigzag fashion, thus
forming a garland.
The plant will flower the second year
of its growth. To strengthen the vines,
pollination is often delayed by the planters.
Clusters of 20 or more buds will arise on
short stalks in the angle between the leaf
and the stem. It may take as long as six
weeks for the bud to develop into a flower.
The satiny, lime-yellow orchid will achieve
full glory one morning, and by early after-
noon it is gone. Any woman who is for-
tunate enough to have been presented with
an orchid knows that, as beautiful as it is,
the flower has no aroma. The aroma and
flower seem to have been saved by nature
for the vanilla bean, from which the most
universally liked flavoring extract is made.
Curing Vanilla
The vanilla bean, as shipped to the United
States, resembles a good-sized string bean.
The matured pod as it is picked in the forest
is about the thickness of a man's middle
finger. It is obvious that somewhere in
between the bean has lost both size and
weight. In addition, neither the orchid
blossom por the green pod have much
vanilla flavor. Yet, pure vanilla has a flavor
for which it is justly famous.
In between picking and shipping is an
exacting process known as "curing." It is
during the curing process that pure vanilla
comes into its own as a flavor that has no
peer, for the flavor is the result of naturally
induced enzymatic action.
During the harvest season, workers move
among the vines every day. The beans do
not all mature at the same time, and they
must be picked at the moment when they
have gathered all the elements of their
flavor.
The Mexican, or sun process, is the oldest
curing method in use. In Mexico, few
planters of vanilla beans do their own
curing, since this is a highly developed
specialty. After being gathered, they are
usually loaded on mule trains, and trans-
ported to trading centers of which Papantla,
in Vera Cruz, is the oldest but no longer
the largest. These are nervous days for the
planter, for his investment in time and labor
is reaching its culmination. When he reaches
Papantla, or any of the other curing centers,
he visits the curers, rarely selling all his crop
to one firm, usually shopping around to see
if he can get better prices.
The buyers, in turn, must be highly
skilled to select healthy, ripe beans, for each
bean they are buying will lose about 80
percent of its weight in the curing process.
They must know market conditions, and
judge unerringly the quality of the bean
being offered. As soon as the beans are pur-
chased, the curing process gets underway.
There are two principal curing processes:
one as developed in Mexico, and one
•·

developed in Madagascar. The Mexican
process usually takes place in a series of
buildings that enclose a huge patio. The
beans are stored in sheds for a few days
until they start to shrivel. Next, the beans
are gathered rapidly and placed in large
mahogany sweating boxes. A number of
mats are placed over and around the
sweating box, so that proper temperatures
can be maintained for the important flavor-
developing enzymatic reactions, which are
accompanied by slight fermentation. This
important work lasts for at least 24 hrs., and
the whole process may be repeated as much
as six or eight times during the early part of
the curing, which will extend over a period
of two or three weeks. In this time, the
green beans acquire a dark chocolate brown
color.
Later on, the beans are given less fre-
quent sunnings and sweatings to help reduce
moisture to the proper levels. In between
times, they are held in large wooden trays
for further flavor development and de-
hydration. When hundreds of shells are
spread out on the patios, workers constantly
circulate among the rows, turning one over
here, feeling one there, watching the sky
at all times for signs of rain. When rain
threatens, the entire labor force moves
swiftly to the patio, and all the beans are
whisked inside and placed on racks.
The final stages of the curing take place
when the beans are sufficiently advanced to
be placed in aging boxes for a period of two
to three months, always receiving the usual
careful inspection.
Finally, the beans are bundled carefully
according to quality, and packed in the
special tins lined with waxed paper in which
they arrive in the market. Approximately
eight months have elapsed since the beans
were gathered. Millions of hours of careful,
tedious, laborious work have been expended
upon them by thousands of workers, who
earn a mere fraction of what similar work
would command in the United States.
The skilled workers seem to have pure
vanilla in their blood, for they know exactly
Natural Flavoring Materials 353
when the beans are ready for the next step.
One error and a year's work can be ruined.
The beans must be done to a turn-neither
exposed to the sun too long, nor too short a
period.
The shorter Madagascar curing starts by
wilting the green pods in hot water. For the
next 10 days or so, they are spread out on
blankets, usually on tables, and when quite
hot, are rolled up in the blankets to stand
overnight. The warmth provides good con-
ditions for the important enzyme reactions
accompanied by slight fermentation. The
beans are next spread on large trays, and
racked up, usually to the ceiling of the
curing warehouses, where they are allowed
to cure and dehydrate naturally. Finally,
these beans are sorted for quality and made
up into bundles, usually somewhat smaller
than those of Mexico. They are packed in
smaller tins, with classifications similar to
those of Mexico.
Classification of Mexican Beans
There are various grades of Mexican beans:
prime, good to prime, good, fair and
ordinary. The same grades apply to Mexican
cut beans.
The prime are the choicest beans, free of
scabs, warts and other blemishes. They are
chocolate brown to black in color. Their
aroma is clean and delicate. Crystallization
rarely exists. The beans are 6V2 to 9V2 inches
long.
The good (Buena) are dark brown, broad
and inclined to hardness, or rather tough-
ness. They give better yields of flavorable
substances because of their lower moisture
content.
Mexican Cut Beans
The prime cuts include shorts and longs.
They are usually considered as good as
whole beans. The flavor is good. The beans
are often crystallized. The ordinary cuts are
dry, broken beans of poorer or undeveloped
flavor from the early gatherings.
The Mexican process of curing consists of
354 Source Book of Flavors
repeated sweating and drying by the heat of
the tropical sun. Mexican cured beans are
normally better classified for quality than
other varieties.
Madagascar Vanilla
The vanilla plant was introduced about 1820
in Reunion Island ("Bourbon"), and in
Madagascar about 1841. It arrived first at
the small island of Sainte-Marie off the east
coast of Madagascar, then on Madagascar
itself, especially around Antalaha, which
remains the capital of vanilla preparation
and export.
Cultivation ofMadagascar Vanilla
Habitat
The essential characteristics of the habitat
of the vanilla plant call for the following
conditions:
A zone of cultivation which may stretch
from 20° North latitude to 20° South latitude,
at a maximum height of 1000-1300 ft.; or in
low-lying regions, river valleys where the
sea breezes penetrate easily; gentle or steep
hillsides. The climate must be hot with an
equable rather than a high temperature and
favorable yearly rainfall, for the combined
dampness of the air and the soil have a great
influence on the growth of the vanilla plant.
The soil need not necessarily be of clay or
alluvial, or volcanic origin, provided that
the chemical composition of the soil con-
tains the necessary fertilizing elements
(potassium, chalk, nitrogen, phosphoric
acid) for a maximum yield. To sum up, the
vanilla plant needs a very rich soil. Vanilla
plants growing in poor soils produce pods
that do not keep well.
Planting
The vanilla plant is propagated by cuttings
or sometimes by layering to replace the
missing plants. Cuttings 4 to 6ft. long are
laid horizontally in the ground, not very
deep, right at the foot of the future foster
mother trees, which will shade the lianas.
For maximum utility, the trees should meet
certain requirements called for by the de-
velopment of the plants: trees that do not
shed their bark, have no odor, are strong-
growing, and whose foliage does not fall.
Under the circumstances, it is wisest to
choose trees with tap roots because they
stand up better to hurricane winds and
because they exhaust the soil at a deeper
level. But the foster mother trees are not
enough protection against the violent dry
tropical winds, and screens of trees are
necessary for protection.
Their disposition is thus not an arbitrary
choice, and depends on the way in which the
vanilla plantation is laid out.
Pollination
The fragility of the Iiana is the main point in
the cultivation of the vanilla plant, and calls
for patience and very careful handling from
those who would grow it. Usually 18 months
pass before the vanilla plant flowers. The
flowering takes place at the following times
in those islands which produce it:
October to December in the Comoro
Islands.
November to January in Madagascar.
December to February in Reunion.
October to January in Tahiti, as the cultiva-
tion of vanilla in this group of islands
extends over many islands.
The delay in flavoring, which certain
planters prolong for 21/2 yrs., is necessary
to strengthen the plants so that the Iiana
is strong enough to withstand artificial
pollination. In all the islands, recourse must
be had to artificial pollination and it is done
between dawn and noon, a few hours after
the flowering, for the vanilla blossom opens
during the night and soon withers. Swarms
of women and children, armed with a
primitive style (a splinter of bamboo or a
fragment of the mid-rib of a palm leaf)
invade the plantation in order to perform
this operation, which calls for speed,
delicacy and skill.

It is carried out in three steps:
The first step is to disengage the upper part
of the gynosten.
The second step is to introduce the style
between the blades of the stigma and to
lift up the tongue, passing it under the
stamen.
In the third step, the pollen mass, com-
pressed by the operator's thumb, breaks
away and falls on the lower blade of the
stigma. Pollination then takes place.
As noted earlier, a certain species of bee
in Mexico permits natural pollination there.
Harvesting
After pollination a new period of waiting of
six or seven months begins, during which
the pods harden and swell. The fruits ripen,
while the yellowing of the tip of the pod
decides the moment of harvesting. This
must be done swiftly and at the right
moment.
The harvest takes place at the following
times:
Madagascar-between May and July.
Comoro Islands-between April and June.
Reunion-between June and August.
Tahiti and other islands-between April
and July.
Yield
It is extremely variable, and depends on
climatic conditions. A harvest of 900 to
1000 kg of green vanilla per acre is an
average yield in normal conditions. How-
ever, it must be noted that 3.5 to 4 kg
of green vanilla give 1lb. of commercial
vanilla. In this connection it must be men-
tioned that certain planters, chiefly in
Reunion, tend to dry the pods insufficiently,
and thus get 1lb. of commercial vanilla from
3lb of green vanilla. This vanilla, which is
too moisture-logged, keeps badly and is too
prone to mildew.
A plantation that begins to produce in the
Natural Flavoring Materials 355
third year of its existence as a rule goes on
producing for six to eight years.
Preparation ofMadagascar Vanilla Beans
Heat Treating
The harvesting, carried out swiftly but
steadily, is followed by the treatment in
which one of the first steps is to develop that
aromatic aldehyde called vanillin; this exists
in a natural state in vanilla (by weight, 1-3
parts in 1000).
It has been established that of the dif-
ferent methods of preparation in the dif-
ferent countries, the one most used is that
known as "Bourbon," in which the pods are
plunged into hot water, at a temperature of
80.4-84.4°C (176°-184°F). The time of
immersion is from 7 to 15 min (the tough-
ness of the skin decides it). This is to stop all
growth by destroying the chlorophyll in
order to ensure a more effective action of
the soluble ferments. In Tahiti and Mexico,
the heat of the sun is generally sufficient to
cause these changes.
Drying
Then, wrapped in a black woolen cloth, the
pods are exposed to the sun on trays, so that
they are not in contact with the soil. Next
comes the drying in the shade. This takes
five or six weeks; the nature of the pod
decides the time, which is settled by the
shrinking and the appearance of the pods.
At the end of this time, the pods have
turned brown and soft, and don't all have
the same appearance. Long or short; moist
or dry; marked with galls or cracks-in
order to be ready for market, they must be
classified.
Classification
In each category, measuring follows the
straightening and sorting; this makes it
possible to calculate the yield, as it results
in the constitution of groups as homogenous
as possible. It is, in fact, the length of the
pods that settles the price, and this differs
356 Source Book of Flavors
according to the place of origin, as the fol-
lowing figures will show:
Reunion: avg. 18-20cm; max. 25-26cm
Madagascar: avg. 16-18 em; max. 22-23 em
Comoro
Islands: avg. 15-16cm; max. 21-22cm
Nossi-Be: avg. 14-15cm; max. 20cm
Vanilla Bean Qualities The qualities of
vanilla (Bourbon variety) are the following:
Extra: Whole, unsplit, fine, fatty, oily pods,
of a uniform chocolate brown color,
without defects or galls, delicate aroma.
Moisture content is about 37.2 percent.
1st: Same kind as in the "extra" quality, but
the pods are not quite so fatty.
2nd: Pods not so large, of a chocolate brown
color, with a few small galls. Good
aroma. Moisture content is about 25.2
percent.
3rd: Rather thin pods hard, twisted, of a
slightly reddish chocolate brown color.
With fairly numerous galls. Good aroma
but nothing more. Moisture is about 13.7
percent.
4th (Ordinary): Rather dry pods of a
reddish color. May have numerous galls.
Rather ordinary aroma.
Inferior: The lowest category. Includes all
pods that cannot be placed in the higher
categories. Very dry pods, very reddish
color, rather "uncultivated" aroma,
which is, however, pleasant, especially in
the kinds coming from Madagascar.
These six kinds are known as "entire";
six corresponding "split" kinds exist and
they come between in the order of cate-
gories. Foxy splits are reddish-brown color,
thin, hard-cured and woody, shriveled,
short lengths, and dry; they are high in
vanillin and low in resin.
The residue, after preparing and packing
pods which are too short, broken or twisted,
is not put into bundles and form the lowest
category known as "in bulk."
A batch that has been prepared and
includes all or a part of the above categories
is a "head to tail batch." The head is
represented by the extra and first qualities;
the tail by those going from "1st quality
split" to "bulk." In trade circles, it is
allowed that a "head to tail batch" of vanilla
is ordinarily made up as follows:
50% first quality,
20% first split and second quality,
25% second split or inferior split,
5% bulk.
Packing
Tied up in bundles of 70 to 100 pods
weighing approximately 5 oz. to lib., they
are placed in tins from which they are pro-
tected by wax paper. These tins are put in
strong wooden cases, six per case, for
transport from the Indian Ocean regions.
Sources of Vanilla Beans
The place of origin of the vanilla beans often
uses some unique step in processing or
packaging of their product.
Indian Ocean The vanilla coming from
this area is sold by the planters of the
islands, sorted into the categories of the
Bourbon species.
Pacific Peculiarity of the packing.
Tahiti vanilla is packed in tins lined with
grease-proof paper, weighing about 40 kilos
net. Each wooden case contains only one
tin.
Atlantic Ocean Besides the Vanilla
planifolia the Pompona species is cultivated
in Guadeloupe. The batches sent off are
generally classified into three categories:
First, Second, Reddish.
Certain particularly careful packers tie a
black thread round each pod to stop it from
splitting. Shortage of labor is leading to the
abandonment of this practice.
The produce obtained after drying in
the sun gives off an aroma like that of
heliotrope. The appearance of the batches,
far less fine than those from the Indian
Ocean, betrays the less careful handling.

Composition of Vanilla Flavor
Cured vanilla beans contain vanillin,
secondary aromatic compounds, small
amounts of heliotropin (only in Tahiti),
volatile oil, resins, organic acids, fixed oil,
sugar, gum, tannin, wax, cellulose, and
water (Richard 1991). Their value is not
determined by the vanillin content, but
more by their fragrance.
The important secondary aromatic com-
pounds that are really responsible for vanilla
flavor are due to a complex of aromatic
aldehydes, alcohols, and esters whose large
numbers are different in the different
varieties of beans and in the different lots of
the same bean. Together, they form the
balsamic fragrance typical of vanilla flavor.
The volatile oil is also part of the balsam.
Resins are present in different types and
in varying amounts in vanilla beans. When
isolated, some of them have a pleasant taste
but no odor. Resins constitute, largely, the
lead-precipitating material of the beans.
They are soluble in alcohol and in alkalis,
and entirely insoluble in water. An extract
containing large amounts of resins will
retain aromatic compounds far longer than
one that has smaller quantities of them.
The various acids present in vanilla beans
become valuable when chemical changes
convert them to esters during the aging
process.
Extracting Vanilla and
Imitation Vanilla Flavor
In some countries, notably France and
Germany, the beans themselves are fre-
quently demanded by the consumer. In
America, where convenience is on par with
quality, homemakers prefer the extract.
The chemical composition of vanilla is
still not thoroughly understood. Vanillin is
only one of the components of flavor; it
is found in small amounts in the fully ripe
beans. The overall flavor is enhanced com-
pletely during the curing process. Yet of all
the natural flavorful constituents of the
Natural Flavoring Materials 357
cured vanilla bean, only vanillin is imitated.
In imitation vanilla flavor, the contributions
made to flavor by the other natural con-
stituents of vanilla are largely missing.
The pure vanilla has a delicate, yet rich
and mellow aroma. The imitation has a
heavy, grassy odor. In flavor, the pure
vanilla extract has a delicate, mellow after-
taste. The imitation has a less pleasant after-
taste. This can be detected in ice cream,
baked goods, and other commercial pro-
ducts by used the discriminating consumer.
Sellers of commercial vanilla extract
sometimes use a simple test to demonstrate
the flavor superiority of pure vanilla. They
pour pure vanilla on one lump of sugar, and
imitation on another. They first suck the
pure sample, and follow by sucking the
imitation. The flavor difference is imme-
diately noticed.
Blending of Vanilla Beans
In the production of vanilla flavor, blends of
various grades of vanilla beans are extracted
to meet the requirements of the ice cream,
confectionery, bakery and other food in-
dustries. The most preferred combinations
of Bourbon beans are:
a. 50% Madagascar Bourbon vanilla
beans-firsts
30% Madagascar Bourbon vanilla
beans-thirds
20% Madagascar Bourbon vanilla
beans-foxy splits
b. 50% Madagascar Bourbon vanilla
beans-firsts
15% Mexican cuts, medium dry,
sweet, not woody
10% Mexican vanilla beans-firsts
25% Madagascar vanilla beans-foxy
splits
c. 50% Madagascar Bourbon vanilla
beans-firsts
25% Mexican vanilla beans
25% Java vanilla beans
d. 80% Madagascar Bourbon vanilla
beans-seconds
20% Madagascar Bourbon vanilla
beans-foxy splits
358 Source Book of Flavors
e. 15% Mexican cuts, medium dry,
sweet, not woody
35% Madagascar Bourbon vanilla
beans-thirds
50% Madagascar Bourbon vanilla
beans-fourths
f. 25% Madagascar Bourbon vanilla
beans-thirds
75% Madagascar Bourbon vanilla
beans-fourths
g. 50% Madagascar Bourbon vanilla
beans-thirds
50% Madagascar Bourbon vanilla
beans-foxy splits
For strong vanilla flavor the following
blend is used:
h. 75% Madagascar Bourbon vanilla
beans-thirds
25% Madagascar Bourbon vanilla
beans-fourths
The preferred Mexican blends are:
1. 60% Mexican vanilla beans-firsts
40% Mexican vanilla beans cuts,
medium dry, sweet, not woody
J. 48% Mexican vanilla beans-firsts
32% Mexican vanilla beans-cuts
20% Madagascar Bourbon vanilla
beans-firsts or seconds
Vanilla Extraction
Vanilla flavor is extracted from the beans
with alcohol since distillation destroys the
gentle fragrance of the aromatic compounds.
The color of vanilla extract is influenced by
the quality of the beans, the strength of the
alcoholic menstrum, the duration of the
extraction, and the presence of glycerin,
which is added to retard evaporation and to
retain the flavor in the extract. Dry beans
give a darker color than moist beans.
Glycerin deepens the color of the extract.
The amount of extractable color decreases
as the strength of the alcohol is decreased.
Aging
The purpose of aging is to bring out im-
proved aromas. Vanilla extract should not
be stored in new wooden barrels. The
vanilla absorbs tannins and other substances
with undesirable flavors from the wood.
Vanilla extract should not be stored in con-
tainers made of aluminum, lead, nickel, zinc
or copper. Vanilla is commonly stored in
stainless steel or glass containers.
An alcohol content of 42 to 45 percent
accelerates the chemical changes and for-
mation of esters from acids while aging.
During this period, the total ester content
of vanilla extract, as ethyl acetate, remains
fairly constant. However, the nature of the
esters changes considerably. The esters of
higher alcohols liberate the higher alcohols
upon hydrolysis, and the acids formed
reunite with lower alcohols, forming volatile
esters. The higher alcohols slowly oxidize
to give aldehydes. This reaction takes
place during storage and is often called
"alcoholysis of the esters."
There is a direct dependency between the
time of aging and the tempo of oxidation.
The slower the oxidation, the better are the
forthcoming changes in the esters which
produce the quality of aroma and taste in
vanilla.
Analytical Standards for Vanilla Extract
True vanilla extract should contain a
minimum of 13.35 oz. average of vanilla
beans per gallon, with no other ingredient
except alcohol (35 percent) and/or glycerin,
sugar and water.
The quality of vanilla extract cannot be
determined by chemical analysis alone.
Analysis determines the amount of vanillin
present, the lead number, the ash content,
and other values. It is used as a means
of learning whether the extract has been
adulterated. However, tests for analysis do
not indicate the quality of the beans used.
Winton's analytical values are often used as
a standard for detecting adulteration. These
values are presented in Table 7-82. There is
a relation between ash and lead number.
Over 80 percent of the total ash is soluble in
water.
 Natural Flavoring Materials 359

TABLE 7-82. Composition of vanilla extract Alkalinity of ml 0.1 N acid per 100 ml
Min Max Avg soluble ash: extract
Vanillin, grams per 100 ml Total acidity: ml 0.1 N alkali per 100 ml
extract 0.11 0.35 0.19 extract
Ash, grams per 100 ml
extract 0.22 0.432 0.319
Acidity other ml 0.1 N alkali per 100 ml
Soluble ash, grams per than vanillin:
100 ml extract 0.179 0.357 0.265
Lead number (Winton) 0.40 0.74 0.54
extract
Alkalinity of total ash, N/10
acid per 100 ml extract 30.00 54.00
Alkalinity of soluble ash,
N/10 acid per 100 ml
extract 22.0 40.0 30.0 Powdered Vanilla
Total acidity, N/10 alkali
per 100 ml extract 30.0 52.0 42.0 Powdered vanilla is made either by mixing
Acidity other than vanillin,
N/10 alkali per 100 ml ground beans with sugar or by extracting the
extract 14.0 42.0 30.0 flavoring from the beans and then mixing
with sugar.

The ash values are useful because the

ingredients of imitation vanilla, namely,
vanillin, coumarin and substitute sugar,
glycerin and other solvents, are practically
free from ash. On the other hand, the use
of an alkali in the manufacture of vanilla
extracts will increase the amount of ash, but
would also change the values for solubility
and alkalinity.
The acidity is due chiefly to organic acids
that are dissolved from the beans, and to a
lesser degree to natural vanillin; this acidity
is a characteristic of a genuine vanilla
extract. Low total acidity or acidity other
than vanillin is indicative of adulteration.
Practically the same values are obtained
with or without sugar or glycerin in the
menstruum. Lower alcohol content in the
menstruum increases the ash values and
diminishes the acidity.
The use of vanillins and Tahiti beans can
be detected by testing for anisyl alcohol,
anisyl aldehyde and anisic acid, which are
not contained in the Mexicans, Bourbons,
South Americans, and Javas.
Important criteria concerning quality of
vanilla extract:
Vanillin content: g per 100 ml extract
Ash: g per 100 ml extract
Soluble ash: g per 100 ml extract
Lead number: percent of extract
Resin: percent of extract
Oleoresin of Vanilla and
10-Fold Vanilla Flavor
Oleoresin of vanilla is derived by evapora-
tion, under vacuum, of the menstrum from
an extract of comminuted vanilla beans. A
Fitzpatrick Comminuting Machine is often
used for the comminution of the beans. The
remaining concentrate in the still is a residue
consisting mainly of the resinous substances
of the vanilla beans in which very little of
the balsamic flavor of the original flavoring
extract is left.
Oleoresin of vanilla, which is diluted with
solvents and reduced to 1-, 2-, or 10-fold
strength, is in reality a compound and
usually requires the addition of vanillin
to yield a vanilla flavor. The dilution of
oleoresin is not a flavoring extract since it
does not contain all the aromatic substances
of an extracted flavor.
The normal yield of oleoresin of vanilla is
lib. oleoresin from 2lbs. of vanilla beans.
One gallon of 10-fold vanilla flavor is
obtained by dilution with solvents of
oleoresin of vanilla, which is derived from
133.5 oz. by weight of vanilla beans. No
more than a four-fold concentration of
vanilla flavor is possible by extractive
methods. Distillation in any form destroys
the fragrance of the aromatic substances of
vanilla flavor.
360 Source Book of Flavors

Chemistry volatiles-a comprehensive analysis. Int.

The chemistry of vanilla extracts is complex
and an analysis of a typical natural extract
reveals the presence of (Maarse and Visscher
1989):
Hydrocarbons 40 Alcohols 25
Carbonyls, Carbonyls, ketones 10
aldehydes 11 Esters 41
Acids 20
Bases 3
Lactones 2 Acetals 1
Sulfur compounds 1 Phenols 10
Ethers 5 (Ep) oxides, pyrans,
Furans 10 coumarins 2
Klimes and Lamparsky (1976) have
published some of the most detailed inves-
tigations on vanilla flavor. Of the 170 com-
pounds identified, only 30 were found at
concentrations greater than 1 ppm.
References: Vanilla
Ansaldi, G., Gil, G., and Petit, J., Ia. 1990.
Process for production of natural vanilla
aroma by treatment of green vanilla pods, and
the aroma so produced. French Patent Appli-
cation. FR 2 634 979 Al.
Archer, A.W. 1989. Analysis of vanilla essences
by high-performance liquid chromatography.
J. Chromatog. 462:461-466.
Burri, J., Graf, M., Lambelet, P., and Loeliger,
J. 1989. Vanillin; more than a flavoring
agent-A potent antioxidant. J. Sci. Food
Agric. 48(1):49-56.
Clark, G.S. 1990. Vanillin: a profile. Perfum.
Flavor. 15(2):45.
DeWulf, 0., Thinart, P., Gaignage, P., Marlier,
M., Paris, A., and Paquot. 1986. Biocon-
version of vanillin to vanillyl alcohol by
saccharomyces cerev1s1ae. Biotechnol.
Bioeng. Symp. 17:605.
Fraise, D., Maquin, F., Stahl, D., Suon, K., and
Tabet, J.C. 1984. Analysis of vanilla extracts
by HPLC, coupled GLC-MS and MS-MS.
Analysis 12(2):63-71.
Ishiguro, M., Nanba, S., and Nakatsu, A. 1986.
Analysis of vanilla oleoresin. Kanzei Chua
Bunsekishoho 26:61-67.
Klimes, I. and Lamparsky, D. 1976. Vanilla
Flavours Food Additives 7:272-273, 291.
Krueger, D.A. and Krueger, H.W. 1985.
Detection of fraudulent vanillin labeled with
carbon-13 in the carbonyl carbon. J. Agric.
Food Chern. 33(3):323.
Lawrence, B.M. 1977. Vanilla extract. Perfum.
Flavorist 2(1):6- 7; Ibid. 2(2):31-32.
Leong, G., Archavlis, A., and Derbesy, M.
1989. Research on the glucoside fraction of
the vanilla bean. J. Essent. Oil Res 1(1):33-
41.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food-Qualitative and
Quantitative Data, Volumes I- Ill. Zeist:
TNO-CIVO Food Analysis Institute.
Mariani, M., Scotti, A., and Colombo, E. 1982.
Vanilla: from the origin to its analysis.
Quintessenza 18(32):3-25.
Maries, R.J., Compadre, C.M., and Farnsworth,
N.R. 1987. Coumarin in vanilla extracts: its
detection and significance. Economic Bot.
41(1):41-47.
Pouget, M.P., Pourrat, A., and Pourrat, H.
1990. Recovery of flavor enhancers from
vanilla pod residues by fermentation.
Lebensm.-Wissen. Techno!. 23(1):1-3.
Richard, H.M.J. 1991. Spices and Condiments
I. In Volatile Compounds in Foods and
Beverages, ed. H. Maarse, pp. 411-447. New
York: Marcel Dekker, Inc.
Riley, K.A. and Kleyn, D.H. 1989. Fundamental
principles of vanilla/vanilla extract processing
and methods of detecting adulteration in
vanilla extracts. Food Techno!. 43(10):64-77.
Schmidt, E. and Maier, H.G. 1989. Thermo-
stable binding of vanillin to starch. Git-Suppl.
2:40-42.
Sherma, J., Schafer, S.L., and Morris, K. 1987.
Determination of coumarin in vanilla
flavorings by quantitative high performance
thin layer chromatography. J. Liq.
Chromatog. 10(16):3585-3593.
Sullivan, G. 1984. Major aromatic constituents in
mexican vanilla extracts. Tex J. Sci. 36(1):
17-23.
Thompson, R.D. and Hoffmann, T.J. 1988.
Determination of coumarin as an adulterant
in vanilla flavoring products by high-perform-
ance liquid chromatography. J. Chromatog.
438(2):369-382.
Tokoro, K., Kawahara, S., Amano, A.,
Kanisawa, T., and Indo, M. 1990. Glucosides

in vanilla beans and changes of their contents
during maturation. In Flavour Science and
Technology, eds. Y. Bessiere and A.F.
Thomas, pp. 73-76. New York: John Wiley &
Sons.
Vidal, J.P., Fort, J.J., Gaultier, P., and Richard,
H.M. 1989. Vanilla aroma extraction by dense
carbon dioxide. Sci. Aliments. 9(1):89-100.
VEGETABLES
Vegetables are consumed mainly for their
nutritive values. Some are rich in carbo-
hydrates, others in proteins, mineral salts
or vitamins, etc., but most contain volatile
components that give them a distinctive and
often quite attractive flavor, which will
change considerably on cooking. In addition,
many vegetables are highly colored and con-
tribute an attractive eye appeal. With few
exceptions (e.g., the alliaceous vegetables
such as onion, garlic, etc.), table vegetables
are not really considered as a prime source
of flavor. Some, however, have a sufficiently
popular appeal to make them worthy of
imitation, so enabling the flavor profile to be
used in end products where incorporation of
the vegetable itself would pose technical
problems or where the use of dehydrated
vegetables results in an inadequate profile.
This applies particularly to the vegetables
covered in this section of text. For a more
complete discussion of the flavor properties
of vegetables as a whole, Whitfield and Last
(1991) have provided a recent overview of
the subject.
Celery
The well-developed, fleshy leaf stalks of
celery (Apium graueolens L.) are widely
used as a culinary vegetable, which is
usually eaten raw although cooked celery
contributes significant flavor to soups and
stews, etc. Stick celery has an attractive but
mild flavor, as well as being a rich source
of mineral salts and vitamins. In European
countries, the stalk is generally white,
having been etiolated by exclusion of light
during its growth; in the United States, the
Natural Flavoring Materials 361
natural green stalk is preferred, although
some may be marketed after blanching with
ethylene gas. A variety known as celeriac
(A. graueolens var. rapaceum DC.) has a
much swollen fleshy rootstock whose flavor
is stronger than that of celery.
The principal source of celery flavor in
food processing is the essential oil distilled
from the ripe seed. The aromatic profile of
this is far removed from that of the fresh
green vegetable. A total of 156 compounds
have been identified in various extracts of
fresh celery (Whitfield and Last 1991). The
major constituents are limonene (214mg/
kg), p-menth-8-ene-1,2-diol (11 mg/kg), P-
selinene (7.5 mg/kg), methylamine (6.4mg/
kg), dimethylamine (5 mg/kg), (Z)-3-
hexenol (4.5 mg/kg), myrcene (4mg/kg),
P-caryophyllene (3.8 mg/kg), (E)-carvyl ac-
etate (3.4 mg/kg), benzylamine (3.4 mg/kg)
and 3-butylphthalide (3 mg/kg) (Maarse
and Visscher 1989). The compounds most
responsible for aroma appear to be 3-
butylphthalide, P-selinene and sedanolide
(3-butyl-3a, 4,5 ,6-tetrahydrophthalide).
Potato
The potato (Solanum tuberosum L.) is a
swelling at the end of an underground stem
(i.e., a tuber). This popular vegetable is
a major source of carbohydrates in many
temperate regions. Potatoes are used in
enormous quantities not only as a table
vegetable (boiled, baked, fried, etc.) but
processed as French fries (often marketed
frozen), sliced as potato chips (crisps),
dehydrated as potato powder or flakes for
reconstitution as instant mashed potato, etc.
The flavor of raw and, hence, of cooked
potatoes depends not only on variety but on
all the many variables that occur during
growing, harvesting, storage and processing
(both domestic and commercial). The flavor
quality of potatoes used in food processing
may seriously affect the acceptability of the
end product, particularly in the manufacture
o~ potato chips and french fries. In order to
reduce some of the processing problems,
362 Source Book of Flavors
recent developments have been along the
lines of using dehydrated potatoes, recon-
stituted into a dough, rolled and cut (or
formed) prior to frying. The resulting
product has a uniform appearance, but
some of the intrinsic potato flavor is lost
during the process. There is an interest in
adding potato flavoring to the dough in order
to recapture some of the lost attributes.
Flavor Constituents
Whitfield and Last (1991) have provided
a good review of potato flavor and, there-
fore, this section will provide only a brief
overview.
Raw and Boiled Potato
A total of about 140 compounds have been
identified in raw, boiled and dehydrated
potato (Maarse and Visscher 1989). The
major flavor constituents in raw potato
have been identified as 1-octen-3-ol, (E)-
2-octenol, (E)-2-octanal and geraniol. 2-
Isopropyl-3-methoxypyrazine was also iden-
tified and is considered to give the earthy
note to the potato (Buttery, Seifert, and
Ling 1970; Buttery and Ling 1973).
Ninety-five flavor constituents have been
identified in boiled potato (Whitfield and
Last 1991). 3-(Methylthio )propanal (200 ng/
L), 1-octen-3-ol (1.4ug/L), phenylacetal-
dehyde (4ug/L), (E)-2-nonenal (89ng/L),
2-ethyl-3-methoxypyrazine (425 n/L), 2-iso-
propyl-3-methoxypyrazine (2ng/L), dimeth-
yl disulfide (300 ng/L), methional (200 ng/L)
and dimethyl sulfide (200ng/L) are con-
sidered to be most important to the aroma
of boiled potato. Oxidation products (un-
saturated aldehydes) also make a lesser
contribution.
Baked Potato
A total of 252 flavor compounds have
been identified in baked potato. 2-Ethyl-
3,6-dimethylpyrazine and 2-vinylpyrazine
contribute the baked, buttery and potato-
like aroma, while 2-ethyl-3-methylpyrazine
contributes a pleasant earthy nutty note.
Five-and six-membered bicyclic pyrazines
(e.g., 5-methyl-6, 7-dihydro-5H-cyclopenta-
pyrazine and 5,7-dimethyl-1,2,3,4,7,8-hexa-
hydroquinoxaline) as well as some oxazoles
and thiazoles also have been identified and
are known to possess baked potato, nutty
or earthy notes characteristic of the baked
potato aroma (Coleman, Ho, and Chang
1981).
Rhubarb
Rhubarb (Rheum rhaponticum L., or R.
palmatum L.), a vegetable which is
popularly regarded as a fruit because it is
primarily eaten as a dessert, is a native
of Tibet or northern Asia. It is a large.
perennial herbaceous plant with a thick,
much-branched rootstock and with large
green leaves borne on long red to greenish-
red fleshy petioles (stalks). It is the petioles
or stems that are eaten cooked (never raw);
the leaves contain high levels of oxalic acid
and should never be eaten. Rhubarb root,
derived from R. palmatum and not from
R. rhaponticum, is used medicinally as a
purgative. Rhubarb contains L-malic, citric
and oxalic acids, together with much smaller
quantities of other acids, whose balance
and location are subject to considerable
variation, depending on seasonal changes
and the state of maturity at the time of
collection.
The volatile constituents of rhubarb have
been investigated by Frattini et al. (1974).
Tomato
Tomatoes form one of the most popular and
flavorful of the vegetables. The tomato
plant (Lycopersicon esculentum Mill.) is
a native of South America, but is now
extensively cultivated, out-of-doors and
under glass, in very many countries. The
quality of tomatoes, particularly from a
flavor point of view, is very variable; size
and flavor are often inversely related and
color is not necessarily an indication of
flavor quality. Flavor components of
tomatoes, both volatile and nonvolatile,

are influenced by inherent and/or environ-
mental factors.
Tomatoes are processed in numerous
ways: canned, dehydrated, frozen, pickled,
or made up into chutney or ketchup,
pureed, juiced, etc. The techniques em-
ployed vary with the end product; for
details, refer to Gould (1974) or one of
the standard texts dealing with vegetable
processing.
Color
Color is a significant attribute of raw
tomatoes and tomato products such as paste
and powder. It is influenced by the ripeness
at harvest and is due to a complex mixture
of carotenoids. It was generally believed
that these consisted of a relatively high level
of lycopene and a much smaller proportion
of ~-carotene, but Liu and Luh (1977) found
that many varieties do not contain any ~­
carotene and that lycopene is present only
in the red varieties. They reported that the
total carotenoid level increased with matur-
ity of the fruit and established the presence
of phytoene, phytyolfuene, neo-~-carotene
B, all-trans-~-carotene, y-carotene, <>-
carotene, neurosporene, all-trans-lycopene,
torulene and mutatoxanthin. The coloring
value of tomato is discussed in the chapter
on natural coloring materials.
Flavor
Maarse and Visscher (1989) have tabulated
219 volatile compounds as having been iden-
tified in fresh tomato and tomato products.
The compounds considered to be most im-
portant to raw tomato are (Z)-3-hexenal
(250 n/kg), 3-methylbutanal (200 ng/L), ~­
ionone (7ng/L), 1-penten-3-one (1 ug/L),
hexanal (4.5ug/L), (Z)-3-hexenol (70ug/L),
(E)-2-hexenal (17ng/L), 2- and 3- methyl-
butanol (250 ug/L), 2-(2-methylpropyl)thia-
zole (3.5ug/L), eugenol (6ug/L), and 6-
methyl-5-hepten-2-one (30 ug/L) (Buttery,
Teranishi and Ling 1987). Dimethyl tri-
sulfide and damascenone may also make a
contribution to tomato flavor (McGlasson
Natural Flavoring Materials 363
et al. 1987, Buttery, Teranishi and Ling
1988).
Dimethyl sulfide is the major constituent,
quantitatively and sensorially, in canned
tomatoes (Miers 1966; Guadagni and Miers
1969). Canned tomatoes contain 1.6-
7.9mg/kg and tomato paste 3.6-10.9mg/kg
of this compound.
References: V-egetables
British Patent. 1975. Celery-like flavour. British
Patent 1 400 703.
Buttery, R.G. and Ling, L.C. 1973. Earthy
aroma of potatoes. J. Agric. Food Chern. 21:
745-746.
Buttery, R.G., Seifert, R.M., and Ling, L.C.
1970. Characterization of some volatile potato
components. J. Agric. Food Chern. 18:538-
539.
Buttery, R.G., Teranishi, R. and Ling, L.C.
1987. Fresh tomato aroma volatiles: a
quantitative study. J. Agric. Food Chern. 35:
540-544.
Buttery, R.G., Teranishi, R. and Ling, L.C.
1988. Identification of damascenone in tomato
volatiles. Chern. Ind. (London) 238.
Coleman, E.C., Ho, C.-T., and Chang, S.S.
1981. Isolation and identification of volatile
compounds in baked potatoes. J. Aric. Food
Chern. 29:42-48.
German-Democratic-Republic-Standard; TGL
12 161. 1987. Fresh rhubarb (Rheum
rhabarbarum).] Rhabarber, frisch. (Rheum
rhabarbarum L.). German Democratic
Republic, Zentrales Warenkontor Obst,
Gemuese und Speisekartoffeln.
Gould, W.A. 1982. Raw tomato color evalua-
tion. Research-Circular. -Ohio-Agricultural-
Research-and-Development-Center No. 271:
18-20.
Guadagni, D.G. and Buttery, R.G. 1974.
Tomato flavor enhancement. United States
Patent 3 826 851.
Guadagni, D.G. and Miers, J.C. 1969. Statistical
relationship between methyl sulfide content
and aroma intensity in canned tomato juice.
Food Techno/. 23:375-377.
Gumbmann, M.R. and Burr, H.K. 1964.
Volatile sulfur compounds in potatoes.
J. Agric. Food Chern. 12:404-408.
Hayase, F., Chung, T.Y., and Sontag, G. 1984.
364 Source Book of Flavors
Changes of volatile components of tomato
fruits during ripening. Food Chern. 14(2):113.
Jones, R.A. and Scott, S.J. 1984. Genetic
potential to improve tomato flavor in com-
mercial F1 hybrids. J. American Soc. Hort.
Sci. 109(3):318-321.
Kashiwada, Y., Nonaka, G.l., Nishioka, 1., and
Yamagishi, T. 1988. Galloyl and hydroxy-
cinnamoylglucoses from rhubarb. Phytochem
27(5):1473-1477.
Liu, Y.K. and Luh, B.S. 1977. The effect of
harvest maturity on carotenoids in pastes
made from VF-145-7879 tomatoes. J. Food
Sci. 42:216-220.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Food. Zeist: TNO-CIVO Food
Analysis Institute.
Matz, S.A. 1976. Snack Food Technology, West-
port, Conn. A VI Publishing Co.
McGlasson, W.B., Last, J.H., Shaw, K.J. and
Meldrum, S.K. 1987. Influence of the non-
ripening mutants rin and nor on the aroma of
tomato fruit. Hort. Sci. 22:632-634.
Miers, J.C. 1966. Formation of volatile sulfur
compounds in processed tomato products.
J. Agric. Food Chern. 14:419-423.
Ohshima, Y., Ohno, Y., Kajiyama, K., and
Takahashi, K. 1986. High performance liquid
chromatographic separation of rhubarb con-
stituents. J. Chromatog. 360(1):303-306.
Pareles, G.R. and Chang, S.S. 1974. Indentifi-
cation of compounds responsible for baked
potato flavor. J. Agric. Food Chern. 22:339-
340.
Stevens, M.A. 1970. Vegetable flavors. Hortic.
Sci. 5:95.
Tateo, F., Cavalli, S., and Pozzoli, M.A. 1982.
Preparation of East Indian rhubarb extracts
by an enzymic method. Rivista-della-Societa-
Italiana-di-Scienza-dell'Alimentazione 11 (3):
183-188.
Treptow, H. 1985. Rhubarb (Rheum sp.) and
its use.] Rhabarber (Rheumarten) und seine
Verwendung. Ernaehrung 9(3):179-183.
Tressler, D.K. and Joslyn, M.A. 1971. Fruit and
Vegetable Juice Processing Technology, 2nd
Edition. A VI Publishing Co., Westport,
Conn.
Uhlig, J.W., Chang, A., and Jen, J.J. 1987.
Effect of phthalides on celery flavor. J. Food
Sci. 52(3):658-660.
Whitfield, F.B. and Last, J.H. 1991. Vegetables.
In Volatile Compounds in Foods and
Beverages, ed. H. Maarse, pp. 203-269, New
York: Marcel Dekker.
Wright, D.H. 1983. The effect of nitrogen and
potassium fertilization on tomato flavor. Dis-
sertation-Abstracts-International, -B; 43(10)
3182: Order no. DA8306177.
Wright, D.H. and Harris, N.D. 1985. Effects
of nitrogen and potassium fertilization on
tomato flavor. J. Agric. Food Chern. 33(3):
355-358.
Chapter 8
Plant Materials Used in
Flavorings

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Achillea (Yarrow) Achillea nobilis Flowering Camphoraceous,

tops spicy, bitter
Agrimony Agrimonia eupatoria Flowering Aromatic, bitter
tops
Ajowan Carum ajowan Fruits Spicy, thyme-like,
sharp, biting
Alant
(Elecampane)
Alexanders Smyrnium olusatrum Herb Celery-, parsley-like
(Black lovage)
Alfalfa Medicago sativa Herb Hay-like GRAS (182.10,
182.20)
Alkanna Alkanna tinctoria Root Coloring principle (Extract) GRAS
(alkannin)
Allspice (Jamaica Pimenta dioica Berry Strongly phenolic GRAS (182.10,
pepper) Leaf 182.20)
Almond, Sweet Prunus amygdalus Nut GRAS
var. dulcis
Bitter var. amara Benzaldehyde (Oil-FFPA)
(182.20)
GRAS
Aloe Aloe barbadensis and Juice Intensely bitter (172.510)
spp.
Althea Althea officina/is Root 172.510
(Marshmallow) Flower
Ambrette (Musk Hibiscus abelmoschus Seed Sweet, floral-musky GRAS (182.10,
mallow) 182.20)
Amyris Amyris balsamifera Wood Faint, unpleasant (Oil)
(West Indian 172.510
sandalwood)
Angelica Angelica archangelica Seed Strongly penetrating GRAS
Root Musky
Leaf
Stem
Explanations of the status numbers will be found at the end of the table.

365
366 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Angelica, wild Angelica sylvestris (182.10)

Angola Weed Roccella fuciformis Herb Bitter 172.510 (A.B.)
Angostura Galipea officina/is Bark Aromatic, bitter GRAS (182.10,
G. cusparia 182.20)
Anise Pimpinella anisum Fruit Sweetly spicy GRAS (182.10,
Greenleaf 182.20)
Anise pepper Xanthoxylum Berry Aromatic, pungent
pipesitum
Anise, China star Illicium verum Fruit Sweetly spicy GRAS (182.10)
Apricot kernel Prunus armenica Fruit (Oil-Persic oil)
(182.40)
GRAS
Areca (Betel nut) Areca catechu Nut Faintly cheese-like
Arnica Arnica montana and Flower Strongly aromatic, 172.510 (A.B.)
other spp. Root pungent
Artemisia Artemisia absinthium Herb Herbaceous-green, 172.510 thujone-
(Wormwood) ·.varm, dry-woody free (A.B.)
Artichoke Cynara scolymus Leaf Bitter 172.510 (A.B.)
Asafetida Ferula assa-foetida Gum resin Alliaceous GRAS (182.20)
and other spp.
Ash Fraxinus exelsior Fruit Mildly aromatic
Leaf Bitter
Avens Geum urbanum Root Sweetly clove-like
Fresh leaf
Balm (Balm mint, Melissa officina/is Herb Fresh herbaceous GRAS (172.510,
lemon balm) Lemon-like 182.20)
Balsam Peru Myroxylon pereirae Oleo-gum Smoky, richly GRAS (182.20)
resin balsamic, cinnamic
BalsamTolu Toluifera balsamum Gum Pleasantly aromatic
Exudate Vanilla-like
Basil, bush Ocimum minimum Leaves, Warm spicy aroma, GRAS 182.10
flowering mint like
tops
Basil, sweet Ocimum basilicum Herb Sweet spicy, anisic GRAS (182.10,
182.20)
Bay laurel Laurus nobilis Leaf Light, aromatic, GRAS (182.10,
(Sweet bay) cineolic 182.20)
Bay, West Indian Pimenta racemosa Leaf Strongly phenolic GRAS (182.20)
(Myrcia acris)
Benzoin Styrax benzoin and Gum-oleo Strongly cinnamic 172.510
otherspp. resin
Bergamot Citrus aurantium Herb Sweetly aromatic GRAS (182.20)
(Oswego tea)
Betony Betonia officina/is Herb Aromatic, musky
(Woundwort) V.S.A.-Stachys
hysopifolia
Birch, sweet B etulina lenta
Bitter almond Prunus amygdalus, P. Nut (Oii-FFPA)
armenica, P. persica GRAS (182.20)
Blackberry Ebatus rubus Root bark 172.510
Bog myrtle Myrciagale Herb Sweetly aromatic
Bois de rose Aniba rosaeodora Sweetly woody, floral, GRAS (182.20)
(Rosewood) spicy
 Plant Materials Used in Flavorings 367

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A.•

Boldus Penmus boldus Leaf Spicy, oily 172.510 (A.B.)

Borage Borago officina/is Leaf Cucumber-like,
cooling
Boronia Boronia megastigma Leaf Violet-like 172.510
Bryonia Bryonia alba Root 172.510 (A.B.)
Brooklime (Water Veronica beccaburga Leaf
pimpernel)
Buchu Barosma betulina, Leaf Bittersweet, minty- 172.510
B. crenulata, camphoraceous
B. serratifolia
Buckbean M enyanthes trifoliata 172.510 (A.B.)
Buckthorn Rhamnus frangula Fruit
Burdock Artium lappa Root
Burnet Poterium sanguisorba Leaf
Cacao Theobroma cacao Seed Chocolate flavor when GRAS (182.20)
roasted
Cajeput (Ti Tree) Melaleuca Cineolic, 172.510
leucadendron and camphoraceous
other spp.
Calamint Calamintha ascendens Herb Mint-like
Calamus Acarus calamus Root Sweetly aromatic,
(Sweet flag) woody, spicy
Calendula Calendula officina/is GRAS (182.10)
Calumba Jetorhiza palmata Root Bitter 172.510 (A.B.)
Camomile German-Matricaria Flower Warm, bitter, (Essential oil)
(Chamomile) chamomila Heads Herbaceous GRAS (182.10,
Roman-Anthemis 182.20)
nobilis
Camphor tree Cinnamomom Leaf Camphoraceous 172.510
camphora safrole-free
Cananga Cananga odorata Flower Sweetly floral (Essential oil)
GRAS (182.20)
Candlenut Aleurites moluccana Nut Spicy when roasted
Caper Capparis rupestris, Buds and Fermented flavor GRAS (182.10)
C. inermis, flowers Goat-like
C. spinosa
Capsicum Capsicum annuum Fruit Variously pungent GRAS (182.20,
and other spp. 182.10)
Caraway Carumcarvi Fruit Minty-anisic GRAS (182.10)
Green leaf (182.20)
Caraway, black Nigella sativa GRAS (182.10)
(Black cumin)
Cardamom Elettaria Fruit Warmly spicy, GRAS (182.10,
cardamomum camphoraceous, 182.20)
cineolic
Carob Ceratonia siliqua Fruit GRAS (182.20)
Carrot Daucus carrota Seed Sweetly aromatic, GRAS (182.20)
earthy backnote
Cascara Sagrada Rhamnus purshiana Bark Bitter-tonic 172.510
Cascarill bark Croton eluteria Bark Bitter spicy odor GRAS (182.20)
Cassia, Chinese Cinnamomum cassia Dried Bitter, pungent and GRAS (182.10,
inner burning 182.20)
bark
368 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A. •

Cassia Padang- Bark Sweetly spicy, GRAS (182.10,

Cinnamomum cinnamic 182.20)
burmanii
Saigon-C. loureirii
Cassie Acacia farnesiana Flower Warmly spicy 172.510
Cassava Manihot esculenta, Root GRAS
M. utilissima
Castor Oil Ricinus communis Seeds 172.510
Catmint (Catnip) Nepeta cataria Leaf Minty, tomcat-like
Catechu, black Acacia catechu Wood and Strongly astringent 172.510
fruit
Cayenne pepper Capsicum truescens or Fruits Mild to highly pungent GRAS (182.10)
Capsicum annumum
Cedar, white Thuja occidentalis or Leaf Freshly (Essential oil)
Juniperus virginiana camphoraceous 172.510 thujone-
free
Celery Apium graveolens Fruit Warmly spicy, bitter GRAS (182.20)
Stems
Celery seed Apium graveolens Seeds Rich spicy odor GRAS (182.10)
Centaury Centaurium Herb Bitter 172.510 (A.B.)
umbellatum,
C. minimus
Cherry laurel Prunus laurocerasus Bark Bitter almond-like 172.510max
Leaf 25 ppm prussic
acid
Cherry, wild Prunus serotina Bark Bittersweet, medicinal GRAS (182.20)
Cherry Pits Prunus avium, Pits Pleasant, astringent 172.510, not to
P. cerasus sweet -sour taste exceed 25 ppm.
prussic acid
Chervil Anthriscus cerefolium Herb Anisic, delicately GRAS (182.10,
herbaceous 182.20)
Chestnut Custanea dentata Leaf 172.510
Chicory (Endive) Chocorium intybus Leaf Mildly bitter GRAS (182.20)
Chirata Swertia chirata Herb Bitter 172.510 (A.B.)
Chive Allium schoenoprasum Leaf Delicately onion-like GRAS (182.10)
Cinchona Red-Cinchona Bark Bitter 172.510 (A.B.)
succirubra
Yellow- max 83 ppm total
C. ledgeriana alkaloids in
and hybrids finished beverage
Cinnamon Cinnamomum Bark Sweetly spicy GRAS (182.10,
(Cassia) zeylanicum C. cassia Leaf 182.20)
and other spp.
Cinquefoil Potentilla rep tans, Root Astringent
P. canadensis Leaf
Citronella Cymbopogon nardus Leaf Fresh, sweet, (Essential oil)
lemon-like GRAS (182.20)
Citrus peels various citrus spp. Peel GRAS (182.20)
Clary sage Salvia sclarea Leaf Strongly aromatic GRAS (182.20,
Flower Slightly citrus-like 182.10)
Clove Syzgium aromaticum Flower Strongly phenolic GRAS
(Eugenia Bud
caryophyllata)
 Plant Materials Used in Flavorings 369

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Clover Trifolium spp. Leaf GRAS (182.20,

182.10)
Coca Erythroxyium coca Leaf Bitter GRAS-
and other spp. deccainized
(182.20)
Cocillana Guarea rusbyi Bark Bittersweet
Coconut Cocos nucifera Fruit Sweetly nutty GRAS
Coffee Coffea robusta and Seed Fermented and GRAS (182.20)
otherspp. roasted flavor
Cola Cola acominata Scott Nut Bittersweet, astringent
and End L.
Comfrey Symphytum officinale Root
Copaiba Copaefera spp. Balsam Faintly spicy, peppery, 172.510
woody
Coriander Coriandrum sativum Fruit Sweetly aromatic, GRAS (182.10,
(Chinese fruity 182.20)
parsley)
Cork oak Quercus suber, Bark 172.510 (A.B.)
Q. occidentalis
Costmary Chrysanthemum Herb Spicy, balsamic 172.510 (A.B.)
(Bible leaf) balsamata
Costus Sansurrea lappa Root Strongly goat-like 172.510
Cress Garden-Lepidium Leaf Pungent
sativum
American-Barbarea
verna
Water-Rorippa
nasturtium
acquaticum
Cubeb Piper cubeba Fruit Warmly 172.510
camphoraceous,
spicy, bitter
Cumin Cuminum cyminum Fruit Uniquely aromatic, GRAS (182.20,
pungent 182.10)
Cumin, black Nigella sativa GRAS (182.10)
(Black caraway)
Curacao orange Citrus aurantium Peel Mild to bitter GRAS (182.20)
peel(orange, astringent flavor
bitter peel)
Currant, Black Ribes nigrum Buds, Strong, aromatic odor 172.510
leaves
Curry leaf Chalcas koenigii or Leaf Distinctly curry-like,
Helichrysum spicy
augustifolia
Curcuma Curcuma longa Rhizome Freshly spicy,
distinctive
Cusparia Galipea officina/is Bark GRAS (182.20)
Daikon Raphanus Vegetable Sharply pungent,
(White radish) raphanistrum warming
Damiana Turnera diffusa var. Leaf Camomile-like, 172.510
aphrodisaca astringent
Dandelion Taraxacum officinale, Leaf Bitter (Extract)
T. laevigatum Root GRAS (182.20)
370 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A.•

Davana Artemisia pa/lens Herb Sharply bitter, 172.510

herbaceous
Dictam Dictamus hispanicus Flowering Sweetly aromatic, 172.510
Herb anisic
Dill Anethum graveolens Fruit Warmly spicy,
Fresh caraway-like
leaves
Dill, Indian Anethum sowa Fruit 172.510
Dittany Dictamus a/bus Root Bitter 172.510 (A.B.)
(Fraxinella)
Dittany of Crete Origanum dictamus 172.510
Dog grass (Couch Agropyron repens Rhizome (Extract)
grass, Triticum) GRAS (182.10)
Dragon's blood Doemonorops Resinous Crimson color; 172.510
propinquus, D. secretion benzoic when heated
ruber and other spp. of fruit
Dulse Rhodymenia palmata
Elder Sambucus nigra, Flower Muscate-like, sickly GRAS (182.10,
S. canadensis Berry sweet 182.20)
Elder Leaf 172.510 in
alcoholic
beverages only.
(Not exceed
25 pp prussic
acid in the
flavor)
Elecampane lnula helenium Rhizome, Aromatic 172.510 (A.B.)
root
Elemi Canarium commune, Gum resin Agreeably aromatic 172.510
C. luzonicum,
Amyris elemifera
Erigeron Erigeron canadensis Leaf and 172.510
herb
Estragon Artemisia dracunculus Herb Aromatic spicy, anisic GRAS (182.20)
(Tarragon)
Eucalyptus Eucalyptus globulus Leaf Lighly aromatic, 172.510
and other spp. cineolic
Fennel, bitter Foeniculum vulgare, Seed, herb Sharply warm, GRAS (182.10)
several varieties camphoraceous,
anisic
Fennel, sweet Foeniculum vulgare Seed, herb Sweet, spicy, anisic GRAS (182.10,
var. dulce 182.20)
Fenugreek Trigonella foenum- Seed (Extract-bitter, GRAS (182.10,
graecum celery-like, spicy) 182.20)
Fig Ficus carica Leaf (Extract -sweetly
green, herbaceous)
Fir Abies balsamea and Needles Sweetly piny, balsamic 172.510
otherspp. twigs
Galangal Alpinia galanga Rhizome Spicy, ginger-like, greater-172.510
(greater) cineolic (A.B.)
Alpinia officinarum
(lesser) Jesser-GRAS
(182.20)
Galbanum Farula galbaniflua and Gum resin 172.510
otherspp.
 Plant Materials Used in Flavorings 371

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Gambir (Catechu, Uncaria gambir Extract of Very astringent 172.510

pale) (Qurouparia leaf
gambir)
Garlic Allium sativum Bulb Characteristically
alliaceous, pungent
Genet Spartium junceum Flower 172.510
Gentian Gentiana lutea Rhizome Bittersweet 172.510
Gentian, stemless Gentiana acaulis Rhizome Bittersweet 172.510 (A.B.)
Geranium Pelargonium Leaf Sweetly rosy GRAS (182.10,
capitatum 182.20)
Geranium, East Cymbopogon martini Leaf (Essential oil)
Indian GRAS (182.20)
Geranium, rose Pelargonium Leaf Sweetly aromatic, (Essential oil)
graveolens rose-like GRAS (182.10,
182.20)
Germander Tenerium chamoedrys 172.510 (A.B.)
chamaedrys
golden- T. polium
GhattiGum Anogeissus latifolia Gum GRAS
(Dhaoa) and other spp.
Ginger Zingiber officinale Rhizome Lemony, aromatic, GRAS (182.10,
mildly pungent 182.20)
Ginkgo Ginkgo biloba Nut
(Maidenhair
tree)
Glycyrrhiza Glycyrrhiza glabra Root Characteristically GRAS
(Licorice) and other spp. sweet
Grains of paradise Aframonum Seed Hot, peppery, GRAS (182.10)
(Melegueta melegueta cardamom-like
pepper)
Grapefruit Citrus paradisi Fruit, peel Fresh, citrus like odor
Ground ivy Glechoma hederacea Mint-like
(Alehoof)
Guaiacwood Guaiacum officinale, Gum-oleo Violet, tea-like 172.510
(Lignum vitae) G. santum, Bulnesia Resin
sarmienti
Guarana Paullinia cupana Paste of 172.510
(Brazilian cacao) crushed
seeds
Guava Psidium spp. Fruit Sweet, aromatic GRAS (182.20)
Hamamelis (Witch Hamamelis virginiana Leaf Mildly aromatic,
hazel) astringent
Haw, black Viburnum Bark 172.510
prunifolium
Hemlock (Spruce) Tsuga canadensis Needles Extract: astringent 172.510
T. heterophylla twigs Oil: agreeably sweet,
piny
Hickory Caryaspp. Bark Used for smoking GRAS (182.20)
meats, etc.
Hops Humulus lupulus Female Penetrating, aromatic, (Oil) GRAS
flower bitter (182.20)
Horehound Marrubium vulgare Herb Aromatic GRAS (182.10,
182.20)
Horsemint Monada punctata Herb Strongly thyme-like (Oil) GRAS
(182.20)
372 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A.a

Horseradish Armoracia rusticana Root Intensely pungent, GRAS (182.10)

A. lapthifolia aromatic
Horseradish Tree Moringa oleifera Leaf Curry-like, pungent
Hyacinth Hyacinthus orienta/is Flower Sweetly floral, green 172.510
Hyssop Hyssop us officina/is Herb Bitter, minty, warmly GRAS (182.10,
pungent 182.20)
Iceland moss Cetraria islandica Thallus Aromatic, bitter tonic
Immortelle Helichrysum Flowering Intense, pleasant GRAS (182.20)
Augustifolium tops sweet odor
Imperatoria Peucedanum Rhizomes Tonic-like 172.50
ostrithium Koch
(Imperatoria
ostruthium)
Iva Achillea moschata Leaf Warmly herbaceous, 172.50 (A.B.)
camphoraceous
Jaborandi Pilocarpus jaborandi Leaf Sweetly herbaceous
Jasmine Jasminum officinale Flower Characteristically (Essential oil)
and other spp. floral GRAS (182.20)
Juniper Juniperus communis Berry Richly warm, bitter, (Essential oil)
piny GRAS (182.20)
Kola Cola acuminata Nut Astringent (Extract) GRAS
(182.20)
Kuromoji Lindera sericea Leaf Aromatic, warmly
spicy
Labdanum Cistus ladaniferus Resinous Sweetly herbaceous, 172.50
exudate balsamic
Laurel (Sweet Laurus nobilis Leaf Fresh, sweet cineolic GRAS (182.20)
bay) Berries
Lavan din Lavandula hybrids Flower Fresh, (Essential oil)
camphoraceous, GRAS (182.20)
woody, herby
Lavender Lavandula officina/is Flower GRAS (182.10,
182.20)
Lavender, spike Lavandula latifolia Flower GRAS (182.20)
Leek Allium porrum Fleshy Onion-like but milder
leaves and sweeter
Lemon Citrus limon Fruit, peel Sour, bitter taste GRAS (182.20)
Lemongrass Cymbopogon citratus Grass Fresh, grassy, lemon- (Essential oil)
C. flexuosus like GRAS (182.20)
Lemon-verbena Lippia citriodora Herb Fresh, lemon-like, 172.50 (A.B.)
fruity
Licorice Glycyrrhiza glabra Root Sweet, caramel-like GRAS
(Glycyrrhiza)
Lime Citrus aurantifolia Leaves, Fresh citrus aroma GRAS 182.20
unripe
fruit
Lime (Linden) Tilia vulgaris, Flower Fragrant GRAS (182.20)
T. europaea Leaf Leaf: 172.510
in alcoholic
beverages only
Linaloe wood Bursera delpechiana Wood Flowery, rose-like 172.510
and other Bursera odor
spp.
Linden Tilia spp. Flowers Soothing, aromatic GRAS (182.10)
flavor
 Plant Materials Used in Flavorings 373

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A.•

Linden leaves Tilia spp. Leaves Soothing, aromatic 172.510 (A.B.)

flavor
Lovage Levisticum officinale Herb Sweet, yeasty, musky, 172.510
Root lemon-like, celery-
like
Locust Ceratonia siliqua Bean Sweetly nutty (Extract) GRAS
(182.20)
Lungmoss Sticta pu/monaria Leaf Medicinal 172.510
Lungwort Pulmonaria officina/is Leaf Medicinal 172.510
Lupulin Humulus lupulus Female Bitter, tonic flavor GRAS (182.20)
flower
catkins
Mace Myristica fragrans Aril Nutmeg-like, spicy GRAS (182.10,
182.20)
Maidenhair Adiantum capillus- Fern Bitter-sweet, acidic 172.510 (A.B.)
veneris
Maguey Agave atrovirens Leaf Tequila
Malt Hordeum vulgare and Extract (Extract) GRAS
other cereal grains
Maple, mountain Acer specatum 172.510
Marigold, pot Calendula officina/is Flower Penetrating, aromatic, GRAS (182.10)
bitter
Marjoram, pot Majorana onites Herb Sharply aromatic, GRAS (182.10)
camphoraceous
Marjoram, sweet Majorana hortensis or Herb Thyme-like, GRAS (182.10,
Origanum majorana camphoraceous, 182.20)
balsamic
Mate 1/ex paraguariensis or Leaf Stimulent (Extract) GRAS
Yerbasanta (182.20)
Melilotus (Sweet Melilotus officina/is Herb Coumarin-like,
clover) vanilla-like
Mandarin Citrus reticulata Leaves, Orange like odor GRAS (182.20)
fruits,
rind
Mastic Pistacia spp. Gum resin Aromatic, balsamic,
bitter
Menthol Menthaspp. Flowering Fresh, strong menthol GRAS (182.20)
tops odor
Menthyl acetate Menthaspp. Flowering Cool mint flavor GRAS (182.20)
tops
Mignonette Reseda odorata Flower Strongly floral, slightly
phenolic
Milfoil (Yarrow) Achillea mi/lefolium Balsamic, spicy, bitter
Mimosa (Black Acacia decurrens var Flower Violet-like, anisic 172.510
wattle) dea/bata
Mints:
Cologne mint Mentha citrata Flowering GRAS
Corn mint M. arvensis tops and
Horse mint M. longifolia leaves
Peppermint M. piperita
Round mint M. rotunifolia
Spearmint M. viridis or
M. spicata
Water mint M. aquatica
374 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Molasses Saccarum officinarum Byproduct Sweet burnt taste GRAS 182.20

of sugar
refining
Mullein Verbascum Flower Pleasantly bitter 172.510 (A.B.)
phlomoidea,
V. thapsiforme
Mushroom Agaricus campestris,
A. arvensis and
many other edible
spp.
Musk (Ambrette) Hibiscus abelmoschus Seed Musk-like GRAS
Mustards:
Black Brassica nigra Seed Characteristically GRAS (182.10,
pungent 182,20)
Brown B.juncea GRAS
White Sinapis alba GRAS (182.10)
Myrrh Commiphora molmol, Gum resin Balsamic, bitter 172.510
C. abyssinica and
otherspp.
Myrtle Myrtus communis Leaf Spicy, refreshing 172.510 (A.B.)
Narcissus Narcissus poeticus Flower Fragrant
Naringin Citrus paradisi Blossoms, Bitter GRAS (182.20)
flavedo
Nasturtium Tropaeolum majus Seed, leaf Mildly pungent, caper-
like
Nepeta (Catnip) Nepeta cataria Flower Minty
Neroli, Bigarade Citrus aurantium Flower Sweetly floral (Essential oil)
GRAS (182.20)
Nettle Urtica dioica Leaf Spinach-like
Nigella (Black Nigel/a sativa Seed Peppery, cubeb-like
cumin)
Nutmeg Myristica fragrans Seed Warmly spicy, terpeny GRAS (182.10,
182.20)
Nuts:
Chestnut Castanea sativa
Hazelnut Corylus ave/lana
Walnut Juglans regia
Oak, English Quercus robur Wood 172.510in
alcoholic
beverages only
Oak moss Evernia pumastri, Plant 172.510 thujone
E. furfuracea and free
otherspp.
Oak, white, chips Quercus alba L. Chips Astringent 172.510
Olibanum Boswellia carteri and Gum Agreeably balsamic, 172.510
otherspp. exudate lemony
Olive Olea europea Fruit Mildly distinctive GRAS
Onion Allium cepa Bulb Sweetly alliaceous, GRAS (182.20)
lachrymatory
Opopanax Opopanax chironium, Oleo gum Unpleasant, bitter 172.510
Commiphora Resin Acrid
erythraed var.
glabrescens
Orange, bitter Citrus aurantium Flowers, Orange aroma, bitter GRAS (182.20)
peel flavor
 Plant Materials Used in Flavorings 375

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A.a

Orange, sweet Citrus sinesis Leaf, Astringent flavor, GRAS (182.20)

flowers, characteristic aroma
peel,
fruit
Oregano (Mexican Lippiaspp. Herb Camphoraceous, GRAS (182.10)
sage) thyme-like
Oregano (Wild Origanum vulgare Herb Sharply penetrating, GRAS (182.20)
marjoram) camphoraceous,
thyme-like
Orris Iris pallida, Rhizome Violet-like Sweetly 172.510
I. germanica floral
Palmarose Cymbopogon martini Grass Sweetly floral, rosy (Essential oil)
GRAS (182.20)
Pansy Viola tricolor Flower 172.510 (A.B.)
Pandanus Pandanus Flower Floral, hyacinth-like
odoratissimus Leaf
Paprika Capsicum annuum Fruit Sweetly distinctive, GRAS (182.10,
slightly pungent 182.20)
Parijata Nyctanthes arbortristis Flower Fragrant, jasmin-like
Parsley Petroselinum crispum Herb Seed Pleasantly aromatic, GRAS (182.10,
P. hortense, bitter 182.20)
P. sativum
Passion flower Passiflora incarnata Flower Fragrant 172.510
Patchouly Pogosternum cablin, Leaf Persistent, woody, 172.510
P. heyheanus balsamic
Peach Prunus persica Leaf 172.510 (A.B.,
Not to exceed
25 ppm prussic
acid in plavor)
Kernel Bland oil GRAS (182.40)
Peanut Arachis hypogea Nut GRAS (182.40)
Pennyroyal:
European Mentha pulegium Herb Bitter sweet, sharply 172.510
American Hedeoma pulegoides minty
Pepper:
Black & white Piper nigrum Fruit Aromatic, spicy, GRAS (182.10,
pungent 182.20)
Cayenne Capsicum frutescens, Fruit Very pungent GRAS (182.10)
C. annuum
Red C. annuum Fruit Pungent GRAS (182.10)
Long Piper longum or Fruit Aromatic, pungent
P. retrofractum
Peppermint Mentha piperita Flowering Strongly minty, GRAS (182.10,
top Leaf cooling 182.20)
Persic oil Prunusspp. Kernel Intense, almond-like GRAS 182.40
cherry aroma
Peruvian balsam Myroxylon pereirae Balsam Aromatic, warm, (Essential oil)
bitter GRAS (182.20)
Petitgrain Citrus aurantium and Leaf Sweetly citrus (Essential oil)
otherspp. GRAS (182.20)
Pimento (Allspice) Pimenta officina/is Berry Leaf Strongly clove-like, GRAS (182.20)
pungnet
Pimpinella Pimpinella saxifraga, Root Tenaceous, sweet,
P. magna woody, balsamic
 376 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Pine:
Dwarf Pinus nigra var. Needles+ 172.510
pumil/o twigs
Scotch P. syvestris Needles+
twigs
White P. palustris Oil
Pine nut Pinus pinea and other Fruit
spp.
Pine, white, bark Pinus strobus Bark 172.510 (A.B.)
Pipsissewa Chimaphila umbel/ata Leaf (Essential oil)
GRAS (182.20)
Pistachio Pistacia vera Nut
Pomegranate Punica granatum Bark, Agreeable, acid flavor GRAS (182.20)
edible
fruit pulp
Poplar Populus balsamifera Bud 172.510 (A.B.)
and other spp.
Poppy Papaver somniferum Seed Slightly nutty GRAS (182.10)
Pot Marigold Calendula officina/is Flowers Herbaceous odor, GRAS (182.10)
bitter
Pot Marjoram Majorana onites Leaves, Sweetly aromatic GRAS (182.10)
shoots
Prickly ash Xanthoxylum Bark (Extract) GRAS
americano, (182.20)
X. clavaherculis
Purslane Portulacca oleracea, Herb Fresh, succulent,
P. sativa cooling
Quassia Picrasma excelsa Wood Intensely bitter 172.510
Quebracho Aspiosperma Bark Color; astringent 172.510
quebracho-blanco,
Schinopsis lorentzi
Quillaia (Soap Quillaja saponaria Bark
bark)
Quince Cydonia oblonga, Seed GRAS (182.40)
C. vulgaris
Racombole Allium Bulb Alliaceous
(Spanish garlic) scorodoprasum
Raspberry Rubus idaeus Leaf Medicinal
Red Saunders Pterocarpus sanalinus Wood 172.510 (A.B.)
(Red
Sandalwood)
Rhatany Krameria triandra, Root Bitter, acidic, 172.510
K. argentea astringent
Rhubarb Rheum officinale and Root Bittersweet, tart, 172.510
other spp. except aromatic
Chinese rhubarb
(R. rhaponticum)
Rhubarb, garden Rheum rhapontieum Rhizomes, Bitter-tonic flavor 172.510 (A.B.)
root root
Rose Rosa alba and other Flower Sweetly floral (Essential oil)
spp. GRAS (182.20)
Hips Sour GRAS (182.20)
Leaf Herbaceous (Extract) GRAS
(182.20)
 Plant Materials Used in Flavorings 377

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Rose geranium Pelargonium Leaf Floral, rose-like (Essential oil)

graveolens GRAS (182.20)
Roselle (Jamaica Hibiscus sabdariffa Calices Color 172.510 (A.B.)
sorrel) Fruit
Rosemary Rosmarinus officina/is Herb Light, camphoraceous, GRAS (182.10,
cineolic, piny 182.20)
Rosin (colophony) Pinus palustris and Oleo gum Pungent, bitter 172.510 (A.B.)
other Pinus spp. resin
Rowan Sorbus ancuparia Berry Acidic
Rue Ruta graveolens Herb Strongly aromatic, GRAS
bitter
Safflower (Bastard Carthamus tinctorius Flower Color
saffron)
Saffron Crocus satica Stigma Color; aromatic, GRAS (182.10,
iodine-like 182.20)
Sage:
Dalmatian Salvia officina/is Herb Aromatic, herbaceous, GRAS (182.10,
cineolic 182.20)
Greek Salvia triloba GRAS (182.10,
182.20)
Spanish S. lavandulaefolia GRAS (182.10,
182.20)
St. John's bread Ceratonia siliqua Fruit Sweet (Extract-GRAS)
(182.20)
St. Johnswort Hypericum Leaves, Aromatic balsamic 172.510
perforatium flowers, odor Hypericin-
cautis free alcohol
distillate
formente
(A.B.)
Samphire Crithmum maritimum Plant Pleasantly spicy
Sandalwood Santalum album Wood Sweetly aromatic 172.510
Sandarac Tetraclinis articulata, Oleo-resin Balsamic, turpentine- 172.510 (A.B.)
or Callitris exudate like
quadrivalvis
Sarsaparilla:
Mexican Smilax Root Very little flavor 172.510
aristolochiaefolia
Honduras S. reglii
Ecuador S. febriguga and other
spp.
Sassafrass Sassafras officina/is, Leaf Aromatic, anisic, 172.510 safrole-
S. albidum bitter, astringent free Essential
oil is NOT
permitted
Savin Summitates sabinae Juniper-like, bitter,
camphoraceous
Savory Satureja hortensis Herb Sharply GRAS (182.10,
(summer) camphoraceous, 182.20)
S. montana (winter) spicy
Schinus molle Schinus moUe Fruit Spicy, peppery (Essential oil)
(California GRAS (182.20)
pepper)
Senna. Alexandria Cassia acutifolia Leaf Faintly bitter, 172.510
purgative
378 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Serpentaria Aristolochia Root 172.510 (A.B.)

(Virginia serpentaria
snakeroot)
Sesame (Benne Sesamum indicum Seed Fatty, bland GRAS (182.10)
seed)
Shallot Allium ascalonicum Bulb Mildly alliaceous
Simaruba Simaruba amara Bark Bitter 172.510 (A.B.)
Sloe (Blackthorn) Prunus spinosa Berry GRAS (182.20)
Snakeroot, Asarum canadensis Root Bitter, acidic, 172.510
Canadian camphoraceous
Sorrel Rumex acetosa Leaf Sharply acidic
Southernwood Artemisia abrotanum Wood
Soy Glycine soja, Soya Bean Characteristically
hispida mealy, fatty
Spearmint Mentha spicata, Herb Minty GRAS (182.10,
M. viridis 182.20)
Spike Lavender Lavandula latifolia Flower Sweetly cineolic (Essential oil)
GRAS (182.20)
Spoonwort Cochlearia officina/is Herb Sharply pungent,
mustard-like
Spruce Abies alba and other Needles, Herby, balsamic 172.510
spp. Twigs
Star Anise Illicium verum Fruit Bitter, anisic, licorice- GRAS (182.10)
like
Storax (Styrax) Liquidambar Balsam Balsamic, cinnamic 172.510
orienta/is
L. styracifiua
Sumbul Ferula sumbul Root Warm, woody, orris-
(Spikenard) like, musky
Sunflower Helianthus annuus Seed Oily
Sweet Cicely Myrrhis odorata Herb Pleasantly green
(Sweet chervil)
Sweet Woodruff Calium odoratum, Herb Bitter, herbaceous
Asperu/a odorata
Tagetes Tagetes patula and Flower Herbaceous, bitter- (Essential oil)
(Marigold) other spp. sweet, fruity 172.510asoil
only
Tamarind Tamarindus indica Fruit Acidic (Extract) GRAS
(182.20)
Tangerine Citrus reticulata Fruits Pleasant, organe-like GRAS (182.20)
odor
Tansy Chysanthemum Leaf 172.510 (A.B.)
vulgare (Tanacetum Finshed
vulgare) Beverage
thujone free
Tarragon Artemisia dracunculus Herb Aromatic, herbaceous, GRAS (182.10,
(Estragon) anisic 182.20)
Tea Thea sinensis Leaf Mildly aromatic, GRAS (182.20)
stimulent
Thistle, holy Carduus benedictus Herb Tonic, bitter 172.510 (A.B.)
Thyme Thymus vulgaris. T. Herb Strongly armoatic, GRAS (182.10,
serpyllum, T. zygis bitter, spicy 182.20)
Thymus capitatus Thymus capitatus Flowering Warm herbaceous 172.510
(Spanish plant odor
"Origanum")
 Plant Materials Used in Flavorings 379

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.S.A."

Tolu Myroxylon balsamum Oleo-resin Sweetly balsamic, 172.510

exudate cinnamic
Tomato Lycopersicon Fruit Characteristic, sweet
esculentum
Triticum Agropyron repens Rhizomes GRAS (182.20)
Tuberose Polyanthes tuberosa Flower Heavy, sweet, floral (Essential oil)
GRAS (182.20)
Truffle:
White Italian Tuber magnatum
Black French T. melanosporum
Red English T. destivum
Winter T. brumale
African Terfezia leonis
Turmeric Curcuma longa Rhizome Color; fresh, spicy, GRAS (182.10,
(Curcuma) curry-like 182.20)
Turpentine Pinus palustris and Essential Characteristic, 172.510
other spp. producing oil balsamic
turpentine
Valerian Valeriana officina/is Root Objectionable odor, 172.510
bitter-sweet
Vanilla Vanilla planifolia, Fruit Characteristically GRAS (182.10,
V. Tahitensis sweet 182.20)
Verbena (Lemon Lippia citriodora Herb Pleasantly aromatic, 172.510 (A.B.)
verbena) (Verbena tryphita) strongly lemon-like
Verbena, Spanish Thymus hiematis Herb Freshly herbaceous,
lemony
Veronica Veronica officina/is Flowering Tonic, slightly bitter 172.510 (A.B.)
tops
Vervain, Verbena officina/is Herb 172.510 (A.B.)
European
Vetiver Vetiveria zizanoides Rootlets Aromatic, woody, 172.510
earthy, bitter
Violet Viola odorata Flower, Characteristic (Absoluter)
leaf GRAS (182.20)
Violet, Swiss Viola calcarata Flowers, Pleasant floral odor, 172.510
leaves bitter
Walnut Juglans species Leaf, Aromatic, pungent, 172.510
unripe bitter, nutty
fruit
Watereress Nasturtium officinale Leaves Fresh, green, slightly
pungent
Wild cherry Prunus serotina Bark Benzaldehyde (Extract) GRAS
(182.20)
Wintergreen Gaultheria Leaf Fragrant, sweet,
procumbens root beer-like
Witch hazel Hamamelis virginiana Leaf Faintly tobacco-like,
astringent
Woodruff, sweet Aspervia odorata Herb Coumarin-like 172.510 (A.B.)
Wood sorrel Oxalis acetosella Herb Green, acidic, bitter
(Shamrock)
Yarrow Achillea millefolium Herb Balsamic, spicy, bitter 172.510 (A.B.
Finished
Beverage
thujon free)
Yerba Santa Eriodictyon Herb 172.510
californium
380 Source Book of Flavors

Regulatory
Common Name Botanical Source Part Used Sensory Character Status in U.s.A.•

Ylang-ylang Cananga odorata Flower Sweetly floral, intense (Essential oil)

GRAS (182.20)
Yucca Yucca brevifolia, Leaf 172.510
Y. schidigera
Zdravetz Geranium Flower Sweetly woody, floral,
macrorrhizum tobacco-like
Zedoary Curcuma zedoaria Bark Warmly spicy, GRAS (182.10,
camphoraceous 182.20)
a Explanation of the status numbers will be found at the end of the table.
FFPA-Free from Prussic Acid
A.B.-Alcoholic Beverage usc only
Sources:
Arctander, S. 1960. Perfume and Flavor Materials of Natural Origin. Elizabeth: S. Arctander.
Budavari, S., O'Neil, M.J., Smith, A., and Heckelman, P.E. 1989. The Merck Index, Eleventh Edition. Rahway, N.J.: Merck &
Co.
CFR- 1990. Code of Federal Regulations. Washington, D.C.: US Government Printing Office.
Farrell, K.T. 1990. Spices, Condiments, and Seasonings. 2nd ed. New York: Van Nostrand Reinhold
Guenther, E. 1948-52. The Essential Oils, Vol. I-IV. New York: Van Nostrand Co.
Heath, H.B. 1981. Source Book of Flavor. New York: A VI.
Prakash, V. 1990. Leafy Spices. Boca Raton, Fla.: CRC Press.

182.10 Spices and Other Natural

DEFINITION OF STATUS
172.510 Natural Flavoring Substances and
Natural Substances Used in Conjunction
with Flavors
Natural flavoring substances and natural
adjuvants may be safely used in food in
accordance with the following conditions:
A. They are used in the minimum
quantity required to produce their
intended physical or technical
effect and in accordance with all
the principles of good manufactur-
ing practice.
B. In the appropriate forms (plant
parts, fluid and solid extracts,
concretes absolutes, oils, gums,
balsams, resins, oleoresins, waxes,
and distillates) they consist of
one or more of the following,
used alone or in combination with
flavoring substances and adjuvants
generally recognized as safe in
food, previously sanctioned for
such use, or regulated in any section
of this part.
Seasonings and Flavorings
Spices and other natural seasonings and
flavorings that are generally recognized
as safe for their intended use, within the
meaning of section 409 of the Act (see table).
182.20 Essential Oils, Oleoresins
(Solvent-Free), and Natural Extractives
(Including Distillates)
Essential oils, oleoresins (solvent-free),
and natural extractives (including dis-
tillates) that are generally recognized as
safe for their intended use, within the
meaning of section 409 of the Act (see table).
182.40 Natural Extractives (Solvent-
Free) Used in Conjunction with Spices,
Seasonings, and Flavorings
Natural extractives (solvent-free) used in
conjunction with spices, seasonings and
flavorings that are generally recognized
as safe for their intended use, within the
meaning of section 409 of the Act (see table).
 Chapter 9
Principal Essential Oils
Used in Flavorings

Avg Regula-
Yield of tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Allspice (pimento) Fruits of Pimenta West Indies July- 3-4.5 Eugenol GRAS
dioica L. (Jamaica) Aug.
Ambrette Seeds of Hibiscus Java, 0.2-0.6 Farnesol GRAS
abelmoschus L. Martinique ambrettolide
Angelica Root and seeds of Europe July Root: 13 •Phellan- GRAS
Angelica archangelica (Germany, 0.3-1 drene
L. France) Seeds:
0.6-1.5
Angostura Bark of Galipea South America 1-2 GRAS
officina/is (DC.) Hancock (Venezuela)
Anise Fruits of Pimpinella Europe, Aug.- 1.5-4 Anethol GRAS
anisumL. U.S.S.R. Sept.
Artemisia Herbaceous tops of Central Aug. 0.3-0.4 Thujone Goodmfg
Artemisia absinthium Europe, Asia, practice-
L. North thujone
America free
Asafetida Oleo-gum-resin Iran July 7-9 Disulfides GRAS
from Ferula asa- Afganistan
foetida L. and
related spp.
BalmOemon Herbaceous tops of Southern and Aug. 0.1 Geraniol, GRAS
balm) Melissa officmalis central citronellol,
L. Euro~e, citra!
Nort
Africa
Balsam Peru Oleoresin from EISalvador Nov. 45-55 Benzyl cinna- GRAS
Myroxylon pereirae to June from the mate, benzyl
Klotzsch. extracted benzoate
balsam
Basil, sweet Herbaceous tops of Mediterra· Sept. 0.1 Methyl chavi- GRAS
Ocimum basilicum L. nean, U.S.A. col,linalool,
Several varieties cineol
are distilled:
Reunion-type Malagasy
Republic

381
 382 Source Book of Flavors

Avg Regula-
Yield of tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Methyl cinnamate- Bulgaria,
type Haiti
Eugenol-type Java, U.S.S.R.
Bay laurel Leaves of La urus Mediterra- Se~. 0.5-1 Cineol GRAS
(Sweet bay) nobilis L. nean to ar.
Bay, West Indian Leaves of Pimenta West Indies Jan. 1-2 Eugenol GRAS
racemosa (Mill.) J. W. (Dominica), to June
Moore (formerly Venezuela
Myrcia acris Wright
Bergamot Peels of Citrus Calabria Dec. approx0.5 Linalyl esters GRAS
(Bergamot orange) bergamia Risso or <Italy) to Mar.
C. aurantium L.
subspecies
bergamia Wright
andArn.
Birch bark Bark of Betula Canada, Oct. 0.5 Methyl
(Sweet birch) lenta L. U.S.A., to Apr. salicylate
eastern
Europe,
U.S.S.R.
Bitter almond Partially deoiled U.S.A., 0.5-0.7 Benzaldehyde GRAS
press-cake from Middle East, (oil is treated free from
the kernels of southern to remove HCN
Prunus amygdalus Euro~, HCN)
Batsch var. amara Nort Africa
Bois de Rose WoodofAniba South America Jan. 0.7-1.2 Linalool GRAS
rosaeodora Ducke. (Brazil, Peru, to June
Guiana)
Buchu Leaves of Barosma South Africa 0.8-3.5 Diosphenol Good
betulina Bartl and depending mfg
Wendl;B. crenulata on species practice
(L.) Hook.; or B.
serratifolia Willd.
Cacao Fermented and roasted Central and approx Linalool GRAS
seeds of Theobroma South 0.001
cacao L. America,
Africa
Camomile Flowers of Europe, Asia, May to 0.3-1 Chamazulene GRAS
(German chamomile) Matricaria U.S.A., July
chamomilla L. Australia
Camomile Flowers of Anthemis Europe July to 0.3-1 GRAS
(Roman or nobilis L. Oct.
English chamomile)
Camphor, tree WoodofCinnamomum Far East Camphor and
camphora (L.) Eberm. (China, linaloolde-
Taiwan, pending on
Japan) variety
Cananga Flowers of Cananga Islands in Oct. 0.5-1 Sesquiterpene GRAS
odorata Hook. and Indian to alcohols
Thoms. Ocean, Dec.
Java
Caraway Fruits of Carum Europe Aug. 3-6 Carvone GRAS
carvi L. (Holland, to
Hungary), Sept.
North
America
 Principal Essential Oils Used in Flavorings 383

A'l
Yiel of
Regula-
tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Cardamom Seeds of Elettaria India, India: approx 5 Cineole,d- GRAS
cardamomum Maton. Guatamala Aug. a-terpineol,
to terpinyl
Oct. acetate
Guata-
mala: 3-6
Jan.
Carrot Seeds of Daucus France Sept. 0.4-0.8 Carotol GRAS
carota L.
Cascarilla Bark of Croton Bahamas 1.5-3 GRAS
eluteria Bennett
Cassia, Chinese Bark of Cinnamomum South-east June- approx0.3 Cinnamic GRAS
cassia Blume. China July aldehyde
Cedar, white Leaves and twigs of U.S.A., Apr. to 0.6-1 a-Pinene, Goodmfg
(Thuja) Thuja occidentalis Canada, Nov. thujone practice-
L. Japan thujone
free
Celery seed Fruits of Apium France, Sept. 1.5-2.5 d-Limonene, GRAS
graueolens L. Holland, sedanolide
Hungary,
India
Cherry, wild bark Bark of Prunus Canada, GRAS
serotina Ehrh. or U.S.A., (mainly
P. canadensis Poiret. Europe as ex-
tract)
Chervil Herbaceous tops of Southern GRAS
Anthiscus cerefolium EurAe,
(L.)Hoffm. u.s..
Cinnamon bark, Bark of Cinnamomum Sri Lanka July- 0.5-0.8 Cinnamic GRAS
Ceylon zeylanicum Nees. Aug. and aldehyde
Dec.-
Jan.
Cinnamon bark Bark of China, 0.5-3 Cinnamic GRAS
(Cassia) C. cassia Blume, Saigon, depen~ng aldehyde
C. loureirii Nees, Batavia onspec1es
C. burmanni Blume
Cinnamon leaf, Leaves of Cinnamom um Sri Lanka July to 0.5-0.7 Eugenol GRAS
Ceylon zeylanicum Nees. Sept.
Citronella, Fresh or dried herb Sri Lanka Three approx0.5 Geraniol, GRAS
Ceylon Cymbopogon nard us crops per ci tronellal
Rendle year
Citronella, Fresh herb Java 3-4 approx0.7 Geraniol GRAS
Java Cymbopogon crops per ci tronellal
winterianus Jowitt. year
Clove bud Unopened buds of Tanzania, Through-14-21 Eugenol GRAS
Eugenia caryophyllata Malagasy out the
Thunb. Republic, year
East Indies
Clove leaf Leaves of Eugenia Tanzania, 1.5-2 Eugenol GRAS
caryophyllata Malagasy
Thumb. Republic,
East Indies
Clove stem Stems of Eugenia Tanzania, approx5 Eugenol GRAS
caryophyllata Mal:1asy
Thunb. Repu lie,
East Indies
Clover Flowers of Europe, 0.005-0.0~ GRAS
Trifolium spp. central Asia
 384 Source Book of Flavors

A1
Yiel of
Regula-
tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Cognac oil Wine lees and dregs France 0.04-0.1 So-called GRAS
of pressed grape skins depending ethyl
on source aenanthate
Coriander Fruits of Coriandrum North Africa, Sept. 0.1-1 Linalool GRAS
sativumL. Russia,
India
Cubeb Unripe berries of Indonesia, tl!r.- approx 13 Cineole Good
Pipercubeba L. Africa ay mfg
practice
Cumin (cummin) R~fruitsof Mediterranean Sept. approx2.5 Cuminic GRAS
uminum cyminum L. countries, aldehyde
India, ·
U.S.S.R.
Davana Flowers of Southern tl!r.- 0.1-0.6 Good
Artemisia pollens India ay mfg
Wall. practice
Dill (seed) Fruits of Anethum Europe Sept. 2.5-4 Carvone GRAS
graveolens L. Pakistan,
U.S.A.
Dill(weed) Green fruiting tops Eastern July 0.3-1.5 Carvone GRAS
ofAnethum
graveolens L. 1
Euro e.
u.s..
Dill, Indian Fruits of Anethum India 1.2-3.5 Carvone, Good
sowa Roxb. or limonene, mfg
Peucedanum graveolens dillapiol practice
Benth. & Hook.
Elder flowers Flowers of Sambucus Hungary, June GRAS
canadensis L. and Germany,
S.nigraL. France
Elemi Resin from Conarium Phillipines June to 20-30from Good
commune L. or C. Oct. the crude mfg
luzonicum Mig. resin practice
Erigeron Herbaceous tops of Canada, July to 0.3-0.6 Terpinyl Good
Erigeron canadensis U.S.A., Nov. acetate mfg
L. southern practice
Europe
Estragon Herbaceous tops of Central and July- 0.3-1.5 Methylcha- GRAS
(tarragon) Artemisia dracunculus eastern Aug. vicol (estra-
L. Europe gole)
anethol
Eucalyptus Leaves of Euca~ptus sy,ain, 0.75-1.25 Cineole Good
globulus Labi . ortugal, mfg
and many other Brazil, practice
Eucalyptus spp. Zaria
Fennel, sweet Fruits of Foeniculum Germany, Sept. 4-6 Anethol GRAS
vulgare Mill. var. Romania,
dulce U.S.S.R.,
North Africa,
India
Fir(pine) Needles, twigs and U.S.S.R., approx0.3 Good
cones of: North mfg
Siberian fir America practice
(Abies sibirica Lebed); Europe,
Silver fir Japan
(A. alba Mill.);
Japanese fir
(A. sachilenensis,
Masters or A. mayriana
Miyabe & Kudo)
 Principal Essential Oils Used in Flavorings 385

Avg Regula-
Yield of tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Galangal Rhizomes of China 0.5-1 GRAS
Alpinia officinarum
Hance.
Galbanum Dried gum-resin from Iran, 10-22 Good
Ferula galbaniflua Turkestan from the mfg
Boiss & Buhse and crude resin practice
other Ferula spp.
Garlic Bulbs of Allium U.K., 0.1-0.25 Allyl sulfides GRAS
sativumL. Italy,
Egr.;t,
U ..A.
Geranium Leaves and stems of Reunion, Mar. to 0.15-0.2 Geraniol, GRAS
Pelargonium North Africa, Oct. from fresh citronellol
graveolens L'Her. Central and ~epend- material
and other Pelargonium Western mgon
spp. Europe region
Ginger Rhizomes of Zingiber Jamaica, Jamaica: 0.25-1.25 Zingiberene, GRAS
officinale Roscoe West Africa, Febr.- citral
India, Mar.
China,
Australia
Grapefruit Peel of Citrus U.S.A., GRAS
paradisi Macf.; East Africa,
fruit by cold West Indies,
expression Brazil
Guaiac Wood of Guaicum South America, approx5 Guaiol Good
officinale L.; Jamaica, much lower mfg
G. sanctum L.; or Cuba in local practice
Bulnesia sarmienti field stills
Lor.
Hemlock (spruce) Needles and twigs of North America, a- andtl- Good
Tsuga canadensis (L.) China, Pinenes mfg
Carr.j T. heterf!phylla Japan (terpenes practice
(Raf. S?2;.; Picea 0.45%),
glauca ( oench) Voss.; bornyl
or P. mariana (Mill.) acetate
B.S.P.
Hops Flower catkins of Europe, Sept. 0.3-0.5 Myrcene, GRAS
Humulus lupulus L. North humulene
America
Horsemint Herbaceous tops of U.S.A. 1-3 Thymol GRAS
(monarda) Monarda punctata (0.60%)
L.
Hyssop Herbaceous to~ of Southern Aug. 0.1-0.3 a-Pinene, GRAS
Hyssopus officina lis Europe sesquiter-
L. pene
illcohols
lmmortelle Flowering tops of Mediterranean <0.1 Nerol, GRAS
Helichrysum countries nerylacetate
angustifolium DC. (Yugoslavia)
Jasmine Flgwers of Jasminum Mediterranean June to 3%of Nerol, GRAS
r:f.!icinale L. or countries, Sept. concrete ~erpineol,
. grandiflorum L. Asia containing Jasmone
40-50
essential
oil
Juniper berry Berries of Juniperus Europe (Italy) Aug.- 0.5-0.6 a-Pinene GRAS
communisL. Asia, Sept. up to 2.5
North from dried
America berries
 386 Source Book of Flavors

Avg Regula-
Yield of tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Laurel Leaves of Laurus Mediter~anean Se~. 0.5-1 Cineole GRAS
(sweet bay) nobilis L. countnes to ar.
Labdanum Gum resin from the Spain, July- 1-2from Good
leaves and twigs of Cyprus Aug. the gum mfg
Cistus tadaniferus resin practice
L. and other Cistus
spp.
Lavan din Floweri~ tops of Southern Aug. 0.5-1 Linalyl
Lavan uta hybrida France acetate
Rev. being a h~brid (20-22%)
of L. tatifolia ill.
andL. officinalis
Chaix.
Lavandin (Abrialis Flowering tops of Southern Aug. 0.5-1 Linalyl
type) a selected strain France acetate
of L. hybrida Rev. (30-32%)
Lavender Flowering tops of Mediterranean July- 0.5-1 Linalool, GRAS
Lavanduta officinalis countries, Aug. linalyl
Chaix. U.K., acetate
North Africa
Lavender, spike Floweri~ tops of S~ain, Aug. 0.75-1 Linalool, GRAS
Lavan uta tatifolia (DC.) ranee linalyl
Viii. acetate
Lemon Peel of Citrus limon Italy, Dec. approx4 Limonene GRAS
(L.) Burm. fruit by California, to Apr. (90%), citra!
cold expression Florida, through
Spain, to Oct.
Israel
Lemongrass Herbaceous tops of West Indies, Aug. 0.3-0.4 Citra! (approx GRAS
Cymbopogon citratus Malagasy, 70%)
DC. or Andropogon Guatemala
nard us var. ceriferus
C. ftexuosus (Nees) East Indies, May- 0.2-0.3 Citra!
Stapf. or Andropogon India, June (80-85%)
nard us var. ftexuosus Indonesia,
Sri Lanka
Lemon verbena Leaves and twigs of Europe June to 0.1-0.2 Citra! Good
Lippia citriodora Oct. mfg
H.B.K. practice
in
alcoholic
beverages
only
Lime Peels of Citrus West Indies, Through-approx 0.1 Citra! GRAS
aurantifotia Swingle Mexico, out the
fruit, by cold Florida year
expression, or by
distillation as a
by-product of lime
juice production
Lin aloe Wood of Bursera Mexico Jan. to approx 8 Linalool (60- Good
detpechiana Poiss. May 75%) mfg
and other Bursera practice
spp.
Lovage Rhizomes of Levisticum France, Sept. Fresh: a-Terpineol Good
officinate Koch. Germany, 0.1-0.2 mfg
Czechoslova- Dried: practice
kia 0.5-1
Mace Arilus of the fruits West Indies, Through-4-15 GRAS
of Myristicum East Indies out the
fragrans Routt. year
 Principal Essential Oils Used in Flavorings 387

Avg Regula-
Yield of tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Mandarin Peels of Citrus Italy, approx0.5 Decylalde- GRAS
(tangerine) reticulata Blanco. U.S.A. hyde
fruit, by cold
expression, or by
steam-distillation
Marjoram, sweet Herbaceous tops-of Europe Aug.- 0.2-0.3 Terpen-4-ol, GRAS
Majorana hortensis,(L.) Sept. a-terpineol
Moench.
Mentha arvensis Leaves of Mentha Brazil, Brazil: 0.5-1 Commercial Not
(corn mint) arvensis L. var. Japan, Jan., depending oil 'is partial- permitted
piperascens Holmes China Mar.- on source lyde-men- mU.S.A.
or Mentha arvensis Apr. tholated to a but widely
L. var.glabrata J~an: residual men- used
Holmes. thollevel de- else-
a::5' pending on where
Oct. source
Mustard De-oiled press-cake, U.K., Sept.- 0.6-1.2 Allyl isothio- GRAS
of the seeds of Europe Oct. cyanate
Brassica nigra (L.)
Koch.
Myrrh Oleo-gum-resin from Somalia, 3-Sfrom Good
Comm~hora molmol Ethiopia the gum mfg
Engl.; . abyssinica practice
Engl. and other
Commiphora spp.
Myrtle Leaves of Myrtus Mediterranean July- 0.2-0.3 a-Pinene, Good
communisL. countries Aug. camphene, mfg
cineole practice
Nutmeg Kernels of the fruits East Indies, 6.5-13 a- and,3· GRAS
of Myristica West Indies, depending Pinenes,
fragrans Houtt. Sri Lanka on source limonene,
4-te~ineol,
safro e,
myristicin
Ocimum Herbaceous tops of
Ocimumspp.
Thymol-type:
0. gratissimum; West Africa Thymol
Eugenol-type:
0. gratiss1mum Seychelles, Eugenol
Indonesia,
Brazil,
Onion Bulbs of Allium U.K., 0.005- n-P:lfyl GRAS
cepaL. EurT., 0.01 di fide
u.s ..
Orange, bitter Leaves and twigs Sicily, Petitgrain: Linalyl ace- GRAS
(petitgrain); Spain, approx0.2; tate
flowers (neroli Guinea, neroli:
bigarade) or peel Brazil approx0.1;
of Citrus aurantium peel:
L. subspecies amara 0.4-0.5
L.
Orange, sweet Leaves and Twigs Italy, Spain, 0.4-0.5 Limonene GRAS
(petitgrain), North Africa, (peel) (90%), decyl-
flowers (neroli), or California, aldehyde
peel of Citrus Florida
sinensis L. Osbeck.
or C. aurantium L.
var. dulcis L.
Origanum Herbaceous tops of U.S.S.R., Aug. approx 1 Thymol or GRAS
(wild marjoram) Origanum vulgare Central carvacrol
 388 Source Book of Flavors

A':f:of Regula-
Yiel tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
L.andother Europe, depending
Origanum spp. Italy onsppor
variety
Orris Peeled rhizomes of Italy Peeled 0.2-0.3 Irone, fatty Good
Iris germanica rhizomes acid esters mfg
L. or L pallida are aged practice
Lam. for2yr
Palmarosa Herbaceous tops of Indonesia, Java: Geraniol GRAS
Cymbopogon martini India, every4 (0.90%)
Stapf. var. motia Seychelles months
India:
Oct.
Parsley seed RJ;: seeds of Europe, Sept. 1.5-3.5 Apiol GRAS
etroselinum U.S.A.
sativum Hoffm.
Parsley herb Young green tops U.K., Sept. approx0.05 GRAS
of Petroselinum Hungary,
sativum, Hoffm. Germany,
U.S.A.
Patchouly Leaves of Pogostemon Indonesia, Dec.- 1.5-3 Good
cablin Benth.or MalaJsia, Jan. mfg
P. heyneanus Benth. Braz· practice
Pennyroyal Herbaceous toJ: of U.S.A. May to 0.5-1 Pulegone Good
Hedeoma Uu egioides Sept. mfg
(L.) Pers. American) Mediterranean practice
or Menthapulegium, countries
L. (European)
Pepper, black Dried immature India, Ar1c.and 1-2.7 Terpenes GRAS
berries of Piper Indonesia, ov.
nigrumL. Brazil ~epend-
1ngon
region
Peppermint Flowering tops of U.S.A., Sept. 0.3-0.7 Menthol, GRAS
Menthapiperita L. Italy, depending menthane,
Japan on source menthyl
and variety acetate
Petitgrain Leaves and twigs of
Citrus spp. (q.v.)
Pimento (allspice) Fruits of Pimenta West Indies July- 3-4.5 Eugenol GRAS
dfoica L. (Pimenta Aug. (70-80%)
officinalis Lindl.);
an oil is also
distilled from the
leaves.
Pine, dwarf Needles and twigs of Central 0.3-0.4 a-Pinene Good
Pinus mu(! Turra. Europe mfg
var. pumi eo (Haenke) practice
Zenari
Pine, Scotch Needles and twigs of Europe, Borneol, Good
Pinus sylvestris L. Asia, bornyl mfg
North acetate practice
America
Pine, white Needles and wood of North America a- and(:J- Good
Pinus strobus L. (but of no Pinene mfg
commercial practice
value) m
alcoholic
beverages
only
 Principal Essential Oils Used in Flavorings 389

A'lof Regula-
Yiel tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Rose Flowers, buds and Bulgaria, June Depends Rhodinol (30- GRAS
leaves of Rosa Turkey, on distil- 60%)
damascena Mill., Morocco, lation
R. alba L., R. centifolia France, method
L., R. gallica L. and Italy
var. of these spp.
Rosemary Whole plant or Spain and May to 0.5-1.2 Cineole, GRAS
leaves of Rosmarinus other Sept. borneol
officinalis L. Mediter-
ranean coun-
tries
Sage, Dalmatian Leaves of Salvia Yugoslavia Sept. 0.5-1 Cineole GRAS
officinalis L.
Sage, Greek Leaves of Salvia Greece, Sept. Cineole GRAS
triloba L. Turkey
Sage, Spanish Leaves of Salvia Spain Sept. Cineole GRAS
lavandulaefolia Vahl.
Sandalwood, white Wood from Santalum India My sore: Santalol Good
(East Indian) albumL.or (Mysore) 4.5-6 (90%) mfg
S. spicatum (R.Br.) Australia: practice
and Eucarya spicata Australia 1.4-2.6
(R.Br.) Sprag & Summ.
Sandalwood, West WoodfromAmyris South America, 2.5-3 {j-Caryophyl- Good
Indian balsifera L. Haiti, lene mfg
(amyris) Jamaica practice
Sassafras Root bark and leaves U.S.A., Aug.- 2-3 Safrole Not
of Sassafras Canada Sept. permitted
albidum (Nutt) Nees. mfood
in many
countries
Sassafras, Brazilian Wood from Ocotea Brazil July to 1.2-1.5 Safrole (90%)
aJrubarum, H.B.K. Oct.
0. pretiosa)
Savory, summer Herbaceous tops of Southern July- approx0.1 Carvacrol GRAS
Satureia hortensis Eur'Xe, Aug.
L. u.s..
Savory, winter Herbaceous tops of S~in, Aug. approx0.2 Carvacrol GRAS
Satureia montana orocco,
L. freed from Yugoslavia
woody portions
Schinus Molle Dried berries of Mediterra- Aug. 5-7 {j-Phellan- GRAS
(Californian Schinus molle L. nean coun- drene
or Peruvian pepper) tries
Spearmint Leaves of Mentha North Ameri- Sept. approx.0.6 1-Carvone GRAS
spicata Houds or L. ca,Europe
Spike lavender Floweriji tops of S~ain, Aug. 0.75-1 Linalool, GRAS
Lavan ula lati{olia (DC.) ranee linalyl ace-
Viii. tate
Star anise Fruits (seeds) of China, Through-8-9 Anethole GRAS
Illicium verum Vietnam out the 85-90%)
Hook. year;
max.
Aug.-
Sept.
Storax (styrax) Balsamic exudate Asia Minor 0.5-1 from Good
from Liquidambar the crude mfg
orientalis Mill. balsam practice
(Levant or Asian) Southern
or L. styraciflua L. U.S.A.,
(American) Mexico,
 390 Source Book of Flavors

A':f
Yiel of
Regula-
tory
Principal Main Essential Status
Producing Crop Oil Chief Aromatic in
Common Name Botanical Source Countries Season (%) Constituents U.S.A.
Honduras,
Guatemala
Tagetes Flowering tops of India, 0.3-0.4 Ocimene, Good
(marigold) Tagetes patula L., Southern tagetone mfg
T. erecta L. or Mexico, (50-60%) practice
T. min uta L. (T. South Africa,
gladulifera Schrank) Australia
Tarragon (estragon) Herbaceous tops of Central and July- 0.3-1.5 Methyl chavi- GRAS
Artemisia dracunculus eastern Aug. col (estra-
L. Europe gole), ane-
tho!
Thyme Herbaceous tops of Mediterranean May to 0.5-1.5 Thymol, GRAS
Thymus vulgaris L., countries, Sept. depending carvacrol except
T. zygis L. var. Central on source Spanish
facilis Boiss. Euro~e, "orig-
white thyme); or Nort anum"
T. serpr:llum L. (wild America which
thyme ; or T. capitatus is good
Hoff. & Link. (Spanish mfg
"origanum") practice
Tolubalsam Balsamic exudate Venezuela 2-7from Benzyl benzo-
of Myroxylon the crude ate, benzyl
balsamum (L.) Harms. balsam cinnamate
Tuberose Flowers of Polyanthes France, Aug.- 3-6from GRAS
tuberosa L. Morocco Sept. the extract-
edconcrete
Turmeric Dried rhizomes of India, 1.5-5 Turmerone GRAS
(curcuma) Curcuma longa L. Malaysia,
Sri Lanka,
Japan
Wintergreen Leaves of Gaultheria Canada, June to 0.5-0.7 Methylsalicy-
procumbens L. U.S.A. Sept. late
Ylang-ylang Flowers of Cananga Philippines approx 1 Alcohols and GRAS
odorata Hook.) and Malagasy, esters(50-
Thoms. Reunion 60%), sesqui-
terpenes
(30-35%)
Zedoary Rhizomes of Curcuma India approx 1 Cineole GRAS
zedoaria Rose.

Source: The following sources of information are acknowledged: Arctander (1960), Guenther (1948-1952), Lawrence (1978) plus
numerous articles that have appeared in Flavour Industry and International Flavours and Food Additives.
Chapter 10
Organic Chemicals Used in
Flavorings and Fragrances
The following data for organic chemicals
is presented in tabular alphabetical format
(Table 10-1) to provide a ready source of
information of direct and immediate con-
cern to the flavorist engaged in compound-
ing imitation flavorings. The list provides
information on:
a. The usually accepted chemical name
or common name, if this is the more
familiar usage.
b. Principal synonym(s), where these are
of value in correctly identifying the
chemical.
c. The FEMA and/or IOFI classification
number, which also aids identifica-
tion. The following symbols are used
in the tables:
Art = artificial
NI = nature-identical (substances
occurring in natural products
not normally considered as
foods)
N =natural
d. IOFI classification (Code of practice
for the flavor industry, Oct. 20, 1978,
as amended July 1990).
e. Solubility data, particularly in ethanol,
water, propylene glycol and fixed oils.
The compounding of flavorings in-
volves the blending together of ingre-
dients of wide physical disparity; this
is achieved by the use of permitted
solvents of which those quoted are
most widely used. The following
symbols are used in the tables:
In = insoluble
= very slightly soluble
VSL
SL = slightly soluble
S =soluble
VS = very soluble
M =miscible
f. Boiling point and flash point, which
are of value in determining the rela-
tive stability and safety in handling
of a flavoring, particularly where the
product is intended to be spray dried.
g. Legal status in the United States,
particularly whether the chemical is
found in nature.
Following the tabular data given below is
a supplementary tabular listing of additional
synonyms cross-referenced to the generally
accepted chemical name in the main body of
information.
391
392 Source Book of Flavors

TABLE 10-1. Aromatic Chemicals-Functional Groups

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Acetal 1,1-Diethoxy ethane 2002 35

Acetaldehyde 2003 89

Acetaldehyde butyl phenethyl acetal 3125

Acetaldehyde phenethyl propyl acetal 2004 511

Acetanisole 4' -Methoxyacetophenone 2005 570

Acetic acid 2006 2

(tri-) Acetin Glyceryl triacetate 2007

Acetoin 3-Hydroxy-2-butanone 2008 749

Acetone 3326 737

Acetophenone Methyl phenyl ketone 2009 138

4-Acetyl-6-1-butyl-1, 1-dimethylindane 3653

4-Acetyl-2-methylprimidine 3654

2-Acetoxy-3-butanone Acetoin acetate 3526 608

6-Acetoxydihydrotheaspirane 3651

4-(p-Acetoxyphenyl)-2-butanone 3652

3-Acetyl-2,5-dimethyl furan 3391

2-Acetyl-3,5 (&6)-dimethyl pyrazine 3327

3-Acetyl-2,5-dimethylthiophene 2,5-Dimethyl-3-acetylthiophene 3527

2-Acetyl-3-ethyl pyrazine 3250

2-Acetyl-5-methylfuran 1-(5-Methyl-2-furyl)-ethanone 3609

Acetylpyrazine 3126 2286

2-Acetyl pyridine 3251 2315

3-Acetyl pyridine 3424 2316

2-Acetyl thiazole 3328 4041

Aconitic acid 1-Propene-1 ,2,3-tricarboxylic acid 2010 33

Adipic acid 1,4 Butanedicarboxylic acid 2011 26

 Organic Chemicals Used in Flavorings and Fragrances 393

Legal status Physico-chemical characteristics

Solubility Flash ";;;"

Point oc 1:1'
Classi-
= 3 closed cup ·~
Q)

fication .... 0 unless u

~0
.s"'=
<;:::
European
Q)
-; o..u
0 »
"0
Q) Boiling Point oc Melting 0 =open "c:l
Q)

C.F.R. Countries ~ ~ ~6 -~
~ (at mmHg) Point oc cup ~
0..

172.515 NI Sl s s s 102-104 100 -21

182.60 NI s s s 20.8 -123.5 -40 (0) FCC

Art >200

172.515 Art s MIS 152 (26mm) 36 95

172.515 NI Sl s s 152 (26mm) 38 >110 FCC

184.1005 NI vs vs 118 17 45 (0) FCC

184.1901 s s 130.5 (7mm) 3.2 138

182.60 NI s vs MIS 140-148 15 50.5 FCC

173.210 NI s s s s 56.2 -95 -17 FCC

172.515 NI In s VSI 202 19.5 80 (C) FCC

Art MIS 76 93

NI SLS s 85-90 (10mm)

NI

NI In s >93

Art In s 155 (2.5mm)

Art 62 (0.25mm) 79

NI 70 (7mm) 90.5

NI 105-108 99

172.610 Nl 55 (l.lmm) 87

172.515 NI 100 (25mm) 80

NI s 90 (10mm) 79-80

Nl s 192 73

NI In MIS 220 13-14 150

NI 95-105 (15 mm) 64.5-65.5 78

184.1007 NI vs vs 195
(decomposes)

184.1009 Nl Sl vs 216 (15mm) 153 195 (C) FCC

394 Source Book of Flavors

TABLE 10-1. Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

~-Alanine 3252

Allyl anthranilate Allyl 2-aminobenzoate 2020 254

Allyl butyrate 2021 280

Allyl cinnamate 2022 334

Allyl crotonate 2222

Allyl cyclohexane acetate 2023 2070

Allyl cyclohexane butyrate 2024 283

Allyl cyclohexane hexanoate Allyl cyclohexane caproate 2025 2180

Allyl cyclohexane propionate 2026 2223

Allyl cyclohexane valerate 2027 474

4-Allyl-2,6-dimethoxyphenol 3655

Allyl disulfide Dally! disulfide 2028 485

Allyl 2-ethylbutyrate 2029 281

Allyl2-furoate 2030 360

Allyl heptanoate Allyl heptylate 2031 369

Allyl hexanoate Allyl caproate 2032 2181

Allyl a-ionone CetoneV 2033 2040

Allyl isothiocyanate Synthetic mustard oil 2034 2110

Allyl isovalerate 2045 2098

Allyl mercaptan 2-Propene-1-thiol 2035 476

Allyl methyl disulfide 3127 2176

Allyl methyl trisulfide 3253 2177

Allyl nonanoate Allyl pelargonate 2036 390

 Organic Chemicals Used in Flavorings and Fragrances 395

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Classi-
Q) ..!!l
PointoC
closed cup
'.s="'"
fication .... 0t:
t:
Q)
>.o 6 unless
~
u
<.t:
o.u "0
Boiling Point oc
·o
European ~ "'
..c: 0 >,
Q)
Melting 0 =open
tE
Q)

~ t:il .1:6 Point oc

0.
C.F.R. Countries (at mmHg) cup
"'
Nl vs Sl 258 (508) 207 FCC
(decomposes)

172.515 Art 105 (2mm) 230

172.515 Art In s MIS 45 (15mm) 41.5

172.515 Art In s s 150-152 (15 mm) >110

Art

172.515 Art Sl MIS 66 (1 mm) +100

172.515 Art In MIS 104 (1 mm) +100

172.515 Art In MIS 128 (1.5 mm) +100

172.515 Art Sl vs MIS 91 (1 mm) +100 FCC

EOA

172.515 Art In In 119 (1 mm) +100

NI In s 168 (11 mm)

172.515 NI In s s 138-139 62

172.515 Art 165 124

NI Sl MIS 206-209
(760mm)

Art In s 210 82

172.515 NI In MIS 180-188 68 (C) FCC

75 (15mm) EOA

172.515 Art In s 103 (0.15mm) 100 FCC

172.515 NI VSl vs 152 -102.5 46 FCC

172.515 Art In 89-90 114

172.515 NI In vs 67-68 -15.5

NI 30-33 (20 mm)

NI 47 (0.8mm)

172.515 Art In 87-91 (3mm) >93

396 Source Book of Flavors

TABLE 10-1. Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Allyl octanoate Allyl caprylate 2037 400

Allyl phenoxyacetate Acetate PA 2038 228

Allyl phenylacetate Allyl a-toluate 2039 2162

Allyl propionate 2040 2094

Allyl sorbate Allyl,2,4-hexadienoate 2041 2182

Allyl sulfide Diallyl sulfide 2042 2174

Allyl thiopropionate 3329

Allyl tiglate Allyl trans-2,3-dimethyl acrylate 2043 2183

Allyl 10-undecenoate Allyl undecylenate 2044 441

dl-(3-Amino-3-carboxypropyl) 3445 761

dimethylsulfonium chloride

Ammonium isovalerate 2054 464

Ammonium sulfide 2053 482

Amyl alcohol 1-Pentanol 2056 514

Amyl butyrate 2059 270

a-Amyl cinnamaldehyde Amyl cinnamic aldehyde 2061 128

a-Amyl cinnamaldehyde dimethyl acetal 2062 47

a-Amyl cinnamyl acetate 2064 216

a-Amyl cinnamyl alcohol 2065 79

a-Amyl cinnamyl formate 2066 357

a-Amyl cinnamyl isovalerate 2067 463

Amyl decanoate 611

Amyl formate 2068 497

Amyl 2-furoate 2072 2109

Amyl heptanoate Amyl heptylate 2073 370

Amyl hexanoate Amyl caproate 2074 315

 Organic Chemicals Used in Flavorings and Fragrances 397

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C "'
Q
Classi- <1.) ..:!l closed cup .s:
c::
0 6 unless
~
u
>.-o
<1.)
fication .... c:: -o <!::
·c:;
European 2 "'
..c::
o..u
0 >.
<1.)
I>< Boiling Point oc Melting 0 =open <1.)

C.P.R. Countries ~"' ~ ~6 ~ (at mmHg) Point oc cup 0..

Cll

172.515 Art In MIS 87-88 (5.5 mm) 95

172.515 Art s 100-102 (1 mm) +100

172.515 Art In 89-93 (3mm)

172.515 Art MIS 122-123 22

172.515 Art

172.515 Nl In s 139 -83 46

Art 49

172.515 Art In MIS 60

172.515 Art In s s s 114-118 (1 mm)

Nl s In 139

172.515 Nl s s s
172.515 vs s -18 32

172.515 NI Sl s s s 137.8 -74 47

172.515 NI VSl s 185-186 57 EOA

172.515 Nl In vs 153-154 (10mm) +100 FCC

EOA

172.515 Art s vs >200 92

172.515 Art s s 92

172.515 Art In s +100

172.515 Art s
172.515 Art s
NI +100

172.515 NI Sl s 130 -73.5 25

Art 95-97 (1 mm) >110

172.515 NI In s 245 -49.5

172.515 NI In 226 -47

398 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Amyl isovalerate 2224

2-Amyl-5 (or 6)-keto-1,4-dioxane 2076 2205

Amyl octanoate Amyl caprylate 2079 393

Amyl phenyl acetate 612

Amyl salicylate 613

Anethole 1-Methoxy-4-propenyl benzene 2086 183

Anisole Methyl phenyl ether 2097 2056

Anisyl acetate p-Methoxybenzyl acetate 2098 209

Anisyl alcohol 2099 66

Anisyl butyrate 2100 286

Anisyl formate 2101 354

Anisyl phenyl acetate 3740 233

Anisyl propionate 2102 426

Ascorbic acid 2109 27

Aspartic acid 3656

Benzaldehyde 2127 101

Benzaldehyde dimethyl acetal aa-Dimethoxy toluene 2128 37

Benzaldehyde glyceryl acetal 2129 36

Benzaldehyde propyleneglycol acetal 2130 2226

Benzenethiol Phenyl mercaptan 3616

2-Benzofuran carboxaldehyde 3128 2247

Benzoic acid 2131 21

Benzoin 2-Hydroxy-2-phenylacetophenone 2132 162

 Organic Chemicals Used in Flavorings and Fragrances 399

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-..

Point°C "'
C'
.!!1 .2
Classi-
<I)
c:: closed cup (;j
fication .... 0c:: >.-o
<I)
0 unless <J
<.<:
-o
Boiling Point oc
·a
European ~ "'
..c::
P.<J <I)
Melting 0 ==open <I)

:::
0 "'
C.P.R. Countries Iii c\::6 ~ (atmmHg) Point°C cup
P.
Vl

NI

Art Sl

172.515 NI In 260 -35

Nl

NI In s In 280

182.60 Nl In vs s 234-237 20-23 92 FCC

172.515 NI In s s 155 -37 to -38 51 FCC

172.515 NI In s s 270 +99 FCC

EOA

172.515 Nl vs s 255-265 25-27 >110 FCC

EOA

172.515 Nl In s 270 +99

172.515 Nl In s 100 100

172.515 Art In s 370 +99

172.515 NI In s 277 +99

182.3013 NI In 190 192 +99 FCC

(decomposes)

172.320 N SLS In 270-271

182.60 NI Sl s s 179 -26 62 FCC

172.515 NI In s 87-89 (18mm) 70

172.515 Art s s 185 (20mm) >93

144 (2mm)

172.515 Art s 93 (3mm) >93

172.515 NI In Sl s 170 -15 50

Art 130-131 (13mm)

184.1021 NI Sl (cold) s s 132-133 (lOmm) 121-123 121 FCC

S (hot)

172.515 Art S (hot) SIS 194 (12mm) 132-137 >93

400 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Benzoin, resinoid 2133 439

Benzophenone Diphenyl ketone 2134 166

Benzothiazole 3256

Benzyl acetate 2135 204

Benzyl acetoacetate Benzyl ~-ketobutyrate 2136 244

Benzyl alcohol 2137 58

Benzyl benzoate 2138 262

Benzyl butyl ether 2139 520

Benzyl butyrate 2140 277

Benzyl cinnamate Benzyl phenylacrylate 2142 331

Benzyl-2,3-dimethyl crotonate Benzyl methyl tiglate 2143 2187

Benzyl disulfide BDS; Dibenzyl disulfide 3617 4077

Benzyl ethyl ether 2144 521

Benzyl formate 2145 344

3-Benzyl-4-heptanone 2146 2140

Benzyl isobutyrate Benzyl-2-methyl propanoate 2141 301

Benzyl isovalerate Benzyl-3-methyl butyrate 2152 453

Benzyl mercaptan a-Toluenethiol 2147 477

Benzyl methoxyethyl acetal 2148 523

Benzyl trans-2-methyl-2-butenoate Benzyl tiglate 3330 2184

Benzyl methyl sulfide Methylthiomethyl benzene 3597

a-(methylthio) toluene

Benzyl phenylacetate 2149 232

 Organic Chemicals Used in Flavorings and Fragrances 401

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
Classi- <1.l
c :a closed cup
0
·~
fication ... 0 ;;..-s
<1.l 0 unless u
c -o<1.l <:::
·;:;
Boiling Point oc
c:>..u
~
<U
European .c 0 ;.., ~ Melting 0"' open <1.l
~6 c:>..
C.F.R. Countries ~ ~ '-i: (atmmHg) Point°C cup {/)

172.510 N

172.515 NI In s s 305 48.5 >110 FCC

EOA

NI Sl s 231 2 >110

172.515 NI Sl s s 206 -51 102 FCC

EOA

172.515 NI 156-159 (10 mm) 270 >110

172.515 NI s s MIS 205 -15.3 96 FCC

172.515 NI In s In 324 18-19 148 FCC

172.515 Art s s 220-221

172.515 NI In s s 240 107 FCC

EOA

172.515 NI In s s 195-200 (5mm) 36-40 >110 FCC

EOA

172.515 Art In s
172.515 Art In S (hot) Sl 270 71-72
(decomposes)

172.515 NI In s 185 53

172.515 NI In s s 203 4 83

172.515 Art In s
172.515 NI s 105-108 (4mm) 100 EOA

172.515 NI In vs s 245 +100 EOA

172.515 NI In s 194-195 70

172.515 Art

NI In s s 139 (9mm) >110

172.515 NI Sl 120-121 (48mm) -28 57

172.515 NI In s s 320 +100 FCC

402 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Benzyl propionate 2150 413

Benzyl salicylate Butyl a-hydroxy benzoate 2151 436

Biphenyl 3129

Bisabolene (a-, ~- andy- Isomers) 3331

Bis-(2,5-dimethyl-3-furyl) disulfide 3476 722

Bis-(2-furfuryl) disulfide 3146

Bis-(2-furfuryl) sulfide 3238

Bis-(2-methyl-3-furyl) disulfide 3259 723

Bis-(2-methyl-3-furyl) tetrasulfide 3260 724

Borneol 2157 64

Bornyl acetate 2159 207

Bornyl formate 2161 349

Bornyl isovalerate 2165 451

Bornyl valerate 2164 471

~-Bourbonene

1,2-Butanedithiol 1,2-Dimercaptobutane 3528

1,3-Butanedithiol 1,3-Dimercaptobutane 3529

2,3-Butanedithiol 3477 725

1-Butanedithiol n-Butyl mercaptan 3478 526

2-Butanone Methyl ethyl ketone 2170 755

Butan-3-one-2-yl butanoate 3332

Butyl acetate 2174 194

Butyl acetoacetate 2176 241

Butyl alcohol 1-Butanol 2178 52

 Organic Chemicals Used in Flavorings and Fragrances 403

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-..

~
Point°C c
Classi- ...c ~ closed cup
0
-~
0
fication ... 0
c ~0 -o... unless u
<C
European B
"'
..c e-
!:l..~
>< Boiling Point oc Melting 0 =open ...
"tj

C.F.R. Countries "'

~ ~ j:l..l:!) li: (atmmHg) Point°C cup
!:l..
Cll

172.515 NI In s s 220 100 FCC

EOA

172.515 NI In s s 208 (26mm) 24 +100 FCC

EOA

NI In s MIS 254-255 71 113

NI In s MIS 148 (IJ) (18mm) 100

Art 84-85 (0-3 mm)

NI Sl vs s 112-113 (5mm) 10

NI 135-143 (14mm) 31-32

NI 84-85 (0.3 mm)

Art

172.515 NI VSI s 212 203 150

172.515 NI SI s s 225 25 89 FCC
EOA
172.515 NI Sl s s 106-108 (27 mm) 97
172.515 NI In s s 255-260 +100

172.515 NI In s s 126 (12mm)

172.515 NI 229

Art In MIS 77 (28mm)

Art In MIS 91-93 <-50 250 (0)

Art In MIS 69-70 (28mm) 125

NI SI vs Sl 97-101 -116 12

172.515 NI s s s 79.6 -86 -5 FCC

Nl 76 (11mm) 82

172.515 NI VSI s s 126 -75 40 (0) FCC

172.515 Art SI s s 214 85
172.515 NI Sl M 117-118 -89 35 FCC
404 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Butylamine 3130 524

Butyl anthranilate 2181 252

Butylated hydoxyanisole BHA 2183

Butylated hydoxytoluene BHT 2184

2-Butyl-2-butenal 3392

Butyl butyrate 2186 268

Butyl butyryl lactate 2190 2107

a-Butyl cinnamaldehyde 2191 127

Butyl cinnamate 2192 326

2-sec-Butyl cyclohexanone 2-(1-Methylpropyl) cyclohexanone 3261

Butyl dec-2-enoate Butyl decylenate 2194 2100

2-(2-Butyl)-4,5-dimethyl-3-thiazoline 2,5-Dihydro-4,5-dimethyl-2-(1- 3619

methylpropyl) thiazole

sec-Butyl ethyl ether 3131

Butyl ethyl malonate 2195 384

Butyl formate 2196 501

Butyl heptanoate Butyl heptylate 2199 363

Butyl hexanoate Butyl caproate 2201 313

Butyl p-hydroxybenzoate Butoben 2203 525

3-Butylidenephthalide 3333

Butyl isobutyrate 2188 291

Butyl isovalerate Butyl 3-methyl butanoate 2218 444

2-Butyl-5( or 6)-keto-1 ,4-dioxane 2204 2206

Butyl lactate (d-, 1- and dl-forms) 2205 372

Butyl laurate Butyl dodecanolate 2206 376

Butyl levulinate 2207 374

 Organic Chemicals Used in Flavorings and Fragrances 405

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc
~
c
.;!l .~
Classi-
<)
c<) closed cup Oit.)
fication .... 0 >.-o 6 unless <::::
c o..u -o ·o<)
European 1:1 "'
..c 0 ;;., <)
>< Boiling Point oc Melting 0 =open
C.F.R. Countries "'
~ JlJ ~a iZ (at mmHg) Point°C cup
0..
rJJ

NI M M M 77 -49 zero (0)

172.515 Art In s 303 0 110

182.3169 In s s 48-63 FCC

182.3173 In s In 265 70 FCC

Art

172.515 NI Sl s s 166 -91 49.5 FCC

172.515 Art In MIS s 90 (2mm) >110 FCC

172.515 Art In s 265 >93

172.515 NI In s 295 >93

Art In s s 76-78 (8mm)

172.515 Art In s s 119 (20mm)

172.515 Art In 71 (4mm)

NI In vs 81

172.515 Art 222

172.515 NI V Sl s s 107 -90 18

172.515 NI Sl s s 226 -68 +66

172.515 NI In s 208 -64 +66

172.515 NI Sl s 68-69

NI VSI s s 141 (2.4 mm) 82-83

172.515 NI In s MIS 155-156 -22 45 EOA

172.515 NI In s s 175-176 136

Art Sl

172.515 NI Sl s MIS 185 (dl-) -28 70

172.515 NI In s s 180 (18mm) -10 >110

172.515 Art Sl s s 106-108 92

(5.5 mm)
406 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

n-Butyl 2-methyl butyrate 3393

Butyl phenyl acetate 2209 2159

3-n-Butylphthalide 3334

Butyl propionate 2211 405

Butyl salicylate 3650 614

Butyl stearate Butyl octadecanoate 2214 2189

Butyl sulfide Butyl thiobutane 2215 484

Butyl 10-undecenoate Butyl undecylenate 2216 2103

Butyl valerate n-Butyl n-valerianate 2217 466

Butyraldehyde n-Butanal 2219 91

Butyric acid 2221 5

(tri-) Butyrin Glyceryl tributyrate 2223 749

~-Cadinene (5 isomeric forms)

Caffeine 1,3, 7-Trimethylxanthine 2224

Calcium acetate 2228

Camphene 2229 2227

a-Campholenic alcohol 3741

Camphalene acetate 3657

d-camphor 2230 140

Caramel color 2235

Carboxymethyl cellulose CMC 2239

Carvacrol 2245 2055

Carvacryl ethyl ether 2246 2057

Carveol (cis and trans forms) 2247 2027

4-Carvomenthenol 1-p-Menthen-4-ol 2248 2229

 Organic Chemicals Used in Flavorings and Fragrances 407

TABLE 10·1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,e.

~

Point°C c
Classi- 11) ..!!l .52
c closed cup
fication ... 0
c
11)
>.o 0 unless
'i;j
u
<C
"0
Boiling Point oc ·u
European B
"' "'
..c
iii
P.u
0
~5
>. 11)

tf
Melting 0 =open 11)
P.
C.F.R. Countries ~ (atmmHg) Point°C cup Cll

NI In 173-176 60
(730mm)

172.515 Nl In s s 260 74

NI Sl s s 177 (15mm) +100

172.515 NI VSl s s 145-146 -89 38

NI In s 370 44 +100

172.515 NI VSl s s s 220-225 (25 mm) 19-20 190

172.515 NI Sl s 188-189 -76 76

172.515 Art In s s 125-128 (3 mm) >93

172.515 Nl VSl s s MIS 186 -93

172.515 Nl Sl s MIS 75-76 -99 -7 FCC

182.60 Nl Sl s 163.5 -5 76 FCC

182.60 Art VSl s 315 -75 +100

172.515 NI In Sl MIS 274

182.1180 Nl SL SL 238
78 (sublimes)

184.115 s IN

172.515 Nl IN SL MIS 160-162 48-51 36

Nl SLS s 74-76 (0.6mm)

Nl IN IN 96-97 (5mm)

172.515 N In vs In s 204 (sublimes) 174-179 64

182.1235 s s
182.1745 Sl >93

172.515 NI In s 236-237 0-1 106 FCC

172.515 Art MIS 235 +67

172.515 NI In s s 101-108 (10mm) 98

172.515 Nl vs 88-90 (6mm) 80

408 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Carvone (d- and !-forms) 2249 146

Carvomenthol 3562 2228

cis-Carvone oxide

Carvyl acetate 2250 2063

1-Carvyl propionate 2251 424

P-Caryophyllene 2252 2618

Caryophyllene alcohol 4061

Caryophyllene alcohol acetate

P-Caryophyllene oxide

1,4-Cineole Eucalyptol 3658

Cinnamaldehyde Cinnamic aldehyde 2286 102

Cinnamaldehyde ethylene glycol acetal 2287 48

Cinnamic acid (trans form) 2288 22

Cinnamyl acetate 2293 208

Cinnamyl alcohol 2294 65

Cinnamyl anthranilate 2295 255

Cinnamyl benzoate

Cinnamyl butyrate 2296 279

Cinnamyl cinnamate 2298 332

Cinnamyl formate 2299 352

Cinnamyl isobutyrate 2297 496

Cinnamyl isovalerate 2302 454

Cinnamyl phenylacetate 2300 235

 Organic Chemicals Used in Flavorings and Fragrances 409

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
<1) .!!l closed cup
.s
Classi- c<1)
fication .... 0
c:~ ;;:,-o 6 unless
~
u
\1:
c.u -o ·o<1)
Boiling Point oc
<1)
European ~ ..::: 0 » <1)
Melting 0 ==open
C.F.R. Countries ~ ~ ~6 tZ (at mmHg) Point°C cup
c.
(/)

182.60 NI In vs s s 231 93 FCC

EOA

NI 101.8 (14mm)

172.515 NI

172.515 NI Sl s s 77-79 (0.1 mm) 97

172.515 Art In s 78-80 (0.2 mm) 108

172.515 N In s 258-259 97 FCC

172.515 NI In s MIS 287-297 (~) 95(~), 117(a)

172.515 Art In s s 149-152 (10 mm) 40 >93

172.515 NI s s 14

172.515 N V Sl s s 174-177 50 EOA

182.60 Nl In s 248 -7.5 71 FCC

EOA

172.515 Art In s s 265 +100

172.515 NI In Sl s 300 136 +100 FCC

EOA

NI In s s 265 118 FCC

172.515 NI s s s 257.5 33 +100 FCC

EOA

172.515 Art s 332 60 +100 FCC

172.515 NI In s s 209 31 +100

172.515 NI In s 300 +100

172.515 NI In s s 370 44 +100

172.515 Nl In s s 250 100 FCC

172.515 NI In s Sl s 254 +100

172.515 NI In s Sl MIS 313 +100 FCC

172.515 Art In s 333-335 +100

410 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Cinnamyl propionate 2301 414

Citra! Neral 2303 109

Citra! diethyl acetal 2304 38

Citra! dimethyl acetal 2305 39

Citra! propylene glycol acetal 2343

Citric acid 2306 20

Citronella! Rhodinal (d-form) 2307 110

Citronella oil 2308 39

d-Citronellol 2309 59

Citronelloxyacetaldehyde 2310 2012

Citronellyl acetate 2311 202

Citronellyl butyrate 2312 275

Citronellyl formate 2314 345

Citronellyl isobutyrate 2313 296

Citronellyl phenylacetate Citronellyl a-toluate 2315 2157

Citronellyl propionate 2316 410

Citronellyl valerate 2317 469

m-Cresol 3-Hydroxytoluene 3530 617

a-Cresol 3480 618

p-Cresol 4-Cresol 2337 619

Cuminaldehyde 2341 111

Cycloheptadeca-9-en-1-one 3425
 Organic Chemicals Used in Flavorings and Fragrances 411

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c::
Classi-
<l) ..:!l closed cup
.s
c:: '(;;
0 <l)
6 u
fication .... c:: >-o
o..u -o unless <.c::
·o
Boiling Point oc
~ ell
European ell ..c:: 0 ;., <l)
.~
Melting 0 =open <l)

D:l Point oc
0..
~6
C.P.R. Countries ~
"" (at mmHg) cup (/)

172.515 NI In s 289 +100 FCC

EOA

182.60 NI VSI s s s 103-107 (12 mm) 92 FCC

EOA

172.515 Art VSI s s MIS 230 79

172.515 Art Sl s s 198 70 EOA

172.515 Art Sl s s s
182.1033 NI vs vs Decomp. 153 +100 FCC
<200 (anhydrous)

172.515 NI VSI s s 205 77 FCC

EOA

182.20 N S Sl 77

172.515 NI V Sl s s 244 102 FCC

EOA

172.515 Art In s 130 (12mm) +67

172.515 NI In s s 119-121 (15 mm) +100 FCC

EOA

172.515 NI In s s 134-135 (12 mm) +100 FCC

172.515 NI In s s 235 92 FCC

EOA

172.515 NI VSI s In s 249 +100 FCC

172.515 Art 342 +100

172.515 NI In s s 242 +100 FCC

EOA

172.515 NI In s 237 +100

NI Sl s 203 8-10 86

NI Sl s 191 31 81

172.515 NI Sl s 201-202 35-36 89.5

172.515 NI In s s 235 93

NI In s 342 32.5 +100

412 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Cyclohexane acetic acid Cyclohexyl acetic acid 2347 34

Cyclohexanecarboxylic acid 3531

Cyclohexaneethyl acetate Cyclohexyl ethyl acetate 2348 218

Cyclohexyl acetate 2349 217

Cyclohexyl anthranilate Cyclohexyl 2-aminobenzoate 2350 257

Cyclohexyl butyrate 2351 2082

Cyclohexyl cinnamate 2352 337

Cyclohexyl formate 2353 498

Cyclohexyl isovalerate 2355 459

Cyclohexylmethyl pyrazine 2-Pyrazinyl cyclohexyl methane 3631

Cyclohexyl propionate 2354 421

Cyclopentane thiol Cyclopentyl mercaptan 3262 2321

p-Cymene 1-Methyl-4-isopropylbenzene 2356 620

L-Cysteine 3263

li-Damascone 3622

2-trans-4-trans- Decadienal Heptenyl acrolein 3135 2120

y- Decalactone 2360 2230

li- Decalactone 2361 621

e-Decalactone 6-Butylhexanolide 3613

Decanal Aldehyde C-10 2362 98

Decanal dimethyl acetal 2363 43

Decanoic acid 2364 11

5 and 6-Decenoic acid 3742

9-Decanoic acid 3660

 Organic Chemicals Used in Flavorings and Fragrances 413

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c:
.!2
Classi- ""c: ..:!1
6
closed cup ~
u
fication .... 0c: ""
>--o unless <.C
c..u '0 ·o
European "" "'
..c: 0 ;>, "">< Boiling Point oc Melting 0 =open
~
~ LiJ ~6 t.I: cup
""c..
C.F.R. Countries (at mmHg) Point°C (/)

172.515 Art Sl s s 242-244 31-33 >110

Art Sl 232-233 30-32 >110

172.515 NI In 97-98 (15 mm) 81

172.515 NI In s s 172-173 58

172.515 Art In s 318 104

172.515 NI V Sl s 202-203 78
(700mm)

172.515 Art In s Sl 195 (12mm) 28

172.515 Art In s MIS 162-163

172.515 Art In s s 58-62 (0.5 mm) 89

172.515 Art Sl s 98-100 (4mm)

172.515 Art Sl s s 193

Art 41-42 (16mm) 25

172.515 NI In s MIS 176-178 -67-94 47

184.1271 NI s s 220
(decomposes)

Art In 117-120 -27 >110

(0.02mm)

NI V Sl s Sl s 64-65 (0.1 mm) >93

172.515 NI VSI s s s 153 (15mm) +100

172.515 NI VSl s s s 281 +100 FCC

Art Sl 117(3mm) >110

182.60 NI VSI s In s 207-210 17-18 85.5 FCC

EOA

172.515 Art VSI s 218 +100 FCC

172.860 NI In s s 268-270 27-32 >110 FCC

Art In s 123-127 (2 mm)

NI
414 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

1-Decanol Decyl alcohol 2365 73

Alcohol C-10

2-Decanal 2366 2009

4-Decenal 3264 2297

3-Decanol Heptylethyl carbinol 3605

3-Decen-2-one Heptylidene acetone 3532 4076

Decyl acetate 2367 199

Decyl butyrate 2368 273

Decyl propionate 2369 408

Dehydrodihydroionol 3446

Dehydrodihydroionone 3447

Diacetyl Biacetyl 2370 752

Diallyl polysulfides Diallyl di-, tri-, tetra- and 3533

penta-sulfides

Diallyl trisulfide Allyl trisulfide 3265 486

Dibenzyl ether Benzyl ether 2371 2150

Di-(butane-3-one-1-yl) sulfide 3335

4,4-Dibutyl-y-butyrolactone 2372 2231

Dibutyl sebacate 2373 622

Dicyclohexyl disulfide 3448 2320

1,2-Di[(l'ethoxy) ethoxy] propane 3534

Diethyl malate Diethyl hydroxysuccinate 2374 382

Diethyl malonate 2375 2106

2,3-Diethyl-5-methylpyrazine 3336 4260

2,3-Diethylpyrazine 3136 534

Diethyl sebacate 2376 623

Diethyl succinate 2377 438

 Organic Chemicals Used in Flavorings and Fragrances 415

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
PointoC c
Classi-
<l)
c<l) ..!!l closed cup
.s
<;;
fication ... 0
c >--o 6-o unless u
<.C
·r;
"' Boiling Point oc
<l) Q..U
European <;; ..c 0 >. <l)
>< Melting 0 ""open <l)

C.F.R. Countries :::: til tt6 Li: (at mm Hg) Point°C cup
Q..
r.n

172.515 NI In s 231 7 82 FCC

EOA

172.515 Nl In s s 78-80 (3mm) 96

Nl

Nl

172.515 NI In s s 125-126 (12 mm) 16-17 88

172.515 Nl In s MIS 272 >93

172.515 NI In s s 134-135 (8mm) >110

172.515 NI Sl s s 123-124 (8mm) 107

Art In MIS 80 (1 mm)

Art In MIS 98 (2.6mm) >93

184.1278 NI s s s s 87-88 -4 26.5 FCC

Art In Sl MIS

NI In In s 112-122 (16mm)

172.515 Art In s MIS 170 (16mm) 3-4 135

Art 95 (0.01 mm) 16

172.515 Art In s Sl 125 (3.5mm) >93

172.515 Art In s MIS 349

Art In s s 162-163 (6mm) >110

Art

172.515 NI s MIS MIS 122-124 (12 mm) 85

172.515 NI In s s s 200 -50 100 FCC

NI In s 82 (13mm) 80

NI 180-182 70.5

172.515 Art In s s 312 1-3 >110 FCC

172.515 NI Sl s s 218 -20 90.5 FCC

EOA
416 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Diethyl tartrate 2378 440

2,5-Diethyl tetrahydrofuran 3743

Difurfuryl ether 3337

Dihydro-a-ionone 3628

Dihydro-JJ-ionol 3627

Dihydro-JJ-ionone 3626

Dihydrocarveol 8-p-Menthen-2-ol 2379 2025

Dihydrocarvone 8-p-Menthen-2-one 3565 4001

Dihydrocarvyl acetate 8-p-Menthen-2-yl acetate 2380 2064

Dihydrocoumarin 1,2-Benzodihydropyrone 2381 535

4,5-Dihydro-3 (2H) thiophenone 3266 2337

5,7-Dihydro-2-methylthieno (3,4-D)- 3338 720

pyrimidine

Dihydroxyacetophenone 3662 2238

m- Di~ethoxybenzene Dimethylresorcinol 2385 189

p-Dimethoxybenzene Dimethylhydroquinone 2386 2059

1,1-Dimethoxyethane Dimethylacetal 3426 510

2,6-Dimethoxyphenol 3137 2233

3,4-Dimethoxy-1-vinylbenzene 3138

2,4-Dimethylacetophenone 2387 157

1,4-Dimethyl-4-acetyl-1-cyclohexene 3449

2,4-Dimethyl-5-acetylthiazole 3267

2,4-Dimethylbenzaldehyde 3427

2,3-Dimethylbenzofuran 3535

p-a-Dimethyl benzyl alcohol 3139 4082

a, a-Dimethyl benzyl isobutyrate 2388 2086

 Organic Chemicals Used in Flavorings and Fragrances 417

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

..,c Point°C c.:2"'

..:!l
Classi-
0c
.., 6
closed cup 'iu<i
fication ..,.... >-.o ..,
"0
unless <.C
·n..,
Boiling Point oc
c.u
European 'i<i "'
..c 0
P:C3
» >< Melting 0 =open c.
C.F.R. Countries ~ til l.i: (at mmHg) Point°C cup Vl

172.515 NI In s s 280 17 93

NI Sl s s s 116

NI In 101 (2mm)

NI In s 234 >93

NI In 234

NI In 90 (0.2mm) >93

172.515 NI s 223 91.5

172.515 NI In s s 87-88 (6mm) 81

172.515 NI Sl s 232-234 90

NI Sl MIS 272 25 130 EOA

NI 175 72

Art >93

NI SLS 145-147

172.515 NI Sl s 85-87 (7mm) -52 to -55 87

172.515 NI Sl s 213 56-60 94

NI s s s 64-65 -28

NI Sl s s 261 53-56 >110

NI

172.515 NI In s s 288 39-41 208

NI In 82-89 (10 mm)

Art 79 (1.4mm)

NI In s 212-215 -9 88

NI In s 96-98 (15 mm)

Nl Sl s s s 219 88 FCC

172.515 Art In s 71-72

418 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

3,4-Dimethyl-! ,2-cyclopentadione 3268 2234

3,5-Dimethyl-1 ,2-cyclopentadione 3269 2235

4,5-Dimethyl-3-hydroxy-2, 2,3-Dimethyl-4-hydroxy-2,5- 3634

5-dihydrofuran-2-one dihydrofuran-5-one

2,5-Dimethyl-2,5-dihydroxy-1 ,4-dithiane 3450 2322

Dimethyl disulfide Methyl disulfide 3536 2175

4,5-Dimethyl-2-ethyl-3-thiazoline 2-Ethyl-4,5-dimethyl-3-thiazoline 3620

2,5-Dimethyl-3-furanthiol 3451

2,6-Dimethyl-4-heptanol Diisobutyl carbinol 3140 4030

2,6-Dimethyl-4-heptanone Diisobutyl ketone 3537

2,6-Dimethyl-5-heptenal 2389 2006

2,6-Dimethyl-6-hepten-1-ol 3663

2,5-Dimethyl-4-methoxy-3(2H)-furanone 3664

2,2-Dimethyl-5-(1 methylpropen-1-yl) 3665

tetrahydrafuran

2,6-Dimethyl-3-[ (2-methyl-3-furyl) thio ]- 1,3-Diisopropylacetonyl-2-methyl-3- 3538

4-heptanone fury! sulfide

4,5-Dimethyl-2-isobutyl-3-thiazoline 2,5-Dihydro-4,5-dimethyl-2-(2- 3621

methylpropyl) thiazole

2,6-Dimethyl-10-methylene-2,6, 11- ~-Sinensal 3141

dodecatrienal

3, 7-Dimethylocta-2,6-dienyl-2-ethyl Geranyl 2-ethyl butyrate 3339

butanoate

2,6-Dimethyloctanal 2390 112

3,7-Dimethyl-1-octanol Tetrahydrogeraniol 2391 75

3, 7-Dimethyl-! ,3 ,6-octatriene trans-~-Ocimene 3539 4022

3-7-Dimethyl-6-octenoic acid Citronellic acid 3142 616

2,4-Dimethyl-2-pentenoic acid 3143 744

a,a-Dimethylphenethyl acetate Dimethyl benzyl carbinyl acetate 2392 2077

 Organic Chemicals Used in Flavorings and Fragrances 419

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-.

"'
C'
., Point°C
.sa
Classi- .,c 6"' closed cup ';
fication ...., 0
c >.-s ., unless u
<.=
European '; "'
.c
P,U
0 ;:....
"0
Boiling Point oc Melting 0 =-open .,P.
'tj

:s: ct:G
~

C.F.R. Countries Lij iZ (atmmHg) Point°C cup <l'l

NI 66 (1 mm) >93

NI 91-92 >93

NI

Art s
172.515 NI Sl s s 112 -85 24

172.515 Art In 50 (3mm)

Art In 70 (30mm)

NI In s 178 63

NI VSI s s 168 48

172.515 NI 144 EOA

Art In s 62 (1mm)

NI s s 61-63 (0.3mm)

NI SLS MIS 65 (10mm) 53

Art In 90-92 (0.2mm)

172.515 NI In 71 (4mm)

NI 180 (1mm)

NI

172.515 Art In s s 82-84 (15 mm)

172.515 NI In s s s 221-223 FCC

EOA
172.515 NI In s In s 177 40

NI In s s 121-122 (1mm) >110

Art +66

172.515 Art s Sl s 250 29.5 +100 FCC

EOA
420 Source Book of Flavors

TABLE 10·1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

a,a-Dimethylphenethyl alcohol Benzyl dimethyl carbinol 2393 84

a,a- Dimethylphenethyl butyrate 2394 2084

a,a-Dimethylphenethyl formate 2395 353

2,3-Dimethylpyrazine 2,3-Dimethyl-1 ,4-diazine 3271

2,5-Dimethylpyrazine 2,5-Dimethyl-1 ,4-diazine 3272 2210

2,6-Dimethylpyrazine 2,6-Dimethyl-1 ,4-diazine 3273 2211

2,6-Dimethylpyridine 3540

p-a- Dimethylstyrene p-Isopropenyl toluene 3144 2260

2,6-Dimethylthiophenol 3666

Dimethyl succinate 2396 439

4,5-Dimethylthiazole 3274

2,5-Dimethyl-3-thiofuroylfuran 3481 2323

2,5-Dimethyl-3-thioisovalerylfuran 3482 2324

Dimethyl trisulfide 3275 539

2,4-Dimethyl-5-vinyl thiazole 3145 2237

3,5-Dimethyl-1 ,2,4-trithiolane 3541 2236

6, 10-Dimethyl-5, 9-undecadien-2-one Geranyl acetone 3542

Dihydroxyacetophenone 3541 2236

Diphenyl ether 3667 2201

1,3-Diphenyl-2-propanone Dibenzyl ketone 2397 2054

Dipropyl trisulfide 3276 726

Disodium 5-guanylate 3668

Disodium 5-inosinate 3669

Disodium phosphate 2398

Disodium succinate 3277

 Organic Chemicals Used in Flavorings and Fragrances 421

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.g
Classi- "'c .!!l closed cup
fication ... 0
c "'o..u 0
>.o unless "'u
<.1:
"'
"t)

-s"' Boiling Point oc

"<:j

tt6 ~"'
European 'Oi 0 >. Melting 0 =open
~ "'
P-
C.F.R. Countries
"" (atmmHg) Point°C cup Vl

172.515 NI s s s 108 (11 mm) 24 92 FCC

EOA

172.515 Art In s s 234 +66

172.515 Art VSl s 156

NI s s 156 54

NI s s 155 64

NI s s 154 35-40 53

NI s s 143-145 -6 33

NI In s 186-189 -20

NI SLS s 87

172.515 NI s s MIS 195-1% 18-19 85

NI s 158 83-84

Art In Sl 83 (0.7mm)

Art In Sl 124-125 (6mm)

NI Sl s s s 165-170 34

NI Sl 165-170

NI In s 38 (0.3mm)

172.515 In VSl s s s 247 >93

NI Sl 143

NI In s 259 27 >93

172.515 Art In s s 331 35

NI VSl s s 68-69 (0.9mm) 20

172.530 s Sl FCC

172.5350 s Sl FCC

>93

NI s In >93
422 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

spiro (2,4-Dithia-1-methyl-8-oxabicyclo- 3270

(3,3,0) octane-3,3' (I' -oxa-2' -methyl)
cyclopentane

2,8-Dithianon-4-en-4-carboxaldehyde 3483

2,2' -(Dithiodimethylene )-difuran 3146

2-trans-6-cis- Dodecadienal 3637

trans trans-2,4-Dodecadienal 3670

y- Dodecalactone Dodecanolide-1 ,4 2400 2240

o- Dodecalactone 2401 624

1:- Dodecalactone 6-Hexylhexanolide 3610

Dodeca-3,6-dienal 2121

2-Dodecenal 2402 124

y-Dodecen-6-lactone 625

Dodecyl isobutyrate 3452

Erythorbic acid Isoascorbic acid 2410 30

Estragole p-Allyl anisole 2411 184

1 ,2-Ethanedithiol 3484

p-Ethoxybenzaldehyde 2413 626

7-Ethoxy-4-methyl coumarin 2193

o-(Ethoxymethyl) phenol 3485

2-Ethoxythiazole 3340

Ethyl acetate 2414 191

Ethyl acetoacetate 2415 240

Ethyl 2-acetyl-3-phenyl propionate Ethyl benzyl acetoacetate 2416 2241

 Organic Chemicals Used in Flavorings and Fragrances 423

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c.2"'
Classi-
<!) ..:!1 closed cup
c ';;;
fication .... 0
c ;;:,-o
<!) 6 unless
u
\I:
-o
Boiling Point oc
·u
""
<!) Q.U
European ';;; .c 0 ;>,
<!)
Melting 0 =open <!)

C.F.R. Countries ~ Ill Q:6 .~

LJ.. (at mmHg) Point oc cup
Q.
(/)

Art 135-140 (3 mm)

NI Sl

NI VSI s s 112-113 10-11 >110

(0.5mm)

NI In s 85 (0.3mm) 99

NI SLS s 130 (6mm) 104

172.515 NI In s Poor 130-132 17-18 >110

(l.Smm)

172.515 NI In s Poor 140-141 (1 mm) -12 >110 FCC

Art Sl MIS >93

Art

172.515 NI In s s 103-109 (1 mm) >93 EOA

NI

NI In +100

182.3041 Art s s >200 164-174 >200 FCC

(decomposes)

172.515 NI V Sl s s 214-216 81 FCC

NI In MIS 144-146 -41 50

172.515 NI VSI s s 255 13-14 >110

Art 113 113 +100

Art s 281 109-111

Art 157-160 54

182.60 NI s s s s 76-77.5 -83.4 3 FCC

172.515 NI Sl s s s 181 -43 85 FCC

172.515 Art In 290

(decomposes)
424 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

1-Ethyl-2-acetylpyrrole 3147

Ethyl aconitate (mixed esters) 2417 2108

Ethyl acrylate Ethyl propenoate 2418 245

Ethyl alcohol Ethanol 2419

Ethyl p-anisate Ethyl p-methoxybenzoate 2420 249

Ethyl anthranilate 2421 251

Ethyl benzoate 2422 261

Ethyl benzoylacetate 2423 627

a-Ethylbenzyl butyrate 2424 628

Ethyl-trans-2-butenoate Ethyl crotonate 3486 2244

2-Ethylbutyl acetate 2425 215

Ethyl butyrylacetate 2242

2-Ethyl butyraldehyde 2426 95

Ethyl butyrate 2427 264

2-Ethyl butyric acid 2429 2001

Ethyl cyclohexanecarboxylate 3544

Ethyl cinnamate 2430 323

Ethyl crotonate Ethyl ~-methylacrylate 3486 2244

Ethyl cyclohexane propionate 2431 2095

Ethyl trans-2-cis-4-decadienoate 3148

Ethyl decanoate Ethyl caprate 2432 309

Ethyl trans-2-decenoate 3641

Ethyl trans-4-decenoate 3642

2-Ethyl-4,5-dimethyloxazole 3672

4-Ethyl-2,6-dimethoxyphenol 3671
 Organic Chemicals Used in Flavorings and Fragrances 425

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash
Point ac c"'
.s
Classi-
(1) ..'!l closed cup
c(1)
6
fication ... 0c ;;:,-o
o..u -o(l) unless ""u
<.:
Boiling Point ac
(1) ~ "()
European ..c 0 ;;.., >< Melting 0 =open (l)

C.F.R. Countries ""

~ Cil c\::6 ti: (at mmHg) Point ac cup
0..
<ll

NI

172.515 Art Sl s 172 (18mm)

172.515 NI Sl s MIS 99-100 -71 10 FCC

NI M MIS 78 14 FCC

172.515 NI In s MIS 263 7-8 >110 FCC

172.515 NI s s s 129-130 (9 mm) 13-15 >110 FCC

172.515 NI VSl s s s 212 -34 84 FCC

EOA

172.515 Art In s 270 >93

172.515 Art In MIS 282 118

172.515 NI s 142-143 2

172.515 Art Sl s 160-163

Art

172.515 NI Sl s 117 -89 21 FCC

182.60 NI Sl s s s 120 -93 20 FCC

EOA

172.515 NI Sl s 99-101 (18 mm) -14 88 FCC

NI Sl s s 248-249

172.515 NI In s MIS 271 7 >110 FCC

172.515 NI s 142 2

172.515 Art In s MIS 91-94 (8mm) 50

NI 70-72 (0.05 mm) >110

172.515 NI s 245 -20 102 EOA

NI In s 93 (0.2mm) 230

NI 90 (3mm) 230

NI In SLS 137 (732mm)

NI In s 106 (0.2mm)
426 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Ethyl-3,(5 or 6)-dimethylpyrazine 3149 727

Ethyl trans-2-hexenoate 3675

3-Ethyl-2,6-dimethylpyrazine 3150 2246

Ethyl-2,4-dioxohexanoate 3278

Ethyl 2-ethyl-3-phenyl propanoate 3341

Ethyl brassylate Ethyl tridecanedioate 3543 4094

Ethyl formate 2434 339

2-Ethylfuran 3673 4004

Ethyl 3(2-furyl) propanoate Ethyl furfuryl acetate 2435 2091

4-Ethyl guaiacol 4-Ethyl-2-methoxyphenol 2436 176

Ethyl heptanoate Ethyl heptoate 2437 365

2-Ethyl-2-heptenal 2-Ethyl-3-butylacrolein 2438 120

Ethyl hexanoate Ethyl caproate 2439 310

1-Ethyl hexyl tigate 3676

2-Ethyl-1-hexanol Octyl alcohol 3151

Ethyl 3-hexenoate 3342 631

Ethyl 3-hydroxybutyrate 3428

3-Ethyl-2-hydroxy-2-cyclopenten-1-one 3152 759

Ethyl 3-hydroxyhexanoate Ethyl 3-hydroxycaproate 3545

3-Ethyl-2-hydroxy-4-methylcyclopen-2- 3453
en-l-one

5-Ethyl-2-hydroxy-4-methylcyclopen-2- 3454
en-l-one
 Organic Chemicals Used in Flavorings and Fragrances 427

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.:a .52
Classi-
0
"'
1:
0
closed cup 'iu<i
fication .... 1: ~0 -o unless <::::
·o
*s
European "'
.c c..~
"' Boiling Point oc Melting 0 =open
C.F.R. Countries ~ lil 8-
t:~-.0
X
li: (atmmHg) Point°C cup "'c..
Cll

Nl s 180-181 70

NI SLS s 62 (25mm) 64

NI

Art 100-105 (6mm)

Art 72

172.515 Art In s Poor 332 -5 >200

184.1295 NI Sl s s s 52-54 -80 -20 FCC

(decomp.) EOA

172.515 NI VSI s s 93

172.515 Nl 260 24.5

172.515 NI Sl MIS 229-230 110 +67

172.515 NI AzM s Sl s 188-189 -66 66 FCC

172.515 Art In MIS

172.515 NI In s Sl s 167 -67 to -68 49 FCC

Art In MIS 94-96 (60mm)

NI In s s 184-185 -76 80

Nl In s s 63-64 (12mm) 54

NI 170 64

Nl 78-80 (4mm) 38-40 107

NI VSI s s 90-92 (14mm) 94

NI Sl MIS s

Nl Sl s s
428 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Ethyl-4-hydroxy-5-methyi-3(2H)- 5-Ethyl-4-hydroxy-2-methyi-3(2H) 3623

furanone furanone

5-Ethyl-3-hydroxy-4-methylcyclopen-2 3153 4005

(5H)-furanone

Ethyl isobutyrate 2428 288

N-Ethyl-2-isoprophyl-5-methylcy- 3455 2298
carboxamide

Ethyl isovalerate 2463 442

Ethyl lactate Ethyl 2-hydroxypropionate 2440 371

Ethyl laurate Ethyl dodecanoate 2441 375

Ethyl levulinate Ethyl 4-oxopentanoate 2442 373

Ethyl maltol 3-Hydroxy-2-ethyl-4-pyrone 3487 692

Ethyl 2-mercaptopropionate 3279

Ethyl 3-mercaptopropionate 3677

2-Ethyl-(3 or 5 or 6)-methoxypyrazin~) mixture 3280

2-Methyl-(3 or 5 or 6)-methoxypyrazme)

Ethyl 2-methylbutyrate (FCC synonym: Ethyl isovalerate) 2443 265

Ethyl 2-methylpentanoate 3488

Ethyl 2-methyl-3-pentenoate 3456

Ethyl2-methyl-3,4-pentadienoate 3678

Ethyl 2-methyl-4-pentenoate 3489

Ethyl 3-methylpentanoate 3679

Ethyl methyl phenylglycidate Strawberry aldehyde, Aldehyde C-16 2444

2-Ethyl-5-methylpyrazine 3154 728

3-Ethyl-2-methylpyrazine 3155 548

5-Ethyl-2-methylpyridine 2-Methyl-5-ethylpyridine 3546

 Organic Chemicals Used in Flavorings and Fragrances 429

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c.52"'
,!!;!

.
Classi- <U
c: closed cup 'itJU
0c: 6
fication ~8 '0
unless
~<U
-5"' Boiling Point oc
<U
European 'iU g.~ <U
Melting 0 =-open c.
C.F.R. Countries ~ ~ Q:~ ~ (atmmHg) Point°C cup ell

NI >93

NI 83-86 (0.5mm) 31-35 >110

172.515 NI Sl s s 110-112 -88 14

Art In

172.515 NI vs s Sl s 131-133 -99 26 FCC

EOA

172.515 NI vs s s 154 -26 49 FCC

172.515 NI In M s 269 >110 FCC

172.515 NI s s s 93-94 (18 mm) 90.5

172.515 Art s s s 89-93 90 +100 FCC

NI 40-41 (1mm) 58

NI 162

Art

172.515 NI Sl MIS 132-133 +67 FCC

Art In s 153 152-153

Art In 85-91 (50mm) 43

Art In s 88-90 (55 mm)

Art In MIS MIS 64 (30mm)

NI In s 60 (15mm) 41

182.60 Art In s s s 150-153 (8mm) 134 FCC

NI 79-80 (50mm) 57

NI 69-70 (16mm) 58

NI VSI s SI s 172-175 66
430 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Ethyl 4-(methylthio) butyrate 3681

Ethyl 3-methylthiopropionate 3343

2-Ethyl-4-methylthiazole 3680

Ethyl myristate Ethyl tetradecanoate 2445 385

Ethyl nitrite 2446 2190

Ethyl nonanoate Ethyl pelargonate 2447 388

Ethyl 2-nonynoate Ethyl octine carbonate 2448 480

Ethyl octadecanoate 3490

Ethyl cis-4,7-octadienoate 3682

Ethyl octanoate Ethyl caprylate 2449 392

Ethyl cis-4-octenoate 3344

Ethyl trans-2-octenoate 3643

Ethyl oleate 2450 633

Ethyl 3-oxohexanoate 3683

Ethyl palmitate 2451 634

p-Ethyl phenol 4-Ethyl phenol 3156 550

Ethyl phenylacetate Ethyl a-toluate 2452 2156

Ethyl 4-phenylbutyrate 2453 307

Ethyl 3-phenylglycidate Ethyl phenylglycidate 2454 2097

Ethyl 3-phenylpropionate Ethyl hydrocinnamate 2455 402

Ethyl propionate 2456 402

2-Ethylpyrazine 3281 2213

3-Ethylpyridzine 3394

Ethyl pyruvate 2457 430

 Organic Chemicals Used in Flavorings and Fragrances 431

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c"'
.s
Classi- "!::= 6
..:!l closed cup ~
u
fication .... 0!::= "
>.-o
c..u -o
unless It:
·n
" Boiling Point oc
iE"
0:
..c » Melting 0 =open
European
Countries
~
~ LiJ
0
~6 (at mmHg) Point oc cup
"c..
(/)
C.F.R.

Art 52 (3mm)

NI 77-79

NI SLS s 58 (20mm) 66

172.515 NI In Sl 178-180 (12mm) 11-12 >110

172.515 Art V Sl s 16.4 -31

172.515 NI In s s 119 (23mm) -44 94 FCC

172.515 Art In s s 227 104

172.515 NI +100

NI

172.515 NI In s Sl s 207-208 -48 75 FCC

EOA

NI 105 (11 mm)

NI In s 93-96 (10mm) 90

172.515 NI In s MIS 207 176

Art

NI In s MIS 192-193 (10 mm) 24-26 >110

NI Sl s s 218-219 42-46 100

172.515 NI In s In s 276 +100 FCC

EOA

172.515 Art In s s
172.515 Art V Sl s s +100 FCC
EOA

172.515 NI In s s 247-248 108

172.515 NI Sl s s s 99 -73 12 FCC

NI 152-153 43

NI Sl s s 162-163 48

172.515 NI Sl s 144 -50 45

432 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Ethyl salicylate Ethyl o-hydroxybenzoate 2458 432

Ethyl sorbate Ethyl 2,4-hexadienoate 2459 635

Ethyl thioacetate 3282

2-Ethylthiophenol 3345

Ethyl tiglate Ethyl trans-2,3-dimethyl-acrylate 2460 2185

Ethyl-(p-tolylox) acetate 3157 2243

2-Ethyl-1 ,3,3-trimethyl-2-norbornanol 3491

Ethyl undecanoate Ethyl undecylate 3492

Ethyl 10-undecenoate Ethyl undecylenate 2461 2102

Ethyl valerate 2462 465

Ethyl vanillin 3-Ethoxy-4-hydroxybenzaldehyde 2464 108

Eucalyptol 1,8-Cineole 2465 182

Eugenol 4-Allyl-2-methoxyphenol 2467 171

iso Eugenol 2-Methoxy-4-propenyl phenol 2468 172

Eugenyl acetate Acetyl eugenol 2469 210

iso Eugenyl acetate 2-Methoxy-4-propenylphenyl acetate 2470 220

Eugenyl benzoate 2471 636

Engenyl formate 2473 355

Eugenyl methyl ether Methyl eugenol 2475 185

Farnesol 2478 78

d-Fenchone 2479 551

Fenchyl alcohol 2-Fenchanol 2480 87

Formic acid 2487

 Organic Chemicals Used in Flavorings and Fragrances 433

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.2
Classi- "'c .!!l
0
closed cup ';
fication ... 0
c "'
;:.,-s "0
unless u
<=
-5"' §-1- "' Boiling Point oc
'tj
European ~ Melting 0 =open
C.F.R. Countries :s: r.l.l ll':o ~ (at mmHg) Point°C cup "'c..
Vl

172.515 NI VSl s s s 231-234 2 107 FCC

EOA

172.515 NI Sl s MIS 82-83 (13mm) 69

NI In vs s 116 18

Art 203-205 80.5

172.515 NI In s s 154-156 44

Art In In 120-121 (1 mm) >110

Art Sl s
172.515 Nl In s s 105 (4mm) >110

172.515 Art In s s 258-259 >110

172.515 NI VSl s s 144-145 39

182.60 Art Sl s s 176-177 76-78 +100 FCC

172.515 N s s s 176-177 50 EOA

184.1257 NI Sl s s s 254 -12 to -10 >110 FCC

172.515 Nl In s s s 268 19 +100 FCC

EOA

172.515 Nl In s Sl s 281-282 29-30 +66 FCC

172.515 Art In s Sl s 77 EOA

FCC

172.515 Nl In s s 360 69-70 >93

172.515 Art In s s 270 102

172.515 NI VSl s In s 244-245 +100 EOA

FCC

172.515 NI VSl s 144-146 (2mm)

172.515 NI In vs 193 dl, >0; 52

d,l,5-6

172.515 NI VSl s MIS 48-49 +67

172.515 Nl s s s 100-101 8.3 69 FCC

434 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Formyl-6,6-dimethylbicyclo (3,1,1)- Myrtenal 3395

hept-2-ene

Furmaric acid trans-Butanedioic acid 2488 25

2-Furanmethanethiol formate 3158 4112

Furfural 2-Furfuraldehyde 2489 2014

Furfury acetate 2490 2065

Furfuryl alcohol 2491 2023

Furfuryl butyrate 638

2-Furfurylidene butanal 2492

Furfurylidene-2-propanal 2-Methyl-3-furylacrolein 2704 2216

Furfurylisopropyl sulfide 3161 2248

Furfuryl mercaptan 2493 2202

Furfuryl 3-methylbutanoate 3283

Furfuryl methyl ether 3159

Furfuryl methyl sulfide 3160

a-Furfuryl octanoate 3396

a-Furfuryl pentanoate a-Furfuryl valerate 3397

Furfuryl propionate 3346

N-Furfurylpyrrole 1-(2-Furfurylpyrrole) 3284 2317

Furfuryl thioacetate 3162 2250

Furfuryl thiopropionate 3347

Fury! acrolein 2494 2252

2-Furyl methyl ketone Acetylfuran 3163

(2-Furyl)-2-propanone Furfuryl methyl ketone 2496

Geraniol trans- 3, 7-Dimethyl-2,6-octadien-1-ol 2507 60

Geranyl acetate 2509 201

 Organic Chemicals Used in Flavorings and Fragrances 435

TABLE 10·1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

"'
I:'
., Point•c
.52
= closed cup
,!!;~
Classi- ';
... 0 .!!- 0
.,
CJ
fication
European B =..s
..c:
>.o
Q.CJ
0 >.
"0
Boiling Point •c Melting
unless
0 ==open
<::::
.,
'tj
..s ~

C.F.R. Countries ~ Lij ~6 i.i: (atmmHg) Point•c cup

Q.,
Cl)

NI In s s 199 96

172.515 NI Sl s Sl 290 (760mm) 287 +100 FCC

Art 66 (15mm) >110

NI s s s 161 -36.7 60 FCC

NI In s 175-177 65

NI MIS MIS 170 -29 65

NI In 129-130 (52mm) 90.5

Art

NI

Art 79-80 (12mm) 75.5

NI In s s 155 45

NI 97-98 (11 mm) 96

NI In s 134-135

NI In s 64-65 (15 mm) 63

Art 139 (10mm) >110

NI 82-83 (1mm) 98

NI Sl 195-196 81.5

NI s s 76-78 (1mm) 93

NI MIS 90-92 (12 mm) 93

Art 95-97 (lOmm) 98

NI 100-102 (12mm) 51-55 99.5

NI In s s 67 (10mm) 29-32 71

172.515 NI In s s 179-180

182.60 NI VSI s s s 230 -15 101 FCC

EOA

182.60 NI In s s MIS 128-129 104 FCC

EOA
436 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Geranyl acetoacetate 2510 243

Geranyl acetone 3542 4083

Geranyl benzoate 2511 639

Geranyl butyrate 2512 274

Geranyl formate 2514 343

Geranyl hexanoate Geranyl caproate 2515 317

Geranyl isobutyrate 2513 306

Geranyl isovalerate 2518 448

Geranyl phenylacetate 2516 231

Geranyl propionate 2517 409

Glucose pentacetate 2524

!-Glutamic acid 3285

Glutamine 3684

Glycerol Glycerin( e) 2525 4117

Glyceryl 5-hydroxydecanoate 3685

Glyceryl 5-hydroxydodecanoate 3686

Glyceryl monooleate 2526

Glyceryl monostearate 2527

Glyceryl tribenzoate 3398

Glyceryl tripropanoate 3286

Glycine Aminoacetic acid 3287 4118

 Organic Chemicals Used in Flavorings and Fragrances 437

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.!2
Classi-
<)
c: ~
closed cup
fication ... 0c ~-
>.o
6 unless
~
u
<C
o..u -o
Boiling Point oc
·o
..,
European B
"' ~
"'
..c: 0
c:a
>. <)
><
Li:
Melting 0 =open
0..
C.F.R. Countries ~ (at mmHg) Point°C cup
"'
172.515 Art In s s +100

172.515 NI +100

172.515 NI VSI s s 198-200 +100 FCC

172.515 NI In s In s 151 93 FCC

EOA

172.515 NI In s In s 113-114 (15 mm) 96 FCC

EOA

172.515 NI In s s 240 +100

172.515 NI In s s 245 +100

172.515 NI In s s 135-138 (7mm) +100

172.515 Art VSl M s 342 +100 FCC

EOA

172.515 NI s s In s 253 +100 FCC

EOA

172.515 Art In s In 149-151 (7mm) a-114 >110

~-135

182.1045 NI Sl In 175 (10mm) 190 FCC

(sublimes) (decomposes)

172.320 N SLS In 190

182.1320 NI s s s In 182 (2mm) 20 160 FCC

Art In s
Art In s
172.515 In s s 14-19 +100

182.1324 (Disp) s s 58-59 +100

s 76 +100

Art Sl s 177-182 (20mm) -50 +100

NI vs In 262 262 FCC

(decomposes)
438 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Glycyrrhizin, ammoniated 2528

Guaiacol o- Hydroxyanisole 2532 173

o-Methoxyphenyl

Guaiacyl acetate 3687 552

Guaiacyl phenylacetate 2535 238

Guaiene

Guaiol acetate

2,4-Heptadienal 3164 2123

y-Heptalactone Heptanolide-1 ,4 2539 2253

Heptanal Aldehyde C-7 2540 117

Heptanal dimethyl acetal 2541 2015

Heptanal glyceryl acetal (mixed 1,2 & 1,3) 2542 2016

2,3-Heptanedione 2543 2044

Heptanoic acid Oenanthic acid 3348 28

2-Heptanol 3288 554

3-Heptanol Ethyl butyl carbinol 3547 544

4-Heptanol 555

2-Heptanone Amyl methyl ketone 2544 136

3-Heptanone Ethyl butyl ketone 2545 137

4-Heptanone Dipropyl ketone 2546 2034

2-Heptenal 3165 730

4-Heptenal n-Propylidene butyraldehyde 3289 2124

4-Heptenal diethyl acetal 3349

2-Hepten-4-one Propenyl propyl ketone 3399

3-Hepten-2-one Methyl pentenyl ketone 3400

trans-3-Heptenyl acetate 3493

 Organic Chemicals Used in Flavorings and Fragrances 439

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-.._

~
Point°C c
.5!
Classi- "
c
6
.!!l closed cup t;j
fication .... 0c "
>.-s -o unless u
<C
·c:;
" "' c..u
Boiling Point oc
lE"
European t;j ..c 0» Melting 0 =open
C.P.R. Countries ~ ~ ~6 (atmmHg) Point°C cup ~
"c.
182.20 NI

172.515 NI Sl s 205 27-29 82

172.515 NI VSl s 235-240 31-32

172.515 Art In s 235-240 40-43 >110

172.515 NI s 128-130 (12 mm) >93

172.515 Art s +100

NI s s 100 (25mm) 60

172.515 NI VSl s s 61-62 (2mm) >110 FCC

172.515 NI In s MIS 152.6 -43.71 34

172.515 Art VSl s s s 164-165 59 FCC

EOA

172.515 Art Sl s 164-165

172.515 NI vs s 43

173.315 NI Sl s 223 -10 112

NI Sl s s 160 41

172.515 In s s 157 54

NI

172.515 NI Sl s s 157-158 -26.9 47

172.515 NI VSl s s MIS 146-149 -39 41 FCC

172.515 NI In s s MIS 144 -33 48

NI VSl s 90-91 (50mm) 53

172.515 NI In s s 112-113 20

Art VSl s s 93 (115mm) 78

NI VSl s s 156-157 34

NI VSl s s 162 51

Art
 440 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

trans-3-Heptenyl 2-methyl propanoate 3494

Heptyl acetate 2547 212

Heptyl alcohol 1-Heptanol 2548 70
Heptyl butyrate 2549 504

Heptyl cinnamate 2551 2104

Heptyl formate 2552 341
2-Heptyl furan 1-(2-Furyl)-heptane 3401

Heptyl isobutyrate 2550 295

3-Heptyl-5-methyl-2 (3H)-furanone 3350

Heptyl octanoate Heptyl caprylate 2553 399

1-Hexadecanol Alcohol C-16 2554 57
Cetyl alcohol

w-6-Hexadecenlactone Ambrettolide 2555 180

trans-trans-2,4-Hexadienai Sorbic aldehyde 3429 640

4,4a,5 ,6, 7,8-Hexahydro-6-isopropenyl- Nootkatone 3166
4,4a-dimethyl-2 (3H)-naphthalenone

y-Hexalactone y-Ethyl-n-butyrolactone 2556 2254

o-Hexalactone 3167 641
Hexanal Aldehyde C-6 2557 96
2,3-Hexanedione 2558 152

3,4-Hexanedione 3168 2255

1,6-Hexanedithiol 3495

Hexanoic acid 2559 9

3-Hexanol 3351

3-Hexanone 3290

2-Hexenal 2560 748

cis-3-Hexenal 2561 2008
 Organic Chemicals Used in Flavorings and Fragrances 441

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C "'c
'-'

Classi- ...c .!!l closed cup

.9
<;;
... 0 6 u
fication
European .,
~
.,
c
..c
..!:l-
>.o
c..u
0 >.
-o...
Boiling Point oc Melting
unless
0 ==open
<.C
·;:;
...
><
C.F.R. Countries ~ IU ~a li: (at rnrn Hg) Point°C cup
Q,
Cl)

Art

172.515 NI In s MIS 192-193 -50 68

172.515 NI In s s 177 -36 74 FCC
172.515 NI VSI s s s 226 -58 90.5

172.515 Art In s VSI

172.515 NI In s s MIS 178 60

NI 209-210 75
172.515 NI In s s 98 (10rnrn) 89

Art In s 98 (10rnrn)

172.515 NI In s s 291 -10

172.515 NI In s MIS 179-181 (10 rnrn) 50-55 135

172.515 NI s 185-190 (16rnrn) >93

NI In s s 174 67
172.515 NI In s s 73-103 (0.8 rnrn) 36-37 71

172.515 NI VSI s s 100-102 (18 rnrn) -18 98

NI 110-112 (15 rnrn) 31 >93

172.515 NI VSI s MIS 130-131 56.3 32

172.515 NI Sl s s s 128 28

NI VSI s VS s 123-125 -10 31

NI 118-119 (15 rnrn) -21 90

172.515 NI In Sl MIS 202-203 -4 104 FCC

NI Sl s 104-135 41

NI Sl s 123 35

172.515 NI In s 47-48 (17rnrn) 38

NI 20 (20rnrn) 33
442 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

cis-4-Hexenal 3496

4-Hexene-3-one 3352 718

trans-2-Hexenoic acid 3169 4126

3-Hexenoic acid 3170 2256

1-Hexen-3-ol 1-Vinylbutan-1-ol 3608 2021

2-Hexen-1-ol trans-2-Hexenol, Leaf alcohol 2562 69

3-Hexen-1-ol cis-3-Hexenol 2563 750

4-Hexen-1-ol 4-Hexenyl alcohol 3430 2295

2-Hexen-1-yl acetate 2564 643

cis-3-Hexen-1-yl acetate 3171

cis-3-Hexenyl benzoate 3688

cis-3-Hexenyl cis-3-hexenoate 3689

cis-3-Hexenyl butyrate 3402

3-Hexenyl formate 3353 2153

cis-3-Hexenyl hexanoate 3403

cis-3-Hexenyl-cis-3-hexenoate 3689

Hexyl trans-2-Hexenoate 3692

cis-3-Hexenyl isobutyrate

3-Hexenyl isovalerate 3498 2344

cis-3-Hexenyllactate 3690

3-Hexenyl-2-methyl butanoate 3497 2345

Hexyl2-methyl-3 and 4-pentenoate 3693

3-Hexenyl phenylacetate cis-3-Hexenyl phenylacetate 3633

3-Hexenyl a-toluate

Hexyl acetate 2565 196

2-Hexyl-4-acetoxytetrahydrofuran 490
 Organic Chemicals Used in Flavorings and Fragrances 443

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Flash ,..._
Solubility
Point°C "'
C'
...c: .2
..
Classi- ~ closed cup ~
fication 0 ~- 0 unless
tJ
c: >.o <1::
European ~ "'
..c:
P..<.J
0 >. ...
"0
Boiling Point oc Melting 0 =open
·;::;
...p..
C.F.R. Countries ~ ~ ~a ~ (atmmHg) Point°C cup ~

NI 15 (105mm)

NI 136-137 32

NI Sl s s s 217 37 +67

NI 208 12

NI In s 133-134 37
(760mm)

172.515 NI VSI s s 158-161 54

172.515 NI Sl s s 156-157 44

NI SLS s 159-160 69.5 (17mm) 61

172.515 NI SIS s 67-68 (16mm) 50

N'I In s MIS 66 (16mm) 50

NI SLS s s 130 (5mm) >93

NI In s 194.1 110

NI VSI s s s 192 +67

NI VSI s s s 155 47

NI VSI s s s 112 (12mm) 110

NI

NI

Art 73 (6mm) 73

172.515 NI In s s s 199 +67

NI SLS s 90 (7mm) 93

172.515 NI In s 200 +67

Art In MIS 57-61 (2mm)

172.515 NI In s 133 (4mm) 104

172.515 NI In s 168-170 -80 37

172.515 Art VSI s s

444 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Hexyl alcohol 1-Hexanol 2567 53

Hexyl benzoate 3691 645

n-Hexyl2-butenoate Hexyl crotonate 3354

Hexyl butyrate 2568 271

a-Hexyl cinnamaldehyde 2569 129

Hexyl formate 2570 499

Hexyl-2-furoate 2571 361

Hexyl hexanoate 2572 316

2-Hexylidene cyclopentanone 2573 167

Hexyl isobutyrate 3172 646

2-Hexyl-5( or 6)-keto-1 ,4,-dioxane 2574 6003

Hexyl2-methyl-butanoate 3499

Hexyl 3-methyl-butanoate Hexyl isovalerate 3500

Hexyl octanoate Hexyl caprylate 2575 394

Hexyl phenylacetate 3457

Hexyl propionate 2576 420

Hydrogen sulfide 647

Hydroquinone monoethylether 3695 2258

2-Hydroxyacetophenone o-Acetylphenol 3548 4136

4-Hydroxybutanoic acid lactone y-Butyrolactone 3291 615

1-Hydroxy-2-butanone 3173

Hydroxycitronellal 2583 100

Hydroxycitronellal diethyl acetal 2584 44

Hydroxycitronellal dimethyl acetal 2585 45

Hydroxycitronellol 2586 559

 Organic Chemicals Used in Flavorings and Fragrances 445

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point•c "'
C'
Classi- ...c ~
closed cup
.2
fication .... 0
c ~0
0 unless
~
u
<C
European ~ "'
..c g.~ ...
"0
Boiling Point •c Melting 0 =open
·r:;
Cl)

C.F.R. Countries ~ ~ ~~ ~ (atmmHg) Point•c cup

0..
Vl

172.515 NI s s s 156-157 -52 60 FCC

NI In s 272 (760mm) >93

NI 96-98 (15mm) 89

172.515 NI SSL MIS 205 (760mm) -78 81

172.515 NI In s In s 174-176 4 >93 FCC

EOA

172.515 NI VSl s 155-156 -60 48

Art In s 105 (1mm) >110

172.515 NI In s MIS 245 -55 68

172.515 Art In s 240 (760mm) >93

NI VSl s s s 199 73

Art SIS

172.515 NI In s s 212 83

172.515 NI In s 215 88

172.515 NI In s 277 -31 +67

NI In s 262 >93

172.515 NI VSl s s MIS 73-74 (10 mm) -69 65

NI s -62 -83

Art

NI Sl s s 220 5 112

NI s vs 204 -45 98

NI s s s 152-154

172.515 Art VSl s s s 94-96 (1mm) +100 EOA

172.515 Art VSl s s s 260 +100

172.515 Art VSl s s s 252 +100 FCC

EOA

172.515 NI SLS s s 156 (15mm) +100

446 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

5-Hydroxy-2,4-decadienoic acid 3696

a-lactone

5-Hydroxy-2-decenoic acid a-lactone 3744

5-Hydroxy-7-decenoic acid a-lactone 3745

6-Hydroxydihydrotheaspirahe 3549

2-Hydroxy-2-cyclohexen-1-one 3458

4-Hydroxy-2,5-dimethyl-3(2H)-furanone Furaneol 3174 536

6-Hydroxy-3,7-dimethyloctanoic acid 3355

lactone

N-( 4-Hydroxy-3-methoxybenzyl)- Capsaicin 3404 2299

8-methyl-6-nonenamide

2-Hydroxy-4-methylbenzaldehyde 3697

2-Hydroxymethyl-6,6-dimethylbicyclo- Myrtenyl formate 3405

(3.1.1) hept-2-enyl formate

4-Hydroxy-5-methyl-3(2H)-furanone 4-Hydroxy-5-methyl-2,3-dihydrofuran- 3635

3-one

3-(Hydroxymethyl)-2-octanone 3292

Hydroxynonanoic acid a-lactone a-Nonalactone 3356 2194

5-Hydroxy-4-octanone Butyroin 2587 2045

3-Hydroxy-2-pentanone 3550

4-Hydroxy-3-pentenoic acid lactone P- Angelica lactone 3293 731

4-(p-Hydroxyphenyl)-2-butanone 2588 2046

2-Hydroxy-3,5,5-trimethyl-2- 3459
cyclohexenone

5-Hydroxyundecanoic acid lactone a-u ndecalactone 3294 688

Indole 2593 560

a-Ionol 3624
 Organic Chemicals Used in Flavorings and Fragrances 447

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c"'
.!a .52
Classi-
(I)
c closed cup
fication ... 0c ..!:!-
»0
6 unless
~
u
<C

*
c.u -o ·;::;
Boiling Point oc
<.:
European .c 0 >. (I)
Melting 0 =open (I)

C.F.R. Countries ~ ~ ~5 ~ (at mmHg) Point°C cup

c.
rJ'J

NI In s 85
(2-2.5mm)

Nl

Nl

NI In 130 (16mm)

NI s s s 53 (2.2mm) 36-38

Nl VSl s s s 78-80 70

Nl

NI Sl s 210-200 65
(hot)

NI

Art s 86

Nl SLS 126-126.5

Art In s s 182

NI VSl s s 173(11mm) >93

172.515 Nl VSl s 80-82

NI 105-107 (50mm)

NI Sl s 167-170 18

172.515 NI s >200 82-83 +100

NI SLS s 90-110 (15 mm) 90-91

NI VSL s s 152-155 >93

(10.5mm)

172.515 NI In s s s 253-254 51-54 >110 FCC

Sin Hot EOA

NI In s 75 (0.03mm)
448 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

13-Ionol 3625

a-Ionone 2594 141

13-Ionone 2595 142

y-Ionone 3175

a-Irone 2597 145

Isoamyl acetate Amyl acetate 1 2055 214

Isoamyl acetoacetate Isoamyll3-ketobutyrate 3551 277

Isoamyl alcohol 2057 51

Isoamyl benzoate Amyl benzoate• 2058 562

Isoamyl butyrate Amyl butyrate 1 2060 282

Isoamyl cinnamate Isoamyll3-phenylacrylate 2063 335

Isoamyl formate Amyl formate 1 2069 500

lsoamyl2-furanbutyrate Isoamyl furylbutyrate 2070 2080

Isoamyl2-furanpropionate Isoamyl furylpropionate 2071 2092

Isoamyl hexanoate Amyl caproate 1 2075 320

Isoamyl isobutyrate 3507 294

Isoamyl isovalerate Amyl valerate 1 2085 458

lsoamyllaurate Isoamyl dodecylate 2077 379

lsoamyl2-methylbutyrate 3505

Isoamyl nonanoate Amyl pelargonate 1 2078 391

Isoamyl octanoate Isoamyl caprylate 2080 401

Isoamyl phenylacetate Isoamyl a-toluate 2081 2161

1 Commercially, isoamyl esters are called "amyl"; normally amyl esters are designated "n-amyl."
 Organic Chemicals Used in Flavorings and Fragrances 449

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash -;;;-

Point°C C"
II) .!!l .2
Classi- c closed cup
fication ... 0
c ~0
0 unless
~
u
II:
-o ·;:;
European ~ "'
..c g.~ II)
>< Boiling Point oc Melting 0 ==open II)
0..
C.F.R. Countries ~ ~ ~0 ii: (atmmHg) Point°C cup tl:l

NI VSl s s s 121-122 115 FCC

EOA

172.515 In s s 121-122 (10mm) >93

NI VSl s s s 126-128 (12mm) >110 FCC

EOA

NI +100 EOA

172.515 NI VSl s s 110-112 (3mm) +100

172.515 NI VSl s VSl s 143 -78 25 FCC

EOA

172.515 Art In s 222-224

172.515 NI Sl s s 130 -117.2 45.5

172.515 NI In s 260-262 +100

172.515 NI VSl s In s 184-185 FCC

58 EOA

172.515 NI In s s 310 +100 EOA

172.515 NI Sl s s s 123-124 -93 53 FCC

EOA

172.515 Art In s
172.515 Art In s
172.515 NI In s In s 94-96 (lOmm) 88 FCC
EOA

172.515 NI 170 88

172.515 NI Sl s Sl s 191-194 72 FCC

(760mm)

172.515 NI In s >110

172.515 NI In s s 70-71 (Smm)

172.515 NI In s 260-265 >110

172.515 NI In s 260 104 EOA

172.515 NI In s 265-266 +100

450 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Isoamyl propionate Amyl propionate 1 2082 417

Isoamyl pyruvate 2083 431

Isoamyl salicylate Amyl salicylate 1 2084 435

Isoamyl valerate 648

Isoborneol 2158 2020

Isobornyl acetate 2160 2066

Isobornyl formate 2162 565

Isobornyl isovalerate 2166 452

Isobornyl propionate 2163 412

Isobutyl acetate 2175 195

Isobutyl acetocetate 2177 242

Isobutyl alcohol lsobutanol 2179 49

Isobutyl angelate Isobutyl cis-2-methyl-2-butenoate 2180 247

Isobutyl anthranilate 2182 253

Isobutyl benzoate 2185 567

lsobutyl2-butenoate Isobutyl crotonoate 3432

Isobutyl butyrate 2187 269

Isobutyl cinnamate 2193 327

Isobutyl formate 2197 502

Isobutyl2-furanpropionate Isobutyl furylpropionate 2198 2093

Isobutyl heptanoate Isobutyl heptylate 2200 364

Isobutyl hexanoate Isobutyl caproate 2202 314

Isobutyl isobutyrate 2189 292

1 Commercially, isoamyl esters are called "amyl"; normally amyl esters are designated "n-amyl."
 Organic Chemicals Used in Flavorings and Fragrances 451

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.9
.
Classi- OJ ..!!l closed cup
c
fication 0
c >.-o
OJ 6 unless
~
u
<.!:
-o ·c:;
"" Boiling Point oc
OJ P.,U
European .<:: 0 » OJ
Melting 0 =open
~
iZ
OJ

C.F.R. Countries ~ UJ t:\::6 (at mmHg) Point oc cup

P.
Cll

172.515 NI In s s s 160-175 41 EOA

172.515 Art SLS MIS MIS 185

172.515 NI In s VSl s FCC

277-278 >110 EOA

NI Sl s 64

172.515 NI In s s s 212-214 216 EOA

(sublimes) (sublimes)

172.515 NI In s Sl s 220-224 +100 FCC

EOA

172.515 Art In s 110 (20mm) 97

172.515 Art In s Sl 255-256 +100

172.515 NI V Sl s Poor 245 +100

172.515 NI Sl s s s 116-117 -98.6 to -99 30 (o) FCC

172.515 Art In s 84.5 (11 mm)

172.515 NI s s MIS 108 -108 28 FCC

172.515 NI VSl s 176-177 60

172.515 Art In s 169-170 >93

(13.5mm)

172.515 NI In s 240-242 96

NI 171 77

172.515 NI Sl s In s 157-158 45.5 EOA

172.515 NI VSl s s 287 >110 FCC

172.515 NI Sl MIS 97-98 -95.3 18

172.515 Art In s 105 (3mm) >93

172.515 NI s 209 +67

172.515 NI In s 196-204 76
(760mm)

172.515 NI In s 147-148 -81 49

452 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Isobutyl-3-methoxypyrazine 3132

2-Isobutyl-3-methylpyrazine 3133

a-Isobutylphenethyl alcohol Benzyl isoamyl alcohol 2208 2031

Isobutyl phenylacetate Isobutyl a-toluate 2210 2160

Isobutyl propionate 2212 406

Isobutyl salicylate 2213 434

2-Isobutyl thiazole 3134

Isobutyraldehyde 2220 92

Isbutyric acid 2222 6

Isoeugenyl acetate Acetyl isoeugenol 2470 220

Isoeugenyl benyzl ether Benzyl isoeugenol 3698 522

Isoeugenyl butyl ether Butyl isoeugenol 2151

lsoeugenyl ethyl ether Ethyl isoeugenol 2472 190

Isoeugenyl formate 2474 356

Isoeugenyl methyl ether Methyl isoeugenol 2476 186

Isoeugenyl phenylacetate 2477 237

dl-Isoleucine 2-Amino-3-methylpentanoic acid 3295

dl-lsomenthone 3460 2259

lsopentylamine 3219 512

Isophorone 3553

cis-5-lsopropenyl-cis-2-methyl- Photocitral 3645

cyclopentan-1-carboxaldehyde

lsorpopenylpyrazine 3296
 Organic Chemicals Used in Flavorings and Fragrances 453

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc
~
c
Classi-
<1)
c<1) ..!!l closed cup
.:::<;;
fication .... 0c >.o 6 unless u
<.:
o..u -o ·c::;
"' Boiling Point oc
<1)
European <;; .c 0 ;;.., <1)
Melting 0 ==open <1)
-~
C.F.R. Countries ~ CiJ ~6 LJ.. (at mmHg) Point°C cup
0..
r./)

Nl SLS s 83 (12mm) 80

NI 74 (10mm)

172.515 Art In s MIS 250

172.515 NI In s In s 253 116 FCC

EOA

172.515 NI In vs 137-138 -71 20

172.515 Nl In s In s 259 -5.9 212 FCC

EOA

172.515 NI In s 180 57

172.515 NI V Sl s 63 -66 19 FCC

172.515 NI s s s s 153-154 -47 55 FCC

172.515 Art VSI s MIS 80 +67 FCC

EOA

172.515 Art In s 284 58-59 +100

Art

172.515 Art In s MIS 245 63-64 >93

(sublimes)

172.515 Art V Sl s Sl s 282

172.515 NI In s s 262-264 16-17 +100

172.515 Art In s s >110

NI s In 292 79 FCC
(decomposes)

NI V Sl s s 210 84

NI s s MIS 95-97 18

NI Sl s 213-214 -8 84

NI In s 80-84 (11 mm)

NI In s 73-75 (17 mm)

454 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Isopropyl acetate 2926 193

p-lsopropyl acetophenone 2927 651

Isopropyl alcohol 2-Propanol 2929

Isopropyl benzoate 2932 652

p-lsopropyl benzyl alcohol Cuminic alcohol 2933 88

Isopropyl butyrate 2935 267

Isopropyl cinnamate 2939 325

Isopropyl formate 2944 503

Isopropyl hexanoate 2950 312

isopropyl isobutyrate 2937 290

Isopropyl isovalerate 2961 445

Isopropyl 2-methyl butyrate 3699

5-Isopropyl-2-methylpyrazine 2-Methyl-5-isopropylpyrazine 3554 2268

2-Isopropyl-4-methylthiazole 3555

2-Isopropyl-5-methyl-2-hexenal 3406

Isopropyl myristate Isopropyl tetradecanoate 3556 386

2-Isopropylphenol 3461

p- lsopropylphenyl acetaldehyde 2954 132

Isopropyl phenylacetate 2956 2158

3-(p-lsopropyl) phenyl propionaldehyde 2957 2261

Isopropyl propionate 2959 404

Isopropyl tiglate Isopropyl a-methyl crotonate 3229

Isopulegol p-Menth-8-en-3-ol 2962 2033

lsopulegone p-Menth-8-en-3-one 2964 2051

Isopulegyl acetate 2965 2067

 Organic Chemicals Used in Flavorings and Fragrances 455

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point•c "'
C'
Classi- ... ~ closed cup
.2
...... 0c: ...c: 0 'i()<i
fication ., »o
c..u ...
-o unless <C
·c::;
European 'i<i .c 0 ..... Boiling Point •c Melting 0 =open ...c..
C.F.R. Countries ~ U:i ~6 lZ (atmmHg) Point•c cup ell

172.515 NI s s MIS 89.4 -69 16 FCC

172.515 NI In s MIS 252-254

172.515 Nl s s s 82.4 -89.5 22 FCC

172.515 NI In s 218-219

172.515 NI VSI s s 248 >110

172.515 Nl In s s 130-131 30

172.515 Art In s s 268-270 +100

172.515 Nl Sl s s MIS 67-68 -5.5

172.515 Nl In s 176

172.515 NI In s s 121

172.515 Nl In s s 68-70 (55mm) 14

NI SLS s 81-83
(100mm)

NI

Nl SLS s 92 (50mm) 58

Nl 73 (10mm) 61

Nl In s s MIS 140.2 (2mm) Freezing pt 3 +100

NI In s 214 15-16 88

172.515 Art VSI s s 230 >93

172.515 Art In s 253

172.515 Art In s s
172.515 Nl SLS s MIS 108-110

Nl In s s 73 (30mm) 44

172.515 NI In s Sl s d, 95 (17mm) FCC

EOA

172.515 NI SLS s s 101-102 (17mm)

172.515 NI In s s 104-105 (10 mm) 87

456 Source Book of Flavors

TABLE 10-l Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Isoquinoline 2978 487

Isovaleric acid Isopropyl acetic acid 3102 8

Jasmone cis-Jasmone 3961 4148

2-Keto-4-butanethiol 4-Mercapto-2-butanone 3357

Lactic acid 2-Hydroxypropanoic acid 2611 4

Lauric acid 2614 12

Lauric aldehyde Aldehyde C-12 2615 99

Laury! acetate Dodecyl acetate 2616 200

Laury! alcohol Alcohol C-12 2617 56

!-Leucine L-2-Amino-4-methylvaleric acid 3297 4150

Levulinic acid ~-Acetylpropionic acid 2627 23

d-Limonene Dipentene 2633 491

Linalool 3,7-Dimethyl-! 1,6-octadien-3-ol 2635 61

Linalool oxide 3746 2214

Linalyl acetate 2636 203

Linalyl anthranilate 2637 256

Linalyl benzoate 2638 654

Linalyl butyrate 2639 276

Linalyl cinnamate 2641 329

Linalyl formate 2642 347

Linalyl hexanoate Linalyl caproate 2643 318

 Organic Chemicals Used in Flavorings and Fragrances 457

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Flash ,.......
Solubility
Point°C "'
C'
Classi- cu :! .51
c:: closed cup ';;
fication
European
....
~
0c::
-5"'
i"[
o_
0
-o
cu Boiling Point oc Melting
unless
0 =:open
u
<.C
·ocu
C.F.R. Countries ~ ~ C:c.:l iZ (atmmHg) Point°C cup
P-
Vl

172.515 NI VSI s MIS 243 23

172.515 NI Sl s 176 -29 70.5 FCC

172.515 NI Sl s 257-258
(755mm)

Art 59-60 (15 mm)

NI s s s 122 (15mm) 18 >230 FCC

172.860 NI In s MIS 225 (100mm) 44 >93 FCC

172.515 NI In s s s 11 FCC
185 (100mm) 101.5 EOA

172.515 NI In s s 150-151 (15 mm) >100

172.515 NI In s s s 259 FCC

260-262 22-26 >110 EOA
(260mm)

172.320 NI s VSI 145-148 293-295 FCC

(sublimes) (decomposes)

172.515 NI s s s 245-246 33-35 138

182.60 NI In s In s (dl) 176-178 -96 48 FCC

EOA

182.60 NI In s s s 78 FCC
194-197 EOA

172.515 NI s 188 (760mm) 63

182.60 NI In s Sl s FCC
220 90 EOA

172.515 Art In s In s 350 >93

172.515 NI In s s 263 98 FCC

172.515 NI In s s 80-82 (0.2mm) 103

172.515 Art In s 353 +100

172.515 NI In s Sl s 100-103 87 EOA

172.515 NI In s s 252 +100

458 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Linalyl isobutyrate 2640 298

Linalyl isovalerate 2646 449

Linalyl octanoate Linalyl caprylate 2644 397

Linalyl phenylacetate 3501 655

Linalyl propionate 2645 411

1-Malic acid "Apple acid" 2655 17

Mal to! 3-Hydroxy-2-methyl-4-pyrone 2656 148

Malty! isobutyrate 3462

p-Mentha-1 ,3-diene a-Terpinene 3558

p-Mentha-1 ,4-diene y- Terpinene 3559

p-Mentha-1 ,8-dien-7 -ol Perillyl alcohol 2664 2024

Menthadienol

p-Mentha-1-4(8)-dien-3-one Piperitenone 3560

p-Mentha-1 ,8-dien-7-yl acetate Perillyl acetate, Dihydrocuminyl acetate 3561

Menthadienyl acetate

p-Menthan-2-ol Carvomenthol 3562 2228

p-Menthan-2-one Carvomenthone 3176

p-Mentha-8-thiol-3-one 3177

p-Menth-1-ene-9-al Carvomenthenal 3178

p-Menth-1-en-3-ol Pi peri to! 3179

p-Menth-3-en-1-ol 1-Terpineol 3563

 Organic Chemicals Used in Flavorings and Fragrances 459

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Pointoc c
<U .!!l .9
Classi- c closed cup ';
0c <U 0 u
fication ....<U >-o
o.u "0
unless tC
·o
European ';
~
"'
..c 0
~6
>.
~
<U
Boiling Point ac Melting 0 =open <U
0..
C.F.R. Countries ~ (at mmHg) Pointoc cup r:ll

172.515 NI In s Sl s +100 FCC

230 EOA

172.515 NI In s s +100

172.515 NI In s s 264 +100

Art In s 317 +100

172.515 NI In s Sl s 226 87 FCC

EOA

184.1069 NI vs s I, 140 (dl) 128 FCC

(decomposes) (d&l) 99-100 (dl)

172.515 NI Sl s s 160-164 +100 FCC

Art In s 176 (7mm) 93

172.515 NI In s s 176 47

172.515 NI VSI s s 183

172.515 NI 1-, 92-53 (5 mm) +67

d-, 94 (4-5 mm)

172.515 NI 118 (10mm)

172.515 NI VSI s s 233

172.515 NI VSI s s +67

172.515 NI 85 (0.6mm)

NI 222, 101.8-102 >93

(14mm)

NI s 75 (2.5mm)

NI In s 56 (0.1mm) 108

NI trans dl, 66-69

(0.2mm) dl

NI 232 cis-1-36,
cis-d,l 28

172.515 NI Sl s s s 210
460 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

p-Mentha-8-en-1-ol ~-Terpineol 3564

p-Mentha-8-en-2-one cis-Dihydrocarvone 3565

1-p-Menthen-9-yl acetate 3566

Menthol (1 and dl forms) 3-p-Menthanol 2665 63

d-neo-Menthol 2666 2028

Menthone p-Menthan-3-one 2667 2035

p-Methoxycinnamaldehyde p-Cumaricaldehyde methylether 3567

Menthyl acetate 2668 206

Menthyl Lactate 3748

Menthyl isovalerate Menthol valerate 2669 450

Validol

2-Mercapto-3-butanol 3502 760

3-Mercapto-2-butanone 3298

2-Mercaptomethyl pyrazine 3299

2-Mercapto-2-pentanone 3300 2327

2,3 or 10-Mercaptopinane 3503 2332

2-Mercaptopropionic acid Thiolactic acid 3180

1-p-Methene-8-thiol 3700

d)-Methionine 3301 569

p-Methoxybenzaldehyde Anisic aldehyde 2670 103

Aubepine

o-Methoxybenzaldehyde o-Anisaldehyde

o-Methoxycinnamaldehyde 3181 571

(2,5 or 6)-Methoxy-3-ethyl-pyrazine 3280

 Organic Chemicals Used in Flavorings and Fragrances 461

TABLE 10·1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-...

~
Point°C c
Classi- OJ
c ~ closed cup
.2
0 'iii
fication ... 0
c
,!!_
0>-.0
c..u "'0 unless <C
(,)

·c:;
European B OS
..c 0 ;>.. OJ
Boiling Point oc Melting 0 =-open
OS >< OJ
C.F.R. Countries ~ Ill c':G li: (atmmHg) Point°C cup
c.
Cll

172.515 NI VSI s s s 210 cis, 36

trans,
32-33

172.515 NI In s s 222 89

172.515 NI

172.515 N Sl vs s 216 >28 93 FCC

172.515 NI Sl vs >93

172.515 NI In s s 207-210 72

NI VSI s s 277 58 >93

172.515 Nl s s 228-229 92

Art IN s s 38-40

172.515 NI In s s 241 120

Art In MIS MIS 58-60 (10mm)

Art Sl s 50 (18mm)

Art 44-45 (0.07 mm)

Art In MIS 57 (15mm)

Art In s s
Art s s 102 (16mm) 10-14 88

NI

Nl s VSI 281
(decomposes)

172.515 Nl In s s s 248 2.5 121 FCC

EOA

172.515 NI VSI s MIS 238 38-39 117

172.515 NI VSI s s 295 44-45 >93

(decomposes)

Nl 64
462 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Methoxy-(3,5 or 6)-isopropylpyrazine 3358

p-Methoxy-a-methyl cinnamaldehyde 3182 584

2 (5 or 6)-Methoxy-3-methylpyrazine 3183 2266

(mixture)

2-Methoxy-4-methylphenol Creosol 2671 175

2-Methoxy-3-(1-methylpropyl) pyrazine 3433

4 (p-Methoxyphenyl)-2-butanone Raspberry ketone methyl ether 2672 163

1-(4-Methoxyphenyl)-4-methyl-1-penten- 3760
3-one

1-(p-Methoxyphenyl)l1-penten-3-one 2673 164

1-(p-Methoxyphenyl)2-propanone 2674 2047

2-Methoxy-4-propylphenol Dihydroeugenol 3598

4-Propyl guaiacol

Methoxypyrazine 3302

2-Methoxy-4-vinylphenol p-vinylguaiacol 2675 177

Methyl acetate 2676 213

4-Methylacetophenone 2677 156

Methyl1-acetoxycyclohexyl Ketone 3701

1-Methyl-2-acetylpyrrole 3184

2-Methylallyl butyrate 2678 572

Methylated Silica 3182

Methyl anisate 2679 248

o- Methylanisole 2680 187

p- Methylanisole Methyl p-cresol 2681 188

Methyl anthranilate Methyi2-Aminobenzoate 2682 250

 Organic Chemicals Used in Flavorings and Fragrances 463

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C "'
C"
11.1
~
.!2
Classi- c closed cup Oj
0
fication ... 0
cOS
11.1
>.o -o unless
·o"'11.1
II:
Boiling Point oc
O..t.l
European ~ ..c 0 ;>, 11.1
>< Melting 0 =open
C.F.R. Countries i3: ~ C::6 l.i:: (atmmHg) Point°C cup
0..
Cll

Art 80 (25mm) 63

Art In In 106-109 >93

(0.1 mm)

Art 48-50 (15 mm) 55

172.515 NI Sl s 221-222 5.5 99.5

NI 78

172.515 NI VSI s Poor 152-153 (15 mm) 8-10 >110

172.515 Art VSI s Poor s 217-219 28

172.515 Art In s Poor s 278 (12mm) 60

172.515 NI VSI s s 145 (25mm) 101.5

NI SLS s 125-126 (14mm) >110

NI In s 60-61 (29mm) 45.5

172.515 NI In s 100 (5mm) 8

172.515 In s s MIS 57-58 -98 -9

172.515 NI In s Sl s 225 22-24 92

Art In MIS 67 (3mm)

NI 88-93 (22 mm)

Art In s s 168

172.515 NI In s 244-245 48-52 >110

172.515 NI In s s 166-167 51

172.515 NI In s In s 174 53 FCC

EOA

182.60 NI s s s s 256 24-25 104 FCC

EOA
464 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Methyl benzoate 2683 260

a-Methylbenzyl acetate 2684 573

Methylbenzyl acetate (mixed o.m.p.) 3702

a-Methylbenzyl alcohol a-Phenylethyl alcohol 2685 2030

a-Methylbenzyl butyrate 2686 2083

Methylbenzyl disulfide 3504

a-Methylbenzyl formate 2688 574

a-Methylbenzyl isobutyrate 2687 2088

a-Methylbenzyl propionate 2689 425

4-Methylbiphenyl 3186 2292

2-Methyl-1-butanethiol 3303

3-Methyl-2-butanethiol 3304

3-Methyl-2-butanol 3703

2-Methyl-2-butenal Tiglic aldehyde 3407

trans-2-Methyl-2-butenoic acid 2-Methylcrotonic acid 3599

Tiglicacid

3-Methyl-2-butenal 3-Methylcrotonaldehyde 3646

Senecialdehyde

3-Methyl-2-buten-1-ol Phenol 3647

2-Methylbutyl acetate 3644

2-Methylbutyl isovalerate 3506

3-Methylbutyl2-methylbutanoate 3505

2-Methylbutyl3-methylbutanoate 3506

2-Methylbutyl2-methylbutyrate 3359
 Organic Chemicals Used in Flavorings and Fragrances 465

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash
.., Point oc c'"""'
"'
.52
.!!l
Classi- ..,c 6 closed cup 'iiiu
fication ..,... 0
c :;;:.,-o
c..u ..,
"0
unless <.:
·o..,
European 'iii "'
.<: 0 >. >< Boiling Point oc Melting 0 =open
C.P.R. Countries ~ LiJ t:\:6 i.i: (at mmHg) Point°C cup
c.
(/J

172.515 NI VSl s s s 197 -12 to -13 82 FCC

EOA

172.515 In s s s 94-95 (12 mm) 91 FCC

NI EOA

172.515 Nl s Sl s
172.515 NI In s s s 204 20 85 FCC
EOA

172.515 Art VSl s s 83-84 (3mm) 109

NI In 82-86 (0.8 mm)

172.515 Art In s s
172.515 Nl VSl s s 110 (14mm) >93

172.515 Art In s s 91-92 (5mm) 94.5

Art In 267-268 45-50 >110

NI 118 -1 19

NI In s 118 18 5.5

NI SLS MIS s 112-114 27

Nl SLS s s 118 18

NI SLS In 95-96 (12mm) 63-67

172.515 NI SLS s 133-135 34

172.515 NI In s 48-49 (12 mm) 43

NI In s s 229

172.515 NI In s MIS 190-194 61.5

172.515 Nl In s s 70-71 (8mm)

172.515 Nl In s s 192 66

NI In s s 70-72 (11 mm) 67

466 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

3-Methylbutyl2-methylpropanoate 3507 294

Methyl p-tert-butylphenyl acetate 2690 577

2-Methylbutyraldehyde 2691 575

3-Methylbutyraldehyde lsovaleraldehyde 2692 94

Methyl butyrate 2693 263

2-Methyl butyric acid 2695 2002

a-Methyl cinnamaldehyde 2-Methyl-3-phenyl-2-propen-1-al 2697 578

p-Methyl cinnamaldehyde 3(p-Methylphenyl) propenal 3640

Methyl cinnamate Methyl-3-phenyl-propenoate 2698 333

6-Methyl coumarin Tonkarine 2699 579

3-Methyl crotonic acid Senecioic acid 3187

2-Methyl-1, 3-cyclohexadiene

1-Methyl-2 3-cyclohexadione 3305 2311

Methyl cyclohexanecarboxylate 3568

3-Methyl-2-cyclohexen-1-one 3360

3-Methyl-1-cyclopentadecanone di-Muscone 3434

Methylcyclopentenolone Cyclotene 2700 758

1-Methyl-1-cyclopenten-3-one 3435

5H-5-Methyl-6, 7-dihydrocyclopenta-(b )- 3306 2314

pyrazine

Methyl dihydrojasmonate 3408

Methyl-3, 7-dimethyl-6-octenoate Methyl citronellate 3361

4-Methyl-2,6-dimethoxyphenol 3704

2-Methyl-! ,3-dithiolane 3705

 Organic Chemicals Used in Flavorings and Fragrances 467

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash
Point oc c"'
0,) ..;!l .2
Classi- c0,) closed cup
fication .... 0 >.o
6 unless
~
u
c c..u -o0,) <.C
·u
" Boiling Point oc
0,)
European ~ ..c 0 >. >< Melting 0 =open 0,)
c..
C.F.R. Countries ~ LiJ ~6 ~ (at mmHg) Point°C cup VJ

172.515 NI In MIS 170 58

172.515 Art+ VSl s s s 106 (2mm) >110

172.515 NI Sl s s s 90-92 <-60 4.5

172.515 NI V Sl s s s 90 -51 -2

172.515 NI s s 102-103 -85 12

172.515 NI Sl s s 102-103 dl-, 174 71

172.515 NI In s s s 148 (27mm) 79 FCC

EOA

172.515 Art 154 (25mm) 41.5

172.515 NI In s s s 254-255 36 +100 FCC

EOA

Art VSl s s 303 (725mm) 90 >93

(hot)

NI In s s s 194-195 69-71

172.515 NI In vs 110 107-108

NI s 67-72 (lmm) 61-63

NI In MIS 183 60

NI 199 -21 68

Nl V Sl MIS s 130 (0.5mm) +66

172.515 Nl s s s 105-107 +100 FCC

(hot)

NI s s s Sl 74 (15mm) 65.5

NI V Sl s s 96-99 (20mm) 121-123 79

NI VSl s s >300 >93

NI V Sl s s 216

NI In s 141 (6mm)

NI In SLS 65 (10mm)
468 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Methyl disulfide Dimethyl disulfide 3536 2175

4-(3,4-Methylenedioxyphenyl)-2- Piperonyl acetone 2701 165

butanone

2-Methyl-3,5 or 6-ethoxypyrazine 3569

2-Methyl-3-furanthiol 3188

5-Methyl furfural a-Methyl furfural 2702 119

Methyl furfuryl disulfide 3362

2-Methyl-3 (or 5, or 6)-furfuryl- 3189 2287

thiopyrazine (mixed isomers)

Methyl2-furoate 2703 358

2-Methyl-3-furylacrolein 2704 2216

3-(5-Methyl-2-furyl)-butanal 3307

3-[ (2-Methyl-3-furyl) thio J-4-heptanone 1,3-Diethylacetonyl-3-methyl-3-furyl 3570

sulfide

4-[ (2-Methyl-3-furyl) thio ]-5-nonanone 3571

6-Methyl-3,5-heptadien-2-one Methyl heptadienone 3363 4173

Methyl heptanoate Methyl heptylate 2705 368

2-Methylheptanoic acid Isocaprylic acid 2706 2003

6-Methyl-5-hepten-2-one Methyl heptenone 2707 149

5-Methyl-2 3-hexanedione 3190

Methyl hexanoate Methyl caproate 2708 319

2-Methyl hexanoic acid 3191 582

5-Methylhexanoic acid 3572

Methyl2-hexenoate 2709 583

Methyl 3-hexenoate 3364

5-Methyl-5-hexen-2-one 3365
 Organic Chemicals Used in Flavorings and Fragrances 469

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ----

c:
cJ>

Point oc
..:!l .2
Classi-
<!)
c closed cup 'Cil
0c 6 u
>--o
<!)
fication .... -o<!) unless ~
o..u ·c
Boiling Point oc
<!) ~
European 'Cil ..c 0 » .~
Melting 0 =open <!)

Cil ~6 0..
C.F.R. Countries ~
"" (at mmHg) Point°C cup r/J

172.515 NI VSI s s 116-118 -85 24

NI In s s 55 +100

Art In MIS 55 (1 mm) 65.5

NI

Nl s vs s s 187 72

NI 60-61 (0.8mm) 90

Art 153-156 (10 mm)

NI In s s 181 73

NI In s 225 103

Art 88-91 (12 mm)

Art In s 85-86 (0.3 mm)

Art In s s 190

172.515 Nl VSI s s 90 63

172.515 NI SLS s s 172-173 -55.8 53

172.515 Nl VSI s s 140 (30mm) 15 >110

172.515 NI In s s 73 (18mm) -67.1 50 FCC

NI Sl s s 138

172.515 NI In s 151 -71 45

NI s s s s 105 (5mm) 102

NI SLS MIS 112 (13mm)

172.515 Nl V Sl s s 56-58

NI 45 (10mm)

Art 148-149
470 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

5-Methyl-3-hexen-2-one 3409

Methyl p-hydroxybenzoate 2710 657

Methyl3-hydroxyhexanoate 3508

Methyl2-hydroxy-4-methylpentanoate 3706

Methyl2-methylpentanoate 3707

a-Methyl-~-hydroxypropyl-a-methyl-~- 3509 2353

mercaptopropyl sulfide

Methyl-a-ionone 2711 143

Methyl-~-ionone 2712 144

Methyl-15-ionone lsomethyl-~-ionone 2713 2145

a-iso-Methylionone y-Methylionone 2714 169

Methyl isobutyrate 2694 287

2-Methyl-3-(p-isopropylphenyl) 2743 133

propionaldehyde

2-Methyl-5-isopropylpyrazine 2268

Methyl isovalerate 2753 457

Methyl jasmonate 3410

Methyllaurate Methyl dodecanoate 2715 377

Methyllinoleate (48% )/linolenate (52%) 3411 713

mixture

Methyl mercaptan Methanethiol 2716 475

Methyl o-methoxybenzoate Methyl a-anisate 2717 2192

1-Methyl-3-methoxy-4-isopropyl benzene 3436

2-Methyl-5-methoxythiazole 3192 736

Methyl N-methylanthranilate Dimethyl anthranilate 2718 2105

 Organic Chemicals Used in Flavorings and Fragrances 471

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

,-...
Solubility Flash
Point°C c.5!"'
. closed cup
G)
Classi- c:: ~ ~
0 G) 0 u
fication c:: >.o "0
unless <J:
·;:;
"' Boiling Point oc
G) P.,U
European ~ .c 0 .... G)
Melting 0 =open G)

C.F.R. Countries :?> iii &::6 ~ (at mmHg) Point°C cup

Po.
Vl

NI 77.5 (50mm) 43

172.515 NI SLS s 270 127

(decomposes)

NI In In 85

NI

NI

Art In s SLS 80 (6mm) >93

172.515 Art In s s 238 +100

172.515 Art In s s 242 +100

172.515 Art In s 232 +100

172.515 Art SLS s s 238 +100

172.515 NI Sl s MIS 92-93 -85 1

172.515 Nl In s s 270 190

NI

172.515 NI In s s s 116-117 26

NI VSI s s 94 (0.05mm) >93

172.515 NI In s s s 148 (18mm) 5 >110

NI In s 210-212 -35

172.515 NI VSI s (gas; liquid -121 <20° (0)

under pressure)
6.1-6.2
(727mm)

172.515 NI In s 248 >110

NI In s 215

Art 117 (34mm)

172.515 NI In s s s 256 18.5 91

472 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Methyl 2-methylbutyrate 2719 2085

Methyl2-methyl-3-furyl disulfide 3573

Methyl2-(methylthio) butyrate 3708

Methyl4-(methylthio) butyrate 3412

2-Methyl-5-(methylthio) furan 3366

Methyl 3-methylthiopropionate 2720 428

Methyl 4-methylvalerate Methyl isocaproate 2721 322

Methyl myristate 2722 387

1-Methylnaphthalene 3193

Methyl ~-naphthyl ketone 2'-Acetonaphthone 2723 147

Methyl nicotinate 3709

Methyl nonanoate Methyl pelargonate 2724 389

4-Methylnonanoic acid 3574

Methyl2-nonenoate 2725 2099

Methyl3-nonenoate 3710

Methyl2-nonynoate Methyl octine carbonate 2726 479

2-Methyloctanal 2727 113

2-Methyl-2-octenal 3711

Methyl octanoate Methyl caprylate 2728 398

4-Methyloctanoic acid 3575

Methyl cis-4-octenoate 3367

Methyl trans-2-octenoate 3712

Methyl2-octynoate Methyl heptine carbonate 2729 481

Methyl2-oxo-3-methylpentanoate 3713
 Organic Chemicals Used in Flavorings and Fragrances 473

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.!!l .!2
Classi-
Q)
cQ) closed cup 'i(,)C
fication ... 0c >.c: 6 unless <C
o..u "0 ·u
Boiling Point oc
Q)
European 'iC
~
..c 0 >,
Q)
.~
Melting 0 =open Q)
0..
C.F.R. Countries ~ til ~6 ~ (at mmHg) Point°C cup ell

172.515 NI VSI s s 115-116 33

NI In s 72.5-7.5 79
(5.5mm)

NI

Art 52 (3mm) 84

NI In s 80 (45-50mm) 40

172.515 NI VSI s 74-75 (13 mm) 72

172.515 NI In s s 139-140 39.5

172.515 NI In s s 323 18-19 >110

NI In vs 240-243 -22 82

172.515 Art In vs Sl s 300-301 53 >110 FCC

EOA

NI SLS s 209 (760mm) 41

172.515 NI In s s 213.5 -35

NI In s s 95 (0.01mm)

172.515 NI In s s 115 (21mm) 91

NI SLS s 91

172.515 Art In s s 232 +100

172.515 Art In s s 82-83

NI In SLS 70-75 (8mm)

172.515 Art In s s 194-195 -40 73

NI In s 149 (22mm) >110

NI Sl s 71-72 (11mm) +67

NI SLS s 80 (12mm)

172.515 Art In s Sl s 217-220 215 89 FCC

EOA

Art SLS s
474 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Methylpentanal 2-Methyl valeraldehyde 3413 706

4-Methyl-2,3-pentanedione 2730 2043

3-Methyl pentanoic acid 3437

4-Methyl pentanoic acid 3463

4-Methyl-2-pentanone Methyl isobutyl ketone 2731 151

2-Methyl-2-pentenal 3194 2129

4-Methyl-2-pentenal 3510

2-Methyl-2-pentenoic acid 3195

2-Methyl-3-pentenoic acid 3464

2-Methyl-4-pentenoic acid 3511

4-Methyl-3-penten-2-one Mesiryloxide 3368

4-Methyl-4-penten-2-one 658

4-Methyl-2-pentyl-1 ,3-dioxolane 2-Amyl-4-methyl-1 ,3-dioxolane 3630

13-Methylphenethyl alcohol Hydrotropic alcohol 2732 2257

a-Methylphenethyl butyrate 3197 2276

Methylphenethyl ether Phenyl ethyl methyl ether 3198

Methylphenylacetate Methyl-a-toluate 2733 2155

2-Methyl-4-phenyl-2-butanol Dimethyl phenylethyl carbinol 3629

3-Methyl-4-phenyl-3-butene-2-one Benzilidene methyl acetone 2734 161

2-Methyl-4-phenyl-2-butyl acetate 2735 219

2-Methyl-4-phenyl-2-butyl isobutyrate 2736 2086

2-Methyl-4-phenyl butyraldehyde 2-Methyl-4-phenyl butanal 2737 134

3-Methyl-2-phenyl butyraldehyde 3-Methyl-2-phenyl butanal 2738 135

Methyl 4-phenylbutyrate 2739 308

3-Methyl-2-(2-pentenyl)-2-cyclopenten- 3196 4148

l-one
 Organic Chemicals Used in Flavorings and Fragrances 475

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

,-..
Solubility Flash
Point°C "'
1:'
.2
closed cup
.
OJ ~
Classi- r:: <;;
fication 0
r::
OJ
~0
6 unless
u
<C
-oOJ ·c:;
Boiling Point oc
o..u
European ~
~
"' 0 ...
,:~:;a ~
Melting 0 =open OJ
0..
C.F.R. Countries ~ (atmmHg) Point°C cup Vl

NI Sl 119-120 16.5

172.515 NI 116 -2.4 79

NI s MIS MIS 196-197

NI SLS s MIS 199-201 33 97

172.515 NI Sl s MIS 117-118 -80.4 13 FCC

NI In s s 136 38

NI SLS s 126-130

NI VSl s s 123-125 (30mm) 24-26 108

NI VSl s 80 (2mm) >93

Art VSl s MIS 197 107

NI Sl vs 129 -53 30

NI

Art In s 68 (10mm)

172.515 Art SLS MIS 113-114 (14 mm) +67

Art In 70 (0.05mm) 80

NI VSl s s 185-186 66 FCC

172.515 NI In s In s 218 90.5 FCC

EOA

Art SLS s 238 29.8 >93

172.515 Art In s 124-125 (10 mm) 38-40

172.515 Art In s s 275 +100

172.515 Art In s s 250

Art In s
172.515 Art In s 238

172.515 Art VSl s MIS

172.515 NI SLS s s 146 >93

476 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

5-Methyl-2-phenyl-2-hexenal 3199

4-Methyl-1-phenyl-2-pentanone Isobutyl benzyl ketone 2740 159

4-Methyl-2-phenyl-2-pentenal 3200

Methyl3-phenylpropionate Methyl dihydrocinnamate 2741 427

Methyl propenyl disulfide Methyl1-propenyl disulfide 3576

Methyl propionate 2742 415

3-Methyl-5-propyl-2-cyclohexen-1-one "Celery ketone" 3577

Methyl propyl disulfide 3201 585

2-Methyl-4-propyl-1 ,3-oxathiane 3578

2-Methylpropyl3-methylbutyrate Isobutyl isovalerate 3369 568

2-(2-Methylpropyl) pyridine 2-lsobutyl pyridine 3370

3-(2-Methylpropyl) pyridine 3371

2-(1-Methylpropyl) thiazole 3372

Methyl propyl trisulfide 3308 586

2-Methyl pyrazine Methyl pyrazine 3309 2270

Methyl 2-pyrrole ketone 2-Acetopyrrole 3202

6-Methylquinoline 2744 2339

5-Methylquinoxaline 3203 2271

Methyl salicylate 2745 433

Methyl sorbate 3714

Methyl sulfide Dimethyl sulfide 2746 483

2-Methyl-tetrahydrofuran-3-one 3373 2338

2-Methyl-tetrahydrothiophen-3-one 3512

4-Methyl-5-thiazoleethanol 3204

4-Methylthiazole 3716

4-Methyl-5-thiazoleethanyl acetate 3205

 Organic Chemicals Used in Flavorings and Fragrances 477

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Flash
Solubility
.., Point°C c""""'
:a .2
Classi-
0
..,= 6
closed cup 'iuii
>.-o unless
"'=
fication ....
European ~ ..c:
P,.U
0 >,
..,
~
Boiling Point oc Melting 0 =open
IC
·u..,
C.F.R. Countries ~ lil ~6 ~ (atmmHg) Point°C cup Vl
P-

NI 96-100 (0.7 mm) >110

172.515 Art VSI s Sl s 250-251 105

NI 82-87 (0.7mm) >93

172.515 NI vs s 91-92 (4mm) >100

NI 53-98 (14mm)

172.515 NI Sl s s MIS 79 -88 6

172.515 Art In s s 242-243

NI VSI s s 69-71 (43mm) 43

NI In MIS MIS 89-90 (12 mm)

NI In s MIS 171 50

NI 181 21

Art 68 (8mm)

NI In 75-80 (30mm) 59.5

NI 52 (1.2mm)

NI s s s 136-137 -29 50

NI s s s 220 85-90

172.515 NI V Sl s s 266 -22 +100

NI 120 (15 mm) 20-21 >110

NI Sl s s s 222 -8 to -7 >110 FCC

NI SLS s 67(12mm)

172.515 NI In s 38 -98 -36

NI SLS 139 -8.6 to -8.3 39.5

NI In s s 82 (28mm) 71

NI vs s s 135 (7mm) 103 (1mm) >110

NI

Art 117-118 (6mm) >110

478 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Methylthioacetaldehyde 3206

2-Methyl-3-thioacetoxy-4,5-dihydro-furan 2-Methyl-4,5-dihydro-3-furanthiol 3636

acetate

3-Methylthiobutanal 3-Methylthio butyraldehyde 3374

4-Methylthiobutanal 3414

4-(Methylthio) butanol 3600

1-Methylthio-2-butanone 3207

4-Methylthio-2-butanone 3375

Methyl thiobutyrate 3310 2328

Methylthiofuroate 3311

3-Methylthio-1-hexanol 3438

2-[ (Methylthio )methyl)-2-butenal 2-Ethylidene methionol 3601

2-(Methylthiomethyl)-3-phenylpropenal 3717
& benzylidene methional

4-Methylthio-4-methyl-2-pentanone 3376

Methylthio-methylpyrazine (mixed 3208 2290

isomers)

5-Methyl-2-thiophenecarboxaldehyde 5-Methyl-2-thenaldehyde 3209

2-Methylthiophenol o- Toluenethiol 3240 2272

o-Methylthiophenol 1-Thioguaiacol 3210

3-Methylthiopropanol Methionol 3415

3-Methylthiopropionaldehyde Methional 2747 125

3-Methylthiopropyl isothiocyanate 3312 2326

2-Methyl-3-tolylpropionaldehyde (mixed, 2748 587

but mostly p isomer)

3-Methyl-1 ,2,4-trithiane 3718

2-Methyl undecanal Aldehyde C-12 MNA 2749 2010

 Organic Chemicals Used in Flavorings and Fragrances 479

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c"'
Classi- Q) .!!l .52
c closed cup
fication .... 0c ..!:!-
»o
0 unless
'i;j
u
<!:
-o ·u
Boiling Point oc
Q) C\:1
European 'i;j -5 g.~ Q)
:.< Melting 0 =open Q)

C.F.R. Countries ~ ~ li:c;) li: (atmmHg) Point°C cup

Q.
(/)

NI 70

NI s 40-42 (0.1 mm)

NI 62-64 (10mm) 62

Art

NI s s 95-98 (20mm) 102

NI 52-53 (8mm)

NI 105-107 (55mm) 72

NI 142-143 34.5
(757mm)

NI 63 (2mm) 94

NI In 61-62 (10 mm) 108

NI In s 77 (5mm)

Art

Art 84 (12mm)

Art +67

NI 113-114 (25mm) 87

NI 105 (22mm)

NI 103-104 (21 mm) 95.5

NI SI s s s 195 88

172.515 NI VSI s s s 165 21

NI 116 (9mm) 87

172.515 Art VSI s

NI In s
172.515 NI In s MIS MIS 232 86 FCC
480 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Methyl 9-undecenoate 2750 2101

Methyl undecyl ketone 2-Tridecanone 3388

Methyl2-undecynoate Methyl decyne carbonate 2751 2111

Methyl valerate Methyl pentanoate 2752 588

2-Methylvaleric acid 2754 31

2-Methyl-5-vinylpyrazine 3211

4-Methyl-5-vinylthiazole 3313

Monosodium glutamate MSG 2756 4186

Myrcene 2762 2197

Myristaldehyde Aldehyde C-14 2763 118

Myristic acid Tetradecanoic acid 2764 16

Myrtenol 3439

2(3H)-Naphthalenone,4,4-a-5,6- 3715
tetrahydro-7 -methyl

2-Naphthalenthiol 2-Naphthyl mercaptan 3314 2330

~-Naphthyl anthranilate 2767 2170

~-Naphthyl ethyl ether "Bromelia" 2768 2058

Nero lin

~-Naphthyl isobutyl ether 3719 2273

~-Naphthyl methyl ether "Yarayara"

Nero! Geraniol cis isomer 2770 2018

Nero! oxide 3661

Nerolidol 2772 67

Neryl acetate 2773 2061

 Organic Chemicals Used in Flavorings and Fragrances 481

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c"'
0 :a .9
Classi- c closed cup ':;j
fication ...0 0c 0
>.-o 6 unless u
<C
-o ·c;
Boiling Point oc
<U P-U
European ':;j .c 0 ;.., 0
Melting 0 =open II)

C.F.R. Countries ~ U:l ~6 tE (atmmHg) Point°C cup

P-
ell

172.515 NI In s s 247-248 -27.5 +100

NI In s s 263 28-29 +100

172.515 Art In s s 230 110

172.515 NI VSI s s s 128 22

172.515 NI s s MIS 194-196 <-85 91

NI s 65-66 (12mm)

Nl s 78-80 (25 mm) -15 70.5

172.320 Nl vs Sl +100 FCC

172.515 Nl In s s 167 37

172.515 NI In s 260 23 +100

172.860 NI In s s s 326 54.4 +100 FCC

NI In s s 218 (771mm) 89

Art

NI Sl vs 285 79-84
(decomposes)

Art 340 >93

Art In s VSl s 282 37 +100 EOA

Art In s 307 >93

Art In s Sl s 274 72 +100 EOA

(sublimes)

172.515 NI In s s 225-226 +100 FCC

NI 70

172.515 NI In s s s 145 (12mm) >93 FCC

EOA

172.515 NI SIS s s 231 +100

482 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Neryl butyrate 2774 505

Neryl formate 2776 2060

Neryl isobutyrate 2775 299

Neryl isovalerate 2778 508

Neryl propionate 2777 509

Nitrous oxide 2779

2, 4-Nonadienal 3212 732

Nona-2-trans-6-cis-dienal 3377 659

2,6-Nonadienal diethyl acetal 3378 660

2,6-Nonadien-1-ol "Cucumber alcohol" 2780 589

1,4-Nonanediol diacetate 3579

y-Nonalactone so-called Aldehyde C-18, Coconut 2781 178

aldehyde

Nonanal Aldehyde C-9, Pelargonic aldehyde 2782 114

1,3-Nonanediol acetate (mixed esters) 2783 2075

1,9-Nonanedithiol 3513

Nonanoic acid 2784 29

2-Nonanol 3315 4189

3-Nonanon-1-yl acetate 2786

2-Nonanone Methyl heptyl ketone 2785 154

3-Nonanone Ethyl hexyl ketone 3440

Nonanoly-4-hydroxy-3-methoxy- 2787 590

benzylamide

2-Nonenal Heptylidene aldehyde 3213 733

6-Nonenal cii"-6-Nonenal 3580 661

trans-2-Nonen-1-ol 3379
 Organic Chemicals Used in Flavorings and Fragrances 483

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point•c "'
'C'
Q) .!!l .52
Classi- c closed cup 't;j
fication .... 0
c
Q)

>.o 0 unless
<..>
<::::
"0 ·;:;
"'
Q) Q..<..>
European 't;j .c 0 ...... Q)
X Boiling Point •c Melting 0 =open Q)

C.F.R. Countries ~ ~ ~6 Li: (atmmHg) Point•c cup

Q..
Cll

172.515 NI In s s 239-240 +100

172.515 NI VSl s s 225 92

172.515 NI VSl s s 229 >110

172.515 NI In s s 252 +100

172.515 NI VSl s s 233 +100

184.1545

NI s s 95 (2mm) 91

NI VSl s s s 187

Art VSl s s 67-70 (0.2mm) +67

172.515 NI VSl s s s 196

Art +100

172.515 NI In s s s 121-122 (6mm) >110 FCC

EOA

172.515 NI In s s s 93 (23mm) 64 FCC

172.515 Art Sl s s +100

Art In MIS 284 101.5

172.515 NI In s s 268-269 31-32 100

NI In s s 193-194 82

172.515 NI VSl s s s
172.515 NI In s s 194-196 64

NI In s MIS 190 66

172.515 NI SLS s >93

NI In s s 189 +67 FCC

NI In s 83 (17mm) 50

NI 108-110 (17mm) 102

484 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

cis-2-Nonen-1-ol 3720

cis-6-Nonen-1-ol 3465

Nonyl acetate 2788 198

Nonyl alcohol AlcohoiC-9 2789 55

Nonyl isovalerate 2791 447

Nonyl octanoate Nonyl caprylate 2790 396

Nootkatone 5,6-Dimethyl-8-isopropenyl-bicyclo- 3166

(4,4,0)-dec-1-en-3-one

Ocimene 3539

9,12-0ctadecadienoic acid 48% and 9, 3380

12,15-octadecatrienoic acid 52%
mixture

2-trans-6-trans-octadienal 3466

y-Octalactone 2796 2274

1>-0ctalactone 3214 2195

trans trans-2,4-octadienal 3721

n-Octanal Aldehyde C-8 2797 97

Caprylic aldehyde

Octanal dimethyl acetal 2798 42

1,8-0ctanedithiol 3514 2331

Octanoic acid Caprylic acid 2799 10

1-n-Octanol AlcohoiC-8 2800 54

n-Octyl alcohol

2-n-Octanol sec-n-octyl alcohol 2801 71

3-0ctanol d-n-octyl alcohol 3581

2-0ctanone Methyl hexyl ketone 2802 153

3-0ctanone Amyl ethyl ketone 2803 2042

3-0ctanon-1-ol 2804 592

 Organic Chemicals Used in Flavorings and Fragrances 485

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c.s"'
<!) ,.;!l
Classi- c: closed cup
fication .... 0
c:
<!)

>--o 6 unless
~
u
c.:
"0 ·o
Boiling Point oc
o.u
"'
<!)
European ..c: 0 >,
<!)
Melting 0"' open
~
w >< <!)

C.F.R. Countries ~ t:\:6 li: (at mmHg) Point°C cup

0.
Vl

NI SLS s 96 (10mm)

NI In 85 (5mm) +67

172.515 NI In s MIS 212 +67 FCC

172.515 NI V Sl s s 214-215 -8 to -6 76 FCC

172.515 NI In s s 264 +100

172.515 NI In s 315 +100

172.515 NI In s s 73-103 (0.8 mm) 36-37

172.515 NI In s s 177 40

NI V Sl s s >200 +100

NI In s s
172.515 NI Sl s s 234 +100

NI 104 (3mm) +100

NI In MIS 67 (0.4mm) 79

172.515 NI In s s s 171 12-15 51.5 FCC

EOA

172.515 Art V Sl s 185

Art In MIS 269-270 0.9 >110

184.1025 NI Sl s s 238 16 >110 FCC

(hot)

172.515 NI Sl s s 196 -15.4to 81 FCC

-16.3 EOA

172.515 NI In s s 179-180 -38.6 71

172.515 NI V Sl s s 174-176 65.5

172.515 NI In s s s 173.5 -16 63

172.515 NI V Sl s s s 167-168 -38.6 46

172.515 Art VSI s 94.6 (8-9mm)

486 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-0ctenal 3215 663

cis-5-0ctenal 3749

6-0ctenal 664

1-0cten-3-ol Amyl vinyl carbinol 2805 72

cis-3-0cten-1-ol 3467

cis-5-0cten-1-ol 3722

3-0cten-2-ol 3602

3-0cten-2-one 3416

2-0cten-4-one 3603 2313

1-0cten-3-one 3515 2312

3-0cten-4-one Butyl propenyl ketone 3603 2313

trans-2-0cten-1-yl acetate 3516

1-0cten-3-yl acetate Octenyl acetate 3582

1-0cten-3-yl butyrate 3612

trans-2-0cten-1-yl butanoate 3517

Octyl acetate 2806 197

3-0ctyl acetate 3583 2347

Octyl butyrate 2807 272

Octyl formate 2809 342

Octyl2-furoate 3518

Octyl heptanoate Octyl heptylate 2810 366

Octyl isobutyrate 2808 593

Octyl isovalerate 2814 446

Octyl2-methylbutyrate 3604
 Organic Chemicals Used in Flavorings and Fragrances 487

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-..

Point°C c.2"'
.
Classi-
(I)
c ~ closed cup 'i;j
0c 0 <)
fication ~8 unless <C
·o
European
(I)
'i;j
~
..c g.~
,tC)
"'
(I)
.~
Boiling Point oc Melting 0 =-open (I)
c..
C.F.R. Countries ~ til (atmmHg) Point°C cup
""'
Cl)

NI In s s 174 56

NI SLS s s 62 (11 mm)

Art

172.515 NI In s s 84-85 (25 mm) 61

NI In s 82-83 (10mm) 82

NI In s 90-95
(15mm)

Art In In 73-76 (10mm)

NI 75-79 (20 mm) 54

NI In MIS 63 (10mm) 62

NI In MIS MIS 37-38 63

(1.9-2.3mm)

NI In MIS 81 (20-21 mm)

NI 88-89 (8mm)

172.515 NI In s 190 +67

NI SLS MIS 80-81 (3.5 mm)

Art 112-113 (8 mm)

172.515 NI In s s s 211 -38.5 86 FCC

172.515 NI 191 63

172.515 NI VSI s s 224 -56 103

172.515 Art In s s s 87-89 (20mm) 77 FCC

EOA

NI In MIS 126-127 (1 mm) >110

172.515 Art In s s 290-291 -21.5

172.515 NI In s s 237

172.515 NI In s s 249-251 >110

NI MIS MIS 125-126

(1.4mm)
488 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Octyl octanoate Octyl caprylate 2811 395

Octyl phenylacetate Octyl a-toluate 2812 230

Octyl propionate 2813 407

Oleic acid 2815 13

3-0xobutanal dimethyl acetal 3381

2-0xobutyric acid 3723

Palmitic acid Hexadecanoic acid 2832 14

Paraffin wax 3216

ro-Pentadecalactone "Thibetolide" 2840 181

2,4-Pentadienal 3217

2,3-Pentanedione Acetyl propionyl 2841 2039

2-Pentanol see-n-amyl alcohol 3316

2-Pentanone Methyl propyl ketone 2842 754

2-Pentenal 3218

4-Pentenoic acid Allyl acetic acid 2843 2004

1-Penten-3-ol Ethyl vinyl carbinol 3584

2-Penten-1-ol 665

1-Penten-3-one Ethyl vinyl ketone 3382

3-Penten-2-one Methyl propenyl ketone 3417 666

2-Penthyl-1-buten-3-one 3725

2-Pentylfuran 3317

Pentyl-2-furyl ketone 3418

2-Pentodecanone 3724

2-Pentylpyridine 3383

Perillaldehyde 3557 4154

 Organic Chemicals Used in Flavorings and Fragrances 489

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
PointoC c
Classi- 0.) ..:!.l .!2
c closed cup
fication .... 0
c >.-o
0.)
6 unless
(;;
u
u:::
European
0.) co o.u "0
0.)
Boiling Point oc 0 =open
·o
(;; ..c: 0 Melting
w
>,
>< 0.)

C.F.R. Countries ~ ~6 t.L: (at mmHg) Point oc cup

0.
(/)

172.515 NI In s s 306-307 -18

172.515 Art In s s 315

172.515 NI In s s s 225-226 -42

172.860 NI VSI s s 340 13 +100 FCC

Art

NI s s 80-82 31-32
(16mm)

172.860 NI V Sl s s 271 (100mm) 62 >110 FCC

172.615 >93

172.515 NI In s VSI 137 (2mm) 34-38 >110

NI s s 30 (10mm)

172.515 NI VSI s s s 110-112 -52 17 FCC

NI vs s s MIS 118-119 40

172.515 NI SI s MIS 100-110 -78 7 FCC

NI 124 22

172.515 NI Sl s s 83-84 (12mm) -225 90

172.515 NI Sl s 114 25

NI

NI In s 68-70 (200mm) -7 <4

NI 122 21

Art In s 81 (33mm)

NI 64-66 (23 mm) 45.5

Art 65-67 (0.5 mm) 107

NI In s
NI 102-107

172.515 NI 104-105 (10mm) 95.5

490 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Perillyl acetate 3561

a-Phellandrene p-Mentha-1 ,5-diene 2856 2177

Phenethyl acetate 2-Phenylethyl acetate 2857 221

Phenethyl alcohol PEA 2858 68

Phenethylamine 1-Amino-2-phenylethane 3220 708

Phenethyl anthranilate 2859 258

Phenethyl benzoate 2860 667

Phenethyl butyrate 2861 506

Phenethyl cinnamate 2863 336

Phenethyl formate 2864 350

Phenethyl2-furoate 2865 362

Phenethyl hexanoate Phenylethyl caproate 3221

Phenethyl isobutyrate 2862 302

Phenethyl isovalerate 2871 461

Phenethyl2-methylbutyrate Phenethyl2-methylbutyrate 3632

Phenethyl octanoate Phenylethyl caprylate 3222

Phenethyl phenylacetate 2866 234

Phenethyl propionate 2867 418

Phenethyl salicylate 2868 437

Phenethyl senecioate Phenethyl-3-methyl-2-butenoate 2869 246

Phenethyl tiglate 2870 2186

Phenol 3223

Phenoxyacetic acid Phenoxyethanoic acid 2872 2005

 Organic Chemicals Used in Flavorings and Fragrances 491

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
Classi-
0.) .!!l .!2
c closed cup
fication ....0.) 0c ,.!:!_
;..,o
6 unless
'c;j
u
<C
-o
European 'c;j "'
..c g.~ 0.)
>< Boiling Point oc Melting 0 =open
"<j
0.)

C.F.R. Countries :::: CiJ ~c:;l ij; (at mmHg) Pointoc cup
c..
en

172.515 NI In s s +67

172.515 NI In s MIS (dl) 175-176 47 FCC

172.515 NI In s s s 238-239 101.5 FCC

EOA

172.515 NI Sl s s s 219-221 -27 102 FCC

(740mm) EOA

NI s s 199-200 90

172.515 Art In s 226 39-44 >110

172.515 NI In s s +300 +100

172.515 NI VSI s s 260 >110

172.515 NI In s s +300 58 +100

(HOT)

172.515 NI s s s 226 +100

Art In s >100

NI VSI s s 263 >110

172.515 NI In s s 250 108 FCC

172.515 NI In s s 268 >110 FCC

172.515 NI In s s 206 >110

NI In s s 295-296 >110

172.515 NI In s s 325 28 +100 FCC

EOA

172.515 NI In s s s 245 +100

172.515 NI In s s 370 44 +100 FCC

172.515 NI In s s +100

172.515 NI In s s 139-140 (7mm) >110

NI s s s s 182 38-42 79

172.515 Art VSI s s s 285 99-103 +100

(decomposes)
492 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Phenoxyethyl isobutyrate 2873 2089

Phenylacetaldehyde Hyacynthin 2874 116

Phenylacetaldehyde 2,3-butylene glycol 2875 669

acetal

Phenylacetaldehyde diisobutyl acetal 3384 595

Phenylacetaldehyde dimethyl acetal 2876

Phenylacetaldehyde glyceryl acetal 2877 41

Phenylacetic acid a-toluic acid 2878 672

1-Phenylalanine 3585

d-Phenylalanine 3726

4-Phenyl-2-butanol Phenylethyl methyl carbinol 2879 85

2-Phenyl-2-butenal 3224 670

4-Phenyl-3-buten-2-ol 2880 2032

4-Phenyl-3-buten-2-one Cinnamyl methyl ketone 2881 158

4-Phenyl2-butyl acetate 2882 671

2-Phenyl-3-carbethoxy furan 3468 2309

Phenyl disulfide 3225

2-Phenylethyl valerate 673

2-Phenyl-3(2-furyl) prop-2-enal 3586

1-Phenyl-3-methyl-3-pentanol 2883 86

1-Phenyl-3(or 5)-propylpyrazole 3727 2277

5-Phenylpentanol Phenylamyl alcohol 3618 674

3-Phenyl-4-pentenal 3318
 Organic Chemicals Used in Flavorings and Fragrances 493

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c"'
... .52
Classi-
fication .... 0 ...!:=
;;,-o 6"' closed cup
unless "'
(,)

... !:=
o..u
"'... Boiling Point oc
<.;:::
·u...
"'
0:
European ..c: 0 » Melting 0 =open
C.F.R. Countries ~ ~ ~a ~ (at mmHg) Point°C cup
0..
V'J

172.515 Art In s s 265 +100 FCC

172.515 NI V Sl s s s 195 33-34 87 FCC

EOA

172.515 Art In s s 118 (10mm)

Art VSI s s 240 +100

172.515 NI In s s 221 88 FCC

EOA

172.515 Art In s s 95

172.515 NI Sl(cold) s s 265 76-78 +100 FCC

S(hot) EOA

172.230 Nl Sl In 270-275 +100

(decomposes)

NI s SLS In 271-273 >93

172.515 Art In s 123-124 (15 mm) +100

NI 177 (15mm) >93

172.515 Art In s s s 131 (12mm) 34 >93

172.515 NI In s s 260-262 41-42 68

172.515 Art In s s 123-124 (13 mm)

Art In MIS 148-154 (6mm)

Art In s 310 58-62 +100

(decomposes)

Art In 85-87 56-57

(0.001 mm)

172.515 Art V Sl s 254 >93

Art 155 (20mm)

Art In 155 (22mm) >110

Art
494 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2-Phenyl-4-pentenal 3519

1-Phenyl-1 ,2-propanedione Methyl phenyl glyoxal 3226 2275

1-Phenyl-1-propanol 2884 82

3-Phenyl-1-propanol Hydrocinnamyl alcohol 2885 80

2-Phenyl propionaldehyde Hydrotropic aldehyde 2886 126

3-Phenyl propionaldehyde Phenylpropyl aldehyde 2887 2013

2-Phenyl propionaldehyde dimethyl acetal 2888 2017

3-Phenylpropionic acid Hydrocinnamic acid 2889 32

3-Phenyl-propyl acetate 2890 222

2-Phenyl-propyl butyrate 2891 285

3-Phenylpropyl cinnamate 2894 338

3-Phenylpropyl formate 2895 351

3-Phenylpropyl hexanoate 2896 321

2-Phenylpropyl isobutyrate Hydrotropyl isobutyrate 2892 2087

3-Phenylpropyl isobutyrate 2893 303

3-Phenylpropyl isovalerate 2899 462

3-Phenylpropyl propionate 2897 419

2-(3-Phenylpropyl)pyridine 3751

2-(3-Phenylpropyl)-tetrahydrofuran 2898 489

Phosphoric acid 2900

a-Pinene 2902 2113

~-Pinene 2903 2114

 Organic Chemicals Used in Flavorings and Fragrances 495

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility
OJ .!a
Flash
Point°C
--
="'
.2
Classi- c: closed cup
... 0 0 'iu<i
>--s
OJ
fication c: unless
European
OJ
'i<i "'
..c:
Q.u
0
"0
>. OJ
>< Boiling Point oc Melting 0 =open ·oOJ
~

C.F.R. Countries ~ ~ ~6 ~ (atmmHg) Point°C cup

Q.,
<n

Art In MIS 95 (3mm)

NI s s s 222 84
172.515 NI In s s 220 >93
172.515 NI VSI s s s 233-235 -18 109 FCC
(740mm)

172.515 Art In s s 92-94 (12mm) 80 FCC

EOA
172.515 NI In s s s 222 95 FCC
EOA
172.515 Art In s s 240-241 83 FCC
172.515 NI Sl s s s 280 47-50 >110
172.515 NI In s s s 244-245 +100 FCC
172.515 Art In s s >110
172.515 NI In Sl s +300 +100
(decomposes)

172.515 Art In s s 280 +100

172.515 Art In s s 292 +100
172.515 Art In s s >110
172.515 NI In s s s 252 >110
172.515 Art VSI s s 280 +100
172.515 Art VSI s s 265 +100

Art In s s 142-143
(1 mm)

172.515 Art VSI s s 105-107 (1 mm)

182.1073 NI

172.515 NI In s VSI s 156-160 -62.5 35

172.515 NI In s VSI s 164-169 31

496 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2(10)-Pinen-3-ol Pinocarveol 3587

Pinocarveol 3587

Piperidine Hexahydropyridine 2908 675

Piperine 1-Piperoylpiperidine 2909 492

Piperitenone 3560

Piperitenone oxide

d-Piperitone p-Menth-1-en-3-one 2910 2052

Piperonal Heliotropine 2911 104

Piperonyl acetate Heliotropyl acetate 2912 2068

Piperonyl isobutyrate 2913 305

Potassium 2-1 ( 1-ethoxy) 3752

ethoxypropanoate

Potassium sorbate Potassium 2,4-hexadienoate 2921

1-Proline 2-Pyrrolidine carboxylic acid 3319 4211

1,2-Propanedithiol 3520

1,3-Propanedithiol 3588

Propanethiol 3521

4-Propenyl-2,6-dimethoxyphenol 3728

Propenylguaethol 2922 170

Propenyl propyl disulfide 3227 4026

Propionaldehyde Prop anal 2923 90

Propionic acid Methyl acetic acid 2924 3

2-Propionylpyrrole Ethyl2-pyrrolyl ketone 3614

2-Propionylthiazole 1-(2-Thiazolyl)-1-propanone 3611

 Organic Chemicals Used in Flavorings and Fragrances 497

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c.:2"'
o.l $.l
Classi- c: closed cup 'iiiu
fication ... 0c: o.l
>.o 6 unless \1:
c..u "0 ·u
European ~ "'
..c: o.l
Boiling Point oc Melting 0 =open
p.';o
0 >,
l.i:"'
o.l
c..
C.F.R. Countries ~ ~ (at mmHg) Point oc cup (/)

172.515 NI In s s cis 217, trans 210 51 75

5

172.515 NI s s s 210 4-5

172.515 NI s s s 106 -13 4.5

172.515 NI V Sl s s 128-129

172.515 NI In s s 233

172.515 NI 25.5-26

172.515 NI In s s 235-237

182.60 NI In s Sl s 264 35-37 >110 FCC

EOA

172.515 NI VSI s s 150-151 (10 mm) >110

172.515 Art V Sl s s 91-92 >110

(0.005mm)

Art s In

182.3640 NI s s +100 FCC

172.320 NI vs Sl In 220-222 >93 FCC

(decomposes)

Art In MIS 152 35

NI In MIS 169 -79 60

172.515 NI V Sl s s 67-68 -113 -20

NI In s 135
(0.13mm)

172.515 Art Sl s s s 85-86 +100 FCC

(sublimes)

NI 78-80 (13 mm)

172.515 NI s s 48-49 -81 -27 FCC

184.1081 NI s s 141 -24 to -23 52 FCC

NI SLS In 43-45

NI
498 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Propiophenone 3469 599

Propyl acetate 2925 192

Propyl alcohol 1-Propanol 2928 50

p-Propyl anisole Dihydroanethole 2930 2026

Propyl benzoate 2931 677

Propyl butyrate 2934 266

Propyl cinnamate 2938 324

Propy12,4-decadienoate 3648

4-Propyl-2,6-dimethoxyphenol 3729

Propyl disulfide Dipropyl disulfide 3228 540

Propylene glycol 1,2-Dihydroxypropane 2940 4212

Propylene glycol alginate Hydroxypropyl alginate 2941

Propylene glycol dibenzoate 3419

Propylene glycol monostearate (mixed mono and diesters) 2942

Propyl formate 2943 340

Propyl2-furanacrylate 2945 2090

Propyl2-furoate 2946 359

Propyl gallate 2947

Propyl heptanoate Propyl heptylate 2948 367

Propyl hexanoate Propyl caproate 2949 311

Propyl p-hydroxy benzoate Propylparaben 2951 678

3-Propylidenephthalide 2952 494

Propyl isobutyrate 2936 289

Propyl isovalerate 2960 443

Propyl mercaptan 1-Propanethiol 3521

 Organic Chemicals Used in Flavorings and Fragrances 499

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c.s:"'
Classi- "' ..:!l closed cup
"'o..u 6
1':: ~
01':: u
fication .... >,C) unless <.t:
"0 ·u
2:lOl Boiling Point oc
tE"'
Ol
European Melting 0"" open
~
..0
~
0
~a
;;.,
(at mmHg) Point oc cup
"'0..
C.F.R. Countries r.rJ

NI In s 218 18 88

172.515 NI s s s s 102 -95 13

172.515 NI s s s MIS 97.2 -127 15

172.515 Art SLS s s 212-213 85 EOA

172.515 NI In s s 230 -51 to- 52 86

172.515 NI VSl s s 142-143 -97 39

172.515 NI In s s 283-284 13 +100

NI

NI In s 115
(0.38mm)

172.515 NI VSl s s 194 33

184.1666 NI s s In 187.3 -60 107 FCC

172.515 s +100 FCC

Art 200 (2mm) +100

172.856 Art In s s +100 FCC

172.515 NI V Sl s s MIS 81.3 -92.9 4

172.515 Art In s s 236

Art In s s 211

184.1660 V Sl s s 150 FCC

172.515 NI In s s s 206-208 -64 77

172.515 NI In s s s 187 -69 51.5

172.515 NI V Sl s 95-98 >93 FCC

172.515 NI VSl s 273 >93

172.515 Nl In s s s 135

172.515 NI In s s s 156-157

172.515 Nl Sl s s 67-68 -111 -20

500 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Propy12-methyl-3-furyl disulfide 2-Methyl-3-furyl propyl disulfide 3607

a-Propylphenethyl alcohol Benzyl butyl alcohol 2953 83

o-Propylphenol 3522

p- Propylphenol 4-Propylphenol 3649

Propyl phenylacetate n-Propyl a-toluate 2955 229

Propyl propionate 2958 403

Propyl thioacetate 3385

Propyl valerianate 679

Pule gone p-Menth-4(8)-en-3-one 2963 2050

Pseudocyclocitral 2133

Pyrazine ethanethiol 2-Pyrazinyl ethyl mercaptan 3230 2285

Pyrazinemethylthiol 3299

Pyrazinylmethyl sulfide Methylthio pyrazine 3231 2288

Pyridine 2966 604

2-Pyridinemethanethiol 3232 2279

Pyroligneous acid 2967 4033

Pyroligneous acid extract "Liquid smoke" 2968 4032

Pyrrole Imidole 3386 2318

Pyrrolidine 3523

Pyruvaldehyde Pyruvic aldehyde 2969 105

Pyruvic acid 2970 19

Quinine bisulfate 2975 716

Quinine hydrochloride 2976 715

Quinine sulfate 2977 717

 Organic Chemicals Used in Flavorings and Fragrances 501

TABLE 10-l. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c.!:!"'
0) :a closed cup
"'
Classi- c
0c 0) 6 u
fication
'"' >-o
o.u "0
unless <.:
·o0)
"' Boiling Point oc
0)
0 =open
"'
European ..c 0 >,
0)
>< Melting 0.
C.F.R. Countries ~ ~ ~6 li: (atmmHg) Point°C cup ell

Art In s 75.5-79
(1.4mm)

172.515 Art VSL s s 247 >93

Art Sl s s 224-226 93

172.515 NI In s 232 -22 111

172.515 Art V Sl s s 253

172.515 NI Sl s s MIS 122-124 -76 20

NI s 137-139

NI In s
172.515 NI In s s 220-222 82

Art 79

Art SSL 105-110 (20mm) >110

Art 44-45 (0.07 mm)

Art In 112 (10mm)

172.515 NI s s s s 115.5 -42 20

Art In MIS 102 (20mm) >110

NI +67

172.515 NI MIS In MIS In

NI V Sl s s 130-131 -23 33
(decomposes)

NI MIS MIS 87 -63 to -60 2

172.515 NI s 72

172.515 NI s s 165 11-12 84

Nat s s s 160 +100

172.575 Nat s s s 158-160 +100 FCC

172.575 Nat s s s 205 +100 FCC

(hot) MIS
502 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Quinoline Chinoline 3470

Rhamnose 3730

Resorcinol 1,3-Benzenediol 3589

Rhodinol (mixed, principally 1-citron-elloi) 2980 76

Rhodinyl acetate (mixed, principally 1-citronellyl 2981 223

acetate)

Rhodinyl butyrate Citronellyl butyrate 2982 284

Rhodinyl formate Citronellyl formate 2984 346

Rhodinyl isobutyrate Citronellyl isobutyrate 2983 297

Rhodinyl isovalerate Citronellyl isovalerate 2987 460

Rhodinyl phenylacetate Citronellyl phenylacetate 2985 2163

Rhodinyl propionate Citronellyl propionate 2986 422

Rum Ether Ethyl oxyhydrate 2996

Salicylaldehyde 2-Hydroxybenzaldehyde 3004 605

Santalol (a and~) "Argeol" 3006 74

Santalyl acetate (mixed isomers) 3007 224

Sodium hexametaphosphate 3027

Santalyl phenylacetate 3008 239

Skatole 3-Methyl indole 3019 493

Sodium acetate 3024 4221

Sodium benzoate 3025

Sodium citrate 3026 4222

Sorbitan monostearate 3028

d-Sorbitol 3029 81
 Organic Chemicals Used in Flavorings and Fragrances 503

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

~
Point°C c
.!2
Classi- "'c §"'
..
closed cup Oj
fication 0c "'
>-o 'U unless u
<:::
·c:;
Boiling Point oc
Q..U

lZ"'
~ 0:
European ..c 0 » Melting 0 =open
C.F.R. Countries
0:
~ ~ ~5 (atmmHg) Point°C cup "'
Q..
ell

NI Sl vs 113-114 (17mm) -16 to -15 101

NI s s s 276 111 171 FCC

172.515 NI In s s s +100 EOA

172.515 Art In s In s 237 +100 FCC

EOA

172.515 NI In s In s 137 (13mm) +100 FCC

172.515 Nl In s In s 220 +100

172.515 Nl In s s 260 +100

172.515 Nl VSl s s 270 +100

172.515 Art In s s 340 +100

172.515 NI VSl s s 255 +100

172.515 Nl 65-87 (rectified <4

material)

172.515 NI Sl s s MIS 196 1-2 76

172.515 NI In s s s a, 302; ~' 309 +100 FCC

EOA

172.515 Art In s s s 20.8 (3mm) +100 FCC

173.310 NI

172.515 Art In Sl s 342 +100

172.515 Nl s s s s 265-266 95-97 +100

(boiling)

184.1721 NI s s >300 +100 FCC

184.1733 NI s s +100 FCC

182.1751 NI s In +100 FCC

172.515 Disp. s SSL 54-57 >110 FCC

(hot)

184.1835 s Sl 93-97 FCC

504 Source Book of Flavors

TABLE 10-l Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Stearic acid Octadecanoic acid 3035 15

Styrax extract 3037 265

Styrene 3233

Sucrose octaacetate 3038

Sulfur dioxide 3039

Tannic acid 3042 746

Tartaric acid 1( +)-Tartaric acid 3044 18

a-Terpinene 1,3-p-Menthadiene 3558

y-Terpinene 1 ,4-p- Menthadiene 3559

a-Terpineol p-Menth-1-en-8-ol 3045 62

~-Terpineol p-Menth-8-en-1-ol 3564

Terpinolene p-Menth-1 ,4(8)-diene 3046 2115

Terpinyl acetate p-Menth-1-en-8-yl acetate 3047 205

Terpinyl anthranilate 3048 259

Terpinyl butyrate 3049 278

Terpinyl cinnamate 3051 330

Terpinyl formate 3052 348

Terpinyl isobutyrate 3050 300

Terpinyl isovalerate 3054 456

Terpinyl propionate 3053 423

1\-Tetradecalactone 3590 2196

4,5,6, 7-Tetrahydro-3, Menthofuran 3235 2265

6-dimethylbenzofuran

Tetrahydrofurfuryl acetate 3055 2069

 Organic Chemicals Used in Flavorings and Fragrances 505

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C c"'
.2
Classi-
Q)
c ~ closed cup ~
fication ... 0c Q)
>.o 6 unless
u
<::::

*
c..u "0 ·;::;
European "'
..c 0» Q)
Boiling Point oc Melting 0 =open Q)
c..
C.F.R. Countries ~ ~ ~6 tZ (atmmHg) Point°C cup rJJ

184.1090 NI In s s 363 69-70 +100 FCC

172.510 N

172.515 NI Sl s s 145-146 -33 31

172.515 NI Sl s 260 84 >93

182.3862 NI

182.20 Nat vs s 210 +100 FCC

184.1099 NI s s 170-174 210 FCC

172.515 NI In s s 176 d, 168-170

172.515 NI In s s 182 52

172.515 NI VSI s s s 217-218 30 91 FCC

EOA

172.515 NI VSI s s 210 32

172.515 NI In s s s 183-185 64

172.515 NI VSI s s s 220 100 FCC

EOA

172.515 Art In s s 365 +100

172.515 NI In s s 244 +100

172.515 Art In s MIS 360 +100

172.515 NI VSI s s 225 +67

172.515 NI VSI s s 242 +100

172.515 Art In s 248 +100

172.515 NI In s s 240 +100 FCC

EOA

NI In s s 155-154
(O.Smm)

NI In s 80-82 (13 mm) 75.5

172.515 Art s s MIS 194-196 84

506 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Tetrahydrofurfuryl alcohol THFA 3056 2029

Tetrahydrofurfuryl butyrate 3057 2081

Tetrahydrofurfuryl cinnamate 3320

Tetrahydrofurfuryl propionate 3058 2096

Tetrahydro pseudoionone 6,10-Dimethyl-9-undecen-2-one 3059 2053

Tetrahydrolinalool 3,7-Dimethyloctan-3-ol 3060 77

Tetrahydro-4-methyl-2-(2-methylpropen- Rose oxide 3236 2269

1-yl) pyran

5,5,7,8-Tetrahydroquinoxali ne Cyclohexanepyrazine 3321 721

Tetramethylethylcyclohe xenone (mixed isomers) 3061 168

2,3,5,6-Tetramethyl pyrazine 3237 734

1 ,5 ,5 ,9-Tetramethyl-13-oxatricyclo- Ambrox 3471

(8,3,0,0( 4,9)) tridecane

Thaumatin 3732

Theobromine 3, 7-Dimethylxanthine 3591

Thiamine hydrochloride 3322

Thiazole 3615

2-Thienyl disulfide 2,2'-Dithiodithiophene 3323 2333

2-Thienyl mercaptan 2-Thienylthiol 3062 478

2,2' -(Thiodimethylene )-difuran Difurfuryl sulfide 3238

Thiogeraniol 3472

4-Thujanol 3239

Thymol 3-p-Cymenol 3066 174

Tolualdehyde glyceryl acetal (mixedo, m andp) 3067 46

Tolualdehyde (mixed, o, m andp) 3068 115

 Organic Chemicals Used in Flavorings and Fragrances 507

TABLE 10·1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,......

Point°C C'"'
.9
Classi-
. 5"'
II)
c closed cup '(;
0 II)
u
fication c >-o "0 unless tC
·;:;
B
£"' Boiling Point oc
P.u
European 0 ..... II)
Melting 0 ==open
:s:"' >< II)

C.F.R. Countries ~ ~G ii: (atmmHg) Point°C cup en

P.

172.515 NI s s MIS 178 -80 84

172.515 Art In s MIS 225-227 99

Art In s s +300

172.515 Art SI s MIS 207 (3mm)

172.515 Art VSI s s 234 (14mm) +100

172.515 Art VSI s s s 87-88 (10mm) 84

NI SSL s 188 68

NI 85 (3mm) 29-30 90.5

172.515 Art VSI s s 113-115 (6mm)

NI In s 190 84-86 78

NI In s 28

N s SLS

NI s 290-295 357
(sublimes)

184.1875 NI s 248

NI SLS 115-118 22

NI 115 55-60

172.515 Art VSI s s 166

NI 135-143 (14mm) 31-32 793

Art 58 (0.35mm) trans 60-61;

cis
36.5-37.2

NI

172.515 NI VSI s s s 233 48-51 102

172.515 Art VSI s s 292 >93

(decamp.)

172.515 NI Sl s s 199-204 -6 90
508 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

p-Toluacetaldehyde 3071 130

o-Tolyl acetate Acetyl o-cresol 3072 2078

p-Tolyl acetate Acetyl p-cresol 3073 226

4-(p-Tolyl)-2-butanone p-Methylbenzyl acetone 3074 160

p-Tolyl isobutyrate p-Cresol isobutyrate 3075 304

o- Tolyl isobutyrate 3753 681

p-Tolyllaurate p-Cresyl dodecanoate 3076 378

p-Tolyl3-methylbutyrate p-Cresyl isovalerate 3387

p-Tolyl octanoate 3733

p-Tolyl phenylacetate p- Tolyl a-toluate 3077 236

o-Tolylsalicylate 3734

2-(p-Tolyl)-propionaldehyde p-Methylhydrotropic aldehyde 3078 131

Tributyl acetylcitrate 3080

Tricalcium phosphate 3081

2-trans-4-cis-7 -cis-Tridecadienal 3638 685

Tridecan-2-one 3388

Tridecen-2-al 3082 2011

Triethyl citrate 3083

Trimethylamine 3241

p-a,a-Trimethylbenzyl alcohol P-Cymen-8-ol 3242 530

4-(2,6,6-Trimethylcyclohexa-1 ,3-dienyl) ~- Damascenone 3420

but-2-en-4-one

2,6,-Trimethylcyclohexa-1 ,3-dienyl Safranal 3389

methanal

2,6,6-Trimethylcyclohexanone 3473 686

 Organic Chemicals Used in Flavorings and Fragrances 509

TABLE 10·1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ..-..

~
Point°C c
.52
6"'
II)
Classi- c closed cup t;j
fication .... 0
c ..!:!-
>.o unless ...
<!:
"0 ·c:;
"' Boiling Point oc
C..<.>
~
a: a
European ..c 0 >. II)
I>< Melting 0 =open II)

~ i.i: c..
C.F.R. Countries ~ (atmmHg) Point°C cup rn

172.515 Nl In 210 70

172.515 Art Sl s s s 208

(hot)

172.515 NI s s s 208-209 95 FCC

172.515 Art VSl s s

172.515 Art In s s 237 +100 FCC

Art

172.515 Art In s s +100

Art In s 103-110 +100

(2-3mm)

Art +100

172.515 Art In s Poor 310 74-75 +100 EOA

Art In s 35 >93

172.515 Nl In s 222-224 89

172.515 Art In s MIS 172-174 89

(+300 1mm)

182.1217 NI

NI In s 138 (0.3mm)

NI

172.515 Nl VSl s 134 (10mm) 28-31 >110

182.1911 NI SLS s s 294 >110

173.20 NI s s 3.8 -124 3

NI >93

NI 56-58 (0.1 mm) >93

NI In s s 95-100 (11 mm)

NI In s
510 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

2,6,6-Trimethyl-1-cyclohexen-1- 3474
acetaldehyde

2,6,6-Trimethyl-1 or 2-cyclohexen-1- a & ~-Cyclocitral (50/50) 3639 2133

carboxaldehyde

2,6,6-Trimethylcyclohex-2-ene-1 ,4-dione 3421

4-(2,6,6-Trimethylcyclohex-1-enyl) ~-Damascone 3243

but-2-en-4-one

2,2,3-Trimethylcyclopent-3-en-1-yl Campholenic aldehyde 3592

acetaldehyde

3,5 ,5-Trimethylhexanal 3524 702

3 ,5,5-Trimethyl-1-hexanol Trimethyl hexyl alcohol 3324 702

1,3,3-Trimethyl-2-norbornyl acetate Fenchyl acerate 3390

2,2,4-Trimethyl-1 ,3-oxacyclopentane 3441

2,4,5-Trimethyl-Ll,3-oxazoline 3525 2319

2 ,6, 10-Trimethyl-2,6, 10-pentadecatrien- Farnesyl acetone 3442

14-one

2,3,5-Trimethyl pyrazine 3244 735

2,4,5-Trimethyl thiazole 3325

2,2,6-Trimethyl-6-vinyltetrahydropyran 3735

1,2,3-Tris[ (1 'ethoxy )-ethoxy] propane 3593

Trithioacetone 3475 2334

Tyrosine 3736

2,4-Undecadienal 3422

2,5-Undecadienal 687

2,3-Undecadione 3090 155

y-Undecalactone Aldehyde C-14 3091 179

Peach aldehyde
 Organic Chemicals Used in Flavorings and Fragrances 511

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point oc c"'
Classi-
Q)
c ~
closed cup
.:::
<;;
fication ....Q) 0
c
..!:!-
>.o
0 unless
<..>
<J:
-o ·c::;
European <;; -5"" g.~ Q)
>< Boiling Point oc Melting 0 =open Q)

Point oc
0..
C.F.R. Countries ~ (.l.l ~c.:; ti: (at mmHg) cup ell

Art In MIS s 50 (0.4mm) 73

NI In 80-95 (70mm)

NI

NI trans 55
(0.001 mm)
cis 52
(0.001 mm)

NI In s 77 (10mm)

NI SSL s 167 45

NI VSl s s 142 (150mm) 76

NI In s s 220

NI 98-99

NI 147-148 <4
(0.5mm)

NI s s s 147-148
(O.Smm)

NI 171-172 54

NI 166-167 56
(717mm)

NI

Art In s s 117 (l.Omm)

NI In MIS 105-107 (10 mm) 24 97

172.320 N SLS In 342-344

NI In s s s 126 (8mm) 107

NI

172.515 Art VSl s s 109-111 (10mm)

172.515 NI In s s s 164-166 (13 mm) >110 FCC

EOA
512 Source Book of Flavors

TABLE 10-1 Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Undecanal 3092 121

Undecanoic acid 3245 696

2-Undecailol 3246

2-Undecanone Methyl nonyl ketone 3093 150

2-Undecenal (mixed isomers) 3423

9-U ndecenal 3094 123

10-Undecenal 3095 122

10-Undecenoic acid 3247 689

10-Undecen-1-ol

10-Undecen-1-yl acetate Undecylenic acetate 3096 2062

Undecyl alcohol Alcohol C-11 3097 751

Valencene 3443

Valeraldehyde 3098 93

Valerie acid n-Pentanoic acid 3101 7

y-Valerolactone 3103 753

dl-Valine a-Aminoisovaleric acid 3444

Vanillin 4-H ydroxy-3-methoxybenzaldehyde 3107 107

Vanillin acetate Acetyl vanillin 3108 225

Vanillin isobutyrate 3754

Vanillyl alcohol 3737 690

Vanillylidene acetone 3738 691

Veratraldehyde Methyl vanillin 3109 106

Verbenol 3594
 Organic Chemicals Used in Flavorings and Fragrances 513

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ,-..

~
Point•c c
.2
"'
.
<I)
Classi- closed cup
fication 0
c
c
<I)
>.o 6 unless
~
<J
<C
-o ·c::;
-5"'
~ P.,<J
European 0 >. <I)
Boiling Point •c Melting 0 =open
"'
<I)

C.F.R. Countries ~ ~ ~6 ~ (atmmHg) Point•c cup

Po.
Cl)

172.515 NI In s s 118-120 (20mm) -4 96

NI In vs s 164.5 (15 mm) 28-29 >93

NI In s s 228-229

172.515 NI In s s s 228-230 13-15 88

NI In s s 229 90

172.515 Art In s s 229 79 FCC

EOA

172.515 NI In s s s 103 (3mm) 7 100 FCC

EOA

NI In s s 285 28.5 148

172.515 NI In s s 132-133 (15 mm) 15 93

172.515 Art In s s s 272 >93

172.515 NI In s s s 146 (30mm) 11 >110

NI In MIS s 123 (11mm) >93

172.515 NI VSl s s s 102-103 -91.5 12

172.515 NI Sl s 184-186 34 95(0) FCC

NI s s MIS 205-206 95(0)

NI s In 298 >93
(decomposes)

182.60 NI s s s s 170 (15mm) 81-83 >93 FCC

(sublimes)

172.515 NI Sl s s s 77-79 >93

Art In MIS In 155 (5.5mm)

NI Sl S s 112-115 >93

NI Sl S 125-130

172.515 NI VSl s s 281 43-46 >110

172.515 NI 90-95 (10 mm) cis 72

trans 22.5
514 Source Book of Flavors

TABLE 10-l Continued

Council
of
FEMA Europe
Chemical Name Other Names No. No.

Vetiveryl acetate Vetiver acetate 2284

o-Vinyl anisole 3248

4-Vinyl phenol 3739

2,5-Xylenol 2,5-Dimethylphenol 3595 537

3,4-Xylenol 3,4-Dimethylphenol 3596

2,6-Xylenol 2,6-Dimethylphenol 3249

d-Xylose 2,3,4,5-Tetrahydroxy pentanal 3606

Zingerone 4-( 4-Hydroxy-3-methoxyphenyl)-2- 3124 139

butanone

Synonym Refer to Chemical Listed in Main Tabular Body

Acetaldehyde benzyl /3-methoxyethyl acetal Benzyl methoxy acetal
Acetaldehyde diethyl acetal Acetal
Acetaldehyde dimethyl acetal 1, 1-Dimethoxyethane
AcetalR Acetaldehyde phen ethyl propyl acetal
Acetic aldehyde Acetaldehyde
Acetic ether Ethyl acetate
2' -Acetonaphthone Methyl/3-naphthylketo ne
Acetone propylene glycol acetal 2,2,4-Trimethyl-1,3,-oxycyclopentane
2-Acetoxy-3-butanone Acetyl methyl carbinyl acetate
1-Acetoxy-2-methoxybenzene Guaiacyl acetate
4-Acetoxy-3-methoxy-1-(1-propen-1-yi) benzene Isoeugenylacetate
3-Acetoxyoctene 1-0cten-3-yl acetate
Acetoyl butyrate Butan-3-one-2-yl butanoate
Acetylacetaldehyde dimethyl acetal 3-0xybutanal, dimethyl acetal
p-Acetyl anisole (4-acetyl anisole) Acetanisole
Acetylbenzene Acetophenone
Acetyl benzoyl 1-Phenyl-1,2-propanedione
Acetyl butyryl 2,3-Hexanedione
Acetyl o- (or p-) cresol o- (or p-) Tolyl acetate
p-Acetyl cumene ~-isopropylacetophenone
Acetyl eugenol Eugenyl acetate
Aceto isoeugenol iso-Eugenyl acetate
2-Acetylfuran 2-Fury! methyl ketone
1-Acetyl-4-methyl-2,3-hexanedione 4'-Methylacetophenone
Acetyl methyl carbinol Acetoin
/3-Acetylnaphthalene Methyl/3-naphthylketo ne
3-Acetylpropionic acid Levulinic acid
2-Acetylpyrrole Methyl2-pyrrolyl ketone
p-Acetyltoluene 4'-Methylacetophenone
Acetyl-m-xylene 2,4-Dimethylacetopheno ne
Achilleic acid Aconitic acid
Albacol Propyl alcohol
AlcoholC-7 He_ptyl alcohol
AlcoholC-8 1-0ctanol
AlcoholC-9 Nonyl alcohol
Alcohol C-10 1-Decanol
 Organic Chemicals Used in Flavorings and Fragrances 515

TABLE 10-1. Continued

Legal status Physico-chemical characteristics

Solubility Flash ~

Point°C "'c
'-'
0.)
~
.9
Classi- c closed cup 'c;i
0c ,!l_ 0 u
fication ....0.) >.o -o0.) unless <!:
·c:;
Boiling Point oc
o..u
European 'c;i "'
..c
til
0 >.
~6
><
li:
Melting 0 =-open 0.)
0..
C.F.R. Countries ~ (at mmHg) Point°C cup en

Art In s Sl s +100 EOA

NI In 195-200 29-29.5

NI

NI Sl S s 212 72-76

NI Sl S s 205-225 26-75

NI S (hot) s 203 45-48 +67

NI s In 155-158

172.515 NI VSl s 185.5 (13 mm) 40-41 >93

Synonym Refer to Chemical Listed in Main Tabular Body

Alcohol C-11 Undecylic alcohol
Alcohol C-12 Laury! alcohol
Alcohol C-16 1-Hexadecanol
Aldehyde C-7 Heptanal
Aldehyde C-8 Octanal
Aldehyde C-9 Nonanal
Aldehyde C-1 0 Decanal
Aldehyde C-11, undecylic Undecanal
Aldehyde C-11, undecylenic 9-Undecanal
Aldehyde C-12,lauric Lauric aldehyde
Aldehyde C-12, MNA 2-Methylundecanal
Aldehyde C-14 (so-called) 'Y-Undecalactone
Aldehyde C-14, myristic Myristaldehyde
Aldehyde C-16 (so-called) Ethyl methylphenylglycidate
Allerol Nero!
Allomaleic acid Fumaric acid
Allomalenic acid Fumaric acid
Allyl acetic acid 4-Pentenoic acid
p-Allylanisole Estragole
Allyl caproate Allyl hexanoate
Allyl caprylate Allyl octanoate
4-Allylcatechol-2-methyl ether Eugenol
Allyl cyclocitrylideneacetone Allyl a-ionone
Allyl cyclohexanecaproate Allyl cyclohexanehexanoate
Allyl cyclohexanepentanoate Allyl cyclohexanevalerate
Allyl cyclohexylacetate Allyl cyclohexaneacetate
Allyl4-cyclohexyl butyrate Allyl cyclohexanebutyrate
Allyl5-cyclohexylpentanoate Allyl cyclohexanevalerate
Allyl3-cyclohexylpropionate Allyl cyclohexanepropionate
4-Allyl-1,2-dimethoxybenzene Eugenyl methyl ether
Allyl enanthate Allyl hertanoate
4-Allylguaiacol Eugeno
Allyl heptylate Allyl heptanoate
Allyl-2,4-hexadienoate Allyl sorbate
Allyl isopentanoate Allyl isovalerate
Allyl isovalerianate Allyl isovalerate
516 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

4-Allyl- 2-methoxyphenol Eugenol
Allyl {1-methylacrylate Allyl crotonate
Allyl3-methylbutanoate Allyl isovalerate
Allyl trans -2-methyl-2-butenoate Ally I tigla te
Allyl nonylate Allyl nonanoate
Allyl octylate Allyl octanoate
Allyl pelargonate Allyl nonanoate
Allyl {1-phenylacrylate Allyl cinnamate
Allyl3-phenyl-2-propenoate Allyl cinnamate
Allyl propanoate Allyl propionate
Allyl sulfhydrate Allyl mercaptan
Allylthiol Allyl mercaptan
Allyl a-toluate Allyl phenylacetate
Allyl trisulfide Diallyl trisulfide
Allyl undecylenate Allyl10-undecenoate
4-Allylveratrole Eugenyl methyl ether
Ambrettolide w-6- Hexadecenlactone
1-Aminobutane Butylamine
2-Aminoethylbenzene Phenethylamine
Aminoglutaric acid 1-Glutamic acid
1-Aminoisopentane lsopentylamine
o-Aminomethyl benzoate Methyl anthranilate
1-Amino-2-phenylethane Phenethylamine
Ammonium isovalerianate Ammonium isovalerate
Amyl acetate Isoamyl acetate
see-n-Amyl alcohol 2-pentanol
Amyl alcohol, commercial Fuse) oil, refined
Amyl aldehyde Valeraldehyde
Amyl butanoate Amyl butyrate
Amyl isobutanoate Isoamyl butyrate
-y-Amyl butyrolactone -y-Nonalactone
Amyl caprate (caprinate) Amyl decanoate
Amyl caproate Amyl hexanoate
Amyl caprylate Amyl octanoate
Amyl cinnamal a- Amylcinnamaldehyde
Amyl crotonyl acetate 1-0cten-3-yl acetate
Amyl ethyl carbinol 3-0ctanol
Amyl ethyl ketone 3-0ctanone
Amyl heptylate (heptoate) Amyl heptanoate
Amyl2-hydroxybenzoate Amyl salicylate
4-n-Amyl-4-hydroxybutyric acid lactone 'Y- Nonalactone
5-n-Amyl-5-hydroxypentanoic acid lactone 'Y- Decalactone
iso-Amyl aldehyde 3-Methylbutyraldehyde
iso-Amyl amine lsopentylamine
iso-Amyl isobutyrate 3-Methylbutyl 2-methylpropanoate
iso-Amyl caproate Isoamyl hexanoate
iso-Amyl caprylate Isoamyl octanoate
iso-Amyl dodecanoate Isoamyllaurate
a-iso-Amyl furfurylacetate Isoamyl 2-furanbutyrate
iso-Amyl o-hydroxybenzoate Isoamyl salicylate
iso-Amyl {1-ketobutyrate Isoamyl acetoacetate
Amyl methanoate Amyl formate
iso-Amyl methanoate Isoamyl formate
iso-Amyl3-methylbutanoate Isoamyl isovalerate
iso-Amyl2-methylbutanoate 3-Methylbutyl2-methylbutanoate
Amyl3-methylbutanoate Amyl isovalerate
Amyl methyl carbinol 2-Heptanol
Amyl methyl ketone 2-Heptanone
iso-Amyl2-methylpropanoate 3-Methylbutyl2-methylpropanoate
iso-Amyl2-methylpropanoate Isoamyl isobutyrate
iso-Amyl3-oxobutanoate Isoamyl acetoacetate
iso-Amyl pelargonate Isoamyl nonanoate
a- Amyl-{1-phenylacrolein a- Amylcinnamaldehyde
a-n-Amyl-{1-phenylacrolein dimethyl acetal a-Amylcinnamaldehyde dimethyl acetal
a-n-Amyl-{1-phenylacryl acetate a-Amylcinnamyl acetate
iso-Amyl-{1-phenylacrylate Isoamyl cinnamate
a-n-Amyl-{1-phenylacryl3-methylbutanoate a-Amylcinnamyl isovalerate
2-Amyl-3-phenyl-2-propen-1-ol a-Amylcinnamyl alcohol
iso-Amyl propanoate Isoamyl propionate
iso-Amyl a-toluate Isoamyl phenylacetate
~-n-Amyl-~-valerolactone ~- Decalactone
 Organic Chemicals Used in Flavorings and Fragrances 517

Synonym Refer to Chemical Listed in Main Tabular Body

Amyl vinyl carbinol 1-0cten-3-ol
Amyl vinyl carbinol acetate 1-0cten-3-yl acetate
Amyl vinyl ketone 1-0cten-3-one
p- Anisaldehyde p- Methoxybenzaldehyde
Anise alcohol (anisic alcohol) Anisyl alcohol
Anise camphor Anethole
Anisic aldehyde p- Methoxybenzaldehyde
Anisic ketone 1-(,p-Methoxyphenyi)-2-propanone
Anisylacetone 4-tp- Methoxyphenyi)-2-propanone
Anisyl methanoate Anisyl formate
Anisyl methyl ketone 1-(p-Methoxyphenyi)-2-propanone
Anisyl a-toluate Anisyl phenylacetate
Aubepine,liquid p- Methoxy benzaldehyde
Benihinal 2-Formyl-6,6-dimethylbicyclo (3.1.1) hept-2-ene
Benzalglycerin Benzaldehyde glyceryl acetal
1-Benzazine Quinoline
Benzene carbinol Benzaldehyde
Benzenemethanethiol Benzyl mercaptan
Benzilideneacetone 4-Phenyl-3-buten-2-one
1,2-Benzisothiazolin- 3-one-1,1-dioxide Saccharin
1,2-Benzodihydropyrone Dihydrocoumarin
2,3-Benzopyrrole Indole
1- Benzo-13 -pyrrole Indole
1- Benzoxy-1-( 2-methoxyethoxy) ethane Benzyl methoxyethyl acetal
Benzoyl benzene Benzophenone
Benzylacetone 4-Phenyl-3-buten-2-one
Benzylbutyl alcohol a- Propylphenethyl alcohol
Benzyl2,3-dimethyl-2-butenoate Benzyl 2,3-dimethylcrotonate
2-Benzyl-4,5-dimethyl-1,3-dioxolane Phenylacetaldehyde 2,3-butylene glycol acetal
Benzyl dipropyl ketone 3-Benzyl-4-heptanone
Benzyldithiomethane Methyl benzyl disulfide
a-(Benzyldithio) toluene Benzyl disulfide
Benzyl ether Dibenzyl ether
Benzyl ethyl alcohol 3-Phenyl-1-propanol
Benzyl hydrosulfide Benzyl mercaptan
Benzyl a-hydroxy benzoate Benzyl salicylate
Benzylideneacetic acid Cinnamic acid
3-Benzylidene-2-butanone 3-Methyl-4-phenyl-3-butene-2-one
2-Benzylideneheptanol a-Amylcinnamyl alcohol
2-Benzylidenehexanal a- Butylcinnamaldehyde
2-Benzylideneoctanal a- Hexylcinnamaldehyde
Benzylisoamyl alcohol a-Isobutylphenylethyl alcohol
Benzyl isobutyl ketone 4-Methyl-1-phenyl-2-pentanone
Benzyl isoeugenol Isoeugenylbenzylether
Benzyl isopentanoate Benzyl isovalerate
Benzyl isovalerianate Benzyl isovalerate
Benzyl {3-ketobutyrate Benzyl acetoacetate
Benzyl ketone 1,3-Diphenyl-2-propanone
Benzyl-2-methoxy-4-propenylphenyl ether Isoseufenylbenzylether
Benzyl-3-methylbutanoate Benzy isovalerate
Benzyl-2-methylpropanoate Benzyl isobutyrate
Benzyl methyltiglate Benzyl 2,3-dimethylcrotonate
Benzyl oxide Dibenzyl ether
Benzyl3-oxobutanoate Benzyl acetoacetate
1-Benzyloxy-1-({3-methoxy )ethoxyethane Benzyl methoxyethyl acetal
1-Benzyloxy-2-methoxy-4-propenylbenzene Isoeugenylbenzylether
Benzyl{3-phenylacrylate Benzyl cinnamate
2-Benzyl- 2-propanol a, a- Dimethylphenethyl alcohol
2-Benzyl-2-propyl acetate a, a-Dimethylphenethyl acetate
Benzylpropyl carbinol a-Propylphenethyl alcohol
Benzylthiol Benzyl mercaptan
Benzyl tiglate Benzyl trans-2-methyl-2-butenoate
Benzyl a-toluate Benzyl phenylacetate
Berga mol Linalyl acetate
BHA Butylated hydroxy anisole
BHT Butylated hydroxy toluene
Biacetyl Diacetyl
2-Bornanol Borneol
2-Bornanone d-Camphor
Borneocamphor Borneol
Bornyl alcohol Borneol
518 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

Butanal Butyraldehyde
Butanoic acid,p-methoxybenzyl ester Anisyl butyrate
2,3- Butanolone Acetoin
2- Butanon-3-yl acetate Acetyl methyl carbinyl acetate
Butenyl a-cyclocitrylidenemethyl ketone Allyl a-ionone
sec-Butylacetic acid 3-Methylpentanoic acid
Butyl acetylpropionate Butyllevulinate
3- Butylacrolein trans- 2-Heptenal
Butyl aldehyde Butyraldehyde
Butyl caproate Butyl hexanoate
n- Butyl carbinol Amyl alcohol
isoButyl carbylamine lsopentylamine
Butyl decylenate Butyl 2-decenoate
Butyl dodecenoate (dodecylate) Butyllaurate
n- Butyl ethyl carbinol 3-Heptanol
Butyl ethyl ketone 3-Heftanone
Butyl heptylate Buty heptanoate
4-n-Butyl-4-hydroxybutyric acid lactone 'Y-Octalactone
4-Butyl-4-hydroxyoctanoic acid lactone 4,4-Dibutyl-'Y·butyrolactone
5-n-Butyl-5-hydroxypentanoic acid lactone Hydroxynonanoic acid, a-lactone
Butyl 2-hydroxypropanoate Butyl lactate
n- Butylideneacetone 3-Hepten-2-one
2-isoButyl-5-methylcyclohexanol d-neo-Menthol
Butyl isopentanoate Butyl isovalerate
Butyl4-ketovalerate Butyllevulinate
n- Butyl mercaptan 1-Butanethiol
Butyl3-methylbutanoate Butyl isovalerate
isoButyl methyl ketone 4-Methyl-2-pentanone
Butyl 2-methylpropanoate Butyl isobutyrate
isoButyl2-methylpropanoate Isobutyl isobutyrate
Butyl octadecanoate Butyl stearate
Butyl 3-oxobutanoate Butyl acetoacetate
Butyl para ben (Parasept) Butylp-hydroxybenzoate
Butyl sebacate Dibutyl sebacate
2-sec-Butylthiazole 2-( 1-Methylpropyllthiazole
5-n-Butyl-o-valerolactone Hydroxynonanoic acid, a-lactone
Butyrin (Tril-Butyrin
Butyroin 5-Hydroxy-4-octanone
'Y-Butyrolactone 4-Hydroxybutanoic acid lactone
Butyrone 4-Heptanone
Butyryl acetyl 2,3-Hexanedione
Buxine a- Amylcinnamaldehyde
Cajeputene d-Limonene
Cajeputol Eucalyptol
2-Camphanyl acetate Bornyl acetate
Capraldehyde Dec anal
Capraldehyde dimethyl acetal Decanal dimethyl acetal
Capric acid Decanoic acid
Capric alcohol 1-Decanol
Capric aldehyde Dec anal
Caproic acid Hexanoic acid
Caproic alcohol Hexyl alcohol
Caproic aldehyde Hexanal
'Y-Caprolactone 'Y-Hexalactone
o-Caprolactone 6-Hexalactone
Capronylethanol 3-0ctanon-1-ol
Capryl alcohol 2-0ctanol
Capryl aldehyde Octanal
Caprylaldehyde dimethyl acetal Octanal dimethyl acetal
Caprylic acid Octanoic acid
Caprylic alcohol 1-0ctanol
Capsaicin N -( 4-Hydroxy- 3-methoxy benzyl)- 8-methyl-6-
nonenamide
iso-Carveol p- Mentha -1 ,8-dien -7 -ol
Carvomenthone p-Menthan-2-one
Caryolan-1-ol Caryophyllene alcohol
Caryophyllene acetate Caryophyllene alcohol acetate
C-8 dimethyl acetal Octanal dimethyl acetal
Celery ketone 3-Methyl-5-propyl-2-cyclohexen-1-one
a-Cetone Methyl-a-ionone
{3-Cetone Methyl-/3-ionone
 Organic Chemicals Used in Flavorings and Fragrances 519

Synonym Refer to Chemical Listed in Main Tabular Body

Cetone-d Methyl/3-naphthylketone
Cetone-V All~l a-ionone
Cetyl alcohol 1-Hexadecanol
Chavicyl methyl ether Estragole
2-Chromanone Dihydrocoumarin
Cineole Eucalyptol
Cinnamic alcohol Cinnamyl alcohol
Cinnamic aldehyde Cinnamaldehyde
Cinnamylic acid Cinnamic acid
Cinnamyl 3-methylbutanoate Cinnamyl isovalerate
Cinnamyl 2-methylpropanoate Cinnamyl isobutyrate
Cinnamyl 13-phenylacrylate Cinnamyl cinnamate
Cinnamyl a-toluate Cinnamyl phenylacetate
Citronellic acid 3, 7-Dimethyl-6-octenoic acid
Civetone Cycloheptadeca-9-en-1-one
Coconut aldehyde 'Y-Nonalactone
Compound 1010 3-0ctanon-1-ol
Coriandrol Linalool
Cortexal p- lsopropylphenylacetaldehyde
Creosol 2-Methoxy-4-methylphenol
o-Cresyl acetate o-Tolyl acetate
p-Cresyl acetate p-Tolyl acetate
p-Cresyl dodecanoate e-Tolyllaurate
2-(o-, m- or p-Cresyl)-5-hydroxymethyldioxolane Tolualdehyde glyceryl acetal
Cumaldehyde Cuminaldehyde
o-Cuminol 2-lsopropylphenol
Cuminal Cuminaldehyde
Cumin alcohol p- Isopropyl benzene alcohol
Cuminylacetaldehyde 3-(p-lsopropylphenyl)propionaldehyde
Cuminyl alcohol p- Isopropyl benzyl alcohol
Cyclamal 2-Methyl-3-Y,-isopropylphenyl)propionaldehyde
Cyclamen aldehyde 2-Methyl-3-VJ-isopropylphenyl)propionaldehyde
a-Cyclocitrylideneacetone a-ionone
13-Cyclocitrylideneacetone 13-ionone
a-Cyclocitrylidenebutanone Methyl a-ionone
13-Cyclocitrylidenebutanone Methyl tl-ionone
Cyclo-1, 13-ethylenedioxytridecan-1, 13-dione Ethylene glycol brassylate, cyclic diester
1,2-Cyclohexanedione 2-Hydroxy-2-cyclohexen-1-one
Cyclohexapyrazine 5,6, 7 ,8-Tetrahydroquinoxaline
Cyclopentadecanolide w- Pentadecalactone
Cyclosal 2-Methyl-3-(p-isopropylphenyl)propionaldehyde
Cyclotene Methylcyclopentenolone
p-Cymen -7 -carboxaldehyde p-lsopropylphenylacetaldehyde
Damascenone (Damasione) 4-(2,6,6-Trimethylcyclohexa-1 ,3-dienyl)but-2-en-4-one
Decanolide-1 ,4 'Y-Decalactone
Decanolide-1 ,5 li-Decalactone
Decanyl acetate Decyl acetate
Decenaldehyde Decenal
3-Decylacrolein 2-Tridecanal
Decyl alcohol 1-Decanol
n-Decyl aldehyde Decanal
Dehydro-/3-cyclocitral 2,6,6-Trimethylcyclohexa-1 ,3-dienyl methanal
Delphinic acid Isovaleric acid
Diallyl sulfide Allyl disulfide
Diasmol 1,3-Nonanediol acetate
Dibenzyl ketone 1,3-Diphenyl-2-propanone
Dibutylbutyrolactone 4,4-Dibutyl-'Y-butyrolactone
Dibutyl1,8-octandicarboxylate Dibutyl sebacate
1,1-Diethoxyethane Acetal
Diethylacetaldehyde 2-Ethylbutryaldehyde
Diethyl anthranilate Ethyl n-ethylanthranilate
Diethyl butanedioate Diethyl succinate
Diethyl decanedioate Diethyl sebacate
Diethyl2,3-dihydroxybutanedioate Diethyl tartrate
Diethyl diketone 3,4-Hexanedione
Diethyl2-hydroxybutanedioate Diethyl malate
Difurfuryl disulfide Bis-(2-furfuryl) disulfide
Dihydroanethole p- Propyl anisole
2,3-Dihydrobutanedioic acid Tartaric acid
Dihydrocinnamic acid 3-Phenylpropionic acid
Dihydrocinnamyl alcohol 3-Phenyl-1-propanol
520 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

Dihydrocitronellol 3,7-Dimethyl-1-octanol
Dihydrocuminic alcohol p-Mentha-1,8-dien-7-ol
Dihydrocuminyl acetate Perillyl acetate
Dihydro-p-cymene a- Phellandrene
Dihy_drogeranylacetone Tetrahydro-pseudo-ionone
3,4-Dihydro-2H -1-benzopyran-2-one Dihydrocoumarin
Dihy_drojasmone iso-Jasmone
2,3-Dihydrotoluene 1-Methyl-1,3-cyclohexadiene
2,4-Dihydroxy-3-methyl-2-hexenoic acid, 'Y-Iactone 5-Ethyl-3-hydroxy-4-methyi-2(5H)-furanone
1-(x,y-Dihydroxyphenyl)ethanone Dioxyacetophenone
1,2-Dihydroxypropane Propylene glycol
2,3-dihydroxysuccinic acid Tartaric acid
3,4-Dimethoxy benzaldehyde Veratraldehyde
1,1-Dimethoxydecane Decanal dimethyl acetal
1,1-Dimethoxy-3, 7 -dimethyl-2,6-octadiene Citra! dimethyl acetal
1,1-Dimethoxy-3, 7 -dimethyl-7 -octanol Hydroxycitronellal dimethyl acetal
1,1-Dimethoxyheptate Heptanal dimethyl acetal
1,1-Dimethoxyoctane Octanal dimethyl acetal
1,1-Dimethoxy-2-phenylethane Phenylacetaldehyde dimethyl acetal
1,2-Dimethoxy-4-(2-propen-1-yl)benzene Eugenyl methyl ether
1,2-Dimethoxy-4-(1-propen-1-yl)benzene Isoeugenyl methyl ether
3,4-Dimethoxy-1-( 1-propen-1-yl)benzene Isoeugenyl methyl ether
a ,a-Dimethoxytoluene Benzaldehyde dimethyl acetal
Dimethyl acetal 1,1-Dimethoxyethane
2,5-Dimethyl-3-acetylfuran 3-Acetyl-2,5-dimethylfuran
3,3-Dimethylacrylic acid 3-Methylcrotonic acid
a ,a-Dimethylanisalacetone 1-( 4-Methoxyphenyl)-4-methyl-1-penten -3-one
Dimethyl anthranilate Methyl N-methylanthranilate
Dimethyl benzyl carbinol a,a-Dimethylphenethyl alcohol
4,5-Dimethyl-2-benzyl-1,3-dioxolane Phenylacetaldehyde-2,3-butylene glycol acetal
Dimethyl butanedioate Dimethyl succinate
Dimethyl carbinol Isopropyl alcohol
Dimethyl benzyl carbinyl acetate a,a-Dlmethylphenethyl acetate
2,4-Dimethylcrotonaldehyde 2-Methyl-2-pentenal
1,4-Dimethylcyclohex-3-enyl methyl ketone 1,4-Dimethyl-4-acetyl-1-cyclohexane
2,3-Dimethyl-1,4-diazine 2,3-Dimethylpyrazine
Dimethyl diketone Diacetyl
Dimethyl disulfide Methyl disulfide
Dimethyl ether protocatechualdehyde Veratraldehyde
2,6-Dimethyl-3-ethylpyrazine 3-Ethyl-2,6-dimethylpyrazine
Dimethylglyoxal Diacetyl
Dimethyl hydroquinone p- Dimethyoxybenzene
1,4-Dimethyl-7 -(a-hydroxy-isopropyiH-9, 10- Guaiol acetate
octahydroazulene acetate
3,7-Dimethyl-7-hydroxyoctanal Hydroxycitronellal
Dimethylketol Acetoin
Dimethyl ketone Acetone
6,6-Dimethyl-2-methylenebicyclo(3.1.1)heptane {3-Pinene
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten- 'Y-Ionone
2-one
2,6-Dimethylphenol 2,6-Xylenol
Dimethyl resorcinol m-Dimethyoxybenzene
Dimethyl salicylate Methyl o-methoxybenzoate
Dimethyl sulfide Methyl sulfide
Dimethyl p-tolyl carbinol p-a,a-Trimethylbenzyl alcohol
6,10-Dimethyl-9-undecen-2-one Tetrahydro-pseudo-ionone
2,6-Dinitro-3-methoxy-1-methyl-4-tert-butyl-benzene Musk ambrette
Dioxymethylene protocatechuic aldehyde Piperonal
Dipentene d-Limonene
Diphenyl Biphenyl
Diphenyl ketone Benzophenone
Dipropionyl 3,4-Hexanedione
Dipropyl ketone 4-Heptanone
2,2'-Dithiodithiophene 2-Thienyl disulfide
Dithioglycol 1,2-Ethanedithiol
Divinyleneimine Pyrrole
Dodecanal Lauric aldehyde
Dodecanoic acid Lauric acid
1-Dodecanol Laury! alcohol
Dodecanolide-1,4 'Y-Dodecalactone
Dodecanolide-1 ,5 /i-Dodecalactone
 Organic Chemicals Used in Flavorings and Fragrances 521

Synonym Refer to Chemical Listed in Main Tabular Body

Dodecanyl acetate Laury! acetate
Enanthic acid Heptanoic acid
1,8-Epoxy-p-menthane Eucalyptol
1,6-Epoxy-p-men th -8-en- 2-one Carvone oxide
1,2-Epoxy-p-men th -4(8 )-en -3-one Piperi tenone oxide
iso- Estragole Anethole
3-Ethoxy-4-hydroxy benzaldehyde Ethyl vanillin
Ethyl acetic acid Butyric acid
3-Ethylacrolein 2-Pentenal
Ethyl n-amyl carbinol 3-0ctanol
Ethyl amyl ketone 3-0ctanone
a-Ethylbenzyl alcohol 1-Phenyl-1-propanol
Ethyl butanoate Ethyl butyrate
Ethyl2-butenoate Ethyl crotonate
2-Ethyl-3- butylacrolein 2-Ethyl-2-heptenal
Ethyl butyl ketone 3-Heptanone
Ethyl butyralactone 'Y- Hexalactone
Ethyl caprate (caprinate) Ethyl decanoate
Ethyl caproate Ethyl hexanoate
Ethyl caprylate Ethyl octanoate
Ethyl2-carboxyglutaconate Ethyl aconitate
Ethyl a-crotonate Ethyl trans-2-butenoate
Ethyl decanedioate Diethyl sebacate
Ethyl decylate Ethyl decanoate
2-Ethyl-1,4-diazine 2-Ethylpyrazine
3-Ethyl-2,5-dimethylpyrazine 2-Ethyl-3(5 or 6)-dimethylpyrazine
Ethyl dodecanoate (dodecylate) Ethyllaurate
Ethyl a, {3-epoxy-{3-phenylpropionate Ethyl3-phenylglycidate
Ethyl2,3-epoxy-2-methyl-3-phenylpropionate Ethyl methylphenylglycidate
Ethyl furfurylhydracrylate Ethyl2-furanpropionate
-y-Ethyl--y-butyrolactone -y- Hexalactone
Ethylheptoate(heptanoate) Ethyl heptylate
Ethylhexadecanoate Ethyl palmitate
Ethyl2,4-hexadienoate Ethyl sorbate
2-Ethylhexyl acetate Octyl acetate
Ethylhexylketone 3-Nonanone
4-Ethyl-4-hydroxybutanoic acid lactone 'Y Hexalactone
Ethyl 2-hydroxypropanoate Ethyl lactate
2-Ethyl-3-hydroxy-4H -pyran-4-one Ethyl maltol
Ethylidene dimethyl ether 1,1-Dimethoxyethane
Ethylidene diethyl ether Acetal
2-Ethylidenehexanal 2-Butyl-2-butenal
Ethyl trans-2-methyl-2-butenoate Ethyl tiglate
3-Ethyl-4-methylcyclotene 3-Ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one
Ethyl methyl ketone 2-Butanone
Ethyl cis-9-octadecanoate Ethyl oleate
Ethyl octyne carbonate Ethyl2-nonynoate
Ethyl oxyhydrate Rum ether
Ethyl pelargonate Ethyl nonanoate
Ethylpentanoate Ethyl valerate
Ethyl phenylacrylate Ethyl cinnamate
Ethyl3-phenyl-2,3-epoxypropionate Ethyl 3-phenylglycidate
2-Ethylphenyl mercaptan 2-Ethylthiophenol
Ethyl propyl carbinol 3-Hexanol
Ethyl propyl ketone 3-Hexanone
2-Ethylpyromeconic acid Ethyl mal to!
Ethyl stearate Ethyl octadecanoate
Ethyl succinate Diethyl succinate
Ethyl tartrate Diethyl tartrate
Ethyl tetradecanoate Ethyl myristate
Ethyl thiolactate Ethyl2-mercaptopropionate
Ethyl a-toluate Ethyl phenylacetate
Exaltolide w- Pentadecalactone
2-Fenchanol Fenchyl alcohol
d-2- Fenchanone d-Fenchone
Fenchyl acetate 1,3,3-Trimethyl-2-norbornanyl acetate
Flomine a- Amylcinnamaldehyde
2-Formylbenzofuran 2-Benzofurancarboxaldehyde
1-Formyl-2,4-dimethylbenzene 2,4-Dimethyl benzaldehyde
2-Furaldehyde Furfural
2-Furanmethanethiol Furfuryl mercaptan
522 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

Furfuralactone 4-(2-Furyl)-3-buten-2-one
a- Furfuryl caprylate a- Furfuryl octanoate
2-Furfuryl disulfide 2,2' -(Dithiodimethylene)-difuran
Furfuryl disulfide Bis-(2-furfuryl) disulfide
Furfurylidene acetone 4-(2-Furyl)-3-buten-2-one
Furfuryl isovalerate Furfuryl 3-methylbutanoate
2-Furfuryl monosulfide 2,2' -(Thiodimethylene)-difuran
1-(2-Furfuryl)pyrrole N-Furfurylpyrrole
a-Furfuryl valerate a- Furfuryl pentanoate
Furoyl acetone 1-(2-Furyl)-1,3,-butanedione
Furyl acetone 2-Furyl-1 ,3-propanone
Geranial Citra!
Geranyl caproate Geranyl hexanoate
Geranyl 2-ethylbutyrate 3,7-Dimethylocta-2,6-dienyl2-ethylbutanoate
Geranyl(i-ketobutyrate Geranyl acetoacetate
Geranyl 3-methylbutanoate Geranyl isovalerate
Geranyl 2-methylpropanoate Geranyl isobutyrate
Geranyl a-toluate Geranyl phenylacetate
Glucosaccharonic acid Erythorbic acid
Glycerine Glycerol
Glyceryl triacetate (tri)-Acetin
Glyceryl tributyrate (tri}- Butyrin
-y-Oxopentanoic acid Levulinic acid
Gum camphor d-Camphor
HCA a-Hexylcinnamaldehyde
Heliotropine Piperonal
Heliotropyl acetate Piperonly acetate
Heliotropyl 2-methylpropanoate Piperonyl isobutyrate
1,4-Hendecanolide -y-U ndecalactone
2-Hendecanone 2-Undecanone
Hendeca-9-al 9-Undecanal
Hendecylmethyl ketone 2-Tridecanone
Heptanolide-1,4 -y-Heptalactone
3-Heptylacrolein 2-Decenal
-y_-Heptyl butyrolactone -y-Undecalactone
Heptylidenealdehyde 2-Nonenal
Heptylidene acetone 3-Decen-2-one
-y-Heptyl--y-valerolactone -y- Dodecalactone
Hexadecanoic acid Palmitic acid
6-hexadecenolide w-6-Hexadecenlactone
Hexahydropyridine Piperidine
Hexahydrothymol Menthol
Hexamethylene dimercaptan 1.6-Hexanedithiol
Hexanolide-1,4 'Y- Hexalactone
Hexanoylethanol 3-0ctanon -1-ol
2-Hexanoylfuran Pentyl 2-furyl ketone
Hex one 4-Methyl-2-pentanone
3-Hexylacrolein 2-Nonenal
-y-Hexyl--y-butyrolactone 'Y- Decalactone
Hexylene glycol diacetate 1,3-Nonanediol acetate (mixed esters)
2-Hexyl-4-hydroxy-1,3-dioxane Heptanalglyceryl acetal (mixed 1,2- and 1,3-acetals)
2-Hexylidene cyclopentanone ) mixture iso-Jasmone
2-Hexyl-2-cyclopenten-1-one )
Hexyl isovalerate Hexyl3-methylbutanoate
Hexyl methyl ketone 2-0ctanone
3-Hexyl-1, 3-propanediol acetate 1,3-Nonanediol acetate
6-Hexyl-6-valerolactone 5-Hydroxyundecanoic acid lactone
Homoanisaldehyde p- Ethoxybenzaldehyde
Homocatechol monomethyl ether 2-Methoxy-4-methylphenol
(i-Homocyclocitral 2,6,6-trimethyl-1-cyclohexen-1-acetaldehyde
Hyacinthin Phenylacetaldehyde
Hydratropaldehyde 2-Phenylpropionaldehyde
Hydra tropic alcohol (i-Methylphenethyl alcohol
Hydrocinnamaldehyde 3-Phenylpropionaldehyde
Hydrocinnamyl alcohol 3-Phenyl-1-propanol
2-Hydrocinnamyl tetrahydrofuran 2-( 3-Phenylpropyl)-tetrahydrofuran
Hydrocoumarin Dihydrocoumarin
Hydroquinone dimethyl ether p- Dimethyoxy benzene
o-Hydroxyanisole Guaiacol
2-Hydroxy benzaldehyde Salicylaldehyde
p- Hydroxybenzylacetone 4-(p-Hydroxyphenyl)-2-butanone
 Organic Chemicals Used in Flavorings and Fragrances 523

Synonym Refer to Chemical Listed in Main Tabular Body

5-Hydroxy-2-benzyl-1,3-dioxan Phenylacetaldehyde glyceryl acetal
2-Hydroxy-3-butanethiol 2-Mercapto-3-butanol
3-Hydroxy-2-butanethiol 2-Mercapto-3-butanol
3-Hydroxy-2-butanone Acetoin
2-Hydroxycamphane Borneol
2-Hydroxy-p-cymene Carvacrol
3-Hydroxy-p-cymene Thymol
5-Hydroxydecanoic acid, 6-lactone 6-Decalactone
4-Hydroxydecanoic acid, 'Y-lactone ')'-Decalactone
o-Hydroxydihydrocinnamic acid lactone Dihydrocourmarin
2-Hydroxy-1,3-dimethoxybenzene 2,6-Dimethoxyphenol
5-Hydroxydodecanoic acid, 6-lactone 6-Dodecalactone
4-Hydroxydodecanoic acid, 'Y-lactone 'Y -Dodecalactone
4-(a-Hydroxyethyl)toluene p,a- Dimethylbenzyl alcohol
2-Hydroxyheptane 2-Heptanol
4-Hydroxyheptanoic acid, -y-lactone 'Y-Heptalactone
16-Hydroxy-6-hexadecenmc acid, w-lactone w-6- Hexadecenlactone
4-Hydroxy hexanoic acid, 'Y-lactone 'Y-Hexalactone
5-Hydroxyhexanoic acid lactone 6-Hexalactone
4-Hydroxy-3-methoxy-1-allylbenzene Eugenol
4-Hydroxy-3-methoxybenzaldehyde Vanillin
1-Hydroxy-2-methoxybenzene Guaiacol
4-Hydroxy-3-methoxybenzyl acetone Zingerone
4-Hydroxy-3-methoxybenzyl alcohol Vanillyl alcohol
N -( 4-Hydroxy-3-methoxybenzyl)nonanamide Nonanoyl-4-hydroxy-3-methoxybenzylamine
1-Hydroxy-2-methoxy-4-ethylbenzene 4-Ethylguaiacol
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene isoEugenol
4-Hydroxy-3-methoxystyrene 2-Methoxy-4-vinylphenol
Hydroxymethyl anethole Propenylguaethol
1-Hydroxy-4-methylbenzene p-Cresol
2-Hydroxy-1-methylbenzene o-Cresol
1-Hydroxy-3-methylbenzene m-Cresol
2-Hydroxymethylfuran Furfuryl alcohol
1-Hydroxy-2-methylmercaptobenzene o-(Methylthio)-phenol
4-Hydroxymethyl-2-phenyl-m-dioxolane Benzaldehyde glyceryl acetal
2-Hydroxy-2-methyl-1 ~phenylpropane a,a-Dimethylphenethyl alcohol
3-Hydroxy-2-methyl-4H -pyran-4-one Maltol
4-Hydroxynonanoic acid, 'Y-lactone 'Y-Nonalactone
5-Hydroxynonanoic acid, 6-latone 6-Nonalactone
4-Hydroxyoctanoic acid, 'Y-lactone 'Y -Octalactone
5-Hydroxyoctanoic acid, 6-lactone 6-0ctalactone
4-Hydroxypentanoic acid, 'Y-lactone -y- Val~rolactone
a- Hydroxy-a -phenylacetophenone Benzom
a-Hydroxypropanoic acid Lactic acid
a-Hydroxypropylbenzene 1-Phenyl-1-propanol
'Y-Hydroxypropyl methyl sulfide 3-(Methylthio)propanol
1-Hydroxysuccinic acid 1-Malic acid
a-Hydroxytoluene Benzyl alcohol
(o-, p- or m-)- Hydroxytoluene (o-,p- orm-)-Cresol
p- Hydroxytricarboxylic acid Citric acid
4-Hydroxyundecanoic acid, 'Y -lactone -y-Undecalactone
lmidole Pyrrole
IPA Isopropyl alcohol
IHraldeine Methyl-~-ionone
Iraldeine gamma a-iso- Methylionone
(a or ~Hrisone (a or ~Honone
Isoacetophorone lsophorone
Isoamyl aldehyde 3-Methylbutyraldehyde
Isoamylamine lsopentylamine
Isoanethole Estragol
Isoascorbic acid Erythorbic acid
2-Isobutoxynafhthalene ~-Naphthyl isobutyl ether
Isobutylbenzy ketone 4-Methyl-1-phenyl-2-pentanone
Isobutyl ketone 2,6-Dimethyl-4-heptanone
2-Isobutyl-5-methylcyclohexanol d-neo-Menthol
Isobutyl methyl ketone 4-Methyl-2-pentanone
Isopentyl alcohol Isoamyl alcohol
Isopentyl esters Isoamyl esters
Isoanethole Estragole
Isoascorbic acid Erythrobic acid
Isobornyl alcohol Isobomeol
524 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

Isobornylethanoate Isobornyl acetate
I sobutanol Isobutyl alcohol
2-lsobutoxynaphthalene ~-Naphthyl isobutyl ether
Isobutyl aldehyde Isobutyraldehyde
Isobutyl benzyl carbinol a- Isobutylphenethyl alcohol
Isobutyl benzyl ketone 4-Methyl-1-phenyl-2-pentanone
Isobutyl caproate Isobutylhexanoate
Isobutyl carbinol Isoamyl alcohol
Isobutyl carbylamine lsopentylamine
lsobutylcrotonate lsobutyl2-butenoate
Isobutyl ethanoate Isobutyl acetate
Isobutyl formic acid Isovaleric acid
Isobutyl furylpropionate Isobutyl2-furanpropionate
Isobutyl heptoate Isobutylheptanoate
Isobutyl o-hydroxybenzoate Isobutyl salicylate
Isobutyl isovalerate 2-Methylpropyl3-methylbutyrate
Isobutyl ketone 2,6-Dimethyl-4-heptanone
Isobutyl methanoate Isobutyl formate
Isobutyl 2-N -methylaminobenzoate Isobutyl N -methylanthranilate
Isobutyl cis-2-methyl-2-butenoate Isobutyl angelate
2-lsobutyl-5-methylcyclohexanol d-neo-Menthol
Isobutyl meth}'l ketone 4-Methyl-2-pentanone
Isobutyl 2-methylpropanoate Isobutyl isobutyrate
Isobutyl~-naphthyl ether 8-Naphthyl isobutyl ether
Isobutyl3-oxobutanoate lsobutylacetoacetate
Isobutyl ~-phenylacrylate Isotiutyl cinnamate
2-lsobutylpyridine 2-(2-Methylpropyl)pyridine
3-lsobutylpyridine 3-(2-Methylpropyl)pyridine
Isobutyl a-toluate Isobutyl phenylacetate
Isobutyric acid, benzyl ester Benzyl isobutyrate
Isocaproic acid 4-Methylpentanoic acid
lsodecenoic acid vanillylamide N -( 4-Hydroxy-3-methoxybenzyl)-8-methyl-6-
nonenamide
lsodecylaldehyde 2,6-Dimethyloctanal
Isoestragole Anethole
lsoeugenol iso-Eugenol
lsoeugenylacetate iso-Eugenyl acetate
Isoeugenol methyl ether lsoeugenyl methyl ether
Iso~ugenyl a-toluate lsoeugenyl phenylacetate
Isohexanoic acid 4-Methylpentanoic acid
Isohexanone 4-Me~hyl-2-pentanone
a-lsomethylionone a-iso-Methylionone
Isopentaldehyde 3-Methylbutryaldehyde
lsopentyl acetoacetate Isoamyl acetoacetate
lsopentyl alcohol Isoamyl alcohol
lsopentyl esters Isoamyl esters
Isopropanol Isopropyl alcohol
4-lsopropenyl-1-cyclohexenecarbinol p-Mentha-1,8-dien-7-ol
4-lsopropenyl-1-cyclohexene-1-carboxaldehyde Perillaldehyde
2-lsopropenyl-1,4-diazine lsopropenylpyrazine
p- lsopropenyltoluene p-a -Dimethylstyrene
Isopropyl acetic acid Isovaleric acid
Isopropyl acetone 4-Methyl-2-pentanone
p- lsopropylacetylbenzene p- Isopropylacetophenone
p- Isopropylbenzaldehyde Cummali:lehyde
4-lsopropylbenzenecarboxaldehyde Cuminaldehyde
lsopropyl-o-cresol Carvacrol
6-Isopropyl-m -cresol Thymol
lsopropylformic acid Isobutyric acid
p- lsopropylhydrocinnamaldehyde 3-(p-lsopropylphenyl)propionaldehyde
Isopropylidene acetone 4-Methyl-3-penten-2-one
1-lsopropylidene-4-methyl-2-cyclohexanone Pulegone
5-Isopropyl-2-methyl-1,3-cyclohexadiene a- Phellandrene
4-lsopropyl-1-methyl-1,5-cyclohexadiene a- Phellandrene
1-lsopropyl-4-methylcyclohexan-2-ol Menthol
4-Isopropyl-1-methylcyclohexan-3-one Menthone
1-Isopropyl-4-methyl-2-cyclohexanone lsoj>ulegone
4-lsopropyl-1-methyl-1-cyclohexen-3-one d-Piperitone
1-lsopropyl-4-methylcyclohexen-2-yl acetate Menthyl acetate
1-lsopropyl-4-methylcyclohexen-2-yl Menthyl isovalerate
3-methylbutanoate
 Organic Chemicals Used in Flavorings and Fragrances 525

Synonym Refer to Chemical Listed in Main Tabular Body

Isopropyl methyl ketone 4-Methrl-2,3-pentadione
2-lsopropyl-5-methylphenol Thymo
2-lsopropyl-5-methylpyrazine 2-Methyl-5-isopropylpyrazine
2-lsopropyl-(3,5 or 6)-methoxypyrazine 2-Methoxy-(3,5 or 6)-lsopropylpyrazine
p- Isopropyltoluene p-Cymene
2-lsopropyl-5-methylcyclohexanol d-neo-Menthol
I sothymol Carvacrol
Isovaleraldehyde 3-Methylbutyraldehyde
Isovalerone 2,6-Dimethyl-4-heptanone
Jasmine aldehyde (Jasmonal) a-Amylcinnamaldehyde
JasmonalH a-Hexylcinnamaldehyde
cis-Jasmone 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
Ketone alcohol 3-0ctanon-1-ol
2-Ketopropionaldehyde Pyruvaldehyde
2-Ketopropionic acid Pyruvic acid
2-Keto-1, 7, 7-trimethylnorcamphane d-Camphor
"'" Ketovaleric acid Levulinic acid
Labdanol Isobutyl cinnamate
Laurine Hydroxycitronellal
Laury! isobutyrate Dodecyl isobutyrate
Leaf alcohol 3-Hexen-1-ol
Leaf aldehyde 2-Hexenal
Lepidine 6-Methylquinoline
Leucoline Quinoline
Matsuka alcohol 1-0cten-3-ol
Melonal 2,6-Dimethyl-5-heptenal
p- Mentha-1,8-dien-7 -al Perillaldehyde
p-1,8(9)-Menthadiene d-Limonene
p- Mentha-1,5-diene a- Phellandrene
p- Mentha-1,4(8)-diene Terpin'?lene
p-Mentha-1,3-diene a-Terpmene
p- Mentha-6,8-dien-2-ol Carveol
p- Mentha-1,8( 10)-dien-9-ol Menthadienol
6,8(9 )-p-Menthadien-2-one Carvone
p- Mentha -6,8-dien-2-one Carvone
p- Mentha-1,4(8)-dien-3-one Piperitenone
p-Mentha-6,8-dien-2-yl esters Carvyl esters
1-p- Menthen-4-ol 4-Carvomenthenol
8-p- Menthen-2-ol Dihydrocarveol
p-Menth-8-en-1-ol a-Terpineol
p-Menth-8-en-1-ylesters Terpinyl esters
p- Menth-1-en-3-one d-Piperitone
p- Menth-4(8)-en-3-one Pulegone
p-Menth-3-ylesters Menthyl esters
3-Mercapto-2-butanol 2-Mercapto-3-butanol
4-Mercapto-2-butanone 2-Keto-4-butananethiol
8-Mercapto-p-menthan-3-one p-Mentha-8-thiol-3-one
2-Mercaptonaphthalene 2-N aphthalenethiol
a- Mercaptotoluene Benzyl mercaptan
Mesityl oxide 4-Methyl-3-penten-2-one
Methanethiol Methyl mercaptan
Methialdol 2,8-Dithianon-4-en-4-carboxaldehyde
Methional 3-(Methylthio)propionaldehyde
p-Methoxyacetophenone Acetanisole
3-Methoxy-4-acetoxybenzaldehyde Vanillin acetate
p- Methoxyallylbenzene Estragole
2-Methoxy-4-allylphenol Eugenol
Methoxybenzene Anisole
4 (or p)-Methoxybenzyl esters Anisyl esters
2-Methoxy-3-sec-butylpyrazine 2-Methoxy-3-( 1-methylpropyl)pyrazine
2-Methoxy-p-cresol 2-Methoxy-4-methylphenol
3-Methoxy-p-cymene 1-Methyl-3-methoxy-4-isopropylbenzene
2-Methoxy-1,4-diazine Methoxypyrazine
2-Methoxy-4-ethylphenol 4-Ethylguaiacol
3-Methoxy-4-hydroxybenzaldehyde Vanillin
3-Methoxy-4-hydroxybenzylacetone Zingerone
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene iso- Eugenol
3-Methoxy-4-hydroxytoluene 2-Methoxy-4-methylphenol
o-Methoxy-methyl benzoate Methyl o-methoxybenzoate
o-Methoxyphenol Guaiacol
o-Methoxy esters Guaiacyl esters
526 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

p-Methoxypropenylbenzene Anethole
1-Methoxy-4-(2-propen-1-yl)benzene Estragole
2-Methoxy-4-(2-propen-1-yl)phenol Eugenol
2-Methoxy-4-propenylphenol iso-Eugenol
2-Methoxy-4-propenylesters iso- Eugenyl esters
1-Methoxy-4-propylbenzene p-Propyl anisole
2-Methoxystyrene o- Vinylanisole
2-Methoxytoluene o- Methylanisole
4-Methoxytoluene p- Methylanisole
1-Methoxy-2-vinylbenzene o- Vinylanisole
Methylacetaldehyde Propionaldehyde
Methylacetic acid Propionic acid
Methyl allyl disulfide Allyl methyl disulfide
Methylamylacetic acid 2-Methylheptanoic acid
Methyl amyl ketone 2-Heptanone
Methyl ben Methyl p- Hydroxy benzoate
Methyl benzaldehyde Tolualdehyde
6-Me thy 1- 2H -1-benzopyran- 2-one 6-Methylcoumarin
6-Methy lbenzopyrone 6-Methylcoumarin
Methyl butanedioate Dimethyl succinate
3-Methyl butanoic acid Isovaleric acid
3-Methyl-1- butanol Isoamyl alcohol
a-Methylbutanol 2-Pentanol
3-Methyl butyl esters Isoamyl esters
'Y- Methyl--y-butyrolactone -y- Valerolactone
Methylcatechol Guaiacol
Methyl chavicol Estragole
Methyl citronellate Methyl3,7-dimethyl-6-octenoate
6-Methyl-cis-o-coumarinic lactone 6-Methylcoumarin
2-Methylcrotonaldehyde 2-Methyl-2-butenal
2-Methyl-1,4-diazine 2-Methylpyrazine
Me thy ldi thiopropane Methyl propyl disulfide
4-(2-M ethylene-6, 6 -dimethy lcyclohexy1)- 3- -y-lonone
buten-2-one
3,4-Methylenedioxybenzaldehyde Piperonal
3,4-Methylenedioxybenzyl acetate Piperonylacetate
3,4-Methylenedioxy benzyl 2-methylpropanoate Piperonyl isobutyrate
2-Methylene-6, 10,1 0-trimethylbicyclo( 7.2 .0 )- !3-Caryophyllene
undec-5-ene
Methyl ethyl ketone 2-Butanone
1-Methylethyl 3-phenylpropenoate Isopropyl cinnamate
2-Methyl-5-ethylpyrazine 2-Ethyl-5-methylpyrazine
Methyl eugenol Eugenyl methyl ether
Methylexaltone 3-Methyl-1-cyclopentadecanone
5-Methyl- 2( 3H)-furanone 4-Hydroxy-3-pentenoic acid lactone
2-Methyl- 3-furylacrolein Furfurylidene-2-propanol
Me thy I glycol Propylene glycol
Me thy I glyoxal Pyruvaldehyde
4-Methylguaiacol 2-Methoxy-4-methylphenol
2-Methylhepta-2,4-dien-6-one 6-Methyl-3,5-heptadien-2-one
2-Methyl-2-hepten-6-one 6-Methyl-5-hepten-2-one
Methyl heptine carbonate Methyl2-octynoate
Methyl n-heptyl carbinol 2-Nonanol
Methylheptylketone 2-Nonanone
Methyl hexyl ketone 2-0ctanone
p- Methylhydra tropaldehyde 2-{p-Tolyl)-propionaldehyde
1-Methyl-4-hydroxybenzene p-Cresol
1-Methyl-3-hydroxybenzene m-Cresol
4-Methyl-4-hydroxybutanoic acid lactone y- Valerolactone
1-Methyl-3-hydroxy-4-isopropylbenzene Thymol
5-Methyl-5-hydroxypentanoic acid lactone o- Hexalactone
5-Methyl-2-hydroxyphenylpropenoic acid lactone 6-Methylcoumarin
!3-Methylindole Skatole
6-Me thy lionone a-lrone
!3-Methylionone a-iso-Methylionone
1-Methyl-4-isopropenylbenzene p,a- Dimethylstyrene
6-Methyl-3-isopropenylcyclohexanol Dihydrocarveol
1-Methyl-4-isopropenylcyclohexan -3-ol lsopulegol
1-Methyl-4-isopropenylcyclohexan-1-ol !3- Terpineol
1-Methyl-4-isopropenyl-1-cyclohexane d-Limonene
1· Me thy 1-{ -isopropenyl-6-cyclohexen-2-ol Carveol
 Organic Chemicals Used in Flavorings and Fragrances 527

Synonym Refer to Chemical Listed in Main Tabular Body

1-Methyl-4-isopropenyl-6-cyclohexen-2-one Carvone
1-Methyl-4-isopropylbenzene p-Cymene
1-Methyl-4-isopropyl-1,5-cyclohexadiene a- Phellandrene
1-Methyl-4-isopropyl-1,3-cyclohexadiene a-Terpinene
1-Methyl-4-isopropyl-1,4-cyclohexadiene ')'-Terpinene
1-Methyl-4-isopropylcyclohexan-3-ol Menthol
1-Methyl-4-isopropyl-2-cyclohexanol Carvomenthol
cis-1- Methyl-4-isopropyl-3-cyclohexanone dl-Isomenthone
1-Methyl-4-isopropyl-1-cyclohexen-8-ol a-Terpineol
1-Methyl-4-isopropyl-1-cyclohexen-3-one d-Piperitone
1-Methyl-4-isopropylidene-3-cyclohexanone Pulegone
1-Methyl-4-isopropylidene-1-cyclohexene Terpinolene
1-Methyl-4-isopropylidene-1-cyclohexen-3-one Piperitenone
2-Methyl-5-isopropylphenol Carvacrol
5-Methyl-2-isopropylphenol Thymol
Methyl4-methoxyphenyl ketone Acetanisole
7-Methyl-3-methylene-1,6-octadiene Myrcene
Methyl~-naphthylether ~-Naphthyl methyl ether
Methyl oxanone 4-(p- Methoxyphenyi)-2-butanone
Methylparaben Methyl p-hydroxybenzoate
Methyl parasept Methylp-hydroxybenzoate
3-Methyl-2-(2-pentenyi)-2-cyclopenten-1-one Jasmone
p- Methyl phenol p-Cresol
2-Methylphenyl acetate o-Tolyl acetate
Methylphenyl carbinyl esters a-Methylbenzyl esters
Methylphenyl ether Anisole
3-Methyl-3-phenyl-glycidic acid ethyl ester Ethyl methylphenylglycidate
Methyl phenyl glyoxal 1-Phenyl-1,2-propanedione
p-Methylphenyl esters p-Tolyl esters
2-Methylpropanal lsobutyraldehyde
2-Methyl-2-propen-1-yl butyrate 2-Methylallyl butyrate
Methyl propyl ketone 2-Pentanone
2-Methyl-1-propyl esters Isobutyl esters
Methyl protocatechuic aldehyde Vanillin
Methyl p-tolyl ether p- Methylanisole
Methyl2-pyridyl ketone 2-Acetylpyridine
Methyl pyromucate Methyl 2-furoate
Methyl styryl ketone 4-Phenyl-3-buten-2-one
Methyl succinate Dimethyl succinate
Methyl tetradecanoate Methyl myristate
5-(Methylthio)-2-(methylthio)methylpent-2-en-1-al 2,8-Dithianon-4-en-4-carboxaldehyde
a- Methyltolualdehyde 2-Phenylpropionaldehyde
Methyl a-toluate Methyl phenylacetate
Methyl p-tolyl carbinol p-a-Dimethylbenzyl alcohol
Methyl o-tolyl ether o-Methylanisole
Methyl p-tolyl ketone 4-Methylacetophenone
Methyl trisulfide Dimethyl trisulfide
Methyl undecyl ketone 2-Tridecanone
2-Methylvaleralehyde 2-Methylpentanal
5-Methyl-5-valerolactone 5- Hexalactone
Methylvanillin Veratraldehyde
2-(1-Methylvinyi) pyrazine Isopropenyl pyrazine
Morellone 3-Benzyl-4-heptanone
Muscolactone w- Pen tadecalactone
d,1-Muscone 3-Methyl-1-cyclopentadecanone
Mustard oil Allyl isothiocyanate
Myrtenal 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene
~-Naphthyl methyl ketone Methyl~-naphthylketone
Narcissin p-Tolyl phenylacetate
Neofolione Methyl2-nonenoate
Neral Citra!
'Y- Nonalactone Hydroxynonanoic acid, -y-lactone
Nonyl methyl ketone 2-Undecanone
Nootkatone 4,4a,5,6, 7,8-Hexahydro-6-ioopropenyl-4,4a -dimethyl-2
(3H)-ilaphthalenone
Octadecanoic acid Stearic acid
5-0ctanol-4-one 5-Hydroxy-4-octanone
-y-Octyl--y-butyrolactone -y-Dodecalactone
Octyl-crotonyl acetate 1,3-Nonanediol acetate
Oenanthal Heptanal
a-Oxodiphenylmethane Benzophenone
528 Source Book of Flavors

Synonym Refer to Chemical Listed in Main Tabular Body

3-0xo-1-octanol 3-0ctanon-1-ol
4-0xopentanoic acid Levulinic acid
1-0xo-phenylethane Phenylacetaldehyde
2-0xopropanal Pyruvaldehyde
2-0xopropane Acetone
1-0xy-2-methoxybenzene Guaiacol
Palatone Maltol
Palmityl alcohol 1-Hexadecanol
Peach aldehyde -y- U ndecalactone
Pelargonic acid Nonanoic acid
Pelargonic alcohol Nonyl alcohol
Pentanal Valeraldehyde
1-Pentanol Amyl alcohol
Pentyl alcohol Amyl alcohol
Pentyl esters Amyl esters
Perilla alcohol p-Mentha-1,8-dien-7-ol
Peruviol Nerolidol
Phenethyl3,3-dimethylacrylate Phenethyl senecioate
Phenethyl 3-methylcrotonate Phenethyl senecioate
Phenylethyl methyl ether Methyl phenethyl ether
Phenylacrolein Cinnamaldehyde
3-Phenylallyl esters Cinnamyl esters
Phenylamyl alcohol 5-Phenylpentanol
Phenyl benzene Biphenyl
2-Phenylcrotonaldehyde 2-Phenyl-2-butenal
2-Phenyl-m-dioxan-5-ol Benzaldehyde glyceryl acetal
2-Phenyl-1,3-dioxan-5-ol Benzaldehyde glyceryl acetal
Phenyldithiobenzene Phenyl disulfide
2-Phenylethyl esters Phenethyl esters
Phenyl ethyl ketone Propiophenone
Phenyl ketone Benzophenone
Phenylmethanethiol Benzyl mercaptan
Phenyl methyl ether Anisole
3-Phenyl-2-propen-1-al Cinnamaldehyde
3-Phenyl-2-rropen-1-yl esters Cinnamyl esters
2-Pinen-4-o Verbenol
Piperitol p-Menth-1-en-3-ol
Polyoxyethylene sorbitan esters Polysorbates
1,2-Propanediol Propylene glycol
Propanethiol Propyl mercaptan
1,2,3-Propane trio! Glycerol
2-Propen-1-yl esters Ally1esters
4-Propenylguaiacol iso- Eugenol
2-Propenyl esters Allyl esters
sec-Propyl alcohol Isopropyl alcohol
3-Propylallyl alcohol 2-Hex en -1-ol
Propyl trisulfide Dipropyl trisulfide
Protocatechualdehyde dimethyl ether Veratraldehyde
Protocatechualdehyde 3-methyl ether Vanillin
Protocatechualdehyde methylene ether Piperonal
Prunolide 1- Nonalactone
Pseudopinene {:1-Pinene
Pyrazinemethanethiol 2-Mercaptomethylpyrazine
Pyrocatechol monoethyl ether Guaiacol
Racemic acid Tartaric acid
Raldeine Methyl-a-ionone
Raspberry ketone methyl ether 4-(p-Methoxyphenyl)-2-butanone
Rhodinal Ci tronellal
Rosa! Phenylacetaldehyde dimethyl acetal
Rose oxide Tetrahydro-4-methyl-2-(2-methylpropen-1-yl)pyran
Sabinene hydrate 4-Thujanol
Safran a! 2,6,6-Trimethylcyclohexa -1 ,3-dienylmethanal
Senecioic acid 3-Methylcrotonic acid
Styralyl esters a-Methylbenzyl esters
Syringa aldehyde p-Tolyacetaldehyde
fu'riiwoi 2,6-Dimethoxyphenol
Terpmene Terpinolene
Terpineol 4-Carvomenthenol
Tetradecanal Myristaldehyde
Tetradecanoic acid Myristic acid
Tetrahydrocarvone p-Menthan-2-one
 Organic Chemicals Used in Flavorings and Fragrances 529

Synonym Refer to Chemical Listed in Main Tabular Body

Tetrahydrogeraniol 3, 7-Dimethyl-1-octanol
Tetrahydropyrrole Pyrrolidene
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten- a-lrone
2-one
THFA Tetrahydrofurfuryl alcohol
Thiobenzyl alcohol Benzyl mercaptan
Thioallyl ether Allyl sulfide
Tiglaldehyde 2-Methyl-2-butenal
a-Tolualdehyde Phenylacetaldehyde
a·Toluenthiol Benzyl mercaptan
o-Toluenthiol 2-Methylthiophenol
a-Toluic acid Phenylacetic acid
Tonkalide -y- Hexalactone
Triacetin (tri-)Acetin
4-(2,6,6-Trimethyl-2-cyclohexen-1-yll-3-buten-2-one a-lonone
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one I'Honone
1,3, 7 -Trimethyl-2,6-dioxopurine Caffeine
Tweens Polysorbates
li- Undecalactone 5-Hydroxyundecanoic acid lactone
Valera! Valeraldehyde
Validol Menthyl isovalerate
Vanillin methyl ether Veratraldehyde
Vanitrope Propenylguaethol
Vel to!- Plus Ethyl maltol
Vinyl amyl ketone 1-0cten-3-one
Vinylbenzene Styrene
Yarayara {3-Naphthyl methyl ether
TABLE 10-2.

Prefixes Chemical Formula Synonym(s)

Acetoacetyl- CHa·CO·CH2·CO-
Acetoxy- CH3·CO·O-
Acetyl- CHa·CO-
Acrylyl- CH2CH·CO-
Aldo- 0:
Allyl- CH2:CH·CH2- 2-Propenyl-
Vinyl carbinyl-
{3-Allyl- CH2:CH(CH3)- Isopropenyl-
Allyloxy- CH2:CH·CH2·0-
Amino- H2N-
Anisal- Anisalidene-
CHaO-o-CR:
Anisalidene- Anisal-
Anisyl- p·Methoxybenzyl-
CHaO - o - C H 2 -
Azo- -N:N-

Benzal-
Q-cH: Benzilidene-

Benzoxy-
o- CO·O-

Benzoyl-
Q-co-
Benzyl-
Q-cH2-
Benzylcarbinyl- Phenethyl-
Tolyl·
 530 Source Book of Flavors

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Benzilidene- C.Ha·CH: Benzal
Benzyloxy-
Q-cH~·o-
Benzylthio-
Q-cH,·S-

Bomyl-

Butoxy- CHa(CH,)aO-
Butyl- CHa(CHa)a-
sec-Butyl- C,H,·CH(CHz)-
tert-Butyl- (CH,>aC-
Caproyl- CHa\CH.).CO- Hexanoyl-
Capryl- CHa(CH,),CO- Octyl-
Carbonyl- OC:

-0-
Carboxy- HO·CO-

Carvacryl·
CHa)cH CHa
CHa

Cetyl- Hexadecyl-

Cinnamal- Q-cH:CH·CH: Cinnamylidene-

Cinnamyl-
Q-cH:CH·CH~-

OH-Q-~
Cresyl-

Crotonyl-

Cumyl-
CHa
CH/
\CH
-o-
CHa·CH:CH·CO-

Cyclobutyl CHI-CH-
I I
CH~--CH2

Cycloheptyl CH,(CHI)aCH-
1 I
Cyclohexyl- CH,(CH.).CH- Cyclohexanyl-
1 I Hexahydrophenyl-
Cyclopentyl- CH-
/""'-..CH,
CH2
I I
CH~---CH2
 Orgartic Chemicals Used in Flavorings and Fragrances 531

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Cyclopropyl-
_...................._
CH-
CHI CHI

2-p-Cymyl-
~-o-
CHa
)CH CHa Carvacryl-

Decyl- CHa(CH2)aCHa-

~0--o--CHr
Dimethoxyphenethyl-

CHaO

Dimethylbenzyl-
~--o-CH,-
CHa

Diphenylmethyl- (C.Ha)a·CH-
Dithio- -S:S-
Dodecyl- CHa(CH2)10CH2- Laury!-
Enanthyl- CHa(CH2)sCO-
Ethenyl- CH2:CH- Vinyl-
Ethynyl- CH..C-
Epoxy- -0-
Ethoxy- CHa·CH2·0-
Ethyl- CH:1·CH2-
Ethylene- -CH2:CH2-
Ethylidene- CHa·CH:
Ethylthio- CHa·CH2'S-
CHa
Fenchyl-

~~ CHa
Formyl- H·CO-

Furfural- Furfurylidene-
(JlcH:

Fururyl-
([JLcH.-

lVoo-
0

Furoyl-

Fury!-
~-
Geranyl-
CHa
>
~:rc CHa

CHa-
532 Source Book of Flavors

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Glyceryl-

Guaiacyl-

Heliotropyl·
o-- OCHa
o· Methoxyphenyl

rv-C~-
Piperonyl·

H2C--O
Hendecyl· CHa(CH2)uCH2- Undecyl·
Heptyl· CHa(CH2)aCH2-
Hexadecyl- CHI!.(CH2)14CH2- Cetyl·
Hexahydrophenyl· (seeJ Cyclohexyl-
Hexyl- CHa(CH2).CH2-
Hexylidene· CHa(CH2)4CH:
Hydratropyl· CHa 2· Phenylpropyl·
Q-6H·CH2-

Hydrocinnamyl· 3- Phenypropyl-
o-CH2·CH2·CH2-

Hydroxy· HO- Hydroxyl·

Hydroxy amino· HO·NH-
Hydroxyl· HO- Hydroxy·
o· Hydroxy benzyl· Salicyl·

Hydroxymethyl· Methylol·
Imino·
lsoallyl·
Isoamyl·
Isobornyl·

Isobutenyl· 2- Methylpropenyl-
Isobutoxy·
Isobutyl·
Isohexyl·
lsopentyl·
lsopropenyl·
Isopropyl·
ar·lsopropylbenzyl

Isovaleryl·
Keto-
Lauryl· Dodecyl·
 Organic Chemicals Used in Flavorings and Fragrances 533

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Linalyl-
CHr = ! : J < C H a
CHa CHz -

Menthyl-

~
CHa
CHa
Mercapto- HS- Thiohydroxy-

~-Q-
Mesityl-

CHa
Methallyl- CH2:C(CHs)·CHa-
Methionyl- CHa(~)z:
Methoxy- CHzO-
p-Methoxybenzyl- Anisyl-

CHsO-oCH2-

o-Methoxyphenyl-

q-- OCHa
Guaiacyl-

Methyl- CHa-
Methylbenzyl-
CHa--QcH~-
(o), (m) and (p)
Methylene- CHz:
Methylenedioxy- -O:CHz·O-
Methylol- (see) Hydroxymethyl-
2-Meth~ropenyl- (see) Isobutenyl-
Methyl furyl- CH,·SOz-

ro-
Methylthio- CH,·S-
Myristyl- CH,.(CH2)12·CHz_ Tetradecyl-
Naphthyl-

Neryl-
CH,~CHa
CHa C
-H2
Nitro- 02N-
Nitroso- ON-
Nonyl- CHa(CH2),-CHz- Pelargonyl-
Octyl- CHa(CHz)a·CH~- Capryl-
Oenanthyl- CHa(CH2la-CO- Heptyl-
Oxy- -0-
Pelargonyl- (see) Nonyl-
Pentadecyl- CHa(CH2),a·CHa-
Pentenyl- CH~CH 2 ·CH:CH·CH2 -
Pentyl- CHa(CHa>a·CH~-
534 Source Book of Flavors

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Phenethyl-

Phenoxy-

Phenyl-

Phenacetyl- a-Tolyl-
OcH.-co-

Phenallyl-
OcH.:CH·CH.-

Phenylpropyl- Hydroxycinnamyl-
Q-cHa·CHa·CH.-

Piperonyl- Heliotropyl-

r--9-~-
H.c--o
2-Propenyl- (see) Allyl-
Propinyl- CHa·CHa·CO-
Propyl- CHa·CH.·CH.-
sec-Propyl· (CHa)aCH-
Propylene- ·CH(CHa)·CH1-
Propylidene- CH3·CHa·CH:
Pyrazinyl-

Salicyl-

Styryl-
o-- OH
o-Hydroxy benzyl-

Cinnamenyl·

Q-cH:CH-

Succinyl· -CO·CH.·CHa·CO-
Sulfinyl- -so- Thionyl-
Myristyl-
Tetradecyl- <see>
Thienyl- c.HaS-
Thio- -8-
Thionyl- (see) Sulfinyl-
Thiohydroxy- (see) Mercapto-
Toloxy- (see) Cresoxy-
 Organic Chemicals Used in Flavorings and Fragrances 535

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
a-Toluyl- (see)
Benzt·
Phenylacetyl-
a-Tolyl- (see)
Undecyl- CHa(CHa),CHa- Hen ecyl-
Valeryl- CHa(CHa)a·CO-
Vanillal- CH: Vanillylidene-

Vanillyl-
~~ OH
CHz-

Vanillylidene- (see)
~~ OH
Vanilla!-
Veratryl- CHz-

~~ OCHa
Vinyl- CH~:CH- Ethanyl-
Vinyl carbinyl- (see Allyl-
Esten
Acetate CHa·COO- Ethanoate
Acetoacetate CHa·CO·CHz·COO- 3-0xobutanoate
o-~nobenzoate (see) Anthranilate
Anisate p-~ethoxybenzoate
COO-

¢ OCHa
Anthranilate a-Aminobenzoate

a~
Butanoate CHa(CHz)a·COO- Butyrate
Butyrate (see) Butanoate
Caprate (see) Decanoate
Caprinate (see) Decanoate
Caproate (see) Hexanoate

o-
Capronate (see) Hexanoate
Caprylate (see) Octanoate
Cinnamate Phenylpropenoate
CH:CH-cOO-
536 Source Book of Flavors

TABLE 10-2. Continued

Prefixes Chemical Formula Synonym(s)
Decanoate CHa( CHz)a·COO- Caprate, Caprinate, Decylate
Decenoate CHa(CHz)e·CH:CH·COO- Decylenate
Decylate (see) Decanoate
Decylenate (see) Decenoate
Dodecanoate CHa(CHz)to·COO- Dodecylate, laurate, laurinate
Dodecylate (see) Dodecanoate
Ethanoate (see) Acetate
Formate H·COO- Methanoate

Ol
Furoate 2-Furoate

0 COO-
Heptanoate CHa( CHz)aCOO- Heptoate, heptylate
Heptoate (see) Heptanoate
Heptylate (see) Heptanoate
Hendecanoate (see) Undecanoate
Hexanoate CHa( CHz).COO- Caproate, capronate, hexoate, hexylate
Hexenoate CHa(CHz)z·CH:CH·COO-

o-
Hexoate (see) Hexanoate
Hexylate (see) Hexanoate
Hydrocinnamate Phenylpropionate
CHz·CHz·COO-

o-Hydroxy benzoate (see) Salicylate

!sobutyrate (CHa)z·CH·COO- 2-Methyl propanoate
Isovalerate (CHa)z·CH·CH2·COO- 3-Methyl butanoate
Lactate CHa·CH(OH)·COO- a-Hydroxy propionate
Laurate (see) Dodecanoate
Laurinate (see) Dodecanoate
Methanoate (see) Formate
p- Hydroxy benzoate (see) Anisate
3-Methyl butanoate (see) Isovalerate
3-Methyl propionate (see) !sobutyrate
Myristate CHa(CHz)tzCOO- Tetradecanoate
Nonanoate CHa(CHz)7COO- Nonylate, pelaronate
Nonenoate CHa(CHz)a·CH:CH·COO-
Nonylate (see) Nonanoate
Nonynoate CHa<cH2)a·c-COO- Octyne carbonate
Octanoate CHa(CHz)e·COO- Caprylate, octylate, octoate
Octoate (see) Octanoate
Octylate (see) Octanoate
Octyne carbonate (see) Nonynoate
Octynoate CHa(CH2).·c-COO- Heptyne carbonate
Oxobutanoate (see) Acetoacetate
Pelargonate (see) Nonanoate
Pentanoate (see) Valerate
Phenylacetate a-Toluate

o-CHz·COO-

Phenylpropionate (see) Hydrocinnamate

Propanoate CHa·CH~·COO- Propionate
Propionate (see) Propanoate
Salicylate o- Hydroxy benzoate
OH

a~
Tetradecanoate (see) Myristate
Tetradecylate (see) Myristate
Thiobutyrate CHa( CHa)I·COS-
Tiglate 2-Methyl-2-butenoate
HaC
I
CHa·CH:C·COO-
 Organic Chemicals Used in Flavorings and Fragrances
TABLE 10-2. Continued
Prefixes Chemical Formula
a-Toluate (see)
Undecanoate CH3( CH~) 9 COO­
Undecenoate CH2:CH\CH2)sCOO-
Undecylate (see)
Undecylenate (see)
Valerate CHa( CH2)aCOO-
Valerianate (see)
Sources: The following sources of infor-
mation used in compiling the data given
below are gratefully acknowledged:
Arctander, S. 1969. Perfume and Flavor Chemi-
cals (Aroma chemicals), Vol. I and II. Mont-
clair, N.J.: Steffen Arctander.
C.F.R. 1990. Code of Federal Regulations.
Washington, D.C.: U.S. Government Print-
ing Office.
Council of Europe. 1981. Flavouring Substances
and Natural Sources of Flavourings, 3rd
Edition. (Maisonneuve S.A., Moulins-Les-
Metz, France), Strasbourg, France.
EOA. Updated to 1975. Specifications and Stan-
dards. New York: Essential Oil Association of
U.S.A.
Food Chemicals Codex, 3rd Edition. 1981.
Washington, D.C.: National Academy of
Sciences.
Ford, R.A. and Cramer, G.M. 1977. Reference
list of flavoring substances in use in the United
States. Perf. Flavor. 2(1):9-62.
Fries & Fries. 110 East 78th Street, Cincinnati,
Ohio, 45241.
Furia, T.E. and Bellanca, N. 1975. Fenaroli's
Handbook of Flavor Ingredients, 2nd Edition.
Cleveland: C.R.C. Press.
Grundschober, F., Hall, R.L., Stofberg, J., and
Vodoz, C.-A. 1975. Survey of worldwide use
levels of artificial flavouring substances. Int.
Flavours Food Additives. 6(4):273-230.
Hall, R.L. 1960; Hall, R.L. and Oser. B.L. 1961,
1965, 1970; Oser, B.L. and Hall, R.L. 1972,
1973; Oser, B.L. and Ford, R.A. 1975, 1977,
1979. Oser, B.L., Ford, R.A., and Bernard,
537
Synonym(s)
Phenylacetate
Undecylate
Undecylenate
Undecanoate
Undecenoate
Valerianate, pentanoate
Valerate
B.K. 1984, 1985. Burdock, G.A., Wagner,
B.M., Smith, R.L., Munro, I.C., and New-
berne, P.M. 1990. Recent progress in the con-
sideration of flavoring ingredients under the
Food Additives Amendment. Food Techno!.
14(10):488; 15(12):20; 19(2), Part 2, 151;
24(5):25; 26(5):35; 27(1):64; 27(11):56; 28(9):
76; 29(8):70; 31(1):65; 32(2):60; 33(7):65;
44(2):78.
Howard, P.H. and Neal, M.W. 1991. Dictionary
of Chemical Names and Synonyms. Boca
Raton, Fla.: CRC Press, Inc.
International Organization of the Flavor Indus-
try. 1978. Code of Practice for the Flavour
Industry 1978. List of artificial flavouring sub-
stances, as amended July 1990.
Lide, D.R. 1991. CRC Handbook of Chemistry
and Physics. Boca Raton, Fla.: CRC Press,
Inc.
MAFF. 1976. Report on the Review of Flavour-
ings in Food. Food Additives and Contami-
nants Committee. Ministry of Agriculture,
Fisheries and Food. U.K.H.M. Stationery
Office, London.
NOTE: Flavoring substances appearing
in the FEMA GRAS lists are sequentially
numbered as follows: GRAS 3, 2001-3124;
GRAS 4, 3125-3249; GRAS 5, 3250-3325;
GRAS 6, 3326-3390; GRAS 7, 3391-3423;
GRAS 8, 3424-3444; GRAS 9, 3445-3475;
GRAS 10, 3476-3525; GRAS 11, 3526-
3596; GRAS 12, 3597-3650; GRAS 13,
3651-3739; GRAS 14, 3740-3754; GRAS
15, 3755-3774.
 Chapter 11
Flavor Manufacturing
PART I
By Russ Shay

In time, there was a separation of the

INTRODUCTION
pharmaceutical phase from the flavor/aroma
The drug industry had, for a long time, area, since the skills of the quality control
processed botanicals for use as pharmaceuti- personnel were different and the flavor and
cals, and it is not surprising that the method- perfume industries gained recognition and
ology was transferred to the processing of their own viable markets. Synthetic organic
other botanicals for use in flavors and per- chemicals entered the field as the chemical
fumery (Dorland and Rogers 1977). In fact, processing industry grew, and many flavor-
processing of these materials antedated the ing ingredients were offshoots of the dye
industry as such, with monks infusing herbs industry arising from similar intermediate
to make specialty wines and liqueurs, and raw materials.
alchemists making "witch's brews" of many The larger flavor (and perfume) com-
sorts. As perfumers and flavorists became panies became self-sufficient in the produc-
more skilled in the art of selection of raw tion of virtually all ingredients used in the
materials, the quality of these materials flavoring, buying only raw materials that
became more uniform because manufac- were commodities rather than specialties
turers were forced to meet the competition. and selling per se only a few of the larger-
Not only were the organoleptic qualities volume items in their repertoire. Some
made more consistent within the output of a manufacturers had excess production and
given manufacturer, but the physical and economies of scale became apparent. Thus,
chemical properties were stabilized insofar smaller companies were able to purchase
as consistent with the analytical methods rather than manufacture all their ingre-
available at the time. With more sophisti- dients, and the variations among producers
cated analytical procedures evolving at a was highly noticeable. Those of better qual-
rapid pace, the quality and uniformity of the ity overcame the objections of purchasers of
flavor ingredients grew, with manufacturers poorer materials, albeit often at lower cost
learning how to adjust the results within for those items, and there arose an almost
specifications and customers likewise becom- unique situation wherein customer/com-
ing proficient in detecting ingredients petitor relations were such that one
not usually present in the product. compounder-manufacturer would buy from
538

and sell to another many raw materials.
Some specialties were retained for internal
use, not being sold at all, or at prices so
high that competitors would be at a great
economic disadvantage if they were to use
the item in a composition.
Some companies do not manufacture
any raw materials. Large suppliers of both
natural and synthetic chemicals have entered
the industry, bringing in materials from all
over the world at very competitive prices.
The standards of purity have grown tre-
mendously, with ultramodern analytical
techniques in regular use to supplement
organoleptic evaluation, which remains the
prime consideration. No matter how pure, if
the odor/flavor is different from that origi-
nally used in a composition, the purchaser
will refuse to substitute the ingredient with
another quality/source, even when a specific
natural is unavailable. For example, it is
with extreme reluctance that a substitute or
mixture of substitutes will be used to tide
over output. If changes in availability are
anticipated, changes in formulations are
made gradually. With chemicals of extreme
purity available, but with organoleptic char-
acteristics different from those of that
chemical made by other methods or from
traditional sources, the nuances are being
returned by the judicious addition of other
extremely pure ingredients.
While it behooves a purchaser to know as
much as possible about the methods used by
his suppliers, the secrecy or pseudo-secrecy
prevalent prevented this when the supplier
was also a competitor. It is only recently
that some producers of synthetic chemicals
have departed from the secret nature of the
business in that they patent ingredients for
use in specific types of flavors. The industry
has become multinational, in spite of the
difference in regulations for the use of both
natural and synthetic chemicals in flavors
among the nations of the world.
Whether or not the process is a trade
secret, patented, or of common knowledge,
it may be broken down into the unit opera-
tions used throughout the chemical and food
Flavor Manufacturing 539
industries. They are interrelated, a process
usually involving several steps (unit opera-
tions) that must flow smoothly from one
to the next to reproduce the end material
in proper quality and with an economical
yield. There are many textbooks to give the
details of each such operation to the satis-
faction of process engineers, and the meth-
odology is constantly being improved from
the viewpoints of quality, yield and ease of
handling. (Valentas, Levine and Clark 1991;
Fellows 1988; Brennan, Cowell and Lilley
1990; Earle 1983; Harper and Watson 1988;
Heldman and Singh 1981; Henderson and
Perry 1976).
It is valuable to read some of the reviews
appearing in older trade literature to com-
pare with the newest versions, remembering
that some changes are dictated by considera-
tions of environmental and personal health
protection, as well as for economic reasons.
Some of the discussions that follow may
therefore become obsolete. Before any new
construction or modification of a manufac-
turing plant is considered, it is imperative to
read the latest such reviews and to contact
manufacturers of the equipment described
therein.
With the above limitations in mind, the
following unit operations will be briefly dis-
cussed, some in more detail than others,
attempting to include as many variations as
possible even if every one available is not
mentioned. These should enable the reader
to become sufficiently versed in the general
techniques and with the terminology used to
take advantage of the latest advances in
technology. They will include:
Raw materials handling
Comminution, sieving, extraction with sol-
vents, pressing, distillation (direct, steam,
vacuum, azeotropic) and sterilization (gas,
radiation).
Liquid flavor production
Blending and compounding, clarification
(filtration, centrifugation), emulsification,
540 Source Book of Flavors
homogenization, pasteurization and pre-
servation.
Dry flavor production
Dehydration, adsorption, spray-drying,
microencapsulation, powder blending.
Packaging
Storage of flavoring materials and products.
RAW MATERIALS HANDLING
A. Comminution
While most of the following will deal with
natural aromatic materials (e.g., spices,
herbs, nuts, etc.), the methods discussed
may be used with individual solid chemicals
as well (Anon 1970c). The natural materials
come from the point of production in rela-
tively large pieces of the plant (perhaps even
the whole plant), packaged in fiber bags,
bales or boxes. The size of the plant parts
most often precludes their use directly in
foods or in the separation of ingredients
for use in flavors and, thus, must be com-
minuted (or ground) in order to be further
processed. Although comminution may fol-
low sterilization, discussion of that phase
will be treated later on; customs regulations
in many countries require that imported
plant materials be reasonably free from con-
tamination by vermin, etc., and it is as-
sumed that any materials to be processed
are so cleared.
Size reduction is an essential first stage
for extraction or distillation of ingredients,
for incorporation into food product mixes
or for use by themselves at table or in cook-
ing. Small particle size enables solvent or
steam to come into intimate contact with the
cellular tissues containing the desired
aromatic ingredient rapidly and efficiently.
Because so many different plants and por-
tions of plants are used, the materials to be
comminuted show a great variation in tex-
ture, friability, hardness, oiliness, stability,
size, etc., and in quantity to be handled.
All of these enter into determination of the
type of equipment needed to produce the
degree of comminution optimal to the next
stage of the process.
There are many different ways to cut,
grind, break or otherwise reduce size to the
parameters specifically desired, whether the
basic material is to be handled in kilos/
day or metric tons/hour (Anon 1970c). The
venerable mortar and pestle are used in the
laboratory; large plants are equipped with
automatic pneumatic or mechanical con-
veyors, recycling systems, dust collectors,
samplers and whatever else is needed to
handle the tonnage. In between are types of
machinery that fall roughly into the follow-
ing classes:
a. Coarse cutters, crushers or breakers
designed to give an intermediate
product further reduction from the
large plant parts received in bulk.
b. Slow-speed attrition mills, which
reduce the product to a fine powder.
c. High-speed impact mills, whereby a
wide range of sizes may be produced,
and throughput is rapid.
d. Micromills for extremely fine powders.
Very often a section of the processing
plant is reserved particularly for comminu-
tion, and the small particles thereafter trans-
ferred in batch cans, trucks, hoppers, etc.,
to the area of the building(s) in which further
processing is to take place. Large amounts
may be transferred pneumatically. This
permits more efficient dust removal and/or
collection as may be required for environ-
mental and health reasons.
Several types of dust collectors are avail-
able, including cyclone, bag and wet scrub-
bers. The latter generally are used not for
recovery of product, but to prevent harmful
or simply annoying particulates from being
discharged into the atmosphere.lt is possible
by judicious selection of the liquid phase to
use that phase in subsequent extraction of
the coarser material being comminuted for
extraction. Most often, water is used. Its
discharge is in turn regulated; particulates

may require removal before the water is dis-
charged to the sewer system.
Ball Mills
Material fed into ball mills is usually already
coarsely ground. A ball mill consists of a
cylindrical revolving chamber with balls of
varying size made from a variety of mate-
rials. The continuous impact and friction of
these balls rolling, rotating and dropping
upon the substrate reduces the particle size.
The final size depends not only on the size
and weight of the individual balls, but on the
speed and duration of rotation and the rela-
tionship of the balls to the friability of the
material being ground.
The chamber of the ball mill is typically
made of stainless steel, mild steel or ceramic
(as a lining only in larger sizes). The balls
similarly may be made of stainless or mild
steel, porcelain, granite or other suitable
material; metals are usually specially hard-
ened. Ball size will vary with the size of the
chamber also; they must be small enough to
ride easily over each other, but be heavy
enough to exert sufficient impact and grind-
ing ability. They should not occupy more
than 50 percent of the chamber volume in
order to allow production capacity, but will
vary with the material being ground. When
a very fine particulate is desired, rotation
should be slow and of long duration. This
will yield particles around 20 microns in size
as the balls tumble in a cascade manner.
When higher speeds are used, the balls fall
in a cataract manner and the resultant parti-
cles are in the range of 50-100 microns.
Rotational speeds may be varied in a given
process, starting relatively fast and slowing
as the run progresses.
Ball mills may be designed for continuous
operation with the exit port screened so that
only particles smaller than a specified size
will be discharged. The balls may even be
rods. Air may be used to remove the" par-
ticulates through a bag or cyclone collector.
They may also be jacketed to permit opera-
tion at reduced or elevated temperatures
and in the presence of water or other sol-
Flavor Manufacturing 541
vent. Good, uniform slurries and suspen-
sions may be produced.
End-Runner Mills
The standard laboratory mortar-and-pestle
is still being used for sample quantities
and test batches. It has been adapted to
larger-size mechanical versions in which a
weighted pestle is rotated eccentrically, with
the grinding head in a cup-shaped mortar
made of ceramic, metal or granite. Most
commonly the pestle is fixed and the mortar
is rotated, however, the pestle may rotate
on its own axis and rise or fall in its mount so
as to achieve good impact and sheer. A
scraper blade keeps the material in motion
back to the grinding area. Use of this type of
comminuter is limited to small batches of a
special nature.
Edge-Runner Mills
This type of mill is one of the oldest in use,
powered by water or animals and used for
grains. The material to be ground passes
continually between two grinding surfaces,
frequently two circular wheels rolling on a
flat circular bed of granite or other stone.
The rolling wheels are relatively thick and
move slowly, but they can be of metal.
Stones of several tons are not uncommon.
The action may be improved by rotating the
bed as well and two such machines may be
close-mounted so as to produce a mixing
action. While the product may be extremely
fine, the process is slow. An advantage is
that little heat is produced (absorbed by the
large mass of the surfaces also), but a dis-
advantage is the dust produced; equipment
now is enclosed when working.
The mulling process, as this is known,
has been adapted to the mixing and simul-
taneous size reduction of heat-sensitive
materials such as seasonings, spices, dry
mixes, etc. Here flavor and/or texture is of
prime concern, particularly when the ingre-
dients are of different particle sizes.
Modifications may be made for wet mulling,
continuous operations and so on. These
542 Source Book of Flavors
mills are usually of metal in sizes up to 500
gallons.
Disc Mills
As the name indicates, two circular grinding
surfaces are rotated countercurrently or one
remains fixed. They can be of metal, stone
or ceramic, and the mating surfaces are
usually grooved radially, helically or in a
special pattern. Mounting may be horizontal
or vertical and the relative speed of the discs
varied. The separation of the plates may be
adjusted by spring tension or through screw
mechanisms; closer tolerances produce finer
mesh product. Feed on vertical machines is
usually through a hopper, with flow rate
controlled by a damper or by additional feed
via a worm or screw. This lends itself to
continuous operation of a totally enclosed
machine. While the larger particles coming
out are those of the gap dimension, abrasion
results in many finer particles also and the
friction produces a large amount of heat,
being greater for smaller particles.
Roller Mills
Instead of discs, as discussed above, cylin-
drical rollers are used in a roller mill. The
rolls, in pairs, may turn in the opposite
direction at different speeds or at the same
speed, and the gap between the rollers is
adjustable by screws moving the mounting
bearings closer together or farther apart.
For maximum flexibility, two, three or four
sets of rollers may be mounted one above
another with the gaps of each pair being
independently controlled. The uppermost
has the widest gap and the size of the parti-
cles decreases as they drop by gravity to
the next lower pair. The pairs need not be
mounted vertically, but instead have a belt
or worm conveyor moving the mass to the
next stage or there may be a simple batch
system to convey the mass to another stage.
Roller mills are not effective in produc-
ing very fine powders, but are excellent for
grinding seeds with a high oil content, such
as coriander, dill, nutmeg, etc. They
normally do not produce much heat and
once the particles become smaller than the
set clearance, they remove themselves from
the active area. Aromatic spices destined
for distillation or extraction are often com-
minuted by this method. They have the
additional advantage of being relatively
inexpensive and easy to maintain.
Impact Mills-Disintegration
A feature common to most impact mills
is the high speed at which they operate,
4,000-6,000 rpm not being uncommon. This
normally means more difficult and frequent
maintenance of both the impact surface and
the bearings. Generally, the feed material
enters a chamber from the top at a con-
trolled rate and the product leaves at the
bottom through a screen. Those particles
that have not been sufficiently reduced in
size continue to be subjected to the im-
paction. The feed rate should not exceed
the exit rate or the chamber fills up, slow-
ing the mechanism and sometimes bringing
it to a complete stop, overloading the driv-
ing motor and/or its protective electrical
circuitry.
A set of rapidly rotating blades or ham-
mers or a combination of the two are in the
impact chamber. Some models are made
with sharpened edges on one side and flat
edges on the other and the entire chamber/
blade assembly may be reversed to use
either configuration, depending on the sub-
strate. Spacing between the blades is usually
fixed, but some allow the removal of a por-
tion of the multiple sets in the unit. In lieu of
swinging hammers/blades, a set of discs with
fixed pegs or studs may be used and the pegs
themselves may be of different shapes.
It is the impact of the moving mechanism
on the substrate that shatters or cuts it, and
the shear between them and the walls of the
chamber that in turn may become ridged or
grooved. The number and size of the active
impaction members are usually configured
for the particular product to be milled.
However, these machines can be very ver-
satile with easy replacement of one size
screen with another, with speeds adjustable
by changing pulley ratios on belt-driven
models, or by electronic or hydraulic speed

changers. The screens themselves may be
perforated with round holes, rectangular
slots or wire mesh. Screen mesh size deter-
mines the size of the ground material and
smaller screen sizes usually require a lower
feed rate. By carefully selecting the proper
combination of speed, mesh and hammer
type, a narrow range of particle size may be
achieved.
Where discs are used (pin mills), hard-
ened steel or alloy pins are placed in concen-
tric rings and the spacing may be selected
for the specific product. The discs may also
rotate in opposite directions or be a com-
bination of fixed and rotating plates, each
with pins. The feed is by gravity at the
top center and moves by centrifugal force
against the pins. As it passes toward the
periphery, it is impacted countless times by
moving or fixed pins, thus being reduced to
a fine powder. Pin mills are often used for
the comminution of low-melting materials.
Such high-speed disintegration mills are
used extensively for the preparation of
fibrous aromatic plant materials for extrac-
tion or distillation. There may be more of
them used than the total of all other types of
comminuting machines combined, not that
they are without drawbacks. Considerable
air flow is involved as well as heat generated
in the grinding chamber, so there may be
degradation of color and loss of valuable
volatile ingredients and/or moisture. While
it is possible to offset the heat by including
with the feed of the substrate a material
such as dry ice (solid carbon dioxide), this
is not necessarily economical. There are
several patented and proprietary machines
for the refrigerated and cryogenic milling
of spices now available, which seem to im-
prove the yield, yet retain the desired color
and aroma of the essential oils, oleoresins or
the spice itself (Lissack 1976; Pesek, Wilson
and Hammond 1985; Russo 1976).
Pulping
For particular purposes, such as the com-
minuting of fruits for use in ice cream,
fillings, jams, yogurt and so on, the com-
minution method of choice is pulping. Food
Flavor Manufacturing 543
materials of defined size and shape are con-
verted into a soft formless mass, which is
semi-fluid. Machine models are available in
all sizes, from a mill commonly employed
only in household kitchens to continuous
units capable of handling tons/hour. The
basic mechanism is a set of paddles that
break the fruit, and paddles and brushes
that force the fruit against a screen of the
desired mesh size, usually in a horizontal
cylinder. The screen must be of reinforced
construction and adequately supported. In
continuous units, as the fruit is fed into one
end, the coaxially turning brushes or a screw
forces the fruit against the sieve and the fine
slurry comes through. Pieces of pulp, rind,
peel and seeds continue to move on the
inside of the cylinder and are discharged at
the other end. Sometimes this rejected mass
is put through a second time to increase the
yield of desired product. In batch units, the
undesired mass is simply dumped out when
no more slurry comes through.
Micromills
There are two types of machines use to
produce particles in the micron and sub-
micron range. These are colloid mills and
micronizers.
Colloid Mills
These mills are specifically designed to
make suspensions of solids or immiscible
liquids in a continuous liquid phase. To
make a stable emulsion, the particles must
be extremely fine and uniform in size. The
mill operates by forcing the material
through a small passage between a rapidly
moving rotor and a fixed stator. Common
construction uses a truncated smooth cone
rotor revolving in a stator machined to very
close tolerances so the surfaces are parallel
with the clearance adjustable, for example,
between 0.001 and 0.05 inches, depending
on the product and the liquid phase.
Proprietary and patented designs exist in
which the stator and/or the rotor are per-
forated, machined with particular configura-
tions, or where the flow is countercurrent to
the centrifugal force to give a longer resi-
544 Source Book of Flavors
dence time in the active area. Claims are
made that this reduces required external
energy by reducing frictional losses.
Micronizers
This name identifies a class of mills in which
jet or fluid energy such as produced by a
high-velocity gas stream causes mutual
impact and shear by one particle upon
another. The particles coming out of this
device are in the range of 0.25 to 1.0 micron.
The relatively coarse feed (already pulver-
ized by other methods) is fed into a cylindri-
cal or specially shaped chamber constructed
of suitable stainless steel or other alloy and
high-pressure gas (air, steam, nitrogen or
carbon dioxide) is injected through suitable
nozzle ports to cause the mass to circulate at
high speed. The resulting violent motion
causes particles to hit one another, shatter-
ing them further. If the inlet feed rate is
adjusted to match the outflow with a given
residence time, particle size distribution
may be selected within reasonably narrow
ranges in a continuous unit.
Particle Size Selection
Although comminution can be an end in
itself, as when the substrate is to be sold per
se, as often as not, it is a step in a process
continuing in other equipment. It may be
taken for granted without regard to how it
may affect the subsequent stages. In a well-
designed process, the type of particle and
the method of achieving that particle is
thoroughly investigated; the yield and qual-
ity are often adversely affected if inadequate
care is taken in this early step. Particle size
and size distribution are important. The
type of mill used changes the shape of the
particle; the material of construction may
introduce impurities. Among the undesir-
able qualities are aggregation, lumping,
overheating, pasty masses, loss of volatiles
and the mechanical problems of screen
blinding, jamming, overloading, etc. Milling
is a much more important step than is some-
times considered; it is a specialized opera-
tion, whether it involves laboratory sample
preparation or tonnage bulk handling like
wheat for flour and corn for fermentation.
Environmental and health concerns have
become significant in recent times. Milling
is a dusty operation; dust explosions have
taken many lives in the past and the chronic
problem of breathing dust is of additional
concern. Where toxic hazards do not exist,
there is always a problem of irritation and
discomfort. At the same time, it is impor-
tant to remember the possible degradation
of the milled material; it should be handled
in a manner to reduce exposure to air, to
prevent spontaneous combustion, exposure
to contaminating odors and particulate
matter, and so on.
Since many of the plant materials have
come from foreign sources where handling
practices may be poorly controlled, it is
not only desirable but necessary to examine
those materials before feeding them into the
mill. Foreign objects may include stones,
rocks, nails to ax heads, scoops and trowels.
Coarse screens should be supplemented by
electromagnetic fields and metal-detecting
(for nonmagnetic but metallic objects)
devices. Damage could result to the prod-
uct, to personnel, to the equipment; sparks
could cause a dust explosion as well.
Sieving and Sifting
The product of comminution by whatever
means generally results in a powder with a
range of particle sizes, the largest and small-
est depending on the method used as well as
the specifics of the operation: feed rate, mill
speed, nature of the plant material, clear-
ance settings, etc. While such a range may
be acceptable for some purposes, it is fre-
quently important that the maximum and
minimum sizes fall within a narrow range.
To determine that range, a sample is put
through a set of standard sieves mounted in
a rotating or oscillating shaker with a tap-
ping device and the proportion that goes
through each sieve and/or remains on each
is noted. These sieves are made of woven
 Flavor Manufacturing 545

wire, each size having a given number of Production-sized machines have circular
holes per linear inch. The wires themselves or rectangular screens fitted into frames
are of specified diameter and the woven that are vibrated and/or rotated. The finer-
mesh fitted into a cylinder a few inches long. meshed screens may have backing support
Units are available in brass or stainless steel. grids of a larger mesh, so as not to impede
The sets have defined mesh sizes standard- passage. Oversized material may be re-
ized by a number of different agencies and moved continuously from any of the several
unfortunately have significantly different decks of frames that may be employed, so
apertures, so it is important to know which suitable particles of different ranges can be
standard has been used and to specify the selected for a specific end use, which may be
standard when comparing results. just for additional comminution. The loca-
For example, a powder may be said to tion of the sieving device is quite variable
pass 100 percent through a U.S.20 and 90.0 from free-standing, movable units for batch
percent retained on a U.S.lOO. It is a coin- or continuous use; some are fixed parts of
cidence that these sizes also have the same the milling machine itself. Screens may be
mesh designation in the Tyler series; there silk or other cloth, stainless steel, brass or
are tables showing equivalencies in many special alloy, with frames running a similar
reference books (e.g., Hayes 1987). The gamut from wood (older models commonly)
specifications are defined in the United to alloys. Stainless steel is almost a stand-
States under ASTM E 11-61, USA Standard ard. All of them share the lack of method-
Z 23-1, AASHO M92 and Federal Specifica- ology to force particles through a given
tion RR-S-3666; in the United Kingdom, screen, but at the same time they facilitate
refer to British Standard BS 410; in Europe, movement of the oversized away from the
the German DIN standards are widely used. system. Vibration and/or rotational rates
International (ISO) standards have been are often adjustable, and the feed rate is
proposed that correspond to some of the almost always so that as much of the fine
U.S. size numbers. Sizes for pharmaceuti- particles sift through as possible on one pass
cal powders are given in the appropriate and do not come off as oversized. It is
national pharmacopeia. A value called the important to size the machines with as much
"uniformity coefficient" is obtained by area as needed considering the desired flow
dividing the sieve opening (in millimeters), rate, to avoid blinding and buildup of fine
which will pass 60 percent of the sample by particles, which could unnecessarily become
the sieve opening (in millimeters), which part of the oversize particles being rejected;
will just pass 10 percent of the sample. a second pass might be needed if the area is
Some of the standards and their dates are too small.
listed below. It would be appropriate to Caking on the screens-"blinding"-
check with suppliers of sieves for analyti- that prevents proper passage is enough of a
cal purposes to ascertain which standard problem so manufacturers provide one or
applies. more methods to alleviate it, e.g., upward
air jets, turbine beaters, rotating brushes,
International ISO/R 565 (1972) electromagnetic or hydraulic vibrators or
ISO/R 2194 (1972) chains (appropriate material of construc-
ISO/R 3310, Parts I and tion). Single-stage batch units often rely on
II (1975) the operator to use a brush by hand! What-
British BSI 410/1969 (revised ever method is used, there should be no
1976) forcing of the particles through the screen or
German DIN 4187 (1974) mechanical distortion of the weave to create
United States ANSIIASTM Ell-70 larger apertures.
(reapproved 1977) Very fine powder production requires
546 Source Book of Flavors
special equipment to sort and collect the
particulate. There are air flow units with
high-speed centrifugal separators that de-
pend on the different rates of sedimentation
of the various sizes to group them together
in exit cyclones, or on spinning discs or
blades to set up the annular rings of parti-
cles. These are more used in the pharmaceu-
tical industry than in the flavor trade.
While the sieving unit operation may
separate particles into different size frac-
tions, within each fraction there may be
variations in chemical and flavor properties,
such as amount of fixed oil, essential oil, etc.
It is a common practice to reblend/mix each
individual group to ensure uniformity in the
end product.
Extraction
One of the most common operations in
the flavor industry is extraction. Natural
products, plant or animal, generally contain
a small proportion of aromatic constituents
in a very large amount of inert (flavor-wise)
matter. In plants, cellulose is the major
diluent making up cell walls that enclose the
desired flavoring chemical(s). Dehydrated
plant material may be more or less finely
ground and used directly in foods, e.g.,
herbs, spices and seasonings. However, the
flavorist finds it advantageous and often
necessary to have the flavorants in a more
concentrated form for the manufacturing
of favors (Langenau 1959; Stein 1977;
Guenther 1948-52). To that end, the
plant raw material (or a partially processed
natural material) is treated (extracted) with
a suitable solvent, or mixture of solvents, to
yield the optimum (not always maximum)
quantity of desired extractives.
The selection of solvent is limited by
toxicity, whether or not it is to be in the final
product (Mellan 1977; Pendleton 1970).
Therefore, the use of solvents permitted by
the authorities as acceptable food additives
is mandatory. While approved solvents vary
by country, ethyl alcohol is still universally
accepted as a solvent from a toxicity point
of view. However, cultural, religious or
ethnic objections may prohibit its use where
the imbibing of alcohol is taboo. Certain
sources of alcohol may not follow the
Hebraic rules of Kashruth, synthetic grades
being favored over grain sources, at least for
the Passover holiday. Many extractions are
made with ethyl alcohol and then diluted
with water to the optimum strength for the
particular product.
While this is the most common form of
extraction, there are other forms that are
used (Anon 1989b; Houser, Biftu and Hsie
1975; Peterson 1986). Separation of some
components from others may also be con-
sidered extraction. The pressing of sugar
cane and fruit for juice are, in effect, a form
of extraction separating the flavor ingre-
dients (or many of them) from the cellulosic
structure. If steam is used to distill volatile
materials from the rest of the plant, this
too may be considered an extraction; even
direct dry distillation may be considered by
some to fall within the definition of extrac-
tion. In other industries, the term may have
different meanings, such as the yield of flour
from wheat (as a percentage) being the
"extraction rate". Of great importance to
the flavor industry is the cold pressing of
citrus fruit to yield both juice and peel oil
(Guenther 1948-52) The description of this
process is beyond the scope of this chapter
covering a different industry, although some
firms may be subsidiaries of flavor industry
organizations.
Extraction of Plant Materials
Factors to consider in processing plant ma-
terial as the substrate for extraction include
not only the nature of the plant itself but the
characteristics of the desired extractive(s);
there is always more than one chemical
identity that is separated by the extraction
method adopted. Many variables must be
taken into account in the design of the pro-
cessing plant, its operation and the handling
of the product(s). These variables include:

1. Nature of the raw material
-Size
-Hardness (ease of comminution)
-Moisture content
-Fat content (fixed oils)
-Content of volatile components
-Pre-extraction stability and handling
-Storage characteristics: susceptibility
to deterioration
2. Nature of the volatile constituents
-Solubility in polar solvents
-Solubility in nonpolar solvents
-Thermal stability (physical stability)
-Chemical stability
-Hazards: physiological (toxicity), en-
vironmental
3. Nature of the solvent system
-Polar
-Nonpolar
-Environmental: halogenated
-Flammability and fire hazard
-Toxicity: physiological hazards
-Explosive characteristics
-Ease of recovery and/or removal from
extract
-Acceptance as food additive (locality
for end product use)
-Cost
-Regulatory problems
4. Nature of the extraction plant
-Material of construction
-Operation: batch, battery, or con-
tinuous
-Source and nature of heat and/or
cooling
-Rate of throughput
-Loading and unloading of plant mate-
rial and solvent(s)
-Disposal of by-products: marc, waste
water, spent fuel
-Quality control; sampling
5. Nature of end product
-Physical characteristics
-Solvent in end product
-Solvent stripping and recovery; level
permitted
-Packaging and storage
-Quality assurance
Flavor Manufacturing 547
Specific raw materials may have addi-
tional problems demanding attention and
resolution, not the least of which may be
regulatory, seasonality, availability of the
species/subspecies for which designed, po-
litical and economic conditions in the source
locality. The process flow sheet will show a
variety of individual details, yet fall within
the broad basic scheme. The precise operat-
ing conditions and the plant employed de-
pend on the quantity and quality of the
material to be extracted, the nature of
the solvent chosen (chemical and physical
criteria, such as boiling point being low or
high) and to what extent the solvent is to
be removed. As noted earlier, even with
a given raw material and primary solvent,
there are variations among manufacturers in
details.
A basic flow sheet for a solvent extrac-
tion process will include the following unit
operations:
a. Preparation by comminution.
b. Exposure to solvent.
c. Separation of the solute (micella or
menstruum) from the solid extracted
raw material (marc).
d. Separation of the solvent from the
solute to the extent required.
e. Recovery of residual solvent from the
marc.
f. Disposal of the marc (extracted plant
material) and other wastes.
This scheme does not differ substantially
from the manufacture of essential oils where-
in the solvent is stripped and possibly re-
placed by other solvents to standardize the
strength (Goldman 1949; Chodroff 1979).
There are only small modifications to permit
the production of liquid extracts, essences
and tinctures from botanicals.
Comminution (a) has already been dis-
cussed. There are three methods used for
(b), exposure to the solvent: maceration,
digestion, percolation and combinations of
these.
548 Source Book of Flavors

Maceration
Historically, this process involved putting
the botanicals into a cloth bag which, in
turn, was put into a larger closed container
(Anon 1970a). Sufficient room for expan-
sion of the botanical was required, as it
swelled when it got wet. The solvent used
has been aqueous ethanol, of a concentra-
tion between 40-60 percent B.V. (by
volume). The batch was allowed to stand,
usually at room temperature, with once
or twice daily agitation of the herbs and
menstruum until the solvent was saturated
(five to eight days or more). The extract
was drawn off and the botanical in the bag
pressed to recover additional material,
which was combined with the drawn-off
extract. The pressed herb was mixed with
water, typically of equal weight, and pressed
again. The pressings were added to the
liquid already obtained. The combined
liquids were allowed to stand to clarify and
be filtered, if needed, resulting in a product
containing about 30 percent alcohol B. V.
Some of the constituents of the botanical
are water soluble, such as sugars, resins,
tannic acid and bitter principles, while FIGURE 11-1. Equipment for the extraction and
concentration of oleoresins. (Courtesy ofT. Hasagawa
others such as the aromatic components and Co., Ltd.)
essential oils are alcohol soluble and are
dissolved by that portion of the menstruum.
The final product had a well-balanced By this method, extraction is usually com-
aroma and taste. When maceration is used plete in 24 hours, so it may be used when
today, the same scheme is followed, but the there are urgent demands for a particular
physical equipment has been updated to use flavoring extract. This process is also more
stainless-steel containers, hydraulic presses, efficient, yielding a better extract (better by
etc. virtue of higher yield or lower cost, albeit of
different quality). Generally, the quality is
Digestion poorer since the heat may cause sensitive
When heat is used to accelerate the extrac- ingredients to deteriorate or top notes to be
tion process, it is called digestion. The lost due to evaporation.
menstruum and botanical is kept at about
60°C (140°F) in a jacketed (or coiled) tightly Percolation
closed digester capable of withstanding pres- Percolation, which involves the recirculation
sure, or in a vessel equipped with a reflux of extraction solvent through a bed of plant
condenser to minimize loss of solvent. Heat- material, is probably the most widely used
ing is by circulating hot water or direct ap- method of extraction today as it is most eco-
plication of steam in the coil or jacket of the nomical in terms of labor and time. While
digester. Otherwise, handling is much the it takes three to five days to separate all
same as in the slower maceration technique. the flavoring components from the botanical

without loss of aroma and taste, it avoids the
need for labor to press the exhausted marc
and relatively little attention is required dur-
ing the extraction period. The equipment is
very flexible for easy changes from one bo-
tanical to another, or for a change in solvent
dilution or solvent per se. There are still,
however, many variations in the method of
charging the botanical and removing the
spent marc from the percolator. Within a
given processing plant, several types may
be used, depending on their age, size, fre-
quency of product changes, demands of the
marketplace, etc.
A menstruum containing 40 percent to 50
percent ethanol B.V. usually is sufficient for
the percolation, but 60 percent to 90 percent
is used in specific cases. Older vessels are
inverted cone-shaped, with a stainless-steel
perforated plate 4 to 10 inches above the
bottom outlet. Very old vessels are tin-lined
copper with copper or brass plates! More
modern units of larger capacity are cylin-
drical with perforated circular or specially
slotted grates, and have side manholes just
above the level of the plate with expandable
retaining rings to hold a sheet of cloth or
woven wire in place above and in contact
with the support plate. In the cone-shaped
devices, the botanical may be put into cloth
bags or directly on the plate, tamped into
place and covered by another heavier plate.
Care must be taken to allow for swelling
when wet and for eventual shrinking of the
bag when it is washed in the future, and
prewetting of the botanical may be invoked.
All this is avoided in the newer cylindrical
equipment.
The solvent is added and the mass al-
lowed to stand for a predetermined time,
e.g., 3 days, to soften the plant cells, allow
solvent penetration and for extraction of
the aromatic substances. On the fourth day,
true percolation is started wherein new sol-
vent is added to the top while menstruum is
withdrawn at the bottom at the same rate,
maintaining the level in the percolator con-
stant. About 10 percent of the menstruum
present is withdrawn per hour; the exact
Flavor Manufacturing 549
rate depends on the size of the percolator.
When the original volume of menstruum has
been withdrawn, feed of new solvent is
stopped, but the remaining menstruum in
the percolator continues to be withdrawn
until the rate becomes virtually nil. The
volume of percolate recovered is much less
than the volume of solvent originally used.
After closing the drain, the percolator is
filled with water to above the level of the
botanical.
After standing an additional 24 hours, or
at least overnight, the drain is opened as
before with the volume withdrawn being
replaced by water added to the top at the
same rate. This extract is added to the first
extract until the volume is equal to that
of the solvent originally used in the per-
colation. A modification called "Reserve
Percolation" may be used to give a more
concentrated extract. The initial withdrawal
of extract is stopped when about three-
quarters of the expected yield has been
obtained, and this is set aside or "reserved"
before withdrawal is continued. The last
portions being withdrawn are now concen-
trated under vacuum to a syrup that is then
added back to the reserved portion; this is
then adjusted with solvent to the desired
value. Thus, the major portion of the ex-
tract has not been subjected to heat and
possible (probable!) degradation, retaining
a better aromatic quality, yet removing all
the solvent from the botanical.
When small cone-shaped units are used,
they may simply be inverted to discharge
the bags or bulk botanical. Cones are often
mounted on pivots so that the inversion may
be helped by block and tackle or chain hoist,
and the marc heated if necessary with water
in a still to recover the last vestiges of sol-
vent ... this becomes an economical rather
than technical decision. In larger units, they
may be equipped with condensers, water
added to the marc, or steam admitted
through the bottom, to distill out the traces
of solvent. The manhole is opened and the
marc shoveled into carts or into screw con-
veyors for ultimate disposal.
550 Source Book of Flavors
While it may not fit exactly into the
definition of percolation, the process has
been modified to the following technology
for larger-scale commercial production. The
botanical is loaded through a top manhole
into the cylindrical, closeable vessel, having
been moved from the milling unit operation
by conveyor, hopper, batch can, etc. Above
the bottom perforated plate there has been
fitted a cloth or fine-mesh woven wire screen
and the manhole closed. A layer of inert
(flavor free) coarse material, such as straw
or rice hulls, may be used above it as a filter
aid. The solvent is introduced and circulated
by pumping, if desired, or just allowed to
stand at least overnight. A heat exchanger
may be inserted into the circulation system
to heat or cool to a standardized tempera-
ture. At the appropriate time, the men-
struum is drawn off as fast as it may happen
to run. When the rate slows down to a
trickle, the drain valve is closed and fresh
menstruum is added, circulation started
again, and the step repeated. The first and
second extracts are usually combined. Once
more, a third extraction is made. The con-
centration of the desired extractables in this
is most often minimal; therefore, it is not
added to the first two extracts, but is re-
tained to be used as the first menstruum in a
subsequent batch of the product. This mini-
mizes the use of fresh solvent for economic
reasons. Water or direct steam is used to
distill any remaining solvent from the marc;
it may then be fractionated under atmos-
pheric pressure for economic reuse of the
solvent. The marc is then discarded in an
environmentally acceptable manner. The
solvent may be totally evaporated from the
extract to produce an oleoresin, depending
on the botanical used, or a solid extract. The
solvent may be partially evaporated and/or
replaced by another solvent to produce a
fluid extract, often standardized to con-
tain the extractives of four or five times its
weight of the original botanical.
Further modifications may be made for
specific products, such as vanilla extract. In
the United States, by definition of the FDA
(Food and Drug Administration), vanilla
extract must contain the extractives of (at
least) 13.35 ounces of vanilla beans (of not
more than 25 percent moisture content) per
gallon of extract of 35 percent B. V. alcohol
(CFR). The coarsely chopped beans are
placed in stainless-steel trays and a number
of trays stacked and fitted closely to the
walls (to prevent bypassing) in a cylindrical
closed vessel. The solvent is then circulated,
often with mild heat, until saturated. It is
then drawn off. An additional extraction
may be made. The semi-exhausted beans
may then be pressed and the pressings
added to the extract. The strength of the
solution would then be adjusted to the re-
quired value and volume. Pursuant to regu-
lations, it is required in some localities that
the beans be destroyed following extraction.
Elsewhere, the beans may be re-extracted
again by the same or other solvents for the
production of vanilla formulations other
than that defined. If additional beans are
used in the first extraction, multifold
extracts may be produced, depending on the
quantity of beans used.
Unprocessed (other than comminuted)
botanicals are not the only raw materials
that may be used. For example, cocoa
powder made from cocoa nibs that have
been pressed to remove the cocoa butter
may be extracted in a similar manner, but is
often admixed with a filtering aid and placed
into small bags before being loaded into the
vessel. The filtering aid helps to improve
circulation and intimate contact with the
substrate.
There is a well-known laboratory method
of Soxhlet extraction wherein fresh solvent
is distilled and condensed, so as to fill a
porous cup or thimble containing the sub-
strate to a level that causes the liquid to
overflow through a siphon back to the still
pot. The solvent is boiled and the extraction
continued repeatedly until the substrate is
exhausted. Excess solvent must be used and
the extracted material is subjected to heat-
ing for a long period of time, not the best
way to keep quality high. Large apparati

FIGURE 11-2. Apparatus for the extraction of
cocoa. (Courtesy of Sanofi Bioingredients, Inc.)
have been used in the same manner or
vented so as to overflow continuously with-
out siphoning.
While the foregoing has described the
preparation of extracts to be used per se
primarily, it has been mentioned only in
passing that the solvent indeed may be re-
moved completely under controlled condi-
tions of heat, partial or full vacuum, under
inert gas, etc., and/or be replaced by higher
boiling solvent as in the production of solid
extracts, oleoresins and concentrates such as
fluid extracts. The added steps are those of
filtration (if needed) and distillation. If the
solvent first used is other than ethyl alcohol,
spraying with ethanol may be required to
reduce the trace amounts of the alternate
solvent to acceptable levels. Certain other
solvents are acceptable as GRAS (Gener-
ally Recognized As Safe) flavor ingredients
at reasonable levels, including acetone and
isopropanol. Although not used as extrac-
tion solvents, propylene glycol and glycerine
are often used to reduce the viscosity of the
concentrate and may be added before re-
moval of the solvent is complete.
Mention must be made of other solvents
being used in specialized equipment. Liquid
carbon dioxide and liquid sulfur dioxide,
under pressure to keep them in liquid
form, are now being used to extract coffee,
tea and numerous botanicals (Schneider,
Flavor Manufacturing 551
Stahl and Wilke 1980; Krukonis 1985;
Krishnaswamy 1974; Flament, Chevallier
and Keller 1987; Hubert and Vitzthum
1978). Exact configurations are proprietary.
Various fluorochlorohydrocarbons (which
may be gases or liquids at room tempera-
ture and which must be completely removed
from the end product) may be used as sol-
vents more for perfume materials than
flavorants. There are environmental con-
siderations also that proscribe their use.
Solvents such as hexane have similar prob-
lems and are disappearing from use if they
have not already done so.
Selected Solvent Extraction
Liquid/liquid selective solvent extraction is
normally a primary step in flavor ingredient
manufacture . It is used on flavorants that
have already been extracted from the plant
material by pressing, pulping, steam distilla-
tion or other solvent extraction. The main
uses are for deterpenation citrus or other
essential oils (e .g., peppermint or spear-
mint), for producing a soluble flavorant to
be used in clear beverages or for the re-
covery of certain ingredients from the
primary extracts of the plant materials. The
method depends on the selective distribu-
tion of solutes in immiscible solvents accord-
ing to well-defined principles of chemistry
and chemical engineering, viz., the Partition
Law, the relative concentration in each sol-
vent defining the distribution coefficient.
The reader is referred to standard textbooks
of physical chemistry and chemical engi-
neering for a more detailed discussion
(Earle 1983; Hall, Farral and Rippen 1986;
Weast 1990; Brennan et al. 1990). It suffices
to say here that single-stage and multistage
continuous units are commercially available
from a number of sources in a wide range of
sizes and hourly capacities. The value of the
distribution coefficient, K, is roughly equal
to the relative saturated solubility of the
substance in each of the solvents, at any
given temperature. Since solubility varies
with temperature, it is often possible to
make a separation at a temperature dif-
552 Source Book of Flavors
ferent from ambient when it is not feasible
at room temperature. When trade secrets or
patents are not at stake, the laboratories of
the equipment manufacturers can be a great
help in solving problems.
Production of Soluble Essences
The removal of terpenes and sesquiterpenes
from essential oils has traditionally been
done through one form or another of dis-
tillation. The fractionation under vacuum
required more sophisticated and costly
equipment than azeotropic or co-distillation
under atmospheric pressure. In either case,
the purpose was and remains to improve the
solubility in dilute alcohol (and possibly in
other solvents such as propylene glycol and
sugar solutions), increase the flavor strength
by concentrating the oxygenated chemicals
that contribute largely to the flavor and
improve oxidative stability by removing the
unstable terpenes. Exposure to heat does
bring with it some degradation and altera-
tion of the flavor profile, and alternative
methods were eventually developed. One
such method involves the selective adsorp-
tion of the desirable oxygenated constit-
uents on silica gel in a column, whereas the
hydrocarbon terpenoids pass on through.
The desired ingredients are then eluted in
ethanol or other solvent, eventually to be
replaced by diluted ethanol. Another
method is to use a large quantity, 15-20
times by volume of the whole or partially
deterpenated oil of diluted, say 60 percent
B. V., ethanol. The mixture is stirred well,
often forming an unstable emulsion, and
then it is allowed to settle and separate. The
terpenes float to the top, where they may be
separated by conventional means, including
solid-bowl centrifugation (just as cream is
separated from milk), decantation, skim-
ming or large-scale separatory funnels. If
the emulsion does not break within a few
days, centrifugation is the method of choice.
While this type of operation was once
carried out in large ceramic vats, stainless-
steel tanks are now more common with
tapered, slope or cone bottoms to ease the
separation physically. A variation of the
method dissolves the oil in 95 percent
ethanol, the 190 proof grade of commerce,
followed by gradual addition with stirring of
sufficient water to reduce the strength to
that desired to affect the separation. The
separated terpene fraction usually contains
trace amounts of oxygenated constituents
and may still be a valuable material of com-
merce ("washed lemon oil"), or it may be
retreated to remove those traces of useful
flavoring materials.
A solvent-free terpeneless oil may be
produced without heat by diluting strongly
with water, separating the oil and eventually
recovering the alcohol for reuse, or by
distilling off the alcohol, after which the
terpeneless oil separates. This is better done
under vacuum to keep the boiling point low
to minimize degradation, but this involves
having chilled water (brine) in the conden-
sers to avoid losing alcohol, a highly taxed
ingredient in most locales. The oil may
be dried with anhydrous sodium sulphate,
which itself is later dissolved in water to
recover and recycle adsorbed oil.
Clear soft drinks require the use of such
soluble oils. The solubility here refers to
solution in sugar syrups at a level required
to give the desired flavor strength in the
finished drink, and not necessarily to total
miscibility at any level with the solvent.
Such miscibility is not often the case. With
citrus oils, the terpenoid hydrocarbons
are separated from the more water-soluble
oxygenated components; with ginger oil, the
result is the same although the water-soluble
part is extracted from the large proportion
of the insoluble resins of oleoresin ginger.
In each case, a trace of terpenes generally
remains in the finished soluble essence, not
necessarily bad from the flavor and aroma
point of view as long as clear solutions are
obtained at the level of use.
Soluble essences may also be made from
terpeneless and sesquiterpeneless oils ob-
tained through distillation processes by
simple solution in the aqueous alcohol, but
still suffer from the effect of heat in the
 Flavor Manufacturin g 553

distillation step. Most flavorists object to the

flatness of the flavor profile and a lack of
fullness in the flavor. For some usages, there
may be a cost advantage that renders them
eminently desirable. Whatever the source,
top notes and nuances may be added by the
careful use of other natural flavors or, where
permitted, by nature-identical chemicals.

Distillation
A very well-known unit operation in the
chemical, pharmaceutical, perfume and
flavor industries is distillation: a process for
the separation of substances based on dif-
ferences in their vapor pressures. It has
been known for centuries and is probably
the most widely used unit operation. The
petrochemical industry is virtually based on
this technique, and much study has gone
into design of equipment to separate multi-
component crudes into fractions with
minute differences in structure and vapor
pressure. The results of such research activi-
FIGURE ll-3. Distillation columns for the
ties have, of course, found their way into the processing of essential oils. (Courtesy ofT. Hasagawa
flavor industry on a much smaller scale. Co., Ltd.)
Among the uses here are for: (a) the re-
covery of volatile components, (essential
oils) from aromatic plant materials; (b) the vapor rates, theoretical plates, reflux ratios,
fractionation of those oils with more or less McCabe-Thiele diagrams, etc., and only the
efficiency (e.g., rectified peppermint oil); surface will be scratched in the descriptions
(c) the separation of components of the which follow (Anon 1989e; Charm 1986;
essential oils to more concentrated states; Dimitrov, Dimitroz and Dimitrova 1975).
(d) the recovery of solvents during the
extraction process; (e) the concentration Simple Distillation
of natural flavoring materials (e.g., fruit Simple distillation consists of converting
concentrates); (f) the more limited use of a liquid into its vapor by the application
destructive distillation to make pyroligneous of heat in a still and transferring this vapor
acid; (g) in numerous research and analyti- into a condensing section, where the heat
cal techniques; (h) in the azeotropic separa- is removed and the vapor is converted
tion of components; and (i) in the separation back into a liquid minus the non-volatile
of synthetic crude chemicals to obtain in- components of the original liquid. This
dividual fractions of high chemical purity process may be carried out at atmospheric
and organoleptic flavor quality. pressure, under vacuum, or (almost never in
The processes are the same whatever the this industry) under positive pressure. [An
size of the operation, whether in laboratory exception is the recovery of materials that
glassware or in 2,000-5,000 gallon plant are gases at room temperature , such as
stills. Texts in chemical engineering devote carbon dioxide and sulphur dioxide used in
much discussion to the theory of distillation, extractions.] The heat may be applied by
554 Source Book of Flavors

direct fire, as in primitive operations, by low

or high pressure steam in a jacket or coils
internal to the still, by circulating hot oil or
water in the jacket or coils, by hot vapors of
high-boiling liquids in heat exchangers or by
a combination of methods. The shape of the
vessel is not critical except for resistance to
external/internal pressure. The pipe lead-
ing to the condenser is usually of relatively
large diameter, and the condenser may be
fabricated from the same material as the still
pot or it may be more exotic. The cooling
medium is most often circulating water or
brine or may be simply a coil of pipe in
a bath of water. Actual design depends
on whether or not the unit is to be run
under vacuum, the cost and availability of
water (e .g., single or multiple pass shell and
tube designs) and, frequently, on economics
rather than technical feasibility.
FIGURE 11-4. Rectification column for the
Evaporation processing of essential oil. (Courtesy of Sanofi
Evaporation is a case of simple distillation Bioingredients, Inc.)
applied to the removal of solvents from
solutions of non-volatile materials where the
non-volatile (relatively speaking) materials each fraction being richer in some com-
are the desired end product. Units have ponents than the starting material and often
been improved to where the evaporation being virtually (never actually 100 percent)
takes place in stages under reduced pres- 95-100 percent of a particular chemical. For
sure, where the condensing medium in this purpose, the still is fitted with a column
effect is the substrate for the next stage, that allows partial condensation followed by
thereby saving fuel costs and cooling costs. re-evaporation over and over again. As the
In the flavor industry, these may be used for vapor proceeds up the column, it becomes
the production of concentrated fruit juices, ever richer in the most volatile component,
such as cherry, with special equipment and then in the next most volatile compound,
precautions to condense and save the highly ad infinitum. The column may be fitted cen-
volatile top notes. The designs minimize trally over the still pot or it may be eccentri-
exposure to heat both temperature-wise cally mounted and is not empty but contains
and time-wise. The 150-fold or 300-fold top any of a number of packing materials from
notes are added back to the concentrate the old standby Raschig rings to Berl sad-
before it is used. dles, through perforated plates or bubble
caps, to any of a number of patented shapes
Fractional Distillation claiming to have lower pressure drop, lower
Fractional distillation is used to separate HETP (shorter Height Equivalent to a
miscible liquids having different boiling Theoretical Plate, see explanation below),
points. Where the separation is minimal, the greater throughput at a given pressure drop,
process is sometimes called "rectification." none of the above or all of the above. The
In most cases, separation is more complete degree of separation depends on the relative
taking fractions of different boiling points, volatility, difference in boiling point at the

pressure of operation, mutual solubility of
the many components, etc., some facets of
which are still not completely understood in
spite of computer modeling of the system.
There are noted phenomena, such as
azeotroping, where two or more compo-
nents form a constant boiling mixture in
which the composition of the vapor is the
same as that of the liquid, rather than the
vapor being richer in the lower boiling com-
ponent so that no further separation can
take place by fractional distillation. Tables
of such mixtures are available in the litera-
ture (Weast 1988), but are by no means
complete. The very large number of chemi-
cals in any essential oil makes a complete
tabulation almost impossible.
Stills have been designed for continuous
operation with feed taking place either into
the pot or someplace low on the column,
and arrangements so that vapors present at
a given level may be partially condensed
and removed continuously from the system.
Early versions used perforated plates or
bubble cap trays; packed columns with
redistributors placed at different heights in
the column may also be used. Fractionating
columns have also been described as being
a series of vertical simple stills where the
vapors condensed from the still on the low-
est level becomes the pot liquid for the next
level, with condensing vapor providing the
heat to vaporize the liquid in the next stage
and so on up the line. Part of the vapor may
be condensed and returned to the still rather
than being taken off as end product, with
the proportion returned to that taken off
called the reflux ratio. Most of the frac-
tionating columns used in the flavor industry
are of the batch type, with still pots in the
50-1,500 gallon range and columns from 4
to 48 inches in diameter and heights to 100
feet. They operate at pressures that may
reach less then 1 mm at the top of the
column, with pressure drops down the
column typically of 10 to 30 mm of mercury.
More efficient heating systems have been
devised for better heat transfer, either
integrally or offset from the stillpot, with
Flavor Manufacturing 555
convection or pump-forced circulation.
Glass stills with 72- or 100-liter pots are also
not uncommon. Mechanical and electro-
magnetic reflux splitters with electronic con-
trols are used with an almost infinite range
of reflux ratios possible; the higher the ratio,
the purer the vapor coming off, in over-
simplified terms, and the longer it takes to
complete a batch. Theoretically, the re-
moval of any vapor upsets the equilibrium
that must first be achieved to set stable
conditions. Thus, there is a compromise
between the separation that is theoretically
possible and the pragmatic operation of a
still.
When a column is in equilibrium with no
vapor being taken off, there is a steady
gradation of composition of the rising vapor
and falling condensate. If one supposes a
plane across the column at height A and
another below it at height B, and if the
composition of the vapor rising at the upper
plate has the same composition as the liquid
falling from the lower plane, the distance
between them is called a "theoretical plate."
The efficiency of a column for separating a
given mixture depends on the number of
theoretical plates in the column. It is often
forgotten that this height is dependent on
the mixture being distilled, e.g., the differ-
ence in boiling points of the components at
the pressure in use and the effectiveness of
the packing material in allowing the mixture
to come to equilibrium. The greater the
difference between the boiling points, the
lower this height becomes. In complex mix-
tures, the HETP may be no more than a
guess based on experience. When com-
paring commercial packings, the test mix-
ture must be specified or a comparison is
meaningless.
Steam Distillation
Steam distillation is used when the liquid
has a boiling point above that of water and is
immiscible with water, or for the recovery of
volatile oils from aromatic plant materials.
Two types of stills may be used. In one, the
plant material is put into a still pot with
556 Source Book of Flavors
excess water and possibly some salt, is pre-
ferably agitated and the water boiled carry-
ing with it the volatile oil. The oil, either
heavier than water (e.g., clove) or lighter
than water (e.g., nutmeg) is separated by
decantation in one or more continuous
separators with the aqueous layer returned
to the still pot as needed to maintain the
starting volume. The heat required may be
from external sources, direct firing in primi-
tive cases, by hot oil, steam in jackets/coils
or by direct injection of steam. The other
type of still is almost like an extractor, with
the plant material supported on a perforated
base plate and the steam introduced below
it. That steam may be regenerated in an
offset evaporator, with the condensed water
returned to the evaporator after the oil
is separated. These stills are usually well
insulated so that condensation does not take
place before the vapor gets to the con-
denser. In either case, as distillation prog-
resses, the ratio of oil to water continuously
decreases, with the distillate eventually
having no oil. For economic and pragmatic
reasons, the distillation may be terminated
when experience shows that it is wasteful to
go on longer.
Destructive Distillation
Destructive distillation is quite rare and is
used for the production of pyroligneous acid
or wood vinegar. The plant material, here
pine wood, is loaded into retorts heated by
direct firing to about 370°C (700°F). The
vapors produced are condensed, the distil-
late being a crude mixture of methanol,
acetic acid, acetone, furfural, tars and
related products. This mixture is then frac-
tionated to produce the pyroligneous acid
of commerce. When charcoal has been pro-
duced commercially from pine wood, the
condensate is a by-product and the retorts
are so large that cart-loads of pine are
driven into the unit on tracks, the large
doors closed, distillation started and even-
tually the carts removed when they have
cooled somewhat (or else they catch on
fire!) to get the charcoal.
Molecular Distillation
Molecular distillation is a very high-vacuum
technique with a short path between the
liquid surface and the condensing surface.
The pressure in the still is reduced so that it
is below the pressure of the vapor in equili-
brium with the liquid. The condenser is a
centrifugal type and the distance between
the liquid and the condenser is less than the
mean free path of the vapor molecules. In
order to get high purity, the condensed
vapor may be redistilled, and the process
repeated as necessary since there can be no
more than one theoretical plate present.
Combinations
Combinations of the previously discussed
types of stills may be used, and each is
capable of modification to suit particular
purposes. Ancillary equipment may be
made of many materials, although stain-
less steel of the types 304, 304ELC, 316
and 316ELC are most common, replacing
copper and tin-lined copper, and glass or
glass-lined units are required in many
instances to avoid undesirable color. See
Charm (1986) and Considine and Considine
(1989) for a description of the theory and
practice of distillation, and the earlier work
by Guenther (1948-1952) in its application
to production of essential oils.
Ancillary equipment needed for vacuum
distillations include one or more types or
sources. Pumps may be water- or oil-sealed,
of the rotary or reciprocal type, often being
larger versions of those commonly used in
laboratories. Water jet and steam jet evacu-
ators of one to five stages with intermediate
barometric or surface condensers are used,
depending on the degree of vacuum that
must be attained. Molecular stills require
these to be used as atmospheric-end stages
for mercury-diffusion pumps. Depending on
the boiling points of the lightest fractions,
condensers may require brine cooling or
simple chilling to just above the freezing
point of water, particularly where surface or
well water runs rather warm. Evaporative
water recirculating systems are normal, con-

sidering the cost of water and the regula-
tions against excessive discharge. Two
stages of condensation may be used, the first
with ordinary water and the one closer to
the pump using much less but much colder
coolant.
Aroma Distillates
In the manufacture of flavors, distillation
with alcohol at atmospheric pressure is
widely used to separate volatile aroma and
essential oil from a whole range of aro-
matic botanicals (e.g., herbs, citrus peels,
roots, seeds, flowers, leaves, etc.). This co-
distillation of botanicals, alcohol and water
enables vaporized volatile components to
mix with the alcoholic vapors immediately
after their separation from the plant mate-
rial. The presence of ethanol in the distil-
late not only prevents deterioration of the
thermo-labile components, but also con-
tributes significantly to complex chemical
reactions between the various acid, alcohol
and ester constituents, leading to a con-
siderably improved distilled flavor profile.
Since fractionation is not desired, only
the simplest of columns is used. In very rare
circumstances, vacuum may be used requir-
ing special condensers and cooling systems
to prevent the highly volatile top notes from
disappearing into the pump; vacuum is
normally proscribed.
Just as in steam distillation, two types of
apparati may be used: (a) The coarsely
comminuted botanicals are placed inside an
agitated (or not) pot still with the aqueous
alcohol and allowed to extract at least over-
night and better for 24 to 48 hours, or (b)
the botanicals are loaded into a cylindrical
vessel fitted with a perforated stainless-steel
plate above the bottom. Heating jackets or
coils are limited to the surface or space
below the support plate to prevent scorching
of the botanicals and the creation of a burnt
flavor as the distillation progresses. Aqueous
alcohol is added and allowed to stand in the
same way.
The remainder of the process is essen-
tially the same thereafter. Heating of the
Flavor Manufacturing 557
still should be slow and carefully controlled
throughout the distillation, permitting only
a slow distillation rate with an initial period
of total reflux. The first fractions are col-
lected separately only after the vent to
atmosphere carries a scent of significant
aroma that can be sniffed without irritation.
The main fraction is collected without reflux
(partial condensation of the vapor returned
to the still). While the condensate starts at
a relatively high, (circa 90 percent B.V.)
concentration of alcohol, depending on the
initial concentration of the menstruum, the
concentration decreases as the distillation
progresses and the process becomes more of
a steam distillation. Control is as much by
odor and taste as the skill of the operator in
keeping the flow rate constant, checking on
clarity and changing fractions is important.
When the alcohol content drops to about
65 percent B.V., checked by a simple hy-
drometer test, reflux is adjusted to slow
down the falling alcohol concentration. At
about 55 percent, the end of the main
fraction is reached and an end fraction is
taken. The exact end is organoleptically
determined by frequent sniffing and tasting
as much as by the alcoholometer reading;
small fractions may be taken for additional
evaluation and return to the middle or end
cut as indicated. Distillation is continued to
recover as much of the alcohol as possible
for economic reasons and more water may
be added to the pot to assist. The marc is
discarded as usual.
The main fraction is diluted with water
to the desired alcohol content. It may be
cloudy and is allowed to stand to separate
the terpenes that float to the top. These are
decanted or centrifuged just as in the wash-
ing process to remove terpenes, and the
main fraction is filtered for complete clarity.
This fraction is returned to the cleaned still
(or another similar unit) for redistillation in
the same way with as much or more careful
control of fractions to yield the finished
flavor distillate of the finest aroma and taste.
The last fractions (tails) of both distilla-
tions are combined, filtered if necessary and
558 Source Book of Flavors
redistilled usually with additional packing/
reflux control to obtain an alcoholic solution
of higher alcohol content for reuse in sub-
sequent batches of the same flavor type for
economic reasons.
Distillates of citrus peel are usually ad-
justed to 60 percent alcohol B.V., whereas
most other aromatic distillates are between
35-40 percent B.V. In lieu of botanicals,
essential oils obtained by pressing (citrus
oils) or other means may be employed in the
same way in the pot type of still, but the
quality is not identical.
The methodology is adaptable to co-
distillation with other solvents often without
water present. For example, cocoa nibs or
cocoa powder are extracted with propylene
glycol to obtain a clear creme de cocoa
flavor. Heating must be modified to use hot
oil or high-temperature vapors in the coils/
jackets because of the boiling point of the
solvent.
Percolate and Macerate Distillation
There is a modification of the foregoing that
separates the extraction step from the distil-
lation step. Following normal percolation
and maceration, the extract is allowed to
stand for two to three days and any in-
soluble matter is separated. The clear
extract is then put into a still for distillation
at atmospheric pressure in the same manner
as for aroma distillation. The advantage
is that the solid botanicals are not heated
so that the distilled product has a keener
aroma more desirable for some usages. It
has already been mentioned that expressed
citrus oils are so used.
Freshly prepared distillates of all types
(simple distillation, fractionation, etc.)
often have an objectionable "still odor."
This may be removed by aging, sometimes
simply by standing in an open container
overnight or for a day or two, and some-
times by aging under more carefully con-
trolled conditions of temperature, exposure
to artificial light, sunlight air or inert gas,
etc., depending on the chemical nature of
the constituents. Aldehydes should not be
allowed to oxidize by exposure to air, for
example.
The discussion above has often referred
to natural products. Synthetic (artificial) or
nature-identical materials may be handled
in similar ways, the exception occurring only
later on in the labeling of the end product in
the country of use.
Sterilization of Herbs and Spices
Research into the hygiene and bacteriologi-
cal aspects of food processing over the past
few decades has revealed that with few ex-
ceptions whole herbs and spices have no
significant bactericidal properties per se. On
the other hand, they are a rich source of
viable bacteria, bacterial spores, molds and
insects, some of which are pathogenic or
otherwise toxic. Governmental authorities
have tightened the limits on contamination
that may be permitted to be present, con-
sidering the increase in consumption of pro-
cessed foods at various stages in processing.
Spices are used extensively in seasoning,
although they are often replaced by spice
extracts. Most spices and other botanicals
originate in tropical or semitropical regions
and are harvested by rather primitive
methods, so hygiene and cleanliness are not
obvious needs, or attainable ones. Practi-
cally no attempt is made to limit contamina-
tion in any stage of the growth, cultivation,
harvesting, preparation for marketing,
storage or transportation of the botanical to
the ultimate processor in the flavor industry.
Tighter standards are being increasingly im-
posed at the port of entry into big-user
countries, such as the United Kingdom,
European Common Market and the United
States. This has done much toward improv-
ing the overall cleanliness and relative free-
dom from gross filth, vermin feces or vermin
of most whole spices and other botanicals.
The pattern of bacterial contamination has
not been much changed, as there are too
many possible sources of contamination to
permit economically practical reduction of
mold count and bacteria. Consumers and

consumer advocates have been raising loud
voices, however, and may force additional
measures to be taken .
Of the possible methods of controlling
and reducing the bacterial load of spices used
in seasoning, fumigation with a sterilant gas
offers the most effective methods, accepting
the need to limit residual gas and ensuring
minimal damage or change to the aromatic
constituents (Mayr and Suhr 1973; Weber
1980). An alternative to fumigation is expo-
sure to irradiation with high-density gamma
rays (Vajdi et al. 1973; Vajdi and Pereira
1973; Gottschalk 1977). This is an effective
method of sterilization, but at the dosage
levels necessary the product may develop
off-odors and off-flavors and undergo un-
desirable color changes. Other methods like
microwaving have been proposed, but are
not yet accepted.
Gas sterilization or fumigation is normally
a specialist operation carried out by the
major spice processing houses. Common
gases are ethylene oxide and propylene
oxide. Both are highly flammable, form
explosive mixtures with air and are toxic per
se. They are usually diluted with 10 per-
cent carbon dioxide or 50 percent methyl
formate, both of which are commercially
available in cylinders. Chlorofluorohydro-
carbons have been used, but are increas-
ngly proscribed for environmental as well as
toxicity reasons. In many countries, gases
used for fumigation are strictly controlled
by legislation, as are the residual gas levels
permitted.
The equipment necessary for fumigation
is specifically designed and generally com-
prises a rectangular chamber with a large
access opening to handle bales of botanicals.
It must be able to withstand vacuum of
about 20 Torr and requires ancillary equip-
ment to produce that vacuum, control
humidity and gas flow as well as to transport
the bales. The spices are loaded into the
chamber, which is then rapidly evacuated
and sufficient sterilant gas metered in to
achieve a concentration of about 1,000
grams per cubic meter. The conditions are
Flavor Manufacturing 559
allowed to stabilize for 6-18 hours (over-
night typically), the temperature and rela-
tive humidity being closely controlled within
parameters determined to be optimal for the
particular spice and fumigant gas, equip-
ment size, type of bale, etc. At the end of
the sterilizing process, the gas is removed by
evacuating the chamber and purging with
inert gas and/or air; the process is repeated
until the residual gas is at an acceptable
level.
The toxicity of the sterilant gas and of
its reaction or interaction with compounds
present in the botanical, like salt, to form
ethylene chlorohydrin (itself a sterilant,
but of high toxicity) has been of concern
(Scudamore and Henser 1971; Wesley
Rourke and Darbishire 1965). Toxicologists
have concluded that the amounts remain-
ing are not persistent and offer no health
hazard. Authorities have set standards for
the use of sterilant gases, for residues to
remain and for the conditions of their use. It
is best to verify the current regulations by
referring to CFR 21-121.1076, 121.1232
and other sections in the United States.
Flavorists will not generally be concerned
FIGURE 11-5. Bulk storage of flavoring materials in
compounding bay. (Courtesy ofT. Hasagawa Co.,
Ltd.)
560 Source Book of Flavors
FIGURE 11-6. Compounding bay. (Courtesy of
Sanofi Bioingredients, Inc.)
with these details, as the spices they use will
already have gone through the sterilization
procedures.
LIQUID FLAVOR PRODUCTION
Flavor ingredients should be stored in cool
areas where they will be stable to chemical
changes. Most chemicals will be stored in
drums or other forms of bulk storage. While
many companies still use manual transfer of
ingredients from this bulk storage to the
appropriate mixing vessels, some companies
have automated this transfer and weighing
process. The process may be entirely closed
to the atmosphere and computer controlled.
This minimizes losses of flavor chemicals
to the environment (health and economic
reasons) and minimizes errors in selection of
chemicals and weighing. As the components
of a flavor are weighed into the mixing
vessel, it is essential that they be properly
mixed to provide a uniform flavoring.
Mixing
The basic unit operation of all compounded
liquid flavor production is mixing (Anon
1970a; Uhl 1987), although it may be asso-
ciated simultaneously with other unit opera-
tions to produce homogenous end products.
Methodology has historically grown, em-
pirically, with virtually no standardization
of method, or equipment or consideration
of optimum conditions. Sometimes, a
company has standardized on machines
from one supplier, or of one type, to mini-
mize repair part problems and maintenance
expertise.
Flavorings generally consist of a large
variety of different ingredients, ranging in
physical character from very fine powders
through crystalline solids to viscous pastes,
thick liquids or mobile liquids. Concentra-
tions vary from ppm to very large propor-
tions of the mix, even over 95 percent of a
single ingredient. They may then be carried
in a liquid or solid solvent/diluent of varying
viscosity and/or bulk density. This wide
spectrum of conditions and concentrations
makes mixing a vitally important step in
flavor production if consistent and homo-
genous products are to result.
In the production of compounded flavor-
ings, the mixing operations may be either:
(a) solid/solid-as in the production of
powdered flavors or seasonings, involving
the intimate blending of particles of the
same or different sizes and bulk densities
(Fischer 1960); (b) solid/liquid- as in most
liquid flavorings , involving solution or dis-
persion of one or more solids into the liquid;
(c) liquid/solid-as in the preparation of
plated or dispersed spices into which thin or
viscous liquids, pastes, oleoresins, etc., are
spread onto a dry carrier (Fischer 1962); and
(d) liquid/liquid- as in essential oil blend-
ing, blending of flavorings or in the dilution
of a liquid flavorant with another liquid sol-
vent. In the latter, a special case is where
the liquids are wholly or partially immiscible
and an emulsion is to be formed. This is
hardly different from the food and chemical

industries, where the range may be even
wider and where more attention may have
been given to methodical determination of
the mixing parameters, given the tonnage
and batch sizes involved.
Such a diversity of possible constituents
and end product requirements calls for
mixers and mixing vessels in a wide range
of design and operating capabilities from
bench size to those with capacity of hun-
dreds of gallons or cubic feet. Here we will
discuss primarily liquid flavor production,
with other flavorings material covered m
separate sections of this chapter.
Mixing Plant
The process of mixing is essentially one of
agitation, with the type, extent and intensity
determining the nature of the processing
plant used and being determined by the
nature of the ingredients. Most liquid
mixing is carried out in open or closed
cylindrical vessels using a mechanical low-
or high-speed agitator. There may or may
not be baffles affixed to the walls and the
bottom may be flat, dished, hemispherical
or coned. It may be jacketed and/or coiled
for heating and/or cooling. The design, size
and speed of the impeller determines the
(a) slow speed (b) medium speed
FIGURE 11-7. Flow motion in a vertical tank without baffles. (Heath 1981)
Flavor Manufacturing 561
flow pattern and degree of turbulence in the
vessel. The optimum ratio of bulk fluid flow
to turbulent flow depends on the nature of
the materials to be mixed. This must be
determined experimentally to ensure the
minimum expenditure of energy and expo-
sure of the product to unnecessary agitation.
It must be admitted, however, that many
companies have used the "seat of the pants"
method: this works, that does not; we have
this agitator, so it must be used whether or
not it is as efficient as it might be, particu-
larly if this is the only batch of this product
we will be making this week, month or year.
In the case of miscible liquids and the solu-
tion of solids, smooth mass flow is desirable
to achieve homogeneity; the dispersion of
solids to form a slurry or of immiscible liquids
demands high shear and good turbulence.
Flow is induced in a bulk of liquid by use
of one or more propellers mounted on an
impeller shaft. Among the most widely used
types are: (a) marine propeller, (b) pitched
blade turbine, (c) flat blade turbine, (d) flat
blade paddle and (e) pitched blade paddle.
Good mixing depends on the correct pattern
of fluid flow and turbulence, and this will
dictate the best choice of impeller. Again,
much mixing has been and is being done
with a far from optimum selection of type.
(c) high speed
562 Source Book of Flavors

If the impeller is mounted vertically in The positioning of the impeller is important

the center of the mixing vessel, the resultant
smooth bulk flow is cyclonic in the direction
of rotation of the paddles. With sufficient
speed, this can create a vortex with the
ultimate incorporation of air into the sys-
tem, which is not always acceptable (Fig. 11-
7). This motion can be modified by the use
of baffles mounted vertically on the walls
of the vessel so disrupting the flow stream
causes turbulence and an increased rate of
mixing (Fig. 11-8). The bulk swirling of the
body of the liquid can also be prevented by
mounting the impeller off-center and/or at
an angle to the vertical walls of the mixing
vessel or horizontally through the side wall.
in achieving the desired mixing flow pattern
and can be determined by trial and error.
When two or more impellers are placed on
the same shaft, the distance separating
them may be varied (frequently being one
impeller diameter apart) and the thrust of
the top one may be downward while the
lower one has a counter upward thrust. This
gives a good mixing pattern between the
blades (Fig. 11-9). However, they may both
thrust downwards. Impellers may be
mounted on concentric shafts rotating in
opposite directions or at different speeds,
and the impellers need not be of the same
type. Scraper types with blades operating

Axial flow with propeller Radial flow with turbines

and baffles and baffles

Flow pattern with off-centre Flow pattern with

impeller, vertical inclined impeller

FIGURE 11-8. Flow patterns in vertical tanks. (Heath 1981)

 Flavor Manufacturing 563

close to the vessel walls are used for viscous

materials, alone or in combination with
paddles operating on a concentric shaft.
Impellers may be integral to the mixing
vessel, particularly in the larger sizes,
mounted at the top or for side entry. Smaller
sizes up to 2 HP, may be portable from one
vessel to another and clamp mounted on
suitably reinforced sections of the tank top.
Alternatively, they may be mounted on a
gantry. A feature of portable impellers is
that they may be adjusted to enter at dif-
ferent angles and positions. The lowest cost
models have a fixed high, low or medium
speed, but others may have the speed
adjusted by variable speed pulleys, elec-
tronically or hydraulically. FIGURE 11-9. Flow pattern of two propellers
Impellers are typically designed to be mounted on same shaft. (Heath 1981)
about one-third the diameter of the mixing
tank in which they are to be used. If one set
of blades is mounted on the shaft, it should the entire mass is involved, without "dead
be set to operate· at a distance of about its spots" in the vessel.
own diameter from the bottom of the tank. The mixing patterns or optimum posi-
These parameters are by no means fixed tions for mixers using certain types of impel-
in stone. Slow-speed flat blades are often lers are shown in Figs. 11-8, 11-9 and 11-10.
larger and high-speed small blades smaller The literature available from purveyors of
in diameter. Care always should be taken to mixing equipment also gives flow patterns.
ensure that any adjusting screws are secure
and tight, as the movement of the impeller
Continuous Mixers
during use can result in fouling of the tank
walls, damage to the motor and/or the tank Continuous mixers are used where solids
and the contents. At least, time and effort have to be blended with liquids to give a
will be expended to retrieve a dropped thin pumpable suspension, and many are
impeller from the bottom of the vessel. also of value as a preliminary stage in the
Mixing tanks for use in the flavoring production of emulsions. Several machines
industry are made mostly of stainless steel, having unusual design features are available
although older tanks of tinned copper commercially and reference should be made
remain in use. Usually they are provided to the manufacturer's literature for technical
with one or more run-off valves at the very specifications. One such mixer has a two-
bottom and part way up the side wall. They stage head; the first disintegrates any large
may be coupled in line or used individually. particulate matter, the reduced solids then
The operating depth of the liquid in the tank being drawn down into the second head,
is optimum at twice the diameter of the tank where it is finely dispersed by hydraulic and
and should normally be not less than the mechanical shear. Another in-line machine
diameter of the tank if good mixing is to be also has a two-stage flow pattern embody-
achieved. The ratio may vary considerably ing a retention chamber through which all
where large volumes of liquids are to be the product must pass. This ensures very
mixed, but in such cases the flow pattern thorough agitation and mixing. Another
must be carefully determined to ensure that continuous mixer consists of two stator
564 Source Book of Flavors

Clarification
With the exception of emulsions and certain
operating level
fruit-based products, the majority of liquid
flavorings are required to be bright and re-
main clear of any sediment, suspended
matter, oily globules or other extraneous
matter not only when produced but also
throughout their shelf life. Turbidity in a
minimum operating flavoring may be due to varied causes and in
level (=X)
order to apply the correct method of clari-
\--,1~-----';...._-1 ~
fication, it is generally necessary to under-
stand the nature of the fault and the reasons
for it. In all cases, the turbidity, opalescence,
haziness, precipitation or sedimentation in a
flavoring is due to the presence of matter
that is not in solution in the solvent present.
.f+.o~ t In some cases, the fault develops on long
D- 20 storage after the initial compounding due to
+X either chemical and/or physical conditions.
The removal of the matter is effected by
some form of filtration or by centrifugal
separation, depending on the nature of the
product, the relative proportion of solid
matter to be removed and, in particular, the
degree of stability and volatility of the prod-
uct to be cleared. In a few cases, the adjust-
ment of the solvent by the addition of a
small amount is all it takes to solve the
problem. The material may also be chilled
before filtration to take advantage of the
increased solubility that will result after
the batch returns to ambient temperature,
although the chilling could throw more out
of solution prior to filtration.
FIGURE 11-10. Optimum mixer positions for The process of filtration is one of separa-
normal working. (Heath 1981) tion in which solid matter dispersed in a
fluid phase can be separated by passage
through a porous membrane or septum, the
texture or apertures of which are sufficiently
plates and a high-speed rotor between them. small to retain the solid particles but allow
The plates carry a pattern of concentric the fluid to pass th.t:ough (McDonald 1971a,
blades very similar to those in a pin mill. 1971b, 1972). In the case of liquid flavor-
This operation sets up considerable turbu- ings, the fluid phase is the solvent containing
lence and ensures very adequate mixing. the dissolved aromatic constituents. If the
Still another type uses fixed spiral or helical insolubles causing the turbidity represent
blades or vanes in a pipe past which the only a small proportion of the bulk, the
crudely mixed liquids must be pumped, process is usually referred to as clarification.
changing laminar flow to turbulent. The membrane or septum is called the filter

medium and the structure supporting this
and providing a receptacle for the solids is
called a filter. The object of filtration may
be to clarify the fluid portion or to collect
the solid portion, whichever is the desired
end product. Ideally, the filter medium and
any associated filtering aids that may be
used must not impart any color or off-flavors
or change the flavor profile of the flavoring
(Anon 1970b).
As with the mixing operation, the phy-
sicochemical properties of flavorings dem-
onstrate such wide compositional variations
that no one type of filter is universally ac-
ceptable. Whatever the design of the filter
or operating characteristics, four factors are
of importance: (a) As already noted for the
filter medium, the material of construction
must in no way impair the odor, flavor or
color of the product being filtered, be it the
solid or the liquid as the desired end prod-
uct. In this respect, wood, iron, tin and
copper are to be avoided and stainless steel,
porcelain, glass, nickel, Monel, other alloys
and some plastics are materials of choice;
(b) The filter must be designed for safe and
effective operation consistent with the
volatility and possible flammability of the
product, the pressure involved and the vol-
ume throughput required. In the flavor
industry, special precautions to prevent
exposure of personnel to toxic chemicals is
of limited concern, albeit in high concentra-
tions some ingredients may cause skin rash,
difficulty in breathing or other irritations;
(c) The design must be such that the maxi-
mum of the desired product is recovered;
(d) The unit must be capable of easy and
thorough cleaning so as to ensure the mini-
mum of contamination risks if it is used for
different aromatic products, very often the
case in the flavor industry. Filters used in
flavors fall into one of three categories:
a. Gravity: funnels, filter bags
b. Pressure: filter press, disc and hori-
zontal plate filters, filter candles
c. Vacuum: Buchner funnel, Nutsche,
leaf, tube or rotary filters.
Flavor Manufacturing 565
In the case of aromatic liquid products such
as essences and flavorings, closed circuit
filtration is a desirable feature. When the
volume to be handled is large, continuous
in-line operation is a necessity.
Filter choice is governed by certain key
operating factors, including: (a) the area of
the filtering medium; (b) the resistance of
the filter and the filter cake (the solids
already removed); (c) the viscosity of the
filtrate; and (d) the pressure difference
across the filter membrane. Filtration is
initially fast, but slows down progressively
as the filter cake builds up on the medium.
The rate of flow through such a porous filter
bed is governed by the following Kozeny-
Carmen equation:
ilP
Rate of flow (Q) = KA-
YJL
where A = cross sectional area of the bed
.:lP = the pressure difference across
the bed
11 = viscosity of the fluid
L = depth of bed
and K = permeability coefficient, which
is calculated from the following
relationship:
where £ = the porosity of the bed
S = the area per unit volume of the
solids forming the bed
From these relationships it is obvious that
the rate of flow of the filtrate is directly
proportional to the filter area and the pres-
sure differential, and is inversely propor-
tional to the viscosity of the filtrate and the
depth of the filter bed (cake). The flow rate
is also proportional to the porosity of the
bed; a 10 percent change in this due to
compacting can produce a reduction in flow
rate by about 65 percent.
The filter medium must also be: (a) inert,
(b) effective, (c) mechanically strong, and
566 Source Book of Flavors
(d) of low retentive capacity for the liquid
phase. The media most widely used include
stainless-steel wire woven into a fine mesh,
sintered stainless steel, flannel, heavy
canvas, nylon cloth, Orion cloth, Dynel
cloth, felt and the almost universally appli-
cable filter paper in thin sheets or pads.
Glass cloth or pads are of some use and
asbestos pads were once used but are now
banned because of alleged toxicity. The
medium of choice will depend to a large
extent on the nature of the material to be
filtered. Very coarse particles may be re-
moved by straining through a woven or per-
forated metal screen sufficiently to clarify
the product, but if the particles are small,
filtration through an appropriate medium is
necessary to "polish" the liquid to complete
clarity.
Filtering
Frequently in the production of liquid flavor-
ings, a fine haze of oily globules separates
out directly after completion of compound-
ing or after a period of standing. This haze
or opalescence may be due to traces of
certain insoluble constituents (e.g., essential
oils, terpenoids, fixed oils, resins, etc.) or
may be insoluble reaction products. This
opalescence is often difficult to clear either
by allowing the product to settle, centrifuga-
tion or simple filtration through paper; its
clarification calls for the use of filtering aids
(Driscoll 1977; Fiore and Babineau 1979).
Types of Filtering Aids
The most widely used of them are:
Diatomaceous Earth,
Kieselguhr or Diatomite
A soft, bulky, grayish-tan powder compris-
ing 88-95 percent of hydrated silica (Si0 2)
together with traces of aluminum and iron.
It is a natural material composed of the
skeletons of prehistoric aquatic plants
(diatoms) having intricate and irregular
geometric forms and averaging 50-100
microns in diameter. It is this structure that
gives diatomaceous earth its highly desirable
filtering and absorptive properties. Diato-
mite is inert to most chemicals, is insoluble
in water and acids (except hydrofluoric
acid), but is soluble in strong alkali. The
bulk density averages 8-10 lbs. per cubic
foot and calculating from the true density,
the powder must consist of some 90 percent
of its volume as myriads of tiny inter-
connected pores. Diatomite absorbs 1.5 to
4 times its weight of water and has very
high oil absorbency. Commercial grades of
this material are processed in the United
States, Czechoslovakia and Scotland. In the
United States, there is a wide range of
grades available from several sources, and
the manufacturer's literature should be con-
sulted to find grade(s) most suitable to the
specific application.
Fullers Earth
This is a clay-like material with a high ab-
sorptive capacity. It is a natural product
consisting largely of montmorillonite (a
hydrated aluminum silicate) together with
some calcium carbonate in a finely divided
state. Fullers Earth is a fine, white to gray-
green powder, odorless and soft to the
touch. It is insoluble in water, but partly
soluble in hydrochloric acid.
Kaolin
A hydrated aluminum silicate processed to
remove naturally occurring impurities. It is
a soft, white, odorless powder that is in-
soluble in water, acid and alkalis. It has
good absorptive properties.
Magnesium Oxide and Carbonate
These are the very light, bulky, white
powders that are insoluble in water and
organic solvents, but are soluble in acids.
They have a good absorptive capacity for
oily materials.
Activated Carbon (Charcoal)
This man-made product has been included
with the warning NOT to use it. While

charcoal can be used as a filter aid, it is not
normally used except when color must be
removed. Insoluble in water and oils, it does
tend to absorb some of the trace top notes
and may change the flavor profile. There are
a large number of grades and particle sizes
from a number of sources and should be
tested only when and if all other filter aids
have been found wanting. The smallest
possible amount should be used.
Use ofFiltering Aids
Certain filters are designed to operate with
filtering aids that may be applied to the filter
medium either as a precoat, at about 5-
10lbs. per 100sq.ft. of filter area, prior to
the introduction of the unfiltered bulk or it
may be added directly to the bulk and mixed
to form a slurry, which is then fed into the
filter. The former method is by far the more
preferable, but there are times when it does
not work as well as the other, and there are
other times when both must be used in the
same batch. If precoating is not used, the
first parts of product may not be clear,
having gone through the initially uncoated
septum. They should be recycled into the
remainder of the batch, realizing that there
has been an undesirable exposure of the
contained aromatics to possible volatile loss.
Precoating also protects the filtering ele-
ments, provides initial clarity and generally
ensures a more uniform flow rate through
the bed. The addition of small amounts of
the aid to the bulk may help maintain a
more porous bed and reduce the formation
of a slimy film on the bed surface. Note also
that filter aids should not be used when the
desired end product is the solid, unless addi-
tional steps will be taken to dissolve it away
from the filtering aid.
Fining
In the case of wines and in certain other
natural alcoholic essences or extracts, an
alternative method of clarification is used to
reduce any sensory changes to the minimum
(Webb and Mabry 1986). This consists of
adding a clarifying or fining agent to the
Flavor Manufacturing 567
bulk, stirring well to ensure intimate con-
tact, and then allowing time for the solid
matter to settle and form a sludge. The
supernatant liquid is then pin-bright and
it may be decanted off.
The materials most widely used in fining
include: bentonite, casein, albumin, isin-
glass, and PVPP (polyvinyl pyrolidone).
The action of clarification may be entirely
mechanical, by adsorption of the suspended
matter onto the surface of the fining agent
or by chemical action such as occurs in the
removal of tannins. In the United States,
the types and quantities of fining chemicals
that may be used in alcoholic beverages are
defined by the Bureau of Alcohol, Tobacco
and Firearms (BATF 101); their latest regu-
lations (27CFR) should be perused.
Types of Filters
Gravity Filters
For many products, gravity filtration is
adequate and conveniently simple, fast and
requires inexpensive equipment. However,
in bulk production the method is usually too
unpredictable. The standard filter funnel
fitted, with a folded or fluted filter paper is
nearly universally used for all small-scale
filtrations and requires no further comment.
Many flavoring products based on fruit
juices are difficult to filter owing to the
presence of viscous and gelatinous mate-
rials. A preliminary clarification of the juice
may be achieved by passing it through a
conical bag made of felt, flannel, heavy
canvas or multiple folds of cheesecloth.
Admixture of the product with a filter aid
generally improves the flow rate, but gravity
filtration is invariably slow and this makes it
impractical except on a very small plant
scale. Even then, a battery of gravity filters
may be used in parallel on a single batch.
There is a type of bag filter that is inserted
into the top of an elongated cylinder with a
top lid capable of being closed by bolting or
by a toggle arrangement, and which is fitted
with inlet and outlet piping. Alternately or
simultaneously, it may have a perforated
568 Source Book of Flavors
metal basket in lieu of or to support the bag.
The design falls intermediately between a
gravity filter and a pressure filter, in that
only low pressures are expected in the pipe-
line into which it is inserted and acts more
like a strainer than as a filter. It is usually
referred to as a "pipe-line filter."
Pressure Filters
Filtration flow rates are generally increased
by the use of either positive or negative
(vacuum) pressure and such filters form the
majority of those used in current industrial
practice. Filter design falls into one of two
main classes: cake filters and clarifying
filters. The former are capable of hand-
ling large percentages of suspended solids
(which may or may not be the desired end
product), whereas the latter are desired to
remove generally less than 1 percent of solid
matter and to deliver a pin-bright liquid
product. There are some machines that
combine both types, running in series, with
the clarifying section following the cake
section. The pressure differential in a
vacuum filter is limited to 1 atm and, prac-
tically, is often much less than this. With
positive pressure filters the operating pres-
sure is usually not less than 25lbs. /in2 •
(1.76kg/cm2) and in most cases two to four
times that pressure. These conditions con-
siderably influence the design of the filter
and the safe working procedures to be
adopted.
Filter Press
Of all the positive pressure filters, the filter
press is the simplest, cheapest, most ver-
satile and widely used machine for the col-
lection of a solid product from a slurry or for
the production of a clear liquid product. It is
not, however, ideal. There are conditions
that contra-indicate its use: toxicity, vola-
tility and/or flammability of any drippage,
etc. Although it displays considerable vari-
ability in detailed design and operation, a
filter press basically comprises a series of
square filter units mounted by lugs on
parallel bars and held into position between
a fixed body and a movable head, which can
be screwed tight to form a fluid seal. The
filter units each consist of grooved plates
alternating with hollow frames, the plates
acting as a mechanical support for the filter
medium, which is usually in the form of a
firm woven cloth or disposable pads of the
same nominal size as the plates and the
frames. The corners of the plates and frames
when mounted form continuous channels
that permit the slurry, wash liquid and the
filtrate to flow into and out of the assembled
system. The machine is also known as a
"plate and frame" filter.
The filter press is assembled so that the
plates alternate with the hollow frames and
hold the filter medium firmly in place, the
edges of the medium being tightly secured
by the machined edges of the plates and
frames to make a good seal. To operate the
press, a slurry is fed under pressure into
the hollow frames via inlet ports in one
of the corner channels. The fluid passes
through the medium onto the grooved sur-
face of the plates on either side of the frame
into exit channels, leaving the solid matter
as a film within the frame. This solid matter
eventually builds up to fill the frame and
form the filter cake. In the case of liquid
clarification, the frames are generally pre-
coated with a filtering aid (at about 10lbs./
lOOsq. ft. of filter area), and filtration is
continued until the pressure builds up to the
maximum safe working pressure and/or the
flow rate becomes too slow for efficient
operation, whichever occurs first. At this
point, the filtration is stopped and residual
liquid is removed from the press by blowing
it through the filter cake with compressed
air or inert gas. Where the filter cake is
the product, filtration is similarly continued
until the frames are full and the pressure is
at the maximum. If a sufficiently large unit
has been used for the size of the batch, all
the bulk has passed through the press before
this occurs. Before the cake is removed, it is
usually necessary to free it from residual
mother liquor in the same way and/or to
wash it. A separate channel is provided for

this purpose to allow the inflow of washing
liquid. The washing of the cake and the total
removal of the mother liquor is not a par-
ticularly efficient or neat operation, and
some losses are inevitable. "Breaking
down" the press by releasing the screw pres-
sure and separating the plates and frames,
followed by filter cake removal, has always
constituted a problem and modern auto-
matic machines are more favored but more
expensive. Improvements have been made
to replace the screw closing devices by
hydraulically operated rams in larger sizes.
The volume throughput of a filter press
may be increased by adding more plates and
frames to the limit of the support bars'
length, and presses are usually purchased
oversized to allow this expansion. The
operating costs of preparing the press
plates, pumping through the slurry followed
by efficient washing, dismantling the press
and discharging the filter cake as well as
replacement of torn filter cloths and dis-
posable pads are relatively high so that care
is necessary in choosing a filter press of the
correct size and capacity to reduce the costs
to a minimum. Most presses are designed
for open operation and are provided with a
tray to catch any liquid, which eventually
and always escapes through the side and
bottom seals of the plates, particularly
toward the end of a run when the pressure is
highest. Losses of liquid product can be
significant and an enclosed (more expen-
sive) version of the press is preferable to
reduce such losses to a minimum. The opera-
tion of closed presses is more hygienic and
is recommended for the clarification of
liquid flavorings.
With the exception of the filter press,
all other pressure filters consist of a series
of filter elements within a closed pressure
vessel, which may be horizontal or vertical
in design. The filter elements may be either
plate or cylindrical and their arrangement
and operating procedures show wide varia-
tion. Some require much more case in their
assembly than others to prevent leakage and
bypassing of the frames. The following pres-
Flavor Manufacturing 569
sure filters may be of interest to prospective
purchasers of new equipment: vertical leaf,
horizontal plate, horizontal tank/vertical
leaf, and cylindrical. Most of these are
designed for fast flow rates and easy re-
moval of the filter cake, not necessarily for
fast and easy reassembly. Filter cakes may
sometimes be removed by backwashing and
flushing, obviating the need to open the
machine. Reference, of course, should be
made to the manufacturer's literature for
specific design and operating conditions and
where at all possible, inquiry should be
made of current users.
Pumps
The above filters require the slurry to be
fed in under a steady pressure and this is
achieved by the use of pumps. For most
products, the centrifugal type of pump gives
the best results, as there are no pulsations
to pack the filter cake causing irregular
deposition and blocking of flow channels.
The pressure delivered is self-limiting in the
design of the pump and may be selected to
conform to the design of the filter press.
However, such pumps produce a churning
action in the pump, particularly when flow is
impeded and this can result in the break-
down of solid particles (as in wet comminu-
tion), which then become more difficult to
retain on the filter medium. Other types
of pumps that are often used are the dia-
phragm pump, the plunger pump and the
reciprocating pump. These are satisfactory
in operation, so long as an air chamber is
installed to even out any pulsations and a
pressure-regulating relief valve is installed
to prevent excessive pressure from reaching
the filter press when the frames become full
or passage through the medium blocked.
Whichever pump is used, filtration should
always be started at low pressure and regu-
lated carefully throughout the process, so
that maximum pressure is obtained only
toward the end of the filtration cycle. This
will produce a more open-textured cake and
allow a better flow rate.
570 Source Book of Flavors
Clarification Filters
In the flavor industry, the principal need is
not to produce a recoverable filter cake, but
to obtain a perfectly clear filtrate from a
volatile, sensitive product containing only a
small percentage of suspended material. It
has already been pointed out that the
suspension may be oily rather than solid.
Clarification is conveniently carried out by
passing the product through a clarifying
filter, whose design is basically similar to the
enclosed pressure filters already described.
Those in common use are much smaller,
more mobile, have smaller cake capacity,
and are capable of easy cleaning and batch
operation with a variety of different flavor
types in reasonably rapid succession. Most
clarifying filters contain filter tubes or
ceramic candles mounted vertically within
the pressure vessel. They are often designed
into a portable processing unit, comprised
of the filter, a pump, a stainless-steel tank
and mixer for a completely self-contained
plant.
The "Metafilter" is just one example of
this type of pressure clarifying filter, which
is widely used. It is comprised of filter units
built up of separate stainless-steel discs on a
central grooved column. Each disc is 22 mm
in diameter and is flat on one surface, while
it has a raised pattern of about 0.05 to
0.2 mm on the other surface. The rings are
mounted on the column so that filtering
channels are formed between the flat side of
one plate and the raised pattern on the next.
The plates are held together by a screw
thread, the column being mounted vertically
on a base plate over which the pressure
dome is securely bolted (leakage is pre-
vented by a gasket). Filtration is carried
out by precoating the rods with filter aid;
then the product to be filtered is pumped in
under gradually increasing pressure to give a
constant flow rate. Such filters are capable
of producing a bright liquid product and
have a good volume capacity. Because of
their size and design they are relatively easy
to operate, can be cleaned by back-flushing
with water and/or steam, and are almost
ideal for "polishing" liquid flavorings.
Alternately, the filter medium may con-
sist of porous ceramic filter candles of
defined porosity, ranging in size from very
coarse to submicron; they may be made of
tightly wound synthetic fibers on a core,
of sintered stainless steel; or they may be
disc elements constructed of two filter media
discs with a supporting spacer stacked on
a central column to form a compact filter
cartridge. This type is often called a "car-
tridge filter." Many clarifying filters differ-
ing only in detailed design but functionally
similar are available commercially. Most
are fabricated in stainless steel, but some
smaller units are available with glass parts in
contact with the product. All operate in a
similar manner so the selection is often one
of personal choice. It is best that models be
the same throughout a plant to minimize
spare part inventories. Where increased
capacity is needed, two or more may be
operated in parallel, using the same pump
and feed tank with appropriate piping and
valving.
Vacuum Filters
The simplest form of vacuum filter is the
laboratory Buchner funnel consisting of a
wide, almost flat funnel with low cylindrical
sides having a perforated base mounted
over a receiver; a vacuum flask with a side
arm. The filter medium is usually supported
on the perforations and is paper or cloth,
asbestos no longer being available. Very
large Buchner funnels in the range of 10-12
inches diameter are available and ceramic
units called "nutsches" have been avail-
able to about 36 inches diameter. They are
limited to small-scale production.
Just as the filter press is the most widely
used pressure filter, the rotary drum filter is
the most widely used of the vacuum filters.
The rotary drum filter consists of a hori-
zontally mounted metal cylinder, whose
curved surface is perforated and designed to
hold a filter cloth. The drum is mounted
over a slurry tank and can be adjusted so
that a segment of the drum dips into the

1-- - - - - - - - - squeeze rol ler
spray washers - - -o 0
0
FIGURE 11-ll. Rotary drum filter. (Heath 1981)
tank to a predetermined (but often variable)
depth as it rotates. Internally, the drum is
divided into segmented shallow compart-
ments, which permit intermittent applica-
tion of vacuum as the segment becomes
immersed in the slurry. At this point, the
filtrate is drawn into the drum compartment
and is channeled automatically to a receiver.
The filter cake remains on the surface of
the drum. As the segment leaves the slurry
tank, the vacuum is released and the adher-
ing filter cake may be spray washed and hot
air dried prior to the removal of a portion
of the cake by a discharge mechanism.
(See Fig. 11-11). The speed ~f the drum is a
critical operating parameter and is usually
Jess than 1 rpm. Design and capacity cover a
wide range of processing requirements from
units of 1 sq. ft. to 800sq. ft. filtering area.
These can be assembled to operate continu-
ously in-line and can be fitted with many
different types of discharge mechanisms in-
cluding scraper knives, doctor rollers, chain,
string, etc., depending on the product form
required. They are used primarily when the
cake is the desired product.
Flavor Manufacturing 571
Centrifugation
Centrifugation is a method of separating a
solid from a liquid or of two immiscible
liquids of different densities. The centrifuge
is a machine for applying a rotational force
to a mass, the particles of which, being
unrestricted, move away from the center of
rotation. It consists basically of a bowl or
basket capable of being rotated at a high
speed. The axis of rotation may be vertical
or horizontal, depending on the design of
the machine and whether it is intended for
batch or continuous operation. The forces
involved within the centrifuge are related by
Stoke's equation:
F = Mrw2
where F = centrifugal force, M = mass or
density of the substance , r = distance of the
particle from the center of rotation and w =
the angular velocity in rpm. From this, it is
seen that the best separation occurs when:
(a) the density differential between the
materials to be separated is greatest, (b)
the safe operating speed of the centrifuge is
572 Source Book of Flavors
maximum and (c) the diameter of the rotat-
ing bowl or basket is as large as practical.
The following types of centrifuges are
widely used within the flavor industry:
Laboratory Swinging-arm Type
This is usually designed to operate at 2,000-
5,000 rpm, but is only capable of handling
small-size centrifuge tubes. Generally, the
tube capacity is about 25-50ml and only
6-8 pairs of tubes can be accommodated.
Vertical Basket Centrifuge
This is of value in the production of aro-
matic and other fine chemicals where the
desired end product most likely is a solid (or
a solid by-product must be removed from
the desired liquid). The rotating basket may
have solid or perforated walls. If perforated,
a woven wire screen and/or a filter cloth
fitted in a coarse retaining screen is held
in place by expandable rings. The slurry is
fed into the top of the basket, while either
at rest or moving slowly at first and the
solid matter is thrown against the walls of
the rotating bowl. The clear liquid passes
through to the casing from which it is piped.
The solid may be washed in place before
unloading. Where the solids are likely to
form a hard or slimy cake with a high flow
resistance or the particles are very fine, a
solid bowl may be used. In this case, the
slurry is fed continuously into the basket
while it spins, separation is affected and the
clear liquid is removed from the center of
the bowl by a weir, suction or overflowing
the top rim of the basket into the curb. The
machine may be fitted with an unloading
plow, the basket may be supported from the
top or underslung and may have piping, as
noted, to allow washing of the cake before it
is unloaded. It may also be closed to handle
volatile materials.
DeLaval (Type) Clarifier
This is a bowl-type machine in which there
are numerous concentric cones separated
by very narrow spaces. The liquid to be
separated enters down the center shaft and
passes out by rising through the narrow
spaces. Any solid matter is thrown onto the
outer wall of the centrifuge and the clear
liquor passes up the inner annulus of the
cones to a collector. This type of unit
normally does not handle large amounts of
solids, but may be equipped to remove the
solids by flushing and is made by a number
of manufacturers other than DeLaval.
Sharples Bowl (Type) Centrifuge
This consists of a long hollow cylindrical
bowl suspended from a central spindle and
resting within a guiding bearing at its base.
The spindle is usually belt- rather than
direct-driven and operates at 25,000 to
50,000 rpm, depending on the motor used.
The feed mix enters the bowl at the bottom
through an inlet port. For the separation
of liquids, the heavier fraction is thrown to
and moves up the outer wall of the bowl,
whereas the lighter fractions passes upwards
as an inner layer. The separated liquids may
be collected through separate outlets fitted
to the head of the centrifuge. If this machine
is used for clarifying, a set of vanes is inserted
into the bowl; the solid matter then builds
up on the outer wall and the clear liquid
passes up in the center and is collected from
a single outlet in the top. The use of this
type is limited by the bowl capacity and is
better confined to products having only low
solids content.
Horizontal Self-clearing Centrifuge
This device is designed for continuous
in-line operation. It usually embodies a
counter-moving spiral scraper, which con-
tinually clears the solid cake from the other
wall of the spinning basket. It may have
either perforated or solid walls with appro-
priate discharge mechanisms for the liquid
and solid phases. They are not used for
liquid/liquid separations and are more
common in tonnage production.
Emulsification
Although most liquid natural and imitation
(artificial) flavorings for use in food are

required to be clear solutions, there is a
demand for flavoring emulsions in the manu-
facture of soft drinks and bottled beverages
and in a few other instances, as in the feed
to a spray dryer (Woodroof and Phillips
1981; Reineccius 1989). These flavorings are
used where a permanent "cloud" is required
in the end product (Tan and Holmes 1988).
An emulsion is a liquid system comprised of
two immiscrible phases, one of which is
dispersed as minute globules (the dispersed
or internal phase) throughout the other (the
continuous or external) phase. The system is
unstable, but may be rendered relatively
stable by the inclusion of emulsifying agents
(usually less than 3 percent of the total mix)
and by suitable size reduction of the dis-
persed phase. The stability must be suf-
ficient so that the emulsion does not break
or "ring" during the normal shelf life of the
product.
Emulsions may be either (a) oil-in-water
(0/W), in which the oil is present as drop-
lets dispersed evenly throughout the contin-
uous aqueous phase or (b) water-in-oil
(W/0), where the reverse pertains. The
ratio of the dispersed phase to the total
volume is known as the phase volume of the
product. Optimally, this should be 40-60
percent; values greater than 60 percent tend
to be more unstable. An emulsion has the
characteristics of the continuous phase so
that dilution or mixing is generally only
satisfactory with materials compatible with
the external phase.
The theory of emulsions is complex and is
outside the scope of this section. For those
wishing to obtain more detailed informa-
tion, the suppliers of emulsifying agents can
direct the reader to the latest works or they
may see standard works on flavor and food
emulsions (e.g., Arbuckle 1986, Brennan
1986, Dickinson and Stainsby 1988; Tse
1990). Here, only the practical aspects of
emulsification will be considered as they
apply to the production of flavoring emul-
sions for soft drinks, or as a first stage in the
preparation of spray-dried products. Most
flavoring emulsions are oil-in-water, but the
Flavor Manufacturing 573
type of emulsion is determined not only by
the relative phase volumes but by the nature
of the emulsifier used and the method of
preparation.
Emulsions vary considerably in their
physical character, depending primarily
on the size of the internal phase globules.
These may vary from 0.25 to 25 microns
in diameter. Where the globules are larger
than 5 microns, the emulsion is considered
to be "coarse"; below this figure it is a
"fine" emulsion. Considerable energy is
necessary to form a satisfactory emulsion,
although a very coarse product may be
made by simply shaking or stirring the two
phases. Generally, high-speed mechanical
agitation is necessary to achieve a uniform
emulsion having globules within a narrow
size range. For greater stability and smaller
globule size, further vigorous treatment is
required. This involves passing the prime
emulsion through a homogenizer.
Emulsifying Agents
Due to positive interfacial tension between
the two immiscible phases, emulsions are
thermodynamically unstable so that the dis-
persed globules tend to coalesce, leading
to the ultimate breakdown or "cracking"
("breaking" or, if incomplete, "ringing") of
the emulsion. This is reduced by the use of
emulsifying agents or emulgents that are
surface active agents. These act as a barrier
between the phases and reduce the opposing
boundary tensions. In doing so, they stabi-
lize the system. Most common emulsifying
agents have a molecular structure that con-
tains both polar and non-polar groups, and
it is the orientation of these which effect
their emulsifying properties. Emulsifiers
fall into one of four categories, depend-
ing on their polarity and surface active
characteristics:
Anionic
Alkali soaps, metallic soaps, organic soaps,
sulfonated oils, fatty alcohols.
Cationic
Quaternary ammonium salts.
574 Source Book of Flavors
Nonionic
Glyceryl monostearate, sorbitan (20) esters,
polyethylene glycols, polyvinyl alcohol,
cellulose derivatives (CMC), sucrose esters.
Ampholytic
Cationic above pH 9, anionic below pH 5,
nonionic in neutral media.
Note: Regulations concerning the type
and quantity of emulsifying agents have
been promulgated by various regulatory
agencies. Pertinent regulations, such as in
21CFR in the United States, should be con-
sulted. The following discussion ignores any
limitations by regulation.
Many of the emulsifying agents that are
acceptable for use in flavoring manufactur-
ing are of natural origin, including: (a)
vegetable products-gums, carrageenin,
alginates, modified starch, lecithin (soy),
pectin, saponin; (b) animal products-
lanolin, cholesterol, lecithin (egg); and (c)
inorganic minerals-colloidal clays, ben-
tonite. All of these emulsifying agents find
extensive use in the manufacture of pharma-
ceuticals and cosmetics, but only a few are
of practical value in flavorings. For a list-
ing of surface active agents, see Flack
(1976), Brennan (1986), Charalambous and
Doxastakis (1989) or Nightingale (1975).
A term commonly used to characterize
emulsifiers is the hydrophilic-lipophilic
balance (HLB), which indicates the solubil-
ity of the emulsifier in relation to water;
the hydrophilic emulsifier is more soluble in
water and carries oil into the water phase;
the lipophilic emulsifier has the reverse
action. The HLB character is quantified
numerically, ranging from 1 to 13, repre-
senting a range of character from insoluble
to soluble in water.
Emulsion Production
The principal equipment used in the manu-
facture of emulsions range from the simple
laboratory scale (bench mixers, pestle and
mortar) to high-speed mixers, turbine emul-
sifiers, pressure homogenizers, colloid mills
and ultrasonic dispersators (Johnson 1974;
Rees and Pandolfe 1986). These machines
display a wide variety of design and func-
tional capability, the choice being deter-
mined by: (a) the volume of the product to
be handled; (b) the viscosity of the phase
materials and the resultant emulsion; (c) the
need to blend in other constituents; and (d)
temperature considerations. The conditions
pertaining to small-scale manufacture are
rarely directly reproducible on the large
scale and the optimum technique often has
to be established experimentally for any
given production.
The most satisfactory method of prepar-
ing an emulsion is by the gradual addition of
the dispersed phase to the continuous phase
with constant and vigorous agitation. Any
other ingredients are usually dissolved in
the appropriate phase before emulsification.
Additions, particularly to the dispersed
phase, are extremely difficult once an emul-
sion has formed. Success depends on the
gradual addition of the dispersed phase in
small successive quantities so that the con-
tinuous phase is always in large excess. Part
of the external phase may be reserved until
the primary emulsion has been formed; then
this is diluted as required. This general tech-
nique applies equally to the production of
0/W and W/0 emulsions, the emulsifying
agent being incorporated into the appro-
priate phase before mixing.
An alternate method of making 0/W
emulsions consists of first mixing the emul-
sifying agent with the oil phase. Such hydro-
philic emulgents as gum Arabic (acacia),
gum tragacanth, methyl cellulose and
sodium alginate can be mixed to form a
smooth, lump-free dispersion without swell-
ing. When water is added in small quanti-
ties, with good agitation, a uniform aqueous
mucilage is rapidly formed and a stable
emulsion can readily be achieved. This is
known as the "dry-gum" method. In certain
cases, the emulgent/oil suspension may be
added directly to the bulk of the aqueous
phase, again with good agitation. The
former method tends to make a better
primary emulsion, although the latter gives

a good emulsion ready for homogenization.
The factors that affect emulsion stability
include: (a) interphase density; the less the
difference, the more stable the emulsion;
(b) interphase cohesion; minimum is favor-
able; (c) presence of solid matter; (d) tem-
perature ; extremes should be avoided, keep
from freezing; (e) droplet size; the smaller
the globule, the more stable the product;
(f) external phase viscosity, with a highly
viscous external phase being advantageous;
(g) charge of the discontinuous phase; and
(h) interfacial tension, which should be
minimal. Most of these factors are con-
sidered in Stokes' law:
v = velocity of separation
g = acceleration due to gravity (or centri-
fugation)
£1 = density of dispersed phase
£2 = density of continuous phase
11 = viscosity of solution
r = particle radius (dispersed phase)
Unstable emulsions are generally those as-
sociated with unsatisfactory manufacturing
techniques, including but not limited to:
wrong order of mixing, too hasty addition of
the phases, inadequate agitation, incorrect
manipulation, dilution of the concentrated
prime emulsion with the wrong phase, the
excessive use of heat, the choice of the
wrong emulsifier, the presence of dissolved
electrolytes, etc.
The processing technique for the produc-
tion of a citrus emulsion flavoring involves
the following precise stages:
a. Blend all the oils and oil-soluble
flavoring ingredients; add any per-
mitted anti-oxidants.
b. Mix these oils with the weighed gum
arabic (acacia) or gum blend to form a
smooth, totally lump-free cream or
paste.
c. Dissolve any water-soluble ingre-
dients, color, etc., in the water.
Flavor Manufacturing 575
d. Using a suitable high-speed agitator
or turbine emulsifier placed at the
proper height, add the gum/oil cream
to the water phase; maintain stirring
until the prime emulsion is formed.
e. Homogenize at 2,200psi (or ultra-
sonically) to give a globule size of
about 1 micron. Two passes may be
necessary, as the globule size is moni-
tored microscopically or by another
suitable technique.
Homogenization
As described above, it is generally neces-
sary to reduce the globule size by passage
through some form of homogenizer. This
not only reduces the particle size of the
dispersed phase, but also considerably in-
creases its surface area and uniformity. This
contributes significantly to the stabilization
of the resultant emulsion (note the r 2 term
in Stokes Law), but repeate d homogeniza-
tion (often tempting) may result in destabili-
zation and ultimate breaking of the product.
Homogenizers are of three main types:
Valve homogenizers The crude emul-
sion is forced under considerable pressure
through a small spring-loaded valve or
annulus so the emerging high-pressure jet
impinges directly onto the face of a ring set
at right angle to the flow. The impact creates
excellent shear action (See Fig. 11-12).
Rotary colloid mills The crude emul-
sion is fed into the center of a high-speed
rotor and is thrown against the wall of a
stator, having to pass through a gap of about
50 microns. The finer the clearance of this
gap, the smaller the globule size, the smaller
the volume throughout the machine and the
greater the heat genera ted-an important
factor in flavoring emulsion production.
Ultrasonic vibrators The prime emul-
sion is fed, usually by pump, into a tube
containing a transverse blade vibrating with
a frequency of about 30kHz. This induces
cavitation in the product and reduces the
particle size of the dispersed phase very
efficiently. These machines may be used for
continuous in-line emulsification.
 576 Source Book of Flavors

pharmaceutical emulsions and only recently

has been used to produce flavor and cloud
emulsions (Tse 1990) . This equipment
works on the principle of dividing a high-
pressure stream (up to 25,000 psi) into two
parts, passing each part through a fine orifice
(in the micron range) and directing the flows
VAlV E SEA T GA$K£f
VAI.V£ SEAT at each other (Chardonnet , Korstvedt and
VALVE _ _____,
tMPACT RING Siciliano 1985; Washington 1987-see Fig.
VALVE ROO PA(K I NC
VALVE BO D Y - -- ' : 11-13). This creates a tremendous shearing
V ALV E ROD - - - - "
HANDWHEEl SUPPORT
VALVE $PRING _ ___,
action, which provides an exceptionally fine
HANOWHEEI. - -- --" emulsion. Studies by Tse (1990) have shown
that this type of homogenization is superior
Courtesy of Merory Flavors, Inc.
to the other types commonly used in the
FIGURE 11-12. Single stage homogenizing industry.
assembly. (Heath 1981)
Flavoring Emulsions
When formulating flavoring/clouding emul-
Microfluidizer The Microfluidizer™ sions for bottled soft drinks, the specific
was originally designed by the Arthur D. gravity of the dispersed oil phase is of prime
Little Co. , but recently has been taken over importance and is adjusted with a weighing
by the Microfluidics Corp. (Newton, Mass). agent as determined by the Brix value of the
This equipment has been traditionally used finished drink. If the gravity of the oil is
in the pharmaceutical industry to make correct, the finished drink will be stable and

Front View Top View

Priming
VaiYe

Pump

Pump

Outlet
Port Backprassure
Chamber

Outlel
Port

Inlet PI!SSUrt
NOTE: Res.,oir and Cooling Coil not shown. Backpressurt Port Readoul
Chamber Port

FIGURE 11-13. Schematic of the microfluidizer. (Microfluidics Corp., Newport,

Mass.)

TABLE 11-1. Weighing agents for flavor oils used in
emulsions (Heath and Reineccius 1986)
Specific
Ingredient Gravity Legal Status•
Brominated vegetable 1.33 15ppm
oil(BVO)
1.10 lOOppm
Glyceryl abietate
(ester gum)
Sucrose acetate 1.15 10-15ppmb
isobutyrate
Glycerol tribenzoate 1.14-1.2 GMP"
Damar gum 1.05 b
Wood rosin 1.06 b natural and/or artificial flavors, individual
a ppm in finished product.
bNot permitted in the United States, but permitted in some
other countries.
'Good manufacturing practice-total amount of this and other
weighing agents may not exceed 0.5%.
will not "ring" or "sediment" on standing
for long periods. Failure to achieve this
balance invariably results in products dis-
playing these quality faults. For most citrus-
flavored emulsions, the specific gravity of
the oil should be adjusted to between 1.01
and 1.02 for use with sugar-sweetened
beverages or 0.96 to 0.98 for dietetic drinks.
Until 1970, when the use of brominated
vegetable oil (BVO) was restricted to a
maximum of 15 ppm in the finished drink,
this gravity adjustment posed few problems;
now alternative systems have been devel-
oped and the flavoring manufacturers' usage
recommendations must be closely followed
for success (Tan and Holmes 1988; Perotti
1977; Table 11-1). The reader who does
flavor formulation is again advised to con-
sult the regulations of governing bodies for
the current specifications.
For typical working formulations, the
reader is referred to an older formulary by
Memory (1968) without comment as to the
quality of the flavors or to the current avail-
ability or legal status of ingredients. His
book is still available in libraries and is
devoted to formulations. Specifically note
his formulations numbered MF 155, 218,
219, 220, 221, 222, 233, 253 and 261 for a
range of flavor types.
Flavor Manufacturing 577
Spray-dried Flavors
While the subject of spray-dried flavors will
be discussed in a later section on dry flavor
types, they are mentioned here because the
first step in their production is the formation
of an emulsion. They are of the 0/W type,
where the active flavor ingredients are in the
oil phase and the aqueous continuous phase
is a solution or mucilage of the encapsulant,
which also is acting as the emulsifier. The
active flavorants may be compounded
chemicals or natural oils, while the emulsi-
fiers/encapsulants are water-soluble gums
such as gum Arabic (acacia), modified
starches or mixtures of them. The basic
method of production is that already de-
scribed, but specific gravity of the oils may
be of little concern unless the spray-dried
flavor will go into a beverage application.
Otherwise, the requisite time span for emul-
sion stability is hardly ever over 24 hours,
and often just minutes or seconds. The out-
put pressure of a valve homogenizer may
indeed be the input pressure to the nozzle in
a dryer that uses pressure atomization.
Sterilization/Pasteurization
Most flavorings produced by the industry
are microbiologically stable. They will not
support microbial growth. However, in the
absence of preservatives, flavoring products
based on fruits, fruit juices or emulsions
(flavor and cloud) are liable to ferment.
Thus, they require preservation by either
the addition of a bacteriostatic agent (e.g.,
alcohol, propylene glycol or sugar) or heat
treatment. Heat treatment may also be
done in order to inactivate indigenous plant
enzyme systems that would otherwise lead
to flavor deterioration. The protection of
such products after pasteurization or steril-
ization is usually affected by storage in
hermetically sealed containers that must
remain unopened until the product is even-
tually used. Some products not completely
used at once after opening may be stored
under refrigeration for a reasonable time.
578 Source Book of Flavors
The heat treatment necessary to achieve
sterilization varies with the type of organism
present and the heat sensitivity of any
enzyme systems and the flavoring com-
ponents that characterize the product.
Yeasts are destroyed by heating to 60°C
(145°F) for 1-2 minutes, nonsporing acid
tolerant bacteria are destroyed at 65°C
(150°F) for several minutes, spore-forming
bacteria require 85-90°C (190-200°F) and
thermophiles require heating to l20°C
(248°F) for up to 30 minutes. Mold spores
are destroyed at about 80°C (175°F) in 5
minutes. The killing of bacteria and other
microorganisms is a temperature/time rela-
tionship; the higher the temperature, the
less time is needed to achieve sterilization.
In the case of fruit-based flavors and fruit
juices, this is strictly limited by damage to
the odor, flavor and color that are asso-
ciated with excessive heat treatment.
Three methods of heat sterilization are
currently used in fruit product processing:
Pasteurization
The product is heated, before or after filling
into final containers, at 65-85°C (150-
1800F) for periods up to 30 minutes.
Flash Pasteurization
The product is passed through a tube or
plate heat exchanger and raised to about
95°C (200°F) for 1-3 minutes before filling
into sterile containers.
Ultra-high Temperature (UHT) Sterilization
The liquid product is heated to tempera-
tures in excess of 135°C (306°F) for periods
of only a few seconds, rapidly cooled and
filled aseptically into sterile containers.
Under investigation and not widely
accepted as yet are ultraviolet irradiation
and irradiation by gamma rays. These
involve the passage of thin films of the liquid
(to obtain penetration of the rays) past the
source of the irradiation.
The method of choice depends on the
nature of the end product to be inactivated
or sterilized. In the case of clear juice and
juice products, sterilization by filtration
through sintered glass plates of the correct
porosity is widely used. Clarifying-type
candle filters with fine enough porosity
are also available. Whatever procedure is
adopted, it is necessary to employ the lowest
effective temperature/time ratio to limit
the sensory degradation of the product to
a minimum. Ideally, flash pasteurization
followed by aseptic filling gives the best
chance to maintain the full fresh character-
istics of the fruit. UHT has its advantages,
but is mostly applied to a very fluid product
such as milk, which is so obviously affected
by heating. The flow of viscous products is
much more difficult to control and the im-
provement of flavor profile is not so obvious.
It is important to have adequate laboratory
bacteriological control to assure that the
sterilization has been properly carried out.
Dry Flavor Production
The dehydration of fruit and vegetables is
widely used as a method of preservation.
Although the flavor industry is not normally
directly involved in this specialized form of
processing, it does make use of dehydrated
products (e.g., dehydrated onion and garlic
powders, herbs and spices) in blended
seasonings and as the starting material for
the solvent extraction (alcohol or other
organic solvents) of fresh plant materials
that would be difficult to handle. The
demand for an extract might come at a time
of year when fresh material would not be
in season as well. This form of large-scale
dehydration lies outside the scope of this
section and the reader is once again referred
to the literature, including Holdsworth
(1986), Considine and Considine (1989), Van
Arsdel (1973), and Anon (1989c; 1989d).
Instead, this section of this chapter will
provide a broad overview of drying as used
in the flavor industry. The following section
of this chapter will discuss, in some detail,
the processes for making dry flavorings.
 Flavor Manufacturing 579

Drying transfer from vapor to liquid equals the

In the production of aromatic chemicals and latent heat of evaporation of the liquid.
in some of the other operations, such as the
recovery of alcohol or solvents from spent Dryers
extracted plant materials (marc), drying is There are four types of dryers used to pro-
an essential stage of processing involving duce dry solids from a wet feed, although
various techniques based on direct, indirect differences exist in equipment within each
or radiant heat dryers. Whatever the method type: (a) direct heat dryers, in which the
used to achieve a dry product, all involve heat transfer is directly between the wet
the evaporation of the solvent by heat. In material and the hot gases. The vapors are
most cases, this is water, but in others it removed from the drying area in the hot gas
may be an organic solvent that must be stream; (b) indirect heat dryers, whose heat
recovered. For optimum drying conditions, for drying is transferred to the wet material
it is necessary to regulate three directly through retaining walls, the vapor being
related conditions: (a) the movement of the removed independently; (c) radiant heat
solvent from within the material to the sur- dryers, which depend on the generation,
face; (b) the evaporation of the solvent from transmission and absorption of infrared rays;
the product surface; and (c) the removal of and (d) dielectric heat dryers, whose heat is
the solvent from the system. Not normally generated by placing the wet material in
requiring regulation during the process, but a high-frequency electric field. Of course,
at the end of it, is a means to remove the dry combinations of these may be used.
product from the system, whether it is waste
The operation of a dryer is dictated by
(marc) or the desired residue. Drying equip-
the need to: (a) conserve (heat) energy, (b)
ment is designed and operated to achieve a optimize working space, (c) minimize labor
balance among these stages and also to take and (d) limit (minimize) air pollution. The
into account the volume of air required, the latter is of particular concern in the drying
relative humidity of the incoming air and the
of highly aromatic materials and in the pro-
velocity of air through the drying chamber.
duction of spray-dried flavorings, where
These, in turn, dictate the amount of heat
such losses must be reduced to the absolute
energy to be provided to achieve optimum minimum, not only for economic reasons
drying conditions. but also to prevent environmental pollution.
Both direct and indirect heat dryers may be
Factors Affecting Drying designed for batch or continuous operation.
Four basic physical factors must be con- The choice of the actual plant requirement
trolled for efficient drying and the operating is determined by the physicochemical char-
conditions are usually displayed graphically, acteristics of the wet start and dry end pro-
employing the following terms: (a) absolute ducts that dictate the temperature and time
humidity, expressed as weight of water parameters as well as the heat transfer rate.
present per unit volume of moist air; (b) the The amount to be processed in a given time
relative humidity, which is the ratio of the period must also be taken into account for
actual vapor pressure to the saturated vapor economic reasons, weighing the one-time
pressure at the same temperature expressed cost of equipment versus the continuing
as a percentage; (c) the dew point, which cost of labor, for instance. The optimum
is the temperature at which the saturated handling conditions are influenced to a large
vapor pressure and the actual vapor pres- extent by the quantity of material to be
sure are equal; and (d) the wet-bulb tem- dried, the economic throughput rate, opera-
perature, which is the dynamic adiabatic tional reliability and quality maintenance.
saturation temperature at which the heat Direct heat dryers Direct or convec-
580 Source Book of Flavors

tional dryers use heated gases, which are in
direct contact with the material to be dried.
The process is carried out in an oven whose
design is dictated by whether it is for batch
or continuous operation. The following
types are of particular interest to the food
and flavor industries: tray or oven dryers,
vacuum oven dryers, tunnel dryers, fluid-
bed dryers, rotary dryers and spray dryers.
Tray or Shelf Dryers-The process of
tray-drying consists of exposing the wet
materials in thin layers on shallow trays,
which are arranged in tiers on shelves fitted
on the oven sides or on mobile trolleys.
There are many such ovens in use, varying
in design and capacity depending on the
heat source. The trays may be fabricated of
wire mesh rather than with solid metal sheet
bottoms. Such ovens may be operated in
several ways:
a. Simple open system heated by steam
coils on the bottom or along the
sides of the oven, or the entire/partial
area of the walls being jacketed, air
circulation being by convection or
by a small fan mounted within the
oven. Heat may be provided by elec-
trical units. Such ovens are generally
limited to bench-scale or small-scale
production.
b. Thermostatically controlled air flow
with heat as provided in (a) above.
These, too, are generally bench or
small-scale models, with the air flow
being maintained by internal fans.
c. Vacuum ovens, in which the heat is
provided by steam coils or electrically.
d. Forced air circulation ovens, in which
the hot air flow is directed and con-
trolled, the moisture-laden air being

Relative humidity %
100 85

...> H2 - - - - - - - -
:2 -......--•
.....
E
;;;J E ' IF
.t::.
' ......I
5
____ ___
c' ID
] ,
'- '-..
...;.
........
I
- ----
<(

IB
I

T1 T2
Temperature

FIGURE 11-14. Humidity graph for tray dryer. (Heath 1981)


removed quickly from the drying
chamber.
In all but the simplest of ovens, the in-
ternal layout forces the hot air to flow over
the trays successively, being reheated as it
progresses. This allows the air to carry
more moisture without excessive heating of
the material being dried. Recycling of the
heated air is considerably more effective
than merely allowing the air to pass directly
out of the system. This can be seen from the
humidity chart (Fig. 11-14) for such an oven.
Incoming air of humidity H 1 and tempera-
ture T 1 is heated to T2 (B) and passes over
the first tray. As it does so, it picks up water
to about 85 percent relative humidity and
changes state in accordance with the adia-
batic saturation line BC. At this point, it
is reheated to T2 so that the state follows
the line CD. Passage over the second tray
repeats this operation, the state changing
along DE, then to F and FG. To achieve
the same water pickup in one pass, the air
would have to be heated to T3 . The resulting
oven conditions would more likely result in
heat damage to the product.
Vacuum Oven Dryer-Vacuum oven
drying is also of some importance in the
production of flavoring products based on
natural extracts or fruit juices. In such cases,
exposure of the concentrated fluid extract
or fruit product could lead to excessive
degradation or volatile loss if the product
were exposed to excessive heat. The oven
layout is similar to that already described,
but the tray support shelves are formed by
steam coils or plates and the chamber is
designed to withstand evacuation. This uses
much less heat than atmospheric ovens and
so permits the product to be dried at a lower
temperature. Some disadvantages to the
use of vacuum ovens are: (a) moist extract
swells and may overflow the trays, causing
local overheating; (b) the dried product is a
porous sponge that needs grinding before
use; (c) the product volatiles may be lost via
the vacuum pump system; and (d) the whole
product is subject to heating for the period
Flavor Manufacturing 581
necessary to complete the total drying pro-
cess. This means that the dry layers in
contact with the heating surface may get
considerably overheated.
Vacuum drying is applied to citrus juices,
to various dehydrated fruits and to flavoring
extracts that are heat sensitive. The lower
drying temperatures and reduced drying
cycle are less likely to produce "browning"
of sugars and loss of volatile constituents.
Tunnel Dryers-These are modified tray
ovens, which differ only in the shape of the
drying chamber and the method of holding
the wet material. In all cases, the hot air
enters at one end of the system and leaves at
the other. The dryer consists of a tunnel-like
chamber, typically 20-30 ft. long, 5 ft. high
and 3ft. wide, into which the wet product is
loaded on either trolleys (carts) or on a
conveyor belt. In all such dryers the wet
product moves through the dryer; the forced
air flow may be parallel, counter or across
the line of movement. The hot air system
may be operated adiabatically without the
further addition of heat to the hot gases, or
it may be reheated by steam coils or electric
grids in zones along the length of the tunnels.
There may be sections of coil or plates
under a metal belt, but not under a rubber
or plastic belt.
Conveyor or tunnel dryers are best suited
to large-scale drying of a single commodity
(or seldom-changed runs of several com-
modities), rather than in cases where the
wet material is discontinuous; they may be
used in semi-continuous processes where
one batch of a preceding step is followed
closely in time by a second batch (Anon
1977b).
Fluidized-bed or through-circulation
dryers-In these dryers, the wet material is
loaded onto a mesh screen and the hot gases
forced upward or downward through the
product. Numerous designs are available to
achieve this. One such machine conveys the
hot gases through a spiral center tube with
ports at intervals. The wet product is intro-
duced at the bottom and moves slowly up a
spiral conveyor; as it does so, the hot gases
582 Source Book of Flavors
air
filter
FIGURE 11-15.
are forced through the product mat. Some
batch dryers simply force hot gas upward
through the bed of material on the mesh
screen, causing it to be tumbled and thus
getting more intimate contact for rapid
drying. Fluidized bed drying is most suitable
for granular products that have a particle
size sufficiently large to float on the hot
air cushion and not drop through the aper-
tures of the supporting mesh carrier. They
are also adaptable to agglomeration of par-
ticles and coating of particles with another
material.
Spray dryers-Spray drying is a well-
established unit operation, which has been
used industrially in many ways for several
decades (Masters 1979) (see Fig. 11-15).
Spray dryers are designed to handle wet
material in the form of a solution, slurry or
emulsion. Drying is achieved by spraying
the feed liquor as minute droplets into a
stream of hot air or other gases. This pro-
duces a very large contact surface, which
results in a high rate of liquid evaporation.
The short drying time, usually only 5 to
10 seconds [some manufacturers claim less
pump electric
heater
Spray dryer. (Heath 1981)
than 1 second] keeps the temperature of the
material to be dried low relative to that of
the drying gases. The heat of evaporation
also cools the drying particle. The drying
material never exceeds the exit air tempera-
ture of the dryer and only approaches exit
air temperature as the powder exits the
dryer. Therefore, heat damage to the dried
material is minimal as long as it is efficiently
removed from the hot gas stream and over-
heating is avoided.
Spray drying is particularly applicable
to the drying of materials that are heat-sen-
sitive, since they are less likely to discolor,
oxidize or suffer aromatic loss or degrada-
tion than in some of the types of dryers
discussed. It is also a very effective method
of producing flavorings encapsulated in
natural gums, modified starches or mixtures
of them. The dried material is recovered as
a finely divided powder (generally 10 to 60
micrometers in diameter), comprising fairly
uniform spherical or crenelated spherical
shape in a narrow range of particle sizes
with characteristic physical properties and
bulk density. Particle size can be influenced

by adjusting the size of the droplets fed into
the gas stream.
The process of spray drying involves
several stages: (a) the preparation of the
solution, slurry or emulsion to be dried; (b)
the atomization of this liquid feed material
as it enters the dryer chamber; (c) the
regulation of temperature, volume and
velocity of the drying gases; and (d) the
removal and recovery of the dried product.
It is also possible (but costly) in critical cases
to remove moisture from the inlet air before
it is heated in order to improve the efficiency
of drying. It is imperative to filter the inlet
air to remove any particulates that would
contaminate the product.
Atomization
Atomization is an important factor in the
spray-drying operation, the aim being to
produce a high surface area to mass ratio in
the liquid phase. Three different systems
are used to achieve this: high-pressure cen-
trifugal nozzles, two fluid nozzles and high-
speed centrifugal discs.
Atomization by high-pressure nozzles is
effected by forcing the liquid feed under
high pressure (400-10,000 lb/in. 2 ) through a
small orifice. A spinning motion is produced
in a "spinning chamber" within the nozzle
by suitably machined grooves and by the
jets being set at an angle to the orifice axis.
At these pressures, the nozzle is subjected
to considerable wear, which is exacerbated
by the presence of any solid material in
the feed. This demands a nozzle made of
extremely hard alloy and/or its regular
replacement if good atomization is to be
maintained. The spray pattern is deter-
mined by the pressure used, the size of the
jet orifice and the internal design of the
nozzle. Many manufacturers prefer this type
of nozzle in their spray drying operations to
the exclusion of other types.
Designs are available that utilize a ceramic
swirl chamber, which produces a free vortex
spray pattern. In such devices, the internal
friction is minimized, allowing operation at
a lower pressure. The mist produced is dried
Flavor Manufacturing 583
by either a concurrent or countercurrent
flow of hot gases. Many driers of small to
moderate size use single fluid nozzles.
Atomization by two fluid nozzles is
obtained by means of a high-pressure jet of
air, inert gas or steam carrying the slow-
moving feed liquor through the nozzle into
the drying chamber. The two co-axial
streams combine to form a hollow cone-
shaped mist. This is rapidly dried by the
hot air, which flows either concurrent or
countercurrent to the incoming jet. The
system is simple to operate and is effective
in small-scale dryers.
High-speed centrifugal discs depend on
the production of a thin sheet of feed liquor,
which is flung from the periphery of a disc
rotating at high speed (>20,000rpm) in the
drying chamber. The discs are of special
design to break up the sheet into uniform
droplets. The feed liquor may be introduced
directly onto the center of the disc or through
rotating vanes within the disc, or through
low-pressure nozzles rotating co-axially and
parallel to the discs. Disc atomizers are
generally considered to be more versatile
than jet nozzles, can accept a wider range of
feed liquor viscosity characteristics and are
capable of operating over a wider range of
feed rates and disc speeds.
The Drying Stage
The drying chamber design is aimed at:
(a) achieving an intimate mixing of the
atomized spray and the drying gases; (b)
removing the moist gases and dry product
from the hot drying chamber; (c) preventing
the buildup of dried product on the walls
and elsewhere within the chamber; and
(d) simplicity to enable ready cleaning and
hygienic operation. Dryers are of three
main types, although there are many
purpose-designed machines. The type
depends on the direction of flow of the hot
drying gases:
Cocurrent dryers (Fig. 11-16) The feed
liquor is atomized into a stream of hot gases
at its inlet temperature. The particles are
dried and remain in the air stream, cooling
584 Source Book of Flavors

moist air
plus
product

atomizer

moist air
plus product
~---

hot air input

FIGURE 11-16. Cocurrent flow. (Heath 1981)
FIGURE 11-17. Countercurrent dryers. (Heath
1981)

as the gases cool by the evaporation of

water. This air flow pattern can be used with
either nozzles or centrifugal atomizers.
Drying capacity is further improved by im- hot air
input
parting a cyclonic spin to the circulation
within the chamber by positioning the air
inlet at an angle. These dryers have a
tendency to build up dry powdered product
at the base of the chamber and an air-sweep
is sometimes incorporated to clear this
material. Powder draw-off may be at the
base and from a cyclone (see below). The
shape of nozzle-atomized dryers tends to be
tall and thin; disc atomizers are somewhat
shorter and squatter because of the spray
patterns in order to prevent impingement moist air plus product

on the upper walls. They may have flat or

coneshaped bottoms.
Countercurrent dryers (Fig. 11-17) The
hot air enters at the bottom of the drying
chamber and the atomized spray at the top.
As the droplets first encounter partially
cooled moist air, the drying rate is reduced
and the dried particle density increased.
Agglomeration of the particles is more
likely under these conditions, and a buildup
of dried material is very common in this
FIGURE 11-18. Mixed current flow. (Heath 1981)
form of dryer when fitted with a disc
atomizer.
Mixed flow dryers (Fig. 11-18) There are
numerous designs of dryers combining co-
and counter-current air circulation. Most
are designed to give good turbulence in the
drying chamber. The size and shape of the

drying chamber are determined by the
atomizer and air input patterns adopted.
Dryers are available in sizes ranging from
30 to 48 inches in diameter for laboratory
or pilot use, which are capable of making
4-10 lbs. of dry product/hr. to units of 36 to
40 feet in diameter and capable of producing
500 to 600 lbs./hr. of flavoring.
Dried Product Recovery
The great advantage of spray drying is that
evaporation is rapid and the drying rate
remains constant so long as there is free
moisture on the droplet surface. Under
these circumstances, the particle tempera-
ture does not exceed the wet-bulb tempera-
ture of the air in contact with the particles
and, in consequence, heat sensitive materials
are less likely to be degraded. Once the
particles are dry, their temperature rises
significantly and it is then essential that they
be removed from the hot drying chambers
as rapidly as possible. In most spray dryers,
the powder is entrained in the drying gases
and moves in the main air stream into a
cyclone separator set apart from the drying
chamber. Any powder that settles in the
drying chamber may be removed by rotary
air-lock valves, by suction or other means,
and combined with that collected via
cyclone. Many units are equipped with
additional cyclone(s) to recover finer par-
ticles, which may have come through the
first and/or with secondary sources of cold
air to reduce the temperature of the exhaust
gases after drying is complete, and hence
reduce the temperature of the powder.
Each cyclone is equipped with a means of
emptying it continuously or periodically,
and the gases may finally be put through a
bag filter or wet scrubber to prevent con-
tamination of the atmosphere and/or to
collect the last traces of valuable product.
Each batch of powder may display some
degree of heterogenatiety in particle size
when first collected. It is desirable to bulk
each batch in a suitable blender, often a
simple ribbon mixer, before sampling for
critical quality appraisal.
Flavor Manufacturing 585
Spray-Dried Flavors
These constitute an important group of
flavorings, in which the aromatics are en-
capsulated or "sealed" in a protective casing
of gum Arabic (acacia), modified starch
or combinations of them. The method was
serendipitously discovered by Revie et al. in
1932 at A. Boake Roberts & Co. Ltd.,
which pioneered its commercialization
(Bush Boake Allen Pat. 1,327,761). The
technique is now very widely used in the
flavor industry, accounting for well over 90
percent of the dry flavoring production. This
process has achieved such a large market
share for a number of reasons. They include
availability of equipment, low cost, wide
variety of carriers, tradition, suitability of
handling a variety of flavorings, good pro-
tection to flavorings, etc. The spray-drying
process ensures that the full aromatic profile
desired (with appropriate adjustments to
the oils in the emulsion, as there will be
some loss of ingredients) is retained and,
indeed, it allows the use of constituents
that could not readily be incorporated into
traditional liquid flavorings. The initial
sensory impact of spray-dried flavorings is
normally dull, but once wetted the encap-
sulated aromatics are freed, and the full
aroma and flavor is achieved. However, it is
possible to spray dry a flavoring with so
much oil that some is not fully encapsulated
and remains on the surface of the particle,
providing a stronger initial sensory percep-
tion of the flavor.
It is also possible to spray dry volatile
chemicals that are soluble in water with a
carrier and encapsulate a certain propor-
tion of that chemical. General Foods has
numerous patented processes in which
acetaldehyde, boiling at 20.6°C, is spray
dried in a slurry of mannitol (or other
carriers) at carefully controlled tempera-
tures to give products retaining at least 2-3
percent acetaldehyde, useful in a number of
dry flavoring mixes.
The formulation of spray-dried flavorings
poses certain problems not encountered in
the making of the equivalent liquid product.
586 Source Book of Flavors
The first stage of manufacture consists of
making an O!W emulsion, the flavoring
components being the dispersed phase,
water being the continuous phase with the
encapsulant dissolved in it and acting as
the emulsifier. If gum acacia is used as the
encapsulant, the pH of the initial mucilage
may be as low as 4.2; this may affect certain
aromatic constituents. During the actual
drying operation the flavor droplets are
heated in the presence of water and before
encapsulation takes place, some steam and/
or fractional distillation takes place. The
extent of this and its effect on the final
flavoring is determined by the different
vapor pressures, boiling points, concentra-
tions and water solubilities of the aromatic
chemicals present (Leahy et al. 1983). For
this reason, one cannot merely emulsify and
spray dry a given flavoring composition and
expect to get the same flavor profile in the
resultant dry powder flavor. This means
that the composition of the flavoring com-
position intended for spray drying must
be reformulated to take into account the
expected losses and changes in the flavor
balance.
Kapp (1965) quotes two formulations for
an artificial cherry flavor, one for the normal
liquid flavor and the other intended for
spray drying. Four points of difference are
noted, which apply to these and to similar
formulations: (a) alcoholic essences and
extracts are replaced by the equivalent solid
extract or oleoresin; (b) acetals are replaced
by their constituent aldehydes and alcohols;
(c) glycerine or propylene glycol is entirely
removed, as these solvents are humectants
and cannot be spray-dried effectively; and
(d) the proportion of many lower-boiling
components has to be increased to counter
their physical loss from the mixture during
the drying. This balancing of a formula to
give liquid and spray-dried flavorings having
the same flavor profile is not easy, nor is
it always feasible. Flavorists are generally
able to make the basic modifications for a
reasonable match based on their experience,
but in many cases the exact formulation and
drying conditions can only be established by
trial and error; scaling up from laboratory
dryers to full plant size may require additional
modifications. It would be quite wrong to
assume that an exactly equivalent spray-dried
flavoring is always immediately available-
reformulation and trial dryings can be very
time-consuming and costly.
The flavorist is aided by the use of sophis-
ticated analytical equipment, such as gas
chromatography to obtain profiles of the
original oils prior to emulsification and spray
drying for comparison with the oils isolated
from the spray-dried end product. These
latter oils are obtained by use of a Clevenger
Trap and the methodology described in
FCC III (or a roughly similar method) to
effectively steam distill them from a sample
of product dissolved in water. After allow-
ance is made for whatever constituents
might be dissolved in the water, the propor-
tions of each constituent are easily checked
against the originaL After corrections have
been made to the formulation and a sample
is emulsified and spray dried, the procedure
is repeated. More than one adjusting ex-
periment may be needed. Organoleptic
evaluation follows after each adjustment has
been completed. It is also possible to extract
unencapsulated oils adsorbed on the outer
surface of the spray-dried product by general
methods of solvent extraction and weighing
the dried encapsulated powder, and/or to
recover the oils encapsulated just to meas-
ure the amount present as a quality control
procedure (Anandaraman and Reineccius
1987). (This process is continued in Part 2 of
this chapter.)
Indirect dryers The design principle of
indirect dryers is that the heating source
is separate from the air used to remove the
evaporating water or solvent. This is an
advantage in that the air stream does not
have to be heated and, so long as the
volume flow is adequate, saturation con-
ditions do not develop and drying proceeds
well. This represents a considerable savings
in heat energy, therefore cost. Drying is
achieved in several different ways, de-

pending on whether the machine is for batch
or continuous operation. Batch indirect
dryers include the following types: agitated
pan dryers, used at atmospheric pressure or
under vacuum. These are very versatile and
can handle almost any form of wet material;
freeze dryers, in which the material is frozen
and the water removed by sublimation
under very high vacuum; agitator/rotary
dryers; and vacuum tray dryers (these
have already been described). For continu-
ous processing, the plant facilities include
cylinder dryers, drum dryers, screw-con-
veyor dryers (which are of value as desol-
ventizers), steam-tube rotary dryers, and
vibrating tray dryers. The specific designs
reflect a wide range of applications and,
once again, reference should be made to the
manufacturer's engineering literature for
further details. Some dryers are used more
for individual chemical product. Of the
above dryers, two are of particular interest
for use in food and flavor production.
Freeze dryers-This is a technique for
removing moisture from wet materials by
sublimation. It involves freezing the wet
material at atmospheric pressure, followed
by transforming the ice directly into vapor
that is removed from the system, which is
under a vacuum of 4.6 Torr (sometimes less,
depending on the volatility of the substrate).
Sufficient heat is applied to overcome the
latent heat of vaporization of the ice. The
history and process technology of freeze
drying has been well described by Anon
(1986) and Anon (1989a). The method is
not used much in flavor manufacture (due to
cost considerations), although many pro-
ducts could benefit by this method of drying.
It is widely used in the production of instant
coffee and tea products, which have a finer
aroma and flavor profile than those dried by
other means. Orange and grapefruit juice
have been "dried" by this method, which is
to say concentrated to the point where they
can be reconstituted to the equivalent fresh
juice by the addition of three to five volumes
of water.
Drum dryers-These are particularly
Flavor Manufacturing 587
useful for drying slurries and solutions of
materials that are either difficult to crystal-
lize or are heat sensitive and so require
minimal contact with hot surfaces (note that
there is considerably greater heat, however,
than in spray drying). The short time/high
temperature conditions encountered have
definite advantages, and the technique is
successfully applied commercially to the de-
hydration of mashed potato flakes, several
aromatic vegetable products and some fruits.
Normally, a drum dryer comprises one or
more (usually two) horizontally mounted
heavy steel (or alloy) cylinders heated inter-
nally by high-pressure steam. The liquid
to be dried is fed onto the heated surface
(through perforated pipes parallel to the
surface, or through nozzles) where it forms
a thin film. The feed rate is coordinated with
the rotational rate so that drying is complete
by the time the circumference rotates as far
as a doctor blade, which lifts it off as a solid
sheet or flakes, depending on the nature of
the product and the configuration of the
blade mechanism. The entire dryer may be
enclosed and operated under vacuum to
reduce the temperature needed to dry the
material. With a single drum unit, potato
flakes can be dried from a slurry containing
80 percent water to flakes containing 6-7
percent moisture in only 20 seconds. To
prevent excessive heating of the feed liquid
and of the dried solids, the feed rate, and
drum temperature and rotation time must
be carefully controlled. The steam require-
ment is in the order of 1.25-1.3lbs. of
steam/pound of water evaporated, which
makes drum drying a comparatively inex-
pensive operation.
Radiant heat dryers In the flavor in-
dustry, radiant heat dryers are not widely
used outside of the laboratory, where their
value lies as a ready means of determining
moisture contents by exposing a weighed
quantity of product to infrared radiation.
The product is spread in a thin layer directly
onto the balance pan designed to read
directly the loss in weight in a configuration
intended to reduce the labor and time
588 Source Book of Flavors
required to weigh into a Petri dish, expose
to radiation to dry, reweigh and dry again,
until no further weight loss is found.
Microwave dryers Microwave drying
for commercial use is more or less experi-
mental, although the relatively high cost
is a detriment. The method has several
advantages that may override the cost dis-
advantage, for some products at least.
Microwave drying involves: (a) rapid gener-
ation of heat and instant controllability; (b)
heat generation throughout the mass of wet
product, the power absorption being deter-
mined by the moisture content; (c) uni-
formity of drying throughout the mass (if it
can be agitated to ensure even wave dis-
tribution in the unit); and (d) very high
thermal efficiency.
Coacervation
The technology for the production of
capsules made by the application of thin
polymeric coatings to very small particles of
solids or droplets of liquids, solutions or
dispersions was largely pioneered by the
National Cash Register Company, which
owns the majority of patents for their manu-
facture and application. "NCR paper" as
it is generically called refers not to the
company acronym, but refers to "No
(a) mixing of the three
phase system
& =continuous liquid phase
• = core material
0 = coating phase
FIGURE 11-19. Stages of microencapsulation by coacervation. (Heath 1981)
Carbon Required" in the particular appli-
cation where the process (or a similar one) is
used by other companies. While the tech-
niques are reliable and the microcapsules
made by coacervation have many com-
mercial applications other than in replacing
carbon paper (e.g., time-release drugs,
"scratch-and-sniff" perfume samples, etc.),
a very limited volume of flavorings is pro-
duced by this technique. The choice of the
release mechanism is usually limited by the
intended application of the end product.
However, there are specific uses that make
its inclusion here important.
Basically, the technology involves: (a)
the formation of three immiscible phases
comprising the continuous phase, the mate-
rial to be encapsulated (the "core" material)
and the coating material phase (Thies 1987).
These undergo carefully controlled mixing
to ensure the correct uniform deposition of
the capsule wall. In the case of flavorings,
the materials suitable as encapsulants are
strictly limited by food additive regulations
and, in most cases, only gelatin is used for
this purpose; (b) the deposition of the
capsule wall around the core material,
which involves interfacial sorption of the
hydrophilic phase on the droplets of the
core material. The addition of an electrolyte
(b) deposition of the (c) shrinkage and
liquid coating solidification of
the liquid coating
to form the
microcapsules

to the system causes the precipitation of the
colloid by neutralizing its charge and by
removing the enveloping water layers. This
stage is carried out to effect the coalescence
of the liquid droplets to form a liquid coat-
ing on the core material; (c) solidification
and shrinkage of the liquid coating to form
the solid microcapsules by desolvation or
thermal cross-linking. These stages are illus-
trated in Fig. 11-19.
Manufacturing Technique
As the first stage of manufacture of micro-
capsules, the gelatin is dissolved as a soluble
in water in a jacketed stainless-steel tank
fitted with a variable-speed emulsifier or
mixer. The pre blended aromatic core mate-
rial (i.e., the concentrated flavoring base),
which is normally immiscible with water, is
added to the gelatin solution in a steady
stream with vigorous stirring. The mixing is
continued until a smooth uniform emulsion
is formed. Any solid ingredients should be
similarly added and a fine dispersion pro-
duced by vigorous mechanical agitation.
When the emulsification is satisfactory,
coacervation is induced; the electrical
balance of the system is altered to cause the
coating material to come out of the solution
and form a liquid wall around the emulsified
flavoring droplets or dispersed solid parti-
cles. The nature of the capsule wall may be
considerably modified at this stage and its
flexibility and ultimate permeability can
be controlled by certain additives (e.g.,
inorganic salts, gum acacia, synthetic
copolymers, etc.), which affect the electrical
balance between the phases. At this stage,
the capsule wall is still liquid and must be
hardened to form the final solid microcap-
sule. For flavorings, this is done by chilling
the mix or by methods of desolvation, de-
pending on the characteristics desired in the
final end product. Hardening of the capsule
walls is a particular problem when working
with food ingredients vs. other non-food
applications. The best capsules are made by
cross-linking the gelatin with glutaralde-
Flavor Manufacturing 589
hyde. This is undesirable due to toxicity
problems.
The amount of coating relative to the
core material can be controlled, thus de-
termining the flavor strength of the end
product. Usually, this lies between 10 to 30
percent of the total dry weight. The de-
posited microcapsules may be left in suspen-
sion, but more often are recovered from the
mix liquor by any of the usual drying opera-
tions to produce the flavoring in a dry
powder form.
Organoleptic testing of these products
has demonstrated their stability and, in
many cases, their superiority of flavor pro-
file. Release of the encapsulated flavor is
achieved by physical rupture of the capsule
wall, by heat or dissolution in water, de-
pending on its nature and end use. Micro-
encapsulation of aromatic materials has
tended to be limited to the encapsulation of
expensive fragrances as the advantages of
the technique do not warrant the consider-
ably increased cost over normal spray drying
or other alternative methods of producing
encapsulated dry powder flavorings. (See
Thies 1987 or Dziezak 1988 for reviews of
food product ingredients made by various
forms of encapsulation.)
DRY MIXING AND BLENDING
The intimate mixing of powders is an essen-
tial unit operation in almost all branches of
the food industry and flavorings are no ex-
ception. With the increase in convenience
products proceeding rapidly, the "dry-mix"
is now commonplace and may even be
"microwavable." This has led to an increas-
ing demand for dry flavorings, processed
spice seasonings, dustings, etc. In addition,
many plant operations call for the preblend-
ing of dry materials as a stage in the manu-
facturing process. Variations, which often
occur in manufacturing, can frequently be
controlled or regularized by batch blending
to yield a uniform and homogenous prod-
uct. Superficially, the blending of solid
particles would appear to be a simple opera-
590 Source Book of Flavors
tion and thus has been treated in an em-
pirical manner since antiquity. In fact, it is
now recognized that powder blending is a
complex engineering science coupled with
a considerable degree of skill and art. It
demands an appreciation of the nature of
solids and how they behave when mixed, the
particle mechanics involved in creating uni-
formity, the limits of blending that can be
achieved in any given system, and the design
and versatility of the plant necessary to
make a satisfactory end product. Merely
loading dry components into any mixer,
running it for a period and discharging the
product (as so often is done for many years!)
is usually totally inadequate for the produc-
tion of consistently uniform powder blends.
Under ideal conditions, the degree of mix-
ing can be calculated from the simplified
equation:
cr=~
where X and Y are the percentage propor-
tions of the minor and major constituents,
and n is the number of particles in the
sample taken. More complex relationships
have been advanced and most mixtures con-
sist of many more than two components.
Supplementary to the mixing of dry
solids is the need to blend small quantities of
liquid or semisolid materials with a much
larger quantity of dry base. The operation is
widely used in food processing and will be
discussed separately. Although related to
"simple" mixing, it poses several problems
of plant design and technique. A product
made in this manner that was virtually a
tonnage item for many years was "vanilla
sugar" -natural or artificial vanilla extract
coated on cane sugar or dextrose.
Dry Powder Blending
The mixing of ingredients of varying particle
size and in varying proportions to produce
either intermediate or final products is one
of the most common operations in flavor
manufacture (Fig. 11-20). Two factors
directly influence the optimum mixing con-
ditions: mixer characteristics and the physi-
cal characteristics of the dry ingredients.
The ease with which different substances
blend to produce a uniform mix varies con-
siderably in these two respects. Resistance
to flow is what distinguishes solids from
liquids and gases. It is the size and shape of
the particles relative to one another that
contributes most to the flow characteristics
and the way in which they must be handled
to obtain a uniform mix. Particle size is
altered by fragmentation and agglomera-
tion, both of which may occur during the
mixing operation. The size range may be
from 1 micron upward, but more important
than the nominal particle size is the range of
sizes in any given batch. Large and small
particles do not mix readily and tend to
segregate when agitated, depending on the
relative proportions present, the density dif-
ferential and the presence of electrostatic
charges. The finer material tends to sink and
impact below the larger particles that ride to
the surface. Under certain conditions the
reverse happens, and the fines tend to "dust
out." It is not unusual for this sort of
phenomenon to take place from the vibra-
tion and jostling that packages of finished
end product receive in shipment from the
manufacturer to the purchaser. However, in
all except small packages to a consumer,
there is no label warning that "this material
is sold by weight and not volume." For good
mixing and stability of the mix, the particle
size range should be as narrow as possible.
The Mixing Process-Equipment
Blending equipment may be either of the
blade (paddle) type or may be of a gravity
flow type; combinations also exist. The in-
dividual designs of each type show con-
siderable variation to cope with the wide
spectrum of mixing problems encountered,
the specific blending operation involved
and, particularly, the volume capacity of the
blending machine as mixing becomes more
complex as the volume increases. The aim

FIGURE 11-20. Dry blending operation. (Courtesy
of Robertet Flavors , Inc.)
of all these machines is to produce a random
action so that the particles eventually be-
come intimately mixed and uniform dis-
tribution of each type of particle is achieved.
Once this stage is reached , no further bene-
fit is derived from continued mixing. In fact,
the converse may be true. If any segregation
forces are operating (e.g., agglomeration,
buildup of static charges, etc.) further
motion may well cause the product to
become heterogeneous again and without
going that far, cause excessive degradation
of spray-dried or otherwise microencapsu-
lated particles, crystal size of crystalline
materials, etc.
The ideal powder blender should have
the following characteristics: (a) efficient
mixing action, to give satisfactory blending
in minimum time; (b) gentle mixing action,
to reduce mechanical fragmentation or ag-
glomeration to a minimum; (c) dust-free
operation, in which the machine should
preferably be sealed, (d) easily cleanable,
where the surfaces should be smooth, readily
accessible and free of obstructions and
crevices; (e) allow complete discharge, with
a minimum of product retained in the
machine; and (e) low cost, with installation,
running, maintenance and power usage·
costs being minimal. In all cases but the last,
Flavor Manufacturing 591
"minimum" should be or approach "zero"
to be ideal.
The choice of a blender may be deter-
mined on whether the operation is to be of a
batch or continuous nature, on short or long
campaigns (frequency of product change)
and the degree of precision blending re-
quired . Sometimes the choice , particularly
in a multi-use plant, is a compromise . Most
authorities agree that, for simple powder
mixing, the tumbler-type blender is more
effective than the blade or paddle type,
since it can produce maximum product
mobility with a minimum of scraping or
frictional action . It does, however, require a
different material-handling flow adding to
installed cost.
Ribbon Blenders
Ribbon blenders are a pandemic industrial
mixing tool. They consist, basically, of a
trough-shaped casing (usually 2lfz to 3 times
longer than it is wide) with a semicircular
bottom, fitted with a horizontal longitudinal
shaft on which are mounted arms supporting
a combination of ribbon blades, paddles,
and/or helical screws set at a fairly close
clearance to the semicircular mixer body so
that no layer of material remains on the
bottom of the mixer (Fig. 11-21g). To that
end, some mixers have soft wiper blades
impinging on the bottom. The most effec-
tive design of ribbon layout uses a double
spiral, in which the outermost moves the
product in one direction and the inner
moves it in the opposite direction. This
creates axial flow and prevents any buildup
of product at the ends of the trough. The
quantity of material moved by the blades as
they rotate is relatively small so that mixing
times can be long. If blades are made wider,
they require much more power to operate
and must be mechanically reinforced to a
greater extent. The volume capacity for the
design should not be exceeded, otherwise
the ribbon and/or blades are not effective
and the surface layers of the powder do not
get mixed effectively. If the bulk density is
too great, again exceeding the design (which
592 Source Book of Flavors

f)

(a) drum-type blender (b) cube-shaped blender

(c) double-cone blender

(d) twin-shell blender

(el screw-auger blender

If) continuous flow blender

-~c == -:_-.:_
- -- -~ ~
-
-
-
-
--
---
~-~-
·
--
-

-__-_>-
·- -- --
--
- --
~ -:::._ - -= ~ --

(g) ribbon blender

=-~
-
-- f) ~ ~
-
-- --
-
~ :

FIGURE 11-21. Flow patterns in blender.


sometimes happens in a multi-use plant),
the power requirements may be too great
and the mixer will stall, necessitating a great
deal of labor and much inconvenience in
unloading it.
Ribbon blenders are normally operated
at room temperature, but they may be
jacketed for steam heating at low steam
pressure or for cooling by water flow if
needed. When steam heated and operated
with the normal lids open, they become
crude dryers. Although ribbon blenders
have many manufacturers and are relatively
standard in sizes and design, there are many
modifications and variations available, de-
pendent on: (a) materials characteristics;
(b) production requirements, particularly
batch size and working conditions; (c)
machine characteristics, such as loading and
unloading facilities, material of construc-
tion, etc.; (d) auxiliary equipment, includ-
ing built-in sifting facilities; (e) liquid feed
arrangements if the unit is also to be used
for that type of blend in multi-use plants,
and; (f) electrical considerations, such as
hydraulic engines, speed controllers, belts
or gears, etc.
When the blender is to be used for liquid-
solids plating, the ribbons may be redesigned
as plows not extending the full length of the
trough, with the area between plows fitted
with side-entering knife blades, impellers
or pinned discs running at high speed.
These act as internal mills to break up
agglomerates.
Tumbler Mixers
Five main types are in common use: (a)
drum-type blenders, (b) cube-shaped blend-
ers, (c) double-cone blenders, (d) twin-shell
blenders and (e) screw-conveyor and plane-
tary blenders. These blenders have the fol-
lowing characteristics:
Drum-type blenders Drum-type blend-
ers have a cylindrical body with a longitu-
dinal horizontal or inclined axis of revolution
(Fig. 11-21a). Some small units rotate with
the length vertical. Mixing is slow, and
achieved by sliding and cascading. The use
Flavor Manufacturing 593
of internal baffle plates or helices can create
a more random action. The mixing action is
not precise, loading and unloading is incon-
venient, and the units cannot be easily
cleaned. However, one can be jury-rigged
from an open-top type of shipping container
with a lid and rolled back and forth on the
floor, or on a bed of free and driven rollers
at very minimal cost.
Cube-shaped blenders Cube-shaped
blenders have a cubical or polyhedron-
shaped body mounted and designed to
rotate at an angle to the main planes of the
cube (Fig. 11-21b). The flat surfaces tend to
induce sliding flow instead of rolling flow so
that the mixing only occurs as the material
falls from the flat surfaces.
Double-cone blenders Double-cone
blenders are of considerable commercial
importance and are designed so that two
cones are joined and rotate about a central
cylindrical section. The discharge ports are
located at the apex of each cone (Fig. 11-
21c). The mixing action is such that the
powders flow from one cone to the other as
they rotate. This action ensures a rapid and
precise blending so long as the solids do not
occupy more than 50 percent of the blender
volume capacity. There are no blades or
baffles so that the smooth surface is easy to
clean and there is no product holdup.
Twin-shell blender A twin-shell blender
is comprised of two cylindrical sections cut
and joined to form a V-shaped body, which
is mounted to rotate nonsymmetrically so
that the product intermingles by cross-flow
between the two inclined cylinders (Fig.
11-2ld). The mixing rate is fast and precise.
These mixers are easy to clean as all parts of
the body are readily accessible and they can
be completely emptied.
Screw-auger blender The body of this
blender is an inverted cone in which is
mounted a helical screw auger. The auger
lifts the powder from the bottom of the
cone. At the same time, the auger gear is
rotated in a planetary manner around the
periphery of the cone. The mixing is very
efficient and controllable (Fig. 11-21e).
594 Source Book of Flavors

These machines are generally large and considerable effort and expertise to disperse
because of their structure, are difficult to satisfactorily. The end product is usually
clean. They are widely used in the manufac- required to be dry and free-flowing, without
ture of plated spices and seasoning blends. lumps and not subject to caking in storage.
Most of the foregoing types of blenders The mixing operation may spread the liquid
may be fitted with perforated feed pipes or as a thin film over the surface of the dry
nozzles for the admission of liquids and carrier, it may be trapped in the irregular
some with accessory vanes or blades to give interstices of the particles or it may be ab-
more vigorous mixing in a portion of the sorbed into the particles. Sometimes the
blend. (See the following section.) There blending operation involves all three. What-
are combinations wherein the ribbon is re- ever the physical method of adhesion of the
placed by plow-type blades, and additional liquid and solid phases, the individual parti-
high-speed propellers, knives or pinned cles remain discrete. In some cases, particu-
discs are mounted to enter from the side, larly with very sticky oleoresins or vegetable
spinning in the area not occupied by plows extracts, there is a point at which the solid
or vanes. They may be cylindrical or trough- particles lose their individuality when the
shaped and able to be totally closed. The mass agglomerates and becomes pasty. Such
side-entering devices act as virtual mills blendings require special attention to pro-
to break up any agglomerates that may be cessing conditions and procedures. These
formed. particularly, but virtually all liquid-solids
The above blenders are designed for blends may require the addition of per-
batch operation. Continuous solids/solids mitted anti-caking agents (e.g., sodium
blenders are commercially available. They aluminosilicate, tricalcium phosphate, etc.)
consist of a short series of adjustable V- to maintain the free-flowing characteristic.
shaped mixing chambers mounted in-line on The blending operation is complex and
a central rotating axis (Fig. ll-21f). The complete precision of dispersion is almost
dry materials move from a hopper to the impossible to achieve. However, with the
cylinder feeder at a predetermined rate; right equipment and careful attention to
mixing takes place by a backward and technique, a very good degree of dispersion
forward movement over the V-junctions, is possible. Four factors are significant in
with a proportion of the mixed product liquid-solids blending: (a) the liquid and
being continuously discharged at the end of solid phases both should be as finely divided
the mixing train at the same rate as the as possible; (b) preferably both should be
entering feed. suspended in space as they come together;
(c) the liquid-solid mix should be in constant
Liquid-Solids Blending motion so that fresh surfaces are constantly
exposed; and (d) there should be no dead
The blending of solids with a small quantity pockets in the mixing system. If these condi-
of liquid is a basic operation in the manufac- tions are not present, then blending may be
ture of processed spice products, seasonings incomplete and the resulting mix may con-
and other plated flavorings (e.g., vanilla tain areas of high and low concentration
sugar as was mentioned earlier). In most of the dispersed material. Most modern
cases, the solid material consists of small blenders are purpose-designed to avoid this
particles (e.g., sugar, dextrose, salt, silica and yield a satisfactorily uniform product.
gel, flour, etc.) and the liquid may be either The dispersing mechanism is an important
light and mobile (e.g., essential oils, flavor- element of the design and may be either:
ing extracts or concentrates) or viscous and (a) a simple spray nozzle mounted above
pasty (e.g., oleoresins). The former are the surface of the moving solids, (b) a per-
easily spreadable, but the latter may require forated pipe (in effect, a type of nozzle), (c)

rotating knife blades having a central chan-
nel and an annular orifice through which the
liquid is pumped under pressure, or (d) a
submerged high-speed agitator spray over
which the solids flow constantly. All of
these techniques are satisfactory; choice is
dictated by the nature of the materials to be
spread, i.e., the need to use heat or other
processing aids, etc. Whatever method is
adopted, it is likely that the precise operating
conditions will have to be established experi-
mentally; in a multi-use plant, each end
product may require different conditions.
One technique to achieve a good liquid-
solid blend is to blend the liquid into some
of the carrier and then to dilute the mix with
additional carrier containing no additional
liquid. (However, this assures that there will
not be complete homogeneity.) It must be
remembered that particle mobility decreases
as the liquid content increases and that the
conditions pertaining at the end of a blend-
ing cycle are quite different from those at
the beginning of that cycle. Any liquid that
lands on the blender wall or moving parts
may be the cause of surface buildup, in-
complete mixing and problems of cleaning
the equipment at the end of the blending
period.
Under ideal conditions, the blended
product should be perfectly homogeneous
and the liquid phase spread evenly over and
uniformly distributed throughout the entire
mix. Although such perfection is almost
impossible, excellent dispersion is not too
difficult to achieve with thin liquids, but
becomes increasingly more difficult as the
material to be spread or plated becomes
more viscous (e.g., oleoresin black pepper,
extract of mushroom, etc.). Manufacturers
of plated dry-soluble spices have developed
special techniques for handling such prod-
ucts. In all cases, the final blended product
must be passed through a screen of appro-
priate mesh size to ensure that there are no
agglomerates of oleoresin or other extra-
neous matter in the end product.
Flavor Manufacturing 595
FLAVORING MATERIALS
Packaging and Storage
As a unit operation, packaging in the flavor
industry does not have anything like the
same importance it has in the food and
related industries. Package design, con-
venience and product appeal geared to the
marketing of the product to the mass of
consumers takes second place to the need to
get the product to the user with the same
quality that it left the manufacturer. Flavor-
ing materials are generally sold to another
manufacturer for incorporation into his
product, so the packaging is primarily utili-
tarian. The material must be physically pro-
tected against the hazards of transportation
over long distances and through multiple
conditions of climate and terrain by several
carriers: train, airplane, truck, ship, etc. It
must be chemically protected against de-
terioration not only during that transporta-
tion, but also in storage until it is ultimately
used.
While the external package may be
decorated to identify the manufacturer, as
often as not, anonymity may be even more
important. The reader will recall the open-
ing statements of this chapter regarding
the customer-supplier relationships in the
industry and a "neutral" package with
minimal identification of the manufacturer
may be desired by the customer.
The nature of the packaging depends on
whether or not it is to come into direct
contact with the flavoring product. Some
packaging is completely external and serves
only to protect the actual inner container
from damage during the rigorous conditions
to be encountered during travel. That type
of packaging is beyond the scope of this
chapter and may be the subject of legislation
in regard to transportation by air, flamma-
bility, breakage, leakage, etc. (Anon 1977a).
A consideration of the keeping properties of
flavoring substances is essential to making a
decision about the most suitable form of
package to use and is influenced as well by
the quantity to be shipped.
596 Source Book of Flavors
Keeping Properties of Flavoring Materials
Essential Oils
As the main constituents of essential oils
are terpenes, which oxidize readily (become
rancid), it is important that they be pro-
tected from light, heat and air, all of which
accelerate the oxidative reaction. This is
achieved by storing essential oils in amber
glass bottles or metal containers. These
should be well-filled, tightly closed and
stored in a cool place. Citrus oils are par-
ticularly prone to such deterioration, but if
they are stored in full containers in a cold
room (i.e., under refrigeration), they may
be kept for months, even years. The tonnage
used of orange and lemon oils packed in 55-
gallon metal drums lined internally with a
suitable coating may be cited as an example
of the use of proper packaging, which keeps
them from one season to the next, at least.
Glass is becoming less acceptable even for
small quantities of more expensive con-
centrated oils because of the possibility of
breakage in the manufacturing area of the
food itself and contamination of the food
by glass shards. Aluminum bottles, more
expensive but otherwise very good, have
replaced the amber glass bottles once used.
Sometimes the aluminum also has a special
coating that must be resistant to chipping
should the bottle be dropped. Transfer from
larger containers to a size more convenient
to use in the processing area is often an
expedient used even if the material of the
ultimate temporary container, say a particu-
lar plastic such as polyethylene or polypro-
pylene, would not be at all suitable for con-
tinued storage for a week. Most essential
oils obtained by distillation rather than by
solvent extraction or cold pressing improve
with age and may indeed mature, like wines,
for a short period. Some oils are deliber-
ately retained before shipment to allow this
to take place (e.g., peppermint, clove), but
the normal delay between the date of pro-
duction and the time of shipment may suf-
fice. Old oils, those stored for long periods,
may be darker in color, more viscous, and
develop off-odors.
Flavorings and Essences
These usually contain a solvent and are
less prone to change during storage. Condi-
tions similar to those described above apply
equally and care is necessary to reduce
undue exposure to air throughout the filling
process. Inert gases, such as nitrogen, may
be used to purge filled containers. Most
flavorings, be they natural and/or synthetic,
are not at their best when freshly com-
pounded and require an aging period for
the ingredients to meld, for cross-reactions
to take place, which in the case of vanilla
extract might be for several months, to pro-
duce a top-quality flavor profile.
Individual Chemicals
In the case of individual chemicals used
mostly in artificial flavors, the properties
are much more likely to be extremely well-
known. Liquid aldehydes oxidize more
readily than terpenes and should be stored
in well-filled containers, purged with nitro-
gen and kept cool. Yet, while this is known,
cinnamic aldehyde, benzaldehyde and
others are shipped in lined steel drums, dis-
pensed by gravity from drums stored on
racks into smaller containers, with air ad-
mitted freely, without deterioration to the
point that they are not usable. When the
quantity normally used is much less, as with
aldehydes in the range containing 3 to 12
carbon atoms and which are more expen-
sive, the packaging and storage are more
precise and in keeping with the foregoing
precautions. Esters, lactones and alcohols
are generally less prone to deterioration.
Solid aldehydes, such as vanillin and ethyl
vanillin, are used in very large quantity and
are shipped in polyethylene bags inside fiber
or metal containers; bags should be retied
after each increment is removed and they
should be stored in reasonably cool, dry
areas.

Fruit-based Products
Concentrated fruit juices are at their best
when freshly prepared. However, they are
seasonal and it is usually necessary to pro-
cess as much fruit as possible when available
and to store the rest for future processing.
Both the processed fruit and the raw fruit
should be stored under refrigeration. Some
fruits may be dried (e.g., black raspberries,
apricots, currants) and others frozen, but
the exact processing required for each is
beyond the scope of this chapter. If S0 2 has
been used to preserve the fruit, long-term
storage may result in some darkening as the
gas is lost as the packages are opened; re-
placement may be needed. Soft-fruit juices
are not well preserved by this method as the
natural color is slowly bleached and the
flavor becomes unacceptable.
Powder Flavors
Being encapsulated or otherwise "locked
in" by adsorption or absorption, the flavor-
ing components are less liable to oxidative
change or physical loss by evaporation.
These products are quite stable over very
long periods of storage. Polyethylene bags
in fiber outer containers are quite common,
as are polyethylene-lined fiber or steel
drums. They should be kept under low-
moisture conditions and be closed when not
actually in use.
Natural Spices and Seasonings
Whole spices are very stable and retain their
full flavoring power as long as they are
intact. Once comminuted, they lose the
volatile flavorants more rapidly. They are
best stored in an impervious container away
from direct sunlight; many are imported in
bales and are kept in them after sterilization
and/or fumigation. The main problem is to
ensure freedom from moisture as this pro-
motes mold growth and insect reinfestation.
Plated Spice Products
The surface area of these products is great
so that loss of volatile elements and oxida-
Flavor Manufacturing 597
tion is significant unless the product is
packed in an impervious container. The
ubiquitous polyethylene bag in a fiber or
metal outer container, stored in a cool, dry
place is the method often chosen. Under
these conditions, six months is about the
limit for storage and three months is more
likely. As with all perishable products, good
rotation of stock is extremely important;
FIFO (first in, first out) must be carefully
practiced.
Factors Affecting Product Deterioration
Several factors contribute to the deteriora-
tion of flavoring materials (Anon 1970e;
Lees 1974). These largely affect the way in
which flavorings are handled, packed and
stored. The following are of the most
importance but all are influenced by good
housekeeping or the lack of it; careless tech-
niques may offset the best packaging.
Presence of Water
Frequently, water has a deleterious effect.
In flavorings based on solvents such as
alcohol, propylene glycol, isopropanol, etc.,
any dilution with water may result in the
throw-out of constituents as an unsightly
haze in a product which should be clear and
bright. Sometimes clarification as earlier de-
scribed may be necessary; sometimes addi-
tional solvent may do, but this dilutes the
flavor strength. While use of an adjusted
quantity in the end product may be possible,
it is not always so. If the water reacts with
certain ingredients to hydrolyze them as
in some essential oils, the damage can be
irreparable unless the water is removed
promptly. This can be done by the addition
of anhydrous sodium sulphate with stirring,
followed by filtration.
Action of Light
Many flavoring materials, particularly the
essential oils, darken and resinify if exposed
to strong light or sunlight. Flavorings con-
taining natural colorants soon fade under
598 Source Book of Flavors
these conditions. Oleoresin paprika and
paprika powder will turn dark brown,
turmeric fades and similar effects often can
take place. Small quantities (up to about a
gallon or 4 liters) should be kept in amber
glass bottles, aluminum or specially lined
cans; clear glass bottles may be placed inside
a metal or fiber container to exclude light.
It is extremely bad practice to allow any
flavoring material to be stored in an area
exposed to direct sunlight.
Ambient Temperatures
Both extremely hot and cold conditions
have a significant effect on flavoring mate-
rials. The solubility of some constituents of
liquid flavorings is such that they may come
out of solution with resulting clouding or
sedimentation if cooled. Returning the solu-
tion to the original temperature by placing
the container in a bath of warm water or
keeping it in a warm room, followed by
shaking well, usually corrects the condition.
Certain oils (e.g., anise or anethole itself)
freeze completely at cool room tempera-
tures and if this has not caused the bottles
to break, they must be completely melted
before using any portion if the flavor profile
is to be preserved. Hot storage conditions
hasten oxidation, resinification, color deg-
radation and loss of volatile components
when opened. Pressure may develop in the
container by expansion of liquid; too-full
bottles may break, or spillage occur when
the container is opened. Metal drums show
a bulging of the heads and loosening of the
bungs must be carefully controlled to avoid
spraying personnel with the contents.
Atmospheric Oxygen
Air is the cause of much product deteriora-
tion. Citrus oils suffer greatly from this and
when they are emulsified, the water present
contributes to the reaction. While it would
be ideal to purge containers with nitrogen
after each portion is removed, pragmatically
this is very often not possible. At least,
materials should be transferred from larger
containers to smaller ones as portions are
used, rather than leaving half-filled bottles
on shelves between uses. In practice, this
is not done as often as it should be in the
daily fast-paced operations of production
departments.
Trace Metals
Copper, iron and tin in particular are capa-
ble of reacting with any acidic and certain
other functional groups (phenols and alco-
hols most often) to produce off-flavors and
off-colors. Fruit-based flavorings are very
sensitive to this and should be packed in
glass or plastic containers. If metal must be
used, it should be aluminum with a special
acid-resisting coating as the actual material
in contact with the flavor. Drums may be of
steel with similar linings. A particular lining
should be tested for each flavoring to be
packaged, since a lining suitable for a given
flavor may not work well for a different
flavor. If an essential oil has been discolored
badly by a trace metal, it may usually be rec-
tified by washing the oil with a 2-3 percent
solution of either citric acid, sodium bi-
carbonate or EDTA, followed by drying and
filtration. A pinch of the solid moistened
with water and added to an oil may serve the
purpose if it is allowed to stand overnight;
the oil must then be dried and filtered in
most cases. Iron tends to make the material
pink, while copper causes a greenish tint.
Lead in cassia oil not only causes a dark
color but is toxic and must be removed by
distillation. Many of the color problems of
the past were due to the material of con-
struction of the equipment used in the pro-
duction of oils and certain colors were
considered to be necessary in oils of good
quality. These conditions have been largely
eliminated by the use of stainless steel.
Microbiological Deterioration
This is most commonly due to the growth of
yeasts and bacteria, commonplace in fruit
products that readily ferment with the
formation of off-flavor and gas, as well as
color changes. Strict adherence in all stages
of processing, including the packaging into

clean, uncontaminated containers, to a high
level of hygiene both of equipment and
personnel is necessary. Where permitted
and otherwise acceptable, appropriate pre-
servatives (e.g., sodium benzoate, sodium
sulfite or sulfur dioxide) may be used.
Packaging Materials
Numerous materials are used in the fabrica-
tion of packaging for the conveyance and
storage of flavoring materials. Some have
been mentioned in earlier paragraphs in
passing.
Glass
Glass is still the most widely used material
for containers for the storage of flavoring
materials. It is neutral, cheap and reusable,
and the contents are visible for inspection of
quantity and clarity. Glass is produced in
flint (clear) and amber form, and the con-
tainers may be designed in many shapes and
sizes for a variety of closures. In areas used
for compounding of flavors or using flavors
in other products, certain sizes in general
use are different from those most frequently
used for shipping because of convenience in
handling, uniformity on shelving, and for
protection against deterioration. Ingre-
dients used by flavoring manufacturers may
well be received in smaller containers than
those used in shipping the end product, but
flavoring manufacturers have been known
to ship in containers holding a quantity pre-
weighed for their customers' use in batches.
Common sizes are shown in Table 11-2
(with metric sizes not intended to be the
amount contained in the Imperial/USA
size):
TABLE 11-2. Imperial/USA Measure
1b Metric Liters
10 1 Imperial gal. (160 fl oz.)
8 1 U.S. gal. (128 fl oz.)
5 96ft. oz.
20 fl. oz.
0.8 16 fl. oz. 500ml
Flavor Manufacturing 599
The weight capable of being contained in a
given bottle depends on the specific gravity
of the contents, of course.
Five-, 6- and 13-gallon carboys encased in
wooden crates are available and used for
bulk storage. Some chemicals are shipped in
these types of container.
There are disadvantages to the use of
glass, however, the most important of which
is the fragility of the container. In addition
to the high cost of production for special
sizes, shapes and closures, the necessity and
cost of protective devices to prevent break-
age during transportation is critical. Break-
age results, or can result, in more than the
simple loss of the contained material, e.g.,
contamination of other goods on the carrier
being a more costly and possibly dangerous
consequence. Partitioned corrugated card-
board boxes with single or double walls have
been increasingly replaced by foamed poly-
urethane units made to fit snugly around an
individual bottle or several bottles of expen-
sive, toxic or flammable goods. Bottles may
be placed in oversized outer containers of
metal, fiber or wood with the free space
filled with cushioning and/or absorbent inert
packing materials. Food manufacturers are
deeply concerned with safety and with
product liability insurance. They may be
prohibited by Good Manufacturing Practice
regulations against having glass in the
manufacturing area, where a broken bottle
could cause the appearance of glass shards
in a product and this could cause the entire
batch to be dumped.
Glass packages at best need a tight-seal
closure. The more conventional forms of
glass stoppers and corks still used in the
laboratory or compounding area have given
Weight
4.5 to hold 4.0-4.5kg
4 3.5-4 kg
2 2 kg
kg
0.5 kg
600 Source Book of Flavors
way to plastic screw-caps with a plastic, cork
or paper liner, or to all-plastic stoppers. If
liners are to be used, they must be chosen
carefully to be compatible with the contents.
If they are held in place by adhesive, this
too must be compatible. They must not be
loosened once tightened. Aluminum caps
placed on the bottle by a special sealing
machine with a ring wedged tightly to the
neck of the bottle not only serves to close
the bottle tightly, but acts as an anti-
tampering seal; the wedged ring separates
from the top of the cap on opening. Shrink-
able seals placed over the cap when wet act
in the same way to prevent unauthorized
opening or accidental loosening of the cap.
Any unsuitable material could cause the
closure to be ineffective (leakage of air in
and/or liquid out) and/or to make the
product itself unacceptable.
Wood
Only a few products remain transported in
wood. Even beer is now shipped in alumi-
num or stainless kegs. Kegs or casks are
expensive to manufacture and maintain,
barrels for solid product likewise. Wood
internal storage units in the wine industry
and in fruit processing are also disappearing
and are being replaced by stainless steel.
Tin-plate
Lined tin-plate containers are still being
used for the transport of essential oils of
foreign manufacture and some square or
rectangular ones are available in the United
States. In some cases, 5-gal. motor oil cans
have been dismantled, turned inside-out
and reassembled for shipment of resinoids
from third-world areas to more industrial-
ized countries. Where linings are used, the
linings of course are the actual containers,
often being polyethylene for solids and
epoxy resins for liquids.
Steel
Steel drums are available in a range of sizes,
10, 30 and 55 gal. being most common.
There are 5-, 6- and 10-gal. pails that fit into
a similar category. While they may be the
actual container for some products, as often
as not they have internal liners of tin,
lacquer, polyethylene, epoxy resin, or PVC.
Open-head types may have molded poly-
ethylene liners or use bags. Drums are prob-
ably the most versatile for packaging for
bulk flavorings. They are relatively robust,
highly standardized as to size and fittings
and are adaptable to being handled four to
a pallet or by special grabs fitted on fork
trucks. They may be stored on racks and
fitted with a spigot or siphon for dispensing
smaller quantities as required. Most are
single-trip units, whose standards are pro-
mulgated by the ICC in the United States,
but there are also returnable drums of
heavier construction of mild steel or stain-
less steel for services where linings cannot
be used. These are also frequently used for
multiple trips between a manufacturer and a
specific customer for a given product used
regularly in large quantities, where the 15-
to 25-fold higher initial cost is justified by
the long life and neutrality of the material.
A deposit is usually charged for these drums
to ensure their return without monetary loss.
Aluminum
Aluminum containers are produced in many
sizes from 50 ml to 55 gal., with and without
linings. Although costly, they are light and
robust, and sometimes may be washed and
refilled or reused by the customer. They are
valuable for use in export for expensive
essential oils and chemical entities as well as
for flavoring compounds. As with stainless
steel, a deposit may be levied to ensure
return of some types of aluminum multitrip
drums.
Plastics
Plastics are used extensively, but there are
several types of plastics available not com-
pletely interchangeable one with another.
Consumer products use polyvinyl chloride,
polycarbonate or polyethylene. They are
not biodegradable and many localities are

placing restrictions on their use, requir-
ing them to be returned for recycling with
deposits used as an incentive for their re-
turn. This end use has made this type of
container cheap and widely available. Thin-
walled high-density polyethylene containers
of 4-liter or 1-gal. capacity are much cheaper
than the equivalent 1-gal. glass bottles, are
very neutral and compatible with many
products, are convenient to handle and as
they do not break readily, are acceptable
in food product manufacturing areas. Care
must be taken to see that they are properly
sealed when the caps are placed on the
bottles. While some plastics tend to be
permeable to certain constituents (they
must be tested), others are more suitable.
There is a growing problem with disposal of
the used containers with reduction in size by
chopping sometimes required before dis-
posing in land fills.
Plastic drums are also available, generally
being made of heavier construction and of
other materials than bottles. They have
some of the same advantages as steel drums
in handling and storage. Most are single-trip
type. Disposal of empties may require that
they be cut into smaller manageable pieces;
they do make excellent floats for moorings
and rafts in fresh or salt water!
Fiber Drums
Dry flavors may be shipped in fiber drums
containing molded polyethylene insert or
polyethylene bags, which are the true con-
tainers. They have a great advantage in that
a given volume may be made in three or
four different diameters with appropriate
adjustment in the height of the cylinder.
These can be "nested" with the narrower
diameter(s) inside the larger ones saving
transportation costs and storage area at the
point of use; units of still smaller volume
may be nested within the larger sizes. The
lining bags must be correctly proportioned
to fit inside the container so as not to tear
and to have sufficient free height for tying
them closed.
Flavor Manufacturing 601
Storage of Flavoring Materials
The storage of flavoring material of most
kinds should ideally always be in a cool
place with a steady ambient temperature of
65°F(15°C). Steady here means with a varia-
tion of only 5°F; this is not always practical.
Working areas should be either heated or
cooled with air conditioning as necessary,
and there should be no areas directly
exposed to heating coils, radiators, air-
conditioning ports, or direct sunlight. If it is
not feasible to keep sunlight out of the area,
the containers themselves should be imper-
vious to light; but sunlight impinging on a
closed container can warm it excessively.
Packages should be as small as possible con-
sistent with usage; care must be taken to use
older stock first, and not to forget about a
partially used container when an amount is
required that would be more than is in that
already open vessel; some personnel tend to
obtain a new full container and use it, there-
after allowing two partly full units to be
on the shelves. It is also important to have
all the containers of a given material in
close proximity to one another as much as
possible to promote proper stock rotation.
There are exceptions to the above. Some
raw materials should be kept colder (e.g.,
acetaldehyde, which boils at 20.6°C) and
some in freezers (10°F) for sustained shelf
life (e.g., diacetyl).
The following are the points that require
the most attention when handling flavorings
and raw materials:
a. Store at a cool even temperature (or
special temperature).
b. Keep away from moisture.
c. Avoid direct heat and sunlight.
d. Keep containers tightly closed; re-
close immediately after use.
e. Keep ullages at a minimum; transfer
to smaller containers.
f. Do not open fruit-based products
until just before use.
g. Store fruit-based products and citrus
oils under refrigeration at 35°F(2°C).
602 Source Book of Flavors
h. Open containers only when necessary
for use.
1. Ensure that the container supplied by
the manufacturer is suitable to with-
stand long storage or else transfer it
to smaller suitable container(s).
J. Ensure that stock records are ac-
curate and adequate to enable stocks
to be turned over within their normal
shelf life. Each lot purchased should
be clearly marked with date and iden-
tified on the container as well as in
the manual or computerized inven-
tory data.
k. Physical inspection should be made
periodically by supervisors to ensure
that proper rotation and storage tech-
niques are employed.
I. Every container must be correctly,
clearly and unequivocally marked
with the name and/or code number of
the contained material and with con-
ditions of storage if different from
ambient.
m. If there are special hazards associated
with the use of the material, these
should be clearly stated on the label.
The training and supervision of com-
pounders (personnel doing the actual labor)
cannot be too highly stressed. They are the
ones who tend to leave containers partly full
as a matter of their convenience or in haste.
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PART II Flavor Encapsulation
By Gary A. Reineccius
The vast majority of flavor compounds used
in the industry are liquids at room tempera-
ture. Therefore, it is necessary to use some
process to convert these flavor chemicals to
dry, free-flowing powders for use in the
numerous formulated dry products on the
market.
The flavor industry depends upon various
manufacturing techniques for rendering
flavors solids and offering them protection
until consumption. While the encapsulation
techniques used in the industry are numer-
ous, spray drying and extrusion are the two
major commercial processes in terms of
product volume. Minor techniques include
freeze drying, coacervation, fat or wax en-
capsulation, plating (or adsorption) and in-
clusion in cyclodextrins. The processes of
spray drying and coacervation have been
discussed in Part I of this chapter. Coacerva-
tion has been described in detail, but the
importance of spray drying to the industry
justifies a separate and more detailed dis-
cussion in this part of the chapter. Details
on some of the other techniques will also
be included in this expanded treatment of
flavor encapsulation.
SPRAY DRYING
Spray drying is the oldest commercial tech-
nique for producing "encapsulated" flavor-
Flavor Manufacturing 605
formation of persistent toxic chlorohydrins in
food stuffs by fumigation with ethylene oxide
and propylene oxide. J. Food Sci. 30(6):1037-
1042.
Woodroof, J.G. and Phillips, G.F. 1981. Bever-
ages: Carbonated and Noncarbonated. West-
port, Coun.: AVI Publishing Co.
Wylie, D.M. 1959. Fundamentals of filtration.
Congr. Proc. Cosmet. Sci. J. Cosmet. Chern.
ings in volume. The accidental discovery
that acetone, added to tomato puree to help
maintain color and flavor of the tomato
powder, was not lost in the spray-drying
process started the development of encap-
sulated flavorings. Since A. Boake Roberts
and Co. (N. Revie) made this discovery
in 1937, spray drying has become the
most important means of producing dry
flavorings.
The spray-drying equipment used for the
production of dry flavorings is essentially
the same as is used for the production of dry
milk. We therefore find substantial equip-
ment available for the manufacture of spray-
dry flavorings. Equipment availability has
contributed toward making this process the
dominant method for the production of dry
flavorings.
Encapsulation Matrices
The initial step in spray drying a flavor is
the selection of a suitable carrier (or en-
capsulating agent). The ideal carrier should
have emulsifying properties; be a good film
former; have low viscosity at high solids
levels ( <500 cps at >45 percent solids
levels); exhibit low hygroscopicity; release
the flavor when reconstituted in a finished
food product; be low in cost, bland in taste,
and stable in supply; and afford good pro-
tection to the encapsulated flavor (Bangs
1985). Hydrolyzed starches, modified
starches and gum arabic make up the three
classes of carriers generally available
(Reineccius 1991).
606 Source Book of Flavors
Gum Acacia
Gum acacia (arabic) is the traditional carrier
used in spray drying. It is an outstand-
ing natural emulsifier and rates well on the
other criteria used in evaluating a flavor
carrier. Since beverage applications account
for a large proportion of dry flavorings used,
emulsion stability in the finished product is
one of the most important criteria in carrier
selection.
Gum arabic is a natural exudate from the
trunk and branches of leguminous plants of
the family Acacia (Thevenet 1988). There
are several hundred species of Acacia; how-
ever, only a few are gum producers and
these are located in the subdesert region of
Africa. The main gum-producing countries
are the Sudan, Senegal, Mali and Nigeria.
The world market for this gum is about
160,000 tons.
The gum acacia is collected during the
dry season, which runs from November to
May. The trees are tapped by villagers,
exudation occurs, and then the exudate is
hand collected. It is of interest that each tree
will produce only about 300 g/year.
As one might expect based on the grow-
ing region and somewhat primitive means of
collecting gum acacia, supply and quality
are variable. The gum is often contaminated
with foreign matter and has high bacterial
loads. It is variable in functionality also,
since it is collected in the wild from many
different trees as well as species. The long-
term drought in the Sudan left gum acacia in
short supply, with prices exceeding $2.50
per pound. Only in the last few years have
we seen an effort to propagate the most
desirable species of gum-bearing acacia
trees (Thevenet 1988). They are being
planted in regions of Africa where there is
adequate rainfall and harvesting methods are
being improved. We are seeing supply re-
turn and quality becoming more consistent.
Modified Starches
Cost and limited supply have led to the
development of alternative carriers for spray
drying. The chemically modified starches
most closely reproduce the functional prop-
erties of gum arabic. Native starches impart
virtually no emulsification properties to the
spray-dried flavors. This lack of emulsifica-
tion creates two significant problems. The
first is that poor flavor retention results. As
discussed later in this chapter, fineness of
the infeed emulsion has a strong influence
on determining flavor retention during dry-
ing. The second problem relates to the
stability of the flavor emulsion once recon-
stituted in the final product (a beverage, for
example). If the carrier provides no emul-
sification to the flavor, the flavor rapidly
separates from the product and forms a ring
at the top. The most effective way to impart
emulsifying properties to a starch that is still
FDA-approved is to esterify the partially
hydrolyzed starch with substituted cyclic di-
carboxylic acid anhydrides. The FDA has
approved the treatment of starch with a
maximum of 3 percent octenylsuccinic acid
anhydride. This corresponds to a degree of
substitution of 0.02. The modified starch
obtained from this treatment has been re-
ported to be superior to gum acacia in emul-
sification properties and in the retention of
volatile flavors during spray drying (King,
Trubiano and Perry 1976; Trubiano and
Lacourse 1988). However, the modified
starches have some disadvantages: They are
not considered "natural" for labeling pur-
poses, often have an undesirable off-taste
and do not afford good protection to oxi-
dizable flavorings (Reineccius 1991).
Hydrolyzed Starches
The final group of carriers used in the flavor
industry is the hydrolyzed starches (Kenyon
and Anderson 1988). These products range
in dextrose equivalent from about 2 to 36.5.
Hydrolyzed starches offer the advantages of
being relatively inexpensive (approximately
one-third that of the modified starches),
bland in flavor, and low in viscosity at high
solids; and they afford good protection
against oxidation (depending on dextrose
equivalent). The major problem with these
products is the lack of emulsification proper-
 Flavor Manufacturing 607

ties. It is, therefore, not uncommon to use 100

blends of gum acacia/hydrolyzed starches or 90
modified starches/hydrolyzed starches. 80
.......
~ 70
z 60
Flavor Retention 0
i= 50
z...,
In optimizing the process of spray drying, t; 40
one must be concerned about at least three ~
30
product criteria: flavor retention, emulsion
20
stability and protection against deteriora-
10
tion. The relative importance of each of 0 10 20 30 40 50
these criteria depends upon the flavor being INF"EED SOLIDS (")
dried as well as the finished application. FIGURE 11-22. Effect of infeed solid concentration
One would not worry about emulsion stabil- on the retention of diacetyl. (Reineccius and Coulter
ity, for example, in a dry flavoring being 1969)
produced for a frosting, but would for a dry
beverage flavor. Protection would not be
important in a flavor that contained no of this work has suggested that we use as
oxidizable constituents, but would for a high an infeed solids level as possible, recent
flavoring containing citrus oils as another work has shown that there is an optimum
example. Thus, the discussion that follows infeed solids level (Fig. 11-23). Increasing
on optimization must be considered in terms solids level to the point that the additional
of the product and its application. solids are no longer soluble benefits flavor
retention, by decreasing the drying time
Infeed Solids Concentration necessary to form a high solids surface film
Once a carrier (or blend of carriers) has around the drying droplets. Once the drop-
been selected, it must be rehydrated in let surface reaches about 10 percent mois-
water. It is desirable to use a particular ture, flavor molecules cannot diffuse through
infeed solids level that is optimum for each this surface film, while the relatively smaller
carrier or combination of carriers. Research water molecules continue to diffuse through
has shown that infeed solids level is the most this surface film and are lost to the drying air
important determinant of flavor retention (see Bangs 1985 for a theoretical discussion
during spray drying (Fig. 11-22). While most of flavor retention and the supporting refer-

90

-ETHYL
ACETATE
-&·2-
HEPTANON
E
M· METHYL
SALICYLATE

40~--~----~--~--~
40 45 50 55 60
INF"EED SOUDS (")

FIGURE 11-23. Optimization of infeed solids concentration for the retention of

volatiles. (Bangs and Reineccius 1985)
608 Source Book of Flavors

ences). A high infeed solids means that this 100

semipermeable membrane forms quickly
and thus favors flavor retention. It is possible
to pump and atomize infeed materials that
....
M
90
......
contain carrier solids in excess of the solu- z
0
bility limits. Insoluble solids offer no barrier ;::: 80
zw
to the diffusion of flavor molecules and thus t;
do not improve flavor retention during It:
70
drying. We therefore find that there is an
optimum infeed solids level that is unique to
each carrier (Bangs and Reineccius 1985).

FIGURE 11-24. Influence of emulsion size on the

Flavor Concentration retention of orange oil during drying. (Risch and
Once the carrier has been solubilized (with Reineccius 1988)
or without heating), the flavor system must
be added. A 20 percent flavor load based on
carrier solids is traditional in spray drying. lnfeed Homogenization
Higher flavor loads typically result in unac- The infeed emulsion is often homogenized
ceptably high losses of flavors in the dryer. prior to spray drying; however, considerable
Emberger (1981) has shown that about one- process variation exists within the industry
third to one-half as much flavor is retained in this respect. Risch and Reineccius (1988)
during drying when a 25 percent flavor load have shown that there is a direct relation-
is used, compared to a 10 percent loading. ship between degree of homogenization and
Brenner, Henderson and Bergensten (1976) the retention of orange peel oil during spray
have obtained a patent for a process for the drying (Fig. 11-24). Therefore, it appears
production of high-load spray-dried flavor- advantageous to homogenize the dryer in-
ings. They claim that high surface oils and feed material efficiently.
poor flavor retention during drying are
largely the result of particle shrinkage and lnfeed Temperature
cracking during drying. A cracked particle Most often, the dryer infeed is kept at or
surface results in substantial flavor losses near ambient temperature. The influence
during drying and high levels of surface of infeed temperature on flavor retention
(or extractable) oil. Brenner, Henderson, during drying can be considered in two dif-
Bergensten (1976) used a combination of ferent ways. Early work by Sivetz and Foote
polysaccharides (e.g., gum arabic, starch (1963) indicated that chilling the dryer in-
derivatives, and dextrinized and hydrolyzed feed (30 percent coffee solids extract) re-
starches) and polyhydroxy compounds sulted in improved flavor retention. It was
(e.g., sugar alcohols, lactones, monoethers postulated that chilling the infeed increased
and acetals) to form a carrier material that viscosity, which in turn reduced the circula-
remained plastic during spray drying. Using tion currents within the drying droplets.
this plastic carrier, they claimed to be able Reduced circulation currents have been
to spray dry infeed materials with a flavor shown to improve flavor retention. Later
load of up to 75 percent (based on dry work by Kieckbusch and King (1977) has
solids). They reported oil recoveries also shown increasing retention of volatiles
(amount in/amount recovered in the dry as the infeed temperature was lowered. This
powder) of 80 percent at this high loading. effect was, however, attributed to the ef-
There currently are no commercial products fect of viscosity on atomization properties.
on the market using this patent. While this earlier work suggested that one

should consider chilling the dryer infeed,
Thijssen and coworkers (1968, 1972, 1973,
1979) advocated the opposite: warm the
dryer infeed. They pointed out that higher
dryer infeed temperatures permit increased
infeed solids, which thereby improve flavor
retention and have the added advantage of
increasing drying throughput. In some
unpublished work at the University of
Minnesota, Cheng and Reineccius (1990)
could not find any benefit to warming the
dryer infeed from 25 to 65°C even though
they were able to use a higher infeed solids
in the warmer infeed.
Dryer Operating Parameters
Having considered the formulation and
preparation of the material to be spray
dried, one must now consider the effect of
spray drier operating variables on flavor
retention. One needs to choose operating
temperatures, air flow rates, dehumidifica-
tion etc.
Dehumidification
Dehumidification of the dryer inlet air
would be expected to have a beneficial ef-
fect on the retention of volatiles during
spray drying. A lower air humidity would
result in more rapid drying of the atomized
infeed material, thereby shortening the dry-
ing time and the period available for the loss
of flavors. The cost of dehumidifying large
90
80 .x····
•················· ·X
E1o
z .......
E 60
!z: lt.
~.11·····-·-·······-····B
~:~
30~--+---+---+---+-~
70 75 80 85 90
EXIT AIR TEMP. (C)
FIGURE 11-25. Influence of inlet and exit air temperatures on the retention of
diacetyl during spray drying. (Reineccius and Coulter 1969)
Flavor Manufacturing 609
volumes of dryer air is, however, prohibi-
tive. Therefore, one seldom sees air de-
humidification used in the flavor industry.
Inlet and Exit Air Temperatures
The choice of drying inlet and exit air tem-
peratures is determined primarily by the
carrier matrix and flavor being dried. Some
natural flavoring materials (e.g., cheese and
tomato puree) may suffer heat damage
when dried using high exit air temperatures
(Bradley and Stine 1963). In terms of flavor
retention, high exit air temperatures have
been found to be beneficial to the retention
of water-soluble flavors (Reineccius and
Coulter 1969, see Fig. 11-25). This is pre-
sumably due to the fact that air at a higher
temperature will hold more water (i.e., have
a lower relative humidity) than a lower-
temperature air. The lower relative humidity
of the higher temperature exit air results in
more rapid moisture loss during drying and,
therefore, better flavor retention. One
would expect the same results when spray
drying water-insoluble flavors. However,
Anker and Reineccius (1988) found an op-
posite but minor effect of exit air tempera-
ture on the retention of orange peel oil (Fig.
11-26). It appears from this data that higher
exit air temperatures are detrimental to
flavor retention. It is possible that exit air
temperature effects were not substantial in
this latter study due to the very high overall
-INLET AIR
TEMP. 2471:
• INLET AIR
TEMP. 20SC
.,. INLET AIR
TEMP. 163C
95
610 Source Book of Flavors

100 poorer flavor retention at higher inlet air

temperatures.
90 One would anticipate poorer retention
i(
...... of flavors at higher inlet air temperatures,
z 80 since the higher inlet air temperature results
0
;:::
zw 70 in greater moisture in the drying air. More
1-
w moisture results in slower drying and thus
0::
60 greater flavor losses during drying. One
should also note that at some elevated inlet
50~--~--~------~~ air temperature , flavor retention would
80 90 100 11 0 1 20 130 show a substantial decline. One would ex-
EXIT AIR TEt.4PERATURE (C)
pect "ballooning" to occur, resulting from
FIGURE 11-26. Influence of exit air temperatures on the formation of steam within the drying
the retention of orange oil during spray drying. (Anker droplets. Steam formation expands the
and Reineccius 1988)
particle, yielding droplets with thin walls
and a substantially greater surface-to-weight
100 ratio. The inlet air temperature at which
ballooning becomes significant in determin-
g
90
~ ing flavor retention is dependent upon the
infeed solids content, droplet size, type of
z 80
0 infeed solids and spray dryer design.
;:::
z 70
w
1-
w Atomization
0::
60 The next concern in spray drying is atomiza-
tion of the infeed emulsion. We find two
50~----~-----+----~ types of atomizers in widespread use in
150 200 250 300
INLET AIR TEMPERATURE (C) the flavor industry: the single-fluid, high-
pressure spray nozzle and the centrifugal
FIGURE 11-27. Influence of inlet air temperatures wheel. The industry is nearly equally divided
on the retention of orange oil during spray drying. between these two types of atomizers. While
(Anker and Reineccius 1988)
each type of atomization has its unique
advantages and disadvantages, there is no
literature suggesting that one type results
retention (80-92 percent). Other param- in better flavor retention than the other.
eters, such as infeed solids, are considerably Kieckbusch and King (1980) have compared
more important in determining flavor reten- various types of spray nozzles in terms of
tion and, if optimized, yield good retention flavor retention. They compared the Spray-
irrespective of dryer temperatures (within ing Systems LN-1 (centrifugal pressure),
limits). LN-2 (hollow cone design), TG-0.3 (solid
The influence of inlet air temperatures on cone design), and the T-400017 (fan nozzle)
flavor retention during the drying of water- nozzles and found that volatile retentions
soluble flavors is shown in Fig. 11-25. Essen- were all within 3 percent of each other.
tially, Reineccius and Coulter (1969) found Atomization parameters have a signifi-
that lower inlet air temperatures favored cant effect upon the particle size distribution
flavor retention. Lower inlet air tempera- of the resultant powders. Several workers
tures have the disadvantage of reducing have reported that larger particles result in
dryer throughput, which is costly. More re- improved flavor retention. To the contrary,
cent work by Anker and Reineccius (1988) Reineccius and Coulter (1969) found no
on the spray drying of orange oil also shows effect of particle size on flavor retention.

The most recent work by Chang, Scire and
Jacobs (1988) has shown there to be an opti-
mum particle size for flavor retention, and
others have found no relationship. While
particle size may have minimal influence on
flavor retention during drying, it is often
desirable to produce large particles to aid in
dispersion upon reconstitution. Small par-
ticles are often difficult to disperse and float
on the liquid surface. Large particles can be
obtained by using a large orifice size/low
atomization pressure (pressure nozzle only),
high in feed solids, high infeed viscosity, low
wheel speed (centrifugal wheel atomization
only), or some agglomeration technique.
Air Flow Rate
One would expect the air flow rate through
the dryer to influence flavor retention. High
air flow rates should improve retention since
this would shorten drying time . However,
Kieckbusch and King (1980) found no in-
fluence of air flow rate on flavor retention.
They suggested that the large amount of air
entrapment by the expanding spray during
atomization at high air flow rates offsets the
benefits of decreased drying time.
Flavor Stability
The discussion to this point has focused on
the influence of various infeed matrix and
dryer operating parameters on the retention
of volatile flavors during drying. While re-
tention of the flavor during drying is the first
concern, once dried, the flavor must exhibit
good shelf life. When one discusses shelf life
of an encapsulated flavoring, one is typically
concerned about oxidative stability . Many
flavors (especially citrus oils) are very prone
to oxidation and readily develop off-flavors
during storage (Brenner 1983). The major
determinant of oxidative stability is carrier
choice (Subramaniam 1984).
Matrix Effects
As was noted earlier, gum acacia has been
the traditional carrier used for the spray
drying of flavors. Gum acacia has been
Flavor Manufacturing 611
~6
........
<JI
!.
~o.~ 5 i o ~RABIC
I .
~
o 4
0 xM250
~ 3 ~MIOGlJ4
~ I i ·--
2
~, I o 0 ~
o i w9" •J-
~ 0~~~+---~--~--~
0 20 40 60 80
STORAGE Tlt.lE (DAYS)
FIGURE ll-28. Influence of encapsulating material
on the shelf-life of spray-dried orange oil. (Westing,
Reineccius, and Caporaso 1988)
shown to provide an intermediate amount
of protection to encapsulated citrus oils
(Westing, Reineccius and Caporaso 1988).
As can be seen in Fig. 11-28, gum acacia
provided about 40 days shelf life (generally
consider shelf life to end at about 2 mg
limonene oxide per g limonene) to an en-
capsulated single-fold orange peel oil when
held at 37°C (no antioxidant added). A
modified starch product (Amiogum®,
American Maize Products, Hammond, IN)
tested under the same conditions provided
a shelf life of only 20 days. The poor shelf
life obtained by the product encapsulated
using the modified starch has been ob-
served using another commercial product
(Capsul®, National Starch) both in unpub-
lished studies in our laboratory and in work
published by Baisier and Reineccius (1989).
These results would appear to contradict the
work of Trubiano and Lacourse (1988), al-
though too few data were presented in this
latter publication to make a comparison of
results.
As can also be seen in Fig. 11-28, quite
superior shelf life was observed for the
orange oil encapsulated in 25 DE corn syrup
solids (M-250, Grain Processing Corp.,
Muscatine, lA). The shelf life afforded by
the corn syrup solids matrix was about 160
days. This is quite superior to both gum
acacia and the emulsifying starches.
Subramaniam (1984) and Anandaraman
 612 Source Book of Flavors

Inglett, Gelbman and Reineccius (1988)

9 have evaluated the efficacy of enzyme-
w
8
I modified wheat, potato, cassava, rice,

Ir
9
X
7 amylomaize, corn and waxy corn starches
0
Q._ 6 DE 4 for the encapsulation of citrus oils. As is
w
shown in Table 11-3, substantial differences

~Vr·
I • DE 10
~
• DE 20 in flavor retention and shelf life were ob-
I
w
z o DE 25 served for the different hydrolyzed starches.
w
z X DE 36 While the amylomaize gave the best flavor
0
:::1
::::;
retention during drying, it unfortunately
gave the poorest shelf life. Reasonable
alternative starches for flavor encapsulation
appear to be wheat, cassava and rice. These
products gave adequate retention and very
FIGURE 11·29. Influence of the degree of starch good shelf life.
hydrolysis (encapsulating material) on the shelf-life of
spray-dried orange oil. (Anandaraman and Reineccius
1986) Dryer Operating Parameters

Particle Size
TABLE 11-3. Comparison of various enzyme- While there has been a significant amount of
hydrolyzed starches for the encap-
sulation of orange peel oil (Inglett,
research evaluating flavor carriers in terms
Gelbman, and Reineccius 1988) of product shelf life, little has been done on
the role of spray dryer operating parameters.
Shelf-life Chang, Scire and Jacobs (1988) studied the
Flavor retentio n at 37"C
role of particle size in the shelf life of spray-
Starch (%) (days)
dried orange peel oil. Particle size was
Wheat 67 >120b varied by changing the wheel speed of their
Rice 61 >120 centrifugal atomizer. They found the powder
Cassava 59 > 120 produced at the intermediate wheel speed
Corn 46 > 120
Waxy corn 45 > 120
(53.21 micron average particle size) to be
Potato 49 78 the most stable to oxidation (Table 11-4).
Amylomaize 72 51 They hypothesized that stability should in-
aRetention of orange peel oil. crease with increasing particle size; how-
bStudy terminated at 120 days storage . ever, surface imperfections increase with

and Reineccius (1986) have shown that

TABLE 11-4. Inftuence of particle size on shelf life of
simple hydrolyzed starches can give excel- orange peel oil (Chang, Scire and
lent protection to spray-dried orange oils, Jacobs 1988)
and that the degree of protection is directly
related to the dextrose equivalent of the Particle Flavor Oxidation
Atomizer Sizeb load rate'
hydrolyzed starch (Fig. 11-29). There are, voltage• (J.lm) (% ) (mg/g oil/day)
however, problems in using the simple
hydrolyzed starches as flavor carriers. As 200 42.5 15.2 4.04
was noted earlier, these products lack any 150 53.2 15.9 2.36
75 66.6 12.8 3.36
emulsifying properties and typically result
in poor retention of volatile flavors during a Particle
size was varied by changing voltage to the atomizer
motor.
drying (Westing, Reineccius and Caporaso b Mean particle diameter.
1988). 'Formation of limonene·l ,2-epoxides during storage at 45oC.

particle size, and at some point the surface
imperfections leave the oil susceptible to
oxidation and thus decreased stability.
They, therefore, felt that there is an
optimum particle size for flavor stability.
Inlet and Exit Air Temperatures
A second dryer operating parameter that
has been studied in relation to product shelf
life is dryer inlet and exit air temperature
(Anker and Reineccius 1988). Over a range
of 160-280°C inlet air temperatures, the
highest inlet air temperature was found to
give the best shelf life and the lowest, the
poorest shelf life. This finding is somewhat
contradictory to expectations. As one in-
creases inlet air temperature, the absolute
density of the spray-dried powder decreases.
This effectively means that more air is incor-
porated into the dry particles and that there
is more surface area per unit weight of
powder. Both of these factors should result
in decreased shelf life at increased inlet
air temperature. Surprisingly, Anker (1988)
found no decrease in density even at the
highest inlet air temperatures, and thus no
decrease in flavor retention or shelf life.
In addition, Anker and Reineccius (1988)
found no relationship between exit air tem-
perature (range 80-130°C) and product
shelf life. While one would expect higher
product temperatures to accelerate (or
initiate) oxidative changes, the residence
time in the dryer is apparently too short to
be of any significance.
Water Activity
The role of water activity in determining
shelf life of the spray-dried powders is of
interest. It is well documented in the litera-
ture that lipid oxidation is a minimum at the
monolayer (water activity circa 0.2) and will
increase on either side of the monolayer.
Anker and Reineccius (1988) found that
shelf life of orange peel oil encapsulated
in gum acacia increased with water activity
within the range of water activity studied
(0.0 to 0.536). More recent work has shown
Flavor Manufacturing 613
that the type of encapsulation matrix deter-
mines the influence of water activity on shelf
life (Ma 1991). Ma (1991) confirmed the
work of Anker (1988) on gum acacia and
found that extending the water activity
range out to 0.75 resulted in a decreased
shelf life. Thus, it appears that there is an
optimum water activity for the stability of
materials encapsulated in gum acacia (circa
0.55). Ma (1991) also looked at the role of
water activity in influencing the shelf life of
orange oil spray dried in Capsul and malta-
dextrin (M-100). She found that shelf life
increased with water activity to 0.75 (upper
limit of study) for the maltodextrin, and
there was an inverse relationship between
the two for Capsul. Thus, one will have to
consider the matrix in determining the water
activity (moisture content) that will give the
optimum shelf life. However, it is clear that
there is no shelf life rationale for producing
powders in the traditional2-5 percent mois-
ture range.
It is worthwhile to note that the proper
choice of encapsulation matrix will yield
shelf life in excess of one year, using typical
spray drying processes without any anti-
oxidant.
EXTRUSION
When one hears the word "extrusion," one
generally thinks of a high-temperature,
high-pressure screw extruder that is used in
the cooking and texturizing of cereal-based
products. "Extrusion" as applied to flavor
encapsulation is used in a broader sense in
that a flavor emulsion is forced through a
die. The pressures are typically less than
100 psi and temperatures seldom exceed
l15°C.
Process
Extrusion ranks second in volume for the
production of encapsulated dry flavorings.
This process originated from the basic ideas
of Schultz, Dimick and Makower (1956),
614 Source Book of Flavors
Sugar-starch Essential oil
I
hydrolysate
mixture
I
Heat to
Antioxidant
( Optional )
molten state
I
Emulsifier
Emulsification f - Nitrogen
( closed vessel )
I mixture was agitated violently under nitro-
Extrusion
I gen to form an oxygen-free emulsion. This
Impact break- .,_lsopraponol
ing (in IPA ) ( IPA )
Separ~ion I oils), which was then rapidly cooled or
of ljA
"'T
Anti caking
agent
Screening I
packaging
FIGURE 11-30. Process used in the encapsulation of
flavor materials via extrusion. (Beck 1972)
who simply added citrus oils to a molten
carbohydrate mass (like hard candy), agi-
tated it to form a crude emulsion, and then
allowed it to solidify as a mass. The mass
was ground to the desired particle size and
sold as an encapsulated flavoring material.
Swisher (1957) combined the basic for-
mulation of Schultz, Dimick and Makower
(1956) with extrusion to produce a process
similar to that used today in the flavor indus-
try (Fig. 11-30). Swisher (1957) used a 42
DE corn syrup as the encapsulation matrix.
Antioxidant was added to provide stability
to the citrus oils during the high-temperature
processing. Butylated hydroxyanisole and 4-
methyl-2,6-ditertiarybutylphenol were men-
tioned by name in Swisher's patent and use
level was suggested to be 0.05 percent of the
flavor oil. Emulsifiers were also added in
order to facilitate emulsion formation and
promote stability. While numerous syn-
thetic and natural emulsifiers were sug-
gested in his patent, patent examples used a
blend of monoglycerides and monoglyceride
sodium sulfoacetate at 1 percent level
(based on total emulsion weight). This corn
syrup/antioxidant/emulsifier mixture con-
tained from 3 percent to 81/2 percent mois-
ture, and temperatures of about l20°C were
necessary to keep the solution sufficiently
low in viscosity to permit the incorporation
of flavoring oils. Flavoring oils were incor-
porated at about a 10 percent level and the
emulsion was forced through a die into a hot
immiscible liquid (e.g., mineral or vegetable
simply extruded into pellets, which were
allowed to solidify and then ground to the
desired particle size. The ground material
was washed with solvent (e.g., isopropanol)
to remove surface oil and then dried under
vacuum. The end product of this process
was a free-flowing granular material con-
taining 8-10 percent flavoring.
Swisher (1962) was awarded a second
patent on this process, which incorporated
several improvements. He suggested incor-
porating 4-9 percent glycerol into the
initial corn syrup solids. The glycerol func-
tioned as a heat exchange medium, per-
mitted solubilization of the corn syrup solids
at a lower moisture content, and acted as a
plasticizing agent in the finished product.
The plasticizing effect minimized cracking
of the product, which would permit oxygen
to contact the flavoring material and thereby
limit shelf life.
A second major innovation in this later
patent was the extrusion of the hot flavor/
carbohydrate melt through a die (approxi-
mately 1164-in. holes) into a cold solvent
bath. While several solvents (e.g., kero-
sene, petroleum ether, methanol, acetone,
methylethyl ketone, limonene, benzene and
toluene) were suggested in his patent, iso-
propanol was used as the solvent of choice
in his examples and is used today in the
industry. The extrusion into a cold solvent
bath was a key innovation in that the solvent
served to rapidly solidify the carbohydrate

matrix into an impermeable amorphous
structure, washed residual surface oil from
the product that otherwise would have
oxidized causing off-flavor problems, and
also served to extract moisture from the
finished product. Swisher (1962) found that
soaking times ranging from 36 to 144 hours
reduced moisture content down to 1/2 per-
cent to 2 percent. When sufficient agitation
was used in the bath, this step also served to
reduce particle size (practical limit is when
piece length equals diameter). Therefore, it
was no longer necessary to grind the solidi-
fied flavoring and wash it, since these two
operations were now combined into the
solidification step of the process.
The residual solvent was removed from
the product through air drying. At this time,
additional moisture could also be removed
(if one chose to reduce soaking time) and
various anticaking agents could be added.
The combination of high dextrose equi-
valent corn syrup solids and glycol was quite
hygroscopic, so anticaking agents such as
tricalcium phosphate were recommended
to maintain the product as a free-flowing
particulate.
The process of encapsulation via extru-
sion has remained largely unchanged since
Swisher's (1962) patent. Recent innovations
have focused primarily on the formulation.
Beck (1972) replaced the high-DE corn
syrup solids with a combination of sucrose
and maltodextrin. He used a carbohydrate
melt consisting of about 55 percent sucrose
and 41 percent maltodextrin (10-13 DE).
The remaining ingredients were moisture
and additives. This low-DE maltodextrin/
sucrose matrix was considerably less hygro-
scopic than that used by Swisher (1957,
1962). Beck (1972), however, did continue
the use of anticaking agent and recom-
mended pyrogenic silica rather than trical-
cium phosphate. The flavor load obtained
by Beck (1972) generally ranged from 8
percent to 10 percent, with 12 percent con-
sidered as a practical maximum.
Barnes and Steinke (1987) were awarded
a patent in which they used a modified food
Flavor Manufacturing 615
starch in place of the sucrose. The modified
food starch selected was either Capsul®
(National Starch) or Amiogum® (American
Maize). Both of these starches have been
chemically modified to produce a product
with emulsification properties. Barnes and
Steinke (1987) stated that the emulsifying
starch, with its lipophilic characteristics,
would absorb the flavor oils into the matrix.
The maltodextrin was, therefore, used pri-
marily to provide bulk and some viscosity
control. Barnes and Steinke (1987) claimed
that the use of emulsifying starches in the
encapsulation matrix would permit increas-
ing the loading capacity to 40 percent
flavoring.
In addition to achieving increased flavor
load via the use of emulsifying starches,
several other benefits were claimed. Total
replacement of sucrose with emulsifying
starches resulted in a product which was
"sugar-free." This may have some advan-
tages in marketing a finished food product.
Sucrose substitution with modified starch
also permitted greater flexibility in manu-
facturing. Sucrose will readily invert to
glucose and fructose at low pHs and high
temperatures. This inversion will result in
the product becoming more hygroscopic and
it will participate more readily in non-
enzymatic browning. Therefore, the replace-
ment of sucrose permitted longer cooking
times, larger batch sizes and higher cooking
temperatures.
Barnes and Steinke (1987) claimed that
fruit essences, fruit juices, volatile sub-
stances and propylene glycol could be en-
capsulated using their encapsulation matrix.
In order to successfully encapsulate fruit
essences, however, it was first necessary to
remove the water and low molecular weight
alcohols from the essence. The essence was
then incorporated into an edible oil so that it
would form an emulsion with the encapsula-
tion matrix.
This matrix was also purported to be use-
ful for the encapsulation of fruit juices.
Barnes and Steinke (1987) stated that
orange juice concentrate (42 percent water)
616 Source Book of Flavors
could be encapsulated at 10-15 percent
loading levels. The prior formulations using
sucrose were limited to 5-6 percent juice
solids loading and could be used only with
concentrates containing :::::;20 percent water.
Barnes and Steinke (1987) emphasized
that their system was suitable for the encap-
sulation of flavorings containing propylene
glycol. Since many flavorings use propylene
glycol as a solvent, this capability provided
greater flexibility in flavor formulation for
extrusion encapsulation.
Barnes and Steinke (1987) provided
numerous examples of how their formula-
tion could be applied to produce encap-
sulated flavorings. Flavor loads obtained in
the patent examples ranged from 12.4 per-
cent to 24.2 percent by weight. No data
were provided on encapsulation efficiency
at the higher loadings. Encapsulation effi-
ciency was generally the limiting factor in
going to higher flavor loadings using previ-
ously developed encapsulation matrices.
A patent awarded to Miller and Mutka
(1986) dealt primarily with optimization of
the extrusion process. It was their intent to
improve the flavor load and encapsulation
efficiency.
A study of the effect of cook temperature
on flavor load and encapsulation efficiency
indicated that high-load products (greater
than 22 percent) had an optimum cook tem-
perature of about 123°C. As can be seen
in Table 11-5, temperatures above or below
this resulted in poor encapsulation ef-
ficiencies. Since the cook temperature is
TABLE 11-5. lnlluence of cook temperature on
encapsulation efficiency (Miller and
Mutka 1986)
Oil Encapsulation Cook
encapsulated efficiency temperature
(%) (%) ("C)
20.5 63.5 118
22.9 70.9 122
21.1 65.3 126
19.3 59.8 130
19.2 59.4 134
basically determined by moisture content,
Miller and Mutka (1986) postulated that too
little moisture reduced emulsification effec-
tiveness, while too much moisture hindered
encapsulation. A cook temperature of 123°C
corresponded to about 5 percent moisture.
A study on emulsifiers indicated that both
emulsifier type and level influenced encap-
sulation efficiency. While Miller and Mutka
(1986) specified 0.5 percent to 5 percent
emulsifier based on the total weight of the
carbohydrate melt, they found the optimum
level of mono- and diglyceride polyglycerol
esters or lecithin to be 1.9 percent.
Miller and Mutka (1986) have also evalu-
ated the influence of pressurization of the
extrusion vessel on encapsulation efficiency.
While previous workers have mentioned
pressurization of the extrusion vessel with
nitrogen or carbon dioxide to minimize off-
flavor development, no one has presented
evidence that they focused on the effect of
pressure on encapsulation efficiency. Miller
and Mutka (1986) found that pressures
ranging from 7 to 50 psi yielded the best
encapsulation efficiencies. Pressure above
100psi often resulted in unstable emulsions,
which exhibited very poor encapsulation
efficiencies.
In summarizing the work of Miller and
Mutka (1986), they have found that optimiz-
ing cook temperature, emulsifier concentra-
tion, and the pressurization of the cook
vessel yielded improved encapsulation effi-
ciency at high flavor loadings. While their
patent claims loadings up to 35 percent, only
one patent example went as high as 27.6
percent. The majority of examples demon-
strated feasibility at flavor loadings from 15
percent to 20 percent. This, however, is still
well above the traditional 8-10 percent
flavor loadings achieved in commercial use
at the present.
Process Strengths
The primary strength of extrusion is unques-
tionably its outstanding protection of the
flavor against oxidation. Swisher (1957)
conducted an accelerated shelf-life test on

encapsulated orange peel oil (no antioxidant)
and found it was in excess of four years. This
is vastly superior to any other means of
flavor encapsulation in commercial use.
In addition to offering exceptional shelf
life, extruded flavors have another advan-
tage over other encapsulation processes in
producing visible pieces of flavoring. This is
significant only in terms of marketing.
Process Weaknesses
In terms of weaknesses, extrusion is con-
siderably more expensive (processing costs)
than spray drying. Process costs are esti-
mated to be nearly double those of spray
drying.
Flavor load is currently running in the 8-
12 percent range for commercial products.
Considering that 20 percent loading is
standard for spray drying, extrusion also
delivers less flavor per unit weight.
One can readily appreciate the problems
in forming a good emulsion in an extremely
viscous carbohydrate melt. Westing et al.
(1988) found that two commercial samples
of extruded orange peel oil had particle size
FIGURE 11-31. Structure of 13-cylodextrin. (Szetli 1985)
Flavor Manufacturing 617
averages of 3.3 and 6.0 f.!m. This is too large
to be stable in a beverage application. In
addition, the large piece size of the extruded
product is not readily soluble in cold water.
The slow dissolution rate can be a concern
again in cold beverages.
A last concern for shortcomings of ex-
trusion encapsulation is that it is a high-
temperature process. The flavoring must be
able to tolerate 110-120°C for substantial
time periods because this is a batch process
that subjects the flavor to significant time
periods at the elevated temperatures.
MOLECULAR INCLUSION VIA
CYCLODEXTRINS
While cyclodextrins were discovered many
years ago, their potential application for
flavor encapsulation has been studied only
during the last decade (Szejtli 1982, Szejtli
1981, Szente and Szejtli 1988). Incomplete
toxicity data and limited availability, only as
fine chemicals at high prices, negated con-
sideration as potential encapsulating agents
for flavors. Recent toxicological studies and
618 Source Book of Flavors

the development of commercial methods for ETHANOL/WATER (2:1)

production via fermentation have now made
the cyclodextrins of interest.
I
HEAT TO 55 C
The structures of the common cyclo-
dextrins are shown in Fig. 11-31. The cyclo-
I
ADD CYCLODEXTRIN (10" w/w)
dextrins are produced from starch by select
microorganisms (e.g., Bacillus macerans
I
ADD F"LAVOR - STIRRING
and Bacillus circulans). These organisms
have a cyclodextrin-transglycosidase, which
I
COOL SLOWLY
(-4C)
converts the partially hydrolyzed starch
into cyclic dextrins containing six (a), seven I
F"ILTER
(~), or eight (y) glucose molecules. ~­
Cyclodextrin has been found to be most I
AIR DRY
suitable for the inclusion of typical flavor
molecules. As a result of the glucose con- FIGURE 11-32. Process for the molecular inclusion
formation, all the secondary hydroxy groups of flavoring materials with ~-cyclodextrin. (Risch and
Reineccius 1986)
are located on one side of the "torus-like"
cyclodextrin molecule and all the primary
hydroxy groups are located on the other continuous agitation. Immediately upon the
side. The interior of the molecule is some- addition of flavoring, the ~-cyclodextrin
what nonpolar since it is formed by hydro- complex starts to precipitate. The solution is
gen atoms and glycosidic oxygen bridge stirred continuously as the temperature is
atoms. Molecules that are less polar than allowed to drop to room temperature, and
water (i.e., most flavor substances) and then the solution is placed in a refrigerator
have suitable molecular dimensions to fit to reach a final temperature of 4°C. Time
inside the cyclodextrin interior can be in- must be given for the efficient formation of
cluded into the cyclodextrin molecule. In the complex, and lowering the temperature
aqueous solution, the slightly nonpolar enhances precipitation (i.e., recovery). The
cyclodextrin interior is occupied by water cold, precipitated material is recovered
molecules, which are energetically unfavor- from the solvent by filtering, initially air
able and thus readily substituted by the less dried, and finally dried at 50°C for 16 hours.
polar flavor molecules. Cyclodextrin com- The result is a free-flowing cyclodextrin/
plexes are relatively stable and their solubil- flavor complex, which contains from 6 per-
ity in aqueous solution is greatly reduced cent to 15 percent flavoring (Szejtli 1982).
compared to the uncomplexed cyclodextrin. Alternate methods of preparing the cyclo-
Therefore, the complexed cyclodextrins dextrin complex involve mixing flavoring
readily precipitate from solution and can be materials into a paste of the cyclodextrin or
recovered simply by filtration. passing vapors through a solution of cyclo-
dextrin. In all methods, it is necessary to
solubilize both the cyclodextrin and the
Process
flavoring material. If the flavor is insoluble
One process for forming cyclodextrin com- in water, it is necessary to initially dissolve
plexes is illustrated in Fig. 11-32 (Westing, the flavor in a solvent such as ethanol.
Reineccius and Caporaso 1988). In essence,
~-cyclodextrin is first dissolved in a 2: 1 Flavor Loading
ethanol: water mixture at 55°C. In this sol- The composition of the cyclodextrin com-
vent at 55°C, ~-cyclodextrin will be soluble plex will depend upon the molecular weight
at a concentration of slightly more than 10 of the flavoring material. Since one mole-
percent. Flavoring is then slowly added with cule of cyclodextrin will normally include
 Flavor Manufacturing 619

TABLE 11-6. P-Cyclodextrin complexes of several has been observed. Data presented in
flavoring materials (Szejtli 1981) Tables 11-6 and 11-7 show the theoretical
Flavor Material Complex content• (%)
loadings for some pure compounds and the
observed loadings of some natural flavoring
Vanillin 6.20 materials.
Dill oil 6.92 It has been demonstrated that cyclodex-
Marjoram oil 8.00
Benzaldehyde 8.70
trins have a variable affinity for different
Lemon oil 8.75 flavor compounds. This may be used to ad-
Cinnamon oil 8.76 vantage or can be a disadvantage. Shaw and
Anise oil 9.00 Wilson (1984) and Shaw, Tatum and Wilson
Peppermint oil 9.70 (1984) have taken advantage of variable
Garlic oil 10.20
Caraway oil 10.50
binding properties by using ~-cyclodextrin
Mustard oil 10.92 to selectively remove bitter substances
• Determined experimentally.
from orange and grapefruit juices. ~­
Cyclodextrins have also been used to
remove off-flavors from old rice (Takeda
one flavor molecule, the loading depends 1981), and beany odor and taste from
upon the average molecular weight of the soybean products (Home Food Co. 1983).
compounds included. It should be noted Variable binding properties can be a dis-
that the theoretical maximum loading is not advantage in the encapsulation of flavor
always obtained. Pagington (1986) stated compounds. Risch and Reineccius (1986)
that dimethyl sulfide should be complexed found from zero inclusion (isoeugenol) to
at 5.5 percent, but only 2 percent loading 100 percent inclusion (ethyl hexanoate and

TABLE 11-7. P-Cyclodextrin complexes of individual flavor chemicals (Pagington

1986)

Molecular sizeb (nm)

Aroma components Molecular weight" Length Diameter

Allicin 162.27 1.2 0.5

Allylisothiocyanate 99.19 0.7 0.4
Diallyldisulfide 146.26 1.2 0.5
Anethole 148.20 1.0 0.6
Benzaldehyde 106.12 0.9 0.6
Benzyl alcohol 108.13 0.9 0.6
Benzoic acid 122.12 0.9 0.6
Borneal 154.24 1.1 0.7
Cineol 154.24 1.0 0.7
Citra! 152.23 1.0 0.6
Citronellol 156.26 1.0 0.6
Cinnamaldehyde 132.15 0.9 0.7
Cinnamic acid 148.16 0.9 0.7
Eugenol 164.21 1.0 0.6
Fenchone 152.23 1.1 0.7
Geraniol 154.24 1.0 0.7
Camphene 136.23 0.9 0.7
Carvone 150.21 1.0 0.7
Linalool 154.24 1.0 0.7
Menthol 156.27 0.9 0.6
•Divide by 11.34 to give theoretical content (percent loading) of BCD complex.
hMolecular dimensions of flavor molecule.
620 Source Book of Flavors
linalool) when they added a model flavor
system to ~-cyclodextrin in an ethanol :
water solution. The losses in flavor com-
pounds were due to a lack of inclusion
rather than a loss during the subsequent
complex recovery and/or drying steps. Once
the complex was formed, it was quite stable
to evaporation.
The variable inclusion properties of cyclo-
dextrins may result in a dry flavor quite
different from the original liquid flavor
when the flavor is comprised of a broad
range of flavor molecules (e.g., an artificial
fruit flavor that contains short-chain esters
and longer-chain character impact com-
pounds). However, flavors such as orange
that have been included in ~-cyclodextrin
may not be distinguishable from fresh orange
even by trained taste panels (Westing,
Reineccius and Caporaso 1988).
Shelf Life
There are substantial data in the literature
that document excellent protection for sub-
stances included in cyclodextrins (Westing,
Reineccius and Caporaso 1988, Szejtli 1982,
Szejtli 1981, Szente and Szejtli 1988). As
was mentioned earlier, the included com-
plex is very stable to evaporation. Szejtli
(1982) reported only about a 5 percent loss
of included volatiles after two years' storage
at room temperature. More important, how-
ever, is the oxidative stability of included
flavor compounds. Szejtli (1981, 1982),
Szente and Szejtli (1988), and Westing,
Reineccius and Caporaso (1988) have dem-
onstrated that inclusion complexes are vir-
tually totally stable to oxidation. Szente and
Szejtli (1988) reported that several flavor
inclusion complexes were evaluated for
organoleptic quality after 10 years of stor-
age. All samples were found to be of good
sensory quality. The work of Westing,
Reineccius and Caporaso (1988) found
some initial oxidation of included single-fold
orange peel oil during storage; however, the
extent of oxidation was minor and probably
limited to the small amount of orange oil
that was not successfully included.
In summary, cyclodextrins provide ex-
ceptional protection to included flavors in
terms of oxidation and evaporative losses.
Their selective binding properties may or
may not be an advantage, but must be con-
sidered. The short-term barrier to use in the
United States is a lack of GRAS status.
Cyclodextrins currently are not permitted
for use in foods. The long-term factor that
will limit use is cost. Cyclodextrins are made
from starch using a fermentation process.
While prices will drop as commercial pro-
duction increases, the cost will probably
never go below $2.50 to $3.00 per pound.
Considering the limited flavor load (6-15
percent flavor on a dry basis) and the low
cost of competing processes and encapsulat-
ing materials (as low as 30 cents per pound),
cyclodextrin use is and will continue to be,
relatively speaking, very costly. Cyclodex-
trin use will be limited to very special appli-
cations where competing processes fail, or
where very high value materials must be
protected.
COACERVATION
Coacervation has found limited use in flavor
encapsulation (Versic 1988, Balassa 1970,
Brodnitz and Pascale 1972). However, work
is currently in progress on this method and
perhaps we will see its application in the
future (Arneodo, Benoit and Thies 1986,
King 1988, Arneodo et al. 1988). This topic
has been covered adequately in the first part
of this chapter by Shay, so it will receive no
further treatment there.
FAT ENCAPSULATION
It is often desirable to produce a dry flavor-
ing that has specific release properties. In
many food applications, a thermal release
property would be desirable. Thus, the
flavor system would be protected from the
food and environment until the product was
heated in final home preparation. There are
several ways to achieve thermal release
properties in encapsulated flavors.

Spray Chilling
One may simply encapsulate a flavor in fat
by mixing the flavor with fat and then spray-
ing the fat/flavor solution into a cold spray
dryer. The fat solidifies, forming a free-
flowing powdered fat. However, there is
little or no barrier to the loss of the flavor by
diffusion if the flavor has solubility in the
fat. Alternatively, one may choose to use
a fat or wax that is immiscible with the
flavoring system. This system could again be
chilled and flavor would result, which is very
similar to the normal spray-dried product
except that the carrier would now be lipo-
philic in nature. The major problem with
this approach is finding inexpensive food-
grade materials that are lipophilic and yet
immiscible with the flavor. This system
could, however, be useful in the encapsula-
tion of aqueous flavor systems (Smith and
Lambrou 1974). A water-in-fat emulsion
would be produced.
Two-Fluid Atomization
A flavor in solid fat can be made by an
alternate technique that incorporates a two-
fluid atomizer to form the particles (Arens
and Sweeney 1969). In this process, the
flavoring is forced through the center orifice
of the atomizer, while the melted fat (or
FILTER HOUSING
EXPANSION CHAMBER
PARTICLE FLOW
PATTERN
PROOUCT CONTAINER
AIR INLET LOWER PLENUM
FIGURE 11-33. Fluidized-bed coating of spray-dried flavorings. (Jones 1988)
Flavor Manufacturing 621
wax) is forced through the surrounding
orifice. The fat coats the core material and
solidifies. This process was initially licensed
to a flavor house for development. How-
ever, process limitations, including large
particle size (800-4000 J..Lm) and limitations
in material choice (beeswax and paraffin) ,
have kept this process from commercial
realization.
Secondary Coating
A technique for obtaining flavorings with
thermal release properties that offers several
advantages over the methods discussed so
far is secondary coating of already encap-
sulated materials. One may choose to coat a
spray-dried flavoring with an edible fat, for
example. This approach offers the advan-
tage of providing excellent protection to the
flavoring through the initial encapsulation
and then tailor-made solubility/meltability
by the secondary coating process.
This secondary coating can be accom-
plished in several ways. Preferred methods
include air-suspension coating and centri-
fugal extrusion (Sparks 1981).
Fluidized Bed Coating
Fluidized bed (air-suspension) coating in-
volves coating the particles while they are
suspended in an upward-moving air stream
622 Source Book of Flavors
(Fig. 11-32). The particles enter the air
stream at the bottom of the coating chamber
and are lifted by the rapidly moving air
stream to the top of the chamber. At the top
of the chamber, air flow slows and the parti-
cles settle back to the sides of the chamber,
where they await recycling. The particles
can be coated by a fine mist of coating
material (e.g., fat) while suspended. Since
the particles are suspended as separate
granules and the coating is applied in a
thin film during several passes in a random
manner, a uniform film is readily applied in
this process. The primary disadvantages of
this technique are added cost (a batch pro-
cess) and the substantial amounts of coat-
ing that must be used to ensure complete
coverage (dilution of flavor and additional
cost).
Centrifugal Coating
An alternative coating process was ongi-
nated by Sparks (1987). Sparks has chosen
to put a granular material (e.g., spray-dried
THIN FILM"
..(\j• &• tz:-~~==:::::;:;:::::===~=~1
DROPLETS OF
PURE COAliNG
ENCAPSULATION BY SUSPENSION SEPARATION
FIGURE 11-34. Centrifugal coating system for spray-dried flavoring. (Sparks 1987)
flavoring) into a heated fat and then apply
this suspension to a rotating disk atomizer
(Fig. 11-34). The coating material breaks
into very small droplets, while the coated
particles are much larger in size. It is quite
easy to separate the two products (simply by
trajectory from the disk) and recycle the
unused coating material. This system offers
several advantages over air-suspension coat-
ing, including those associated with a con-
tinuous process, reduced process time and
reduced coating material application.
Sparks (1987) claims coating thickness rang-
ing from 3 to 200 11m and payloads of 25-97
percent.
MISCELLANEOUS PROCESSES
There are numerous other methods avail-
able for the encapsulation of flavoring mate-
rials (Gutcho 1976). These processes are,
however, of little commercial significance in
the industry today. Most often they involve
some unique way of dehydrating a flavor
ESTABLISHING PARTICLE S IZE
FOR PI.JRE COATING
li\.._
~COAliNG
FEED
..•.· - ~r~·
ROTATING DISK
~ FEED SUSPENSION

emulsion. One such technique is to spray
the flavor emulsion into a large volume of
gum arabic and then screen out the encap-
sulated flavor (Palmer 1975). Alternately,
an emulsion may be dehydrated by atomiz-
ing it into a dehydrating solvent. Patents
were issued to Pasin (1972) and Balassa
(1973) for a process in which an emulsion
was sprayed into low molecular weight
polyglycols. These polyglycols could range
in molecular weight from 106 (ethylene
glycol) to about 2,000. More recent work by
Kopelman and coworkers (1985, 1986) has
involved spraying flavor emulsions into
alcohol baths.
CONCLUSIONS
This is part of Chapter 11 has focused on
methods of commercial significance for the
encapsulation of food flavorings. The reader
is encouraged to go to the in-depth thesis
literature reviews of Bangs (1985) for more
information on flavor retention during spray
drying and Subramaniam (1984) for shelf
life considerations. Sparks (1981), Thies
(1987) and Dziezak (1988) have provided
excellent reviews of microencapsulation on
a broader scope.
References
Anandaraman, S. and Reineccius, G.A. 1986.
Stability of encapsulated orange peel oil.
Food Techno!. 40(11):88-93.
Anker, M. 1988. The Retention and Storage
Stability of Encapsulated Orange Peel Oil as
Influenced by Spray Drying Operating Param-
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Anker, M.H. and Reineccius, G.A. 1988.
Encapsulated orange oil: Influence of spray-
dryer air temperatures on retention and shelf-
life. In Flavor Encapsulation: ACS Symposium
Series 370, eds. S.J. Risch and G.A. Reinec-
cius, pp. 78-86. Washington, D.C.: Ameri-
can Chemical Society.
Arens, R.P. and Sweeney, N.P. 1969. Biliquid
column of shell material around fill liquid.
U.S. Patent 3,423,489.
Arneodo, C., Baszkin, A., Benoit, J.-P., and
Flavor Manufacturing 623
Thies, C. 1988. Interfacial tension behavior of
citrus oils against phases formed by complex
coacervation of gelatin. In Flavor Encapsula-
tion: ACS Symposium Series 370, eds. S.J.
Risch and G.A. Reineccius, pp. 132-147.
Washington, D.C.: American Chemical
Society.
Baisier, W. and Reineccius, G.A. 1989. Spray-
drying of food flavors V. Factors influencing
shelf-life of encapsulated orange peel oil.
Perf. Flavor. 13(4):1-4.
Balassa, L.L. 1970. Encapsulation of aromas and
flavors. U.S. Patent 3,495,988.
Balassa, L.L. 1973. Encapsulation process. U.S.
Patent 3,780,195.
Bangs, W.E. 1985. Development and Charac-
terization of Wall Materials for Spray Dried
Flavorings Production. Ph.D. Thesis: Univer-
sity of Minnesota.
Barnes, J.M. 1987. Encapsulation matrix compo-
sition and encapsulation containing same.
U.S. Patent 4,689,235.
Beck, E.E. 1972. Essential oil composition. U.S.
Patent 3,704,137.
Bradley, R.L. and Stine, C.M. 1963. Spray dry-
ing of natural cheese. Manu[. Milk Prod. J.
54(11):8.
Brenner, J., Henderson, G.H., and Bergensten,
R.W. 1976. Process of encapsulating an oil
and product produced thereby. U.S. Patent
3,971,852.
Brenner, J. 1983. The essence of spray-dried
flavors: The state of the art. Perf. Flavor.
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Chang, Y.l., Scire, J., and Jacobs, B. 1988.
Effect of particle size and microstructure
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Flavor Encapsulation: ACS Symposium Series
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pp. 87-102. Washington, D.C.: American
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Dziezak, J.D. 1988. Microencapsulation and en-
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136-148.
Emberger, R. 1981. Aspects of the development
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Walter de Gruyter.
Gutcho, M.H. 1976. Microcapsules and Micro-
encapsulation Techniques. Park Ridge: Noyes
Data Corp.
Inglett, G., Gelbman, P., and Reineccius, G.A.
1988. Encapsulation of orange oil: Use of
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oligosaccharides from a-amylase modified
starches of maize, rice, cassava and potato. In
Flavor Encapsulation: ACS Symposium Series
370, eds. S.J. Risch and G.A. Reineccius, pp.
26-36. Washington, D.C.: American Chemi-
cal Society.
Jones, D.M. 1988. Controlling particle size and
release properties: Secondary processing
technique. In Flavor Encapsulation: ACS
Symposium Series 370, eds. S.J. Risch and
G.A. Reineccius, pp. 158-176. Washington,
D.C.: American Chemical Society.
Kenyon, M.M. and Anderson, R.J. 1988. Malto-
dextrins and low-dextrose-equivalence corn
syrup solids: Production and technology for
the flavor industry. In Flavor Encapsulation:
ACS Symposium Series 370, eds. S.J. Risch
and G.A. Reineccius, pp. 7-11. Washington,
D. C.: American Chemical Society.
Kieckbusch, T.G. and King, C.J. 1977. Losses of
volatiles in the nozzle zone during spray dry-
ing. Pac. Chern. Eng. Cong. Proc. 2(1):216.
King, W., Trubiano, P., and Perry, P. 1976.
Modified starch encapsulating agents offer
superior emulsification, film foaming, and low
surface oil. Food Prod. Dev. 10(10):54.
King, A. 1988. Flavor encapsulation with algi-
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Reineccius, pp. 122-125. Washington, D.C.:
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Ma, Y.M. 1991. Investigation of the Correlation
between Glass Transition and Stability of
Flavor Microcapsules. M.S. Thesis: Univer-
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Miller, D.H. and Mutka, J.R. 1986. Preparation
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Patent 4,610,890.
Pagington, J.S. 1986. ~-Cyclodextrins. Perf.
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Palmer, E. 1975. Method for encapsulating
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Pasin, J.Z. 1972. Encapsulation process. U.S.
Patent 3,664,963.
Reineccius, G.A. 1991. Role of carbohydrates
in the encapsulation of food flavors. Food
Techno[. 45(3):144-149.
Reineccius, G.A. and Coulter, S.T. 1969. Flavor
retention during drying. J. Dairy Sci. 52(8):
1219.
Reineccius, G.A. and Bangs, W.E. 1985. Spray
drying of food flavors. III. Optimum infeed
concentrations for the retention of artificial
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Reineccius, G.A. and Risch, S.J. 1986. The
encapsulation of artificial flavors by ~­
cyclodextrin. Perf. Flavor. 11(4):1
Risch, S.J. and Reineccius, G.A. 1988. Spray-
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Rosenberg, M., Kopelman, I.J., and Talmon, Y.
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Schultz, T.H., Dimick, K.P., and Makower, N.
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1313.
Chapter 12
Flavoring Materials
Contributing to Taste
The majority of organic chemicals used in
the flavor industry and discussed in this
book are volatile and make their contribu-
tion to flavor via the olfactory system.
However, taste plays a role in virtually all
flavors and may make a most significant
contribution to some flavors in particular.
Most savory foods such as crackers, broths
or cheeses depend strongly on the taste
sensations. Even the most aromatic fruits
would fall a bit flat without the tartness
of acids or the sweetness of sugars. The
trigeminal responses of cooling menthol
and heat of spices are components of taste
that are key to many foods. There is little
question that taste is very important to
flavor in general. It is convenient to treat
these flavor adjuncts separately from the
organics used for their aromatic properties
and thus, this chapter will focus on the taste
(nonvolatile) constituents of flavor, since
the previous chapters have been devoted to
the aromatic components of flavor.
Taste is detected through the contact of
certain water-soluble compounds with the
taste buds on the tongue. Traditionally, it is
widely accepted that there are four primary
taste sensations: sweet, sour, salt and bitter;
however, many accept umami (the mouth-
feel associated with the flavor potentiators
626
MSG and the S'nucleotides) and metallic as
basic taste sensations (Beauchamp 1990).
This classification implies a certain mis-
leading simplicity to the sensation of taste.
The taste sensations are not so simple. For
example, within the taste of acid (or tart-
ness), there is a very broad range in onset,
aftertaste and sensory character between
the acidulants. One must match the par-
ticular taste of lactic acid to fermented dairy
flavors, citric acid to citrus flavored products
and malic acid to apple, etc.
This chapter will be organized into a
discussion of the substances responsible
for these basic tastes. The chemistry and
sensory properties of each taste contributor
will be presented.
SWEETNESS
The sweet taste is produced by several
different kinds of substances, most of which
are nonionic:
a. Sugars (monosaccharides and disac-
charides)
b. Polyhydric alcohols (glycols, glycerol)
c. a-amino acids
d. Synthetic sweeteners
These nonvolatile compounds differ widely
in molecular constitution, and attempts to
 Flavoring Materials Contributing to Taste 627

explain sweetness in terms of functional plants. It is a six-carbon reducing sugar and

groups or molecular architecture have met thereby participates in color and flavor
with little success (Schallenberger 1990; formation during heating. It is generally
Walters, Orthoeler and DuBois 1991). manufactured by completely hydrolyzing
starch. Glucose is both less soluble and less
sweet (0.5-0.7 x) than sucrose (see Table
Simple Sugars
12-1). This limits its usefulness in foods as a
The most widely occurring natural sweet- sweetener. It is, however, used commonly
eners are the class of crystalline polyhydroxy in the flavor industry as a reactant in pro-
carbohydrates known as sugars. Their cessed flavors, since it participates readily in
chemistry has been thoroughly researched Maillard browning and is very inexpensive.
over the past century, and reference may be
made to any standard textbook on organic Fructose (Levulose or Fruit Sugar)
chemistry or, more specifically, Walters,
Orthoeler and DuBois (1991) and Grenby
(1989). Chemically, these materials are
either monosaccharides with 5 or 6 carbon Fructose is a six-carbon reducing sugar
atoms or disaccharides with 12 carbon found in many foods naturally, but is seldom
atoms. Trisaccharides (C 18 ) and tetrasac- found in great quantities. It is a white to
charides (C24 ) are of little importance as cream-colored, odorless, crystalline powder
sweeteners. The principal sugars and their that is hygroscopic. It is one-half of sucrose,
relative sweetness are given in Table 12-1. so if there is significant hydrolysis of sucrose
in a food system, one will find fructose. It is
Glucose (Dextrose or Grape Sugar) important to the food industry because of
its high level of sweetness and solubility.
While relative sweetness depends upon the
medium as well as the concentration (see
Glucose is a colorless, odorless crystalline Table 12-1), fructose, in solution, is gen-
substance usually available as a white erally considered to be significantly sweeter
crystalline powder. It is the most widely (1.8 x) than sucrose. It is manufactured by
distributed sugar in nature and serves as a hydrolyzing starch to glucose and then
direct energy source in both animals and enzymatically isomerizing the glucose to
fructose (Bernetti 1990).
TABLE 12-1. Relative Sweetness (RS) of Sugars
(w/w%) Sucrose
Sugar SolutionRS Crystalline RS
(Cane or Beet Sugar)
13-D-Fructose 100-175 180 C12H2zOu
Sucrose• 100 100
a-D-Glucose 40-79 74
13-D-Glucose <a-Anomer 82 Sucrose consists of hard white, dry,
a-D-Galactose 27 32 odorless crystals whose physical appear-
13-D-Galactose 21 ance depends on the grade produced in
a-D-Mannose 59 32 the finishing stages of refining (Junk and
13-D-Mannose Bitter Bitter
a-D-Lactose
Pancoast 1973). It is prepared by crushing
16-38 16
13-D-Lactose 48 32 and extracting sugar cane (Saccharum
13-D-Maltose 46-52 officinarum L.) or sugar beet (Beta vulgaris
Raffinose 23 1 L.) with water, evaporating the crude brown
Stachyose 10 extract to a consistency suitable for further
• Reference sugar, arbitrarily given a value of 100. refining. In the latter stages, the white
628 Source Book of Flavors
TABLE 12-2. Solubility of the simple sugars in aque-
ous solution at various temperatures
Solubility in g/100 g
Sugar zoe 40C 60C
Fructose 78
85 91
Sorbitol 72 78 85
Xylitol 63 74 84
Glucose 45 60 78
Lactose 12 23 34
and brown sugars are separated from the
mother-liquors or molasses, with these
individual products being offered in num-
erous grades, depending on their end use.
Sucrose is very soluble in water (Table
12-2) and sugar tables relating the per-
centage concentration (quoted as degrees
Brix) to the refractive index, degrees
Baume, and the specific gravity of the
solution is widely used throughout the food,
beverage and sugar confectionery industries
(Ockerman 1978).
Sucrose is a disaccharide consisting
of two linked hexose units, glucose and
fructose. Its sweetness in terms of temporal
effect and character is used as the standard
against which all other sweeteners are
measured.
It is a nonreducing sugar, which means
that it is relatively nonreactive during
heating. The glycosidic bond holding the
two component sugars together is weak,
however, and thus low pH and/or heating
will result in some hydrolysis, yielding the
two reducing component sugars, which are
reactive. The limited reactivity of sucrose
must be considered when changing sugar
type in product formulations that are
thermally processed, since the replacement
sugar is most likely reducing (e.g., fruc-
tose), and will develop more color and
flavor than the sucrose. A review on the use
of sucrose as a sweetener was published by
Godshall (1990).
Invert Sugar
Invert sugar is a mixture of glucose and
fructose in nearly equal proportions. It is
made by the acid hydrolysis or enzymatic
(invertase) conversion of sucrose. In the
conversion of sucrose to invert sugar, the
optical rotation changes from a positive
rotation (due to the strong effect of fruc-
tose), which is why it is called "invert"
sugar. Most invert sugar used in confection-
ery manufacture is prepared in situ as re-
quired, or it may be purchased as 70 percent,
75 percent or 80 percent concentrations.
Lactose
(Milk Sugar)
C12Hzz011 · HzO
Lactose is a hard white, odorless, crystal-
line substance usually available as a fine
white powder. It is derived from milk whey
or skimmed milk by concentration and
crystallization. Lactose is a disaccharide
consisting of glucose and galactose, and
exists in two anomeric forms of which the
a-form predominates. It is a reducing sugar,
has low solubility in water and is not par-
ticularly sweet (see Tables 12-1 and 12-2).
The low level of solubility and sweetness
severely limits the usefulness of lactose in
the industry. Low solubility may result in
the crystallization of lactose from a food
product, causing a "sandy" defect. This is
occasionally observed in ice cream. The
"sandy" defect is extremely objectionable,
since the sugar crystals do not dissolve
in the mouth and truly give a feeling of
having sand in the mouth. The relative
lack of sweetness removes lactose from the
role of sweetener in many typical sugar
applications.
Lactose suffers from an additional prob-
lem, that much of the world is "lactose
intolerant." Only a small milk drinking
segment of the world's population retains
the enzyme necessary to hydrolyze lactose
in the gut to the component sugars so that
the body can metabolize it for energy. In
non-milk drinking populations, the lactose
passes into the lower digestive tract intact

and there is utilized by normal microflora to
produce large quantities of gas and other
intestinal effects. The effect is sufficiently
intense in most individuals so that they do
not consume significant quantities of milk
fresh or as an ingredient.
Maltose
(Malt Sugar)
C12H2zOu · HzO
Maltose is a disaccharide comprised of
two molecules of glucose. It is obtained by
acid and enzymatic (diastase) conversion
of starch and exists as colorless, odorless
crystals or as a fine white powder. The
hydrated form loses its molecule of water by
drying at 100 degrees Celsius. It is less sweet
than sucrose.
Sugar Alcohols
There are a few sugar alcohols available on
the commercial market (e.g., sorbitol,
xylitol and dulcitol). These sugar alcohols
are generally less sweet than sucrose or their
aldose counterparts. They find application
in the food and flavor industry for certain
label claims. For example, a food manu-
facturer can sweeten or bulk a food through
the use of the sugar alcohols and yet claim
"no added sugar." These sweeteners are
not considered sugars in the letter of the
law, despite the fact that they are used to
sweeten a food.
The sugar alcohols also find application in
claims for reduced dental carries. While the
sugar alcohols are slowly fermented by
bacteria in the mouth, the rate is substan-
tially less than the common sweeteners and
thus less dental carries result from products
containing sugar alcohols. The primary
product involved is sugar-free chewing gum.
Soribtol
Flavoring Materials Contributing to Taste 629
Sorbitol is a hexahydric sugar alcohol
having the configuration of glucose. It
occurs naturally in small quantities in many
fruits. It is prepared commercially by the
catalytic hydrogenation of glucose. It is a
white hygroscopic powder, which is soluble
in water and has a sweet taste.
Mannitol
(Manna sugar)
C6Hl406
Mannitol is a hexahydric sugar alcohol,
which is isomeric with sorbitol. It is a white,
odorless crystalline powder soluble in water
and pleasantly sweet.
Xylitol
Xylitol is a pentose sugar alcohol, which
occurs naturally in raspberries, straw-
berries, plums and some vegetables. It is
produced commercially by enzymatic or
microbiological conversion of xylose-rich
precursors (e.g., birchwood chips) (Moore
1977). It is a white, odorless, crystalline
powder having a sweetness equivalent to
that of sucrose.
Foods Used as Sweeteners
Honey
Honey is a sweet syrupy liquid obtained
from the hives of the honey bee (Apis
mellifera). It is of variable composition
comprising a mixture of fructose (33-40
percent) and glucose (32-42 percent) with
15-20 percent of water and significant
aromatic components, which give the
product its distinctive odor and flavor.
Maple Sugar
Maple sugar consists of a mixture of
glucose, fructose and sucrose, and is ob-
tained from the sap of the sugar maple
(Acer saccharum L.) in early spring. The
sap is concentrated by boiling to give maple
syrup and may be crystallized to give maple
sugar. Maple has a distinctive flavor and
630 Source Book of Flavors

maple syrup was once a staple sweetener of to that of an equivalent concentration of

American Indians and the early colonists.
Its popularity has been maintained, and
considerable quantities are produced each
year in Canada and the northeastern United
States.
Molasses
The definition of the designation "mo-
lasses" differs with the source material and
the producing region. It is a by-product of
both cane and beet sugar refining. In the
sugar cane industry, molasses is the syrupy
mother-liquor remaining after the sugar has
been removed by concentration and crystal-
lization. Two main grades are recognized:
"first molasses," remaining after the initial
crystallization stage, and "blackstrap mo-
lasses," which represents the final stage
of the refining process. In the beet sugar
industry, only the final residual mother-
liquor is called "molasses."
The composition of this product is very
variable.
Corn Syrup
Corn syrup is obtained by hydrolysis of corn
starch via acid, enzymes or a combination
of both under controlled conditions. The
composition of the end product depends on
the reaction time and acid or enzyme con-
centration. The products are characterized
by the term "dextrose equivalent." Dex-
trose equivalent refers to the amount of
reducing power the solution has compared
glucose. Thus, a solution of glucose has
a DE of 100 by definition. A partially
hydrolyzed starch will vary from a DE of
essentially 0 (starch) to 100 (pure glucose).
One should note that a value of 50, for
example, does not necessarily mean that the
solution is made up of maltose (although
this solution would have a DE of 50), but
that the reducing power of the combination
of sugars resulting from hydrolysis has a
reducing power that is 50 percent of an
equivalent glucose solution.
Corn syrups are used extensively in food
processing, and in the United States are
defined as "purified concentrated solutions
of nutritive saccharides obtained from corn
starch and having a dextrose equivalent of
20 or more." By selecting the hydrolytic
conditions, corn syrups having unique
carbohydrate compositions can be pro-
duced. By using a combination of acids and
enzymes, corn syrups having almost any
combination of glucose, maltose and higher
polysaccharides can be produced (Table
12-3).
High Intensity Sweeteners
Natural Sweeteners
The use of naturally sweet materials has
been an essential feature of foods for
generations. The following (see Sardesai
and Waldshan 1991) are of particular
interest:

TABLE 12-3. Composition of Representative Corn Syrups

Saccharides, %
Type of Dextrose
Conversion Equivalent Mono- Di- Tri- Tetra- Penta- Hexa- Hepta- Higher

Acid 30 10.4 9.3 8.6 8.2 7.2 6.0 5.2 45.1

Acid 42 18.5 13.9 11.6 9.9 8.4 6.6 5.7 25.4
Acid-enzyme 43 5.5 46.2 12.3 3.2 1.8 1.5 29.5 1
Acid 54 29.7 17.8 13.2 9.6 7.3 5.3 4.3 12.8
Acid 60 36.2 19.5 13.2 8.7 6.3 4.4 3.2 8.5
Acid-enzyme 63 38.8 28.1 13.7 4.1 4.5 2.6 8.2 1
Acid-enzyme 71 43.7 36.7 3.7 3.2 0.8 4.3 7.6 1
1 Includes heptasaccharides.
 Flavoring Materials Contributing to Taste 631

TABLE 12-4. The Taste Properties of a-Amino Acids in Aqueous Solution (0.5%)

Levorotatory Dextrorotatory
Optically Active
Alanine Sweet Insipid
CH3CH(NH 2 )COOH
Histidine Insipid Sweet

Leucine Bitter Sweet

(CHa),CHCH 2CH(NH,)COOH
Phenylalanine Bitter Sweet

o-CH,CH(NH,)COOH

Tryptophan Bitter Sweet

~C·CH 2 CH(NH,)COOH

~)H
N
H

Tyrosine Bitter Sweet

OH-Q-cH,CH(NH,)COOH
Optically Inactive
Glycine
(a-aminoacetic acid) Sweet
NH,CH,COOH

Amino Acids times sweeter than sucrose and this amino

Almost all of the amino acids related to
foods are a-amino carboxylic acids, are
white crystalline compounds and are water-
soluble. The amino acids are not uniformly
sweet; indeed, some are insipid or bitter. It
was observed long ago that the optically
active D-enantiomorphs are sweet, whereas
the L-forms are not (Meilgaard et al. 1987;
Erickson and Fagerson 1976). This has been
used as a basis for classification, but it is
most likely that the sweet character is
determined by stereostructure rather than
by optical activity. The more important
amino acids are listed in Table 12-4. Few
have any specific effect upon the taste of the
product, but some specific patterns of amino
acids may intensify taste (Kirimura et al.
1969).
D-Tryptophan is reported as being 35
acid has been used to develop a synthetic
derivative, 6-chloro-D-tryptophan, which
is claimed to be 1000 times sweeter than
sucrose (Anon. 1974a,b).
Glycyrrhizin
Licorice root extracts (block juice) have
long been used as an appealing flavoring in
candy manufacture. Its sweetness is due to
the presence of glycyrrhizin, which is the
calcium and/or potassium salts of glycyr-
rhizic acid. This is a glucoside, which on
hydrolysis yields glycyrrhetic and glucuronic
acids. Glycyrrhizin is extremely sweet and is
claimed to be up to 50 times sweeter than
sucrose, although the associated licorice
flavor makes direct comparison difficult.
Licorice root ( Glycyrrhiza glabra L.)
contains varying amounts of glycyrrhizin
632 Source Book of Flavors
depending on source but ranging from 6 to
20 percent; the commercial block juice
contains 14 to 20 percent.
Commercial glycyrrhizin is the am-
monium salt of glycyrrhizic acid. This is
water-soluble, but it is inactivated in acid
media due to the precipitation of the acid
form.
Miraculin
Miraculin is a glycoprotein extracted from
the berries of a West African bush (Syn-
sepalum dulcijicum). An extract of this fruit,
known as miracle fruit, has the unusual
property of tasting intensely sweet but only
in the presence of acids.
Monellin
Monellin is an intensely sweet component
of serendipity berries (Dioscoreophyllum
cumminisii). It is approximately 3,000 times
sweeter than sucrose (Morris and Cagan
1972).
Osladin
Osladin is an intensely sweet component
obtained from the rhizomes of Podophyllum
vulgare L. (Jizbe et al. 1971).
Phyllodulcin
Phyllodulcin is obtained from the dried
leaves of Japanese Hydragea macrophylla
Seringe. It is 200-300 times sweeter than
sucrose (Ariyoshi 1974).
Stevioside
This is a triterpene glycoside, which is
readily extracted from the leaves of Stevia
redandiana, an herb grown in South
America. It is approximately 300 times
sweeter than sucrose. It has a slight
menthol-like aftertaste. It is approved as a
sweetener in other parts of the world, but
has no legal status in the U.S. It is permitted
for use in food in Japan, where the product
is manufactured commercially.
Thaumatin I and II
Thaumatin is a mixture of sweet-tasting
proteins extracted from the African katemfe
fruit. It is 1,500-2,500 times as sweet as
sucrose. It is slow in the onset of sweetness
and carries a long-lasting sweet aftertaste. It
has not been approved as of yet by the
FDA, but has been deemed GRAS by
FEMA. This means that it can be used as a
flavoring and may be used in chewing gum.
Higginbotham (1986) has presented an
article on its use in foods.
Synthetic Sweeteners
Many substances having an intensely sweet
taste are produced synthetically and have
been widely used as sweeteners in processed
dietetic foods, confectionery, soft drinks,
etc. (Stamp 1990, Sardesai and Waldshan
1991). The growing concern for being
overweight has resulted in very rapid growth
in the reduced calorie market in the U.S.
This has stimulated the development of a
host of new high-intensity sweeteners. The
following are of substantial interest: as-
partame, saccharin, cyclamates, Alitame
(L-alpha-aspartyl-D-alanine), Acesulfame
K and Sucralose (trichloro derivative of
sucrose-Stamp 1990).
Saccharin
0
II
~c'~-Na
~802
saccharin sodium saccharin
Saccharin was first made in 1879 by Remsen
and Fahlberg. This odorless compound is
300 to 550 times sweeter than sucrose (Table
12-5). The acid compound is only sparingly
soluble in cold water (1 in 300), but is much
more so in boiling water (1 in 25). Many
persons can taste as sweet 1 part of this
compound in 70,000 parts of water. Sac-
charin melts with some decomposition at
436.4°F (225°C) and sublimes on further
heating. The sodium and ammonium salts
are sold as soluble saccharins. These are
 Flavoring Materials Contributing to Taste 633

TABLE 12-5. The Relative Sweetness of Nonsugar TABLE 12-5. Continued

Sweeteners (Not Necessarily Approved -------------------
for Food Use at This Time). (Heath Sweetness Compared
1981) with Sucrose rated
as 1
Sweetness Compared
with Sucrose rated p-Nitrosuccinalilide 350
as 1 p-Methoxymethylnitrobenzene 500
1-Bromo-5-nitroaniline 700
Natural origin Perillic aldehyde oxime 2,000
Phyllodulcin (Hydragea 200-300 (perillartine)
macrophylla) 1 5-Nitro-2-n-propoxyaniline (P- 4,000
Stevioside (Stevia rebandiana) 2 300 4000)
Thaumatin I and II 1,600 ~-Neohesperidine 6,000
(Thaumatocus danielli) 3 dihydrochalcone 8
Monellin (Dioscoreophyllum 3,000
cumminisii) 4 References:
1 Arioyoshi, Y. 1974. Taste and chemical structure (2). Kagaku
Osladin (Podophyllum 3,000
To Seibutsu 12 : 274 (Japanese).
vulgare) 5 2 Farnsworth, N .R. 1973. The current state of sugar substitutes.

Synthetic6 Cosmet. Perfum. 88(7):27-26.

3 Van der Wei, H. and Loeve, K. 1973. Isolation and
3-Methylcyclopentylsulfamate 15
characterization of Thaumatin I and II the sweet-tasting
p-Anisylurea 18
proteins Thaumatococcus danielli Benth. J. Biochem. 31:221.
Sodium cyclohexyl sulfamate 30 4 Morris, J.A. and Cagan, R.H. 1972. Purification of monellin,
(cyclamate) the sweet principle of Dioscoreophy/lum cumminisii. Biochem.
Aspartame7 150-200 Biophys. Acta. 261: 114.
Methoxy-2-amino-4- 167 5 Jizba, J. et al. 1971. Structure of osladin, the sweet principle

nitrobenzene of the rhizomes of Podophyllum vulgare L. Tetrahedron Lett.

p-Ethoxyphenylurea (Dulcin) 200 1329.
6 Beck, K.M. 1975. Practical considerations for synthetic
p-Methylsaccharin 200
6-Chlorosaccharin 300-550 sweeteners. Food Prod. Dev. 9(4):47-54.
7 Searle Biochemicals. (Undated) Aspartame. Tech. Bull. 600
Sodium benzosulfimide 300
(060473). Searle Biochemicals. Division of G.D. Searle,
(saccharin)
Arlington Heights, Illinois.
n-Hexylchloromalonamide 300 8 Inglett, G.E. et al. 1969. Dihydrochalcone sweeteners,
Naringin dihydrochalcone 300 sensory and stability evaluation. J. Food Sci. 34: 101.
2-amino-4-nitrotoluene 300

readily soluble in water and it is in this form a provisional basis. It currently is permitted
that the material is most generally used. The in over 80 countries of the world.
high intensity of sweetness and excellent
stability in virtually all food applications Cyclamates
have made this sweetener very attractive to
the industry. However, if used in excess, the
taste is markedly bitter rather than sweet
and at all dilutions it leaves an unpleasantly
lingering aftertaste (Table 12-6), which is
considered to reduce market acceptance.
Action was taken by the FDA to ban sodium cyclamate calcium cyclamate
saccharin in 1971, based on safety studies
conducted by the National Academy of The sodium and calcium salts of cyclo-
Sciences. Additional studies have shown hexanesulfamic acid, which itself has a
that saccharin poses minimal health risk at sweet-sour taste, enjoyed considerable
the normal levels of consumption and thus it popularity before their almost universal
has been permitted to be used in the U.S. on rejection on toxicological grounds in 1969-
634 Source Book of Flavors

1970. At the time, the tests were severely
criticized and the suspected carcinogenicity
of the cyclamates has never been satisfac-
torily confirmed. However, their use is still
either banned or restricted in many coun-
tries of the world (permitted in 40 countries).
It is anticipated that the FDA will permit
cyclamates to again be used in the U.S.
market beginning in 1992. The cyclamates
are odorless and have a sweetness some
30 times greater than sucrose without the
unpleasant aftertaste associated with sac-
charin. The synergistic effect of mixtures of
saccharin and cyclamate was used in the
formulation of soft drinks (10: 1 ratio with
saccharin). This blend eliminated the bitter
taste associated with sweetening solely with
saccharin.
L-ASPARTAME-L-PHENYLALANINE
METHYL ESTER
(ASPARTAME)
There is little question that aspartame
(trade name NutraSweetR) has become the
U.S. market leader in the high-intensity
sweetener market. Aspartame is 150 to 250
(generally cite 200 x) times as sweet as
sucrose in most applications. It has good
sensory properties with no residual after-
taste (Table 12-6). Aspartame is a dipeptide
composed of aspartic acid and phenylalanine
(N-L-alpha-aspartyl-L-phenylalanine-1-
methyl ester). Thus, it is readily metabol-
ized and used as energy, but the very low
levels of it is a food product contribute an
insignificant amount of calories to the diet.
Aspartame is limited in application since
it is unstable in aqueous solutions during
prolonged storage and to heating (either
hydrolysis of the methyl ester or participa-
tion in the Maillard reaction). Thus, one
does not see it used in food products that
receive substantial heat treatment (e.g.,
baked goods). Stability is pH-related, being
more acid stable. However, significant
breakdown occurs even in low pH applica-
tions such as beverages. The shelf life of a
dietetic beverage is determined to some
extent by the limited stability of the as-
partame. An additional problem with
aspartame is that it will react with aldehydes
in flavors to form Schiff's bases. This effec-
tively reduces flavor strength as well as
sweetness. This problem is very significant
in the combined use of cinnamon (cinnamic
aldehyde) or cherry (benzaldehyde) with
aspartame to flavor chewing gum or car-
bonated beverages, respectively.

TABLE 12-6. Mean Attribute Scores for Four Sweeteners•

Sample Overall Liking Sweetness Intensity Aftertaste Presence Flavor Strength

Sucrose 6.1 A 7.0A,B 4.4 A 6.9A

Aspartame 4.0 6.3A,B 6.7 6.4 A
Acesulfame K 1.9B 3.0 6.4 3.2
Aspartame/Acesulfame K 3.1 5.7B 6.2 4.5
Aspartame/Saccharin 3.4 4.1 5.9 4.9
Unsweetened 1.8B l.lC 3.6A 2.4
a For each attribute (column), samples having the same letter (or no letter) are not statistically significantly different. Any two
samples with different letters are significantly different. Values are mean hedonic scores based on panelist liking (9 is most
postive score, n = 23).
 Flavoring Materials Contributing to Taste 635

Acesulfame K Alitame is the trade name of L-alpha-aspartyl-

N- (2, 2, 4, 4,- tetramethyl- 3- thietanyl)- D-
HC\;o....._// 0
alaninamide hydrate. Alitame is 2,000-
3

I r=o
·N:. I<
0 (another amino acid based sweetener) that
ACESULFAME K
Acesulfame K is approximately 200 times
sweeter than sucrose and is very stable. It
was first approved for food use in 1988 in the
U.S. and has been approved for use in 28
other countries. While Acesulfame K has
the advantage of excellent stability, it
suffers in sensory quality. Acesulfame
K received the lowest sensory liking of
the sweeteners informally evaluated and
presented in Table 12-6. Acesulfame K
generally is perceived to have a slight bitter
taste.
Sucralose
3,000 times as sweet as sucrose, depend-
ing upon concentration and application.
It offers the advantage over aspartame
it is stable to heating and thus may meet
some of the applications that aspartame
currently does not (Freeman 1989). Alitame
is currently not permitted for use in the
U.S., but a petition is before the FDA for
approval for broad application. Alitame is
claimed to have excellent sensory properties
and be sufficiently stable to be used in
baking.
ACIDULANTS
The majority of acids used in the food
industry are organic in nature. Phosphoric
acid is the only inorganic acid used to impart
tartness to a food. However, inorganic acids

P
such as hydrochloric acid may be used in
HOCH2 food processing (e.g., manufacture of HVP)
O C~ICHO to accomplish major pH changes. Hydro-
OH H chloric acid has the advantage of yielding an
0 edible salt (i.e., table salt) when neutralized
OH HO CH2CI
by sodium hydroxide. The structures,
physical and chemical properties, and legal
SUCRALOSE status of the common food acids are sum-
marized in Table 12-7. The reader is en-
Sucralose is a trichloro derivative of sucrose couraged to read the review of Dziezak
and is about 600 times sweeter than sucrose. (1990) for more detail.
It has received limited approval for use in The use of acidulants in food products
the U.S. It is substantially more stable than and beverages is of considerable importance
the parent sucrose and appears to be well- for the following reasons:
suited to many food applications (Nabors
a. Optimum acidity in fruit-flavored
and Gelardi 1991).
beverages, table desserts, sugar con-
fectionery, etc., enhances and mod-
Ali tame
ifies the flavor profile.
b. In diluted fruit-based products, the
correct acidity/sugar balance partially
reconstitutes the body of the original
flavor.
c. For preservation, acid media retard or
inhibit the growth of spoilage bacteria
ALITAME and yeasts.
 0\
TABLE 12-7. Structure, Regulatory Status, and Key Physical and Chemical Properties of Several Acidulants (Dziezak 1990) <...l
0\

Chemical and physical properties

V'J
0
Ionization Melting point Solubility (g/100 Hygro- Taste charac- ...,r::
Acid Structure CFR" constant(s) pK. Physical form ("C) mLwater) scopicity teristics n
C1l

Acetic acid 0 184.1005 5 4.75 -8.5 b 1::0

1.76 x w- Clear Soluble - Tart and sour 0
(GRAS) at 25°C colorless 0
II :>;"
CH 3-C-OH liquid 0
.....
Adipic acid 0 184.1009 K, = 3.71 x 10-s 4.43 Crystalline 152 1.9 gat 20°C Low level Smooth ::!1
I (GRAS) K2 = 3.87 X 10-6 5.41 powder 83g at 90°C of hygro- lingering ~
0
CH 2-CH 2-C-OH at 25°C scopicity tartness; :;!
0 complements
I II grape flavors
CH 2-CH2-C-OH

Citric acid 0 182.1033 K 1 = 7.10 X 10- 4 3.14 Crystalline Anhydrous, 181 gat 25°C Moderately Tart; delivers a
I (GRAS) K2 = 1.68 X 10- 5 4.77 powder 153 hygro- "burst" of
CH 2-C-OH K3 = 6.4 X 10- 7 6.39 Hydrous, 208g at 25°C scopic tartness
0 at 200C 135-153
I I
HO-C-C-OH
0
I I
CH 2-C-OH

Fumaric 0 172.350 K 1 = 9.30 X 10- 4 3.03 White 286 0.5g at 20°C Nonhygro- Tart; has an
acid I (Food K2 = 3.62 X 10- 5 4.44 granules or 9.8 gat 100°C scopic affinity for
HO-C-CH 0 additive) at !sac crystalline grape flavors
II I powder
HC-C-OH

Glucono 184.1318 1.99 X 10- 4 (for 3.7 White 153 59g at 25°C Nonhygro- Neutral taste
delta- o~c=l (GRAS) gluconic acid) crystalline scopic with acidic
lactone Ht-OH powder aftertaste
when
HO-CH 0 hydrolyzed

+ouj
HC
I
CH 20H
Lactic acid OH 184.1061 1.374 x w- 4 3.86 Liquid, also 16.8 Vcry soluble Acid
0 (GRAS) at 25°C available in
II dry form
CH 3-CH-C-OH

Malic acid 0 184.1069 K1 = 3.9 X 10- 4 3.40 Crystalline 132 62g at 25°C Nonhygro- Smooth
II (GRAS) K2 = 7.8 X 10-o 5.11 powder scopic tartness
HO-CH-C-OH at 25°C
0
I I
CH 2-C-OH

Phosphoric H,P0 4 182.1073 K1 = 7.52 X 1o-' 2.12 Liquid Very soluble in Acrid
acid (GRAS) K2 = 6.23 X w-x 7.21 hot water
K, = 2.2 X 10-u 12.67
K 1 and K2 at
25°C; K, at
I8°C

Tartaric 0 184.1099 K1 = 1.04 X 10-' 2.9S Crystalline 168-170 147g at 25°C Non hygro- Extremely tart;
acid II (GRAS) K2 = 4.55 X 10- 5 4.34 powder scopic augments
HO-CH-C-OH at 25°C fruit flavors,
especially ::!1
I grape and
~
HO-CH-C-OH lime 0
::::!.
I ::l
{)q
0
~
Pl
"Title 21 of the Code of Federal Regulations (FDA, 1988) ;;
::::!.
"Not applicable a
"'
("')
0
::l
....
::::!.
cr'
c
:::.'.
::l
{)q
....
0

~
;;

0\
1..-J
-.)
638 Source Book of Flavors
d. A lowering of pH slows down or even
stops the action of many natural
enzymes that may cause off-flavors
and discoloration.
e. Acids enhance the action of many
natural antioxidants.
f. In pectin gels, the correct level of
acidity is necessary to achieve a good
gel strength.
g. As a source of "dry" acid in baking
powders.
h. The correct pH is essential for stabi-
lization in wine processing.
1. Metal chelation in the control of
oxidative processes.
Most fruits contain natural acids that
contribute essentially to the flavor profile.
The use of added acidulants is necessary
when one is employing an imitation fruit
flavor that is intrinsically neutral; otherwise,
the correct flavor impression is not achieved
in the end product and the resulting effect is
very different from that of the natural fruit.
All flavoring acids used in foods were
originally of natural origin (e.g., tartaric
acid and citric acid from fruits; lactic acid
from soured milk; acetic acid from bacterial
oxidation of wine, etc.). Most of them are
now manufactured synthetically to speci-
fications in the Food Chemicals Codex,
although some are still produced more
economically from natural products (e.g.,
tartaric acid and tartrates from grape juice).
Taste Interrelationships
As with salt and sugar, there are several
interrelationships between the prime tastes
involving acids and sourness. Sugar gen-
erally reduces the tartness of acids, the
degree of reduction being broadly similar
irrespective of the nature of the acid or
sugar used. The opposite effect is not nec-
essarily the case-e.g., hydrochloric and
acetic acid. Vinegar certainly reduces the
sweetness of glucose, but does not signi-
ficantly affect that of sucrose. The sweetness
of sucrose tends to be somewhat intensified
by lactic, malic, citric and tartaric acids-a
fact of importance in the formulation of
many fruit-based products.
Organic Acids Used in Food Flavorings
One must generally use the acid found in the
food product naturally in order to make a
flavor of the same name. For example,
acetic acid would be used to make a flavor-
ing for a salad dressing (vinegar flavor) or
citric acid to make a citrus flavoring. While
we view each of the acids as giving an "acid"
taste, the sensory character, intensity,
longevity, aftertaste, etc., are unique for
each acid (Dziezak 1990). Thus a food
flavoring will generally have to be formu-
lated with the acid normally found in a food
to properly simulate the flavor of that food.
Acetic Acid
Pure glacial acetic acid is produced com-
mercially by numerous processes, but
principally by the oxidation of either
acetaldehyde or butane, as a reaction pro-
duct of methanol and carbon monoxide
or by the neutralization of pyroligneous
acid with lime, separation of the precipi-
tated calcium acetate, reacidification and
distillation.
Glacial acetic acid is specified in the Food
Chemicals Codex. It is a clear, colorless
liquid having a pungent, characteristic odor
and, when well diluted with water, an acidic
taste. Glacial acetic acid is used very little in
the flavor industry. Vinegar instead serves
this purpose. The term "vinegar" has dif-
ferent meanings in different countries: In
the United States the designation, without
other qualification means "cider vinegar";
in the United Kingdom "malt vinegar" is
implied; whereas in European countries
"wine vinegar" would be supplied. The
flavor character of malt vinegar is coarse
when compared with that of wine or cider
vinegars, which have a more pleasing
character.
The spiced vinegars are also very popular
and these may be formulated to suit any
TABLE 12-8. Occurrence of Acids in 30 Fruits and Vegetables

»
....
» .... »
.... ...., »
....
.... » Q) » » E
....
Q)
.... ,J:J .... ...., ....
Q)
....
Q)
....
.... ,J:J
...., .g OS ....
Q)
....
Q)
·s.... Q) ....
,J:J s::: ,J:J Q) ,J:J
Q) 0
u
OS
u
s:::
OS ,J:J Q)
00
»
.... ,J:J s:::
OS Q)
'-
Q) Q)
s:::
0 Q) ..<::
-a
Po
OS i!: ,J:J
'§
u
..., 8....
..<:: ....,0 OS
,J:J
-"'u= Q) .... s::: .... 00 Po Po ~ u Q) Po s::: u 00 OS
-a ·;::::
0 s::: OS ~ » Q)
OS .... 0 OS OS E OS OS OS 00 OS 0
8.... OS ..., ~
s::: ~
8~
Po Po > OS ..<:: .... ~ .!!!' .... .... Q) E .... Q) ....,.... OS Q) .... OS Q) ..<::
< < < c:o a:i a:i ~ u u u .... 8 C.!l C.!l .....:l ;.::l 0 p.. i:i:: ~ 00 ~ c:o c:o u ;:;s p.. & ~
Acid
Acetic • •
Aspartic • •
Benzoic •
Citric • P' p • p p • p p p p p • p p p • p p p p p p p p
iso-Citric • p • • p
Citramalic • • •
Formic •
Fumaric • • • • • •
Galacturonic • • •
Glucuronic • • •
Glyceric • • • • • •
Glycolic • • • • • •
a- Ketoglutaric •
Lactic • • •
Lactoisoci tric •
Malic p p p p • • p p * * * • p • • • p p p • • p p p p p p
Oxalacetic * • *
Oxalic • • * • * • • • • • • • p
Pyruvic • • •
Quinic • * • * * • • • • • •
Shikimic • * * * • * * *
Succinic * • • * * * • * • •
Tartaric p • • p * p • • •
'Principal acid present.
Sources: Gardner (1966); Ulrich (1970).
640 Source Book of Flavors
particular product. Originally, they were
prepared by steeping the appropriate herbs
and spices in vinegar for long periods; today
they are more readily made from herb- and
spice-essential oils and extracts.
The use of vinegar in pickles, sauces,
relishes, etc., is universal, but apart from its
preserving properties in such products,
vinegar conveys a sharp piquancy and also
acts as a carrier of other aromatic notes to
the nose. Vinegar is produced from a wide
range of substances capable of producing
alcohol by yeast fermentation (e.g., cider,
wine, fruit juices, sucrose, glucose, malt,
etc.). The alcohol produced in this initial
stage is then converted into acetic acid by
acetobacter fermentation. The acetic acid
content of the vinegar is expressed as
"grain"-with a 60 grain vinegar being
6 percent acetic acid.
Adipic Acid
Adipic acid is produced commercially by the
oxidation of cyclohexanol. It is an odorless,
white crystalline powder freely soluble in
alcohol and acetone, but only slightly soluble
in water. It is classified as GRAS for use as
a buffering and neutralizing agent and, in
addition, is accepted as a flavoring adjunct
in foods to which it imparts a smooth tart-
ness without any overriding "tangy" notes.
Citric Acid
Citric acid is a tribasic compound and is one
of the most widely distributed of the natural
acids. It is the principal acidic component in
many fruits and vegetables (Table 12-8)
in which it plays an important role in the
metabolic cycle. It has been used as an
acidulant in food processing for decades and
is classified as GRAS as a general purpose
food additive. It is the acidulant of choice in
most beverage and sugar confectionery
formulations. Citric acid is still produced
from natural sources and commercially is
derived from pineapple waste.
The food grade is available in the an-
hydrous form or with one molecule of water
of hydration. It is a colorless, crystalline
material usually sold as a white granular to
finely crystalline powder. Citric acid is very
soluble in water and alcohol, but much less
so in organic solvents.
Fumaric Acid
Fumaric acid is found in rice, sugar cane,
wine, plant leaves, mushrooms and gelatin.
It is low in hygroscopicity and has consid-
erable sensory strength. It takes two parts of
fumaric acid to yield an equivalent tartness
as three parts of citric, malic or tartaric
acids.
Fumaric acid is manufactured by fermen-
tation of glucose or molasses by Rhizopus
sp. Food grade fumaric acid is available as
an odorless, white granular or crystalline
powder. It is soluble in alcohol, but only
sparingly so in cold water, being the least
soluble of the organic food acids (Table
12-7). Fumaric acid is widely used in dry
powdered food products, where solubility is
not a significant quality factor but where its
preservative and antioxidant properties are
of more value.
Lactic Acid
Lactic acid is a viscous, colorless to pale
yellow, nonvolatile liquid, which has a slight
distinctive but not unpleasant odor. It is
widely distributed in nature. The com-
mercial food grade is a mixture of lactic acid
and lactic acid lactate. This is due to the
readiness with which it undergoes self-
esterification, even in aqueous solution. On
heating, lactic acid undergoes a dehydration
involving an a-hydroxy group of one mole-
cule and the carboxyl group of another to
give lactic acid lactate, other polymers and
2-(lactoyl)propionic acid, the relative pro-
portions of these compounds being deter-
mined by the temperature. Some internal
condensation is also likely and this results in
a cyclic dilactone.
OCH · (CH3 ) · COOCH · (CH 3 ) • CO
Lactic acid is available commercially
being prepared by controlled fermentation

of sucrose, potato starch, molasses and
other sugar sources. The initial product
is usually purified by conversion into the
calcium salt and is reconstituted by acidi-
fication with sulfuric acid. The product is
normally available in aqueous solution
ranging from 50 to 90 percent lactic acid
content.
Malic Acid
Malic acid is an odorless, white crystalline
powder, the commercial product being
a racemic mixture as compared with the
natural product, which is L-rotatory. The
food grade is classified as GRAS. Malic acid
is very soluble in water and alcohol.
Compared with citric acid, which it
closely resembles in its physical properties,
malic acid has a pleasing tart taste whose
perception is smoothly continuous rather
than impressively sharp like citric acid.
It has unusual taste-blending properties,
which cause it to impart a "naturalness" to
fruit products. Malic acid is used in hard
candies, nonalcoholic beverages, canned
tomatoes and fruit pie fillings.
Malic acid has a greater acidic impact
than citric acid and is more economical to
use. In many products, 15 to 20 percent less
can be used to duplicate the acidity of citric
acid; moreover, malic is less hygroscopic
than citric.
Propionic Acid
Propionic acid is an oily liquid having a
slight pungent, rancid odor which on dilu-
tion tends to resemble that of butyric acid. It
is used more in baking practice to suppress
mold growth than as a flavoring constituent.
Its sodium and calcium salts, which are
white powders, are similarly used in dry
cake mixes.
Propionic acid is completely miscible with
water and alcohol. It is classified as GRAS
for use as a preservative and in flavorings.
Sorbic Acid
Sorbic acid is an almost odorless, white
crystalline substance with only a slight acidic
Flavoring Materials Contributing to Taste 641
taste. It and its potassium, sodium and
calcium salts are used more for their anti-
mycotic and preservative properties than for
any effect on flavor. Sorbic acid is only
slightly soluble in water, but a little more so
in alcohol. The salts are freely soluble, the
free acid being liberated in low pH media.
Food grade sorbic acid is classified as
GRAS for use as a preservative under
regulation No. 182.60.
Succinic Acid
Succinic acid is an odorless white crystalline
substance with a sharply acidic taste and a
very slight bitterness. It is very soluble in
water, alcohol and glycerol.
The food grade is classified as GRAS as a
general purpose food additive.
Succinic Anhydride
Succinic anhydride is the only commercially
available anhydride permitted for use in
food. It is used primarily as a leavening
agent in baking and is of particular value in
dry mixes. It is a white crystalline powder,
which is stable when dry but very slowly
hydrolyzes to succinic acid when mixed with
water.
Tartaric Acid
Tartaric acid and its salts occur in many
fruits, especially in grapes. In the fermen-
tation process of wine making, tartaric acid
is precipitated as the potassium or calcium
salt and pure tartaric acid is recovered from
the wine lees. Tartaric acid occurs in four
isomeric forms, the commercial product
being the L( +)form. It is a colorless, trans-
lucent crystalline substance usually available
as a fine to granular crystalline powder. It is
odorless, has a strong acidic taste and is very
soluble in water and alcohol.
Inorganic Acids
Phosphoric Acid
Phosphoric acid is used universally in the
formulation of cola drinks, with its use
dating back to the earliest soft drinks in
642 Source Book of Flavors
which fruit flavors were incorporated as
"phosphates." Its taste is somewhat flat and
quite different from the sharp tartness of
most organic food acids. As a consequence,
it blends better with nonfruit flavors.
Phosphoric acid is used in cheese making
and in the brewing industry for pH control.
Although it is a colorless crystalline solid,
phosphoric acid is normally used as a clear,
colorless, syrupy nonvolatile liquid in
concentrations ranging from 75 to 85
percent. Phosphoric acid is miscible with
water in all proportions. Caution: Phos-
phoric acid is a skin irritant and care is
necessary in its handling. Containers should
carry an appropriate warning label. In view
of its corrosive nature, formulations con-
taining this acid should be made only in a
stainless-steel plant.
POTENTIATORS AND ENHANCERS
Flavor potentiators are chemicals that
themselves have little or no odor or taste.
When used in food products, even in rela-
tively small amounts, they are capable of
either directly enhancing the existing flavor
or of modifying and often intensifying some
attribute of the flavor profile. The effect
may also be accompanied by changes in the
mouth feel of the product, thereby inducing
a sensation of fullness or satisfaction. The
following section of this chapter will present
an overview of this subject. The reader is
directed to a somewhat dated but very
comprehensive review by Maga (1986) for
more detail.
Monosodium Glutamate (MSG)
L-GLUTAMATE, Na+
(MSG)
Monosodium glutamate (MSG) is the
monosodium salt of L-glutamic acid, which
occurs naturally as one of the amino-acid
building blocks of food proteins (Skurray
and Pucar 1988). It is extensively used as a
natural seasoning, which enriches and
augments the flavor of a wide spectrum of
food products. Indigenous or added MSG
will be lost to some extent in food pro-
cessing. MSG, as an amino acid, will par-
ticipate in the Maillard reaction and be
consumed in part during thermal process-
ing. Prolonged heating will also result in
dehydration of the MSG to its lactam. An
additional loss mechanism is via leaching
into any discarded water, since it is water
soluble.
There is little agreement in the literature
as to how MSG functions physiologically in
enhancing flavor or what components of
flavor (e.g., sweetness, bitterness, meati-
ness, etc.) are enhanced. Despite this lack
of consensus, there is agreement that MSG
makes a significant positive contribution to
the acceptability and liking of food pro-
ducts, particularly savory food products.
MSG makes a positive, essentially unique
contribution to the flavor of savory foods.
The functioning of MSG is pH dependent,
i.e., it must exist in the food as the mono-
sodium salt. Therefore, its use is limited to
those foods that are in the pH range of
5.0-8.0. This essentially rules out all sweet
flavors, such as fruit or berry flavors (IFf
1987).
The primary issue involving the use of
MSG is that some people are adversely
affected by its consumption. They exhibit
what has been come to be called the
"Chinese Restaurant Syndrome." Symp-
toms include a racing pulse, flushing of the
skin, sweating, and general hypertension
and discomfort. While the scientific litera-
ture (Maga 1986 and IFf 1987) has un-
equivocally demonstrated that there are
very few individuals who demonstrate true
sensitivity to MSG (probably fewer than
have allergies to milk or shellfish), there is a
general public impression that MSG sensi-

tivity is widespread and that its use in foods
is undesirable. This has led to substantial
pressure within the food industry to for-
mulate foods without MSG, or at least to
formulate foods that are not labeled as
containing MSG. MSG addition as MSG
must be labeled in the ingredient statement.
Previous U.S. labeling laws have permitted
MSG to be added to foods as a component
of another ingredient and not be labeled as
containing MSG. This latter case has caused
a great deal of trouble in the food industry
today. Some manufacturers have chosen to
add MSG as a component of another in-
gredient (e.g., hydrolyzed vegetable protein
or autolyzed yeast) and thus add MSG
without specifically labeling it. This decep-
tion has created a lack of trust between
the food industry and the consumer, and
resulted in a series of new labeling laws to
prohibit the hidden addition of MSG to a
product.
MSG is a fine to coarse crystalline sub-
stance having the following characteristics:
pH (5% solution): 6.7-7.2
Loss on drying: max 0.5% by weight
Solubility at 25°C: 74.2 g per 100 ml water
at 60°C: 101.4 g per 100 ml water
Sodium content: 12.3%
Bulk density (by Scott Volumeter): 11.0 to
13.8 g per cu in.
Calories: 2.88 per g
The use levels for MSG suggested in
Table 12-9 are only a guide to determine
what are considered acceptable amounts in
certain types of foods. The food processor
may use them as the basis to determine the
optimum flavor performance and economics
of the product. As is noted in the follow-
ing section, MSG has a synergistic effect
when used with the 5'nucleotides (Wada,
Kawamura and Toda 1985).
Nucleotides
Since the introduction of monosodium
glutamate as a food flavor enhancer in 1909,
there has been an increasing interest in
Flavoring Materials Contributing to Taste 643
TABLE 12-9. Amount of MSG to Use in Various
Foods (Heath 1981)
Amount of MSG
to Add
Product oz./lOOlb. %
Fish Fillets-fresh or frozen 2-6 0.1-0.3
Meat and sausage products 2-10 0.1-0.5
Poultry-dressed, fresh or 2-5 0.1-0.3
frozen
Soups and gravies-canned" 3-8 0.15-0.4
Stews, hash, gravy 2-8 0.1-0.4
Vegetables-canned or frozen 3-6 0.15-0.3
Potato chips and snack items lib. MSG per lOlbs.
salt
• Ounces monosodium glutamate per 12 gal. of soup.
flavor potentiation. Research, based initially
on certain ancient customs practiced by
Japanese chefs, eventually led to the dis-
covery that some nucleotides, which are
widely distributed in both plant and animal
cells, had this effect. The ensuing research,
carrried out mainly in Japan, resulted in the
development of a range of ribonucleotides,
two of which, disodium inosinate (IMP) and
disodium guanylate (GMP), are now pro-
duced commercially in large quantity.
The source material for these compounds
is ribonucleic acid (RNA), derived mainly
from yeast. The degradation of RNA by
highly selective microbiological enzymes
gives rise to four nucleotides, namely:
adenylic, guanylic, uridylic and cytidylic
acids. Adenylic acid undergoes further re-
arrangement to become inosinic acid. Of
these materials, only inosinic and guanylic
acids are effective flavor potentiators. They
have the following chemical structure:
644 Source Book of Flavors

where R = H-disodium 5' -inosinate TABLE 12.10 Recommended use levels of 50:50 mix-
R = NH2 -disodium 5'-guanylate ture of disodium inosinate and dis-
odium guanylate and of MSG
This structure is of importance in deter- Recommended Use Level
per lOKg
mining the flavor potentiating character of Nucleotide
the product: Processed Food Mixture (g) MSG (g)
Soups and gravies
Dry soup mix
a. When the R-group is substituted by Consomme type, Ramen 15-20 500-800
either a single H or by NH2 , the Cream soup type 10-15 300-500
Dry gravies mix 10-15 500-800
compounds are flavor enhancers, but Canned soup 0.5-1 10-15
no other radical produces these Canned gravies
characteristics. Sauces
Soy sauce 1-3 100-120
b. The phosphoric acid group must be Barbecue sauce
Tomato sauce 2-3 120-140
located at the 5' position on the lower ~&f!"hetti sauce
ring. The two other possible isomers, 1tesauce 10-15 500-800
Dry sauce mix
2' and 3', have no potentiating effect. Canned foods
Loss of the phosphorus group, for Asparagus 1-5 10-20
Mushroom
example by the action of phosphatase Crab
enzymes, destroys the potentiating Shrimp 0.5-1 10-15
property of the compound. Oyster
Fish meat
Poultry
Sausage 2-3 20-30
Disodium 5'-inosinate, disodium 5'- Ham
guanylate and a 50: 50 blend of these two Dressings
Mayonnaise 1-15 30-40
chemicals are available commercially. They French dressing 200-300
10-15
consist of white to nearly white odorless Dressing mix
KetchubJ 1-2 15-20
crystals or crystalline powder having a slight Vegeta lejuice 10-15
0.5-1
but characteristic taste. These products have Tomato juice
Frozen hamburger 0.5-1 10-12
the following characteristics: Snack items
Potato chips with
Peanuts 10kgsalt 15-20 800-1000
pH (5% solution): 7.0 to 8.5 Crackers
Loss on drying: 22 to 25% Processed cheese 0.5-1 40-50
Solubility at 20°C: 25.1 g per 100 ml water
Source: Takeda Chemical Industries, Tokyo, Japan.
at 60°C: 58.3 g per 100 ml water
at 20°C: 5 g per 100 ml 20%
ethanol 1985). It is recommended that 1 g of the
50:50 mixture of 5' -nucleotides used with
Taste threshold value: 0.0063 percent in 50 g of MSG has the same flavor intensifying
aqueous solution. result as 100 g of MSG alone, although the
The nucleotides and MSG have many precise ratio may differ, depending on the
characteristics in common, but their flavor medium and the nature of other products
enhancement effects are different. The present.
nucleotides are 50 to 100 times stronger than The recommended use levels of a 50: 50
MSG on a weight basis. MSG is primarily a nucleotide mixture and of MSG are given in
"meaty" flavor enhancer; the nucleotides Table 12-10, republished by courtesy of
have much wider spectrum of effect associ- Takeda Chemical Industries Ltd., Tokyo,
ated with a positive mouth feel. The two Japan, the principal manufacturer of these
products are complementary and there is a products. The 5' nucleotides are quite stable
strong synergistic relationship when they are to most food processing operations and
used together (Wada, Kawamura and Toda during storage (some loss during canning-
 Flavoring Materials Contributing to Taste 645

Shaoul and Sporns 1987). The primary TABLE 12.11 Suggested use rates for maltol
means of loss are from leaching (they are Parts per Million
water soluble) or enzymes. in Product as Sold
Baked goods
Maltol Chocolate cookies 250
Butter cookies 75
Chocolate cake mix 150
(3- Hydroxy-2-methyl-4-pyrone) White cake mix 75-250

AOH
0 Yellow cake mix 150-250
Beverages
Chocolate drink powder 1500
Chocolate syrup 1100-3300

llo~CH3
Apple juice 10
Grape juice 10
Orange juice 25
Instant tea 3000
MSG and the ribonucleotides are effective Low calorie carbonated soft drinks 20
Confectionery
primarily in enhancing flavors that can Chocolate bar 100
broadly be classified as savory, and have Chocolate topping 250
Peanut butter fudge 50
little effect on fruit or sweet flavors. Maltol, Vanilla frosting powder 200
which occurs in several plants and is formed Dairy products
Ice cream (irrespective of flavor) 30
in roasted malt and some other roasted Creamed cottage cheese 250
products (e.g., cocoa, coffee, bread, etc.), Desserts
Instant pudding mix
has been found to have a similar and wide- Chocolate 75
ranging effect in fruit-based products, ice Vanilla 150
Regular pudding
cream, chocolate and candies, and was in- Chocolate 250
troduced as a potentiator in 1942. Vanilla 75-150
Gelatin
Maltol is produced by fermentation of Orange 150
soya bean protein or glutinin. It is a white Strawberry 200
Soups
crystalline powder with a pleasant odor and Canned soups, concentrated
is readily soluble in water. It has the fol- Vegetable 200-300
Bouillon 100
lowing characteristics: Tomato 100
Instant soup powder
Mushroom 130-350
Loss on drying: max 0.5% by weight Miscellaneous
Solubility Pork and beans 50
Chicken pot pie 100
at 20°C: 1.05 g per 100 ml water Tomato ketchup 100
at 100°C: 10 g per 100 ml water
Source: Based on use data sheet 568 (1966) for Veltol
at 25°C: 3.3 g per 100 ml ethanol (Chas. Pfizer & Co. Inc., New York).
(95%)
3.57 g per 100 ml propylene glycol
4.55 g per 100 ml benzyl alcohol
Stability in solution: Concentrated solutions together to achieve the desired effect. Ethyl
of maltol tend to discolor when placed in maltol is not available as a natural flavoring
containers made of metal, including some and thus some restrictions apply if all
grades of stainless steel. Such solutions natural labeling claims are to be made.
should be handled in glass or plastic.
SALT
The recommended use levels of maltol are
given in Table 12-11. Maltol is available (Sodium Chloride)
both as "natural" and as artificial flavoring NaCI
compounds. Much of what has been said
about maltol can be said about ethyl maltol Salt has been used in the seasoning of
as well. It is most common to use the two food since the dawn of history and its con-
646 Source Book of Flavors
tribution to flavor, dietary effects, preser-
vative and product stability have long been
established. The addition of salt to food can
give a quite specific and novel dimension
because saltiness, above all other prime
tastes, acts in part as a digestive stimulant
as well as a flavor potentiator. One can
generally tolerate up to 2 percent of salt in
food, but if it is used much in excess of this
level, the resulting product is likely to be
both indigestible and nauseating. The use of
sugar along with salt is well-founded and,
indeed, the presence of sugar may allow for
the reduction in total salt usage, for each
enhances the other. The incorporation of
salt into foods is apparently obvious, but
there is a tendency to consider the addition
of salt purely as a separate ingredient in the
formulation, rather than as an integral part
of the flavor complex. With few exceptions,
the proper function of salt is not to make the
food taste "salty" but rather to blend with
and enhance the other flavors present. The
optimum level of use is just below threshold
concentration, for salt should not be de-
tectable as such. However, if one adds just a
little bit more, as is so often the case with
this condiment, then the saltiness is at once
obvious.
Considerable research has been carried
out investigating the interrelationships of
the prime tastes. This work indicates that
salt reduces the sourness of acids and in-
creases the sweetness of sugar. It has been
demonstrated that lactic, malic and tartaric
acids increase the saltiness of salt and that
sugar can both enhance and reduce saltiness
depending upon the medium but, generally,
reduction predominates. Use is made of this
in the curing of hams. Here a sweetening
agent is used and, as the old curing method
has been replaced by one that takes only
days instead of weeks, it is necessary to
increase the concentration of salt used in the
curing liquors. This would adversely affect
the flavor, and the use of sugar reduces this
additional saltiness to acceptable levels. In
the soft drink industry, the addition of small
quantities of salt at or below threshold (e.g.,
0.15 percent) increases the apparent sweet-
ness of the beverage by about 5 percent,
thereby enabling a cost saving to be made
on the use of sugar.
Issues
Sodium, like MSG, has become an issue
with the general public. There is a wide-
spread belief that sodium is not good for
health and should be restricted. This belief
is not based on any scientific fact, for only a
small percentage of the public is adversely
affected by sodium in the diet. The vast
majority of the population can consume as
much salt as they wish with no ill effects.
The general desire to restrict sodium in the
diet, whether real or only perceived by
marketing, has created a substantial prob-
lem for the food technologist and flavor
industry. There is little question that salt is
an excellent flavor enhancer. Foods without
salt are fiat and lack character. In addition,
salt can directly influence various chemical
reactions that lead to flavor formation; this
may involve the control of fermentations or
the Maillard reaction. Thus, reducing salt in
a foot product brings the challenges of
replacing the flavor-enhancing effects of the
salt (without using MSG because it con-
tributes sodium and it is also "bad" for you,
or the 5'nucleotides because they have a
slightly different sensory effect and are too
costly to use), as well as the absolute change
in flavor profile that may be influenced by
the absence of salt.
Various approaches have been taken in
order to meet the challenges of reducing the
sodium level in foods and yet providing a
good flavor. Some of these are discussed
below.
Use of Other Flavorings
Many spices, herbs and other flavor aids can
be used to improve the palatability of low-
sodium foods and not contribute sodium
themselves (Table 12-12). Experimentation
is essential to learn the correct amounts of
flavoring to be used. The following flavoring
aids and food accompaniments for cooked
 Flavoring Materials Contributing to Taste 647

TABLE 12.12 Sodium content of food flavorings meats and vegetables do not contribute
Sodium Content
significant amounts of sodium to the diet
mg/100g and may be used as desired:
Flavoring Average
Allspice 62.0
Allspice, ground 120.0 Beef: Dry mustard, marjoram, nutmeg,
Almond 3.0-5.!1 onion, sage, thyme, pepper, bay leaf,
Anise 13.0
Basil 16.0 grape jelly.
Bay leaf 27.0 Pork: Onion, garlic, sage; with applesauce,
Caraway 17.0-27.0
Cardamom, ground 11.0 spiced apples.
Cardamom, seed 22.0 Lamb: Mint, garlic, rosemary, curry; with
Cinnamon S.O
Cinnamon, ground 21.0 broiled pineapple rings.
Cloves 210.0 Veal: Bay leaf, ginger, marjoram, curry,
Cloves, ground 24.0
Cocoa (not Dutch process) 5.0 currant jelly, spiced apricots.
Coriander 40.0 Chicken: Paprika, mushroom, thyme, sage,
Curry 45.0-64.0
Dill 13.0-IS.O parsley, cranberry sauce.
Fennel 52.0 Fish: Dry mustard, paprika, curry, bay leaf,
Garlic, less skin 6.0
Garlic, powder 22.0 lemon juice, mushrooms.
Ginger 29.0 Eggs: Pepper, green pepper, mushroom,
Ginger, ground 34.0-42.0
Horseradish, prepared 96.0 dry mustard, paprika, curry, jelly or
Horseradish, root 8.0 pineapple omelet.
Lemon juice 0.7-2.0
Mace 45.0 Asparagus: Lemon juice.
Mace, ground !12.0 Beans, green: Marjoram, lemon juice,
Mace, whole 150.0
Marjoram 32.0 nutmeg, unsalted French dressing, dill
Mint 43.0 seed.
Mustard, ground 10.0
Mustard. prepared 4.3 Broccoli: Lemon juice.
Mustard, prepared, paste 1300.0 Cabbage: Mustard dressing, dill seed, un-
Mustard, seed 9.0
Nutmeg, ground 24.0 salted butter with lemon and sugar.
Nutmeg 14.0 Carrots: Parsley, unsalted butter, mint,
Onion 7.0-10.0
Onion, powder 93.0 nutmeg, glazed with butter and sugar.
Orange juice 0.3-2.0 Cauliflower: Nutmeg.
Oregano 31.0
Paprika 82.0 Corn: Green pepper, tomatoes.
Paprika, ground 71.0 Peas: Mint, mushroom, parsley, onion.
Parsley 28.0-33.0
Parsley, flakes 490.0 Potatoes: Parsley, unsalted butter, mace,
Pepper, black 7.0-16.0 chopped green pepper, onion; baked,
Pepper, red 46.0
Pepper, white 5.0 French fried.
Peppermint extract 0.3 Squash: Ginger, mace.
Poppyseed 11.0
Poultry Seasoning 26.0 Sweet Potatoes: Candied or glazed with
Rosemary 4!1.0 cinnamon or nutmeg; escalloped with
Saffron, Spanish 24.0
Sage 20.0 apples, sugar.
Sage, rubbed 14.0 Tomatoes: Basil.
Savory 17.0
Sesame 60.0
Sugar, brown 24.0 A small amount of sugar added to vege-
Sugar, white 0.3-0.5
3!1.0 tables during the cooking period helps to
Thyme
Thyme, powdered 43.0 bring out the natural flavor of the food.
Turmeric 22.0
66.0
The water supply in some areas contains
Turmeric, ground
Vanilla extract 1.0 appreciable amounts of sodium. Water
Wine 4.0-10.0
softened by certain ion-exchange systems is
also high in sodium content. Under such
conditions it is necessary to use a natural
648 Source Book of Flavors
water low in sodium or distilled water for
formulation of all flavorings, if water is used
as a solvent.
Potassium bicarbonate may be sub-
stituted in equal amounts for sodium bi-
carbonate in recipes that designate baking
soda. Sodium-free baking powder can be
used in the proportion of 1 112 teaspoons for
each teaspoon of regular baking powder.
The following formula can be prepared with
these constituents:
Potassium bicarbonate 38.9
Cornstarch 28.0
Tartaric acid 7.5
Potassium bitartrate 56.1
Salt Substitutes
"Salt substitutes" consist of salts of ions
other than sodium to simulate sodium
chloride in taste. Potassium chloride and
ammonium chloride are the salts most
commonly used for this purpose, but the
substitutes may contain other materials in
addition.
Examination of the labeling and formulas
of commercial salt substitutes discloses:
ammonium chloride from 4 to 50 percent;
potassium chloride from 9 to 95 percent;
ammonium and potassium chlorides; citric
acid or citrates; formates; starch from less
than 1 percent to about 25 percent; various
phosphates; glutamic acid or glutamates;
and various salts of choline. Various other
materials, including vegetable powders,
may be used. The simplest formulations
may comprise only two components; some
may include as many as eight. The number
of ingredients used in 21 commercial for-
mulations totalled 26; none of them would
be expected to permit intake of more than
trace amounts of sodium (Heath 1981).
In addition to mineral-based salt sub-
stitutes, a number of so-called vegetized
salts are also marketed. Most of these have
powdered dehydrated vegetables or vege-
table powders as a base. Other ingredients
may include yeast, bran, monosodium
glutamate, lactates, malates, citrates, sac-
charated iron, magnesium carbonate,
magnesium bromide and a limited amount
of sodium chloride (even sea salt). These
are of doubtful value as salt substitutes in
diets rigidly restricted in sodium.
Ammonium chloride and potassium
chloride, each of these, and particularly
their joint use, leaves much to be desired as
to taste. Neither of them tastes like sodium
chloride. Potassium chloride usually leaves
a somewhat bitter aftertaste. Ammonium
chloride has a bitter taste and disturbs the
acid-base balance in the blood, producing
acidosis. Ammonium chloride decomposes
with liberation of ammonia during cooking
and baking temperatures, with accompany-
ing change in taste and with the released
hydrogen chloride changing the acidity and
other properties of the foods.
These disadvantages are supposedly
avoided by compounds of salt substitutes
ranging by weight in the following formu-
lation (Heath 1981):
Parts
Potassium chloride 45-90
Potassium gluconate 4.5-23.5g
Calcium gluconate or
gluconic acid 4.5-21.5
Potassium citrate 5-16
Calcium ascorbate or
ascorbic acid 4-15
Calcium cyclamate or
saccharin, or
magnesium or sodium
or potassium cyclamate 0.001-0.02%
BITTERNESS
The human palate is very sensitive to the
bitter taste which, by itself, is disagreeable
but in conjunction with other tastes may
contribute significantly to product accep-
tance. The bitter and sweet taste sensations
are frequently associated and may be pro-
duced by the same compound at differ-
ent concentrations. There is no obvious
chemical relationship between compounds
having a bitter taste, but some grouping is

possible (see review by Belitz and Wieser
1985). Three classes of organic compounds
encountered in food materials are par-
ticularly associated with bitterness-the
alkaloids, glycosides and peptides.
Alkaloids
These are nitrogenous bases that occur
widely in plants, usually in the form of their
salts with acetic or one of the carboxylic
acids. They display a broad spectrum of
structural types and almost all known
nitrogen-containing ring systems are rep-
resented. From the point of view of their
occurrence in food materials or products the
following are of particular interest:
Caffeine
Caffeine is a crystalline purine derivative,
which occurs in coffee beans (1.5 percent),
tea leaves (5 percent), mate (2 percent),
cola nuts (2.5 percent) and gurana (5 per-
cent). It is soluble 1 in 50 in cold water, but
about 1 in 2 in hot water (65°C). Caffeine is
a powerful stimulant and is classified as
GRAS. In the United States, it is permitted
for use in cola-type beverages at 0.02
percent.
Theobromine
HN~~;
O~~TJ-N
N CH2=CH·CH2·C ~
I
CHa
Flavoring Materials Contributing to Taste 649
Theobromine is often present with caffeine.
It occurs in cocoa beans (1.8 percent) and
cola nuts (0.02 percent).
Quinine
j
CH-~-CH,
CH,
I
CH,
H --lH-CHCH-CH ,
Quinine is a white amorphous powder
poorly soluble in water, but widely used in
soft drinks as its soluble sulfate or hydro-
chloride salt. In the United States, it is
permitted for use in beverages under FDA
regulation 121.1081. Quinine hydrochloride
has a taste threshold of about 0.0016 per-
cent, but much lower concentrations have
been reported.
Glycosides
This group of bitter-tasting compounds,
which occur abundantly in plants, is charac-
terized by their ready hydrolysis into two
fractions, a sugar moiety and a fraction
known as an aglycone, the reactive part of
which is a hydroxyl group (Fenwick et al.
1990). Chemically, the glycosides are classi-
fied either by their associated sugar (where
this is glucose, the compounds are known as
glucosides) or by the nature of the aglycone.
Where the aglycone is a second monosac-
charide unit, the product is a disaccharide
(e.g., sucrose).
The following bitter glycosides are of
particular interest to the ftavorist.
Sinigrin
Present in black mustard seed; yields D-
glucose and allyl isothiocyanate.
/N·O·S0 3·K
S·CsHuOs
650 Source Book of Flavors

Coniferin studied by many (Ney and Retzlaff 1989,

Present in conifer wood; yields coniferyl
alcohol on hydrolysis, and this can be
further oxidized to produce vanillin.
Adler-Nissen 1988, and Vegarud and
Langsrud 1989) and a hypothesis (Ney's
rule) developed, based on the level of
hydrophobicity of the peptide molecule.
Current work in this field has been reviewed
by Belitz and Wieser (1985) and Rouseff
(1990).

Other Bitter-Tasting Chemicals

Naringin
This flavonoid is present in grapefruit and
bitter orange; yields a D-glucose-rhamnose
disaccharide (neohesperidose) and the
aglycone naringenin.
( 1-+ 2) rhamnoglucose
OH
A few other compounds having a markedly
bitter taste are of interest to the ftavorist.
Quassin
Present in the wood and bark of Jamaica
quassia (Aeschrion excelsa). Quassin is
a white crystalline compound having an
intensely bitter taste. It is used as a de-
naturant of ethyl alcohol in many countries.
Its bitterness is of a different quality than
that of quinine.

CH~

Hesperidin
Present in sweet orange and several other
citrus fruits; yields the disaccharide, 7-~­
rutinose, and the aglycone, hespetetin, on Limonin
hydrolysis. The bitter principles present in the fruit
and seeds of many citrus species are triter-
(1-+ 7) rhamnoglucose penoids, collectively called limonoids. Their
complex chemistry is discussed by Goodwin
and Goad (1966). The most widely dis-
OH tributed of these compounds is limonin,
whose chemical structure was evolved by
Arigoni et al. (1960) and Arnott et al.
(1960). Substantial research has been de-
voted to the removal of limonin from citrus
Peptides products (Kimball 1990, Mathews et al.
Proteins on enzymatic hydrolysis often yield 1990).
bitter hydrolysates and it has long been
known that the bitter taste of high protein
foods resides in the peptide fraction and is
little affected by the nature of the amino
acids present. This reaction is of importance
in the processing of soy protein and in the
hydrolysis of casein. The subject of bitter-
ness in protein hydrolysates has been

These examples, although far from
exhaustive, illustrate the considerable di-
versity of structure associated with bitter-
ness. It is almost impossible to correlate
chemical structure with intensity or quality
of the taste sensation, and apart from the
broadest generalities no meaningful classi-
fication of bitter substances has been made.
TRIGEMINAL EFFECTS
The definition of flavor must also include
the trigeminal effects, such as the heat of
spices and the cooling of menthol. These
effects are often very significant to the
overall flavor of a food product and in-
fluence its acceptance. These sensory re-
sponses are due to the direct interaction
of bare nerve endings in the olfactory
membrane and on the tongue with certain
chemicals. The nerve endings in the tongue
are somewhat recessed and thus this re-
sponse is delayed in onset and decay. This is
why a person must take several bites of a
spicy food before the "heat" of the food is
noticeable. Likewise, the sensation does not
readily go away, but persists in spite of
attempts to cool the mouth.
Pungency
Several spices, notably capsicum, black
pepper and ginger, are remarkable more for
their pungency than for their aromatic
effects. The chemicals responsible bear
some structural relationship, but the mech-
anism of this stimulus is not fully understood.
Pepper
The principal pungent component of black
and white pepper is an alkaloid, piperine (1-
piperoylpiperidine), which is a colorless,
crystalline substance.
Theoretically, piperine exists in four
isomeric forms: piperine, isochavicine, iso-
piperine and chavicine, of which chavicine,
the cis-cis form, is said to be more pungent
and much less stable than piperine, the
trans-trans form (Arctander, 1969). A
Flavoring Materials Contributing to Taste 651
closely related and less pungent analogue,
piperettine, accompanies piperine in black
pepper.
Capsicum
Capsicums exhibit a wide range of pun-
gency, depending on the percentage of
capsaicin and other pungent amides pres-
ent. These range from 0.01 to 1 percent,
depending on the species. Capsaicin is
an alkaloid, N-vanillyl-8-methyl-6-nonena-
mide, which in most species of red pep-
pers is associated with other capsaicinoids
including: dihydrocapsaicin, nor-dihydro-
capsaicin, homocapsaicin and homodihy-
drocapsaicin (Bennett and Kirby 1968). The
pungent attribute is due to the presence of a
phenolic hydroxyl group and an ether group
in an ortho position on the benzene nucleus
and to a side chain. The length of this side
chain as well as the presence of an acid
amide group appear to be important in
determining the degree of pungency of the
compound. The presence of the o-meth-
oxyphenol group seems to be of less im-
portance as vanillin is without pungency.
Nonoylvanillylamide is an intensely pungent
synthetic chemical, which has the structural
characteristics considered essential to
pungency (Kulka 1967).
Capsaicin has a marked pungency and
burning sensation in the throat at 10ppm,
but is perceptible in concentrations as low as
0.1 ppm. This threshold value is employed
as a method of evaluating pungency in terms
of Scoville units.
Ginger
The pungency of ginger is due to a mixture
of homologues having the general formula:
0 (CH,).-CH,
OH
652 Source Book of Flavors
These comppounds have the same basic
structure as capsaicin and are known col-
lectively as gingerol, being distinguished by
an appropriate prefix number (Connell and
Sutherland 1969).
Other related pungent components are
present, including zingerone and shogaol.
Zingerone probably arises from a retroaldol
reaction of the a-hydroxy ketone in gingerol
and shogaol is a dehydration product of
gingerol. Both reactions are observed when
oleoresin ginger is heated. The formation of
these compounds leads to a reduction in the
pungency level as gingerol is more pungent
than either shogaol or zingerone (Connell
1970).
Chemicals Responsible for a Cooling Effect
The chemical primarily associated with a
cooling effect in the mouth is menthol.
Menthol is a crystalline cyclic alcohol pres-
ent in oil of peppermint (50 to 65 percent)
and oil of Mentha arvensis (75 to 90 percent)
and in small quantities in several other
essential oils. It exists in several geometric
and optical isomers (Guenther 1948-1952).
The most important isomer is 1-menthol,
the form in which it occurs naturally.
Natural1-menthol is obtained by chilling
the oil of Mentha arvensis and centrifuging
the separated crystalline mass. The residual
oil still contains 40-50 percent of menthol.
Menthol may also be prepared synthetically
from citronellal or by the hydrogenation of
thymol, menthane or pulegone.
The synthetic menthols are chiefly
racemic ( ±) with only small quantities of the
other menthols present. They are distin-
guished by having a low melting point
(32.5-34°C) whereas pure 1-menthol melts
at 42-44°C.
Astringency
Astringency is a dry feeling in the mouth or
a puckering up of the linings of the oral
cavity (Meilgaard et al. 1987) and is an
undesirable attribute in many fruits and fruit
products, including wines. This mouth feel
effect is caused by the presence of poly-
merized phenols having a high molecular
weight (500 to 3,000), the level of astrin-
gency being determined by their concen-
tration, individual chemical structure and
degree of polymerization.
The chemicals causing astringency are
collectively known as tannins and display
considerable structural differences. They
include the leucoanthocyanins, catechins
and derivatives of some aromatic acids such
as galic acid, glucosides of galic and proto-
catechuic acid, phloroglucinol esters of
galic acid as well as a range of condensed
flavonoids. Many of these compounds are
closely associated with the color of natural
products. It has been established that fruits
containing a high percentage of phenolic
compounds are more astringent than those
with low percentages, and that the astrin-
gency diminishes during maturation and
ripening of the fruit as a result of condensa-
tion and polymerization of these compounds
(Van Buren 1970).
Water-soluble tannins are significant in
the flavor profile of tea and are also associ-
ated with its color. They are present in the
dried leaves from 5 to 20 percent, depending
on the particular grade. Tannins are also
present in cacao beans, but the percentage is
considerably reduced by oxidase enzymatic
action during fermentation, making the
fermented beans much less astringent and
darker in color.
Certain spices contain tannins, the astrin-
gency of clove buds and allspice (pimento)
berries being characterized by quercitannic
acid.
References
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Organoleptic Characterization: Frontiers of
Flavor, ed. G. Charlambous, pp. 63-77.
Amsterdam: Elsevier.
Anon. 1974a. New Sweetener for low calorie
drinks-aspartame. Food Process. 36(10):
68-69.

Anon. 1974b. New synthetic is 1,000 times
sweeter than sugar. Food Eng. 46(5):50.
Arctander, S. 1969. Perfume and Flavor Chem-
icals, Vol. I and II. Montclair: Steffen
Arctander.
Arigoni, D., Barton, D.H.R., Corey, E.J., and
Jeger, 0. 1960. Constitution of limonin.
Experientia. 16:41-49.
Ariyoshi, Y. 1974. Taste and chemical structure
(2). Kagaku To Seibutsu. 12:274.
Arnott, S., Barton, D.H.R., Corey, E.J., and
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Experientia. 16:49-52.
Beauchamp, G.K. 1990. Research in Chemo-
sensation Related to Flavor and Fragrance
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Belitz, H.D. and Wieser, H. 1985. Bitter Com-
pounds: Occurrence and structure-activity
relationships. Food Reviews International.
1(2):271-354.
Bennett, D.J. and Kirby, G.W. 1968. Constitu-
tion and biosynthesis of capsicum. J. Chern.
Soc. (C). 4:442-446.
Bernetti, R. 1990. From Corn Syrup to Fructose.
Cereal Foods World. 35(4):390-393.
Connell, D.W. and Sutherland, M.D. 1969. A
re-examination of gingerol, shogaol and
gingerol, the pungent principles of ginger
(Zingiber Officinale Roscoe), Aust. J. Chern.
22:1033-1043.
Connell, D.W. 1970. The chemistry of the
essential oil and oleoresin of ginger (Zingiber
Officinale Roscoe). Flavour Ind. 1:677-693.
Dziezak, J.D. 1990. Acidulants: Ingredients
that do more than meet the acid test. Food
Techno/. 44(1):75-83.
Erickson, S. and Fagerson, I.S. 1976. Flavors of
amino acids and peptides. Int. Flavours and
Food Additives. 7(1):13-16.
Fenwick, G.R., Curl, C.L., Griffiths, N.M.,
Heaney, R.K., and Price, K.P. 1990. Bitter
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Godshall, M.A. 1990. Use of Sucrose as a
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Goodwin, T.W. and Goad, L.J. 1966. Cartenoid
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Grenby, T.H. 1989. Progress in Sweeteners. New
York: Elsevier.
Guenther, E. 1948-1952. The Essential Oils,
Vol. I- VI. New York: D. Van Nostrand Co.
Hallagan, J.B. 1991. The use of certified food
color additives in the United States. Cereal
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Higginbotham, J. 1986. Talin revisited. Food,
Flav., Ingred., pack, and Process. 8(9):39-
41.
I.F.T. 1987. Monosodium glutamate (MSG).
Food Techno/. 41(5):143-154.
Jizba, J., Doleja, L., Herout, V., and Sorm, S.
1971. Structure of osladin, the sweet principle
of the rhizomes of Podophyllum vulgaris L.
Tetrahedron Lett. 46:1329.
Junk, W.R. and Pancoast, H.M. 1973. Hand-
book of Surgars for Processors, Chemists
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Citrus Juice Bitterness. Perf. Flavor. 15(2):41.
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Kulka, K. 1967. Aspects of functional groups and
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Rouseff, R.L. 1990. Bitterness in Food Products:
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Sardesai, V.M. and Waldshan, T.H. 1991.
Natural and synthetic intense sweeteners.
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Vegarud, G.E. and Langsrud, T. 1989. The level
of bitterness and solubility of hydrolyzates
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Chapter 13
Flavoring Ingredients
Classified As GRAS By
the Flavor Extract
Manufacturers Association

List No. 4 1 (Hall and Oser 1970) 3143 2,4-Dimethyl-2-pentenoic acid

FEMANo. 3144 p-a- Dimethylstyrene (1-Methyl-
3125 Acetaldehyde, butyl phenethyl 4-isa-propenylbenzene; p-iso-
acetal Propenyltoluene)
3126 Acetypyrazine (Methyl pyrazinyl 3145 2,4-Dimethyl-5-vinylthiazole
ketone) 3146 2,2'-(Dithiodimethylene )-
3127 Allyl methyl disulfide difuran (2-Fururyl disulfide)
3128 2-Benzofurancarboxaldehyde 3147 1-Ethyl-2-acetylpyrrole
(2-Formylbenzofuran) 3148 Ethyl trans-2, cis-4-decadienoate
3129 Biphenyl 3149 2-Ethyl-3,5 or
3130 Butylamine 6-dimethylpyrazine
3131 sec-Butyl ethyl ether 3150 3-Ethyl-2,6-dimethylpyrazine
3132 2-isa-Butyl-3-methoxypyrazine (2,6-Dimethyl-3-ethyl
3133 2-isa-Butyl-3-methylpyrazine pyrazine)
(2-Methyl-3-isa-butylpyrazine) 3151 2-Ethyl-1-hexanol
3134 2-iso-Butyl thiazole 3152 3-Ethyl-2-hydroxy-2-
3135 2-trans, 4-trans- Decadienal cyclopenten-1-one
3136 2,3-Diethylpyrazine 3153 6-Ethyl-3-hydroxy-4-methyl-
3137 2,6-Dimethoxyphenol 2(5H)-furanone
3138 3,4-Dimethoxy-1-vinylbenzene (2,4-Dihydroxy-3-methyl-
3139 p-a-Dimethylbenzyl alcohol 2-hexenoic acid, y-lactone;
3140 2,6-Dimethyl-4-heptanol 2-Ethyl-3-methyl-
3141 2,6-Dimethyl-10-methylene- 4-hydroxydihydro-(2,5)-
2,6,11-dodecatrienal furan-5-one; 2-Hydroxy-
(a-Sinensal) 3-methyl-y-2-hexenolactone)
3142 3, 7-Dimethyl-6-octenoic acid 3154 2-Ethyl-5-methylpyrazine

1 FEMA GRAS lists No.1, 2 and 3 were used by the FDA as the basis for the lists published in 21 CFR sub-part D,
sections 121.1163 and 121.1164 (since renumbered 172.510 and 172.515, respectively). The FEMA lists provide
data on maximum use levels in ppm. Additional use data are given in Grundschober et al. (1975).
* FEMA No. 2758 (GRAS 3) musk ambrette has been dropped from the list.

655
 656 Source Book of Flavors

List No.4 (Hall and Oser 1970) 3190 5-Methyl-2,3-hexanedione

FEMANo. 3191 2-Methylhexanoic acid
3155 3-Ethyl-2-methylpyrazine 3192 2-Methyl-5-methoxythiazole
3156 p-Ethylphenol 3193 1-Methylnaphthalene
3157 Ethyl (p-tolyloxy)acetate (Ethyl 3194 2-Methyl-2-pentenal
p-cresoxyacetate) 3195 2-Methyl-2-pentenoic acid
3158 2-Furanmethanethiol formate 3196 3-Methyl-2-(2-pentenyl)-2-
3159 Furfuryl methyl ether cyclopenten-1-one (Jasmone)
3160 Furfuryl methyl sulfide 3197 a-Methylphenethyl butyrate (1-
3161 Furfuryl iso-propyl sulfide Phenyl-2-propyl butyrate)
3162 Furfuryl thioacetate 3198 Methyl phenethyl ether
3163 2-Fury} methyl ketone (2- 3199 5-Methyl-2-phenyl-2-hexenal
Acetylfuran) 3200 4-Methyl-2-phenyl-2-pentenal
3164 2,4-Heptadienal 3201 Methyl propyl disulfide
3165 2-Heptanal 3202 Methyl2-pyrrole ketone (2-
3166 4,4a,5,6, 7,8-Hexahydro-6-iso- Acetylpyrrole)
propenyl-4,4a-dimethyl-2(3H)- 3203 5-Methylquinoxaline
naphthalenone (Nootkatone) 3204 4-Methyl-5-thiazoleethanol (4-
3167 6- Hexalactone Methyl-5-(fl-hydroxyethyl)-
3168 3,4-Hexanedione thiazole)
3169 trans-2- Hexenoic acid 3205 4-Methyl-5-thiazoleethanol
3170 3-Hexenoic acid acetate
3171 cis-3-flexen-1-yl acetate 3206 2-Methylthioacetaldehyde
3172 Hexyl iso-butyrate 3207 1-(Methylthio)-2-butanone
3173 1-Hydroxy-2-butanone 3208 (Methylthio)methylpyrazine
3174 4-Hydroxy-2,5-dimethyl-3(2H)- (mixture of isomers (2-Methyl-3,
furanone 5- or 6-methylthiopyrazine)
3175 'Y" Ionone (4-(2,2-Dimethyl-6- 3209 5-Methyl-2-thiophenecarbox-
methylene-cyclohexyl)-3-buten- aldehyde
2-one) 3210 o-(Methythio)-phenol (2-
3176 p-Menthan-2-one Thioguaiacol)
3177 p-Mentha-8-thiol-3•one (8- 3212 2,4-Nonadienal
Mercapto-p-methane-3-one) 3213 2-Nonenal
3178 p-Menth-1-ene-9-al 3214 6-0ctalactone
3179 p- Menth-1-en-3-ol (Piperitol) 3215 2-0ctenal
3180 2~Mercaptopropionic acid 3216 Paraffin wax (Petroleum wax,
(Thiolactic acid) paraffin)
3181 o- Methoxycinnamaldehyde 3217 2,4-Pentadienal
3182 p- Methoxy-a-methyl 3218 2-Pentenal
cinnamaldehyde 3219 iso- Pentylamine (iso- Amylamine;
3183 2,5- or 6-Methoxy-3-methyl- 3-Methylbutylamine)
pyrazine (mixture of isomers) 3220 Phenethylamine
3184 1-Methyl-2-acetylpyrrole 3221 Phenethylhexanoate
3185 Methylated silica 3222 Phenethyl octanoate
3186 4-Methyl biphenyl (p- 3223 Phenol
Methyldiphenyl) 3224 2-Phenyl-2-butenal
3187 3-Methylcrotonic acid (3,3- 3225 Phenyl disulfide (Diphenyl
Dimethylacrylic acid; fl, fl- disulfide)
Dimethylacrylic acid; Senecioic 3226 1-Phenyl-1,2-propanedione
acid) 3227 Propenyl propyl disulfide
3188 2-Methyl-3-furanthiol 3228 Propyl disulfide
3189 2-Methyl-3,5- or 6-furfuryl 3229 iso-Propyl tiglate (iso-Propyl a-
thiopyrazine (mixture of isomers methyl crotonic acid)
 Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association 657

List No.4 <Hall and Oser 1970) 3270 spiro 2,4-Dithia-1-methyl-8-

FEMANo. oxabicyclo[3,3,0] octane-3,3' -(1'-
3230 Pyrazine ethanethiol (Pyrazinyl oxa-2' -methyl)cyclopentane and
ethanethiol) spiro 2,4-Dithia-6-methyl-7-
3231 Pyrazinyl methyl sulfide (Pyrazinyl oxabicyclo[3,3,0] octane-3,3' -(1'-
methyl methyl sulfide) oxa-2-methyl)cyclopentane
3232 2-Pyridinemethanethiol (2- 3271 2,3-Dimethylpyrazine (2,3-
Pyridylmethanethiol) Dimethyl-1,4-diazine)
3233 Styrene 3272 2,5-Dimethylpyrazine (2,5-
3235 4,5,6, 7-Tetrahydro-3,6-dimethyl- Dimethyl-1,4-diazine)
benzofuran(~enthofuran) 3273 2,6-Dimethylpyrazine (2,6-
3236 Tetrahydro-4-methyl-2-(2-methyl- Dimethyl-1,4-diazine)
propen -1-yl)pyran (Rose oxide) 3274 4,5-Dimethylthiazole
3237 2,3,5,6-Tetramethylpyrazine 3275 Dimethyl trisulfide
3238 2,2'(Thiodimethylene)-difuran (2- 3276 Dipropyl trisulfide
Furfuryl monosulfide) 3277 Disodium succinate
3239 4-Thujanol (Sabinenehydrate) 3278 Ethyl2,4-dioxohexanoate (Ethyl2,
3240 o-Toluenethiol (2- 4-diketocaproate)
~ethylthiophenol) 3279 Ethyl2-mercaptopropionate
3241 Trimethylamine 3280 2-Ethyl-(3,5 and 6)-
3242 p, a,a,Trimethylbenzyl alcohol methoxypyrazine (85%) plus 2-
(p-Cymen-8-ol; Dimethylp-tolyl ~ethyl-(3,5 and 6)-
carbinol) methoxypyrazine (13%)
3243 4-[ (2,6,6)-Trimethyl cyclohex-1- 3281 2-Ethylpyrazine (2-Ethyl-1,4-
enyl] but-2-en-4-one diazine)
3244 2,3,5,-Trimethylpyrazine 3282 Ethyl thioacetate
3245 Undecanoic acid 3283 Furfuryl2-methylbutanoate
3246 2-Undecanol (Furfuryl isovalerate)
3247 10-Undecenoic acid 3284 N-Furfurylpyrrole (1-(2-Furfuryl)
3249 2,6-Xylenol (2,6-Dimethylphenol) pyrrole)
3285 L-Glutamic acid
List No.5 (Oser and Hall1972) 3286 Glyceryl tripropanoate
FEMANo. 3287 Glycine
3250 2-Acetyl-3-ethyl pyrazine 3288 2-Heptanol
3251 2-Acetylpyridine 3289 4-Heptenal (cis and trans)
3252 {j-Alinine 3290 3-Hexanone
3253 Allyl methyl trisulfide 3291 4-Hydroxy butanoic acid lactone (.y-
3254 Ara binogalactan Butyrolactone)
3255 L-Arabinose 3292 3-(Hydroxymethyl)-2-octanone
3256 Benzothiazole 3293 4-Hydroxy-3-pentenoic acid
3257 Bis(2-furfuryl) disulfide lactone (a-Angelica lactone)
3258 Bis(2-furfuryl) sulfide 3294 5-Hydroxyundecanoic acid lactone
3259 Bis(2-methyl-3-furyl) disulfide (t.- Undecalactone)
3260 Bis(2-methyl-3-furyl) tetrasulfide 3295 D, L-Isoleucine
3261 2-sec- Butylcyclohexanone 3296 Isopropenylpyrazine (2-
3262 Cyclopentanethiol Isopropenyl-1,4-diazine)
3263 L-Cysteine 3297 L-Leucine
3264 4-Decenal 3298 3-~ercapto-2-butanone
3265 Diallyl trisulfide 3299 2- ~ercaptomethylpyrazine
3266 4,5-Dihvdro-3(2H)thiophenone 3300 3- ~ercapto-2-pentanone
3267 2,4-Dirn<!thyl-5-acetylthiazole 3301 D, L- ~ethionine
3268 3,4-Dimethyl-1,2-cyclopentadione 3302 ~ethoxypyrazine (2- ~ethoxy-1 ,4-
3269 3,5-Dimethyl-1,2-cyclopentadione diazine)
 658 Source Book of Flavors

List No.5 (Oser and Hall1972) 3343 Ethyl3-methylthiopr opionate

FEMANo. 3344 Ethyl cis-4-octenoate
2-Methyl-1-butanethiol 3345 2-Ethylthiophenol (2-
3303
3304 3-Methyl-2-butanethiol Ethylphenylmercaptan)
1-Methyl-2,3-cyclohexadione 3346 Furfuryl propionate
3305
3347 Furfuryl thiopropionate
3306 5H-5-Methyl-6,7-
3348 Heptanoic acid
dihydrocyclopenta(b)pyrazine
3-(5-Methyl-2-furyl) butanal 3349 4-Heptenal diethyl acetal
3307
3350 3-Heptyl-5-methyl-2(3H)-furanone
3308 Methyl propyl trisulfide
(a-n-Heptyl-'Y·valerolactone)
3309 2-Methylpyrazine
Methyl thiobutyrate 3351 3-Hexanol
3310
3352 4-Hexene-3-one
3311 Methyl thiofuroate
3353 3-Hexenyl formate (3-Hexenyl
3312 3-Methylthiopropyl isothiocyanate
methanoate)
3313 4-Methyl-5-vinylthiazole
3354 n-Hexyl2-butenoate
3314 2-Naphthalenethiol (2-Naphthyl
3355 6-Hydroxy-3, 7-dimethyloctanoic
mercaptan)
acid lactone
3315 2-Nonanol
2-Pentanol 3356 Hydroxynonanoic acid, b. -lactone
3316
(b.- Nonalactone)
3317 2-Pentyl furan
3-Phenyl-4-pentenal 3357 2-Keto-4-butanethiol (4-Mercapto-
3318
2-butanone)
3319 L-Proline
3358 2-Methoxy-3,(5 and 6)-
3320 Tetra hydrofurfuryl cinnamate
isopropylpyrazine
3321 5,6, 7,8-Tetrahydroquinoxaline
(Cyclohexapyrazine) 3359 2-Methylbutyl2-meth ylbutyrate
3360 3-Methyl-2-cyclohexen-1-one
3322 Thiamine hydrochloride (Vitamin
3361 Methyl3,7-dimethyl-6-octenoate
B1)
2-Thienyl disulfide 3362 Methyl furfuryl disulfide
3323
3363 6-Methyl-3,5-heptadien-2-one
3324 3,5,5-Trimethyl-1-hexanol
3364 Methyl3-hexenoate
3325 2,4,5-Trimethylthiazole
3365 5-Methyl-5-hexen-2-one
3366 2-Methyl-5-(Methylthio)furan
List No.6 (Oser and Ford 1973A) 3367 Methyl cis-4-octenoate
FEMANo. 3368 4-Methyl-3-penten-2-one
3326 Acetone 3369 2-Methylpropyl3-me thylbutyrate
3327 2-Acetyl-3,5(and 6)- 3370 2-(2-Methylpropyl) pyridine
dimethylpyrazine 3371 3-(2-Methylpropyl) pyridine
3328 2-Acetyl thiazole 3372 2-(1-Methylpropyl) thiazole
3329 Allyl thiopropionate 3373 2-Methyltetrahydrof uran -3-one
3330 Benzyl trans-2-methyl-2-but enoate 3374 3-Methylthiobutanal
3331 Bisabolene 3375 4-Methylthio-2-butanone
3332 Butan-3-one-2-yl butanoate 3376 4-Methylthio-4-methyl-2-
3333 3-Butylidenephthalide pentanone
3334 3-n-Butylphthalide 3377 Nona-2-trans,6-cis-dienal
3335 Di-(butan-3-one-1-yl) sulfide 3378 2,6-Nonadienal diethyl acetal
3336 2,3-Diethyl-5-methylpyrazine 3379 trans-2- Nonen-1-ol
3337 Difurfuryl ether 3380 9,12-0ctadecadienoic acid (48%)
3338 5,7-Dihydro-2-methylthieno(3,4-D) and 9,12,15-0ctatrienoic acid
pyramidine (52%)
3339 3,7-Dimethylocta-2,6-dienyl2- 3381 3-0xobutanal dimethyl acetal
ethylbutanoate 3382 1-Penten-3-one
3340 2-Ethoxythiazole 3383 2-Pentylpyridine
3341 Ethyl2-ethyl-3-pheny lpropanoate 3384 Phenylacetaldehyde diisobutyl
3342 Ethyl2-hexenoate acetal
 · Ingredients
Flavonng · Cl assi·fi ed A s GRAS By the Flavor Extract Manufacturers Association 659

List No.6 Continued 3417 3-Penten-2-one

FEMANo. 3418 Pentyl 2-furyl ketone
3385 Propyl thioacetate 3419 Propylene glycol dibenzoate
3386 Pyrrole 3420 4-(2,6,6-Trimethylcyclohexa -1,3-
3387 p-Tolyl3-methylbuty rate dienyl)but-2-en-4-one
3388 2-Tridecanone 3421 2,6,6-Trimethylcyclohex-2-ene-1,
3389 2,6,6-Trimethylcyclohexa -1,3- 4-dione
dienyl methanal 3422 2,4-Undecadienal
3390 1,3,3-Trimethyl-2-norbomanyl 3423 2-Undecenal
acetate

List No.7 (OserandFord 1973B)

List No.8 (Oser and Ford 1974)
FEMANo.
FEMANo.
3391 3-Acetyl-2,5-dimethylfuran
3424 3-Acetylpyridine (Methyl3-pyridyl
3392 2-Butyl-2-butenal
ketone)
3393 n-Butyl2-methylbuty rate
3425 Cycloheptadeca -9-en -l-one
3394 3-Ethylpyridine
3426 1,1-Dimethoxyethane
3395 2-Formyl-6,6-dimethyl bicyclo
(Dimethylacetal)
[3,1,1] hept-2-ene (Myrtenal)
3427 2,4-Dimethylbenzaldehyde
3396 a- Furfuryl octanoate (a-Furfuryl
caprylate) 3428 Ethyl3-hydroxybuty rate
3397 Furfuryl pentanoate (a-Furfuryl 3429 trans, trans-2,4-Hexadienal
valerate) 3430 4-Hexen-1-ol
3398 Glyceryl tribenzoate 3431 cis-3-Hexenyl formate (duplicate of
3399 2-Hepten-4-one 3353)
3400 3-Hepten-2-one 3432 Isobutyl2-butenoate
3401 2-Heptylfuran 3433 2-Methoxy-3-( 1-methylpropyl)
3402 cis-3-Hexenyl butyrate pyrazine
3403 cis-3-Hexenyl hexanoate 3434 3-Methyl-1-cyclopentadecanone
3404 N -( 4-Hydroxy-3-methoxybenzyl)- 3435 1-Methyl-1-cyclopenten-3-one
8-methyl-6-nonenamide 3436 1-Methyl-3-methoxy-4-
(Capsaicin; trans-8-Methyl-N- isopropyl benzene
vanillyl-6-nonenamide) 3437 3-Methylpentanoic acid (3-
3405 2-Hydroxymethyl-6,6-dimethyl Methylvaleric acid)
bicyclo [3,1,1] hept-2-enyl 3438 3-Methylthio-1-hexanol
formate (Myrtenyl formate) 3439 Myrtenol
3406 2-lsopropyl-5-methyl-2-hexenal 3440 3-Nonanone
3407 2-Methyl-2-butenal (2- 3441 2,2,4-Trimethyl-1,3-
Methylcrotonaldehyde) oxacyclopentane
3408 Methyl dihydrojasmonate 3442 2,6,10-Trimethyl-2,6,10-
3409 5-Methyl-3-hexen-2-one pentadecatrien-14-one
3410 Methyljasmonate (Methyl(2-pent- 3443 Valencene
2-enyl-3-oxo-1-cyclopentyl) 3444 D,L-Valine
acetate)
3411 Methyllinoleate (48%); Methyl
linolenate (52%) mixture
3412 Methyl4-(methylthio ) butyrate List No.9 (Oser and Ford 1975)
3413 2-Methylpentanal (2- FEMANo.
Methylvaleraldehyde 3445 D,L-(3-Amino-3-carboxypropyl)
3414 4-(Methylthio)butanol dimethylsulfonium chloride
3415 3-(Methylthio)propanol (Vitamin U)
3416 3-0cten-2-one 3446 Dehydrodihydroionol
 660 Source Book of Flavors

List No.9 (Oser and Ford 1975) 3481 2,5-Dimethyl-3-thiofuroyl-furan

FEMANo. 3482 2,5-Dimethyl-3-3-thioisovaleryl-
3447 Dehydrodihydroionone fur an
3448 Dicyclohexyl disulfide (Cyclohexyl 3483 2,8-Dithianon-3-en-4-
disulfide) carboxy aldehyde
3449 1,4-Dimethyl-4-acetyl-1- 3484 1,2-Ethanedithiol
cyclohexene (1,4-Dimethyl- 3485 o-(Ethoxymethyl)phenol
cyclohex-3-enyl methyl ketone) 3486 Ethyl trans-2-butenoate
3450 2,5-Dimethyl- 2,5-dihydroxy-1 ,4- 3487 Ethyl maltol (2-Ethyl-3-hydroxy-
dithiane 4H-pyran-4-one)
3451 2,5-Dimethyl-3-furanthiol 3488 Ethyl 2-methylpentanoate
3452 Dodecyl isobutyrate 3489 Ethyl2-methyl-4-pentenoate
3453 3-Ethyl-2-hydroxy-4-methyl- 3490 Ethyloctadecanoate
cyclopent-2-en-1-one (3-Ethyl- 3491 2-Ethyl-1 ,3,3-trimethyl- 2-
4-methyl-cyclotene) norbornanol
3454 5-Ethyl-2-hydroxy-3-methyl- 3492 Ethylundecanoate
cyclopent-2-en-1-one (5-Ethyl- 3493 trans-3- Heptenyl acetate
3-methyl-cyclotene) 3494 trans-3-Heptenyl2-
3455 N-Ethyl- 2-isopropyl-5-methyl- methylpropanoate (trans-3-
cyclohexane carboxamide Heptenyl isobutyrate)
3456 Ethyl2-methyl-3-pentenoate 3495 1,6-Hexanedithiol
3457 Hexyl phenylacetate 3496 cis-4- Hexenal
3458 2-Hydroxy- 2-cyclohexen -l-one 3497 3-Hexenyl2-methylbutanoate
3459 2-Hydroxy-3,5,5-trimethyl-2- 3498 3-Hexenyl3-methylbutanoate (3-
cyclohexenone Hexenyl isovalerate)
3499 Hexyl2-methylbutanoate
3460 d,l-lsomenthone
3500 Hexyl 3-methylbutanoate (Hexyl
3461 2-lsopropylphenol (1-Hydroxy-2-
isopropyl benzene) isovalerate)
3501 Linalyl phenylacetate
3462 Malty! isobutyrate
3502 2-Mercapto-3-butanol(3-
3463 4-Methylpentenoic acid
3464 2-Methyl-3-pentenoic acid Mercapto-2-butanol)
cis-6- Non en -1-ol 3503 2,3 or 10-Mercaptopinane
3465
3504 Methyl benzyl disulfide
3466 2-trans,6-trans-Octadienal
cis-3-0cten-1-ol 3505 3-Methylbutyl 2-methylbutanoate
3467
3506 2-Methylbutyl 3-methylbutanoate
3468 2-Phenyl-3-carbethoxyfuran
3507 3-Methylbutyl 2-methylpropanoate
3469 Propiophenone
3508 Methyl3-hydroxyhexanoate
3470 Quinoline
1,5,5,9-Tetramethyl-13-oxatricyclo 3509 a-Methyl-{3-hydroxypropyl
3471
3510 4-Methyl-4-pentenal
[8,3,0,0] tridecane
3511 2-Methyl-4-pentenoic acid
3472 Thiogeraniol
2,2,6-trimethylcyclohexanone 3512 2-Methyltetrahydrothiophen -3-one
3473
2,6,-Trimethyl-1-cyclohexen-1- 3513 1,9-Nonanedithiol
3474
3514 1,8-0ctanedithiol
acetaldehyde
3515 1-0cten-3-one
3475 Trithioacetone
3516 trans-2-0cten-1-yl acetate
3517 trans-2-0cten-1-yl butanoate
List No.10 (Oser and Ford 1977) 3518 Octyl2-furoate
FEMANo. 3519 2-Phenyl-4-pentenal
3476 Bis-( 2,5-Dimethyl-3-furyl)disulfide 3520 1,2-Propanedithiol
3477 2,3- Butanethiol 3521 Propanethiol
3478 1-Butanethiol 3522 o-Propyl phenol
3479 Candelilla wax (from the stems and 3523 Pyrrolidine
branches of Euphorbia cerifera) 3524 3,5,5-Trimethylhexanal
3480 a-Cresol 3525 2,4,5-Trimethyl-t:. -3-oxazoline
 Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association 661

List No.ll (Oser and Ford 1978) 3560 p-Mentha-1,4(8)-dien-3-one

FEMANo. (Piperitenone)
3526 2-Acetoxy-3-butanone (Acetoin 3561 p-Mentha-1,8-dien-7-yl acetate
acetate) (Dihydrocuminyl acetate)
3527 3-Acetyl-2,5-dimethylthiophene 3562 p-Menthan-2-ol (Carvomenthol)
3528 1,2-Butanedithiol ( 1,2- 3563 p-Mentha-3-en-1-ol (Terpineol)
Dimercaptobutane) 3564 p-Mentha-8-en-1-ol ({3-Terpineol)
3529 1,3-Butanedithiol (1,3- 3565 p-Menth-8-en-2-one (cis-
Dimercaptobutane) Dihydrocarvone)
3530 m-Cresol (3-Hydroxytoluene) 3566 1-p-Menthen-9-ylacetate(9-
3531 Cyclohexanecarboxylic acid Acetoxy-1-p-menthene)
3532 3-Decen-2-one 3567 p- Methoxycinnamaldehyde
3533 Diallyl polysulfides (Diallyl di-, tri-, 3568 Methyl cyclohexanecarboxylate
tetra- and pentasulfides) 3569 2-Methyl-3,5 or 6-ethoxypyrazine
3534 1,2-Di [(1'ethoxy)-ethoxy] propane 3570 3-[ ( 2-Methyl-3-furyl)-thio]-4-
3535 2,3-Dimethylbenzofuran heptanone
3536 Dimethyl disulfide (Methyl 3571 4[(2-Methyl-3-furyl)-thio]-5-
disulfide) nonanone
3537 2,6-Dimethyl-4-heptanone 3572 5-Methylhexanoic acid
(Diisobutyl ketone) 3573 Methyl2-methyl-3-furyl disulfide
3538 2,6-Dimethyl-3-[(2-methyl-3-furyl) 3574 4-Methylnonanoic acid
thio]-4-heptanone (1,3- 3575 4-Methyloctanoic acid
Diisopropylacetonyl-2-methyl-3- 3576 Methyl1-propenyl disulfide
furyl sulfide) (Methyldithio-1-propene)
3539 3,7 -Dimethyl-1,3,6-octatriene 3577 3-Methyl-5-propyl-2-cyclohexen-1-
(trans-{3-0cimene) one (Celery ketone)
3540 2,6-Dimethylpyridine 3578 2-Methyl-4-propyl-1,3-oxathiane
3541 3,5-Dimethyl-1,2,4-Trithiolane 3579 1,4-Nonanediol diacetate
3542 6,10-Dimethyl-5,9-undecadien-2- 3580 cis-6-Nonenal
one (Geranyl acetone) 3581 3-0ctanol
3543 Ethylene brassy late (Ethylene 3582 1-0cten-3-ylacetate(3-
glycol brassylate cyclic diester) Acetoxyoctene)
3544 Ethyl cyclohexanecarboxylate 3583 3-0ctyl acetate
3545 Ethyl3-hydroxyhexanoate 3584 1-Penten-3-ol
3546 5-Ethyl-2-methylpyridine (2- 3585 L- Phenylalanine
Methyl-5-ethylpyridine) 3586 2-Phenyl-3(2-furyl)prop-2-enal
3547 3-Heptanol 3587 2(10)-Pinen-3-ol (pinocarveol)
3548 2-Hydroxyacetophenone (o- 3588 1,3-Propanedithiol
Acety lphenol) 3589 Resorcinol (1,3-Benzenediol)
3549 6-Hydroxydihydrotheaspirane 3590 A-Tetradecalactone
3550 3-Hydroxy-2-pentanone 3591 Theobromine (3,7-
3551 lsoamylacetoacetate(lsoamyl3- Dimethylxanthine)
oxobutanoate) 3592 2,2,3-Trimethylcyclopent-3-en-1-yl
3552 Isojasmone (Dihydrojasmone) acetaldehyde
3553 lsophorone 3593 1,2,3-Tris [(1'ethoxy)-ethoxy]
3554 lsopropyl-2-methylpyrazine (2- propane
Methyl-5-isopropylpyrazine) 3594 Verbenol (2-Pinen-4-ol)
3555 Isopropyl-4-methylthiazole 3595 2,5-Xylenol (2,5-Dimethylphenol)
3556 Isopropyl myristate (Isopropyl 3596 3,4-Xylenol (3,4-Dimethylphenol)
tetradecanoa te)
3557 p-Mentha-1,8-dien-7 -al List No.12 (Oser and Ford 1979)
(Perillaldehyde) FEMA No.
3558 p-Mentha-1,3-diene (a-Terpinene) 3597 Benzyl methyl sulfide
3559 p-Mentha-1,4-diene (-y-Terpinene) 3598 2-Methoxy-4-propylphenol
662 Source Book of Flavors

ListNo.l2 (Oser and Ford 1979) 3640 p-Methylcinnamaldehyde

FEMANo. 3641 Ethyl trans-2-decenoate
3599 trans-2-Methyl-2-butenoic acid 3642 Ethyl trans-4-decenoate
3600 4-(Methylthio)butanol 3643 Eteyl trans-2-octenoate
3601 2-[(Methylthio)methyi]-2-buten al 3644 2-Methylbutyl acetate
3602 3-0cten-2-ol 3645 cis-5-Isopropenyl-cis-
3603 2-0cten-4-one 2-methylcyclopentan-
3604 Octyl2-methylbutyrate 1-carboxaldehyde
3605 3-Decanol 3646 3-Methyl-2-butenal
3606 o-Xylose 3647 3-Methyl-2-buten-1-ol
3607 Propyl 2-methyl-3-furyl disulfide 3648 Propyl2,4-decadienoate
3608 1-Hexen-3-ol 3649 p- Propylphenol
3609 2-Acetyl-5-methylfuran 3650 Butyl salicylate
3610 E- Dodecalactone
3611 2-Propionylthiazole ListNo.l3 (Oser eta!. 1984)
3612 1-0cten-3-yl butyrate FEMANo.
3613 E- Decalactone 3651 6-Acetoxydihydro-theaspirane
3614 2-Propionylpyrrole 1-Acetoxy-2-methoxybenzene
3615 Thiazole (see Guaiacyl acetate,
3616 Benzenethiol no. 3687)
3617 Benzyl disulfide 1-Acetoxy-2-(2,2,3-trimethyl-
3618 5-Phenylpentanol 3-cyclopentenyl)ethane
3619 2-(2-Butyl)4,5-dimethyl- (see Campholene acetate,
3-thiazoline no. 3657)
3620 4,4-Dimethyl-2-ethyl- 3652 4-(p-Acetoxyphenyl)-2-butanone
3-thiazoline 3653 4-Acetyl-6-t-butyl-1,
3621 4,5-Dimethyl-2-isobutyl- 1-dimethylindane
3-thiazoline 1-Acetylcyclohexyl acetate
3622 ~-Damascone (see Methyl
3623 2-Ethyl-4-hydroxy-5-methyl- 1-acetoxycyclohexyl ketone,
3(2H)-furanone no. 3701)
3624 a-Ionol Acetyl guaiacol
3625 ~-Ionol (see Guaiacyl acetate,
3626 Dihydro-~-ionone no. 3687)
3627 Dihydro-~-ionol 3654 4-Acetyl-2-methylpyrimidine
3628 Dihydro-a-ionone 3655 4-Allyl-2,6-dimethoxyphenol
3629 2-Methyl-4-phenyl-2-butanol 4-Allylsyringol
3630 4-Methyl-2-pentyl-1 ,3-dioxolane (see 4-Allyl-
3631 Cyclohexylmethyl pyrazine 2,6-dimethoxyphenol.
3632 Phenethyl2-methyl-butyrate no. 3655)
3633 3-Hexenyl phenylacetate a-Amino-4-imidazolepropionic
3634 4,5-dimethyl-3-hydroxy- acid
2,5-dihydrofuran-2-one (see L-Histidine, no. 3694)
3635 4-Hydroxy-5-methyl-3(2H)- 2-Amino-3 (4-imidazyl)
furanone propionic acid
3636 2-Methyl-3-thioacetoxy- (see L-Histidine, no. 3694)
4,5-dihydrofuran a-Amino-~-
3637 2-trans-6-cis- Dodecadienal phenylpropionic acid
3638 2-trans-4-cis-7-cis-Tridecadienal (see o, L-Phenylalanine,
3639 2,6,6-Trimethyl- no. 3726)
1&2-cyclohexen- 2-Aminobutanedioc acid
1-carboxaldehyde (see L-Aspartic acid, no. 3656)
Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association 663

List No. 13 Continued (see Dihydroxyacetophenone,

FEMANo. no. 3662)
2-Aminoglutaramic acid 2,6-Dimethoxy-p-cresol
(see L-Glutamine, no. 3684) (see 4-Methyl-
a-Aminohydrocinnamic acid 2-6-dimethoxyphenol,
(see o, L-Phenylalanine, no. 3704)
no. 3726) 2,6-Dimethylbenzenethiol
2-Aminosuccinic acid (see 2,6-Dimethylthiophenol,
(see L-Aspartic acid, no. 3656) no. 3666)
3656 L-Aspartic acid 3663 2,6-Dimethyl-6-hepten-1-ol
a-Benzylidene methional 3664 2,5-Dimethyl-4-methoxy-3(2h)-
(see 2-(Methylthiomethyl)- furanone
3-phenylpropenal, no. 3717) 3665 2,2-Dimethyl-5-
Benzyl isoeugenol (1-methylpropen-1-yl)-
(see Isoeugenyl benzyl ether, tetrahydrofuran
no. 3698) 3666 2,6-Dimethyl-thiophenol
Benzyl 2-methoxy- Dioxyacetophenone
4-propenylphenyl ether (see Dihydroxyacetophenone,
(see Isoeugenyl benzyl ether, no. 3662)
no. 3698) 3667 Diphenyl ether
1-Benzyloxy-2-methoxy- Diphenyl oxide
4-propenylbenzene (see Diphenyl ether, no. 3667)
(see Isoeugenyl benzyl ether, 3668 Disodium 5-guanylate
no. 3698) 3669 Disodium 5-inosinate
Bois de rose oxide 3670 trans,trans-2,4-dodecadienal
(see 2,6,6-Trimethyl- (E,E)-2,4-Dodecadienal
2-vinyltetrahydropyran, (see trans, trans-
no. 3735) 2,4-Dodecadienal, no. 3670)
3657 Campholene acetate 1,4-Epoxy-p-menthane
3-Carbomethoxypyridine (see 1,4-Cineole, no. 3658)
(see Methyl nicotinate, 4-Ethenylphenol
no. 3709) (seep-Vinyl phenol, no. 3739)
3658 1,4-Cineole 1-Ethoxy-4-hydroxybenzene
2,4-Cresotaldehyde (See (see Hydroquinone monoethyl
2-Hydroxy- ether, no. 3695)
4-methylbenzaldehyde, p- Ethoxyphenol
no. 3697) (see Hydroquinone monoethyl
p-Cresyl octanoate ether, no. 3695)
(see p-Tolyl octanoate, 3671 4-Ethyl-2,6-dimethoxyphenol
no. 3733) 3672 2-Ethyl-4,5-dimethyloxazole
o-Cresyl salicylate 3673 2-ethylfuran
(see o-Tolyl salicylate, Ethyl ~-furfuryl-
no. 3734) a-thiopropionate
3659 a-Damascone (see Ethyl3-(furfurylthio)
3660 9-Decenoic acid propionate, no. 3674)
6-Deoxy-L-mannose 3674 Ethyl3-(furfurylthio )-
(see L-Rhamnose, no. 3730) proprionate
3661 3,6-Dihydro-4-methyl-2- Ethyl ~-ketohexanoate
(2-methylropen-1-yl)-2h-pyran (see Ethyl3-oxohexanoate ,
3662 Dihydroxyacetophenone no. 3683)
1-(x,y-Dihydroxyphenyl)- 3675 Ethyl trans-2-hexenoate
ethanone Ethyl (E)-2-hexenoate
664 Source Book of Flavors

List No. 13 Continued 3-hexenoate, no. 3689)

FEMA No. cis-3-Hexenyl
(see Ethyl trans-2-hexenoate, 2-hydroxypropanoate
no. 3675) (see cis-3-Hexenyllactate,
1-Ethylhexyl 2-methyl- no. 3690)
2-butenoate 3690 cis-3-Hexenyllactate
(see 1-Ethylhexyl tiglate, (Z)-3-Hexenyllactate
no. 3676) (see cis-3-Hexenyllactate,
1-Ethylhexyl2-methylcrotonate no. 3690)
(see 1-Ethylhexyl tiglate, 3691 Hexyl benzoate
no. 3676) 3692 Hexyl trans-2-hexenoate
3676 1-Ethylhexyl tiglate Hexyl (E)-2-hexenoate
3677 Ethyl 3-mercaptopropionate (see Hexyl trans-2-hexenoate,
3678 Ethyl2-methyl- no. 3692)
3 ,4-pentadienoate 3693 Hexyl2-methyl-3&4-pentenoate
3679 Ethyl3-methylpentanoate 3694 L-Histidine
3680 2-Ethyl-4-methylthiazole 3695 Hydroquinone monoethyl ether
3681 Ethyl4-(methyl thio )butyrate 3696 5-Hydroxy-2,4-decadienoic acid
Ethyl3-methylvalerate a-lactone
(see Ethyl 4-Hydroxy-3-methoxybenzyl
3-methylpentanoate, no. 3679) alcohol
3682 Ethyl cis-4,7-octadienoate (see Vanillyl alcohol,
Ethyl (Z)-4, 7-octadienoate No. 3737)
(see Ethyl cis- 4-( 4-Hydroxy-
4,7-octadienoate, no. 3682) 3-methoxyphenyl)but-
3683 Ethyl 3-oxohexanoate 3-en-2-one
Ethyl 3-thiopropionate (see Vanillylidene acetone,
(see Ethyl no. 3738)
3-mercaptopropionate, 4-Hydroxy-
no. 3677) 3-methoxyphenylmethanol
2-Ethyloxole (see Vanillyl alcohol, no. 3737)
(see 2-Ethylfuran, no. 3673) 3697 2-H ydroxy-4-methylbenz-
4-Ethylsyringol aldehyde
(see 4-Ethyl- ~-(p-Hydroxyphenyl)alanine
2,6-dimethoxyphenol, (see L-Tyrosine, no. 3736)
no. 3671) 4-Hydroxystyrene
iso-Eugenyl benzyl ether (seep- Vinylphenol, no. 3739)
(see Isoeugenyl benzyl ether, 2-Isobutoxynaphthalene
no. 3698) (see ~-Naphthyl isobutyl ether,
Glutamic acid-S-amide no. 3719)
(see L-Glutamine, no. 3684) Isobutyl ~-naphthyl ether
3684 L-Glutamine (see ~-Naphthyl isobutyl ether,
3685 Glyceryl 5-hydroxydecanoate no. 3719)
3686 Glyceryl 5-hydroxydode-canoate Isodulcit
3687 Guaiacyl acetate (see L-Rhamnose, no. 3730)
3688 cis-3-hexenyl benzoate 3698 Isoeugenyl benzyl ether
(Z)-3-Hexenyl benzoate 4-Isopropyl-3-cyclohexene-
(see cis-3-Hexenyl benzoate, !-carboxylic acid
no. 3688) (see 1,2,5,6-
3689 cis-3-Hexenyl cis-3-hexenoate Tetrahydrocuminic acid,
(Z)-3-Hexenyl (Z)-3-hexenoate no. 3731)
(see cis-3-Hexenyl cis- 3699 Isopropyl2-methylbutyrate
Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association 665

List No. 13 Continued Methyl isopropyl carbinol

FEMANo.
a-Ketobutyric acid
(see 2-0xobutyric acid,
no. 3723)
L-Mannomethylose
(see L-Rhamnose, no. 3730)
a-Melonol
(see 2,6-Dimethyl-6-hepten-
1-ol, no. 3663)
3700 1-p-Menthene-8-thiol
4-Methoxy-2,5-dimethyl-3(2H)-
furanone, no. 3664)
6-Methoxyeugenol
(see 4-Allyl-
2,6-dimethoxyphenol,
no. 3655)
6-Methoxyisoeugenol
(see 4-Propenyl-
2,6-dimethoxyphenol,
no. 3728)
o-Metoxyphenyl acetate
(see Guaiacyl acetate,
no. 3687)
2-Methoxy-4-propenylphenyl
benzyl ether
(see Isoeugenyl benzyl ether,
no. 3698)
3701 Methyl 1-acetoxycyclohexyl
ketone
3702 Methylbenzyl acetate (mixed
o, m,p)
3703 3-Methyl-2-butanol
3704 4-Methyl-2,6-dimethoxyphenol
3705 2-Methyl-1 ,3-dithiolane
3-Methylene-2-octanone
(see 2-Pentyl-1-buten-3-one,
no. 3725)
4-( 1-Methylethyl )-
3-cyclohexene-1-carboxylic
acid (see
1,2 ,5 ,6-Tetrahydrocuminic
acid, no. 3731)
Methyl 2,4-hexadienoate
(see Methyl sorbate, no. 3714)
Methyl (E,E)-2,4-hexadienoate
(see Methyl sorbate, no. 3714)
3706 Methyl2-hydroxy-
4-methylpentanoate
Methyl 2-hydroxyisocaproate
(see Methyl2-hydroxy-
4-methylpentanoate, no. 3706)
(see 3-Methyl-2-butanol,
no. 3703)
Methyl2-keto-3-methylvalerate
(see Methyl2-oxo-
3-methylpentanoate, no. 3713)
Methyl3-methyl-2-oxovalerate
(see Methyl2-oxo-
3-methylpentanoate, no. 3713)
3707 Methyl2-methylpentanoate
3708 Methyl2-methyl thiobutyrate
Methyl2-methylvalerate
(see Methyl
2-methylpentanoate, no. 3707)
3709 Methyl nicotinate
3710 Methyl3-nonenoate
3711 2-Methyl-2-octenal
3712 Methyl trans-2-octenoate
Methyl (E)-2-octenoate
(see Methyl trans-2-octenoate,
no. 3712)
3713 Methyl2-oxo-3-methylpent
2-Methylphenyl
2-hydroxybenzoate
(see o-Tolyl salicylate,
no. 3734)
p-Methylphenyl octanoate
(see p-Tolyl octanoate,
no. 3733)
Methyl 3-pyridinecarboxylate
(see Methyl nicotinate,
no. 3709)
4-Methylsalicylaldehyde
(see 2-Hydroxy-
4-methylbenzaldehyde,
no. 3697)
4-Methylsalicylic aldehyde
(see 2-Hydroxy-
4-methylbenzaldehyde,
no. 3697)
3714 Methyl sorbate
4-Methylsyringol
(see 4-Methyl-
2,6-dimethoxyphenol,
no. 3704)
3715 7-Methyl-4,4a,5,6-tetrahydro-
2(3h)-naphthalenone
3716 4-Methylthiazole
Methylthio 2-methylbutyrate
(see Methyl
2-methylthiobutyrate,
no. 3708)
666 Source Book of Flavors

List No. 13 Continued 3727 1-Phenyl-3 or 5-propylpyrazole

FEMANo. 4-Propenyl-1-(benzyloxy)-
3717 2-(Methylthiomethyl)- 2~methoxybenzene
3-phenylpropenal (see Isoeugenyl benzyl ether,
Methyl tridecyl ketone p.o. 3698)
(see 2-Pentadecanone, 4-Propenyl-
no. 3724) 2,6-dimethoxyphenol
3718 3-Methyl-1 ,2,4-trithiane 4-Propenylsyringol
3719 ~-naphthyl isobutyl ether (see 4-Propenyl-
Neroloxide 2,6-dimethoxyphenol,
(see 3,6-Dihydro-4-methyl- no. 3728).
2-(2-methylpropen-1-yl)- 3729 4-Propyl-2,6-dimethoxyphenol
2H-pyran, no. 3661) 4-Propylsyringol
3720 cis-2-Nonen-1-ol (see 4-Propyl-
(Z)-2-Nonen-1-ol 2,6-dimethoxyphenol,
(see cis-2-Nonen-1-ol, no. 3729)
no. 3720) 3730 L-Rhamnose
Ocimen quintoxide Ritotide
(see 2,2-Dimethyl- (see Disodium 5-guanylate,
5-(1-methylpropen-1-yl)- no. 3668)
tetrahydrofuran, no. 3665) 3731 1,2,5,6-Tetrahydrocuminic acid
3721 trans, trans-2 ,4-0ctadienal (2RS,5SR,6SR)-
(E,E)-2,4-0ctadienal 2,6,10, 10-Tetramethyl-
(see trans, trans- 1-oxaspiro[4,5]dec-6-yl acetate
2,4-0ctadienal, no. 3721) (mixture of C2 epimers)
3722 cis-5-0cten-1-ol (see
(Z)-5-0cten-1-ol 6-Acetoxydihydrotheaspirane,
(see cis-5-0cten-1-ol, no. 3651)
no. 3722) 3732 Thaumatin
3-0ctyl2-methyl-2-butenoate 3733 p- Tolyl octanoate
(see 1-Ethylhexyl tiglate, 3734 o-Tolyl salicylate
no. 3676) a, a,4-Trimethyl-3-cyclohexene-
3-0ctyl2-methylcrotonate 1-methanethiol
(see 1-Ethylhexyl tiglate, (see 1-p-Menthene-8-thiol,
no. 3676) no. 3700)
3-0ctyl tiglate 4-(2,6,6-Trimethyl-
(see 1-Ethylhexyl tiglate, 2-cyclohexenyl)-2-butene-
no. 3676) 4-one
3723 2-0xobutyric acid (see a-Damascone, no. 3659)
3724 2-Pentadecanone 2-(2,2,3-Trimethyl-
3725 2-Pentyl-1-buten-3-one 3-cyclopentenyl)ethyl acetate
6-Pentyl-a-pyrone (see Campholene acetate,
(see 5-Hydroxy- no. 3657)
2,4-decadienoic acid 8-lactone, 3735 2,2,6-Trimethyl-6-vinyltetra-
no. 3696) hydropyran
3726 d,l,Phenylalanine 3736 L-Tyrosine
Phenyl ether 3737 Vanillyl alcohol
(see Diphenyl ether, no. 3667) 3738 Vanillylidene acetone
1-Phenyl-3 or 5-propyl- 3739 p- Vinylphenol
1,2-diazole 2,6-Xylenethiol
(see 1-Phenyl-3 or (see 2,6-Dimethylthiophenol,
5-propylpyrazole, no. 3727) no. 3666)
Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association
List No. 13 Continued
FEMA No.
m-Anisaldehyde, 4-hydroxy,
isobutyrate
(see Vanillin isobutyrate,
no. 3754)
m-Anisaldehyde, 4-hydroxy,
2-methylpropionate
(see Vanillin isobutyrate,
no. 3754)
List No. 14 (Oser et a!. 1985)
FEMANo.
3740 Anisyl phenylacetate
Anisyl a-toluate
(see Anisyl phenylacetate,
no. 3740)
Benzaldehyde, 4-hydroxy,
3-methoxy, isobutyrate
(see Vanillin isobutyrate,
no. 3754)
Benzaldehyde, 4-hydroxy,
3-methoxy,
2-methylpropionate
(see Vanillin isobutyrate,
no. 3754)
3741 a-Campholenic alcohol
a-Campholenol
(see a-Campholenic alcohol,
no. 3741)
o-Cresyl isobutyrate
(see o-Tolyl isobutyrate,
no. 3753)
Cryprocarya massoia
(see Massoia bark oil,
no. 3747)
3742 5- and 6-Decenoic acid
(- )-2-Decenoic acid, 5-hydroxy,
o-lactone
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
3743 2,5-Diethyltetra-hydrofuran
5,6-Dihydro-6-pentyl-
2H-pyran-2-one
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
(R)-5 ,6-Dihydro-6-pentyl-
2H-pyran-2-one
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
( ± )-5,6-Dihydro-6-pentyl-
2H-pyran-2-one
667
1-Ethoxyethyl ether of potassium
lactate
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
(see Potassium 2-(1'
-sthoxy )sthoxypropanoate,
no. 3752)
4-Formyl-2-methoxyphenyl
2-methylpropanoate
(see Vanillin isobutyrate,
no. 3754)
Frescolat
(see /-Menthyl lactate,
no. 3748)
3744 5-Hydroxy-2-decenoic acid
o-lactone
3745 5-Hydroxy-7-decenoic acid
o-lactone
a-Hydroxypropanoic acid,
5-methyl-2-( 1-methylethyl)-
cyclohexyl ester
(see /-Menthyl lactate,
no. 3748)
Isobutyric acid, ester with
vanillin
(see Vanillin isobutyate,
no. 3754)
Jasmin lactone
(see 5-Hydroxy-7-decenoic
acid o-lactone, no. 3745)
3746 Linalool oxide
Massoia bark
(see Massoia bark oil,
no. 3747)
3747 Massoia bark oil
Massoialactone
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
Massoia lactone
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
Massoilactone
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
(R)(-) Massoilactone
(see 5-Hydroxy-2-decenoic
acid o-lactone, no. 3744)
(- )-p-Menthan-3-yllactate
(see /-Menthyl lactate,
no. 3748)
3748 /-Menthyl lactate
p-Methoxybenzyl phenylacetate
668 Source Book of Flavors
List No. 14 Continued
FEMA No.
(see Anisyl phenylacetate,
no. 3740)
3-Methoxy-
4-isobutyrylbenzaldehyde
(see Vanillin isobutyrate,
no. 3754)
2-Methylphenyl
2-methylpropanoate
(see o-Tolyl isobutyrate,
no. 3753)
cis & trans-2-Methyl-2-vinyl-
5(2-hydroxy-
2-propyl)tetrahydro-furan
(see Linalool oxide, no. 3746)
3749 cis-5-0ctenal
(Z)-5-0ctenal
(see cis-5-0ctenal, no. 3749)
3750 Osmanthus absolute
Osmanthus fragrans lour
(see Osmanthus absolute,
no. 3750)
Osman thus fragrans
(see Osmanthus absolute,
no. 3750)
cis- 5-(2-Pentenyl )pentanolide
(see 5-Hydroxy-7-decenoic
acid 8-lactone, no. 3745)
Phenylacetic acid,
p-methoxybenzyl ester
(see Anisyl phenylacetate,
no. 3740)
3751 2-(3-Phenylpropyl)-pyridine
3752 Potassium 2-(1'-ethoxy)-
ethoxypropanoate
Potassium o-(1'
-ethoxy )ethyllactate
(see Potassium 2-(1'
-ethoxy )ethoxypropanoate,
no. 3752)
Propanoic acid, 2-hydroxy,
5-methyl-
2( 1-methylethyl)cyclohexyl
ester [1R-{1a(R*), 2~, 5a}]
(see !-Menthyl lactate,
no. 3748)
Propanoic acid, 2-methyl,
4-formyl-2-methoxyphenyl
ester
(see Vanillin isobutyrate,
no. 3754)
3753 o-Tolyl isobutyrate
o-Tolyl2-methylpropanoate
(see o-Tolyl isobutyrate,
no. 3753)
2,2,3·Trimethyl-3-cyclopentene-
1-ethanol
(see a-Campholenic alcohol,
no. 3741)
2-(2,2,3-Trimethylcyclopent-
3-en-1-yl)ethanol
(see a-Campholenic alcohol,
no. 3741)
3754 Vanillin isobutyrate
Vanillyl isobutyrate
(see Vanillin isobutyrate,
no. 3754)
cis & trans-2-Vinyl-2-methyl-
5-(1'-hydroxy-1'-methylethyl)
tetrahydrofuran
(see Linalool oxide, no. 3746)
List No. 15 (Burdock et a!. 1990)
FEMANo.
3755 Dehydromentho-furolactone
2( 4H)-Benzofuranone,
5,6-dihydro-3,6-dimethyl-,
(R)-
3,6-dimethyl-5,6-dihydro-
2( 4H)benzofuranone
3,6-Dimethyl-4,5-dihydro-
6H-benzo(b) furan-2-one
3756 4-Ethylbenzaldehyde
Benzaldehyde, 4-ethyl
p-Ethylbenzaldehyde
3757 Ethyl methyl-p-tolylglycidate
Ethyl methyl-
p-methylphenylglycidate
Oxiranecarboxylic acid,
3-methyl-3-(4-methylphenyl)-
ethyl ester
3758 5-Hydroxy-8-undecenoic acid
delta-lactone
Jasmolactone extra C
2H-Pyran-2-one,
6-(3-hexenyl)tetrahydro-, (Z)-
3759 5-Isopropenyl-2-methyl-
2-vinylte-trahydrofuran
Anhydro linalool oxide
2-Ethenyl-2-methyl-
5-(1-methylethenyl)
tetrahydrofuran
Furan, 2-ethenyl-tetrahydro-
2-methyl-5-(1-methylethenyl)-
2-Methyl-2-vinyl-
5-isopropenyltetrahydrofuran
Flavoring Ingredients Classified As GRAS By the Flavor Extract Manufacturers Association
ListNo.lS Continued
FEMANo.
3760 1-(4-Methoxyphenyl)-4-methyf-
1-penten-3-one
alpha-p-Dimethylanisalacetone
Isopropyl4-methoxystyryl
ketone
Methoxystyryl isopropyl ketone
1-Penten-3-one,
1-(4-methoxyphenyl)-
4-methyl-
3761 5-Methyl-2-hept-4-one
Filbertone
Hazel tone
2-Hepten-4-one, 5-methyl-
3762 3-Methyl-1-pentanol
2-Ethyl-4-butanol
1-Pentanol, 3-methyl-
3763 3-methyl-2-(n-pentanyl)-
2-cyclopenten-1-one
2-Cyclopenten-1-one, 3-methyl-
2-pentyl-
Dihydrojasmone
2-Pentyl-3-methyl-
2-cyclopenten-1-one
3764 Mintlactone
2( 4H)-Benzofuranone,
5 ,6, 7, 7a-tetrahydro-
3,6-dimethyl-
Dehydroxymenthofurolactone
3,6-Dimethyl-
5,6,7 ,7a-tetrahydro-2(4H)
benzofuranone
3,6-Dionethyl-
4,5,6,7-tetrahydro-
7aH-benzo(b) furan-2-one
3765 Myrtenyl acetate
Bicyclo[3 .1.1 ]hept-2-ene-
21-methanol, 6-6-dimethyl-,
acetate, (1S)-
2,2-Pinene-10-yl-acetate
2-Pinen-10-ol acetate
3766 2-trans-6-trans-Nonadienal
2,6-Nonadienal, (E,E)-
3767 3-0xodecanoic acid glyceride
Glyceryl ester of 3-oxodecanoic
acid
3768 3-0xododecanoic acid glyceride
Glyceryl ester of
3-oxododecanoic acid
3769 3-0xohexadecanoic acid
glyceride
Glyceryl ester of
3-oxohexadecanoic acid
669
3770 3-0xohexanoic acid diglyceride
Glyceryl ester of 3-oxohexanoic
acid
3771 3-0xooctanoic acid glyceride
Glyceryl ester of 3-oxooctanoic
acid
3772 3-0xotetradecanoic acid
glyceride
Glyceryl ester of
3-oxotetradecanoic acid
3773 Sodium 2-(4-methoxy
phenoxy )propanoate
Propanoic acid,
2-(4-methoxyphenoxy),
sodium salt
3774 Theaspirane
1-0xaspiro[4.5]dec-6-ene,
2,6,10,10-tetramethyl-
1-0xaspiro-2,6,10,10-
tetramethyl[4. 5]dec-6-ene
2,6,10,10-Tetramethyl-
1-oxaspiro[4 .5]dec-6-ene
References: FEMA GRAS Listings
Burdock, G.A., Wagner, B.M., Smith, R.L.,
Munro, I.C., and Newberne, P.M. 1990.
Recent progress in the consideration of
flavoring ingredients under Food Additives
Amendment. 15. GRAS substances. Food
Techno/. 44(2):78.
Grundschober, F. et a!. 1975. Survey of world-
wide use levels of artificial flavouring
substances. Int. Flavours Food Additives.
6:223-230.
Hall, R.L. and Oser, B.L. 1970. Recent progress
in the consideration of flavoring ingredients
under Food Additives Amendment. 4. GRAS
substances. Food Techno[. 24(5):25-34.
Oser, B.L. and Hall, R.L. 1972. Recent progress
in the consideration of flavoring ingredients
under Food Additives Amendment. 5. GRAS
substances. Food Techno/. 26(5):35-42.
Oser, B.L. and Ford, R.A. 1973a. Recent pro-
gress in the consideration of flavoring ingre-
dients under Food Additives Amendment. 6.
GRAS substances. Food Techno/. 27(1):64-
67.
Oser, B.L. and Ford, R.A. 1973b. Recent
progress in the consideration of flavoring
ingredients under Food Additives Amend-
ment. 7. GRAS substances. Food Techno/.
27(11):56-57.
Oser, B.L. and Ford, R.A. 1974. Recent
progress in the consideration of flavoring
670 Source Book of Flavors
ingredients under Food Additives Amend-
ment. 8. GRAS substances. Food Techno[.
28(9):76-77, 80.
Oser, B.L. and Ford, R.A. 1975. Recent pro-
gress in the consideration of flavoring
ingredients under Food Additives Amend-
ment. 9. GRAS substances. Food Techno[.
29(8):70-72.
Oser, B.L. and Ford, R.A. 1977. Recent
progress in the consideration of flavoring
ingredients under Food Additives Amend-
ment. 10. GRAS substances. Food Techno[.
31(1):65-67, 70, 72, 74.
Oser, B.L. and Ford, R.A. 1978. Recent
progress in the consideration of flavoring
ingredients under Food Additives Amend-
ments. 11. GRAS substances. Food Techno!.
32(2):60-62, 64-66, 68-70.
Oser, B.L. and Ford, R.A. 1979. Recent
progress in the consideration of flavoring
ingredients under the Food Additives
Amendment. 12. GRAS substances. Food
Techno!. 33(7):65- 73.
Oser, B.L., Ford, R.A., and Bernard, B.K.
1984. Recent progress in the consideration of
flavoring ingredients under Food Additives
Amendment. 13. GRAS substances. Food
Techno[. 32(2):60.
Oser, B.L., Wei!, C.S., Woods, L.A., and
Bernard, B.K. 1985. Recent progress in the
consideration of flavoring ingredients under
Food Additives Amendments. 14. GRAS
substances. Food Techno[. 33(7):65.
Chapter 14
Flavor Patents
The flavor industry is less likely to patent an
invention or idea than most other segments
of the industrial sector. The flavor industry
has traditionally depended upon trade
secrets rather than patents for protection.
Filing a patent effectively discloses the
process or compound that the industry is
attempting to protect. This is particularly
important since patent infringement may be
extremely difficult to prove in the flavor
industry. For example, if one patents the
use of a flavor compound, this compound,
with few exceptions already exists in nature
and may be available from several sources
(flavoring materials or ingredients). While
these sources may be an impractical source
of a given chemical, nevertheless the
chemical could find its way into a given
application from a "legitimate" source.
Thus, if one can find this compound being
used in an application, is it there naturally,
as a contaminant of some other constituent,
has it been arrived at by another non-
infringing approach or does its presence, in
fact, constitute patent violation?
While some flavor patents are used in
areas where they can provide protection,
patents often serve a different function: that
of providing visibility to a company. Most of
the patents granted in the flavor industry are
to publicly held companies. Patents serve to
demonstrate leadership or productivity of
the company to its stockholders.
The patent compilation that follows was
generated using a key word search of the
FSTA (Food Science and Technology
Abstracts). The key words searched were
"aroma," "flavor" and "flavour." The
patent literature was searched from 1981
to 1991. Patents prior to 1981 have been
covered by Heath (1981) and are not in-
cluded here. The patents are presented
chronologically by title to indicate subject
matter. In some cases, descriptive terms
have been added in parentheses to assist in
determining subject matter, if the title is
not sufficiently descriptive. Not all of the
patents related to the synthesis of flavor
compounds or potential applications of
these compounds have been included in this
compilation. One should also note that the
granting of a patent does not imply that a
flavor compound is approved for use in
foods.
Most large public libraries have access to
United States patents. Domestic patents
can also be obtained from: Commissioner
of Patents and Trademarks, Box 10,
Washington, D.C. 20231. The current cost
of a United States patent is $1.50.
671
672 Source Book of Flavors
PATENTS
1990
Ansaldi, G., Gil, G., and Petit, J. Ia-, 1990.
Process for production of natural vanilla
aroma by treatment of green vanilla pods, and
the aroma so produced. French Patent
Application. FR 2 634 979 Al.
Byrne, B., Miller, K.P., Tan, C.-T., Bucholz,
L.L. Jr., and Sudol, M.A. 1990. Process for
microwave chocolate flavor formation in
and/or on foodstuffs and products produced
thereby. United States Patent. 4 940 592.
Buckholz, L.L. Jr., Byrne, B., and Sudol, M.A.
1990. Process for microwave browning and
product produced thereby. United States
Patent. 4 904 490.
Budai, J. 1990. Method for producing differently
flavoured, particularly quick-frozen and/or
snack meals covered with an edible packing,
especially with a product of the baking in-
dustry. PCT International Patent Application.
WO 90/00860 Al.
Chesse, C., Richard, H., and Piriou, B. 1990.
Process for preparation of natural truffle
aroma and the products so prepared. French
Patent Application. FR 2 637 779 Al.
Clauzure, A.C. 1990. Process for preparation
of a colourless aqueous solution of flavour
compounds and its application to manufacture
of a colourless spirit of the whiskey type.
French Patent Application. FR 2 634 494 Al.
Doerfel, K., Heinig, R., and Strueber, F.J. 1990.
Process for preparation of a peach-like
flavour/aroma concentrate. German Demo-
cratic Republic Patent. DD 277 206.
Douwe Egberts Koninklijke. Tabaksfabriek-
Koffiebranderijen-Theehandel NV. 1990.
Process for increasing the content of aroma
compounds in coffee. Netherlands Patent
Application. NL 88 01 777 A.
Hoppe, K. 1990. Process for manufacture of
a bread-like flavour/aroma preparation.
German Democratic Republic Patent DD 278
273.
Odermatt, R.G., and Saxer, M. 1990. Process
for manufacture of special dry, particulate
flavoured bread for bread dumplings. Swiss
Patent. CH 672 973 A5.
Schulmeyr, J. 1990. Process for flavouring of
processed tea. German Federal Republic
Patent Application. DE 38 38 952 Al.
Tothne-Papay, V., Toth, V.K., and Toth, T.
1990. Process for producing light- and heat-
resistant, biologically active extracts, juices
and products rich in vitamin C, flavour, aroma
and colouring substances, as well as for
producing pharmaceuticals, cosmetics, food-
stuff, nutriments, fodder and materials yield-
ing biological protection containing the
above extracts, juices and products as active
ingredients. PCT International Patent
Application. WO 90/01270 Al.
Walpuski, J., Kruse, H.P., and Hoppe, K. 1990.
Process for manufacture of cocoa powder
substitutes with natural flavour components.
German Democratic Republic Patent. DD
275 394.
1989
Adda, J. and Lorne, J.L. 1989. Process for
extraction of volatiles with supercritical C02 ,
and the compounds so obtained. French
Patent Application. FR 2 629 735 Al.
Aeschbach, R. and Philippossian, G. 1989.
Preparation of a spice extract having anti-
oxidant action. European Patent Application.
EP 0 307 626 Al.
Alekseev, V.P., Grunin, E.A., and Ustinnikov,
B.A. 1989. Method of producing an aroma
concentrate from fruit juice. USSR-Patent.
su 1 493 233.
Anandaraman, S., Ozogar, R.M., and
Bergsbaken, C.K. 1989. Non-bitter enzyme
modified cheese flavoring material and spray
dried product. United States Patent. 4 853
232.
Barcelon, S.A., Hussein, M.M., Abbazia, L.P.,
and Graff, A.H. 1989. Unique flavor com-
position. United States Patent. 4 820 544.
Billings, J.H. 1989. Malt beverages with im-
proved flavor and method of making same.
United States Patent. 4 816 280.
Brouard, F.E.M.E., Baynast-de-Septfontaines,
R.J.M.P.-de. 1989. Process for production of
liquid flavour bases. French Patent Applica-
tion. FR 2 625 750 Al.
Bruijnje, A., Heideman, T., Wille, H.J. 1989.
Alkyl (3-methylthio)-butyrates, as well as
flavour compositions and flavoured foodstuffs
and stimulants containing one or more of
these compounds [which impart a fresh fruit
flavour] as flavour component. European
Patent Application. EP 0 330 254 Al.
Buckholz, L. and Stypula, R.J. 1989. Flavour-

retaining food product. European Patent
Application. EP 0 306 000 A2.
Callahan, T. and Herz, J. 1989. Flavor and
texture improved canned animal flesh and
process. United States Patent. 4 871 575.
Chang-Diaz, F.R. 1989. Method of infusion
extraction. United-States-Patent. 4 832 951.
Cherukuri, S.R., Faust, S.M., and Orlandi,
D.A. 1989. Flavor and sweetness enhance-
ment delivery systems and method of prep-
aration. United States Patent. 4 803 082.
Cherukuri, S.R., Faust, S.M., and Orlandi,
D.A. 1989. European Patent Application. EP
0 314 626 A2.
Cooley, J. and Douglas, D. 1989. Method for
producing flavored popcorn. United States
Patent. 4 888 186.
Dave, J.C., Record, D.W., Nespor, J.M., and
Hook, J.S. 1989. Using cocoa powder to
enhance the flavor of a mint-flavored chewing
gum. United States Patent. 4 889 726.
Dave, J.C., Record, D.W., Nespor, J.M., and
Hook, J.S. 1989. Using cocoa powder to
enhance the flavor of synthetic chewing gum
base. United States Patent. 4 889 727.
Deublein, D. 1989. Process and device for
flavouring, alkali treatment, refining, steril-
ization and roasting of cocoa mass. German
Federal Republic Patent Application. DE 38
13 615 Al.
Duboc, S., Laugier, S., Pean, J.L., Renon, H.,
and Mizandjian, J.L. 1989. Process for prep-
aration of spice extracts. French Patent
Application. FR 2 632 826 Al.
Ehrman, A.M., Seiden, P., Weitzel, R.M., and
White, R.L. 1989. Process for tempering
flavored confectionery compositions con-
taining reduced calorie fats and resulting
tempered products. United States Patent. 4
888 196.
Franzke, C., Meisel, D., Kroll, J., and Paul, W.
1989. Process for preparation of cocoa butter
aroma concentrate. German Democratic
Republic Patent. DD 265 074.
Gillmore, S.R., Merritt, C. G., and Epstein, A.l.
1989. One-step flavored pasta products.
European Patent Application. EP 0 314 265
Al.
Gray, R.D. and Gray, T.J. 1989. Sea food-
flavored food products. United States Patent.
4 888 181.
Greene, L.M. 1989. Nutmeg emulsion and
process for making same. United States
Patent. 4 832 974.
Flavor Patents 673
Gunata, Z., Bitteur, S., Baumes, R., Brillouet,
J.M., Tapiero, C., Bayonove, C., and
Cordonnier, R. 1989. Process for recovery of
aroma and flavour compounds from glycosidic
precursors, and the aromas and flavours so
produced. French Patent Application. FR 2
628 439 Al.
Hantsche, G., Kliefoth, J., Krell, L., Kuenne,
H.J., Michel, W., Moerl, L., and
Winkelmann, M. 1989. Process for preser-
vation of the aroma of roast coffee. German
Democratic Republic Patent. DD 268 150.
Hantsche, G., Kliefoth, J., Krell, L., Kuenne,
H.J., Michel, W., Moerl, L., Roebert, L.,
and Winkelmann, M. 1989. Process for sta-
bilization of the aroma of ground coffee.
German Democratic Republic Patent. DD
268 151.
Haring, P.G.M. 1989. Process for the prep-
aration of a flavoured foodstuff as well as a
foodstuff obtainable by such a process.
European Patent Application. EP 0 298 552
Al.
Hartman, G. 1989. Flavoring material possessing
fermented soy sauce characteristics. United
States Patent. 4 874 625.
Heyland, S., Roeschli, D., Rolli, K., and Sihver,
J.J. 1989. Process for preparation of a flav-
ouring. Swiss Patent. CH 670 743 AS.
Hulsker, F.H., Jong, K. de-, and Turksma, H.
1989. Process for concentrating lactones,
as well as the use of the concentrate thus
obtained for flavouring foodstuffs. European
Patent Application. EP 0 321 056 Al.
Inayoshi, K., Egawa, Y., Hirukawa, Y., and
Yamaguchi, M. 1989. Whipped oily flavor.
United States Patent. 4 869 915.
Ivanov, E.L., Kovalev, N.l., Smolentseva,
A.A., Romanyuk, S.S., and Samar, S.Y.
1989. Preparation and distribution of flav-
oured soups. USSR-Patent. SU 1 494 900.
Josephson, D.B. 1989. Process for masking a
cooked flavour in heated milk. United States
Patent. 4 851 251.
Karst, F. and Vladescu, B.D.V. 1989. Micro-
biological process for preparation of terpene
flavours. French Patent Application. FR 2 622
208 Al.
Kasten, H. 1989. Process and device for in-
fluencing the flavour of liquids when they
flow through a syphon, drinking straw, etc.
German Federal Republic Patent Applica-
tion. DE 37 31 058 Al.
Kibler, L.A., Kratky, Z., and Tandy, J.S. 1989.
674 Source Book of Flavors
Mushroom flavour. European Patent Appli-
cation. EP 0 288 773 A2.
Knuth, M.E. and Sahai, O.P. 1989. Flavor
composition and method. PCf International
Patent Application. WO 89/00820 Al.
Kuss, G.E. 1989. Meat-flavored vegetable oil
preparation method and product. United
States Patent. 4 86S 868.
Lieske, B., Konrad, G., Deistel, 0., and
Faenger, H. 1989. Process for preparation of a
natural chicken flavour concentrate. German
Democratic Republic Patent. DD 272 031.
Mathers, J.J. 1989. Methods for partitioning of
organic flavor compounds. United States
Patent. 4 86S 991.
Maurer, B. and Hauser, A. 1989. Use of (E)-
4,8-dimethyl-1,3,7-nonatriene as a flavouring
and aromatising agent. Swiss Patent. CH 668
910 AS.
Milton, P.J. 1989. Flavouring food. UK Patent
Application. GB 2 206 473 A.
Missire, P.M.A. 1989. Ready-to-use powdered
seasoning for imparting a mushroom flavour
to foods. French Patent Application. FR 2 618
OS6 Al.
Mookherjee, B.D., Trenkle, R.W., Calderone,
N., Sands, K.P., and Hagedorn, M.L. 1989.
Use of Schiff base reaction product of methyl
anthranilate and canthoxal in augmenting or
enhancing aroma or taste of foodstuff or
chewing gum. United States Patent. 4 840 801.
Mookherjee, B.D., Trenkle, R.W., Calderone,
N., and Sands, K.P. 1989. Flavoring with
Schiff base reaction products of alkyl an-
thranilates [e.g., for foodstuffs and chewing
gum]. United States Patent. 4 806 363.
Naarden International NV. 1989. Alkyl-(3-
methylthio )butyrates, and flavourings or
flavoured foods containing one or more
of these compounds. Netherlands Patent
Application. NL 88 00 S02 A.
Ochsner, P.A. 1989. Hexanoates, process for
their manufacture, and aroma and flavour
compositions containing them. European
Patent. EP 0 177 807 Bl.
Oppenheimer, A., Glass, M., and Cherukuri, R.
1989. Chewing gum and confectionery com-
position containing a soy flavor enhancer.
United States Patent. 4 832 962.
Osawa, H. 1989. Method of stably fixing aro-
matic coffee substance. United States Patent.
4 820 S43.
Parliment, T.H., Cipriano, J.J., and Scarpellino,
R. 1989. Aroma release during microwave
cooking. United States Patent. 4 8S7 340.
Pawlak, J.Z. and Kinzbach, J. 1989. Method
for making potato chips having batch-fried
texture and flavor. United States Patent. 4 863
7SO.
Piotrowski, R.D., Ross, G.R., Strobel, R.G.K.,
Thundathil, R.V., and Tsai, C.H. 1989.
Method of making low-viscosity evaporative
orange juice concentrates having less cooked
off-flavor. United States Patent. 4 818 SSS.
Pittet, A.O., Muralidhara, R., and Hagedorn,
M.L. 1989. Process for preparing 4,4A,S,6-
tetrahydro- 7- methyl- 2- (3H)- naphthalenone,
intermediates used in said process and novel
crystalline form of same (for use as aroma and
flavour enhancers). United States Patent.
4 794 193.
Pratt, N.G. 1989. Preparation of a blue cheese
flavour. United States Patent. 4 832 964.
Quendt, H. and Schlinzig, E. 1989. Process
for improvement of the flavour of food ex-
trudates. German Democratic Republic
Patent. DD 266 9S9.
Schulman, M., Hannah, H., Stevenson, R.B.,
and Case-GP. 1989. Process to produce a
charcoal broiled flavor. United States Patent.
4 820 S38.
Shoseyov, 0., Chet, 1., Bravdo, B.A., and Ikan,
R. 1989. Flavor and fragrance enhancing
enzymes. European Patent Application. EP 0
307 071 A2.
Smith, P.F. and Geals, D.W. 1989. Manufacture
of cheese flavor powder. United States
Patent. 4 826 693.
Specht, P., Heinicke, B., Sliva, F., Straube, H.,
and Werner, H. 1989. Process for flavouring
of beer. German Democratic Republic
Patent. DD 269 39S.
Spies, G. 1989. Water-soluble extract with bread-
like aroma, process for its manufacture and
device for implementation of the process.
Swiss-Patent. CH 671 677 AS.
St. Angelo, A.J. and Vercellotti, J.R. 1989.
Inhibition of warmed-over flavor and pre-
serving of uncured meat containing materials.
United States Patent. 4 871 SS6.
Takenawa, S., Takeda, H., and Horikoshi, M.
1989. A composition for eliminating dis-
agreeable odor from soya milk and a process
for preparation of soya milk with an improved

flavor. European Patent Application. EP 0
328 322 A2.
Zeiler, H., Ackermann, M., Winkler, H., Belke,
D., Zabel, W., and Richter, K. 1989. Process
for preparation of natural alcoholic aroma
extract. German Democratic Republic
Patent. DD 267 509.
1988
Ameyama, M., Adachi, 0., Yasuda, A., and
Nomura, Y. 1988. Method of reducing off-
flavour in food materials with acetic acid
bacteria. European Patent Application. EP 0
255 588 A2.
Antonucci-Tarolla, M.S. 1988. System for
aromatizing foods. European Patent Applica-
tion. EP 0 259 274 Al.
Arbige, M. V. and Neubeck, C.E. 1988. Lipolytic
enzyme derived from an Aspergillus micro-
organism having an accelerating effect on
cheese flavor development. United States
Patent. 4 726 954.
Barcelon, S.A., Oppenheimer, A., and Hussein,
M.M. 1988. Taste and odor masked edible oil
compositions. European Patent Application.
EP 0 296 117 A2.
Bayerlein, F., Kottmair, N., Maton, M.M.,
Keramaris, N., and Kuhn, M. 1988. Prep-
aration of colourless, flavour- and odour-
neutral Cassia endosperm flour. German
Federal Republic Patent. DE 36 34 645 Cl.
Byrne, B. 1988. Flavoring method and com-
position. United States Patent. 4 781 762.
Calabro, F.P., Glass, M., Hussein, M.M., and
Militescu, C. 1988. Sequentially flavored
chewing gum composition. European Patent
Application. EP 0 289 462 A2.
Calabro, F.P., Glass, M., Hussein, M.M., and
Militescu, C. 1988. Sequentially flavored
chewing gum composition. United States
Patent. 4 775 537.
Calandro, T.P., DeLauder, W.R., and Verrico,
M.K. 1988. Process for the production of a
flavored cereal product. United States Patent.
4 755 390.
Carroll, T.J. and Hopkins, W.R. 1988. Sweet
flavorful soft flexible sugarless chewing gum
and process for preparing same. European
Patent Application. EP 0 262 678 A2.
Chen, T.K. and Tandy, J.S. 1988. Production of
flavour. European Patent Application. EP 0
Flavor Patents 675
295 509 Al.
Cherukuri, S.R., Mansukhani, G., and Jacob,
K.C. 1988. Stable cinnamon-flavored chewing
gum composition. United States Patent. 4 722
845.
Cherukuri, S.R., Hansukhani, G., and
Kapakkamannil, C.J. 1988. Stable cin-
namon-flavored chewing gum composition.
European-Patent-Application. EP 0 273 857
A2.
Curade, M. 1988. Flavoured honeys and their
preparation. French Patent Application. FR 2
608 378 Al.
Delmas, M., Gaset, A., Montant, C., Pebeyre,
P.J., and Talou, T. 1988. Process for prep-
aration of a flavour and aroma composition
resembling black truffles, the flavour/aroma
composition produced, and flavoured items.
French Patent Application. FR 2 601 857 Al.
Delmas, M., Gaset, A., Montant, C., Pebeyre,
P.J., and Talou, T.1988. Black truffle flavour.
European Patent Application. EP 0 257 666
Al.
Desmettre, M.G.G. 1988. Confectionery item
with flavour reserve. French Patent Applica-
tion. FR 2 604 061 Al.
Dokuzovic, Z. 1988. Flavor emulsions and
chewing gum compositions containing the
same. United States Patent. 4 752 481.
Fulger, C.V. and Lou, W.C. 1988. Process
for preparing a heat stable fermented malt
flavorant. United States Patent. 4 752 482.
Gilmore, L.T. 1988. Process for preparing a
caramel butterscotch flavour syrup. United
States Patent. 4 753 814.
Godfrey, J.C. 1988. Flavor of zinc supplements
for oral use. United States Patent. 4 758 439.
Guigou, B. 1988. Alcohol-containing product for
flavouring of foods and process for its prep-
aration. French Patent Application. FR 2 603
459 Al.
Gupta, R.P. and Gupta, R.R. 1988. Equipment
for making no-beany flavor soymilk. United
States Patent. 4 744 524.
Hagberg, E. C., Haislip, J.R., and Johnson, B.R.
1988. Method for producing a highly flavored
cheese ingredient. United States Patent. 4 752
483.
Hauslein, R. 1988. Process and device for prep-
aration of flavour extracts from coffee.
German Federal Republic Patent Applica-
tion. DE 37 15 165 Al.
676 Source Book of Flavors
Holzner, G., Kittner, P.W., and Blake, A. 1988.
Flavoured food product or seasoning.
European Patent Application. EP 0 284 790
A2.
Isaac, 0., Carle, R., and Doelle, B. 1988.
Process for the production of camomile
extracts rich in flavones. United States Patent.
4 786 498.
Kanisawa, T. and ltoh, H. 1988. Method for
preparing green aroma compounds. United
States Patent. 4 769 243.
Kimizuka, A., Ueda, Y., Sakaguchi, M., and
Miyajima, R. 1988. Flavor enhancing sea-
soning containing deodorized garlic extract
and process. United States Patent. 4 741 914.
Konishi, G.A. and Davy, P.F. 1988. Aerosol
food flavoring compositions. United States
Patent. 4 788 068.
Kratky, Z. and Vadehra, D.V. 1988. Flavouring
composition. European Patent Application.
EP 0 284 739 A2.
Lavoillotte, M. 1988. Water solubility and lipid
miscibility of natural food flavours and emul-
sifiable natural flavours. French Patent
Application. FR 2 615 363 Al.
Lebeault, J.M., Nonus, M., and Revas, S. 1988.
Preparation of pressed cooked curd-type
cheese aroma products or cheese analogues
from granular curd. French Patent Applica-
tion. FR 2 606 255 Al.
Leiske, B. and Konrad, G. 1988. Process for
preparation of a flavour preparation with a
chicken-like flavour. German Democratic
Republic Patent. DD 260 648.
Lieske, B. and Konrad, G. 1988. Process for
manufacture of modified protein hydrolysates
with a chicken meat flavour. German Demo-
cratic Republic Patent. DD 260 387.
Mai, J., Gobbo, S.A., Breitbart, D.J., and
Fischer, C.D. 1988. Food product. (Prep-
aration of aroma isolates.) European Patent
Application EP 0 294 177 A2.
Merritt, C.G. and Gillmore, S.R. 1988. Method
for the preparation of flavored popping corn.
United States Patent. 4 767 635.
Mirande, H. 1988. Process for improvement of
the flavour quality of fermentation products
and apparatus for implementation of the
process. French Patent Application. FR 2 617
184 Al.
Naegeli, P. and Rohr, M. 1988. Aroma and/or
flavour compositions containing unsaturated
acids. European Patent. EP 0 073 984 Bl.
Naipawer, R.E., Rohr, M., and Potter, R.H.
1988. Flavour compositions contammg
campholenic alcohol or derivatives thereof.
European Patent. EP 0 116 903 Bl.
Pierre, J.P. 1988. Process and device for flav-
ouring of whipped cream. French Patent
Application. FR 2 604 604 Al.
Piotrowski, R.D., Ross, G.R., Strobel, R.G.K.,
Thundathil, R.V., and Tsai, C.H. 1988. Low-
viscosity evaporative orange juice concen-
trates having less cooked off-flavor. European
Patent Application. EP 0 292 046 A2.
Rausch, W. 1988. Process for flavouring of tea
and similar products in infusion bags. German
Federal Republic Patent Application. DE 37
01 230 Al.
Rohr, M., Potter, R.H., and Naipawer, R.E.
1988. Flavoring with alpha-campholenic
alcohol. United States Patent. 4 766 002.
Rothe, M., Kornelson, C., Roedel, W., Ruttloff,
H., and Paul, W. 1988. Manufacture of a
butter flavour preparation on the basis of
lipolysis of butterfat. German Democratic
Republic Patent. DD 257 011.
Rothe, M., Koerner, D., Herrmann, H., and
Ruttloff, H. 1988. Process for recovery of
flavour substances or flavour concentrates.
German Democratic Republic Patent. DD
258 174.
Rougereau, A. 1988. Preparation of flavour
extracts from materials of animal or plant
origin. French Patent Application. FR 2 609
238 Al.
Schaaf, H.J. 1988. Preparation of foods from, or
modification of the flavour, of materials of
plant origin. German Federal Republic Patent
Application. DE 36 35 980 Al.
Schaaf, H.J. 1988. Process for manufacture of
products for human consumption from, or
alteration of the flavour of, materials of plant
origin. European Patent Application. EP 0
264 789 A2.
Schindler, F. 1988. Preparation of a mushroom
flavour in fungal biomass. German Federal
Republic Patent Application. DE 37 08 932
Al.
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680 Source Book of Flavors
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686 Source Book of Flavors
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688 Source Book of Flavors
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277.
Pickenhagen, W. and Velluz, A. 1982. alpha-
beta-unsaturated aldehydes and their use as
aromatizing ingredients. Swiss Patent. CH
632 650 A5.
Pickenhagen, W. and Velluz, A. 1982. Flavoring
with alpha, beta-unsaturated aldehydes.
United States Patent. 4 324 809.
Silich, A.A., Slovachevskaya, E.I., and
Evstrat'eva, N.D. 1982. Production of fruit
flavourings. USSR Patent. 904 651.
Smits, J.W. and Timmerrnans, F.A. 1982. Liquid
smoke concentrate. UK Patent. GB 2 011
241 B.
Sprecker, M.A. 1982. Flavoring with norbornyl
ethers and esters. United States Patent. 4 315
945.
Stipp, G.K. 1982. Direct condensation of food
volatiles onto a food substrate at cryogenic
temperatures. United States Patent. 4 335
149.
Suzuki, M. and Matsumoto, T. 1982. Method for
improving the flavour of a chilled dessert.
Japanese Examined Patent. JP 57 46 348 B2.
Takasago Koryo Kogyo KK. 1982. Flavoring
agent. Japanese Examined Patent. JP 57 21
171 B2.
Wiegers, W.J., Sprecker, M.A., Watkins,
H., Vock, M.H., and Schmitt, F.L. 1982.
Flavoring with indane alkanols and tricyclic
isochromans. United States Patent. 4 315 951.
1981
Asahi Kasei Kogyo KK. 1981. Flavour extraction
process. Japanese Examined Patent. 5 611
424.
Boden, R.M. 1981. Flavoring with 1-ethoxy-1-
ethanol acetate. United States Patent. 4 296
137.
Boden, R.M. 1981. Flavoring with 1-n-butoxy-1-
ethanol acetate. United States Patent. 4 296
138.
Bosco, P.M. and Sledzieski, W.L. 1981. Low-fat,
butter-flavored, liquid spread and process.
United States Patent. 4 292 333.
Bruemmer, J.H. 1981. Method of preparing
citrus fruit sections with fresh fruit flavor and
appearance. United States Patent. 4 284 651.
Bush, H.S. 1981. Burnt sugar caramel flavoring
and process of making. United States Patent.
4 272 299.
Fuji, Seiyu KK. 1981. Peanut flavour improve-
ment. Japanese Examined Patent. 5 636 898.
Fukazawa, J., Takeshita, Y., and Kawanishi, S.
1981. Improvements in flavourings for dairy
products made with dried skim milk. Japanese
Examined Patent. JP 56 50 946 B2.
Givaudan & Cie SA. 1981. Flavouring agents.
British Patent. 1 590 148.
Guggenbuehler, M. and Heyland, S. 1981.
Process for the production of a flavouring
agent. (Reaction flavors). UK Patent Applica-
tion. 2 066 041A.
 Flavor Patents 689

Herta KG Karl Schweisfurth. 1981. Method for United States Patent. 4 259 507.
giving taste or aroma to preferably pre- Shu, C.K., Mookherjee, B.D., and Vock, M.H.
aromatised or spiced food stuffs. German 1981. Flavoring with 3,5-di-(2-methylpropyl)-
Federal Republic Patent Application. 2 928 1,2,4-trithiolane. United States Patent. 4 293
680. 579.
Hutchison, W.A. and DeVore, S.R. 1981. Smith, W.J. 1981. Flavor enhancer. United
Method for improving the odor, flavor and States Patent. 4 288 464.
color of canned ocean clam product. United Sprecker, M.A., Schmitt, F.L., Vock, M.H.,
States Patent. 4 279 934. Vinals, J.F., and Kiwala, J. 1981. Use of
Iwasaki, K., Suzuki, Y., and Kikuchi, T. 1981. 1,3 ,5 ,5-tetramethyl-2-oxabicyclo(2.2-2)octane
Method for making a flavouring. (Enzymatic in augmenting or enhancing the aroma or
process). Japanese Examined Patent. JP 56 50 taste of foodstuffs. United States Patent. 4 269
554 B2. 862.
Kaiser, R. 1981. 1,4-epoxy-1,3,3-trimethyl-2-(2- Sprecker, M.A., Vock, M.H., Schmitt, F.L.,
buten-1-ylidene)cyclohexanes as flavorants. Vinals, J., and Kiwala, J. 1981. Flavoring with
United States Patent. 4 258 071. a mixture of acetyl hydrindacenes and acetyl
Kikkoman Shoyu KK. 1981. Soybean paste indanes. United States Patent. 4 305 967.
flavour improvement. Japanese Examined Sprecker, M.A., 1981 Schmitt, F.L., Vock,
Patent. 5 614 264. M.H., Vinals, J.F., and Kiwala, J. 1981. Use
Koepsel, M. and Emberger, R. 1981. Use of of cyclohexenemethanols in augmenting or
di- and tetrahydrobenzofuran derivatives as enhancing the aroma or taste of foodstuffs.
perfuming or aromatizing substance, and United States Patent. 4 265 923.
perfuming and aromatizing compositions con- Sprecker, M.A., Schmitt, F.L., Vock, M.H.,
taining them. German Federal Republic Vinals, J.F., and Kiwala, J. 1981. 2-
Patent Application. 3 017 068. oxabicyclooctane derivatives for augmenting
Monsato Co .. 1981. Stabilized flavouring agent. or enhancing the flavor of foodstuffs. United
Japanese Examined Patent. 5 621 375. States Patent. 4 263 149.
Nihon Lever Industries. 1981. Encapsulated T. Hasegawa Co. 1981. Flavoring agents.
flavouring of oil. Japanese Examined Patent. Japanese Examined Patent. 5 616 781.
5 636 891. Tokai Kasei KK. 1981. Flavoring agent. Japanese
Oetker Tiefkuehlkost GmbH. 1981. Method of Examined Patent. 5 614 253.
applying flavourings and edible fats onto Trenkle, R.W., Mookherjee, B.D., Hall,
deep-frozen foods. UK Patent Application. 2 J.B., Kasper, R., Vock, M.H., Schreck,
051 549A. R., Granda, E.J., and Vinals, J.F. 1981.
Pickenhagen, W. 1981. Flavoring with alpha, Use of 1-hydroxy-1-ethynyl-2,2,6-trimethyl
beta-unsaturated aldehydes. United States cyclohexane in augmenting or enhancing the
Patent. 4 283 433. aroma or taste of foodstuffs. United States
Riken Koryo Kogyo KK. 1981. Protein flavour Patent. 4 284 654.
improvement. Japanese Examined Patent. 5 Wargel, R.J., Greiner, S.P., and Hettinga, D.H.
628 499. 1981. Process and products for the manufac-
Schroedter, R., Woelm, G., and Beik, K. 1981. ture of cheese-flavored products. United
Process for preparation of a concentrate States Patent. 4 244 971.
with meat-like flavour. German Democratic Winter, M., Gautschi, F., Flament, I., Stoll,
Republic Patent. 152 052. M., and Goldman, M. 1981. Flavoring with
Shu, C.K., Mookherjee, B.D., and Vock, M.H. pyrazine derivatives. United States Patent. 4
1981. Flavoring with mixture of 2,5-dimethyl- 303 689.
3-acetyl-furan and 3,5-di-(2-methylpropyl)- Winter, M. 1981 Heterocyclic derivatives as
1,2,4-trithiolane. United States Patent. 4 263 flavoring agents. United States Patent. 4 262
331. 030.
Shu, C.K., Mookherjee, B.D., and Vock, Withycombe, D.A., Mookherjee, B.D.,
M.H. 1981. 3,5-Di-(2-methylpropyl)-1,2,4- Mussinan, C.J., Vock, M.H., and Giacino, C.
trithiolane and uses thereof for augmenting or 1981. Use of 2(2' -methylthiopropyl)-4,5-
enhancing the flavor or aroma of a foodstuff. dimethyl-3-thiazoline to augment or enhance
690 Source Book of Flavors

the aroma or taste of mashed potato flavor M.H., and Vinals, J.F. 1981. Mixtures con-
or mashed potato flavored foodstuffs. United taining isobutyl substituted heterocyclic com-
States Patent. 4 263 332. pounds and flavor use thereof. United States
Withycombe, D.A., Mookherjee, B.D., Vock, Patent. 4 260 641.
Chapter 15
The Flavorist
RESPONSIBILITIES
Reading a series of papers presented
at a symposium of the Society of Flavor
Chemists at Rutgers University in March
1974, it must be recognized that in his or
her domain, a flavorist is expected to be
all things to all people. The flavorist'~
capabilities have to embrace many widely
different activities and he or she must be:
an artist (DiGenova 1974); a biochemist
(Wiener 1974); an internationalist (Bauer
1974); a processor (Bonica 1974); a tech-
nical man (Perry 1974) and a salesman
(Wesley 1974). The flavorist frequently has
to participate in research and development
projects, and must have a basic under-
standing of the techniques employed by the
research chemist (Vock 1974). Also, there
is a constant involvement with application
technologists in the area of product develop-
ment (Katz 1970), extending to the com-
mercial world as the flavorist may be called
upon to provide support for the sale of the
flavorings he has created. In addition to this,
the flavorist must increasingly be involved
with current legislative problems and dis-
play a social responsibility toward con-
sumers (Downer 1974).
In defining the designation "flavorist,"
Cowley (1973) did so in the form of a
job description listing the following major
activities: (a) the creation of flavorings to
meet the needs of present and potential
users; (b) the application and marketing
presentation of flavorings; and (c) to act as a
technical advisor to users of flavorings in
compliance with legislation worldwide.
Obviously, this list becomes further
extended when the day-to-day interfaces of
the above, within a flavor manufacturing
company and external to it, are taken into
consideration. From the outset, this calls
for a person with a very wide-ranging view
of the profession, which is required to be
complementary to the vast areas of organic
chemistry on the one hand and food tech-
nology on the other. The selection of trainees
for this exacting but fulfilling vocation
demands the careful appraisal of those
qualities considered essential to the making
of a good flavorist. While five years as a
trainee is required to formally become a
flavorist, one multinational flavor company
considers that it takes up to ten years of
practical training before a trainee can really
be classified as a "flavorist."
691
692 Source Book of Flavors

ATTRIBUTES
The food industry is a very dynamic
industry, introducing literally thousands of
new products to the market yearly. These
new products generally require flavoring
systems to be most attractive to the con-
sumer. The specialists who create these
flavors, the flavorists, are in short supply.
The extremely specialized and applied
nature of the profession results in there
being few academic courses available for
training. Most university food technology
courses allocate minimal time to flavor
topics. As a consequence, those who choose
to become flavorists must be trained within FIGURE 15-1. Flavor creation. (Courtesy of
the flavor industry itself. Although this Robertet Flavors, Inc .)
poses problems, particularly with mobility
of labor, this training process has been in
operation relatively successfully over a long
Character
time and is likely to continue to be the only
entree to this profession. Ambitious, articulate, dedicated, diplo-
Trainee flavorists may originate from matic, energetic, enthusiastic, flexible, help-
many sources: direct from school or college; ful, honest, humble, intelligent, imaginative,
post-university graduates; by transfer from capable of judgment, particular, patient,
manufacturing, quality control or other a perfectionist, persevering, persuasive,
technical areas; or even quite fortuitously. It resolute, respectable, responsible, of reten-
can be fairly said that in the past, many who tive memory, self-confident, sincere, sys-
became eminent flavorists merely drifted tematic, tactful, tenacious, willing and
into the work. Today, the situation is dif- zealous.
ferent. The major flavor houses are con-
scious of the need for highly trained and
Background
knowledgeable flavorists, and appreciate
that trainees must be chosen carefully and Basic academics (a sound knowledge of
trained systematically to satisfy the future chemistry, physics and mathematics is
needs of the industry. Although specific regarded as essential) and experience
pretesting of the abilities of potential (related or nonrelated).
candidates may not be indicative of their
future capabilities, an interview is essential
Specifics
to establish the candidates' key attributes.
Some of these attributes may be natural 1. An artistic flare for this type of work
to the individual, others acquired, and with a lively imagination and possibly
almost all capable of improvement by some obvious creative inclination.
patient training. Views will doubtless differ 2. A willingness to learn and apply
as to the relative importance of any par- knowledge.
ticular character feature in making a selec- 3. Sensitivity to sensory stimuli (the
tion, but certainly age and sex are of small accepted norm is generally adequate as a
consequence. The judgment should be start).
based on the following: 4. An ability to memorize odors (this can
 The Flavorist 693

easily be tested during the course of the Sweet-sucrose 2% in water

interview). Sour-citric acid 0.07% in water
5. An ordered approach and an obvious Salt-sodium chloride 0.2% in water
tidiness in personal presentation. Bitter-caffeine 0.07% in water
6. An ability to mix and communicate with
others (not least in writing). The successful candidate will have no dif-
7. An insatiable curiosity about food and ficulty in giving the correct answers.
flavors.
Ranking Test
There are probably other aspects of The candidate is presented with the follow-
trainee attitudes and aptitude for flavor ing four test solutions set out at random,
work (e.g., medical history, particularly and is asked to place them in increasing
freedom from respiratory disorders or order of sweetness.
known allergies), but adequate overall rat-
ing on the above attributes would certainly A. Sucrose 7.5% in water
imply an excellent potential flavorist, mak- B. Sucrose 10% in water
ing subsequent training and creative work C. Sucrose 12.5% in water
fulfilling to the individual and rewarding to D. Sucrose 15% in water
the company at the end of the long training The successful candidate should have no
period. DiGenova (1974) summarized the difficulty in achieving the correct ranking.
basic attitudes of the trainee flavorist as a
desire to know, a curiosity to discover, Description/Identification of Odorants Tests
an ambition to simulate and, at times, the The candidate is presented with a selec-
effrontery to improve on nature, all coupled tion of no more than five of the following
with a great deal of intuition and enthusiasm. odorants contained in wide-mouthed,
Although the precise method used to screw-capped bottles. The candidate is
select trainee flavorists may differ, it is asked either to identify the material or to
generally agreed that careful screening and describe it in no more than three or four
appraisal are important if valuable time words. The following flavoring materials are
and effort are not to be wasted. Once the suitable for this test:
candidate has cleared the interview, it is
desirable to carry out some simple tests that Acetic acid 10% Oil of anise
are not dependent upon previous experi- Ammonia 2% Oil of cassia
ence. So much depends on the initial acuity Amyl acetate Oil of clove
of the candidate's sense of smell and taste. Benzaldehyde Oil of eucalyptus
The following tests are designed to deter- Citral Oil of lavender
mine the candidate's ability to: (a) detect Decalactone Oil of lemon
and describe the prime taste sensations, (b) Geraniol Oil of nutmeg
differentiate between various strengths of Menthol Oil of orange
the same taste sensation and (c) describe Methyl salicylate Oil of peppermint
simple observable odor attributes. Vanillin Oil of rosemary

Taste Threshold Test This is a test more of the candidate's ability

The candidate is given 10 ml of potable
water followed by 10 ml of the test solution
and is asked to indicate whether there is any
detectable difference. If so, which of the
four prime taste sensations best describes
the difference. The solutions used are:
to communicate than one of precise memory,
although credit can be given for accurate
recall of known odors.
These tests are informative, but need
not figure too prominently in deciding the
acceptability of a candidate for training.
694 Source Book of Flavors
However, they do impress on the candidate,
right from the start, the essentially practical
nature of the flavorist's work, and gets the
candidate thinking correctly in terms of
personal experience of aromatic effects.
TRAINING FLA VORISTS
The training of flavorists has changed sig-
nificantly over the past decade. In the past,
training was akin to an apprenticeship with a
senior experienced flavorist guiding, teach-
ing and being responsible for the gradual
induction of the trainee into day-to-day
activities over many years. This very per-
sonal "one-on-one" relationship (Shore
1974) has, over the past half-century, pro-
duced excellent results, the knowledge and
expertise of flavor creation being acquired
and patterned on that of the senior flavorist
whose wealth of practical experience was
slowly transferred to the trainee.
The activity within the modern flavor
laboratory is much more complex and
nothing as leisurely as in the past. In addi-
tion, trainee flavorists are now more likely
to have a better scientific background and
some innate urgency to learn the job-
although too facile an approach to learning
the art may be a disadvantage. In smaller
laboratories, individual and somewhat
sporadic training is still commonplace, but
in those of the bigger, often multinational,
flavor houses trainee flavorists are required
to undergo an organized course of instruc-
tion to supplement their bench experience
(Fischetti 1974; Cowley 1973; Shore 1974).
This has the effect of shortening the time for
a trainee to produce effective flavorings; it
increases the trainee's ability to memorize
and associate odors and flavors by a self-
imposed discipline; it gives the trainee the
basic knowledge of food processing and the
use of flavorings in all types of end pro-
ducts; and it encourages him to expand his
knowledge by reading and discussion. The
ultimate result should be a flavorist with a
great deal of self-confidence in his creative
abilities and a need to succeed.
The detailed trammg program to be
followed will depend upon the size and
facilities of the company concerned and the
availability of those capable of doing the
training. The schemes used in two major
flavor manufacturing companies are out-
lined in the papers referred to above, but in
many smaller companies the main burden
for training will fall upon the senior flavor
chemist or, indeed, on the trainee himself.
To assist in this, a syllabus of topics follows
together with a list of available textbooks.
Suggested Syllabus for Trainee Flavorists
Theory
The trainee flavorist should have a sound
working knowledge in many areas. This
knowledge may be acquired in formal
educational programs or through company
directed programs. The following knowl-
edge is considered essential for success:
Introduction
The importance of flavor in consumable
products; the relationship of smell, taste
and flavor; hedonic responses to flavor-
preference; the flavor and fragrance indus-
try; communications-the language of
flavor; laboratory rules and routine-safety,
cleanliness, order, accuracy, fire precau-
tions, hygiene, etc.
The Sense of Smell
The nose and sensory receptors; olfactory
impulses; sensitivity; fatigue; adaptation;
factors affecting smell perception; nature
of odorous chemicals; theories on the
mechanism of smell; odor classification; the
technique of odor evaluation.
The Sense of Taste
The tongue and taste buds; prime taste
sensations-sweet, salt, sour, bitter; sup-
plementary taste sensations-metallic,
alkaline, pungency; factors affecting taste
perception; interrelationships of taste sti-
muli; thresholds; the technique of tasting.

Sensory Assessment
Reasons for sensory evaluation; methods of
sensory analysis; individual test techniques
and procedures; test design and significance
of results; taste panels; objective/subjective
correlation of results; collaboration with
researchers; communications and transfer
of sensory data; vocabulary; reference
standards.
Natural Sources of Flavor
Flavor in foods; basic flavor chemistry of
main flavor types; flavor research methods-
chromatography, spectroscopy; relation-
ship of chemical structure and odor/flavor
character; effects of processing on flavors;
oxidation and off-flavors; atypical flavors;
contamination.
Flavorings
Basic types; outline of components; liquid
flavors-solvents; dry flavors-carriers, en-
capsulants; emulsions-emulsifying agents,
stabilizers; flavor potentiators and en-
hancers; relevance to food manufacturer;
stability.
Flavoring Raw Materials
Natural materials as sources of flavor;
extraction-essences, extracts, oleoresins;
distillation-essential oils, concentrated oils,
terpeneless oils, isolates; dehydration-
vegetable and fruit products; expression-
fruit juices, concentrates, pulps; problems
of supply; quality control.
Organic Chemicals
Classification of chemicals permitted for use
in flavorings; basic chemical relationships;
odor and flavor characters of: aldehydes, ke-
tones, esters, alcohols, lactones, terpenoids,
sulfur-containing compounds, nitrogen-
containing compounds; organic reactions
resulting in flavors; quality control of odor-
ous materials.
Flavor Creation
Design of flavorings; natural vs. synthetic
components; strength of constituents; usage
The Flavorist 695
levels; harmony and discord; synergism;
odor and flavor profiles; formulation con-
straints; solvents for specific purposes; in-
teraction of components; maturation; shelf
life and stability; quality control test pro-
cedures; technique of flavor compounding;
ongoing evaluation; communications; ap-
plications; costing; record keeping.
Flavor Legislation
Review of systems currently in force world-
wide; flavor as a food additive; negative,
positive and mixed lists of permitted
flavorants; specific requirements (depending
on area of concern); labeling; toxicology
and testing of safety-in-use; use levels;
flavoring materials; patent protection.
Flavoring Products
Liquid flavors; spray-dried flavors; encap-
sulated flavors; dispersed dry flavors;
emulsions; spice seasonings.
Flavor Applications
The following industries should be studied
from the point of view of flavor application:
meat and fish products-fresh, canned,
frozen; baked goods and flour confection-
ery; sugar and chocolate confectionery;
soft drinks and nonalcoholic beverages;
liqueurs and alcoholic beverages; ice cream;
grocery products-desserts, confections,
sauces, pickles, dry mixes, culinary flavors;
snack products-chips, extrusions; dairy
products-cheese, yogurt, butter; pharma-
ceuticals-medicines, tablets, oral products,
toothpaste; tobacco.
Food Colors
Range of colors available; legislation;
applications; natural colors; stability; color
matching techniques.
Practical Training
The practical training program is aimed at
acquiring a firsthand knowledge of all the
raw materials used in flavorings, the range
of flavorings currently available, test pro-
cedures and stability problems. Only then is
696 Source Book of Flavors
the trainee in any sort of position to carry
out creative composition of flavorings.
Practical aspects of training will depend
upon the facilities available and the working
routine expected of the trainee. In a large
company, there is considerable advantage to
be gained if the trainee spends two to three
years in the flavor/odor quality control area,
and only after that moves to the creative
area (Cowley 1973). During this period,
every opportunity must be taken to evalu-
ate the odor and flavor of the recognized
materials used in flavorings, both natural
and synthetic, making direct comparisons
wherever possible. The program outlined by
Fischetti (1974) sets out the learning pro-
cedure in detail; the method of identifying
odors has also been well described by Engen
(1961).
From the outset of his initial training, the
trainee flavorist is strongly recommended to
start his own library of flavoring materials.
The library may be a set of index cards,
three-ring binder notebook or computer
data base file. Flavor chemicals may be filled
under two main headings, "natural" and
"synthetic," for U.S. products and a third,
"nature identical," for flavors destined for
many other countries. The records may be
kept alphabetically by the most common
name of the material. Each record should
be systematically completed to give: (a)
the common name of the material, (b) any
synonym or the chemical name as appro-
priate, (c) distinguishing number codes
(company, FEMA, Council of Europe,
etc.), (d) regulatory status, (e) a brief odor/
flavor description (as most meaningful
to the trainee), and (f) any usage data,
applications, etc. The record should also
contain any relevant references concerning
the chemical. If a card system is being used,
it may be color coded so that the flavorist
can readily select GRAS, nature-identical,
chemical/odor/flavor types, etc.
Each area of training must be treated as
practically as possible so that the trainee
gains firsthand experience of the odors and
flavors of the raw materials upon which he
can call in recreating a flavor. Flavor work is
practical and books, although essential as a
guide, cannot replace personal experience
of an odor flavor profile. Throughout any
training, be it directed or otherwise, the
trainee must keep detailed records of the
work carried out and establish a system for
the speedy recovery of the data accumulated.
Flavor Library
A well-equipped library is essential to
the training and continued growth of the
trainee. This will permit the trainee to
become familiar with the current knowledge
in the field and stay updated on trends in
technology and the marketplace. The follow-
ing books, journals (trade and scientific),
key societies and some particular articles are
recommended for reading or following on a
regular basis:
General Background
Brennan, J.G., Butters, J.R., Cowell, N.D., and
Lilley, A.E.V. 1990. Food Engineering
Operations, London and New York: Elsevier
Publishing Co.
Considine, D.M. and Considine, G.D. 1989. Van
Nostrand's Scientific Encyclopedia. New
York: Van Nostrand Reinhold.
Earle, R.L. 1983. Unit operations in food pro-
cessing. 2nd Edition. Oxford: Pergamon
Press.
Fellows, P. 1988. Food Processing Technology.
Cambridge: Ellis Horwood.
Hall, C.W., Farra!, A.W., and Rippen, A.L.
1986. Encyclopedia of Food Engineering. 2nd
Edition. Westport: A VI Publications.
Harper, J.C. and Watson, E.L. 1988. Elements
of Food Engineering. 2nd Edition. New York:
Van Nostrand Reinhold.
Pintauro, N.D. 1976. Food Flavoring Processes.
Park Ridge: Noyes Data Corp.
Fennema, O.R. 1985. Food Chemistry. New
York: Marcel Dekker.
Belitz, H.D. and Grosch, W. 1986. Food
Chemistry. Berlin: Springer-Verlag.
Flavor Marketing
Anon. 1989. Flavor growth sparked by changing
food trends. Chern. Mark. Rept. Jan. 2, 4:24,
35.

Anon. 1989a. Flavorings Market Gains Produce
a Merger Frenzy. Chern. Mark. Rept. Nov.
27:5, 23.
Boccone, A.A. 1989. Specialty chemicals: in
pursuit of fast-growth niche markets. Chern.
Week 144(15):32-4.
Chou, M. 1990. Trends in consumer attitudes.
Cereal Foods World. 35(8):758-9.
Stofberg, J. and Stoffelsma, J. 1981. Consump-
tion of flavoring materials as food ingredients
and food additives. Perf. Flav. 5(7):19-35.
Stofberg, J. 1983. Consumption Ratio and Food
Predominance of Flavoring Materials-First
Series. Perf Flav. 8(3):61-4.
Stofberg, J. 1983. Safety Evaluation and Regula-
tion of Flavoring Substances, Perf. Flav.
8(4):53-62.
Stofberg, J. 1984. Consumption Ratio and Food
Predominance of Flavoring Materials-
Second Cumulative Series. 9(4):53-83.
Unger, L. 1989. Strategic factors for business
success in the flavor and fragrance industry.
Perf Flav. 14(6):57-81.
Unger, L. 1989a. Basic business trends in the
worldwide flavor and fragrance industry
1987-1990. Perf Flav. 14(3):42-5.
Flavor Chemistry
Scientific and trade journals
Chemical Marketing Reporter-Schnell Publish-
ing Co., 100 Church St., New York, NY
10007.
Food Chemical News-Louis Rothschild,
Jr., 420 Colorado Bldg., 1341 G St. N.W.
Washington, D.C. 20005.
Food Engineering-Chilton., Box 2035, Radnor,
PA 19089.
Food-Flavourings, Ingredients and Processing
(formerly International Flavours and Food
Additives and The Flavour Industry)-
United Trade Press Ltd., 33/35 Bowling
Green Lane, London, ECI.
Food Technology-1FT, 221 N. LaSalle St.,
Chicago, IL 60601.
IFIS Food Science and Technology Abstracts-
International Food Information Service.
Subscriptions obtained in U.S. through
Institute of Food Technologists.
Journal of Agricultural and Food Chemistry-
American Chemical Society, 1155 16th St.
NW, Washington, D.C. 20036.
Journal of the Association of Official Analytical
Chemists-The Assoc. Off. Anal. Chemists,
The Flavorist 697
Inc., Box 540, Benjamin Franklin Station,
Washington, D.C., 20044.
Journal of Food Science-Institute of Food
Technologists, Suite 2120, 221 N. LaSalle St.,
Chicago, IL 60601.
Journal of the Science of Food and Agriculture-
Office of the Society of Chemical Industry, 14
Belgrave Square, London, S.W.l.
Perfumer and Flavorist-Allured Publishing
Corp., P.O. Box 318, Wheaton, IL 60189.
Riechstoffe-Aromen-Korperpfiegemittle -Gerhard
R. Barsch (ed.), 3 Hannover-Kirchrode,
Postfach 149, Ostfeldstrasse 61.
Commercial Flavor Manufacturer Publications,
Distribution limited, Dragoco Flavor
Report-King Road, Totowa, NJ 07512.
Givaudan Flavorist-100 Delawanna Ave.,
Clifton, NJ 07014. Naarden News, U.S.
Edition-10 Painters Mill Road, Owings
Mills, MD 21117.
Flavor and Fragrance Journal-John Wiley &
Sons, Baffins Lane, Chichester, Sussex,
England, P0191UD.
Cereal Foods World-American Association of
Cereal Chemists, 3340 Pilot Knob Rd., St.
Paul, MN 55121.
Books
Louis Rothchild, Jr., Food Chemical News
Guide, 420 Colorado Bldg., 1341 G St. N.W.
Washington, D.C. 20005.
Guenther, E. The Essential Oils, (6 vol.). D. von
Nostrand Co., New York, NY.
Van Straten, S. Volatile Compounds in Food,
The Netherlands.
Bedoukian, P. Perfumery and Flavor Materials,
Available from Allured Publ., P.O. Box 318,
Wheaton, IL 60189.
Arctander, Steffen 1960. Perfume and Flavor
Materials of Natural Origin. Available from
Maria G. Arctander, 6665 Valley View Blvd.,
Las Vegas, NV 89118.
Arctander, Steffen 1969. Perfume and Flavor
Chemicals, (2 vol.). Available from Maria G.
Arctander, 6665 Valley View Blvd., Las
Vegas, NV 89118.
Food Chemical Codex, Second Edition (with
supplements), National Academy of Sciences,
Washington, D.C. 1972.
National Research Council and Others (1972
et. seq.), GRAS Food Ingredients, A Com-
prehensive Survey of Industry of the Use of
Food Chemicals ... and Scientific Literature
Reviews on GRAS Food Ingredients, NTIS,
698 Source Book of Flavors
Arlington, VA.
Furia' Bellanca 1975. Fenaroli's Handbook of
Flavor Ingredients, 2nd Edition, CRC Press,
Inc., 18901 Cranwood Pkwy., Cleveland, OH
(2 vols).
Heath, H.B. 1975. Flavor Technology: Profiles,
Products, Applications, Westport, Conn.:
A VI Publishing Co.
Charalambous, G. 1978. Flavor of Foods and
Beverages, New York: Academic Press.
Land, D.G. and Nursten, H.E. 1979. Progress in
Flavour Research, London: Applied Science
Publishers.
Mookherjee, B.D. and Mussinan, C.J. 1979.
Progress in the Chemistry of Essential Oils,
Washington, D.C.: American Chemical
Society.
Lawrence, B.M. Essential Oils, 1976-1978 and
Essential Oils, 1979-1980, Allured Publ., Box
318, Wheaton, IL 50189.
Pruthis, J.S. Spices and Condiments: Chemistry
Microbiology, Technology, New York:
Academic Press.
Charalambous, G. 1980. The Analysis and
Control of Less Desirable Flavors in Food and
Beverages, New York: Academic Press.
Heath, H.B. 1981. Source Book of Flavours,
Westport, Conn.: AVI Publishing Co. Inc.
Schreier, P. 1982. Flavour '81, New York: de
Gruyter.
Morton, I.D. and Mcleod, A.J. 1982. Food
Flavours Part A. Introduction, New York:
Elsevier Science Publ. Co.
Charalambous, G. and Inglett, G. 1983. Instru-
mental Analysis of Foods, (Vol. 1 and 2). New
York: Academic Press.
Schreier, P. 1984. Progress in Flavour Research,
Amsterdam: Elsevier Publ.
Schreier, P. 1984. Analysis of Volatiles, Methods
and Applications, New York: de Gruyter.
Merwin, E. 1984. The Development and Applica-
tion of Natural and Artificial Flavor Systems,
Wheaton: Allured Publ. Co.
Flavor and Fragrance Materials-1985, Allured
Publ. P.O. Box 318, Wheaton, IL. 60189.
Bernard, B.K. 1985. Flavor and Fragrance
Materials-1985, Allured Publ. Co.,
Wheaton, IL. 60189.
Farrell, K.T. 1985. Spices, Condiments and
Seasonings, Westport, Conn.: A VI
Publications.
Berger, R.G., Nitz, S., and Schreier, P. 1985.
Topics in Flavor Research, H. Eichorn,
Marzling, Hangenham.
Bauer, K. and Garbe, D. 1985. Common
Fragrance and Flavor Materials, VCH
Verlagsgesellschaft mbH, Weinheim, FRG.
Bills, D.D. and Mussinan, G.J. 1985. Charac-
terization and Measurements of Flavor Com-
pounds. ACS Symposium Series #289,
Washington, D.C.
Heath, H. and Reineccius, G.A. 1986. The
Chemistry and Technology of Food Flavor,
New York: Van Nostrand Reinhold.
Min, D.B. and Smouse, T.H. 1986. Flavor
Chemistry of Fats and Oils, Washington,
D.C.: Amer. Oil Chern. Soc.
Parliment, T.H. and Croteau, R. 1986.
Biogeneration of Aroma. ACS Symposium
Series #317, Washington, D.C.
Birch, G.G. and Lindley, M.G. 1986. Develop-
ments in Food Flavors, New York: Elsevier
Applied Science.
Morton, I.D. and Macleod, A.J. 1986. Food
Flavors Part B. The Flavor of Beverages, New
York: Elsevier Science Publ. Co.
F.E.M.A. 1987. Flavor and Fragrance Materials-
1987. Allured Publ. Co., Wheaton, IL.
60189-0318.
Lawrence, B.M., Mookherjee, B.D., and
Willis, B.J. 1988. Flavors and Fragrances:
A World Perspective. New York: Elsevier
Scientific Publ.
Risch, S.J. and Reineccius, G.A. 1988. Flavor
Encapsulation, Washington, D.C.: American
Chemical Society.
Teranishi, R., Buttery, R.G., and Shahidi, F.
1989. Flavor Chemistry: Trends and Devel-
opments. ACS Symposium Series #388,
Washington, D.C.: American Chemical
Society.
Martens, M., Dalen, G.A., and Russwurm, H.
1989. Flavor Science and Technology. New
York: John Wiley & Sons.
Parliment, T.H., McGorrin, R.J., and Ho, C.T.
1989. Thermal Generation of Aromas. ACS
Symposium Series #409, Washington, D.C.:
American Chemical Society.
Min, D.B. and Smouse, T. 1989. Flavors in
Lipid Foods. Washington, D.C.: American
Oil Chemists Society.
Bessiere, Y. and Thomas, A.F. 1990. Flavour
Science and Technology. New York: John
Wiley & Sons.

Maarse, H. 1991. Volatile Compounds in Foods
and Beverages. New York: Marcel Dekker
Inc.
Food applications Food applications
are generally covered in various trade
journals or books devoted to the particular
product of interest. Since this listing would
be very large, the following will be used for
example only:
Woodroof, J.G. and Phillips, G.F. 1981.
Beverages: Carbonated and Noncarbonated.
Westport, Conn.: A VI Publishing Co.
Minifie, B.W. 1989. Chocolate, Cocoa and
Confectionery. New York: Van Nostrand
Reinhold.
Ockerman, H.W. 1989. Sausage and Processed
Meat Formulations. New York: Van Nostrand
Reinhold.
Holas, J. and Kratochvil, J. 1983. Progress
in Cereal Chemistry and Technology.
Amsterdam: Elsevier Science Publ.
Matz, S.A. 1989. Bakery Technology.
Amsterdam: Elsevier Science Publ.
THE FLAVOR LABORATORIES
Creation
Flavor laboratories available throughout the
flavor industry vary from purpose-designed
facilities, which are generally part of a com-
plex of laboratories equipped with all the
latest instrumentation and applications
capability, to small all-purpose units provid-
ing only the minimum. Although additional
facilities make the work of the flavorist
much easier, they are not vital and a flavorist
can work perfectly satisfactorily in com-
paratively simple surroundings. However,
the following basics should be provided: (a)
a clear run of benching, preferably topped
with some impervious material, such
as Formica, to allow for easy cleaning;
(b) a bank of narrow shelving to carry
sample bottles of raw materials, laid out
systematically and within easy reach of
the flavorist; (c) good cupboard storage
facilities for glassware, samples, bulk
The Flavorist 699
chemicals, etc.; (d) an accurate balance,
preferably of the direct recording type and
fitted with a tare control; (e) good lighting,
preferably not direct sunlight, but if this is
unavoidable, then adequate sun-blinds; (f) a
stainless-steel sink unit with hot and cold
water; (g) a hot plate and/or steam bath;
(h) air conditioning is very desirable and
necessary in some parts of the world (but
units directly fitted into window openings,
etc., may be overly distracting), and (i) a
small area separate from the rest of the
laboratory, fitted with a desk and chair for
the use of the flavorist.
The aim in setting up a flavor laboratory
should be to provide the flavorist with all the
raw materials permitted for use and avail-
able for subsequent production needs, with
sufficient working space to allow for several
projects to proceed concurrently without
the danger of cross-contamination. The
environment should be one of calm; creative
work cannot be carried out effectively in the
midst of turmoil and constant distraction.
Communication with other flavorists and
colleagues from other areas of the company
is to be encouraged, for the flavorist cannot
work in isolation; but uncontrolled dis-
cussions can be very disruptive and may
be counterproductive rather than helpful.
Flavor creation laboratories should be
located, wherever possible, away from the
main stream of traffic to reduce adventitious
disruptions.
Applications
Application work cannot be carried out
effectively in the same laboratory as flavor
creation, and for this a small separate
laboratory/experimental kitchen is neces-
sary. This should be provided with: (a)
a clear run of benching or a good work-
ing table, preferably topped with some
impervious material for easy cleaning; (b) a
refrigerator with an integral deep-freeze
compartment; (c) an electric oven; (d)
microwave oven; (e) coarse and fine scales;
700 Source Book of Flavors
(f) a blender; (g) any pilot-scale machinery
appropriate to the applications envisaged.
In a purpose-designed complex, these
applications laboratories are usually
equipped to reproduce the conditions found
in the appropriate manufacturing depart-
ments. These offer the best opportunity for
ensuring reliable usage data.
Sensory
Odor and flavor evaluation of trial mixes is
an essential feature of flavor creation. All
too frequently, such intermediate flavoring
products are discussed on the open bench in
an atmosphere redolent with extraneous
odors. These may not particularly affect the
resident flavorist, but certainly interfere
with the judgment of anyone entering the
laboratory for the occasion. Wherever
possible, the flavorist should be provided
with a separate facility, convenient to the
laboratory, in which to evaluate his products
and experimental blendings away from the
bench. This room need not be elaborate;
merely a table and chairs in a quiet room is
all that is really necessary. In the applica-
tions laboratories, elaborate facilities
for the sensory evaluation of food products
and flavorings may be provided, and these
certainly offer more ideal conditions for
forming a judgment. Such conditions, how-
ever, are not so essential for flavor creation
and day-to-day assessment of flavoring
compositions.
The provision of gas chromatography and
other instrumental aids is highly desirable in
the modern context, but the flavorist is not
really the right person to use them-he
wishes to use the results only without wast-
ing time on the mechanics of the technique.
With a limited staff, such essential support
facilities may have to be the concern of the
flavorist; but this is not the ideal situa-
tion. In such cases, it may be preferable to
purchase the service from some outside
consulting laboratory; it may not cost any
more in the long term.
TABLE 15-1. Scheme for Rapid Visual Identification
of Flavoring Materials
Spot Color
Code Classification
YELLOW FEMAGRAS
GREEN Nature identical
BLUE Natural
RED with UKFACC List No.5 (accepted for
Figure 5 use)
PALE BLUE In-house speciality chemical
Where materials fall into more than one category the
colored disc is segmented:
FEMA GRAS/Nature identical!
accepted for use in UK (FACC
list No.5)
Obviously, the scheme may be extended to give other
essential data about the status of the flavoring material.
FLAVORING COMPONENTS
The flavorist cannot work without raw
materials and the flavor laboratory must be
stocked with samples of all the basics for
flavor creation and formulation, including
natural and synthetic materials, and adjuncts
such as solvents, carriers, emulsifiers, etc.,
depending on the nature of the end product.
The size of the samples will depend to some
extent on usage and also on cost, but for the
majority a 1-2oz. amber glass bottle with a
ground stopper or a good quality screw cap
is quite adequate. Each bottle should be
clearly labeled with the accepted name of
the chemical (either common or systematic
name, whichever is the more appropriate).
For convenience, the bottle may also be
distinguished by a code of self-adhesive
colored spots, which indicate at a glance the
regulatory status or other characteristics of
the contents. The scheme given in Table
15-1 is from Cowley (1978) and is used
in some of the major flavor manufacturing
companies. This should be coupled with a
systematic arrangement of the chemicals on
the laboratory shelving and is best left to the
discretion of the flavorist.
It is essential that the chemicals in the
flavorist's laboratory be representative
 The Flavorist 701

of those available for manufacturing. the marketplace and create new flavorings
They should be from the same source and whose superiority over existing flavorings
replaced regularly as required, depending must then be demonstrated. The initiative
upon the stability of the chemical or change to create new flavorings, therefore, may
in supplier. Chemicals or essential oils that arise from within the company or as a result
are known to be unstable (such as citrus of external demands.
oils) should be stored in a refrigerator and
routinely replaced with fresh material. One
Target Flavor Profile
does not want to create a flavor and then
find that it cannot be manufactured due to a Whatever the source, it is necessary to
difference in the flavor ingredients between decide exactly what target profile is to be
creation and production. imitated, what material presently available
represents this target and the anticipated
end use of the developed flavoring. The task
LABORATORY GLASSWARE of defining the target flavor is much more
Nowhere is clean, odor-free glassware of difficult than it may appear. Ideally, the
more importance than in the flavor (or food scientist can give the flavorist a food
fragrance) laboratory. The flavorist should product on the market and request a match.
be provided with an adequate supply of This is most common. This provides the
glassware, particularly pipettes and beakers. flavorist with a concrete model for flavor
There should also be facilities for a thorough formulation. If there is no product on
washing and drying of them to obviate any the market as a target, the task becomes
cross-contamination. Preferably, separate much more difficult. For example, the food
washing-up facilities are desirable, but a scientist requesting a strawberry flavor has a
compromise may be necessary. Whatever certain profile in mind. It may be juicy, ripe,
facilities are available, it is essential that all seedy and cooked. All of these attributes
laboratory glassware be clean and free of must be communicated to the flavorist, who
odors from any previous use. It should be then has to match these descriptors to his
common practice that the flavorist smells memories of each of these attributes. Even
the glassware prior to use in order to ensure with the best description, the flavorist will
that no residual odors are present. have a different idea of the flavor than the
food scientist. However, there must be a
THE ROLE OF THE FLA VORIST- starting point for creation and the work
must begin.
FLAVOR CREATION
Prior to beginning work on creation of
With few exceptions, the food and related the flavor, the flavorist must have additional
industries look to the flavor industry, as information. It is essential to know the
a specialist supplier, to provide them with several things about the food product that
flavorings that not only suit the tastes of the the flavor will be used in. The food pro-
consumer, but are also compatible with the duct must be defined in as much detail as
nature of their products and the technology possible. Necessary information would
used in their manufacture. It is one of the include: Will the flavor be used in an alco-
flavorist's main duties to appreciate these holic beverage, a carbonated beverage or a
requirements and, within the known con- still beverage; is the food fat- or aqueous-
straints, provide for these needs by the based; what is the pH; what other ingredients
development of flavorings that will fully are present; what thermal processing will be
satisfy both manufacturer and consumer. involved; does the base have any flavor of its
Alternatively, through research or tech- own; and so on. The best solution here is to
nological advantages, one may be ahead of request a sample of the base to be flavored,
702 Source Book of Flavors
an outline of the anticipated manufacturing
process and information on the final packag-
ing. Flavors interact very significantly with
other food constituents as well as packag-
ing materials, and thus it is essentially
impossible to create a flavor without know-
ing the food for which it is intended (Mills
and Solms 1984; Schmidt and Maier 1989;
Baines, Morris and Edwin 1987).
A final piece of information required
before the flavorist begins work is to know
the limitations in use of flavoring materials.
A major limitation is whether the flavor is to
be labeled artificial or natural. Additional
considerations may include whether the
product is to be stable to oxidation (some
citrus oils would be a problem), clear
or cloudy (beverages), requirements for
physical stability (beverages) etc.
Creation
Flavor creation may be done in either of two
ways: (a) the traditional method of creating
a formula from major known constituents
and then imposing the nuances by associa-
tion involving the use of flavoring materials
of known odor!flavor character, or (b) the
strictly scientific approach using the results
of gas chromatographic analysis and other
instrumental techniques, with the flavoring
derived from the analytical figures obtained.
Neither method is fully satisfactory. The
former depends too much on the subjective
experience of the flavorist, while the other
produces an incomplete profile usually
lacking some aspects of the natural flavor,
due probably to errors in the analytical
process. The best approach is a combination
of both methods, using all the accumulated
scientific data and technological know-how
combined with the artistic interpretation
and creative flare of the flavorist (Powers
and Quinlan 1974).
Flavor Breakdown
The flavorist may chose to break down a
flavor into parts to simplify the task. The
flavor may be broken down as outlined by
Fischetti (1990):
FLAVOR
Flavor Diluent
Differential Contributory Character
Character Impact-Character impact com-
pounds are those, when smelled, that are
clearly reminiscent of the named flavor.
This could be a pure flavor chemical (e.g.,
citral for lemon) or a natural material (e.g.,
fenugreek for maple). A list of flavor impact
compounds is provided in Table 15-2.
Flavor Contributory- These components
help develop the named flavor, but are
not truly the named flavor. They have a
character similar to that of the named
flavor. Examples here might be oil of tagette
for apple, orris root for raspberry and ethyl
butyrate for grape.
Flavor Differential -These components
contribute different unique notes to the
flavor. Pure grape flavor does not exist in
nature, for example, but it is a complex
association of nuances that are ultimately
recognized as grape. One may see some
unusual or unexpected components in this
category-all is fair in flavor creation. One
cannot be limited by what seems right or
traditional, but must be free to use anything
that works.
Some examples of differential com-
pounds are listed below:
Flavor Component
Vanillin Peppermint
Butterscotch Menthol
Strawberry Jasmine
Pineapple Olibanum
Green Cis-3-hexenol
Bitterness Triethyl citrate
Nuttiness Pyrazines
Diluent- The diluent is the flavor solvent
(vegetable oil, alcohol, propylene glycol,
 The Flavorist 703

TABLE 15-2. Selected Character Impact Items TABLE 15-2. Continued

(Fischetti 1989) ------------------
PEPPERMINT Menthol
ALMOND 5-Methylthiophen-2- PINEAPPLE Allyl Caproate
carboxaldehyde Methyl beta
ANISE Anethole Methylthiopropionate
Methyl Chavicol (Estragol) Ethyl Butyrate
APPLE Ethyl2-Methylbutyrate POPCORN Methyl-2-Pyridy!Ketone
IsoAmyl Acetate PRUNE Benzyl4-Heptanone
BANANA Iso Amyl Acetate RASPBERRY Alpha Ionone
BERGAMOT Linalyl Acetate Alpha Irone
BLUEBERRY Isobutyl2-buteneoate P-Hydroxyphenyl-2-Butanone
BLUE CHEESE 2-Heptanone RED CURRANT Trans-2-Hexenol
BUTTER Diacetyl SEAFOOD Pyridine
CARAMEL 2,5 dimethyl-4 Hydroxy Piperidine
3(2H) Furanone TriMethylAmine
CASSIE P-Mentha-8-thiol-3 one SMOKE Guaicol
CELERY 3-Propylidene Phthalide 2,6-Dimethoxyphenol
CHERRY Benzaldehyde SPEARMINT L, Carvone
CHOCOLATE 5-Methyl-2-Hexanal STRAWBERRY Ethyl Methylphenylglycidate
Isoamyl Butyrate Ethyl Maltol
Vanillin TOMATO Isobutyl thiazole
Ethyl Vanillin Cis-4-Heptenal
Methyl Methoxypyrazine WINTERGREEN Methyl Salicylate
CINNAMON Cinnamic Aldehyde VANILLA Vanillin
COCONUT Gamma Nona lactone VINEGAR Ethyl Acetate
Delta-Octalactone Glacial Acetic Acid
COFFEE Furfuryl Mercaptan
Furfuryl Thiopropionate
COGNAC Ethyl Oenanthate
CLOVE Eugenol triethyl citrate, water, triacetin or benzyl
CORIANDER Linalool alcohol). Flavors are seldom 100 percent
CUCUMBER Nona trans-2-cis-6 dienal
GARLIC Diallyl Sulfide
active components, but more likely only 10-
GRAPE Methyl Anthranilate 20 percent. This is because the individual
(Concord) flavor constituents may not be mutually
GRAPEFRUIT Nootkatone soluble. A solvent may therefore be required
GREEN BELL 2 Methoxy-3-isobutylpyrazine to keep the flavor from precipitating or
PEPPER
GREEN Cis-3 Hexenol
undergoing phase separation. The solvent
LEAFY also adds some bulk, which may be desir-
HAZELNUT Methylthiomethylpyrazine able in terms of manufacturing (i.e., a larger
HORSERADISH 1-Pentene-3-one volume to weigh or distribute in a food
JASMINE Benzyl Acetate product).
LEMON Citra!
MELON 2-Methyl-3-tolylpro-
Other flavor chemists may find it useful
pionaldehyde to break down a flavor differently for its
Hydroxcyitronellal dimethyl recreation. Heydanek (1976) provided an
Acetal alternate scheme, which is presented in
2,6 Dimethyl-5-heptenal Table 15.3. He begins with the "primer"
2-Phenylpropionaldehyde
2-Methyl-3-( 4 isopropylphenyl)
(equivalent to the character impact com-
propionaldehyde pound) and then adds a "toner." The
MUSHROOM 1-0cten-3-ol "toner" is closely related to the primer in
MUSTARD Allyl isothiocyanate bringing out its character. Neutral esters are
PEACH Gamma-Undecalactone common to all fruit flavorings and thus are
PEANUT 2,5-dimethylpyrazine
PEAR Ethyldecadienoate (Cis 4,
considered for all the products listed in
Trans 2) Table 15-3. The "traces" are compounds
 ~
Cll
0
=
§
t:x:l
0
0
:oo;-
a
:!1
~
~

TABLE 15-3. Flavor creation approach used by Heydanek (1976)

Base Peach Cherry Raspberry Strawberry Pineapple Grape

Neutral esters Ethyl Acetate Ethyl Acetate Ethyl Acetate Ethyl Acetate Ethyl Acetate Ethyl Acetate
Amyl Acetate Amyl Acetate Amyl Acetate Ethyl Butytrate Amyl Acetate Ethyl Butyrate
Ethyl Butyrate Ethyl Butyrate Amyl lso Valerate Ethyl Iso Valerate Amyl Butyrate
Ethyl Butyrate
Primer C-14 Aldehyde Benzaldehyde Ionone C-16 Aldehyde Allyl Caproate Methyl Anthranilate
Toner Benzaldehyde Tolyl Aldehyde Veltol Vel to I Geranyl Acetate Ethyl Oenanthate
Naturalizers Oil Neroli Oil Bitter Almond Oil Orris Oil Orris Oil Orange Oil Cognac
Oil Cognac Oil Cloves Oil Jasmin Dillseed Oil Oil Spruce Oil Petitgrain
T.F. Peach T.F. Cherry T.F. Raspberry T.F. Strawberry T.F. Pineapple T.F. Grape
Traces Benzyl Acetate Aldehyde C-14 Vanillin Vanillin Vanillin Aldehyde C-14
Geranyl Acetate Vanillin C-16 Aldehyde Diacetyl C-14 Aldehyde Ethyl Salicylate
Cinnamyl Alcohol Orange Oil Iso Eugenol Benzyl Butyrate St. John's Bread Cinnamic Aldi
Ionone Ionone Oil Rose Ethyl Lactate Lime Oil Benzaldehyde
Anethol Oil Neroli Geranyl Acetate Oil Lemon Ylang Yland Oil Oil Lemon
Solvent Ethyl Ethyl Ethyl Ethyl Ethyl Ethyl
Alcohol Alcohol Alcohol Alcohol Alcohol Alcohl
Propylene Propylene Propylene Propylene Propylene Propylene
Glycol Glycol Glycol Glycol Glycol Glycol
Water Water Water Water Water Water

essentially the same as the differential com-
pounds mentioned before. Heydanek (1976)
adds a category he calls the "naturalizers."
These flavor materials are natural oils,
oleoresins or extracts. Their purpose is to
add a natural character to the flavoring
through their complexity.
Each flavorist probably has his own
system to break down the flavor into parts
so the task can be simplified for duplication.
(Perry 1987 divided his creation task into
top, middle and base notes). One system
is likely as good as the next, for they all
permit breaking the task into parts for easier
management.
Selection of Flavor Compounds
Once the flavorist has decided what flavor
notes are needed to reproduce a flavor, the
task becomes one of compound selection.
There are numerous ways of selecting com-
pounds for use.
Publications
If one is going to recreate the flavor of
strawberry, for example, it stands to reason
that the truest strawberry flavor can be
obtained by using the same flavor con-
stituents that nature used in the strawberry
itself. Thus, the flavorist may turn to
the published literature in order to find
what compounds have been identified in
strawberry. This information is most readily
available through the compilation of volatile
compounds found in foods authored by
Maarse and Visscher (1989). This offering
is updated every other year and is very
thorough. Additional information can be
found in other food-related journals such
as the Journal of Agricultural and Food
Chemistry, Journal of Essential Oil Research
and the Perfumer and Flavorist. Symposia
are also a good source of information.
Symposia such as the Weurman Symposium,
ACS-sponsored symposia and the flavor
conferences held in Greece often provide
up-to-date information on flavor com-
pounds found in foods.
The problem with using the literature to
The Flavorist 705
provide a list of potential flavor compounds
for flavor formulation is that the list is too
comprehensive. A typical formulated flavor
should have 10-20 ingredients. The list of
flavor compounds that the literature will
provide may be well over 500. How does
one narrow this list? Legality will narrow
most lists substantially, but only experience
will cut the list to a manageable number.
There is no substitute for experience.
Previous Company Formulations
While it is unreasonable to ignore all the
previous work that has been done on a given
flavor, using old formulations will serve
to keep a company in the same rut. New
formulations and flavors can be achieved
only through uninhibited, unchanneled
creativity. Old formulations stifle that
creativity.
Previous Experience
Virtually all flavorists spend years tasting
flavor materials-logging these materials
into their memories and notebooks for later
retrieval. They daily taste both old and
new chemicals for potential use. The new
chemicals may come from associations such
as Chemical Sources or their own organic
synthesis group. They will watch the patent
literature, GRAS applications and publica-
tions to find new chemicals for use. Each
new chemical will be obtained and evaluated
at various concentrations in tasting media
for potential use in a flavor application. This
experience is then the ultimate determinant
that controls and guides the flavorist's selec-
tion of flavor compounds.
Product or Process Limitations
The flavorist must, within all of these deci-
sions, keep in mind the product, its process-
ing and storage if the flavor is to perform
properly in the end product. All of the selec-
tion criteria discussed so far have been
directed toward making a given flavor, with
no consideration for the choice of natural or
artificial or the food product it is going to
go into. The flavorist must know the legal
706 Source Book of Flavors
status of all the flavor compounds intended
to be used. Additionally, the flavorist
must depend upon a good knowledge of
chemistry, experience and intuition to
determine which flavor constituents are
soluble in a given food base, which are
stable to oxidation, how they will react with
the food and other flavor constituents,
which ones should be used in a dry flavoring
or liquid flavoring, which will withstand
baking or high pHs and on and on. The
formulation of a successful flavoring is not
fortuitious, but depends upon a great deal of
prior knowledge and experience.
Formulation
Of necessity, the creative process is carried
out systematically, the flavor being built up
stepwise. The flavorist will select the flavor
impact compound(s) and adjust its level in
the appropriate tasting medium (customer's
base) to bring the primary note into being.
Then the next flavor note is added. Step by
step each flavor compound is added, with
the flavorist always going back and readjust-
ing the formulation as each new flavor con-
stituent is added. When the flavorist is
satisfied with the new creation, it goes into
the applications laboratory for unbiased
evaluation. Caution and experience must
again be called upon, for flavoring composi-
tions may mature, undergoing slow chemical
change due to esterification, etc., depending
upon the chemicals present. Some time for
this may have to be allowed before a final
decision is made on the acceptability of
the flavoring. If the flavor is acceptable in
the view of the applications laboratory, the
flavoring may be sent out to the customer
for evaluation. If not, it goes back to the
flavorist for another try. The customer
is seldom satisfied with this first flavor
submission. This is due to an inability to
adequately communicate the total concept
of a flavor. The flavorist hopes it is close
enough to the customer's ideal so that a
discussion will take place and the flavor
reformulated to better match the customer's
concept of the desired flavor.
Manufacturing
During this whole sequence the flavorist's
attention will have been concentrated on
attaining the best possible flavor match
within the customer's constraints. Having
achieved this, other considerations must
now be taken into account, not least of
which are practicality to manufacture the
flavoring in bulk and its cost. Bonica (1974)
stressed the following points of major con-
cern to the flavor manufacturing depart-
ment: The flavorist should make sure that
all the ingredients he has used are available
and do not have to be specially made or
have unacceptably long lead times; the use
of existing flavoring compositions should be
strictly limited and formulations "exploded"
wherever possible; if solutions of ingredients
are necessary in the laboratory, these should
be converted to the prime chemicals in the
final formulation; the flavorist should avoid
unnecessary processing steps, all of which
will add to the cost of the finished flavoring;
he should define any critical mixing pro-
cedure or standing times. It is incumbent on
the flavorist, finally, to review the formula-
tion and make sure that every component is
really necessary in the finished flavoring; it
is often found that some components are
present at well below their threshold.
THE ROLE OF THE FLA VORIST-
EFFECTIVE INTERFACES
As in many other industries in this tech-
nological age, the flavor industry (and its
closely associated chemical production and
fragrance industries) has a clearly defined
technical sector embracing research, pro-
duct development, manufacture and quality
assurance within the company, and a tech-
nical service externally to assist its customers
in product applications. This division of
technical effort calls for staff having differ-
ent qualifications, experience and aptitudes,
yet all are capable of working together
toward a common goal, which is profitable
to the company. This implies close working
relationships at all levels. The flavorist, as

an integral part of the team, must perfect
the interfaces with all those who influence
his activities.
The Research Department
The research department generally calls
for a graduate staff assembled from many
disciplines dictated by the complexity and
nature of the research projects in hand and
the amount of money budgeted for this. In
those companies or organizations equipped
with modern instrumental techniques in
odor and flavor research, the graduate staff
invariably acquires considerable expertise in
handling complex electronic equipment, but
rarely has any experience in the sensory
aspects of their research. For their research
to be effective, the researcher must call
upon the flavorist to assist in the sensory
assessment of isolated components or frac-
tions. This can be done by sniffing gas
chromatographic effluents, or by tasting
collected fractions, etc. The flavorist, on his
part, must contribute to the dialogue by
telling the researcher the most interesting
aspects of the chromatogram from an odor
or flavor point of view, those aspects hav-
ing a characteristic key or marker nuance
present in the original flavor and presently
impossible to imitate, or those aspects
where the nose is more sensitive than the
instrument calling for a rerun under dif-
ferent operating conditions. The result
of this dialogue will be the subject of the
fraction of most interest to further examina-
tion, probably by mass spectroscopy, with
the aim of identifying as yet unidentified
constituents having a particular nuance
required in the recreation of the natural
flavor profile (Broderick 1972).
The isolation, characterization and
identification of natural odor and flavor
components is only one aspect of flavor
research. Before this information is of any
commercial value a means must be found
of synthesizing the identified chemical( s).
Here, the flavorist is called upon to confirm
what chemicals are most likely to be of value
The Flavorist 707
to him and will, of course, be expected to
evaluate the products as they are received
from the synthetic chemicals laboratory.
At this time, the flavorist is likely to dis-
cuss with the organic chemist any possible
homologues or associated chemicals that
might possess unusual sensory properties
and again assist in their evaluation.
With Other Flavorists
As an individual, it is extremely difficult
for the flavorist's judgment to be entirely
free of bias, particularly in his own field
of expertise. It is for these reasons that
the flavorist must ultimately submit his
created flavoring for the opinion of other
flavorists. This is usually done with a small
expert panel that will assess the product as
objectively possible. The flavorist is re-
quired to enter fully into the discussion,
whose result may lead to some minor changes
being made in the formulation. It must be
remembered, however, that the flavoring
is still the brain-child of experts whose
opinions on a particular odor or flavor
profile may not represent those of the
population as a whole. At this stage, the
organoleptic judgment is one of "difference"
and not one of "preference" and the aim is
to create an imitation flavoring as close to
that of the target flavor as possible. Whether
this is the right flavor for a particular ap-
plication is not in question; that will come
later in the chain of evaluations.
With the Application Technologists
Few flavorings are suitable for use across the
whole spectrum of food, beverages, candy,
cookies, etc., as the processing conditions
are very different, often resulting in flavor
loss or change. It is the responsibility of the
flavor industry to provide flavorings in a
form compatible with the technology of
the end product, which will withstand any
processing conditions and remain stable and
fully acceptable up to the time of consump-
708 Source Book of Flavors
tion. This necessitates the flavor industry
having facilities to reproduce these condi-
tions on a laboratory or pilot scale, so that
any flavoring may be tested and evaluated
under conditions parallel to those used by
the manufacturer. The major flavor houses
have such facilities covering all their many
outlets, and smaller flavor manufacturers
recognize this necessity even if their capa-
bility is limited.
The flavorist is required to have a basic
knowledge of food technology insofar as it
affects the use of flavoring. The flavor tech-
nologists are often qualified food tech-
nologists and may be specialists in some
branch of the food industry, depending on
the size and complexity of the company
employing them. It is the applications
department that carries on the process of
development, carries out pilot scale produc-
tion of the end-product and determines
experimentally the optimum usage rate of
the flavoring. Success at this stage depends
on a good dialogue between the flavorist
and the technologist, and an understanding
of each other's problems. The flavorist must
accept that his flavoring may not be entirely
satisfactory and will then undertake to
modify it until acceptable under the given
processing conditions.
Evaluation at this stage is usually done
by small panels of trained assessors and
although preference may be called for, this
is usually limited to judgments on flavor-
ing levels rather than in absolute terms of
the product itself. The problems of flavor
in food product development have been
reviewed by Katz (1970).
With the Purchasing Agent
A good flavorist keeps abreast on market
intelligence and is generally fully aware of
any new flavoring materials that become
available. In this, he may be ahead of his
company's purchasing department, which
usually copes with the whole range of
raw materials, packages, etc., required in
the course of its business. A good rapport
between the flavorist and the purchasing
agent (buyer) is essential. In some com-
panies, the buyer imposes a barrier between
supplier and the technical departments; they
may have their good reasons, but often
it is the company which suffers by this
restriction. Wherever possible the flavorist
(without commitment to their purchase)
should be able to discuss new products with
the supplier, obtaining as much informa-
tion, technical data, etc., as possible to
enable assessment of their potential value in
flavoring compositions. In doing this, it is
necessary that the purchasing department
be kept fully informed. Such foreknowledge
of the flavorist's needs, the result of sample
testing, etc., is necessary in the event the
material is found suitable for production.
Clark (1972) reviewed the procedure in
a large food manufacturing company, but
similar considerations apply in a flavor
manufacturer's organization.
If the flavorist requires a particular raw
material, be it natural or synthetic, he must
advise the purchasing department of the
grade or quality to be obtained, wherever
possible providing a meaningful specifica-
tion against which the incoming material
will be evaluated. Having received the
product, the flavorist should keep the buyer
informed of his findings and any comments
on quality, etc. This is all part of the effec-
tive interface between the development and
purchasing functions in any company, and
is necessary for the evaluation of both
established and new flavoring materials. In
the case of new products, such data should
be recorded so that, in the event of accep-
tance for use in manufacturing, material of
the same quality can be purchased.
With the Quality Controller
Creating a successful flavor is not the end of
the process for the flavorist. The formula-
tion must be passed on to the manufacturing
department (the complexity of this process
 The Flavorist 709

is determined by the organizational com- The Role of the Flavorist-Technical Service

plexity of the company). The flavorist still
Most flavor manufacturers have long
has the responsibility for the acceptance of
realized that the sale of their products
the production batch and in this must work
demands a special expertise and direct con-
very closely with the company's established
tacts with the user on both the commercial
quality controller. He will have provided a
and technical level. The flavor salesperson
type sample to act as the standard, and
must possess considerable product knowl-
should have a specification against which the
edge and certainly more than a passing
bulk product will be assessed. As a precau-
appreciation of the activities of the end-user
tion, the first bulk product should be sub-
industries. This is certainly essential to
jected to an in-use test and submitted for
create and cement good customer/supplier
panel evaluation to ensure that no un-
relationships, acquire reliable market
acceptable differences have occurred during
intelligence and satisfy the customers'
the scaling-up process.
established needs. There are, however,
occasions when that knowledge and sales
expertise are insufficient to answer a cus-
With Marketing Department
tomer's technical questions. The sales-
person can, of course, relay them to the
It is of no benefit to create the most perfect
laboratory and obtain the answers, but
new flavoring if, for whatever reason, it
on technical matters it is all too easy to
cannot be sold. The marketing department
misinterpret the information. It is better on
of any company is always looking for new
such occasions for the salesperson to be
products to sell to satisfy some known
supported by someone with the correct
or supposed demand. The attitudes that
technical knowledge and background. In
govern new product development are
this respect, both the flavorist and flavor
generally those dictated by company policy
(food) technologist are well-equipped to
and vary considerably, depending on the
provide this technical assistance. Many
nature of the company's products. The
flavor companies now form salesman/
flavor industry is a service industry for food
technologist teams to establish a dialogue
and related manufacturers and although
with a similar buyer/technologist team from
novelty is important, it is not paramount. Of
the customer's organization. This works
greater concern is cost effectiveness linked
well and offers the best chance of success in
with technological advantage and sensory
product development programs.
appeal.
Three main approaches are involved:
For internally initiated flavor projects,
where technological excellence is being a. The presentation of flavorings to
aimed for, price may not be of real con- potential customers. This can be done
sequence to the flavorist. But, for most by the salesperson, but the support
products developed in response to customer of the flavorist, who can conduct a
needs, price is almost always a constraint. technological discussion on their use
This may conflict with the flavorist's prin- and advantages, etc., creates a much
ciples, but there are many occasions when more positive impact, particularly if
commercial reality forces a compromise. the flavorings are offered in the form
This is usually accepted by the flavorist of finished end products.
with good grace, in the realization that his b. The acquisition of technical data on
flavoring must be commercially viable to customers' flavoring needs for new
stand any chance of acceptance in the product development or revitaliza-
marketplace. tion programs. This demands a
710 Source Book of Flavors
reasonably accurate assessment by the
salesperson/technologist team of the
estimated potential of the project
in terms of flavor sales. Modern
laboratory work is very expensive
and, with limited resources available
and subject to budgetary control, the
acceptance or rejection of a major
project has to be based on its antici-
pated commercial viability. The type
of questions that must be answered to
establish this are given below; a clear
and objective description of the pro-
duct concept is of prime importance.
Technical service/project evaluation for
new product development should cover the
following:
1. Is the new product: (a) entirely new
(i.e., nothing similar already on the
market); (b) new to the customer (i.e.,
similar product(s) already on the
market); (c) new as an extension of an
existing line; (d) new as an improvement
of an existing product?
2. Is the inquirer: (a) initiating the change;
(b) considering the change because it has
been suggested; (c) quite clear of his own
objectives?
Note: It is necessary to establish whether
the customer is trying to launch
something quite new, making a dis-
tinctive version of an already existing
product, trying to imitate a brand
leader, improving on an existing line
or product, or just trying to cut
costs. The answers to these questions
may influence the degree of creative
effort called for and give some
guidance as to the target.
3. When it comes to samples, is the inquirer:
(a) already exammmg competitor's
samples; (b) only now requesting
samples; (c) only likely to examine
samples if they are: (1) an exact match
for his existing flavoring; (2) a close
match in very short time; (3) a reason-
ably near standard flavoring, but sig-
nificantly cheaper than his existing
flavoring; (4) supported by end products
ready for evaluation?
Note: The exact matching of customer
samples is often very time-consuming
and frequently not commercially
viable unless the volume of business
available is significant. If there
is a cost ceiling, this should be
ascertained.
4. How is the product to be packaged and
marketed?
Note: This question is aimed at establishing
how the product will be handled
between manufacture and the point
of sale (i.e., is the product fresh,
frozen, dehydrated or canned, etc.)
so that the flavorist has a measure of
the flavoring stability called for.
5. Are there any unusual ingredients used
in its formulation?
Note: Full information on the formulation
is obviously the best answer, but
usually this is withheld for security
reasons. However, if the flavoring is
to be tested in an end product, this
must be done by the customer or
accepted as the result of testing
in another related but not identical
base. An alternative is the provision
of a quantity of unflavored base, but
this may not give the same results as
when the flavor is added at an earlier
stage in its preparation.
6. In what country(ies) is the product to be
marketed?
Note: It is particularly important to obtain
an answer to this question, as legisla-
tive restrictions at the point of sale
may affect flavoring composition and
labeling.
Once it is established that the customer
inquiry is worth the allocation of laboratory

time, then the specific technical details
of the project must be established. The
questions will differ, depending on the
industry, the product and its method of
manufacture. Successful flavor development
depends on the evaluation of the flavoring
under conditions similar to those used by
the manufacturer. The following technical
service/product evaluation process param-
eters should be established:
1. Is the manufacturing process for new
product: (a) already well established; (b)
an entirely new technology or concept?
2. Does the production plant already exist
or must it be built?
3. What are the precise processing con-
ditions as they affect: (1) time and
temperature, (2) mixing method and
sequence, (3) pH, (4) pressure (both
negative and positive), (5) flavor addi-
tion, (6) packaging type, (7) storage
conditions.
4. What is the anticipated throughput of
the plant?
The salesperson, as part of the team,
must also establish certain marketing
information as this will, to some extent,
determine the priority and degree of
urgency for the project.
c. The establishment of a direct tech-
nical relationship between supplier
and customer. This mutual confid-
ence in each other's technological
capabilities is a most desirable fea-
ture of relationships within both the
flavor/food and fragrance/cosmetic
industries, where the problems are
very similar. Acceptance of a high
level of confidentiality is essential
throughout such contacts. It is appre-
ciated that this is not always possible
to achieve for fear that secrets may,
perhaps inadvertently, be made avail-
able to competitors; but within broad
limits these technical contacts have
proved of considerable mutual
benefit.
The Flavorist 711
THE ROLE OF THE FLAVORIST-
SAMPLES
Technical service work almost invariably
involves the acquisition, preparation or dis-
tribution of samples among the various
technical groups concerned. This is a most
important aspect of technical service, as it is
the means by which a company's products
are placed in the hands of the customer's
development team. For success, four cri-
teria are of prime importance in handling
samples:
a. The sample must be provided with a
minimum of delay.
b. The sample size must be adequate for
the customer to produce a representa-
tive sample of his own end product.
c. The sample characteristics must
comply as nearly as possible with the
stated requirements of the project in
both sensory profile and technological
performance.
d. The sample must be within any stated
purchase price range.
Failure on any of the above points may
seriously jeopardize the success of even the
best flavoring. Of these, condition (a) is the
most critical and most responsible for lack
of success.
The flavorist has much to offer and
possibly much to learn from this direct
involvement with the sales function and its
customer contacts. The success of technical
service as a direct support of marketing is
not doubted, but it is expensive and has to
be accounted for. Lack of information as
well as ill-defined or vague requests for
laboratory and technical services are a
cause of much wasted effort and time. An
imprecise mandate can often mean that
costly investigational and development
work stands little chance of commercial
reward. It is the flavorist/technologist who
must ensure that the data provided is com-
plete and accurate in all respects.
712 Source Book of Flavors
References
Baines, Z., Morris, V., and Edwin, R. 1987.
Flavor/Taste perception in thickened systems:
The effect of guar gum above and below.
Food Hydroco/loids. 1(3):197.
Bonica, T.J. 1974. The flavorist as a processor.
Flavour Ind. 5:172-173.
Broderick, J .J. 1972. The flavorist. Food Techno/.
26(11):37.
Clark, K.J. 1972. Selection and evaluation of
flavourings for foods. Preprints of papers pre-
sented at IFST/BSF symposium, Birmingham,
UK, April 20, 1972.
Cowley, E. 1973. The training of a flavourist.
Flavour Ind. 4:18-20.
Cowley, E. 1978. Private communication. Bush
Boake Allen, Blackhorse Lane, London, E17
5QP, England.
DiGenova, J. 1974. The flavourist as an artist.
Flavour Ind. 5:174-175.
Downer, A.W.E. 1974. Social responsibility and
the creative flavourist or bureaucracy versus
the flavourist. (Littlejohn Memorial Lecture,
London.) Flavour Ind. 5:71-76.
Engen, T. 1961. Identification of odors. Am.
Perfum. 76(6):43-47.
Fischetti, F. 1990. Workshop in Food Flavor:
Basic Flavor Systems. Offered at The
University of Minnesota, Department of Food
Science & Nutrition, St. Paul, Minnesota.
May 1-3, 1990.
Fischetti, F. 1974. The training of a flavour
chemist-an organized programme. Flavour
Ind. 5:166-168.
Heath, H.B. 1981. Source Book of Flavor.
Westport, Conn. AVI Publishing Company.
Heydanek, M. 1976. Personal Communication.
Quaker Oats Company. John Stuart Research
Center, 617 West Main St., Barrington, IL
60010.
Katz, M.H. 1970. Flavor problems in food devel-
opment. Food Prod. Dev. 4(0ct.):58-66.
Maarse, H. and Visscher, C.A. 1989. Volatile
Compounds in Foods, Vol. 1-3. Netherlands:
Grafische Industrie.
Mills, O.E. and Solms, J. 1984. Interaction of
selected flavor compounds with whey pro-
teins. Lebensm. Wiss, Techno/. 17(6):
331-335.
Perry, P. 1987. Workshop in Food Flavor:
Creation and Manufacture. Offered at The
University of Minnesota, Department of Food
Science & Nutrition, St. Paul, Minnesota.
September 15-17, 1987.
Perry, P. 1974. The flavourist as a technical man.
Flavour Ind. 5:171.
Powers, J.J. and Quinlan, M.C. 1974. Refining
of methods for subjective-objective evalua-
tion of flavor. J. Agric. Food Chern. 22:
744-749.
Schmidt, E. and Maier, H.G.1989. Thermostable
binding of vanillin to starch. Git. Suppl. 2:
40-42.
Shore, H. 1974. The training of a flavourist-one
on one. Flavour Ind. 5:165-168.
Vock, M.H. 1974. The flavourist using the
achievements of the organic chemist. Flavour
Ind. 5:243-246.
Wesley, F. 1974. Flavour chemist uses salesman-
ship. Flavour Ind. 5:275-276.
Wiener, C. 1974. The flavourist as a biochemist.
Flavour Ind. 5:237-242.
Chapter 16
Quality Control in
the Flavor Industry
Flavor houses are in the position of having
to provide a consistent, high-quality pro-
duct to their customers. The quality control
group plays an important role in assuring
that this commitment is achieved.
Quality control in the flavor industry
refers to two main areas: sensory, which
deals with organoleptic evaluation, and
analytical, which deals with the testing of
physical and chemical properties. These
two functions may be located in the same
laboratory or may be two entirely separate
laboratories. Both sensory and analytical
quality control testing are done on all raw
materials before they are used to make a
flavor, and on all finished flavors before they
go to the customer.
SENSORY ANALYSIS
Finished Flavors
Finished flavor samples come to the sensory
laboratory directly from the compounder in
production. The analyst will be informed
about the amount of flavor produced, date
of production, compounder's name and
customer's name. This information allows
the sensory person to pull up the record on
that flavor. The record generally lists all of
the customers buying that flavor and when
the flavor was last sent to them. A retention
sample is always kept from the last two or
three batches of production to serve as a
standard(s) for comparison with the new
production batch. Retention samples are
typically kept in cool places (encapsulated
flavors) or in refrigerated storage in amber
bottles completely filled to minimize chem-
ical changes during storage. When a new lot
is produced and accepted by the quality
control laboratory, the oldest retention
sample is discarded and replaced by this
sample.
Tasting Media
The newest retention sample and the new
production batch are set up in a side-by-side
sensory comparison or in a triangle test in
order to evaluate color, odor and flavor.
Most commonly, one of three different tast-
ing mediums are used for flavor evaluation.
They are: 1) water, 2) sugar syrup/water
solution, or 3) sugar syrup/citric acid/water
solution. Water is used for tasting flavors
such as: meat, onion, garlic, butter, coffee
and most spicing compounds. The sugar/
water solution is made by mixing 250 ml of
68° Brix sugar syrup with 750ml tap water.
It is used to taste flavors such as: mint,
713
714 Source Book of Flavors
spearmint, peppermint, wintergreen, vanilla
flavors, caramel and banana. The sugar/
acid/water solution is made by mixing
250 ml of 68° Brix sugar syrup, 0.3 ml of a 50
percent solution of citric acid and 750 ml
water. Most of the fruit flavors are tasted in
this sugar-acid solution. The water used in
evaluation must be free of any odor or taste.
Very often, bottled water must be brought
in. Distilled or deionized water produced
inhouse may be of poorer sensory quality
than the tap water.
The reason for using these different
media for evaluation instead of plain water
for all flavors is to put the flavor into a
medium that may be similar to the finished
product it is meant for. For example, sugar
syrup and citric acid simulate the character
of fruits, and a flavor, no matter how good,
would be flat and unnatural in their absence.
Other tasting media may be used depend-
ing upon the flavor and application. For
example, vanilla flavors for dairy applica-
tions may be tasted in milk or cream, and
some meat-like flavors, HVPs or autolyzed
yeasts in a dilute hot saltwater solution (0.2
percent salt). A gravy (white sauce) might
also be used for the evaluation of meat
flavors. An odorless vegetable oil may
be used for oil-soluble butter flavors. A
fondant may be used for the evaluation of
candy flavors such as mint. Thus, it should
be noted that many other evaluation media
may be used in addition to the three most
common media mentioned above.
Levels used for evaluation depend on the
strength of each flavor. There are certain
general guidelines that can be followed.
Natural flavors are generally set up at 0.5
percent -1 percent. This level is obtained by
adding 0.5ml-1ml of flavor to lOOml of
tasting medium. By natural flavors we refer
to fruit juice-based flavors, many cordial
flavors and WONF's. Most artificial flavors
are tasted at 10-SOppm since they typically
are much stronger in flavor. To get 10-
50 ppm, a 1 percent solution is prepared
by adding 0.1 ml of the flavor to 10 ml of
alcohol. Then 0.1-0.5 ml of this solution
is added to 100 ml of the tasting medium.
Natural and WONF spray dries will usually
be set up at about 1 percent in the proper
tasting medium. Artificial spray-dried
flavors will usually be tasted in the range of
50-lOOppm. The 1 percent solution can be
made with water instead of alcohol, since
spray dries are meant to be water soluble.
Slightly higher levels are required for spray
dries than for liquid flavors, because spray
dries are generally 80 percent inert carrier
and only 20 percent actual flavor. It is
very important that one use the same flavor
level for both the standard and the new
sample. A difference of 0.1 ml here could be
interpreted as a difference in flavor strength
during evaluation.
Sensory Analysis
Once the samples are set up at the proper
levels in the proper medium, they are ready
to be evaluated. There is considerable varia-
tion within the industry as to how the sensory
analysis is done. In some companies, one
person will serve to make the sensory judg-
ment as to whether the two samples are the
same or different. If the samples are judged
to be different or are questionable, another
laboratory member will be asked to evaluate
the samples in order to resolve the question.
The sensory person will have had consider-
able experience in the company before
being given this demanding task.
An alternative method of evaluation
is to "panel" the flavors. Paneling may
involve simply setting up a triangle test, for
example, and then walking a tray of samples
through the halls and labs until enough
people have been found to meet the testing
protocol. Testing protocol for a triangle test
may require six people for the test. If two
identify the odd sample, the sample passes;
three is questionable, and four or more is a
fail. The rigor of testing may be dependent
upon the customer and their requirements.
If the customer is financially important, the
flavor may routinely go through a formal
panel evaluation (described in the sensory
chapter of this text). While formal paneling

would be more desirable on a routine basis,
50 or more samples may come through the
quality control laboratory in a given day.
This prohibits the use of formal panels due
to panelist time involved.
Sensory evaluation is concerned with dif-
ferences in color, odor and flavor. When
evaluating a flavor, flavor character and
flavor strength are most important. Certain
color and flavor changes occur normally as
the flavor ages. Fruit juice concentrates and
fruit juice-based flavors are often affected
by non-enzymatic browning. Thus, a newly
produced natural strawberry flavor may be
light red in color and taste fresh, while an
older lot of that same flavor may be turn-
ing brownish-red and have a more pruney
flavor. Citrus flavors become lighter in color
with age due to oxidation. They may also
have a very terpeney flavor. Flavors con-
taining vanillin may turn yellow or pink
with age due to Schiffs base formation. This
is caused by a chemical reaction between the
vanillin and amines in the flavor.
If the retention sample is old, it may have
undergone any of these changes and thus be
different from the new sample. This is not
cause for rejection of the new sample. If,
however, the new sample shows such signs
of color or flavor changes, it may be cause
for concern since this implies the use of old
stock materials.
The criteria for rejection of a flavor is a
difference in color and/or flavor between
the newly produced flavor and the older
stock sample. Flavor character and strength
are most important. Slight color differences
are often tolerated, depending on what the
finished product will be.
Sample Rejection
If a flavor does not pass the sensory evalua-
tion, the first step is to pull the second most
recent retention sample and compare it to
the new flavor and the first retention sample
used to make the original comparison. It is
always possible that the most recent reten-
tion sample was off for some reason. If this
does not seem to be the case, then one must
Quality Control in the Flavor Industry 715
look for problems with the flavor itself.
There are at least four reasons why a
sample differ from the retention sample. All
of them can be traced back to and verified
by the compounder who made the flavor.
The first and easiest reason to deal with is
that the compounder might have sent the
wrong sample or the batch may not have
been adequately mixed before sampling.
One can simply take the sample and paper-
work back to the compounder and ask him
for a re-sample of the batch. The second
cause of a flavor problem may be the use of
old stock materials. If old juice concentrates
or citrus oils have been used, the finished
flavors might exhibit flavor and color changes
characteristic of the browned or oxidized
stock material. Since the compounders keep
very extensive data on each flavor they
make, it is easy to determine the age of the
stock materials used through lot numbers.
When old materials have been used, a color
difference is usually obvious. If the proper
flavor components have been used and the
flavor meets all other specifications, it may
be worked off. The flavor is compounded
again using fresh, new stock materials and
small amounts of the old flavor can be added
to this new flavor without negative effects.
In this way, it does not have to be dumped
out. Work off is generally done at no higher
than 5 percent of the old flavor added to the
new flavor.
A third problem occurs if an incorrect
ratio of aromatics to solvents was used.
This would result in a difference in flavor
strength. For example, if too much alcohol
solvent were added, the flavor would be
weaker than the stock sample. This can be
checked by referring to the compounder's
formulation sheets and can be verified
through analytical results for specific gravity
and refractive index. An excess of alcoh.ol
would make the specific gravity lower than
the specified range. This problem can be
solved by calculating the amount of flavor
materials needed to bring the finished flavor
back to the proper ratio of aromatics to
solvent. The result is a larger batch of
716 Source Book of Flavors
properly proportioned material. Once
again, it is not usually necessary to dump the
material.
The fourth situation that would pre-
sent a bigger problem is one in which a
compounder has used a wrong flavor
component(s). In this case, it is almost
always necessary to reject the material,
throw it away and begin again.
It should be evident by now that the
compounder has a very important role in a
flavor house. Each compounder works on
his own. This minimizes the chances for
mistakes and makes him solely accountable
for the flavor he has made. The accuracy
and thoroughness of his record keeping is
critical. An experienced compounder can
often spot his own mistakes, especially if it is
a case such as using old materials or using
the wrong ratios of materials. The integrity
of these people can often minimize the
effects of an otherwise serious mistake.
Raw Materials
Another function of a quality control lab is
to evaluate and approve raw materials from
a sensory standpoint. Aromatic chemicals,
essential oils, juices, juice concentrates,
etc., would either be manufactured in-
house at a raw materials plant or purchased
from an outside supplier. In either case,
they would go through quality control for
approval before becoming stock material.
The method of evaluation used for raw
materials is very similar to that used for a
finished flavor. The major difference is in
the tasting medium.
Tasting Media
All raw materials are set up for tasting in
plain water. It is important to evaluate the
true character of the raw material without
interference from sweetness or pH. Most
essential oils and aromatic chemicals are set
up at 10ppm. Certain oils such as lovage,
onion and garlic oils and most oleoresins
require lower evaluation levels (e.g., 1-
5 ppm). Stock material off the shelves is
used as the standard for pure chemicals.
Essential oils are generally refrigerated to
maintain freshness. If a fresh sample is not
available in the lab, or if the stock item has
changed due to age, fresher material should
be available stored in full, dark bottles in a
refrigerator. Raw materials are evaluated
by looking for differences in color, flavor
strength and character. Since most of
these are water clear, color becomes less
important.
The purity of raw materials (particularly
synthetic chemicals) is most accurately
checked by gas chromatography and other
analytical methods. Impurities may be more
evident through analytical methods than
through organoleptic methods. However,
sensory still has the final word on approval.
A minor impurity as determined analytically,
could have a very large influence on flavor.
Analytical methods have no taste.
Color Evaluation
Some items are used in flavors primarily to
impart color. Two examples of these are
caramel coloring and special grape extract.
Quality control on these items is a color
check done in a 50ml Nestler tube. The tube
is filled with 50 ml of water to which 0.1 ml
of the caramel color is added and shaken
well. It is compared to a stock sample for
color, intensity and clarity. Special grape
extract is set up the same way, except that
three drops of 50 percent citric acid are
added to the Nestler tube. Special grape
extract is made from grape skins and gets
its color from anthocyanins. Color from
anthocyanins is pH dependent, so a small
amount of citric acid must be added to get
the characteristic reddish-purple color. In a
basic solution, the special grape extract
would appear blue. It is usually used in fruit
flavors which are acidic, or which will go
into a finished product that is acidic.
ANALYTICAL METHODS
While the raw materials and flavors are
undergoing sensory evaluation, certain

analytical tests are also being run. These
tests are a means of checking composition of
raw materials and ensuring that finished
flavors meet specifications. Detailed meth-
odology can be found in ASTA, ASTM,
AOAC, FEMA, USP, Fragrance Materials
Assoc. and the Food Chemicals Codex
publications.
Refractive Index
The two most common tests that are run on
all raw materials and flavors are refractive
index and specific gravity. Refractive index
(RI) can be defined as the degree to which
light is refracted when it strikes a given
substance.
The most common method of measur-
ing refractive index is with an Abbe
Refractometer (lemon and orange oils
AOAC methods 19.079 and 19.082; volatile
oils in spices AOAC method 30.023). This
instrument covers the R.I. range from 1.3-
1. 7 and is accurate to four decimal places. It
can be used for direct reading and requires
only one to two drops of sample. Flavors
are never individual components, but are
mixtures. The refractive index of a flavor is
a function of the refractive index of the
individual components and their propor-
tions. Thus, this method serves as a rapid
and reasonably sensitive means of detecting
compounding errors. Refractive index
values for different compounds can be
found in the Handbook of Chemistry and
Physics and other references.
Specific Gravity
The specific gravity (SG) of a flavor is also a
function of the components and their pro-
portions, since each component has a dif-
ferent specific gravity. Traditionally, specific
gravities have been run by pycnometer.
However, this method is very tedious and
large numbers of samples have caused most
companies to turn to more rapid instru-
mental means, which give a direct digital
readout of specific gravity (e.g., a Paar
Quality Control in the Flavor Industry 717
DMA 45 Calculating Digital Density Meter
by Anton Paar, Warminster, P A.). To deter-
mine density, the sample tube is excited
electromagnetically to vibrate at its natural
frequency. The sample tube is then filled
with sample and the tube is again excited
to vibrate at its new natural frequency.
The differences in frequency between the
tube loaded and empty is related to the
mass difference. Therefore, mass and
subsequently density can be calculated by
the instrument. Some advantages to this
method are that neither sample volume
nor weight has to be measured. Also, the
measurement is independent of sample
viscosity. This instrument is accurate to
three decimal places. By using SG and RI
together, errors in compounding are often
detected, since no two different mixtures
of substances will have exactly the same
combination of RI and SG.
Optical Rotation
Optical rotation is a measurement of
the ability of a substance to rotate plane
polarized light. In order for a substance to
rotate polarized light, it must have a chiral
center in the molecule (i.e., an asymmetric
carbon). While not all molecules have this
property, many do. Similar to the SG and
RI determinations, optical rotation is a
function of composition of a mixture, sensi-
tive both to the constituents and their con-
centrations. Optical rotation adds additional
information not provided by the more
general SG and RI determinations in two
ways. First, not all compounds exhibit
optical rotation and thus the method offers
some specificity in what is being determined
in the mixture. For example, most solvents
used in flavor formulation do not rotate
polarized light and therefore would not be
determined. This removes the major con-
stituent of a flavoring and tends to focus
only on the flavoring constituents of a
flavor. Second, optical rotation is influenced
by the chiral composition of each compound
and the chiral makeup of the flavoring mix-
718 Source Book of Flavors

ture. This has ramifications in the area of done by gas chromatography (AOAC
adulteration. As is discussed in the chapter method 19.001). The flavor may be injected
on adulteration, chemicals synthesized from directly into a gas chromatograph if it con-
petroleum sources (i.e., artificial chemicals), tains less than 20 percent alcohol, or cut
will exist as racemic mixtures: an equal with tetrahydrofuran to dilute the sample
proportion of the chemical that rotates light prior to injection. The alcohol is separated
to the left and right. Thus, there is no net from other flavor constituents using a
rotation of light, whereas chemicals from Chromosorb 102 column and detected using
natural sources (e.g., products of biological a flame ionization detector. The method is
activity) will have a predominance of one rather simple and rapid (10-15 minutes).
chiral form and have a strong net rotation in Alcohol in some flavorings such as vanilla
either direction (Armstrong, Chang and Li may be determined based on density. The
1990). So optical rotation indicates both the vanilla flavoring may be distilled into a
proper formulation in terms of gross com- collection flask and then the density of the
position (checks compounding errors) and distillate determined. From density, the
chiral forms (adulteration). alcohol content of the distillate can be read
Optical rotation is a rapid, simple deter- from a table (AOAC method 19.003).
mination and lends itself to quality control
activities. A polarimeter is used for this
Emulsions
measurement. Optical rotation is commonly
determined on all compounded flavorings, Beverage Emulsions
essential oils and oleo resins (e.g., for citrus The flavor industry produces emulsions
oils, see AOAC method 19.080). The for both flavoring and clouding purposes.
reader is encouraged to consult any good Emulsions are basically unstable systems.
organic chemistry or biochemistry text for Flavors and water do not mix readily and
detail on chiral activity in chemical com- will separate, causing "ringing," which is
pounds and its measurement. very undesirable. While there is little agree-
ment in the literature or within the industry
as to how emulsion quality (stability) should
Alcohol Content
be measured, the ringing test is probably the
Alcohol content is run on flavors that use most commonly used method to evaluate
alcohol as the solvent. When alcohol is the stability of beverage flavor emulsions in
used in any material considered potable, it soft drinks (Tan and Holmes 1988). In this
must be reported to the BATF (Bureau of test, a beverage (2 liters) is made up from
Alcohol, Tobacco and Firearms) for taxa- the flavor or cloud emulsion, and then it
tion purposes. In fact, a flavor company is allowed to stand either upright or on
pays taxes on all incoming alcohol upon its side for one week (room or elevated
receipt and if the company can prove that it temperatures). Visible ringing indicates an
did not produce a potable product with this inadequate emulsion.
alcohol, it can file for an alcohol drawback Alternate methods of evaluating the
(i.e., rebate from the BATF). Most finished stability of beverage flavor emulsions have
flavors are not potable as manufactured been suggested (Tan and Holmes 1988 and
and thus the company can file for drawback, Tse 1990). These alternate methods include
but must explicitly document the use of the centrifugation, turbidity or some measure-
alcohol. Alcohol taxes are very substantial ment of particle size of the emulsion.
and it is very much to the flavor companies' Centrifugation is a very rapid method of
advantage to account for any alcohol and determining if a beverage emulsion will
file for this drawback. separate. Unfortunately, beverage stability
Alcohol in finished flavors is very readily is not always related to stability during
 Quality Control in the Flavor Industry 719

centrifugation (Tse 1990). An emulsion will
destabilize due to one or a combination of
mechanisms. One of those mechanisms is
coalescence, i.e., the coming together
of small flavor droplets to form larger
flavor droplets that destabilize quickly.
Coalescence proceeds with time, and this
factor is not considered in centrifugal
methods of evaluating emulsion stability.
Turbidity is also commonly used to deter-
mine emulsion stability (Tan and Holmes
1988). A turbidity measurement on a diluted
emulsion serves two purposes: an estimate
of overall particle size and an indication of
the "clouding" effect of the emulsion. Very
often an emulsion is used to impart the
appearance of having juice solids in the
beverage, i.e., cloudiness. Thus, emulsion
clouding effect is an important property
of beverage emulsions, which is typically
determined irrespective of an interest in
emulsion stability. Turbidity of a beverage
emulsion is dependent upon the concentra-
tion of emulsion, particle size, refractive
index of the dispersed phase and wavelength
of light used. Since the factors other than
particle size are typically held constant in
this test, we are using turbidity to determine
particle size of the emulsion.
Turbidity is measured using a wavelength
of 400 nanometers or a ratio of absorp-
tion at 800 and 400 nanometers (Kauffman
and Garti 1981, 1984; Rorie, Tanaka and
Akabori 1978). There is a good relationship
between absorption and particle size and
thus emulsion stability (see Fig. 16-1).
An emulsion containing weighing agents
and an acceptable emulsifying constituent
(e.g., gum acacia or modified starch) will
typically not separate if the average particle
size of the emulsion is in the range of 1-3
micrometers. While particle size can be
determined by several techniques (as noted
above), it is generally done by microscope.

1.2
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0 +
1.0
• +
ec
8
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08
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Ill
a: II

~< 06
••

0.4
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02
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00+---~--,-------~------~--~--~--~--~----~
o:o
MEAN PARTICLE SIZE (um)
FIGURE 16-1. Relationship between absorbance and mean particle size of
emulsions. (Tse 1990).
720 Source Book of Flavors
A 0.1 percent-1 percent dilution of the
emulsion in water (or glycerine) is made and
two drops are placed on a glass slide and
covered with a cover slip. A drop of mineral
oil is placed on top of the cover slip. It is
then viewed with the oil immersion objec-
tive. The microscope should be fitted with a
stage micrometer. The size of the particles
being viewed can then be estimated. A
quality control decision at this point becomes
very subjective. It is very difficult to get an
accurate count and estimation of size of an
emulsion by this technique. Theoretically,
several hundred particles should be counted
and sized to get an accurate estimate of size
distribution. Eye fatigue and time do not
permit this, so, in practice, a technician
looks at the emulsion, gives his opinion
of where the particles fall, and accepts or
rejects the emulsion based on that opinion.
This seems to be a rather poor method, but
it is the most commonly used and can work
quite well if the technician is competent.
Alternatively, there are other methods
available to determine particle size of emul-
sions. One such method is by using a Coulter
Multisizer (Coulter Corporation, Hialeah,
Fla.). To use the Coulter Multisizer, the
emulsion is converted to an electrolyte
generally by adding salt at a very low level.
The electrolyte emulsion is then drawn
through a very small glass orifice-one
electrode is outside the orifice, the other
inside the orifice. As a particle passes
through the orifice, the resistance of the
electrolyte channel changes. If there is a
large particle going through the orifice,
there is little electrolyte to conduct elec-
tricity and resistance is high. The converse is
also true. If a small particle goes through
the orifice, there is only a small amount of
resistance. The Coulter Multisizer counts
and sizes a large number of particles in
a very short time, c.a. 20-20,000 in 10
seconds. The instrument will plot and give
the average particle size of the emulsion.
While this method, as well as light scattering
techniques (e.g., Microtrac by Leeds and
Northrup, North Wales, PA.), are much
more accurate than microscopic methods,
costs of the instruments are generally very
significant and prohibit their use.
Spray-Dried Flavors or Dry Cloud Emulsions
Particle size can also be done on spray dries.
Here, one might be interested in emulsion
particle size (i.e., oil droplet size of the
emulsion) and the methodology would be
the same as just discussed. However, one
might alternatively want to know the size
distribution of the spray-dried particles.
Most commonly, the particle size distribu-
tion is done by sieving. The spray-dried
powder is placed in the largest sieve of
a stack and then shaken until the powder
is distributed throughout the sieves. The
powder on each sieve is then collected and
weighed to determine the size distribution
based on the weight of powder collected on
each sieve.
A spray dry flavoring can also be exam-
ined for particle size, using a microscope or
a technique such as the Coulter Multisizer.
For the microscopic method, the spray-
dried flavoring would be mixed with mineral
oil and viewed under low power on the
microscope. If the Coulter method was
used, one would mix the spray dry with
isopropyl alcohol and salt. The mineral oil
(microscopic method) and isopropyl alcohol
(Coulter method) are used here instead of
water so as not to dissolve the spray dry.
Residual Solvents
Residual solvents must be determined on
any flavoring material obtained by solvent
extraction. Oleoresins and absolutes com-
prise the largest group of flavorings in this
category. Table 16-1 presents the legal limits
on residual solvents in oleoresins. Note that
residual solvents are permitted only in the
low ppm levels. Gas chromatography is the
method of choice for residual solvents
(EOA Method No. 1-10-3-1 or AOAC
method 20.215 and 20.216). The oleoresin is
often subjected to an initial distillation step
to isolate the volatiles (including residual

TABLE 16-1. Permitted Levels of Residual Solvents
in Oleoresins•
Methylene chloride residues. Methylene chloride may
be present in food under the following conditions: In
spice oleoresins as a residue from the extraction of
spice, at a level not to exceed 30ppm (0.003% ).
Provided that, if residues of other chlorinated solvents
are also present, the total of all residues of such
solvents shall not exceed 30 ppm.
Ethylene dichloride residues. A tolerance of 30 ppm is
established for ethylene dichloride in spice oleoresins
when present therein as a residue from the extraction of
spice. Provided, however, that if residues of other
chlorinated solvents are also present, the total of all
residues of such solvents shall not exceed 30 ppm.
Trichloroethylene residues. Tolerances are established
for residues of trichlorethylene resulting from its use as
a solvent in the manufacture of foods as follows: Spice
oleoresins ... 30 ppm (0.003% ). Provided that if
residues of other chlorinated solvents are also present,
the total of all residues of such solvents in spice
oleoresins shall not exceed 30ppm (0.003% ).
Acetone residues. A tolerance of 30 ppm is established
for acetone in spice oleoresins when present therein as
a residue from the extraction of spice.
Isoproyl alcohol residues. Tolerances are established
for residues of isopropyl alcohol resulting from its use
as a solvent in the manufacture of spice oleoresins at
50 ppm (0.005%).
Methyl alcohol residues. A tolerance of 50 ppm is
established for methyl alcohol in spice oleoresins when
present therein as a residue from the extraction of
spice.
Hexane residues. A tolerance of 25 ppm is established
for hexane in spice oleo resins when present therein as a
residue from the extraction of spice.
"Code of Federal Regulations (1990).
solvents). This distillate is then analyzed for
residual solvent.
Surface Oil
Surface oil refers to the flavoring oil that is
on the surface of an encapsulated flavoring
material. This surface oil is of particular
interest, since it is exposed to light, oxygen
and package environment and will readily
become oxidized and may produce an off-
flavor in the product.
Quality Control in the Flavor Industry 721
Surface oil is typically determined
only on encapsulated flavorings containing
essential oils. This is because some of the
essential oils (e.g., citrus oils) are extremely
labile to oxidative deterioration. This
analysis is not performed on a routine basis,
but only occasionally to monitor the spray
drying process.
Surface oil is most commonly determined
gravimetrically. This involves placing the
encapsulated flavoring in an Erlenmeyer
flask and adding organic solvent (e.g.,
hexane). The flask would be shaken for
several minutes, the powder filtered from
the solvent and then the solvent removed
by evaporation. The residue, or surface
oil, would be determined by weighing the
residue. Residue may also be quantified
by gas chromatography (Anandaraman and
Reineccius 1986). In this procedure, the
organic solvent would contain an internal
standard. Evaporation of the filtrate would
be stopped at a concentration suitable
for gas chromatographic determination of
the amount of essential oil remaining as a
residue.
Volatile Oil
The volatile oil content of various botanicals
is a measure of flavor strength. It is typically
the volatile components that carry the flavor
of a spice or herb (exceptions being those
materials that have a "bite"). Therefore,
the QC department will run volatile oil con-
tent on many botanicals used as flavoring
materials, or those purchased for further
processing into essential oils or oleoresins.
Volatile oil is also run on some spray-
dried flavorings (Kernik, Reineccius and
Scire 1985; Anandaraman and Reineccius
1986). Spray-dried citrus oils, mint oils,
spice oils, etc., are commonly analyzed for
volatile oil to determine the efficiency of the
encapsulation procedure and amount of
flavoring present in the product.
Volatile oil is generally measured using
a distillation method (AOAC method
30.020-30.027). The Clevenger trap (Fig.
722 Source Book of Flavors
LICHTER THAN WATE R H£AVI£R THAN WAT£R
FIGURE 16-2. Cleavenger trap for the analysis of
volatile oils lighter than water .
16-2) is designed to volumetrically measure
volatile oil content of water insoluble flavor-
ings. Sufficient material is placed in the
sample flask to yield 10-15 ml of volatile oil.
Water and antifoam are added to the sample
flask and then it is heated under reflux for
2-4 hours. The volume of oil present in
the sample can be read directly from the
graduated side arm. It should be noted that
volatile oil is most often reported as ml
oil/100 g dry flavor. This is a volume-to-
weight expression. If the result were ex-
pressed as a weight-to-weight ratio, the
amount of oil (flavor) present in the powder
would be significantly lower, since many
essential oils have a density of about 0.84.
This means of calculating flavor in the
powder also influences the calculation of
drying efficiency or retention. The flavor
emulsion for drying is prepared on a weight-
to-weight basis, but the amount of flavor in
the product is expressed as a volume-to-
weight ratio.
An alternative method for measuring
volatile oil is the Fosslet method (Foss
America, Eden Prarie, Minn.). This method
involves placing the sample (a botanical or
spray-dried powder) into a metal cylindrical
sample holder, which has a sliding hammer
inside it. Perchloroethylene is added and
then the sample holder is placed in the
"vibrating reactor." The vibrating reactor is
similar to a paint shaker and subjects the
sample to vigorous shaking plus the smash-
ing action of this hammer. Extraction is
completed in 1~-2 minutes. The sample
holder is then opened, a desiccant added to
remove any water in the sample and the
perchloroethylene/essential oil mixture
is filtered into an electronic device for
the measurement of specific gravity of the
filtrate. Since perchloroethylene has a very
high specific gravity, specific gravity will be
lowered depending upon the concentration
of essential oil in solution. The instru-
ment may be calibrated to read out the
percentage of extractable oil. This is a very
rapid method (5-10 minutes per test),
which is gaining use in the industry (Kernik,
Reineccius and Scire 1985).
Moisture Content
Moisture content is of concern in dry flavor-
ings (e.g., dry whole spices and encapsulated
flavors). Since most flavoring materials con-
tain volatile components in addition to
water, evaporative methods for moisture
determination are not suitable. Toluene or
xylene codistillation procedures (AOAC
method 30.005) are often the methods
of choice (Anandaraman and Reineccius
1986). The Karl Fischer method (AOAC
method 13.003) also finds substantial use in
the quality control laboratory. This method
is based on the chemical reaction of water
with a pyridine/iodine complex. It has the
advantage of being rapid and reasonably
accurate.
Scoville Heat Units
The Scoville method is an organoleptic
measurement of the pungency (heat or
mouth bite) of certain oleoresins, such as
oleoresin red pepper. A Scoville pungency
of 20,000 means that a sample diluted one
part to 20,000 parts, first in alcohol, then
in sugar water, gives a threshold "bite" to
 Quality Control in the Flavor Industry 723

three out of five people, each tasting 5 ml of TABLE 16-2. Example of EOA Data on a Pure
the final dilution. This is a somewhat subjec- Flavor Compound-Methyl Ionone
tive means of determining the pungency of (EOA 1975)
spices, so a considerable effort has been Sample: Methyl Ionone a and Type EOA
expended toward supplanting it with an Column:
instrumental technique. Initially, a gas Material: Copper Length: lOft. O.D.: 114in. L.D.:
chromatographic method was attempted 3/16in.
Stationary phase: Silicone D.C. 710, 10 percent
(Gruska and Kapral 1977). Later studies Solid support: Chromosorb W, 60-80 mesh, silicone
have utilized HPLC methods since the treated
capsaicins are relatively nonvolatile and Carrier gas: Helium
are much more suited to HPLC techniques Conditions: Column temperature-isothermal: 160°C
(Johnson et al. 1979; van Gernert, Nijssen Inlet temperature: 225°C
Inlet pressure: 35 PSIG Column flow rate: 135 mllmin
and Maarse 1981; Weaver and Awde 1986). Sample size: 1.0
Detector: Type: Thermal conductivity-Hot Wire
Temperature: 275°C
Gas Chromatography Recorder: Span: 1 mV Chart speed: 24in./h
Finished Flavors Chromatogram Fig. 16-3
Gas chromatography ( GC) is not routinely
Relative
used in the analysis of finished flavors. Principal Retention
Refractive index, specific gravity and Components• Time Attenuation
sensory analyses are much faster than GC
1. Ethyl Decanoate 1.00 4
and will detect most problems encountered
2. Jl·Methyllonone 1.89 4
in flavor production. If a problem is found 3. ll Methyllonone 2.07 4
by one of the screening methods, then GC 4. a Methyllonone 2.26 4
would probably be used to determine the 5. JlNormal 4
source of the problem. The only time one Methyllonone 2.41
6. ~ Methyllonone 3.02 4
would run GC on a finished flavor is at a
customer's request. This often causes more Rentention time of last component: 23 min (~-methyl
problems than it solves. The GC profiles of ionone)
two very different-tasting flavors can be very Typical curves: The conditions given here refer
similar or very different. The converse is specifically to the curves attached. Peak 2 is also called
also true; two flavors may have virtually a-isomethyl ionone; peak 3, also called ~-isomethyl
identical GC profiles but be very different ionone; peak 4, also called a normal methyl ionone;
and peak 6, also called ~normal methyl ionone.
in sensory character. GC is a very poor
indicator of the sensory properties of a Method of Calculation: Internal Standard (See EOA
flavor. Thus one may gain very little in- Instrumental Determination 1D-3, Gas
Chromatography, Section 11-D) using ethyl decanoate
formation about whether a flavor tastes the in 30% mixture with sample.
same or different based on the GC profile.
A factor of 1.30 was obtained using the procedure
The problem can come when a flavor com-
described herein.
pany reproduces the taste of a flavor-
ing (nearly exactly), using different raw This analysis may also be accomplished with columns
containing: Silicone DC 550.
materials or simply using materials from a
different supplier. The GC profile of this The Preceding conditions are provided for guidance
only.
new flavor will likely produce quite a dif-
ferent GC profile and the customer will Note: The analyst is cautioned to purify the knowns
regard the flavor as being different when it is used in the determination just prior to use, by
distillation and/or preparative GC followed by GC
not. One must be conscious that it is the analysis for percentage of purity.
sensory flavor that one is concerned about
and not the GC profile.
724 Source Book of Flavors
Flavor Ingredients
Gas chromatography is commonly run on
incoming flavor ingredients. The purpose
may be to determine flavor quality or purity,
or to detect adulteration in the ingredient.
Many flavoring materials are prone to
deterioration during storage. For example,
citrus oils are exceptionally susceptible
to oxidative degradations. Even pure
chemicals may undergo undesirable reac-
tions when stored. Benzaldehyde is readily
oxidized to benzoic acid and limonene both
oxidizes and polymerizes. Therefore, a
GC profile may be used as one method to
determine quality of the ingredient.
Purity may also be monitored by GC
methods. The Essential Oil Association
(EOA) published a compilation of chro-
matographic data on flavor ingredients in
1975 and a later supplement (EOA 1975,
1978). This provided the purchaser with an
FIGURE 16-3. Gas chromatogram of commercial methyl ionone.
idea of purity and the amount of active
components that should be expected in each
flavor ingredient. Examples of data avail-
able in these publications on flavor chemicals
are presented in Table 16-2 and Fig. 16-3.
Most of the GC data in these publications
were obtained using packed column GC.
These data are being replaced gradually by
data on fused silica capillary columns and a
new updated version of these publications is
in preparation by the Fragrance Materials
Association. The first such update was
planned for publication in the summer of
1991. This volume will contain new informa-
tion on 30-40 essential oils and approxi-
mately 100 flavor chemicals.
It may be worthwhile to comment on
the purity of the methyl ionone used as
an example of the EOA data (Fig. 16-2).
Chemicals used as flavoring materials most
often are less "pure" than reagent grade
'
8
5

TABLE 16-3. Physicochemical Tests Applied in the
Quality Control of Flavoring
Materials (Heath 1981)
Natural Plant Materials
Sample may represent whole unground, broken or
previously ground material and should first be judged
on overall appearance and visual quality. In most cases,
whole samples must first be reduced to a uniform,
moderately fine powder before subjecting them to any
of the following tests.
General Tests
Ash: total, acid-insoluble, water-soluble.
Crude fibre.
Extractive matter: alcohol-soluble (in alcohol of
nominated strength), other nominated solvents,
nonvolatile ether extractive. The test may be followed
by an examination of the resulting extract after removal
of the solvent.
Extraneous matter and filth.
Moisture content: oven drying, infrared drying, Karl
Fischer method, xylene co-distillation method.
Volatile oil content: This test may be followed by an
examination of the recovered essential oil by GLC
and/or other test methods.
Tests of Limited Application
Copper-reducing substances.
Starch content: followed by microscopic examination of
the starch grains.
Sieve analysis of particle size distribution (ground
material).
Microscopic examination (for insect parts, etc.).
Undesirable plant parts or other foreign matter.
Limit tests as specified.
Additional Specific Tests
(with specified limits in many countries)
Allspice: quercetannic acid.
Capsicum (cayenne, red pepper): capsaicin content,
Scoville pungency, color content.
Clove: quercetannic acid, clove stems and other foreign
matter.
Curry powder: sodium chloride.
Ginger: gingerine content (or other measure of
pungency), starch, lime (CaO), cold-water extractive,
water-soluble ash.
Marjoram: stems and other foreign matter.
Mustard: allyl isothiocyanate, sodium chloride, starch
and other farinaceous matter.
Paprika: color index, iodine value of fixed oil.
Pepper, black and white: piperine content (Kjeldahl
nitrogen or instrumental method), pepperstarch
content.
Saffron: yellow styles and other foreign matter.
Turmeric: curcumin content (or color index), starch.
Quality Control in the Flavor Industry 725
TABLE 16-3. Continued
---------------------
Vanilla beans: vanillin content, lead number on
alcoholic extract.
Essential Oils
Essential oils are liquids, some of which may crystallize
and solidify on cooling. Such samples should be gently
warmed until completely liquid before carrying out any
tests. Samples should first be evaluated for appearance
(i.e., color, clarity), preferably being compared with a
reserve sample, following by an evaluation of the odor
and the flavor in a diluted sugar syrup.
General Tests
Specific gravity (normally at 25°C/25°C or corrected for
any other temperature) or weight per ml at 20°C.
Refractive index (RI) at 20°C.
Optical rotation (OR) at 20°C.
Solubility in alcohol of a specified dilution.
Tests of Limited Application
Boiling range (0 C).
Melting point (0 C).
Congealing point ("C).
Flash point: open or closed cup ("For oc).
Instrumental Tests
Gas-liquid chromatography (to establish identity/
origin, detect adulteration, determine compositional
changes and for production quality control).
Infrared spectroscopy.
Ultraviolet spectrophotometry.
Specific Tests for Constituents
Acetals.
Acid value.
Alcohols: aceto-formylation method, total alcohols,
tertiary terpene alcohols, citronellol by formylation.
Aldehydes and ketones: bisulfite method, neutral
sulfite method, phenylhydrazine method,
hydroxylamine method.
Chlorinated compounds.
Esters: general, high-boiling solvent method.
Heavy metals.
Phenols: free, total.
Tests Specific for Citrus Oils
Evaporation residue. Peroxide value. Foreign oils.
Specific Tests and Procedures
The special tests applicable to all the major essential
oils are described in the Standards and Specifications
of the Essential Oil Association of U.S.A. and in such
standard texts as Guenther (1948/1952), Pearson
(1976), etc. Where standards are set for essential oils,
it is usual for the test method to be described.
Variations in the test method may lead to different
test results so that the method prescribed should be
adhered to in detail.
TABLE 16-3. Continued
Oleoresins
In physical form, oleoresins range from mobile to
viscous fluids, from semisolids to waxy or sticky pastes.
Samples should be well mixed to ensure uniformity
before testing. Initially, the sample should be evaluated
for appearance (often characteristic), odor and flavor
after dilution in a suitable medium.
General Tests
Volatile oil content, followed by an examination of the
recovered essential oil.
Solvent residues.
Solubility in a specified solvent.
Specific Tests
Capsicum (cayenne, red pepper) oleoresin: capsaicin
content, Scoville pungency index, color index.
Ginger oleoresin: gingerine content (or other pungency
index).
Paprika oleoresin: color index, pungency test.
Pepper (black and white) oleoresin: piperine content.
Turmeric oleoresin: curcumin content (or color index).
Plated or Dispersed Spices
Manufactured flavorings which comprise oleoresins
and/or essential oils plated or spread on an edible
carrier (e.g., salt, dextrose, flour, etc.). If stored in
clear glass, the sample may show surface color fading.
Samples should be well mixed before carrying out tests.
General Tests
Volatile oil content.
Extractives soluble in a nominated solvent.
Carrier base constituents: specific tests as appropriate.
Sieve classification or test for particle size distribution.
Tests of Limited Application
Microbiological examination: total plate count,
freedom from coli forms, salmonella, etc.
Specific Tests
(see oleoresins above)
Synthetic Chemicals
Samples may be liquids or crystalline solids. The nature
of the testing is often determined by the intended end
use. Routine physicochemical tests are necessary for
control of purity, but odor and flavor evaluations are of
more importance when the chemical is intended for use
in a flavoring or fragrance composition.
General Tests-Liquids
Specific gravity (normally at 25°C/25°C or corrected for
any other temperatures) or weight per ml at 20°C.
Refractive index (RI) at 20°C.
Optical rotation (OR) at zooc.
Solubility in alcohol of stated dilution or in other
specified solvent.
TABLE 16-3. Continued
Boiling point/range (0 C) at specified pressure (mm Hg).
Freezing/congealing point CCC).
Flash point (°F or 0 C): open or closed cup method.
General Tests-Solids
Melting point ( 0 C).
Congealing point ( 0 C).
Solubility in specified solvent.
Freedom from insoluble matter.
Specific Tests for Chemical Identity and Purity
Instrumental Methods
Gas-liquid chromatography.
Infrared spectroscopy.
Flavorings
Flavorings may be either liquid, emulsions or dry
powders. Samples should first be evaluated for
appearance (i.e., color, clarity, opalescence, etc.), then
for odor and flavor after dilution in an appropriate
medium. They should preferably be compared directly
with a standard smaple that has been maintained under
optimum conditions and changed at regular intervals.
General Tests-Liquid Flavorings
Specific gravity (normally at 2SOC/2SOC or corrected for
other temperatures) or weight per ml at 20°C.
Alcohol or other specified solvent content.
Refractive index at zooc.
Color intensity or shade (as appropriate).
Flash point (°F or 0 C): open or closed cup method (if
required).
General Tests-Emulsions
Specific gravity (2SOC/25°C) or weight per ml (20°C).
Volatile oil content: steam distillation method.
Microscopic examination of particle size.
Microbiological examination: total plate count, yeasts,
molds.
Ringing test (for beverage emulsions).
Specific tests for stabilizers, antioxidants, etc.
General Tests-Encapsulated Dry Flavorings
Particle size analysis.
Moisture content: xylene co-distillation method.
Volatile oil content: steam distillation method or
organic solvent method.
Microbiological examination: total plate count,
coliforms, salmonella, molds and yeasts.
Vanilla Extract
Natural vanilla extract is subjected to a wide range of
tests to ensure its authenticity. These include:
Specific gravity (25°C/25°C) or weight per ml at 20°C.
Alcohol content.
Glycerin content.
Vanillin content.
Neutral lead number (Wichmann).
Total solids.
TABLE 16-3. Continued TABLE 16-3. Continued

Ash: total, water-soluble, water-insoluble (followed by General Tests

test for alkalinity of ash). Alcohol content.
Acidity (pH). Total solids.
Coloring matter soluble in amyl alcohol. Ash.
Thin-layer chromatographic examination. Fruit and sugar content.
Paper chromatographic examination. Sucrose content.
Pectins.
Microbiological examination: total plate count, molds,
Fruit-based Products
yeasts.
Fruit juices and fruit-based flavorings should be kept
chilled unless the soluble solids content exceeds 65°
Special Texts
Brix; or they should be suitably preserved. Samples
Detection of ~-ionone in fruit extracts.
should be made uniform and should be subjected to
Detection of strawberry aldehyde.
sensory evaluation before applying any of the
physicochemical tests.

TABLE 16-4. Vanilla Extract 4-Fold

DESCRIPTION: A dark brown liquid having a characteristic vanilla bean flavor and
odor, produced in accordance with the Federal Vanilla Standards as published in the
Federal Register Sept. 1, 1962 (pages 8757- 8758) and Sept. 11, 1963 (pages
9982-9983), containing the total sapid and odorous principles of 53.4 ounces of
vanilla beans, Vanilla Planifolia Andrews, per gallon of extract.
PHYSICAL CHARACTERISTICS: METHOD:
Flavor & Odor: Must match standard sample.
Specific Gravity @25°C: 0.9500-0.9700 A.O.A.C. 13th Edition,
9.009-9.011
Refractive Index@ 20°C: 1.3560-1.3760 A.O.A.C. 13th Edition,
28.006-28.007
Alcohol Content (Abs. by Vol.): 35 percent Minimum A.O.A.C. 13th Edition,
9.012
Alcohol Content (Typical Range): 35-39 percent
Lead Number (minimum): 3.8 A.O.A.C. 13th Edition,
19.025-19.028
Lead Number (Typical Range): 3.8-4.2
Vanillin Content (minimum): 0.04 A.O.A.C. 13th Edition,
19.011-19.012
Vanillin Content (Typical Range): 0.04-0.12
Solubilitya:
In Water: Soluble
In Ethyl Alcohol (95 percent): Soluble
In Vegetable Oil: Insoluble
PACKAGING: 1 gallon H.D. polyethylene bottles (4 per case), or
5 gallon H.D. polyethylene pails, or
54 gallon H.D. polyethylene drums (non-returnable)
Storage: Store in tightly sealed containers, at a temperature between 50° and 80°F.
Avoid prolonged exposure to light, heat and air.
NOTE: During storage, especially at low temperatures, this product may precipitate
some of the less soluble plant extractives. This occurs in many products of this type
and normally has no effect on the usability of this product.
SHELF LIFE: Under above storage conditions:
6 months in 1 Gal. H. D. polyethylene bottles
6 months in 5 Gal. H.D. polyethylene pails
9 months in 54 Gal. H.D. polyethylene drums
LABLE DECLARATION:
VANILLA EXTRACT 4-FOLD
• Informational only
728 Source Book of Flavors

TABLE 16-5. Spray Dried Artificial Grape Flavor

DESCRIPTION: An off-white to light yellow powder having a characteristic grape

flavor and odor.
PHYSICAL CHARACfERISTICS: Method:
Flavor & Odor: Must match standard sample.
Moisture: 8% maximum A.O.A.C. 13th Edition, 7.004
Bulk Density (Approx.)": 16.7lbs./cu. ft.
Granulation: 98% thru U.S. #40 minimum 5min.
Rotap
Solubility*:
In Water: Moderate*
In Ethyl Alcohol (95% ): Insoluble
In Vegetable Oil: Insoluble
*Resulting solution will be opaque.
ORGANOLEPTIC TEST PROCEDURE: Triangle taste test: 0.10 gms. in 8 fl. oz.
sweetened water.
PACKAGING: 50 and lOOlb. poly bags in fiber drums, or 50 lb. poly bags in heavy
wall cartons.
STORAGE: Store in tightly sealed containers, at a temperature between 40° and 80°F.
Avoid prolonged exposure to light, heat, air and moisture.
SHELF LIFE: Under above storage conditions: 6 months.
LABEL DECLARATION:
All flavor ingredients contained in this flavor are approved for use in a regulation of the
Food & Drug Administration or are listed as being generally recognized as safe on the
FEMA GRAS list. Product also contains Modified Food Starch and BHA as an
antioxidant.
• Informational only

chemicals used in the laboratory. However,
these materials are produced using methods
that yield food grade quality. "Food grade"
is a statement of safety rather than purity.
Microbiology
Generally, little microbiology is done in-
house in the flavor industry. Most of this
work is contracted out to consulting labs. If
anything is done in-house, it is usually total
plate count, yeasts and molds. This is done
primarily on emulsions and spray dries. It
is not done on other products, since most
flavors do not support microbial growth.
Other microbiological tests may be run by
the consulting lab on a non-routine basis,
such as Lactobacilli, and pathogens such as
Salmonella or Listeria.
Another function of the quality control
lab is to investigate problems that arise with
a flavor both during production and after it
has been sent to the customer. This task
requires a close working relationship with
the research group of the company. Prob-
lems can include concerns about adultera-
tion, color changes or flavor changes.
An overall view of the analyses that are
performed on flavors by the quality control
laboratory is presented in Table 16-3. This
list is quite long and demonstrates the diver-
sity of products that the flavor company
produces and must monitor analytically. A
Quality control laboratory may have more
than 150 defined analytical procedures.
These tests may come from the organiza-
tions listed at the start of this chapter,
be developed in-house or be a customer's
 Quality Control in the Flavor Industry 729

TABLE 16-6. Artificial Wild Cherry Flavor

DESCRIPTION: A colorless liquid having a characteristic cherry flavor and odor.

PHYSICAL CHARACTERISTICS: Method:
Flavor & Odor: Must match standard sample.
Clarity: Clear Visual
Specific Gravity@ 25°C: 0.8130-0.8230 A.O.A.C. 13th Edition,
9.009-9.011
Refractive Index@ 20°C: 1.3630-1.3730 A.O.A.C. 13th Edition,
28.006-28.007
Solubility•:
In Water: Slight
In Ethyl Alcohol (95% ): Soluble
In Vegetable Oil: Insoluble
ORGANOLEPTIC TEST PROCEDURE: Triangle taste test: 0.3 mls in 8 fl. oz.
sweetened water.
PACKAGING: 1 gallon H.D. polyethylene bottles (4 per case), or
5 gallon H.D. polyethylene pails, or
54 gallon H. D. polyethylene drums (non-returnable)
STORAGE: Store in tightly sealed containers, at a temperature between 40° and 80°F.
Avoid prolonged exposure to light, heat and air.
SHELF LIFE: Under above storage conditions:
3 months in 1 Gal. H.D. polyethylene bottles
6 months in 5 Gal. H.D. polyethylene pails
9 months in 54 Gal. H.D. polyethylene drums
LABEL DECLARATION:
All flavor ingredients contained in this flavor are approved for use in a regulation of
the Food & Drug Administration or are listed as being generally recognized as safe on
the FEMA GRAS lists. Product also contains Ethyl Alcohol.
• Informational only

method. Fortunately, only a few are tests
required for any given product and some
tests may be run only rarely. To give the
reader an idea of what types of tests are run
on a flavoring, spec sheets on three different
flavors are provided in Tables 16-4, 16-5 and
16-6.
References
American Society for Testing Material (ASTM),
1916 Race St., Philadelphia, PA 19103.
Analytical Methods Committee. 1984. Applica-
tion of gas-liquid chromatography to the
analysis of essential oils: Part XI. Monographs
for seven essential oils. Analyst 109:1343.
Anandaraman, S. and Reineccius, G.A. 1987.
Analysis of Encapsulated Orange Peel Oil.
Perf Flav. 12(2):33-39.
Armstrong, A.W., Chang, C.-D. and Li, W.Y.
1990. Relevance of Enanthiomeric Separa-
tions in Food and Beverage Analysis. J.
Agric. Food Chern. 38(8):1674-1677.
Association of Official Analytical Chemists
(AOAC), 2200 Wilson Blvd., Suite 400,
Arlington, VA 22201.
BATF (Bureau Alcohol Tobacco and Firearms),
650 Massachusetts Ave. N.W., Washington,
D.C. 20226.
Codex Alimentarius Commission, Via Delle
Terme de Caracalla, I-00100 Rome, Italy.
EOA. 1975. EOA Book of Specifications and
Standards. Supplement 1. Essential Oil
Association of USA, Inc. 900, 17th St. N.W.
Washington, D.C. 20006.
Flavor & Extract Manufacturers Association of
the United States (FEMA), 1620 I St. NW,
Suite 925, Washington, D.C. 20006.
Fragrance Materials Association, 1620 I St.
N.W., Suite 925, Washington, D.C. 20006.
Gernert, L.J. van, Nijssen, L.J., and Maarse, H.
1981. Improvements of the Scoville method
for the pungency determination of black
730 Source Book of Flavors
pepper. In Flavour '81, ed. P. Schreier,
p. 211-216. Berlin: de Gruyter.
Gruska, E. and Kapral, P. 1977. Analysis of
Capsaicinoids from Various Sources by Gas
Chromatography. Sep. Sci. 12:415.
Rorie, K., Tanaka, S., and Akabori, T. 1978.
Determination of emulsion stability by
spectral absorption I: relationship between
surfactant type, concentration, and stability
index. Cosmetics and Toiletries. 93(5):53-62.
Johnson, E.L., Majors, R.E., Werum, L.
and Reiche, P. 1979. The determination of
naturally occurring capsaicins by HPLC. In
Liquid Chromatographic Analysis of Food
and Beverages, ed. G. Charalambous, p. 17.
New York: Academic Press.
Kauffman, V.R. and Garti, N. 1984. Effect of
cloudy agents on the stability and opacity
of cloudy emulsions for soft drinks. J. Food
Tech. 19:255-261.
Kauffman, V.R. and Garti, N. 1981. Spectral
absorption measurements for determination
of ease of formation and stability of oil-in-
water emulsion. J. Dispersion Sci. Tech.
2(4):475-490.
Kernik, K., Reineccius, G.A., and Scire, J.P.
1985. An evaluation of methods for the
analysis of encapsulated flavors. In Progress
in Flavour Research 1984, ed. J. Adda.
Amsterdam: Elsevier.
Tan, C.-T. and Holmes, J.W. 1988. Stability of
Beverage Flavor Emulsions. Perf. Flav.
13(1):23-41.
Tse, K.-Y. 1990. Physical Stability of Flavor
Emulsions. M.S. Thesis, University of
Minnesota, St. Paul, Minn.
United States Pharmacopeia, 12601 Twin Brook
Parkway, Rockville, MD 20852.
Weaver, K.M. and Awde, D.B. 1986. Rapid
High Performance Liquid Chromatographic
Method for the Determination of Very Low
Capsician Levels. J. Chromatogr. 367(2):438.
Chapter 17
Adulteration
INTRODUCTION
Adulteration of a flavoring may be done
either for economic or labeling reasons
(ultimately economic also). In the market
today, natural flavoring materials are in high
demand and a premium price is paid for all
natural flavorings. As a component of a
natural flavoring, it has become exception-
ally profitable to sell synthetic chemicals
as natural compounds. Frey (1988) has
presented a table (Table 17-1) illustrating
how profitable it can be to sell synthetic
chemicals as natural. For example, Frey
(1988) lists neroli as selling for $500/lb. and
the major component, linalool, can be
purchased as a synthetic compound at $3/lb.
Thus, an unscrupulous manufacturer could
purchase linalool at $3/lb. and sell it at
$500/lb. That is a strong incentive for those
who are weak in morals.
The second issue of adulteration is when
it is done in violation of labeling laws. It is
illegal to add a flavor chemical considered
artificial to a food product and not label the
product accordingly. This would be a state-
ment in the ingredient listing if the artificial
constituents do not "simulate, resemble or
reinforce" the named flavor (CFR 101.22)
or a statement on the front of the package
if the artificial component(s) do "simulate,
resemble or reinforce" the named flavor.
There is a strong market demand for all
natural flavorings, and the consumer com-
pany does not want to have "artificial"
appear anywhere on the product label.
Thus, the flavor manufacturer is pressured
to use only "natural" flavor chemicals.
While many "natural" flavor chemicals
are available, many are not. The industry
cannot typically supply as good-quality
natural flavorings as they can artificial.
Therefore, there is an incentive to add
synthetic chemicals to natural flavorings to
boost, round or improve flavor quality and
not label the flavoring as being artificially
flavored. The incentive may be quality-
based to gain a sale if the desired flavor
chemical is not available in the "natural"
form, or simply economics-based if both
flavor compounds (i.e., available as natural
and synthetic) are available, but the syn-
thetic is substantially cheaper.
The issue of adulteration also includes
ethics. The vast majority of flavor com-
panies are ethical by all standards and do
not knowingly adulterate food flavorings.
However, even the most ethical companies
may be involved in adulteration since they
generally do not manufacture every flavor
chemical they use, but buy from many out-
731
732 Source Book of Flavors
TABLE 17-1. Costs and Percentage Composition of Synthetic Compounds and
Essential Oils (Frey 1988)
Oil
Cost
Oil $US/Ib
Neroli 500
Bergamot 20
Neroli 500
Bergamot 20
Cassia 35
Wintergreen 5 80%
side sources. This situation occurred in
the mid-1980's when virtually all of the
oil of bitter almond (natural source of
benzaldehyde) on the market was found
to be synthetic. Many reputable flavor com-
panies were using products they believed to
be natural and yet were not natural.
A reputable company also may get
caught up in adulteration because of dif-
ferent labeling laws throughout the world.
An example is a company that might buy
flavors or raw materials from a European
company. Europe has a nature-identical
status, which permits the use of flavor
chemicals in a flavoring that are synthetic
but found naturally in that food flavoring.
The European company would not have to
label this flavoring (containing synthetic
nature identical components) artificial, but
it must be so labeled in the U.S.
One can readily appreciate the ethical
problems presented with adulteration. The
FDA does not generally make any effort to
police adulteration in the flavor industry.
The FDA has its hands full simply trying to
ensure the safety of our food supply. Thus,
the policing is done largely by the industry
itself. The policing is done for economic
reasons. Most often a flavor company is
given the task of matching a competitor's
flavor within a certain cost. The flavor
company gets the competing flavor and con-
ducts both sensory and analytical testing.
It may arrive at the conclusion that the
flavoring cannot be legally produced either
at the desired cost (competitor is using less
Cost of Synthetic
%Major component Major Component
in Oil $US/Ib
40% linalool 3
17% linalool 3
10% linalyl acetate 3
30% linalyl acetate 3
80% cinnamic aldehyde 3
methyl salicylate 3
expensive synthetic chemicals and calling
the flavor natural) or at the desired quality
(competitor is using non-natural con-
stituents). The flavor company will not go to
the FDA and "blow the whistle," but rather
attempt to work with the customer to point
out the illegality involved and convince
the customer to buy from it instead of the
competitor. This is a hard sell, since the
customer may already have this product on
the market and does not want to change the
flavor or, alternatively, pay a higher price.
Thus, the reputable company is forced to
decide if it should adulterate also or lose
what could be a substantial business profit.
In this chapter, we discuss the analytical
means available to determine if a flavoring
has been adulterated. Adulteration will be
divided into two topics: the addition of
a synthetic compound to a natural flavor
and the addition of less expensive natural
products (i.e., essential oils) to more expen-
sive products. While it is often said that
the best indication of adulteration is "too
good flavor" or "too cheap price," these
indicators are a bit too subjective for most.
ADDITION OF SYNTHETIC
COMPOUNDS TO
A NATURAL FLAVOR
Residual Solvents
A relatively simple approach and often
the first step in detecting adulteration is to
examine the flavoring for flavor solvents

commonly used in artificial flavorings.
Adulteration may be rather unsophisticated
where a company simply buys a good-
quality artificial flavoring from another
flavor company (or its own) and adds the
finished artificial flavor to its "natural"
flavor. The artificial flavor is strong and
well-balanced and, thus, a good choice for
adulteration.
The artificial flavoring typically will
use flavor solvents (e.g., triacetin, triethyl
citrate, propylene glycol or benzyl alcohol)
that do not occur in nature. The identifica-
tion of these solvents in a flavoring is rela-
tively easy. Unfortunately, their presence
does not definitively prove adulteration.
The supplier may claim that the solvents
came from other sources and they did not
add them. Also, ethyl alcohol is a very
common flavor solvent and ethyl alcohol can
be found in natural flavoring as well as
artificial. Thus, the identification of flavor
solvents suggests adulteration rather than
absolutely confirms it.
Non-Natural Flavor Constituents
The vast majority of flavor chemicals used in
the industry are found in nature. It stands
to reason that the best artificial flavors
are made using the same chemicals that
nature used. There are, however, a limited
number of valuable flavor compounds
that have not been found in nature. One
can readily analyze a suspect flavoring
for these compounds. The finding of any
of these chemicals in a natural flavor-
ing unequivocally proves adulteration.
Some flavor chemicals that fall into this
class are ethyl maltol, ethyl vanillin, ethyl-
methylphenyl glycidatae and allyl caproate.
Ethyl maltol is a very good flavor enhancer
for sweet fruit or berry flavors and will
likely be used in the adulteration of these
flavors. Ethyl vanillin can most obviously
be used in the adulteration of vanilla
flavors, but may be used in many sweet
flavors to produce a desired sweet vanilla
character. Ethylmethylphenyl glycidate is
Adulteration 733
most commonly used in strawberry, but
can be useful in other berry flavors. Allyl
caproate is most characteristic of pineapple.
Adulteration by adding flavor chemicals not
found in nature is easy to detect and uncon-
ditionally proves adulteration. Despite this,
adulteration in this manner is relatively
frequent.
Gas Chromatographic Profiles
One can expect to obtain a somewhat con-
sistent gas chromatographic (gc) profile
from a given flavor. For example, the gc
profile of raspberry juice should exhibit
some seasonal, geographical and processing
variation, but these variations will fall
within limits. If one obtains a gc profile
that is abnormal (e.g., unusually high in the
character impact compound), one might
suspect adulteration through the addition of
synthetic chemicals.
The first problem in using this approach
to detect adulteration is in obtaining a
variety of known unadulterated flavorings to
establish representative gc profiles and to be
able to appreciate normal variation. The
second problem relates to the fact that many
pure "natural" flavor chemicals are avail-
able and they can be legally added to a
natural flavoring. Thus, an imbalanced gc
profile may be due to the legal use of pure
"natural" chemicals or the illegal addi-
tion of synthetic chemicals. One can dif-
ferentiate between these two sources of
chemicals as will be discussed later in this
chapter, but a good starting point is to
determine if the added pure chemical is
known to be available commercially and
economically. If not, one has the right
to question the flavor supplier about the
abundance of the compound in question.
This approach to detecting adulteration
is not generally conclusive, but again only
raises suspicions that need to be carried
further.
734 Source Book of Flavors

(R)(-) (S)(+)
Chirality (Optical Activity)
Many flavor constituents are optically active. CR.Sl-
In order for a chemical to be optically 1-Octen-3-ol
active, it must have an asymmetric carbon.
As asymmetric carbon is defined as a carbon
that has four different atoms or groups
attached. Nature will virtually always pro-
duce one optical isomer for a given plant
and given compound. Compounds syn-
thesized in the laboratory via classical (R)(-l !Mushroom!
techniques will yield a racemic mixture of
the two optical isomers (Fig. 17-1). There-
fore, if one would want to determine if
~
an optically active flavor compound was r o
synthesized via an enzyme catalyzed path- ~
way (i.e., from microbial, animal or plant
sources), one would do a chiral-based
separation of the compound and determine 20
the relative proportions of the optical I
Hydrolysis I
isomers. One must recognize that the (Sl(+)
optical isomer formed may well be different,
depending upon the enzymes involved in ~
synthesis (Fig. 17-1). A second considera-
tion is that "natural" flavor compounds
t cr~
C=O
may be formed by "natural" (i .e., FDA
approved) reactions. If this reaction results ~
in the formation of an optically active com-
pound, it would exist as a racemic mixture.
Flavor chemicals formed via the Maillard FIGURE 17-1. Formation of opposite enantiomers
of 1-octen-3-ol during biosynthesis in mushrooms and
reaction would be an example of such enzymic hydrolysis of 1-octen-3-yl acetate by Candida
compounds. uti/is. (Tress! and Engel 1984)
Determination of optical activity of the
flavor compounds of interest can be useful
in determining adulteration. There are few to a natural flavor is to look for inter-
situations where one would expect to find a mediates known to be present in chemically
racemic mixture of an optically active com- synthesized flavor compounds. Living
pound in a natural flavor. Unfortunately, organisms-plant, animal or microbial-
the creative chemist may be able to do chiral use a very different route for synthesis than
specific synthesis or start with materials does the chemist. Thus, we will expect
that already have the desired optical prop- to find unique intermediates in chemically
erties. In these cases, studies on optical synthesized flavor compounds. To illustrate
activity would not be helpful in detecting this approach, examples from Frey (1988)
adulteration. are discussed below.
Neroli is about 40 percent linalool and is
a good target for adulteration due to its high
Trace Contaminants
price. Synthetic linalool could be added
Another approach to determine whether a and provide substantial profit. Chemically
synthetic flavor compound has been added synthesized linalool contains 0.5-2 per-

••
••
,8,, .~,T.IJ,,
•• ••
. I I ,. )' .. - ..r... .
I ( j , l j ~~~~lllo"'>o
70 M -.a
(I
,00
&lASS 138
_____v1
.... a7.o .... ...0 . . . 0
.... 87 . 0 .... ... o •• . o
.... &7.0 .... •. 0 •. 0
FIGURE 17-2. MS of dihydrolinalool (top). SIM analysis of bergamot (left) and
bergamot with 2% synthetic linalool added (right). (Frey 1988)
cent dihydrolinalool, which can serve as a
marker for its addition. The methodology
required here is rather straightforward, if
the pure neroli oil is available for study. The
analyst has to simply inject the neroli into a
gas chromatograph/mass spectrometer and
do multiple ion monitoring keying on the
ions specific for dihydrolinalool. As can be
seen in Fig. 17-2, the ions 73, 123 and 138
are indicative of dihydrolinalool and can
be used for its quantification. One could
use gc for this same task looking for the
dihydrolinalool peak, but gc is much less
sensitive than multiple ion monitoring via
mass spectrometry, and the presence of a gc
peak at the retention time of dihydrolinalool
does not positively confirm its presence.
So mass spectrometry adds the required
sensitivity and identification to prove
adulteration. As is shown in Fig. 17-2, the
addition of as little as 2 percent adulteration
can be detected by this technique.
A second example of this approach is
presented in Fig. 17-3, where synthetic
cinnamic aldehyde is being added to cassia.
In this case, phenylpentadienal is a known
Adulteration 735
i
<- OHL
n .o a7.0 •.. .....
<- OHL
.... 87 . 0 ... ••. o
<- OHL
.... ..,..o .... ...
by-product of the synthesis of synthetic
cinnamic aldehyde. While it is present in
synthetic cinnamic aldehyde at only 400-
SOOppm, this is still adequate to detect 2
percent adulteration. The analyst here keys
on the mass spectral ions 128, 129 and 158
as indicators of the phenylpentadienal and,
thus, synthetic cinnamic aldehyde.
This approach works quite well when one
is looking for the adulteration of incoming
flavoring materials. These materials are
pure and composition is well-defined. The
task of detecting adulterated neroli in a
finished flavoring when the neroli is only
a small part of a complex formulation
becomes much more difficult. One might
argue that dihydrolinalool found in a flavor-
ing came from some other natural product
intentionally added to the flavoring and,
thus, does not constitute adulteration.
Also, the analytical task becomes much
more difficult when the neroli has been
diluted with solvents and other natural
flavor compounds.
A point to keep in mind throughout this
entire discussion of adulteration is that
736 Source Book of Flavors

roOM•'f'
~

sa a
-
....
110 /
eo •o tOO sao , ..o l ao;> eo •o 100 120 140 1 010

TRACE OF w.ss 15!!

<-INT.
PPDA?
STD.
\
' aaI. o ' I
4 0 .0
,. I
4 1.0 39 . 0 41 . 0 42 . 0
I
48 . 0

1 I 11
•• . o

FIGURE 17-3. MS of PPDA and the internal standard of 2-methoxy naphthalene

(top). SIM analysis of cassia oil (left) and cassia with 2% synthetic cinnamic aldehyde
added (right). (Frey 1988)

the adulterer may be as knowledgeable
and sophisticated as a policeman. If the
adulterer knows that dihydrolinalool is a
key for detecting its presence in neroli, he
can be certain to add a small amount of
a flavoring material known to contain
dihydrolinalool or put some effort into
removing the dihydrolinalool from the
synthetic linalool. If the additional cost of
cleaning up the linalool doubles its price,
the profit is still exceptional.
Stable Isotopes
The stable isotopes of interest are 13C, D
eH) and 180. Unlike 14C, these isotopes do
not undergo radioactive decay and, thus,
are constant throughout time.
Isotope abundances are typically ex-
pressed in the delta (8) notation and written
relative to the heavier mass isotope . The 8
values are defined as the parts per thousand
(%o) deviation of the sample isotopic ratio
versus that of a standard:
%o = [(Rsample/Rstandard) - 1] x 103
Where R = 13C/12 C or D IH.
The reference standards used are available
from the National Bureau of Standards.
The stable isotopes of carbon exist in
nature at relative proportions of 1.11:98.89
( 13C YC). The abundance of 13C in dif-
ferent plants is slightly different, depending
upon the atmospheric C02 from which it is
derived. Through photosynthesis, plants
selectively enrich 12C content and reduce
the 13C content. The amount of 13C reduc-
tion depends upon the photosynthetic path-
way the plant uses: Calvin (C-3 pathway);
or Hatch-Slack (C-4 pathway). Flowering
plants such as apples, grapes, cherries,
citrus fruits , sugar beets, rice , wheat, rye ,
 Adulteration 737

potatoes and cassia use the Calvin pathway. TABLE 17-2. Stable Carbon Isotope Values for
Plants using the Calvin pathway have result- Authentic and Synthetic Vanillins
ing isotopic abundances ranging from -24
Vanillin afer
to -32%o. the removal of
The stable isotope of hydrogen, deute- Vanillin Source Vanillin Methoxy Group
rium, exists in nature at relative abundances
of 0.015 and 99.9 percent (D: H). The oD Bourbon• -20.2
Madagascar• -20.5
ratios have proven useful in determining Com ores• -20.0
adulteration in wines (Bricout, Fontes -18.7
and Merlivat 1975), linalool, citra! and Mexicanb -20.3
menthol (Bricout, 1982), and bitter almond Tahitianb -16.8
oil (Butzenlechner , Rossman, and Schmidt Synthetic
1989). Lignin• -27.0 -26.7
While oD values are influenced by Guaiacol• -29.5 -29.2
Eugenol (clove)b -30.8
the metabolic activity of the plant, the
Lignin+ 1% +92.3 -25.4
deuterium/hydr ogen ratio of the source enriched 13 C
water and local environmental conditions Lignin + 7/10,000 -20.0 -26.0
is considered more important (Yapp and enriched 13 C
Epstein 1982). a Hoffman and Salb (1979)

The use of stable isotopes, particularly bBricout eta!. (1981)

13 C, to detect adulteration in flavoring

materials has been longest applied to the

adulteration of vanilla (Bricout 1974;
Hoffman and Salb 1970; Krueger and
Krueger 1983; Krueger and Krueger 1985;
Riley and Kleyn 1989). Vanilla is a rela-
tively expensive product, which obtains
its primary flavoring power from vanillin.
Vanillin is readily synthesized from several
sources (e.g., lignin, eugenol or guaiacol) at
low cost. McCormick (1988) illustrated the
financial incentive for adulteration by noting
that one gallon of single-fold vanilla flavor
can be made by using 1 oz. of synthetic
vanillin at a cost of 33¢ or the proper
amount of vanilla beans at about $40.
The 13C/ 12 C isotope ratios for vanillin
obtained from natural sources and synthetic
sources are presented in Table 17-2. It
is apparent from this data that authentic
vanillin can be readily distinguished from
synthetic sources. The financial incentive
for adulteration has resulted in adulterers
attempting to circumvent this method of
detecting adulteration. The most common
approach has been to enrich the methoxy
group of synthetic vanillin with Be. The
corresponding policing response was to
examine the vanillin selectively with and
without the methoxy group for 13C. By
choosing the proper ratio of 13 C enriched
vanillin, the overall Be ratio falls in the
authentic range, but analysis without the
methoxy group indicates adulteration (See
Table 17-2).
The economic incentive for adulteration
of vanilla is so enticing that the adulterers
are continuously finding ways to circumvent
current policing work. It appears that this
will be a never-ending game.
Stable isotopes have been used to monitor
adulteration of several other flavoring
materials, as was mentioned earlier. Of
substantial interest is oil of bitter almond
(benzaldehyde) . Culp and Noakes (1990)
have published some work demonstrating
how isotopes ( 14C, D and 13 C) can be used
to detect adulteration in benzaldehyde and
cinnamic aldehyde. Some of their data are
summarized in Table 17-3. For cinnamic
aldehyde, the 13 C data will provide some
indication of adulteration, but the values are
quite close, so significant levels of adultera-
tion are possible before one could definitely
conclude that the sample was adulterated.
However, the (D) data show major dif-
738 Source Book of Flavors

TABLE 17-3. Isotopic Analysis of Cinnamic Aldehyde and Benzaldehyde (Culp and
Noakes 1990)

Cinnamic Aldehyde
Sample Source 14c 013C %o oD"/oo
dpm/g c· PDBb SMOW'

Botanical Extracts 16.6 -27.6 -127

SDd 0.9 0.4 9
Natural Oils 16.2 -27.5 -115
SD 0.6 0.7 10
Synthetic via toluene oxidation 0.2 -25.7 517
SD 0.1 0.3 52
Benzaldehyde
Botanical Extracts 15.6 -27.9 -98
SD 0.2 0.4 23
Natural Oils 16.3 -28.6 -108
SD 0.4 0.7 16
Synthetic via benzyl chloride 0.0 -26.2 627
SD 0.1 0.5 32
Synthetic via toluene oxidation 0.0 -26.2 627
SD 0.1 0.5 32
a Degradations per minute
b Parts per thousand relative to belemnite from the feeder formation of South Carolina
'Parts per thousand relative to Standard Mean Ocean Water
ct Standard deviation

ferences between the natural and the
synthetic cinnamic aldehydes. The same
observations can be made for benzaldehyde.
Therefore, the deuterium data are more
useful in detecting adulteration of these two
aldehydes than are the 13 C data. (The 14C
data will be discussed in the next section of
this chapter).
From the data presented in the literature,
one is inclined to feel secure that adultera-
tion can be determined with accuracy by
stable isotope methods. These methods can,
unfortunately, be circumvented. This will
also be discussed in the next section of this
chapter.
Radioactive Isotopes e C)
4
It is generally known that chemicals syn-
thesized from petroleum sources have no
14 C and, thus, 14C determinations will dif-
ferentiate between flavor compounds
derived from petroleum and recent plant
sources. Plants take up 14 C from the atmo-
sphere as C0 2 and through photosynthesis
fix the 14 C in all carbon containing con-
stituents of the plant. Prior to 1950, atmo-
spheric 14C activity was 13.56 disintegrations
per minute per gram of carbon (dpm/g C),
which was defined as 100 percent modern
activity. Nuclear testing resulted in 14C
activity increasing to a maximum of 28 dpm/g
C in 1964. Due to a ban on atmospheric
testing of nuclear weapons, the 14C level in
the atmosphere has decreased. This is due
to a combination of uptake and exchange
with the oceanic bicarbonate system, dilu-
tion by 14 C devoid fossil fuel and uptake by
the earth's biomass. Thus, recent plant tissue
(or products) could be dated accuracy-based
on the level of 14C activity. The interest is,
however, in determining whether a flavor-
ing material has been synthesized from
petroleum source or recent plant/animal
metabolism.
The 14C analysis is tedious, costly and
requires substantial quantities of pure
material. Culp and Noakes (1990) used up

to 6 g of benzaldehyde or cinnamic aldehyde
in their 14C determinations.
Numerous studies have demonstrated the
utility of 14C in determining if a flavor-
ing material was synthesized from petro-
leum sources. (See Table 17-3 or Byrne,
Wengenroth and Krueger 1986). However,
the adulterer has at least two means of
circumventing detection by this technique.
First, the adulterer can use recent plant
material as a starting material for chemical
synthesis. Examples here could be to use
cinnamic aldehyde from cassia to make
benzaldehyde or pine terpenes to make a
host of other more valuable terpenes. The
second approach is to add a small amount of
14C enriched compound to the synthetically
made material. Since there is only about
1.3 X 10- 10 parts 14C per part 12C, a
little enriched 14C will go a long way in
adulteration.
The adulterer has another loophole in
this methodology-it takes a large amount
of pure material to obtain results. What is to
keep the adulterer from collecting 10 g of
pure natural benzaldehyde from peach pits,
send it out for analysis, obtain 14C and
13 C/12C data to demonstrate authenticity,
and then forever use synthetic benzaldehyde
in all flavorings? Once a flavoring material is
added to other botanicals, essential oils,
solvents and other pure chemicals, it is dif-
ficult to separate out the suspect chemical at
the required purity and quantity. In this
way, the adulterer can reasonably and safely
hide behind a certificate of authenticity and
sell whatever he wants.
Many of the same statements made about
weaknesses in 14C determinations to detect
adulteration also can apply to stable isotope
determinations. Stable isotope analyses
require large quantities of pure material that
is not easy to obtain from finished flavor-
ings. One can search for starting materials
that have the desired 13C/ 12C or D/H ratios
or alternatively enrich the material with 13 C.
The sophisticated adulterer can circumvent
detection by either 14C or stable isotope
analyses.
Adulteration 739
ADULTERATION OF
ESSENTIAL OILS
Diluting An Expensive Oil
With a Less Expensive Oil
There is substantial incentive to dilute a
more costly essential oil with a less expen-
sive oil. An example is the dilution of
peppermint oil with oil of cornmint. The
approach used to detect adulteration is to
search for a constituent found in peppermint
that is not present in oil of cornmint. One
can key on sabinene hydrate that is found in
peppermint oil at about 1 percent of the
oil and is not found in oil of cornmint (Fig.
17-4). One is essentially looking for a rea-
sonably unique constituent in an oil and
see that it is at the anticipated level. An
additional example would be ~-selanine
in oil of celery. ~-selanine should be present
at 7-7.5 percent in oil of celery unless
the oil has been cut with another oil or
solvent.
It is essential to key on components that
are unique to the oil being studied and that
the constituents not be readily available as
pure chemicals.
Lemon Oil Adulteration
Cold-pressed lemon oil can be extended
with low-cost, readily available steam-
stripped lemon oil. To cover up the
adulteration, the adulterer must add citral
to boost flavor and uv absorbers to bring
the oil back into specifications for uv
absorbance. McHale and Sheridan (1988)
have studied the uv absorbers in lemon oil
by HPLC in order to better understand the
source of normal uv absorption in lemon oil,
and to determine if one can key on added uv
absorbers to indicate adulteration.
The uv absorbers known to be used to
boost uv absorption in adulterated lemon
oil are: 1) "sun esters," a mixture of
menthyl salicylate and anthranilate; 2)
ethyl-p-dimethylamino benzoate; 3) cold
pressed oils of grapefruit and lime; 4) 7-
methoxycoumarin; and 5) 5,7-dipropyloxy-
740 Source Book of Flavors

Oil of
Corn mint

ll l l Jlu

.. ..
...;;
0 c
.,
0
.c
....0
.,
.c

....
0
I
.,
c

"
I
0
c
_,"
..
I

I I I
.,.
..". ...
c
.
~

Oil of ~
-~ ·c."
Peppermint 'i"a I

"' """c
:c
:
~
~

l Ill II 1
I Ll I ~ t
FIGURE 17-4.
__, 1
Peppermint/cornmint adulteration (top= cornmint, bottom=
~--
peppermint).

4-methylcoumarin (McHale and Sheridan (Fig. 17-5). They found 25 percent of

1988). Through the use of HPLC tech- the commercial lemon oil on the United
niques, McHale and Sheridan (1988) have Kingdom market to be adulterated. The
been able to detect these added uv absorbers most common additive used to impart uv

500
42)0
2
> 300
E
:J
a: 200
E
100
0
0 10 20
T ime
FIGURE 17-5. Chromatogram of adulterated lemon oil sample . (McHale and
Sheridan 1988)
absorption was ethyl-p-dimethylamino
benzoate. Uv absorbers (auraptene) com-
mon to grapefruit were also found in a
number of lemon oils.
Conclusions
There is substantial fin ancial incentive to
adulterate flavoring materials. While the
vast majority of flavor companies are ethical
and would not knowingly adulterate a pro-
duct, a few opportunists are less ethical and
adulterated products do reach the market.
They may reach the market through direct
sales to consumer product companies or
through the sale of adulterated raw materials
to another flavor company. The policing of
adulteration is done within the industry in
order to maintain corporate ethics (i.e., not
sell adulterated products) and for financial
reasons (i.e., not permit a competitor unfair
market advantage). Policing is also done
by some of the larger food companies that
are also image-conscious and do not want
the publicity of selling fraudulent (i.e.,
mislabeled) products.
As should have been evident from read-
Adulteration 741
14
30 40
(m i n . )
ing this chapter, there are many ways to
detect adulteration in a flavoring material.
Most of these techniques, however, are
very costly both in terms of time and
instrumentation. Also, the ability to detect
and then unequivocally prove adulteration
is questionable. The companies involved
in adulteration have the same knowledge,
financial resources, instrumentation and
creativity as the companies attempting to
police them. There are ways to elude virtu-
ally every method of detecting adulteration.
The ultimate deterrent to adulteration is
a lack of financial incentive. This could
come from a change in the law to permit the
use of any safe flavor chemical, irrespec-
tive of source, to make the best flavoring
possible. Changes would also have to
be made in labeling laws and consumers
educated not to distinguish between natural
and artificial. Alternatively, we can proceed
on the route that we have been follow-
ing, i.e., to keep on improving analytical
methods of detecting adulteration so that
adulterers have to do so much to adulterate
a product (e.g. , clean synthetic chemicals of
impurities, incorporate 13 C and 14C) that
742 Source Book of Flavors
it is no longer economical. While the
first solution is most scientifically and
economically sound, our laws are not based
on either criterion; they are politically
based. Therefore, it is questionable whether
these changes will ever occur and we are
most likely doomed to the continued cat and
mouse game-a sad waste of resources
and a cost to the consumer in dollars and
quality.
References
Bricout, J. 1974. Analysis of stable isotopes
of carbon in quality control of vanillas.
J.A. O.A. C. 57:713.
Bricout, J., Fontes, J.C., Merlivat, L. 1975. Sur
Ia composition en isotopes stables de !'ethanol.
Ind. Alimt. Agric. 92:375-378.
Bricout, J., Kozlet, J., Derbesy, M., and Beccat,
B. 1981. New possibilities with analysis of
stable isotopes of carbon in quality control
of vanillas. Annates des Falsifications et de
/'Expertise Chimique. 74(803):691.
Bricout, J. 1982. Possibilities of stable isotope
analysis in the control of food products. In
Stable Isotopes, Conference Procedures, eds.,
H.L. Schmidt, H. Forstel, H. Heinzinger, pp.
483-494. New York: Elsevier.
Butzenlechner, M., Rossmann, A., and Schmidt,
H.L. 1989. Assignment of bitter almond oil to
natural and synthetic sources by stable isotope
ratio analysis. J. Agri. Food Chern. 37(2):
410-412.
Byrne, B., Wengenroth, K.J., and Krueger,
D.A. 1986. Determination of adulterated
natural ethyl butyrate by carbon isotopes. J.
Agri. Food Chern. 34(4):736-738.
Culp, R.A. and Noakes, J.E. 1990. Identifica-
tion of Isotopically Manipulated Cinnamic
Aldehyde and Benzaldehyde. J. Agri. Food
Chern. 38(5):1249-1255.
Frey, K. 1988. Detection of Synthetic Flavorant
Addition to Some Essential Oils by Selected
Ion Monitoring GC/MS. In Developments in
Food Science. Flavors and Fragrances: A
World Perspective, eds. B.M. Lawrence, B.D.
Mookherjee and B.J. Willis, pp. 517-524.
Amsterdam: Elsevier.
Hoffman, P.G. and Salb, M. 1979. Isolation on
Stable Isotope Ratio Analysis of Vanillin. J.
Agri. Food Chern. 27(2):352-355.
Krueger, D.A. and Krueger, H.W. 1985. Detec-
tion of fraudulent vanillin labeled with 13-C in
the carbonyl carbon. J. Agri. Food Chern.
33(3):323.
Krueger, D.A. and Krueger, H.W. 1983. Carbon
isotopes in vanillin and the detection of
falsified "natural" vanillin. J. Agri. Food
Chern. 31(6):1265.
McCormick, R. 1988. Vanilla and vanillin remain
ever-versatile ingredients. Prepared Foods.
157(2):123.
McHale, D. and Sheridan, J.B. 1988. Detection
of Adulteration of Cold-Pressed Lemon Oil.
In Developments in Food Science. Flavors and
Fragrances: A World Perspective, eds. B.M.
Lawrence, B.D. Mookherjee and B.J. Willis,
pp. 525-535. Amsterdam: Elsevier.
Riley, K.A. and Kleyn, D.H. 1989. Fundamental
Principles of VanillaNanilla Extract Process-
ing and Methods of Detecting Adulteration in
Vanilla Extracts. Food Techno/. 10:64-77.
Tress!, R. and Engel, K.H. 1984. Formation and
analysis of optically active aroma compounds.
In Analysis of Volatiles: Methods and Applica-
tions, ed. P. Schreier, pp. 323-342.
Yap, C.J. and Epstein, S. 1982. Climatic sig-
nificance of the hydrogen isotope ratio in tree
cellulose. Nature. 297:636-639.
Chapter 18
Statistical Methods
By Maureen Lahiff and Jane V. Leland

STATISTICS IN FLAVOR- ordered hedonic categories is analysis of

A GENERAL OVERVIEW variance (ANOV A) with follow-up multiple
comparisons. When the subjects are asked
Statistical analyses can make major con- questions with two possible answers (yes-no
tributions to flavor work in several areas or acceptable-unacceptable), the resulting
such as product development, quality con- proportions or percents can be analyzed by
trol and sensory instrumental-correlation. other techniques.
While from the scientist's point of view In typical product development studies, a
these areas seem distinct, from a statistical number of features of a product must be
point of view they overlap. This overview investigated simultaneously. For example,
sketches a context for the use of statistics in supplier and amount of savory flavor,
flavor; systematic coverage of techniques is amount of salt, fat level and processing
the focus of the next section. method may all be thought to influence
The flavor quality of a product results flavor liking scores. If the number of possible
from the added flavor system, other features test formulations is too large for a panel
of the product formulation, processing, the to evaluate in one session, experimental
interaction among these three, the age of designs called fractional factorials allow the
the product and other factors. Choosing a developer to determine which factors have
formulation, assessing the sensory impact of the most impact, using subsets of the total
cost reduction efforts, examining flavor loss possible combinations.
or change over shelf life, and determin- Relationships between sensory scores and
ing whether or not lots of product or raw formulation and processing variables can be
materials meet specifications are all ques- modeled by regression techniques. Suppose
tions that share a common statistical frame- a developer has conducted an experiment to
work. In such cases, determining whether study how amount of savory flavor, amount
there are systematic differences in sensory of salt, fat level and processing method
or consumer scores between samples and affect flavor liking score. Regression uses
quantifying any differences is essential. One the data to develop a function that relates
way to analyze attribute or overall liking liking score to these variables. This function
data collected with continuous line scales or gives the developer information about the
743
744 Source Book of Flavors
contribution of each variable separately and
in concert with the others. The regression
equation can also be used to predict lik-
ing score given any setting of each of the
formulation and processing variables, or to
discover optimal settings of these factors.
When the investigator's goal is product
optimization, the regression models are
often called response surface models.
Regression can also be used to model rela-
tionships between sensory scores and
analytical measurements such as volatile
peaks. This is one way of exploring sensory-
instrumental correlation.
In conjunction with sensory data, volatiles
play a central role in flavor. Statistical
analyses of volatile profiles can help the
investigator determine which volatiles dis-
tinguish products and manipulate formula-
tion and/or processing parameters to
achieve a specifically desired or optimum
flavor profile. Determining which volatiles
are associated with an off-flavor is a similar
problem. Another class of problem where
statistical analyses are useful is discovering
which volatiles contribute most heavily
to differences among samples from dif-
ferent geographic regions (such as wines or
coffees) or different suppliers. To answer
these types of questions, multivariate
statistical methods such as principal com-
ponent analysis, multivariate analysis
of variance (MANOVA), discriminant
analysis and logistic regression can be used.
Multiple regression can also contribute
insight. These same methods are also appro-
priate for analyzing data from experiments
in which a sensory panel has scored several
flavor attributes, or an analyst has measured
several non-volatiles impacting flavor.
In addition to helping the user determine
which volatile peaks or sensory attributes
matter, multivariate statistical methods also
offer a way to produce, from all the peaks,
two or three new variables that seek to
capture the essential features of the data.
If they succeed, then the values of these
new variables can be plotted so that the
similarities and differences between samples
can be examined visually. (This is referred
to as dimension reduction.)
In this chapter, we discuss the statistical
techniques already mentioned along with
several others. The depth of coverage
reflects our sense of the centrality of the
methods. We focus on how to interpret and
clearly express statistical conclusions.
As a result, we did not spend the space to
incorporate graphical displays as fully as
we might have. However, we know from
experience how useful graphical displays of
data can be and strongly encourage their
use. While we have kept those with little
previous knowledge of statistics in mind,
much of the discussion assumes some
familiarity with elementary statistics. We
do, however, review the concepts essential
for interpretation. The references are user-
oriented; while they will undoubtedly be
superseded, they can be relied upon for
the basic framework. For each technique
discussed, we highlight the questions the
technique helps answer and the kinds
of data for which it was developed. The
next section gives a detailed overview of
techniques.
GETTING STARTED
This section gives several examples that
illustrate technique selection and the use of
more than one statistical method to get
a fuller understanding of the situation
being studied. Since the types of variables
measured are important in choosing appro-
priate methods, this material is reviewed
first. (Readers familiar with the terms
italicized in the next subsection may wish
to skip it.)
Variable and Data Types
Three main types of variables are important
for our purposes: nominal, ordinal and con-
tinuous. Nominal variables have unordered
categories. Source of sweetener and type of
vegetable oil used for frying are examples
of nominal variables. Nominal variables
 Statistical Methods 745

USPONSE PRijD;ICTORS I J!!XPLNfATORX Y!BUBJ.ES ucnxom;s

PREDIC'.riNG OR ASSESSING AND ES'.riiiA'.riNG IUTEC'.rS

-{
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•CoDtiDUOUB aDd
CoDtiDUOUB Categorical Predictor•
llaapoDae

Categorical BzplaDatoz:y )lo DOVA

Variable a

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•CoDtiDUOUB aDd [llaltivariate
Several ReqreaaiOD]
Categorical Predictors
CoDtiDUOUa
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Categorical BxplaDatoz:y ~ IIDOVA
Variable•

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FIGURE 18-1. Taxonomy of basic techniques.

746 Source Book of Flavors
with only two categories, i.e., determina-
tion of spoiled or unspoiled, are called
binary variables. Ordinal variables are also
categorical, but the categories are ordered.
Some examples of ordinal variables are:
USDA quality grades of meats, size grad-
ings of eggs, sharpness of Cheddar cheese.
Continuous variables are those whose values
form an interval on a real line. Weights,
lengths, amounts and percents are con-
tinuous. Ordinal variables with many
categories are often analyzed using con-
tinuous variable techniques, even though
the distances between categories cannot
be assumed equal. Hedonic scales are a
common example. The more points on the
scale (i.e., nine point versus five point),
the more appropriate the use of continuous
variable techniques. Count data are usually
treated as ordinal if the counts take on only
a few values; if the counts can take on a
wide range of values, the data are usually
treated as continuous, especially if there is
no logical upper limit to the count. (In many
presentations, continuous variables are
further subclassified as interval scale or ratio
scale. This distinction is not important for
selecting statistical methods.)
In many statistical analyses, one variable
is singled out as the response variable and
the other variables are viewed as explana-
tory variables or predictor variables. The
response variable usually represents a
characteristic (such as sensory score) that
the investigator would like to control,
optimize, or predict, while the explanatory
or predictor variables represent charac-
teristics of the raw materials, process-
ing methods, formulation, etc. In other
analyses, there may be several responses
that are to be handled as an ensemble rather
than analyzed one at a time. It is this type of
data that is called "multivariate."
Selecting Techniques
Figure 18-1 provides a "tree" in which
statistical problems are organized under
three broad goals: predicting and estimating
effects, optimizing formulations and search-
ing for patterns, such as underlying struc-
ture or subgroups, in multivariate data.
Under each goal, the possible kinds of
variables are listed, followed by a partial
list of appropriate techniques. This list is
not meant to be comprehensive, rather it is
designed to enable someone unfamiliar with
the techniques to get started. For the predic-
tion and effect estimation techniques, the
kind of response variable is given first,
followed by various kinds of possible
explanatory or predictor variables. Due
to the nature of the search for patterns
techniques, no one variable is singled out as
the response. We now give several examples
to illustrate technique selection.
As a first example, consider an inves-
tigator who wants to determine whether
consumers give different overall liking
scores to four different formulations of
juice-based drinks. Consumer ratings are
done on a continuous line scale. If there are
some differences, the investigator wants
to know which formulation or formulations
are rated highest. Analysis of variance
(ANOVA) with follow-up multiple com-
parisons can be used because the consumer
ratings are on a continuous scale, and
because the formulation is a categorical
explanatory variable (the four different
formulations are handled as four different
treatments).
Suppose the investigator expanded her
study of juice-based drinks, collecting
analytical measurements on the sugars,
other carbohydrates and acidity of the
drinks, and collecting data on the volatile
compositions of the drinks by gas chroma-
tography. Discriminant analysis can be used
to see which volatile peaks distinguish the
formulations, since the four treatments
define four groups and the volatile peak
areas are continuous variables. Regression
can be used to model the relationship
between consumers' overall liking scores
and the four analytical measurements, since
both the response and the explanatory
variables are continuous. A particular type

of regression analysis called response surface
analysis can be used for optimization, that
is, to identify formulations that might lead
to even higher overall liking scores. If the
formulations are different blends of the
same set of ingredients, a response surface
analysis can be carried out on data obtained
from a mixture design.
As a second example, consider an
off-flavor problem that has arisen with
packaged pilaf mixes. The researcher asks a
sensory panel to score cooked samples as
acceptable or unacceptable for serving
to guests, obtaining a yes or no answer.
Volatile peaks are obtained from the same
samples. Discriminant analysis and logistic
regression can be used to find the volatile
peaks that differ between the acceptable
and unacceptable samples since the response
variable, yes or no, is binary and the volatiles
used as predictors are continuous. While
visual inspection of the profiles may suffice
in simple cases, these statistical techniques
are useful for detecting subtle changes in
balance.
As a third example, suppose an oenologist
has asked wine enthusiasts to compare
pairs of red wine samples and to assess the
similarity of the two wines in each pair on a
scale of zero to 50, with 50 representing
virtually identical wines. (To convert the
wine similarity ratings into distances, the
oenologist could subtract the enthusiasts'
scores from 50 so that highly similar wines
would have distances close to zero. Cluster
analysis can be used to find groups of similar
wines. Multidimensional scaling can be used
to construct a visual representation or map
of the wines. These are the primary tech-
niques for analyzing similarity or distance
data. If continuous measurements such as
volatile or other chemical data were also
collected on the wines, cluster analysis and
principal components could be used to find
groups of similar wines. With such con-
tinuous data, principal components can give
a richer interpretation; however, cluster
analysis is also useful since the clusters from
the laboratory data can be compared to the
Statistical Methods 747
clusters from the tasters' overall distance
judgments. In addition to an informal com-
parison of the two groupings, the principal
components could be compared to the
axes obtained in multidimensional scaling.
Plotting and multiple regression could be
used to relate the principal components and
the axes constructed by multidimensional
scaling.
A fourth example involves a researcher
who asks consumers to rate frozen dessert
preparations on a three-point scale: like
very much, like somewhat, or dislike. The
desserts have been constructed from four
bases, using three types of sweetener and
three different flavorings. Because all
the variables are categorical, log-linear
models can be used to see how the propor-
tions of liking categories depend on the base
type, sweetener and flavoring. Log-linear
models are not regression models in which
variables have been logged, but are a special
class of models designed for distributions
that occur with count data.
As a final example, suppose that a
researcher is developing a new line of
fruited cottage cheese. In the first phase of
the project, a large number of the product's
features are of interest: moisture content,
fat level of the cottage cheese, amount and
size of fruit pieces, amount and type of
sweetener, if any, and use of salt and other
flavor enhancers. With this many factors,
the number of possible test products is too
large for a sensory panel to evaluate in one
session, even if only two levels are used for
each factor. A properly planned fractional
factorial experiment using a subset of the
possible combinations allows the researcher
to assess the impact of each factor and
some of the factor interactions using
ANOVA. After the first phase data have
been analyzed, experiments focusing on the
factors that emerge as key can be carried
out. In addition to ANOVA, regression
could be used to model the sensory response
since some of the factors are levels of
continuous variables. Response surface
methods could be used to locate other
748 Source Book of Flavors
formulations that are likely to have high
sensory scores.
Before presenting each of the statistical
techniques in more detail, we next discuss
several fundamental concepts that cut across
these techniques.
ESTIMATION AND HYPOTHESIS
TESTING
Estimation and Confidence Intervals
Estimation is one of the basic building
blocks of statistics, a way of summarizing
sample information about various quantita-
tive features (called parameters) of the
population. In addition to obtaining a
point estimate of the population parameter,
statistical estimation includes an assessment
of how closely the sample has enabled us to
estimate the population parameter.
The perspective taken by "classical"
statistical theory is that the population
parameter being estimated is a fixed, con-
stant value that would be known, if the
investigator had access to the entire popula-
tion and could precisely measure each of the
population members. For example, suppose
that the population of interest is consumers
of carbonated beverages in the United
States, and the parameter of interest is the
mean consumer liking for a new beverage.
In practice, no investigator would spend
the time and money to get the true value
of the population mean; the average of
a large, random sample is used as an
estimate. (Note: The classical theory also
assumes that there is a well-defined popula-
tion being studied. Its definition may
have to be qualified to correspond to our
ability to collect data, but there must be a
population.)
The larger the sample, the more accurate
the estimate. To quantify the accuracy, we
introduce a repeated-sampling framework.
Suppose we have decided to use a sample of
size n = 100 to estimate the population
mean. If we actually took several dis-
tinct random samples, each of size 100, the
sample averages X would all be slightly dif-
ferent, due to the different values obtained
from the individuals in the samples. If we
took many samples of size 100, we could
imagine treating the collection of X values
as data points. A study of the X from all
possible samples of size 100, the sampling
distribution of X, shows that the X always
have a mean equal to the population mean
J.1 (X is an unbiased estimator of J.l), and
a variance equal to ~In, where cr2 is the
variance of the population. The standard
deviation of the X values, cr/Vn, is given a
new name: the standard error of X. In
saying that cr/Vn represents sampling
"error," "error" simply means the inherent
sample-to-sample variability. (Note: the
cr/Vn formula for the standard error of X
holds only for simple random samples; there
are other standard error formulas for dif-
ferent sampling plans such as stratified
sampling.) In practice, the population
standard deviation a is estimated by the
sample standard deviation, s, and the
standard error of X is estimated by s/Vn.
For example, suppose a random sample
of n = 200 consumers rated a new carbonated
beverage on a 10 em continuous scale.
Suppose the average overall liking X =
7.2cm and the sample standard deviations
= 1.30 em. The estimated standard error of
X is 1.30cm/v'200 = .092cm.
The sample average, X, is an estimate
of the population mean J.l. An interval
estimate of J.l called a confidence interval
can be calculated from X and its estimated
standard error. Given a particular sample,
a confidence interval for J.l answers the
question: what range of values of the
population mean J.l might have produced
our sample? Calculation of confidence
intervals is straightforward: the general pat-
tern is sample point estimate ± a multiple of
the estimated standard error. For a popula-
tion mean, a confidence interval is X ± a
multiple of s/Vn, with the multiple chosen
from a t distribution with n - 1 degrees of
freedom.
In the carbonated beverage example,

a 95% confidence interval for the popula-
tion mean (using the normal curve as an
approximation to t with 199 degrees of
freedom) is 7.2cm ± .18cm, or 7.02cm to
7.38cm. The procedure we used, multiply-
ing the estimated standard error of X by
1.96, gives an interval that contains the
(unknown) population mean in 95 out of
100 applications. Strictly speaking, it is not
correct to say "the probability that Jl is in
the confidence interval we found is 95%". If
the population mean Jl really were 7.35 em,
then Jl is in our population interval (the
probability is 1); if Jl really were 7.0cm,
then Jl is not in our interval (the probability
is 0).
Based on our sample, we cannot find an
interval that includes the true population
mean with certainty, since we can never rule
out the sample being one of the rare ones
that gives X very far from Jl. The con-
fidence interval procedure offers us a long-
run probabilistic guarantee: The interval
formula is set up so that the interval will
include (or "cover") the true population
mean in a very high percent, usually 95
or 99, of applications. For any particular
sample, we do not know if we are in one of
the 95 out of 100 cases where Jl really is
in the interval we calculated, or whether
we are in one of the five out of 100 cases
where the sample came out so extreme that
(unknown to us) Jl is not in the interval we
calculated.
One of the things we can do, if we have
some idea of the magnitude of the popula-
tion variance from previous work or studies
of similar populations, is to use the standard
error formula to calculate the sample size
required to ensure that a large proportion of
the possible samples give X close enough to
the population mean. How close we need
to be depends on the intended use of the
estimate. For a large enough sample size, n,
the histogram of the X from all possible
samples is approximately normal, so we
know that about 95% of the sample X
values will be within two standard errors,
that is within 2cr/Vn, of Jl. However, this is
Statistical Methods 749
a long run probabilistic guarantee; we have
no way of knowing whether our particular
sample X is very close to Jl or is more than
two standard errors away.
The interpretation outlined here applies
to all confidence intervals and prediction
intervals. The general pattern of point
estimate ± multiple of the estimated stan-
dard error holds for means, differences
of means, linear combinations of means,
regression coefficients, estimates of means
and predictors in regression, among others.
The t distribution is used to get the multiple
in all these problems; the degrees of free-
dom always depend on the sample size,
though the exact formula varies. Confidence
limits for variances are multiples of the
sample variance.
Hypothesis Testing
The logic of statistical hypothesis testing
is similar to the classic model of scientific
inference in which the experimental con-
sequences of a hypothesized theory are first
derived. If the experimental results con-
tradict the theory, the theory is declared
incorrect or inadequate, and the scientist
seeks to revise it. If the experimental results
do not contradict the theory, it is subjected
to further testing. The statistical version
goes as follows. The null hypothesis takes
the role of the scientific theory. The state-
ments "the means of these two groups are
the same," or "the slope of this regression
coefficient is 0" are examples of null
hypotheses. The question "Does the sample
contradict the null hypothesis?" no longer
has a yes or no answer; it is instead answered
by calculating probabilities. Assuming that
the null hypothesis really does describe the
population from which we are sampling,
how rare is the sample we got, how extreme
is it? If the sample we actually obtained
would be a rare occurrence from a popula-
tion such as the null hypothesis describes,
then we conclude that the data contradict
the null hypothesis. That is, we reject the
null hypothesis, concluding that it does not
750 Source Book of Flavors
adequately describe the population under
study. We could be making a mistake when
we do this. The statistical approach says, in
effect, we have to decide whether it is more
plausible to believe that the null hypothesis
holds for the population and that a rare
event has occurred, or to believe that the
sample gives enough evidence to convince
us that the null hypothesis is not a satisfac-
tory description of the unknown population.
In the carbonated beverage example,
suppose that experience indicates that a
mean liking score of 7.0 em is required for
a beverage to gain enough market share to
be profitable. Do the test results with 200
consumers indicate that the new beverage
will be profitable? If the consumer popula-
tion mean were 7.0cm, would we get a
sample X as high as the 7.2 em that we got or
higher just as a result of sampling 200 con-
sumers? Assuming that our sample standard
deviation s = 1.30 em is close to the popula-
tion deviation cr, and assuming that the
sampling distribution of X is approximately
normal, less than 15 out of 1000 samples
from a population with mean 7.0cm have X
= 7.2 em or higher. Our sample X is rare if
the population mean really is 7.0 em. Thus,
we conclude that the new beverage really
does have a mean liking score greater than
7.0cm.
Suppose that a well-established car-
bonated beverage is known to have a mean
liking score of 7.3 em. Do the test results (X
= 7.2cm, s = 1.30, n = 200) indicate that
the new beverage is different from 7.3cm?
Under the same assumptions made in the
previous test, it turns out that about 28
percent of samples from a population with
mean of 7.3 em have average liking scores
0.1 em or more away from 7.3 em (in either
direction). In this case, the data do not
provide evidence that the mean liking score
for the new beverage is any different from
7.3cm.
P Value and Significance Level
Confronted with the same sample, different
researchers may reach different conclusions.
There are some generally agreed-upon
conventions: If the probability of a sample
as extreme or more extreme than the sample
we got is less than 5 percent, the usual
conclusion is to reject the null hypothesis.
The cutoff level selected, traditionally
denoted by a, is called the significance level
of the test. Some researchers use a 1%
cutoff. In general, the lower the probability
of getting a sample this extreme, (called the
P value, observed significance level, or
attained significance level) the stronger the
evidence against the null hypothesis.
On the other hand, if the sample we
obtained is not unlikely from a population
such as the null hypothesis describes, then,
as in scientific inference, we reserve judg-
ment. The most careful way to phrase the
conclusion in such cases is: The sample data
do not provide strong evidence that the null
hypothesis does not hold for the popula-
tion. The double negative here does not
automatically collapse; this statement is not
logically equivalent to concluding that the
sample data provide evidence that the null
hypothesis does hold for the population.
Why not? Because the sample size may be
too small to allow us to detect that the
population departs from the null hypothesis.
This is especially true if the population is
highly variable. To see if the sample is large
enough to detect differences that matter,
a separate calculation is conducted to
evaluate the power of the test.
Power
Suppose that a two-sample t test is being
conducted to answer the question: do two
populations have the same mean? Suppose
further that the two population means differ
by 10 units. For this situation, a power
calculation answers the question: given the
sample size we have, what is the chance that
we will obtain samples that correctly lead us
to reject the null hypothesis? The power of
the test depends on how far apart the two
population means are and on the sample
sizes. Given sample sizes of 100, it will be
easier to reject the null hypothesis if the

means are 20 units apart, and more difficult
if they are one unit apart. Given population
means that are ten units apart, it is much
easier to detect this difference with samples
of size 100 than with samples of size 25.
Concluding that the null hypothesis really
describes the population ("accepting the
null hypothesis") is reasonable only if power
calculations verify that the sample size was
large enough to ensure a high probability of
detecting a practically important difference.
Unfortunately, power calculations are dif-
ficult and not widely available in statistical
software. Cohen's book (1988) provides a
comprehensive treatment of power calcula-
tions and includes the required tables.
Type I and II Errors
Rejecting the null hypothesis when it really
does describe the population is called mak-
ing a Type I error. The probability of doing
this when the null hypothesis holds true is
called a; it is equal to the cutoff value used
to declare a sample rare, usually P = 0.05 or
0.01. Failing to reject the null hypothesis
when it does not describe the population
is called making a Type II error. The
probability of doing this, in a particular
situation and for a particular size sample, is
called ~; the power of the test under the
particulars is 1 - ~. It is not possible to
make both a Type I and a Type II error at
the same time. When the test conclusion is
"reject the null hypothesis," the concern is
"am I making a Type I error?" When the
test conclusion is "there is no evidence to
reject the null hypothesis," the concern
is "am I making a Type II error?" The
null hypothesis gets the benefit of the
doubt. That is, the data have to convince the
researcher to reject the null hypothesis.
Some books describe the null hypothesis
as "the hypothesis the researcher wants to
disprove" and the alternative hypothesis as
"the hypothesis the researcher wants to
prove." This does not cover all the situa-
tions, however. If a researcher wants to
demonstrate that two methods of making a
certain product give the same mean sensory
Statistical Methods 751
score, the statistical theory that leads to the
calculation of P values requires that "no
difference in means" be the null hypothesis.
In the end, it's the statistical theory that
determines which hypothesis is the null and
which is the alternative.
One-Tailed Tests
In many tests, such as F tests in ANOVA
and regression or x2 tests, the alternative
hypothesis is always the negation of the
null hypothesis, its logical opposite. For
example, in an ANOVA overall F test,
the null hypothesis is that the means of all
treatments are equal, and the alternative
hypothesis is that at least some of the
means differ. Other tests such as the t test
for the difference of two means, or tests
about the value of a regression coefficient,
allow the investigator more flexibility. The
investigator may specify an alternative
hypothesis that is the negation of the null;
for example, the difference of two means is
not equal to zero. Such a test is called a two-
tailed test. Or, the investigator may choose
an alternative hypothesis that specifies a
particular direction of departure from the
null hypothesis (a one-tailed test). For
example, in comparing the mean sensory
score of a new formulation with that of
the current formulation, the alternative
hypothesis of interest would be: the mean
sensory score of the new formulation is
higher than that of the current one. This
alternative reflects the practical situation:
the investigator will recommend that the
new formulation be adopted only if the null
hypothesis is rejected.
Whenever a one-tailed alternative is
used, the direction of departure from the
null hypothesis must be selected in light
of the decision being made. In principle,
the alternative hypothesis must be chosen
before the data are collected; in practice, its
justification cannot depend on the way the
sample data turned out. Converting a two-
tailed test into a one-tailed test after the fact
makes the results appear more significant
than they really are, since the P-value is
752 Source Book of Flavors
cut in half. The informed user resists this
temptation, since the real Type I error rate
is that for the two-tailed test.
The Link Between Estimation and Testing
To illustrate the relationship between
estimation and hypothesis testing, consider
two examples. First, suppose a user has
calculated a 95 percent confidence interval
for a population mean 11, and has obtained
lower and upper limits of 98 and 103. Since
one way of interpreting this interval is as the
range of mean values that could have easily
produced our data, any value in this range
would not be rejected in a hypothesis test
with a two-tailed alternative. For example,
the confidence limits indicate that a test with
the null hypothesis that 11 = 102 would
have P > 0.05, while a test with the null
hypothesis 11 = 97 would have P < 0.05.
The data do not provide enough evidence to
reject 11 = 102, but do provide evidence to
reject 11 = 97.
Another common situation is comparison
of two means, 11 1 and 112 . If the user is
interested in testing whether the two means
are equal or not, the null hypothesis of
equality of means is usually expressed as 11 1
- 112 = 0. When the 95 percent confidence
interval for 111 - 112 includes zero, for
example -1.5 to 2.5, the hypothesis that the
means are equal is not rejected for a= 0.05.
When the 95 percent confidence interval
does not include zero, for example -3 to
- 1, there is evidence that the means are not
equal.
Statistical Versus Practical Significance
Statistical significance alone may not be a
sufficient basis for action. With very large
samples, the null hypothesis will almost
always be rejected even if there is no prac-
tical difference. For example, suppose a
manufacturer of pasta sauces has developed
a new process that attempts to improve
flavor by minimizing loss of volatiles during
heat processing. The new process would
require costly modification of the existing
plant equipment. After a series of promising
plant trials, large-scale consumer taste test-
ing was used to compare sauces produced by
the new and the standard processes. If these
tests show that there is a statistically sig-
nificant improvement in taste, the manu-
facturer will still have to assess whether to
proceed with the changes, given the cost
of the processing modifications and the
business environment.
Confidence intervals summarize what the
sample tells us about the magnitude of the
difference or effect. They can help answer
the question: is the difference large enough
for us to act on?
Differences in Means
versus Population Overlap
Statistical techniques for both estimation
and testing focus on averages. Concluding
that the mean of one population is less than
the mean of another does not imply that an
individual or item from the first popula-
tion will always have a lower value than an
individual or item in the second. Both of the
pictures in Figure 18-2 are compatible with a
significant difference in population means
even though the populations overlap in
Figure 18-2b. Examination of sample
histograms, stem-and-leaf diagrams, and
a) Well separated populations
b) Overlapping populations
FIGURE 18-2. Populations with different means.

box plots can help the investigator get a feel
for the amount of population overlap.
REGRESSION
We begin with an example. How is the
residual sugar in a batch of wine affected
by characteristics of the grapes and the
fermentation process and temperature?
How accurately can we predict the residual
sugar, given the characteristics of the grapes
and the process parameters? Can we use
past data to adapt the process so that a
target residual sugar can be achieved, given
certain grape characteristics?
Regression helps answer questions like
these. In regression, a particular charac-
teristic of a product, process, or system is
singled out as the response variable Y;
we seek to understand how the response
variable, say residual sugar, changes as a
function of input characteristics, processing
method, and other conditions that are
measured by X variables. Regression also
helps us determine which X variables have
major impacts on Y. Finally, regression can
be used to predict Y given the values of the
X variables.
The Model
The linear regression model assumes that
the relationship between the mean or
expected value of Y, E(Y), and the X
variables has the form:
where the ~ terms are unknown constants
that d~scribe the relationship between the p
X vanables and the mean of Y. Given a set
of specified values for the X variables we
imagine an entire population of Y v~lues
':ith these X's. For example, such a popula-
tion of Y values could be the residual sugar
values in different batches of wine. Even
though the fermentation procedure was the
same and the grapes were from the same
Statistical Methods 753
vineyard, the resulting residual sugar levels
will not be identical due to small variations
in temperature, yeast growth, and environ-
mental and other factors. Treated as a
population, the Y values will have a mean
E(Y) sometimes denoted E(YiX's) and a
. 2
vanance cr YIX· The expression E(YIX's) is
read "E of Y given the X's" and reflects its
dependence on the X values. The variability
?f the Yvalues around their mean E(YIX's)
IS assumed to be the same for all populations
of Y values. The model invites us to con-
sider the observed response Y as a sum of a
systematic part E(YIX's) and a random,
chance variability part, E. E is sometimes
called the "error" term. In a statistical
sense, error just means individual variability
that is not predictable. Thinking of E as
Y - E(Y) leads to the assumption that the
E have mean zero. The variance of the E =
Y - E(Y) is the same as the variance of the
Y around E(Y), since c(Y) is treated as
a constant. Since cr2 y1x is assumed the same
for all X, it is often denoted simply by cr2
and called "the" variance.
This model is called linear because
each population parameter ~ multiplies a
predictor X, and the ~kXk terms are added
together. Since the linear regression model
can encompass predictors that are powers or
products of the originally measured X
variables, curved relationships and interac-
tions can be modeled. For example, the
following are linear models.
Y = + ~~x~ + ~2Xz + ~ 3X1 2
~o
+ ~4Xl + ~sX1X2 + E
log(Y) = ~o + ~~x~ + ~2Xz + E
Given a sample of X and Y values the
co~fficients ~o, ~ 1 , . . . , ~P can be esti~ated
usmg the least squares principle. The co-
efficient estimates ~ 0 , ~ 1 , . . . , ~P are chosen
so that, in the aggregate, the Y values
predicted by our fitted model
754 Source Book of Flavors
are as close to the actual observed Y values
as possible. What the least squares fitting
procedure does is choose the coefficient
estimates so that the sum of squared dif-
ferences between the observed and fitted
Y's, l: (Y- Yf, is minimized. That value of
l: (Y - Y) 2 , the sum of squared errors
(SSE) is a measure of the goodness of fit of
the regression.
The difference between the observed
response Y; and the fitted values Y i from the
regression is called the residual for the i 1h
case. It is often denoted e; ore;. The residual
gives us an idea of how far off the regression
model might be if we used it to predict the
response for a new case where we only had
the X variable values and needed to predict
the response Y.
The least squares fitting procedure forces
the average of the sample residuals, e;, to be
0. The standard deviation of the residuals, s,
is equal to the square root of:
1 ~ ' 2
[n- (p + 1)] ;~(Y;- Y;)
where p is the number of predictors in the
model. The units on s are the units of the
response variable Y.
Evaluating Model Fit: s and R2
s has three interpretations that overlap.
It measures the typical distance between
an observed Y value and the fitted value
Y, based on the case's X values. s also
estimates the standard deviation of the
Y values around their estimated means,
E(YjX's). Finally, s estimates the standard
deviation of the random terms E.
sis an important measure of the adequacy
of a regression model. It answers the ques-
tion: does the fitted regression do a good job
at predicting Y within the sample we have?
Since the units for s are the units of the
response Y, investigators can (and should!)
apply their subject-matter knowledge to
determine whether s is small enough to
indicate that the fit is useful in practice.
R 2 is related to s. R 2 answers the ques-
tion: how much better do we do if we
predict the Yvalues using the X variables in
the fitted regression, compared to just using
Y, the sample average of the Y values?
which is what we would do if we thought the
X variables were of no use. Thus, R 2 does
not directly assess prediction accuracy.
Since R 2 is always between 0 and 1, it can be
interpreted as a percent; the percent of the
variability of Y that is accounted for or
"explained" by the regression. A modifica-
tion of R 2 called adjusted R 2 is useful for
comparing models. It is discussed later.
However, a high R 2 or adjusted R 2 alone is
not enough to guarantee accurate prediction.
Checking the Model Assumptions
Since confidence intervals, prediction
intervals and hypothesis tests will have
the correct long-run performance only if
the model assumptions are approximately
satisfied, assumption checking is a crucial
part of regression analysis. Fitting the
regression model to the data, estimating the
coefficients ~ 0 , ~ 1 , . . . , ~P' and assessing the
goodness of fit using s are just the beginning
of a regression analysis.
The practical issue in assumption check-
ing is: Is there reason to believe that our
data are so inconsistent with the standard
model assumptions that our conclusions
are in jeopardy? The most productive
approaches to assumption checking rely on
interpreting graphical displays. Since the
regression assumptions can all be stated in
terms of E, the residuals (e, the sample
equivalent of E) are used for assumption
checking. The main tool is a scatterplot
of the studentized residuals (also called
standardized residuals) against the fitted
values Y. This plot is used to check in-
dependence, nonlinearity, and constant
variance.
Since the residuals have mean zero
(the least squares fitting procedure forces
 Statistical Methods 755

2
X
X X X
X X X X XX
Studentized X X
Residuals 0
X X X Fitted Values y
XX X X
XX X
X X X
X X

-2

a) Non-linearity or lack of independence

X
2 X X
X
X X X
X X X
X X X
X X X X X X
Studentized X X
X
Residuals 0 X X X X X X
Fitted Values y
X XX X X X X X
X X X X
X X
X
X
X X
-2

b) Non-constant variance

FIGURE 18-3. Residual plots indicating assumption violations.

this), the spread of the residuals above and
below zero is of interest. If the form of the
regression model is correctly specified,
the observed points should be distributed
randomly above and below and fitted sur-
face. Clumps of residuals above and below
zero indicate that the form of the regression
relationship is mis-specified, that there is
nonlinearity or curvature (Figure 18-3a). If
the data have been collected on the same
individuals or objects over time, clumping
of the residuals above and below zero is
usually diagnosed as lack of independence.
Since the individual variability terms are
assumed to have constant variance the
vertical spread of the residuals should be the
same for all fitted values of Y. The most
common violation of this assumption is for
the variance of the residuals to be larger
for larger responses, for the spread of the
residuals to be increasing as we move across
the plot from low Y to higher Y (Figure 18-
3b). If this is the case, changing the scale
of the response variables, for example by
taking logs, may lead to a model that better
satisfies the constant variance assumption.
The residual versus fitted plot also calls
our attention to points with unusual Y
values, points isolated from others in the
horizontal direction that represent cases
with unusual combinations of X values
cr' (Figure 18-4a). These points may be highly
influential, that is, the fitted regression
coefficients may change by a relatively large
756 Source Book of Flavors

Studentized
Residuals X *
0 Fitted Values Y
X X

X X

·2

a) Possible influence point (indicated by *)

*
2
X
Studentized X
X X
Residuals X
0 Fitted Values y
X
X

·2

b) Outlier (indicated by *)

FIGURE 18-4. Residual plots illustrating unusual data points.

amount if these points are removed from the
sample. (Influential points are also called
leverage points, from the geometry of
Figure 18-4a.) In investigating such points,
the researcher may uncover an error in data
entry or an anomaly in the experimental
situation that would warrant discarding
the observation. Or, the researcher might
decide that the unusual combination of X
values does not represent the situation for
which the model is being developed, and
therefore refit the regression without it. If
the unusual combination of X values really
is within the domain of interest, then the
gap in the set of X values should be filled in
so that the results are no longer sensitive to
a single point.
Finally, the residual versus fitted plot
calls our attention to points with unusually
large positive or negative residuals. The
studentized residuals are scaled to have a
variance of one. While the distribution is
not exactly normal, it is symmetrical and
shaped so that approximately 95 percent of
the studentized residuals are between -2
and +2. A studentized residual much out-
side of this range is considered a potential
outlier (Figure 18-4b). Much more than 5
percent of the studentized residuals outside
of -2 and +2 is an indication that the dis-
tribution of the e may not satisfy the usual
assumptions.
The final assumption to be checked is the
approximate normality of the e. Strictly
speaking, the normality assumption is not
required by the least squares fitting pro-

cedure, but all the test and confidence
interval procedures that are based on t and
F distributions do require approximate
normality. A normal probability plot, or a
rankit plot, is used to check this assumption.
The plot utilizes a special scale (normal
scores) constructed so that the plot of the
residuals (or studentized residuals) against
the normal scores is a straight line if the c
are normally distributed. Departures from
normality are reflected by S shapes or
bends. A test based on the correlation of the
residuals and the normal scores can be used
to supplement the normal probability plot
(Neter, Wasserman and Kutner 1990, 126-
127; Johnson and Wichern 1988, 150-151).
Since the normal probability plot can be a
straight line even if independence and/or
constant variance are violated, the residual
versus fitted plot should be examined first.
Interpreting Regression Coefficients
The coefficient ~ on a continuous X variable
tells us how the expected value of the
response variable Y changes, if we change
the value of this X variable by one unit while
keeping all the other X variables fixed. The
units on the coefficient are Y per X. The
magnitude and even the sign of a regression
coefficient depend on the other X variables
included in the model.
How much information do the data give
us about the value of the coefficient? How
well have we pinned down the population
coefficient? How much uncertainty is there?
The standard error of the coefficient answers
this question. The user can calculate con-
fidence intervals for the population co-
efficient using the standard error and the
t distribution with degrees of freedom,
depending on the sample size n and the
number of predictors p. Provided the
regression assumptions are roughly satisfied,
formal tests about the value of the popula-
tion slope can also be carried out, again
using the t distribution with n - (p + 1)
degress of freedom. Statistical computer
packages routinely print the t statistics and P
Statistical Methods 757
values for each coefficient. For each X
variable, these answer the question: Do the
data provide evidence that the slope on this
variable is not zero in the population given
the other variables in the model? (The P
value is calculated for a two-tailed alterna-
tive.) Two equivalent ways of interpreting
the printed t tests are: Does adding this X
variable to the model significantly improve
the fit, given the other variables already in
the model? Do the data provide evidence
that there is a relationship between the
response variable and this X variable, given
that the effects of the other X variables in
the model have been taken into account?
Predicted Values and Prediction Intervals
There are two interpretations of a fitted
response, Y, given specified X values. It is
the predicted value of the response for an
individual case. It is also an estimate of the
mean E(Y) for the population with the
specified X variables.
This dual interpretation is important
when assessing the amount of uncertainty in
the prediction or mean estimate. The key
thing to remember is that it is more difficult
to predict for an individual than to estimate
the mean of a population, so the standard
error that summarizes the uncertainty
when predicting an individual's response is
larger. Different names are used for the
two standard errors. The interval estimates
calculated for the two situations are usually
called prediction intervals for individuals
and confidence intervals for population
means. The interpretations of the intervals
are parallel. (See the previous section on
estimation and confidence intervals.)
The width of both the confidence inter-
vals and prediction intervals varies with the
particular X values. The standard error
estimates for both situations are smaller for
X values that are close to the averages of the
X values used to fit the regression; there is
more uncertainty about the Y value for a
case or a population of cases whose X values
are near or beyond the boundaries of the X
758 Source Book of Flavors
values used to fit the regression. Because
getting useful prediction intervals is much
harder than detecting relationships between
Y and X, prediction intervals can be wide,
even if the standard deviation of the residuals
s is small, the R-squared is high, and all
the variables in the model have slopes that
are highly significant. Therefore, the user
cannot rely only on the usual goodness of
fit statistics; when prediction is the goal,
prediction intervals for several settings of X
variables must be examined directly. How
narrow the prediction intervals must be
to be useful in practice depends on the par-
ticular scientific context.
Statistical computer packages do not
fully meet the user's needs for prediction
intervals. If a package prints only one
standard error and interval, it is the one for
estimating the population mean, which is
smaller than the interval needed for an
individual case. It is possible to calculate the
prediction interval for an individual from
the standard error for the population mean;
details are given by Neter, Wasserman
and Kutner (1990, 81-83, 246). In some
programs, prediction is accomplished by
inserting cases into the dataset being used to
estimate the regression, with their Y values
coded as missing.
Indicator Variables in Regression:
Comparing Groups
The linear regression model can accom-
modate X variables that indicate group
membership. Our discussion uses binary
0-1 variables to do this; there are other
equivalent coding schemes to incorporate
such information (Neter, Wasserman and
Kutner 1990, 378-379, 555-560, 712- 716).
Models that include both 0-1 indicator
variables and continuous variables can be
used to study how the relationship between
the response variable and the continuous X
variable varies across groups. They can also
be used to compare the mean responses
across groups after adjusting for other
factors (represented by the continuous
X variables). Models with only indicator
variables can be used to fit analysis of
variance models.
To illustrate the use and interpretation of
indicator variables in regression, suppose
that a researcher wishes to study consumer
liking of a jam prepared by two methods,
where sweetness of the fruit being used may
vary greatly. In this case, the sweetness
could be considered a co-variate. Because of
the differences in raw materials, a simple
two-independent group t test is not an
appropriate way to compare the consumer
response to jams prepared by the two
methods. While a paired t test could be
used, a regression analysis with the sweet-
ness of the fruit as an X variable can yield an
understanding of how sweetness affects
liking, in addition to providing a sensi-
tive comparison of the two preparation
methods. In this situation, a continuous
measure of the liking score is the Yvariable,
a continuous measure of the sweetness
of the fruit is the X variable, and a
0-1 indicator variable distinguishes the
methods. In an analysis of such data, the
researcher would fit three different regres-
sion models and compare their fits. A model
that fits separate lines to each method has
three explanatory variables: the sweetness
X, the method indicator and the product of
these two. The coefficient on the cross-
product variable represents the difference
between the slopes of the two methods; its t
test indicates whether or not the separate
line model must be used. If the difference
between the slopes is not significantly dif-
ferent from zero, parallel lines fit the data
just as well. A model that fits parallel lines
for the two methods has two explanatory
variables: the sweetness X and the method
indicator. The coefficient on the methods
indicator variable represents the distance
between the two lines; its t test indicates
whether or not the lines are parallel or are
actually identical. A model that fits the
same line to both methods has just one
explanatory variable: the sweetness X.
When there are more than two groups,

more than one indicator variable must be
used. The separate, parallel and identical
line models can be compared by a series ofF
tests. Details are given in Neter, Wasserman
and Kutner (1990, sections 10.1-10.4);
Weisberg (1985, sections 7.2-7.4); Draper
and Smith (1981, section 5.4).
Building, Comparing, and Selecting Models
Most statistical treatments of model-
building take the perspective that com-
plicated models do not reflect the major,
persistent features of the underlying system
or population. Models with a large number
of variables may give an excellent fit on the
dataset used to develop them, yet perform
poorly when applied more widely. "Occam's
razor" is the modeler's working view of
reality: Small models are more likely to give
us a grasp of the truth. Several criteria
have been developed for choosing among
regression models. Algorithms that work
with these criteria do not incorporate any
assumption checking.
The summary statistics s and an adjusted
version of R-squared are useful in compar-
ing models that are fit to the same data.
Even though the sum of squared errors
always decreases when variables are added
to the model, s may increase. If this happens,
it is a clear indication that the model is
becoming too complicated given the avail-
able data. Since R-squared is a function of
the sum of squared errors, R-squared always
increases when variables are added to the
model. An adjusted R-squared based on the
mean square for error is more useful in
model selection, since it only increases if the
added variables lead to a reduction in s, thus
indicating an improvement in prediction.
Maximizing adjusted R-squared is
equivalent to minimizing s or the mean
squared error (MSE), the variance of the
residuals. The resulting model may contain
variables whose slopes do not have sig-
nificant t statistics, since a variable leads
to a reduction in MSE and an increase in
adjusted R-squared if the absolute value
Statistical Methods 759
of its t statistic is greater than one. For
example, a variable whose slope had a t
ratio of 1.6 would lead to a reduction of
MSE even though it has a P value greater
than 10 percent. If the regression model is
being used to study the explanatory role of
the X variables rather than to predict, the
investigator may wish to delete some of the
variables with t statistics between one and
two, so that all variables in the model have
P values less than 0.05.
The mean squared error reflects the
in-sample performance of the model, so it
underestimates the aggregate prediction
error for new cases. In developing models
for prediction, the user may wish to assess
the out-of-sample performance of the
models. Two criteria that employ an out-of-
sample approach are PRESS and Mallows'
CP. They are discussed by Neter, Wasserman
and Kutner (1990, section 12.3), Weisberg
(1985, sections 8.8 and 9.1), and Draper and
Smith (1981, sections 6.1 and 6.8).
Comparing values of s, MSE, adjusted R-
squared, and Mallows' CP is an informal,
judgmental process; formal hypothesis tests
for comparing these statistics are not avail-
able. These statistics are flexible enough
that they can be compared whether or not
the variables in the smaller model are a
subset of the variables in the larger model.
In practice, it is often the case that
several models have equivalent fit. If so,
the investigator may choose the set of
X variables that are most plausible on
scientific grounds. As indicated earlier,
the width of prediction intervals should be
examined directly when prediction is the
goal.
In the special case where two nested
models are being compared, where the
variables in the smaller model are a subset
of the variables in the larger, formal tests
are available to supplement the comparison
of summary measures. The smaller model is
called the restricted model and the larger
model is called the full model; these are
relative terms. An F test can be used to
answer the question: do the data provide
 760 Source Book of Flavors
evidence that the full model is significantly
better than the restricted one? When the
two models differ by one X variable, the t
test for that variable in the fuller model is
equivalent to the F test: the F statistic is the
square of the t statistic, the P value is the
same (Neter, Wasserman, and Kutner 1990,
279-281; Weisberg 1985, 50-51; Draper
and Smith 1981, 102).
Several algorithms that attempt to
automate model building and selection
are available. The most helpful minimize
MSE/maximize adjusted R-squared. Older
algorithms designed when less computer
power was available incrementally build
models by adding or removing one variable
at a time, using tor F statistics. (It is helpful
to remember that an F value of 4 cor-
responds to at value of ±2.)
Backward elimination algorithms begin
with all the candidate variables in the
model. If there are variables with low t
statistics, the one with the smallest t statistic
(in absolute value) is removed. The model is
refit, and the examination of t statistics
repeated. The algorithm continues until all
the variables in the model have significant
t statistics. Some versions of backward
elimination examine t statistics for variables
removed early in the process, to decide
whether they should be added back to the
model.
Forward stepwise algorithms begin with
no variables in the model, asking the ques-
tion: If I am allowed to use one X variable
to predict Y, which one-variable model
should I choose, if any? The one-predictor
model with the biggest t statistic is chosen,
unless none of them have significant slopes.
The algorithm then asks the question: Given
the X variable I have selected, which X
variable, if any, is it most helpful to add next
to the model? Models with two predictors
(the variable selected at step one and
each of the other X variables in turn) are
examined. The variable with the biggest t
statistic is added, provided it is significant.
The algorithm continues until no more X
variables can be added. Some versions of
forward stepwise remove variables added
early in the process if they later become
insignificant.
Options that allow the user to force
variables into the model are available with
both backward and forward procedures.
This allows the investigator to incorporate
knowledge of the scientific context. Because
of the one-at-a-time nature of both algo-
rithms, there is no guarantee that the final
model is "best," or the "best" with the
given number of X variables.
No automated algorithm can replace
the investigator, who must assess models
for plausibility and can identify groups of
variables that are of scientific interest.
When several models fit about equally well,
the model that is easiest to interpret may
be selected. The scientist may choose to
include certain variables in some of the
models for the purpose of testing and
comparing theories. The process of model-
building works best when it is interactive
and iterative, and when the aim is to find
a few models for further investigation and
scientific validation.
ANALYSIS OF VARIANCE
Introduction
The collection of statistical methods called
analysis of variance (ANOVA) devel-
oped out of agricultural experimentation.
ANOVA incorporates a philosophy of
designed experiments and experimental
control; ways of conducting experiments
and ways of analyzing the resulting data
are so closely linked that courses and
books on ANOVA often include "experi-
mental design" or "design of experiments"
in their titles. Experiments in which
the "treatments" (e.g., different product
formulations) are created by varying the
levels of several factors are said to have a
factorial design. ANOVA techniques have
become common not only in experimental
sciences and engineering, but also in fields
that compare populations through observa-

tional studies. Different areas of applica-
tion have developed distinct vocabularies.
Product research and development use
language from chemical engineering and
sensory analysis uses language from psy-
chology, so people from these two areas
may not realize that they are using the same
design.
As an example of a controlled experiment,
suppose an investigator conducts a study
to compare the appeal of three different
savory flavors and to investigate how they
are perceived with and without monosodium
glutamate (MSG). The researcher may want
to determine which of the six treatment
combinations is the most preferred, or
may need to recommend which of the
flavors would perform best in an MSG-free
product.
As an example of an observational study,
suppose a researcher wants to study how the
liking of a frozen breakfast pastry varies
among men and women of various age
groups, such as 18-25 years, 26-35 years,
36-50 years, 51-65 years, and over 65
years. In this study, gender and age category
are factors, but individuals are sampled
from these categories rather than assigned
to them.
Despite its name, ANOVA focuses on
comparisons of means of continuous vari-
ables. The "variance" in "analysis of
variance" refers to comparisons between
the variance in means across groups and the
variance about the mean within groups. If
the data were collected from a controlled
experiment, ANOVA provides tests to
answer the questions: does changing this
factor result in a significant change in the
mean response? Do changes in these two
factors affect the mean response "inde-
pendently," that is, in an additive fashion,
or is there an interaction between the two
factors? For example, there may be interac-
tion between MSG level and type of savory
flavor. If the ANOV A indicates that there
are some differences between means, that is
there are some factor effects, confidence
intervals indicate which means differ, thus
Statistical Methods 761
providing guidance for operational deci-
sions. In adapting ANOVA to observational
studies, the language of causation must be
modified. ANOVA now answers questions
such as: do the data provide evidence that a
difference in means is associated with dif-
ferent values of this factor?
One-Way ANOVA: OveraliFTest
and Multiple Comparisons
When only one factor is being manipulated
in an experiment, or when the investigator
thinks there is only one factor distinguishing
the groups in an observational study, a
linear model of the following form is used:
The observed response Yii for the jth in-
dividual in the ith group is modeled as the
sum of an overall mean J.l, an "adjustment"
for the ith group, and an individual vari-
ability term eii· The mean of the ith group,
J.li, is equal to J.l + ai. For each group,
the sample average is an estimate of J.li· The
average of all the responses in the study is
an estimate of the overall mean J.l. The
differences between the group averages and
the overall average estimate the ai terms.
The eii represents the difference between
individual j's response and the mean of
group i. The eii terms play the same role as
they do in regression: They are assumed to
be independent both within and across
groups, to have mean zero, and to have the
same variance in each group. The use of F
and t distributions assumes that the eii have
a normal distribution. The ANOVA overall
F test uses the sample estimates of the a/s
and the ei/s to assess whether there is
evidence for differences among the means
of the populations being studied.
As an illustration, consider an experi-
ment in which panelists were asked to assess
the intensity of light-activated flavor devel-
oped in milk samples exposed to different
intensities of fluorescent light for two hours
(Leland 1986). Nine replications of the
762 Source Book of Flavors
TABLE 18-1. Average Scores for Activated Flavor
Intensity
Light Average
Treatment Flavor Standard
Group (ft-c) Intensity Deviation
A 0 1.7" 1.6
B 150 2.7•b
2.2
c 300 3.5b 2.3
D 450 7.(1' 2.1
Source: Leland 1986.
abc Means with the same superscript do not differ significantly
by the Tukey Multiple Comparison procedure; a = 0.05.
treatments were carried out. Each set of
samples was rated by four or five panelists
using a ten-em visual analog scale. Since the
overall F test for the composite average
intensity scores given in Table 18-1 is highly
significant (F = 55.55; df = 3,172; P <
0.001), we conclude there are some dif-
ferences among the group means.
When the overall F test indicates that the
population means are not all the same, the
researcher will then want to know which
means are different, and by how much they
differ. In some contexts, the investigator
needs to determine which treatment or
treatments are the best. These questions
are answered by multiple comparison
procedures. These procedures can be dis-
cussed either as testing procedures or as
ways of finding confidence intervals. The
presentation here emphasizes confidence
intervals.
Why can't the differences between pairs
of treatments or groups simply be explored
by a series of two-independent-sample t
tests? There are two reasons why a series of
t tests is not advisable. First, the pooled
estimate of variance from all the groups is
much more precise than using the data from
only two groups at a time. Second, and
more importantly, there are difficulties in
the interpretation of a, the cutoff level for
the P value, when a large number of tests
are carried out. If 100 tests are done, each
with a level of 0.05, about 5 of these tests
will result in rejection of the null hypothesis,
even when no differences are present. In an
experiment with seven treatments, there are
21 pairs of means to compare, so on the
average, one rejection of the null hypothesis
will be incorrect. The probability that none
of the rejections of the null hypothesis
are incorrect is (.95) 21 = 0.34. Thus, the
probability of at least one incorrect rejec-
tion of the null hypothesis becomes 0.66
instead of the nominal 0.05.
To deal with this second difficulty, most
multiple comparison procedures take into
account the number of tests being made,
maintaining a chosen a level such as 5 per-
cent or 10 percent for the whole set or
family of tests or confidence intervals. Such
a family (or experiment-wise) a is inter-
preted as follows. If a = 0.05, then in 95
percent of the studies analyzed, none of the
tests will reject their null hypothesis in-
correctly. In the other 5 percent of the
studies, one or more of the rejections of the
null hypothesis will be incorrect. Equi-
valently, in 95 percent of the studies, all the
confidence intervals will cover the true
population quantities; in the other 5 percent,
one or more of the confidence intervals will
not include the true population quantity.
Most multiple comparison procedures keep
the family a at the specified level by increa-
sing the width of each confidence interval
around the averages, or differences of
averages.
As an example, consider an experiment
in which intensity of mustard flavor was
rated for five brands of mustard. Suppose
that in brands A, D, and E the mustard seed
was very finely ground, while in brands B
and C it was coarsely ground. Suppose that
the overall F test gives strong evidence of
overall differences in mean mustard flavor
intensity. There are several questions that
might be of interest. One researcher might
want to know exactly which mustards were
rated differently, which would require
comparing ten pairs of mustards. Another
investigator might focus on the differences
in the grind of the mustard seeds, so that
comparing A, D, E as a group against Band
C as a group might be important. Then the

investigator might compare the following
pairs: A and D, A and E, D and E, Band
C. This would look at differences between
mustards within the two grind groups.
A wide variety of multiple comparison
procedures are available, allowing different
families of differences and comparisons
among the group means to be examined.
For example, the Tukey procedure com-
pares all pairs of means, while Dunnett's
procedure compares each treatment with a
control. The procedures make different
trade-offs between the power to detect dif-
ferences and the risk of declaring a difference
when none is present in the population. For
example, Duncan's multiple range pro-
cedure and the Newman Keuls procedure
have higher power than the Tukey pro-
cedure for examining all pairwise dif-
ferences, but do not hold the a level fixed at
5 or 10 percent. Since the theory underlying
multiple comparison procedures often
requires approximations, the best procedure
to use may depend not only on the type
of differences the researcher wishes to
examine, but also on the number of groups
and the sample size. A few of the most
commonly used procedures are outlined
here. For a comprehensive survey, the
reader is referred to Miller (1981). Good
introductory chapters are found in Neter,
Wasserman and Kutner (1990, Chapter 15)
and Steel and Torrie (1980, Chapter 8).
A convenient way of summarizing mul-
tiple comparisons for all pairs is to arrange
the groups in increasing order, connecting
those groups whose means do not differ
significantly with a common underline (Fig.
18-5). Such multiple comparison results can
also be indicated in a table of averages by
the use of common superscripts, as in Table
18-1.
The Tukey procedure is designed
specifically for the family of all pairwise dif-
ferences of means. The procedure assumes
that the constant variance assumption holds.
It also assumes that the design is balanced,
and that the number of samples in each
group is the same. Under these assumptions,
Statistical Methods 763
A B C D
FIGURE 18-5. Summary of multiple comparisons
for activated flavor.
the confidence intervals produced by this
procedure are the shortest possible for the
family of all pairwise comparisons of means,
given a fixed family confidence coefficient.
A modification of this procedure, called
the Tukey-Kramer procedure, adjusts for
unequal group sizes (Neter, Wasserman and
Kutner 1990, 583-584).
As an illustration of the Tukey pro-
cedure, we continue with the light-activated
flavor example from before. The overall F
test indicated that there were differences
between the treatment groups. To deter-
mine exactly which means differ, the Tukey
procedure with a= .05 was used for follow-
up multiple comparisons (Table 18-1).
Group D is significantly different from the
other treatment groups. Groups A and C
differ significantly, but group B is not clearly
distinguished from either group A or group
C. Even though the F test was highly sig-
nificant, not all the groups are different.
When the user has identified a small set
of differences and/or other linear combina-
tions of the group means, a procedure
based on the Bonferroni inequality (Neter,
Wasserman and Kutner 1990, Section 15.5;
Johnson and Wichern 1988, 188-190; Miller
1981, Section 3 of Chapter 2) can be used.
For example, the second investigator in
the mustard study has identified five com-
parisons of interest, rather than the ten
pairwise differences. The Bonferroni pro-
cedure requires that the comparisons being
made are based on features of the treat-
ments (a priori comparisons). Unlike the
Tukey procedure (above) and the Scheffe
procedure (next), the Bonferroni procedure
cannot encompass comparisons that become
interesting in light of patterns observed in
the data. With the Bonferroni procedure the
statements can be any linear combinations
of group means-single means, sums or
averages of several means, linear contrasts
764 Source Book of Flavors
of means (combinations of means whose
coefficients sum to zero), as well as dif-
ferences of two means. For example, the
mean flavor intensity of mustards with very
fine grinds is the linear combination 11311A
+ 11311n + 11311E· The two grinds of
mustard seeds can be compared by the con-
trast 11311A + 11311n + 11311E - 11211B -
11211c· What this contrast does is form an
average of the means of mustards A, D, and
E and an average of mustards B and C,
and then take the difference. Another
advantage of this procedure is that the
assumption of constant variance can be
relaxed, adapting the procedure for the
comparison of two means (Snedecor and
Cochran 1980, section 6.11). The heart of
the Bonferroni procedure is the Bonferroni
inequality: If there are s statements in the
family, using a/s as the Type I error rate for
each individual statement will guarantee
that the overall family Type I error rate is
less than a. The t distribution is used with
the modified Type I error rates. When s is
large, the Type I error rate is actually much
less than a. Roughly speaking, if there are
more statements in the family than the
number of groups in the experiment, the
Bonferroni procedure becomes extremely
conservative. If the comparisons are all
differences of means or the contrasts, and
if constant variance can be assumed, the
Scheffe procedure may give shorter inter-
vals than the Bonferroni procedure. When
both of these procedures are applicable, the
one that gives the shorter intervals should
be used.
The Scheffe procedure focuses on linear
contrasts. These include differences of two
means as a special case. Since the Scheffe
procedure allows for an infinite number of
contrasts, it produces wider intervals than
the Bonferroni procedure if there are only a
few contrasts of interest. A limitation of
the Scheffe procedure is that it requires
the assumption of constant variance. An
advantage of the Scheffe procedure is its
ability to encompass contrasts that arise
from patterns observed in the data. For
example, if the user notices that the sample
averages for treatments 1, 2, and 4 are
similar and the average for group 3 is very
different, the Scheffe procedure can be used
to assess whether this pattern holds by test-
ing whether the following contrast is equal
to zero: 113 - 113111 - 11311z - 113114·
Two-way ANOV A: Interaction
Experiments or studies that investigate
the effect of a single factor at a time are
often not realistic or efficient. In addition,
the possibility of interaction between two
factors makes more complex experiments
necessary. For example, in the savory
flavor with and without MSG experiment
described in the introduction, the flavor
most liked when MSG is not included may
be different than the flavor most liked when
MSG is included. The effect of adding MSG
may vary, depending on which savory flavor
is used.
The linear model for the two-factor
experiment is:
The subscripts i and j denote the different
settings of the factor levels. In the example,
i = 1, 2, or 3 could index the 3 different
savory flavors and j = 1 or 2 could index
MSG absent or present at a specified level.
Individual samples within each flavor-MSG
level combination are indexed by k. In a
balanced design, the number of samples of
each treatment combination would be the
same, that is, k = 1, ... , n for all (i, j).
This linear model expresses the observed
responses as the sum of terms for the MSG
and savory factors and interactions. Y;jk
denotes the observed response (liking score)
and 11 represents an overall mean. The a;
and ~j terms represent increases or de-
creases in the mean associated with the
various levels of the savory and MSG factors,
and the (a~);j terms represent the interac-
tion between them. All of these are popula-
tion parameters (unknown constants) that
 Statistical Methods 765

together add up to the mean for the (ij)th TABLE 18-2. Average Overall Liking Scores for
group. The last term E;jk represents the Savory Flavor
difference between the individual k's Flavor
reponse and the means. The random E;jk
terms play exactly the same role as they MSG Flavor A FlavorB FlavorC
do in regression: They are assumed to be Absent 47 54 76
independent both within and across groups, Present 92 88 83
to have mean zero, and to have the same
variance in each group. The use ofF and t
distributions assumes that the random E;jk
terms have a normal distribution. two interaction plots for the MSG example,
The first step in analyzing such data is to with the treatment averages (Table 18-2)
study the pattern of the treatment averages. plotted in two different ways. In these
Plots of averages called interaction plots are plots, the vertical scale is the overall liking
a useful way to do this. Figure 18-6 shows score, while the horizontal scale is arbitrary
(since the factors are considered nominal).
There are two important questions to ask of
100 any interaction plot: Are the profile lines
parallel? If they are not parallel, do they
90 cross? Profile lines that are not parallel
indicate interaction. When the profiles in an
Overall 80
interaction plot cross, the interaction is
Liking called disordinal. The plots in Figure 18-6a
70
indicate that there is interaction between
60
NoMSG MSG and flavor. The profile for MSG is
higher than that for no MSG, that is, MSG
50 always enhanced the flavor liking, but
by varying amounts. In Figure 18-6b the
40 profiles for the flavors cross, indicating
A 8 c
disordinal interaction. With the addition of
A. Flavor MSG, flavor A is the most liked, whereas
without MSG it is the least liked. Without
MSG, flavor B is more appealing than flavor
100 A, but the addition of MSG reverses this
ranking.
90
There is a formal F test for interaction.
The null hypothesis is that there is no
80
interaction, that all the (a~);j terms in the
Overall
model are zero, the profiles for the popula-
70
Liking tion means are parallel. If the data do not
60
provide enough evidence to reject the null
hypothesis, but the profiles in the interac-
50 Flavor A tion plots are not parallel, there is either a
very large variance or a lack of power.
40 If there is interaction, especially if its
Absent Present presence is confirmed by the F test, then
B. MSG we know that both factors matter. To inves-
FIGURE 18-6. Interaction plots for savory flavor tigate the treatment differences more fully
example. and to determine the best treatments,
766 Source Book of Flavors
multiple comparison procedures can be used
with the treatment averages. In doing this,
the two-way experiment is handled as a one-
way experiment, with some structure to the
treatments. In the savory flavors example,
the user may wish to compare the three
MSG treatments with each other and the
three MSG-free treatments with each other
(six pairwise differences), and to compare
the MSG and MSG-free versions of each
flavor (three more pairwise differences).
These nine structural comparisons are a
smaller family than the fifteen possible
comparisons in the Tukey family of all
pairwise differences. In this situation, the
confidence intervals given by the Bonferroni
or Scheffe procedure may be shorter than
those given by the Tukey procedure. If,
however, the investigator wishes to examine
all possible pairs to find the best of the six
treatments, the Tukey procedure may be
the appropriate one. As discussed in the
previous section, the procedure that gives
the shortest intervals should be used.
If there is no interaction between two
factors, A and B, then the differences in
response associated with the changes in the
setting of factor A are the same at all set-
tings of factor B, and vice versa. In this case,
the effect of each factor can be analyzed
separately. Here, the linear model
Y;jk = Jl + a; + ~j + f.;jk
describes the relationship between the mean
and the factor levels. In contrast to the
general two-way model, changing the set-
ting of factor A is reflected only in the a;
term since there is no interaction term, (a~)ij·
The F test for factor A answers the ques-
tion: Is there evidence that the different
levels of factor A lead to different mean
responses? The interpretation of the F test
for factor B and the ~j terms are parallel
to this. If one or both of these main effect
tests are significant, they are followed up
by multiple comparisons, using the factor
averages. Neter, Wasserman and Kutner
(1990) discuss this in Chapter 19.
8 RavorA
Overall
6
Liking
RavorB
Sucrose Aspartame
Sweetener
FIGURE 18-7. Disordinal interaction between flavor
and sweetener type.
If the interaction F test is significant, then
both factors have an important effect on
response, even if one or both of the main
effect F tests are not significant. The interac-
tion test and the interaction plot should
always be examined first. To see why, con-
sider Figure 18-7, where there is disordinal
interaction. The main effect test will indicate
no difference between the two flavors
because the averaging across sweetener
type obscures the reversal of preference.
However, it is clear that the user, far from
being indifferent, will want to select flavor
A for a diet beverage and flavor B for a
sucrose-sweetened product.
The terms in the linear model can be
estimated from various averages: the aver-
ages for each treatment combination, the
averages for each level of each factor
(averaging across all levels of the other)
and the average of all the observations in
the study. The model terms can also be esti-
mated from coefficients in regressions with
indicator variables; this method is especially
useful when the number of observations is
not the same for all treatments/groups.
Fixed and Random Effects
Factors in ANOVA models can be viewed
from two different perspectives, depending
on the scope of the inference required.
Whether a factor is treated as fixed or ran-

dam affects the way F ratios are calculated,
although the linear model itself looks
the same. In a fixed effects model, the
user wants to compare several treatment
combinations and select one of them for
future use. Examples of factors that would
be treated as fixed are selection of one of
three manufacturing processes and choice of
vegetable oil supplier. In a random effects
model, the factor levels included in the
study are viewed as a sample from a popula-
tion. Examples of factors that are treated
as random are: subjects or judges, stores
selected from a supermarket chain, lots
sampled from a production process. Since
the user will face different treatment levels
(judges, stores) in the future, inference is
needed about a whole population of factor
levels and not just the ones included in
the study. Mixed models, in which some
factors are random and others are fixed, are
possible. Models with all factors fixed,
all factors random, and mixed models are
sometimes referred to respectively as
models I, II, or Ill.
Factors
The factors that are used to construct
experimental treatments or to characterize
the groups in an observational study may be
nominal, ordinal, or selected levels of a
continuous variable, such as cooking tem-
perature or amount of sweetener. When the
factors are selected levels of a continuous
variable, both regression and ANOVA
should be used to analyze the data. An
advantage of the ANOVA model is that
it does not require that the relationship
between the response and the factor levels
have a simple smooth structure; it only
assumes that the treatment means may
differ. If, however, the relationship does
have a simple smooth structure, regression
goes further by modelling the differences
among the means as a simple function of
the factor levels. (Regression is also more
flexible than pre-computer ANOVA tech-
niques using contrasts to explore continuous
Statistical Methods 767
explanatory variables.) An easy way to look
for simple smooth structure in a one-way
ANOVA is to plot the group means against
the values of the continuous X variable.
Regression also allows us to predict the
response at factor settings not included in
the study.
Assumption Checking in ANOVA
When the number of individuals sampled
from each group is the same, that is, when
the design is balanced, the F test and t
test are robust against violations of both
the constant variance assumption and the
normality assumption. In other words, the P
values turn out to be approximately correct,
even if these assumptions are not satisfied.
Because of this robustness, the user should
aim for balanced designs. Not much is
known about the robustness of multiple
comparison procedures. If the constant
variance assumption is violated, the pooled
variance is not representative. In practice
then, the most important assumption to
check is constant variance.
Residual versus fitted plots are the main
tool for checking the model assumptions.
The E;jk terms are assumed to be indepen-
dent and to have constant variance across
treatment combinations, just as in regres-
sion. In general, the fitted values in ANOVA
are the treatment averages, and the residuals
are the differences between the observed
responses and the treatment averages.
When a simpler model (one with some
terms omitted) fits the data just as well as
the full model, fitted values and residuals
from that model should also be examined.
Since there is only one fitted value for
each treatment group, points in the residual
versus fitted plot lie on vertical strips. With
this exception, the interpretation is the same
as in regression. It can also be helpful to
plot the residuals against the order in which
the data were collected, or against other
variables that may influence the response.
Variables such as these, which are not
included in the study but are of concern
768 Source Book of Flavors

in the assumption checking, are called The pattern of interpretation outlined in

"lurking variables." the two-way ANOVA section extends to
There are also formal tests for the equality models with more than two factors: The
of variance across treatment groups, such higher-order interactions should be looked
as Bartlett's test (Neter, Wasserman and at first. Interaction plots for three-way
Kutner 1990, Section 16.2). However, this ANOVA can be constructed by making
test is not as helpful as the residual plot two-way interaction plots for each level
because it does not have good power if the of the third factor. When higher-order
treatment group sizes are small (as is typical interactions are present, two-way interac-
in ANOVA). A Bartlett's test that fails to tion F tests and main effect F tests may not
reject the null hypothesis of equality of be significant, analogous to the behavior
variance is not much reassurance. Another of the main effect tests discussed in the
difficulty with Bartlett's test is that it assumes previous section. Discussions with examples
normality and is sensitive to this assump- are given by Neter, Wasserman and Kutner
tion, so a rejection of the null hypothesis (1990, Chapter 22) and Box, Hunter, and
may indicate a departure from normality Hunter (1978, Chapters 10 and 11).
rather than non-constant variance. In
light of these difficulties, Johnson and
Fractional Factorials for Screening
Wichern (1988, 229) recommend the follow-
ing heuristic approach to help determine Factorial experiments are often conducted
if the constant variance assumption holds for screening a large number of factors.
approximately. If the ratio of the largest The goal of such experiments is determining
variance to the smallest variance is greater the factors to which the response is most
than four, then the assumption of equality sensitive. Customarily, two or at most three
of variance is so strongly contradicted by the levels of each factor are used. To keep the
data that inferences about the means are in number of experimental runs manageable
jeopardy. and to reduce costs during screening,
The normal distribution assumption can only a fraction of the possible treatments
be checked by normal probability plots, as (combinations of factor levels) are run. Such
in regression. If the group sizes are large, a fractional factorial designs achieve their
separate normal probability plot can be efficiency by sacrificing tests for higher
made for each group; usually, it is more order interactions, and thus are useful
helpful to make one normal probability plot in situations where the main effects and
for the residuals from all the groups. two-way interactions are of much greater
magnitude than the higher order interac-
tions. Once a series of screening designs
Higher Order AN OVA
has been carried out to determine the most
To enable an investigator to understand a important factors, designs that use all
system or to make recommendations, vary- possible combinations and several levels of
ing only two factors at a time is often not each factor can be run to determine the
enough. For example, suppose a company optimal setting of each factor. The barbeque
wishes to produce a bar beque sauce. Assume sauce development might be handled in this
that it is developing this product for the first way.
time, rather than working with an existing
formulation. Features such as spice mix,
tomato sauce level, sweetener type and Response Surface Models
amount, vinegar level, gums and other Factorial experiments are frequently used to
thickeners would all have to be studied, and determine optimal settings of continuous
studied simultaneously. variables. Several levels of each factor are
 Statistical Methods 769

included in the experiment, and polynomial
regression models called response surface
models can be used to model the relation-
ship between the response and the factors.
Provided the polynomial model gives an
adequate description of the relationship, the
user is no longer limited, as with ANOVA,
to choosing only from the factor settings
actually run. Box, Hunter and Hunter
(1978, Chapter 15) give a good introduction
to response surface methods. Box and
Draper (1987) give a more comprehensive
treatment.
The relationship between the response
and the experimental factors can be studied
by making contour plots. Figure 18-8 gives
an example of a contour plot for a two-
factor experiment. Suppose that this experi-
ment was conducted to select a combination
of baking time and temperature that gives
the most appealing texture for muffins made
with a newly developed batter. The contour
plot of the response surface shows that
several different combinations of time
and temperature (those on the innermost
contour) produce near-optimum texture
ratings. In this case, the user can select the
most practical combination, such as the one
with the shortest baking time. The contours
are not necessarily elliptical, as in Figure
18-8; a variety of shapes are possible as
illustrated in Box and Draper (1987).
Mixture Designs
In the designed experiments we have
been discussing, the factor settings, whether
categorical variables or levels of continuous
variables, have been independent in the
sense that the setting of any one factor can
be changed without necessitating changes in
the settings of the others (for example,
cooking time and amount of sweetener).
In many product formulation and flavor
experiments, however, determining the
optimum blend of ingredients is the goal;
changing the level of one ingredient neces-
sarily alters the proportion of the remain-

24

21
(f)
(])
......
:::>
c
18
E
(])

E
......
15

Optimum
Response
12

325 335 345 355 365 375

temperature ("F)

FIGURE 18-8. Response surface contour plot for mufin texture.

770 Source Book of Flavors
ing ingredients. For example, suppose an
investigator seeks to optimize a prototype
spice blend that has been developed for
a frozen Chinese entree. The spice blend
includes star anise, cinnamon, cloves,
ginger, cardamon, fennel and Szechuan
pepper. Increasing the amount of star anise
causes the proportion of some or all of the
other spices to be reduced. Such an experi-
ment, in which the response is assumed to
be determined by the proportions of the
ingredients, is called a mixture problem.
Separate experiments may be conducted
to determine the optimum total amount of
spice; the hallmark of a mixture design is the
focus on the blend. The goal of a mixture
experiment is the same as that of a response
surface analysis: determination of the
blend or blends that produce the optimal
response.
The feature of mixture designs that is
most complicated from the user's point of
view is the selection of the blends to be
included in the experiment. Most presenta-
tions of mixture designs assume that the
response surface is low-order polynomial
(quadratic or cubic). Under this assump-
tion, more accurate estimates of the response
surface regression coefficients are obtained
when the experimental mixtures consist of
single ingredients, mixtures of only two
ingredients, and so on, with very few if any
being blends of all the ingredients. This is a
paradox, because in most cases where an
investigator is optimizing a flavor, blends
that leave out a large number of the com-
ponents are clearly unrealistic. If complex
interactions between the components are
suspected, then the response surface may
not be low-order polynomial and standard
mixture designs should not be used. In
addition, elementary derivations of mixture
designs assume that any logically possible
blend, no matter how extreme, could be the
best. If the blends of practical interest
comprise only a subset of the logically
possible ones, such restrictions can be
incorporated by using mixture designs that
allow the scientist to specify the region of
interest by giving upper and lower bounds
on the proportions of each ingredient.
Cornell (1990) gives references to algorithms
that find the design points, given such con-
straints. Details and specific examples are
given in Chapters 3 and 4. As with response
surfaces, the analysis of mixture design
models includes the examination of contour
plots to locate optimal or equivalently
optimal treatments.
Randomized Blocks and Repeated Measures
In many experiments, subjects or batches of
raw materials may be regarded as identical,
equivalent, or interchangeable. In other
experiments, however, the researcher may
wish to investigate the variability among the
subjects or the batches of raw material, or
may feel that these sources of variability
should be clearly separated from the vari-
ability due to the factors being manipulated
and from the random variability, the statis-
tical "error."
Paired comparisons provide a way of
allowing for subject-to-subject or batch-to-
batch differences when two treatments-
one experimental factor at two levels-are
being compared. When more than two
treatments are being studied, randomized
block models or repeated measures models
are employed. Different forms of these
models have been developed for use in dif-
ferent contexts.
Randomized block designs originated in
agricultural research, where different
locations or fields form the blocks. These
designs were adapted in industrial experi-
ments, where batches of raw materials or
different production days form the blocks.
In a randomized block design, the materials,
items, or individuals in the same block are
assumed to be homogeneous. All the treat-
ment combinations are tested in every
block. The characteristics that vary across
the blocks are assumed not to interact.
Repeated measures designs originated in
psychology, where subjects are observed
under different conditions. The terms

within-subject factor and between-subject
factor are used to describe the treatment
structure of repeated measures designs.
The subject differences are assumed not to
interact with the treatment factors.
Randomized block and repeated
measures models are analyzed with means,
plots, Ftests and multiple comparisons. The
computing details differ, but the concepts
are the same as for simpler designs.
COMPARING VARIANCES
Analysis of variance and t tests compare
population means, assuming that all other
features of the populations are the same. In
many applications, however, the research
question has to do with comparing the
variances of the groups. For example, a
decision may be made among suppliers of
an ingredient based on the suppliers' con-
sistency, as reflected by the variance.
The standard test for comparing variances
is the F test. There are extensions of the F
test to more than two independent popula-
tions. Bartlett's test (Neter, Wasserman
and Kutner 1990, Section 16.2) is the most
common. For small samples, Box's test
(Neter, Wasserman and Kutner 1990,
Section 16.2) gives more exact P values than
Bartlett's test. Both of these tests assume
that the populations being compared have
normal distributions. The tests are sensitive
to this assumption: they may incorrectly
reject the null hypothesis that the popula-
tion variances are equal if the population
distributions are other than normal (Neter,
Wasserman and Kutner 1990, 618; Johnson
and Wichern 1988, 229; Miller 1986, 92).
The references given here also discuss
some alternative tests for equality of
several variances. There is no test that is
both powerful and robust to distribution
assumptions.
MULTIVARIATE OBSERVATIONS
In many situations, several features of a
sample are measured and the investigator
Statistical Methods 771
wishes to treat the collection of measure-
ments as characterizing the sample. For
example, a researcher may have asked a
sensory panel to evaluate a large number of
attributes of a new line of products using
continuous line scales. Volatile profile data
collected on the products would be another
multivariate dataset, with each peak being
a variable. Graphically, the samples are
thought of as points in space; the dimension
of the space (p) is the number of variables
measured. For p greater than three, of
course, the points cannot literally be plotted.
Vector notation is used to handle multi-
variate data, the observations on each
sample forming a p x 1 column vector. Most
books on multivariate statistical methods
include a survey of vector and matrix nota-
tion. Johnson and Wichern (1988, Chapter
2) and Press (1982, Chapter 2) are two
useful resources.
Multivariate data are summarized numer-
ically by the averages of each variable, the
standard deviations or variances of each
variable, and the covariances or correla-
tions between each pair of variables. The
variances and covariances are collected
into a square matrix S with p rows and p
columns, with the variances down the
diagonal. This matrix S is called the variance-
covariance matrix, the covariance matrix, or
the variance matrix. Similarly, the correla-
tions can be collected into a square p x p
matrix R, which has 1's on the diagonal.
Because it is difficult to get a feel for a
matrix of numbers, two overall measures
of variance are used. These are typically
used for comparing variance matrices across
groups. The total variance is the sum of the
variances for all the variables. It may be
difficult to interpret if the units in which
they are measured are not the same. In
matrix terms, this is the sum of the diagonal
elements (the trace) of the variance-
covariance matrix. The generalized variance
is the determinant of the variance-covariance
matrix. It is proportional to the square of
the volume of the ellipsoids defined by
the data points. (Determinants and other
772 Source Book of Flavors
matrix quantities are usually provided by
software.)
Another set of numbers that characterizes
a p x p square matrix is its p eigenvalues,
also called characteristic values or roots,
which are often denoted by 'A. For covariance
and correlation matrices, the eigenvalues
are always non-negative. The sum of the
eigenvalues is equal to the sum of the
diagonal elements (the trace) of the matrix.
So, for a variance matrix S, the sum of the
eigenvalues is the total variance. Similarly,
the sum of the eigenvalues of a correlation
matrix R, is always 1 + 1 + ... + 1 = p.
The number of eigenvalues that are large,
relative to their sum, gives an indication of
the effective dimension of the data, which
is often much less than the number of
variables. Thus, eigenvalues play a key role
in dimension reduction, the search for linear
combinations that capture the essential
features of the dataset. As a rough rule,
an eigenvalue of the variance-covariance
matrix S that is more than 1/p percent of the
total variance is considered large. In terms
of the correlation matrix R, an eigenvalue
greater than 1 is considered large.
If the data are multivariate normal,
then means, variances and covariances are
sufficient to completely characterize the
distribution. The multivariate normal dis-
tribution has ellipsoidal contours in space.
The center of the p dimensional ellipsoid
has the means as its coordinates. The shape
and orientation of the ellipsoid are deter-
mined by the variances and covariances.
Since the contours of multivariate dis-
tributions cannot be visualized directly,
the following approach is used to check the
assumption of multivariate normality. The
distance between each point and the point
of averages is calculated using a special kind
of multivariate distance called Mahalanobis
distance. The values of the Mahalanobis
distances have a x2 distribution with p
degrees of freedom if the data are from a p
dimensional multivariate normal distribu-
tion. The Mahalanobis distances can be
plotted against order statistics, values
selected from the x2 distribution so that
the plot is a straight line if the data are
multivariate normal. This technique paral-
lels the normal probability plots used to
check regression assumptions.
Producing a two- or three-dimensional
picture that captures the essential features
of the data is one of the goals of multivariate
techniques that work with covariance or
correlation matrices. If the data are approxi-
mately multivariate normal, the longest axes
of the ellipsoid give a natural coordinate
system. Each axis is a different linear
combination of the original variables.
MULTIVARIATE ANALYSIS OF
VARIANCE (MANOV A)
MANOVA answers the question: "Is there
evidence that the different groups being
studied have different means?" when several
features of the groups are of simultaneous
interest. Thus, it is a multivariate extension
of ANOVA. The need for MANOVA is
illustrated by the plot of two features, Y1
and Y 2 , in Figure 18-9. If we examine the
Y1 values or the Y 2 values separately by
projecting the points onto the correspond-
ing axes, the considerable amount of
overlap will make it difficult for an ANOV A
(or t test) on Y1 or Y 2 alone to give con-
clusive evidence that the groups have dif-
ferent means. MANOVA is able to capture
what we see in the picture by incorporating
both variables into one test.
FIGURE 18-9. Groups requiring two dimensions for
separation.

MANOVA searches for linear combina-
tions of the data, for directions in the
data space, that maximize group separa-
tion. MANOVA calculates a P value to
determine how rare the group separation
observed in the sample is under the null
hypothesis that all the groups have the same
mean. The test assumes that the variance of
each variable is the same in each group,
that the correlations between each pair of
variables are the same in each group, and
that the groups have multivariate normal
distributions.
Several MANOVA test statistics are
available. For two groups, they are all
equivalent. The easiest two-group test
to interpret is Hotelling's T 2 , which is a
generalization of the two-independent-
sample t test. The observations are trans-
formed to the dimension of maximum
separation and then assessed by a t test. For
more than two groups, the MANOVA tests
are not equivalent. Since no one test is
clearly superior, we recommend that the
user consult Seber (1984, Section 8.6.2) for
a comparison.
If there is an ordering among the groups,
MANOVA cannot incorporate this. The
ambitious user may want to consider
multivariate regression models. This sub-
ject is discussed in the references for this
section.
Finding that the group means are not all
the same requires further investigation, just
as with ANOVA. However, multivariate
multiple comparison procedures have not
been developed as thoroughly as univariate
ones. The Bonferroni procedure can be
adapted to compare all pairs of groups
(Johnson and Wichern 1988, Section 6.5).
In addition to determining which groups
differ, exploring exactly which variables
differ may also be of interest as a followup
to MANOVA.
The essential point to remember is that
MANOVA is able to incorporate differences
that can be seen only by looking at more
than one variable at a time. Separation of
groups can also be studied by discriminant
Statistical Methods 773
analysis, which also uses the linear combina-
tions (canonical variates) that maximize
group separation. Plots that allow the user
to visualize group separation and overlap
are discussed in the next section.
DISCRIMINANT ANALYSIS
How can predictor variables that rep-
resent different input characteristics (i.e.,
ingredients) and processing or storage con-
ditions be used to distinguish between
groups? If a large number of predictor
variables such as chromatographic peaks are
available, which predictor variables are
most useful for predicting group member-
ship? To what degree can the groups be
separated? Based on the data, where group
membership has been definitively deter-
mined for the samples, how accurately
could we classify new samples, given only
their input characteristics and processing
conditions?
To answer these questions, discriminant
analysis finds linear combinations of the
predictor variables that maximize the dis-
tances between the group means. The
variables are first standardized to remove
the effects of different measurement scales.
Linear discriminant analysis assumes that
the variances of all the predictor variables
and the correlations between all pairs of
predictor variables are the same across
groups, just as in MANOVA. The different
groups are treated as unordered categories.
Even if there is a structural relationship
among the categories, such as increasing
intensities of a flavor defect, the procedure
cannot exploit this ordering.
Discriminant analysis produces two dis-
tinct sets of linear combinations of the
predictor variables: canonical variates and
Fisher linear discriminant functions. Since
the canonical variates have a richer inter-
pretation, the discussion here focuses on
them. The canonical variates create a new
coordinate system into which the observa-
tions can be projected to visualize the group
separation. The groups will have circular
774 Source Book of Flavors

or spherical contours when plotted in the canonical variate through the cloud of
canonical variate space. data points is in whatever direction gives
As an example, consider the following maximum separation of the group means.
dataset from Leland (1986). Milks exposed The second must be perpendicular to the
to fluorescent light to induce a light-oxidized first, and is in whichever of the possible
flavor defect were analyzed by gas chroma- remaining directions gives the maximum
tography, and the volatile peaks were used additional separation of group means. The
as predictor variables. Four light intensities number of canonical variates, and so the
defined the groups, A, B, C, and D. Because dimension of the canonical variate space, is
the gas chromatography produced a large the number of groups minus one or the
number of peaks, a forward stepwise selec- number of predictor variables , whichever
tion algorithm analogous to forward stepwise is less. Since the canonical variates are
regression was used to select highly dis- perpendicular (or orthogonal), they are
criminating peaks. Three volatiles were uncorrelated .
selected to separate the groups. With four As a result of the way the canonical
groups, there are three canonical variables; variates are calculated, the first canonical
in this example, the first two carry all the variate will have the largest variance be-
separating information. As illustrated in the tween groups , with each succeeding canon-
canonical variable plot (Figure 18-10), the ical variate having smaller between-group
first canonical variable separates group D variance . (Within each group, each canon-
and group C from each other and from ical variate has variance one.) The sum of
groups A and B. The second canonical the variances of all the canonical variates,
variable separates groups A and B from the total variance in this context, is used
each other. The group B sample flagged to calculate the percent of between-group
with an arrow is misclassified into group A. variability accounted for by each canonical
(This is discussed further below.) variate. In the light-oxidized flavor example,
The canonical variates are calculated in the first canonical variate accounts for 88
succession. Each is a linear combination percent of the total variation. The first two
of the predictors. The angle of the first canonical variates together account for 99.6

3
••
..
Ill Ill

Ill
Ill Ill
2
N A
..9? millie
.c ~0
co D

••
-~
> 0
• 6 00
00 0
<ii
.!:1
c
., •
•
Ill
B
0

0 Group A
c 6 6 0
co
(.) ·2
0 Group B 6 c6 6 00
6
6 Groupe 6
-3
•
Grouo c
{Group means denoled by le11er)
6

·4
-8 ·6 .4 ·2 0 2 4 6

Canonical Variable
FIGURE 18-10. Canonical variable plot for light-oxidized milks.
 Statistical Methods 775

TABLE 18-3. Classification Table for Light-Oxidized Flavor

Number of Cases Classified

Treatment into Group:
Group (ft-c) %Correct A B c c
A 0 100 11 0 0 0
B 75 90 1 9 0 0
c 275 100 0 0 9 0
D 700 100 0 0 0 10
97.5 (overall)

percent. A discriminant analysis is easy to
interpret, if the first two or three fitted
canonical variates capture a large propor-
tion of the variability among the group
means.
To assess the degree of separation be-
tween groups and the accuracy of the result-
ing classifications, a discriminant analysis
program uses the fitted canonical variates to
classify each case in turn. A case is trans-
formed to the canonical variate scale and
then classified into the group whose mean
is closest. Such assessments of the per-
formance of the discriminant function can
be calculated in two ways: using the fitted
canonical variates determined from all the
data, including the case being classified, or
classifying each case as if its group member-
ship were unknown, that is, using the canon-
ical variates fit only to the other cases. The
latter procedure, called "jackknifing,"
produces more realistic estimates of the mis-
classification rates that would be obtained
with future cases whose group membership
is unknown.
Probabilities of group membership are
also calculated under two assumptions:
Each case does belong to one of the groups
in the study, and the populations are multi-
variate normal. These probabilities indicate
the degree of uncertainty associated with
each classification.
A table of the classification results
for each group along with a canonical plot
provides a useful summary of a discriminant
analysis. The patterns of misclassification
and group overlap are worth exploring; just
reporting the overall misclassification rate
across all groups does not convey enough
information. The classification rates for
the light-oxidized flavor example are given
in Table 18-3. The degree of separation
achieved in this sample is extraordinary;
only one sample is misclassified, a group B
sample that is classified into group A. This
sample is the one flagged by an arrow in
Figure 18-10.
Now consider another classification table
(Table 18-4) constructed to illustrate what
happens if a group is not cohesive. Here,
the group C samples are split into two
subgroups, one close to group B and the
other close to group D. While the samples
from groups A, B, and Dare classified with
high reliability, the disappointing overall
percent of correct classification reflects the
difficulty with group C.
In some applications, the predictors that
separate the groups will be of theoretical or
practical interest. If the investigator wishes
to fully explore the role of certain predictors,
they can be forced into the discriminant
function. As with regression, simply letting
TABLE 18-4. Classification table with a non-cohesive
group
Number of Cases
Classified into Group:
Group %Correct A B c D
A 86 12 2 0 0
B 93 13 0 0
c 0 0 9 0 5
D 93 0 0 12
68 (overall)
776 Source Book of Flavors
a stepwise algorithm select predictors does
not take full advantage of the data and does
not draw on the scientist's knowledge.
CORRELATION MATRIX
METHODS FOR MULTIVARIATE
OBSERVATIONS
The techniques discussed up to this point
have focused on relating a response or
grouping variable to other variables. In
contrast, the techniques discussed in this
section are useful for multivariate data when
there is no response variable or grouping.
Principal components and factor analysis
can help researchers explore relation-
ships among individuals, items, or samples
using linear combinations of the variables
measured. These techniques can assist the
user in getting a feel for high-dimensional
data by discovering common underlying
dimensions.
Principal Components
Principal components uses the axes of the
ellipsoid of the data points in an attempt to
achieve the goals of dimension reduction. If
the first, second, or third principal com-
ponent axes can account for 80-90 percent
of the total variance, then these components
can effectively replace the large number of
original variables, thus reducing the dimen-
sion of the dataset. The principal com-
ponents can be substituted for the original
data in further statistical analysis. Studying
the principal components is a good way to
get a feel for high-dimensional data such as
sensory or volatile profiles.
Principal components can be calculated
either from the variance-covariance matrix
S or from the correlation matrix R. Calculat-
ing the principal components of R is equiv-
alent to calculating the principal com-
ponents of the standardized variables,
something that should be considered if the
measurement scales of the variables are not
commensurate. The principal components
calculated from S and R can give very dif-
ferent interpretations.
The number of principal components is
equal to the number of variables p. Each
principal component is a linear combination
of the p variables. The principal com-
ponents represent a change in axes in p
dimensional space; the point in p dimen-
sional space whose coordinates are the aver-
ages of the variables becomes the origin.
The direction of maximum variability is the
direction of the first principal component.
The direction of the second principal
component is the direction of maximum
variability perpendicular to the first prin-
cipal component.
Principal components do not require any
distribution assumptions. Because they are
perpendicular, the principal components are
uncorrelated. The variances of the principal
components are the eigenvalues of the
matrix, ordered from largest to smallest.
The proportion of the total variance "due
to" the kth principal component is its
variance Ak divided by the total variance
At + Az + ... + Ap. The proportion of
the total variance due to the first m prin-
cipal components is (At + Az + ... + Am)
divided by (At + Az + ... + Ap).
If 80 to 90 percent of the total variance is
accounted for by the first m principal com-
ponents, then these can effectively replace
the p variables. We have thus reduced the
dimension of the dataset from p tom.
The user should study the coefficients
for each principal component to see which
variables are most heavily weighted. If the
heavily weighted variables have something
in common, this common feature can be
used to name and interpret the component
axis. For example, suppose that all the
heavily weighted variables in the second
principal component for barbeque sauce
volatiles have been identified as phenols.
This axis might be labeled "smokey."
It is also possible to express each of the
original variables Xk as a linear combination
of the principal components PCt. ... , PCP:
 Statistical Methods 777

standardized variables will be used. Suppose

there are m common underlying factors,
This relationship is exact. If the first several Ft. F2, ... Fm. The number of factors is
principal components account for a large assumed known, but in practice, different
proportion of the total variance, the remain- numbers of factors are tried. All the factors
ing terms can be dropped from the equation. are assumed to have (and will be calculated
In these equations, the principal com- to have) zero means and variances of one;
ponents PCt. ... , PCP are linear combina- they are assumed to be uncorrelated. Each
tions of the original variables X 1 , ••• , XP of the standardized variables Zk is assumed
and the coefficients lk 1 , ••• , lkp are derived to be a linear combination of the common
from the variance-covariance matrix or factors, Ft. F2, ... , Fm plus a term Ek
correlation matrix. Everything on the right- specific to variable k:
hand side of the equals sign has been derived
from Xt. .. . , XP. Since the principal com-
ponents are themselves combinations of
Xt. ... , XP, expressing the X variables as The coefficient lk 1 is called the loading of
linear combinations of the principal com- (standardized) variable Zk on Factor 1, lk2 is
ponents may appear circular. This is true- called the loading of Zk on Factor 2, and so
we are going around in circles. The point of on. The Ek terms are each assumed to have
doing so, as a famous applied statistician is zero mean; each Ek has its own variance 'l'k·
said to have remarked, is that the view is Since Ek is supposed to represent the part of
better from some parts of the circle than Zk that is unique and not associated with the
from others: principal components are one common factors, Ek is assumed independent
way of finding these interesting vista points. of all common factors and independent of
all the other standardized variables.
The linear model of Zk has a form similar
Factor Analysis
to that of a linear regression. As with prin-
The goal of factor analysis is to account for cipal components, all the terms to the right
the correlations observed among many vari- of the equals sign must be estimated from
ables by finding a few common underlying the data. The usual approaches to this task
factors that cannot be evaluated directly, are iterative and involve a great deal of
but which give rise to the correlations computation.
observed among the attributes. Factor When factor analysis is done on the
analysis is similar to principal components standardized variables Zt. ... , Zp, the
analysis; however, their goals are slightly variance of each standardized variable is
different. The goal of principal components one. This variance is decomposed into the
is to account for as large a portion of the sum of two terms: the communality, the part
total variance as possible with a few com- of the variance of Zk that is attributed to the
ponents, while the goal of factor analysis is common factors, and 'l'k the variance of the
to account for the observed correlations. specific factor ek.
In part, principal components focuses on How do we determine if a factor analysis
the diagonal elements of the covariance or fit is successful, that is, do the m common
correlation matrix, while factor analysis factors account for the observed correla-
focuses on the off-diagonal elements. tions? One way to do this is to compute a
Factor analysis starts by postulating a fitted version of the correlation matrix from
statistical model. This can be done either for the estimated factor loadings and variances
the original variables Xk or their standard- of the specific factors, and compare it with
ized versions Zk = (Xk - Xk)!sk; here, the the observed correlation matrix R. The
778 Source Book of Flavors
difference between the observed and fitted
correlation matrix is called a residual
matrix. Examining the residual matrix gives
an overall impression of the adequacy of the
factor model and calls the analyst's attention
to any correlations or variables that are
poorly fit. Another way to assess the good-
ness of fit is to examine the variances of the
specific factors ek> which should be small if
the model fits well. A measure of fit that
parallels the one used for principal com-
ponents is the cumulative percent of total
variance explained by the common factors.
In factor analysis of the correlation
matrix, the loading lkj of standardized
variable Zk on common factor Fj is the
correlation between them. What the user of
factor analysis hopes for is the following
sort of pattern in the factor loadings: Each
variable Zk is highly correlated with only
one common factor, so that each common
factor has associated with it a distinct set of
original variables. Further, the user hopes
to see something in common among the set
of variables that are highly correlated
with each factor, or to verify hypothesized
groupings of variables by seeing that they all
"load heavily," that is, are highly correlated
with the same factor. Such interpretations
are facilitated by rotations of the factors,
which involve changes in coordinate systems.
Several rotation algorithms may be tried to
facilitate interpretation.
If a factor analysis is successful, the user
may wish to estimate the values of the com-
mon factors for individuals to aid in subject
selection or as input to another analysis.
Least squares methods are available to do
this; two methods are discussed by Johnson
and Wichern (1988, Section 9.5).
DISTANCE MATRIX METHODS:
CLUSTER ANALYSIS AND
MULTIDIMENSIONAL SCALING
Throughout this chapter, we have intro-
duced statistical methods by stating the
questions they help answer. In this section,
it is more natural to begin with the type
of data the researcher seeks to analyze: dis-
tances between pairs of samples.
For example, suppose a researcher is
interested in consumer perceptions of
similarities and differences among nine dif-
ferent varieties of fruit and spice herb
tea. Suppose further that each subject was
presented with all possible pairs (36) of
varieties and asked to assess the differences
between them on a scale from zero to 20.
The investigator then averages the distances
across subjects.
Two sorts of questions might arise with
distance data. One type is, which teas are
most similar? Do the teas fall into clusters,
distinctly separated groups consisting of teas
that are similar or close together? A second
type of question is, can we infer some
underlying dimensions from the collection
of distances? Can we discover a one-, two-,
or three-dimensional coordinate system into
which the nine teas fit, with interpretations
of the axes? For example, one dimension
might be the base fruit flavor (berry, apple,
orange, lemon) used and another might
reflect the spices (cloves, cinnamon, ... )
used. (If the user has some ideas about what
characteristics make the samples distinct,
these should be measured and analyzed in
addition to analyzing distances.)
Cluster analysis focuses on the search for
subgroups using the distances between the
points. It can also be conducted when the
investigator has measured several variables
on the samples, with the goal of search-
ing for subgroups of similar objects. Most
cluster analysis algorithms start from the
pairs of closest points and build up the
clusters.
Multidimensional scaling, on the other
hand, focuses on the search for underlying
dimensions. So, the goal of multidimensional
scaling is essentially the same as that of
principal components and factor analysis;
the difference is that multidimensional
scaling is . used when distance data were
collected, while principlll components and
factor analysis work with the correlation
matrix and with observed variables that

measure several characteristics of the
sample items. When such data are available,
principal components and/or factor analysis
should be used, as they will exploit the data
more fully.
Cluster Analysis
Cluster analysis builds an "upside down"
tree from the collection of interobject dis-
tances, linking together the most similar
objects at the base of the diagram (the
branches) and working up until all the
sample objects are joined at the trunk.
In most of these diagrams, distance is rep-
resented by the vertical scale. It is up to the
user to study the tree and determine where
on the vertical scale to "cut" it, thus deter-
mining the number and composition of the
clusters. In some implementations, the user
may specify the number of clusters to be
formed.
If cluster analysis is being done with
measurements on several variables instead
of distance measurements, the researcher
must decide how to compute distances.
Cluster analysis programs offer a variety
of ways to combine the variables to get
distances, and the researcher may wish to
try more than one distance measure to see
if the cluster results differ. The main con-
sideration in selecting a distance measure
is whether to standardize the original
measurements so that all variables have
the same variance. Standardizing is rec-
ommended when the original scales of
measurement are different, so that the
clustering results are not dominated by the
variables with the biggest natural range.
If the investigator has measured several
variables on the samples, graphical methods
such as faces or glyphs that construct a dis-
tinctive pictogram for each observation can
be used in conjunction with cluster analysis.
Visual inspection of the faces provides an
overall feel for similarities and differences
between the samples.
Cluster analysis is frequently conducted
to confirm a hypothesized grouping, by
Statistical Methods 779
comparing the clusters built from the dis-
tance matrix with those expected. For
example, in an investigation of regional
differences between wines where we have
collected volatile and other chemical data,
cluster analysis might be conducted to
see how well the regional groupings are
reproduced.
Multidimensional Scaling
Multidimensional scaling algorithms seek
to map the spatial relationships between
data points from the ensemble of distance
measurements. An analogy is trying to
reconstruct a map between cities given
only a table of intercity distances. The
reconstructed map may differ from the
original by being upside down or reversed
left to right. For the best one-dimensional,
two-dimensional, three-dimensional, and
so on representation of the observations, a
measure called stress quantifies the distor-
tion necessary to force the points into the
low-dimensional space. The stress measure
gives the user an idea of the number of
dimensions required to get an accurate map
of the data points. Relatively small values of
stress are ideal.
If the multidimensional scaling algorithm
finds a low-dimensional representation of
the samples with relatively low stress, the
user examines the plot and draws on the
characteristics of the samples and general
knowledge of the field to name the dimen-
sions. In the fruit and spice herb tea
examples, one dimension might be the base
fruit flavor used (berry, apple, orange,
lemon) and another might reflect the spices
used (cloves, cinnamon, ... ).
Whenever the investigator has measured
several characteristics of the samples in
addition to having the subjects assess dis-
tances, other statistical techniques that
use variables directly can give insights com-
plementary to those produced by analyzing
the distances. The coordinate system given
by the principal components may be easier
to interpret than that given by multi-
780 Source Book of Flavors

dimensional scaling, since the user can as correlated as possible, subject to the
examine the principal component equation requirement that the second canonical
to see which variables are heavily weighted. variate for the X's (and Y's) is perpendicular
Also, the principal component plots can be to the first canonical variate for the X's (and
examined for clustering. If the user has Y's). The number of canonical variate pairs
hypotheses about how the samples should that can be derived is p or q, whichever is
be grouped, discriminant analysis can be less, although it is frequently the case that
used to investigate how the proposed groups only the first few pairs show significant
differ. correlations.
One of the uses of the canonical variates
is to construct indexes from the measured
CANONICAL CORRELATION
variates. In the sensory and instrumental
Suppose an investigator has asked a sensory measurement example, the first canonical
panel to use continuous line scales or variate for the instrumental measurements
categorical scales to assess samples on might be used as a predictor of sensory
a number of attributes, and has also used quality.
analytical techniques such as gas chroma-
tography to measure a number of variables, ANALYSIS OF CATEGORICAL
such as volatiles for each sample. How can
RESPONSE VARIABLES
the investigator search for relationships
between the sensory and instrumental Response variables that are categorical lead
profiles? Canonical variates analysis is to data that are counts or proportions.
one way to find linkages between two sets Categorical variables may be nominal, such
of measurements such as these. If the as sweetener type used in a cola drink, or
researcher sought to model a single sensory ordinal, such as medium, sharp or extra
characteristic, say flavor quality, as a func- sharp ratings of Cheddar cheese. Ordinal
tion of a set of continuous instrumental variables may result from grouping con-
measurements, then regression, logistic tinuous variables; for example, the aging
regression, or discriminant analysis would time of Cheddar cheese may be coded as
be useful, depending upon the type of 45-75 days, 75-120 days, 120-180 days,
sensory information collected. Canonical and 180-360 days to produce four ordered
variates analysis tries to correlate two sets of categories. In a study of the effect of aging
continuous measurements, X's and Y's, on sharpness, the aging variable is explana-
using pairs of linear combinations of the X's tory, while the sharpness rating is the
and Y's. Several pairs of linear combina- response. Models for ordinal variables
tions may be required to express the rela- assume that the order of the categories
tionships among the two sets of variables. matters, but that distances between ad-
Suppose we call the two sets of measure- jacent categories may differ. Models for
ments X variables and Y variables, and nominal data assume there is no ordering
suppose we have p X variables and q Y among the categories. These models may be
variables. Canonical correlation begins by used with ordinal data, although such an
finding a linear combination of X 1 , . . . , XP analysis ignores some of the information in
and a second linear combination of Y1 , . . . , the data. Models for categorical response
Yq which have the highest possible correla- data assume different statistical distribu-
tion. These linear combinations are the first tions (e.g., binomial, multinomial, or
canonical variate for the X's and the first Poisson) than the normal distribution
canonical variate for the Y's. The pro- usually assumed in modeling continuous
cedure then looks for another pair of linear responses. An important practical implica-
combinations of the X's and the Y's that are tion of this difference is that constant

variance is no longer assumed; in categorical
response models, the variance of the
responses is instead proportional to the
mean response.
When the explanatory variables are also
categorical, the data are often called "cross
classified." The categories must be defined
so that each sample individual or item
belongs to exactly one of the categories
for each variable. Continuous explanatory
variables can also be used to model cate-
gorical response variables. When the
response variable has only two categories
(binary), the logistic regression model can
be used to model the response as a function
of continuous predictors.
Analyzing and modeling categorical data
has been an area of extensive statistical
development over the last 25 years. This
section surveys these techniques, introduc-
ing the reader to the methods and the situa-
tions in which they are applicable, and
providing some key references. Software
and textbooks facilitating the use of these
techniques are available for unordered
categorical (nominal) variables; Fienberg
(1980) gives a thorough treatment with
many examples. The corresponding methods
for ordered categorical (ordinal) data are
less readily available outside of statis-
tical journals; Agresti's books (1984 and
especially 1990) are the major sources.
Testing and Measuring Association
with Two Categorical Variables
Studies involving two categorical variables
have as basic data two-way tables of counts
TABLE 18-5. Table (3 x 3) for Cheddar Cheese Example
Cheddar cheese
Cure Time
(days) Medium Sharp
75-120 9 3
120-180 3 7
180-360 1 4
Column Total 13 14
Statistical Methods 781
with I rows and J columns. For example, in
a Cheddar cheese study where aging is the
explanatory variable and sharpness rating
is the response variable, an investigator
may have asked a panel to classify Cheddar
cheese samples as medium, sharp, or extra
sharp. The ratings are tabulated according
to three aging periods in a 3 x 3 table, as
illustrated in Table 18.5. Here the aging
variable is an explanatory variable and
sharpness rating is a response. In other
cases, all the categorical variables have
similar roles; neither one is obviously a
response to the other. An example in which
buyers of cola beverage are classified
according to two scales: regular or diet, and
caffeine-free versus caffeinated illustrates
this. (For simplicity, assume each buyer
purchases only one type.)
The counts in the body of the two-way
table are called cell counts; the row and
column sums, which represent the counts
for each variable separately, are called
marginal counts. These counts can be con-
verted to several useful proportions, which
correspond to various kinds of probabilities.
Questions of the form: What fraction of the
Cheddar cheese samples were both aged
120-180 days and classified by the panel
as extra sharp? are answered by the joint
probabilities. These probabilities are
denoted by P(A and B). The conditional
probabilities answer questions of the form:
What are the proportions of medium, sharp,
and extra-sharp among the samples aged
120-180 days? These probabilities are
denoted by P(BIA), read "probability of B
given A." The marginal probabilities answer
Extra-sharp Row Total
0 12
2 12
7 12
9
782 Source Book of Flavors
questions of the form: what are the overall
percents of medium, sharp and extra-
sharp among the cheese samples? These
probabilities are denoted by P(B).
Analysis of the counts and sample
proportions focuses on the question: Is
there evidence of association between the
two categorical variables, or does it appear
that they are independent? For example, is
there an association between aging category
and proportion of samples rated extra-
sharp, or is the proportion of extra-sharp
cheddar samples the same in all three aging
categories? Independence means that the
conditional probability distributions of B
given A are the same for all categories of A,
which in turn means they are all identical to
the marginal distribution of B. Equivalently,
independence means that all the joint
probabilities of the P(A and B) form are
equal to the product of the corresponding
marginals P(A) x P(B).
To test for the presence of association,
the x2 test is used with a two-way table
of counts. This test is constructed so that
independence is the null hypothesis and
association (lack of independence) is the
alternative hypothesis. For tables that have
very small counts, Fisher's exact test is used
instead of the x2 test (Fleiss 1981, Section
2.2; Rosner 1986, Section 10.5).
In addition to tests that give a yes or no
answer to the question: Is there evidence
of association between two categorical
variables?, several measures of the strength
of association are available. These can be
especially helpful in comparing tables from
different studies. For 2 x 2 tables these are
fairly straightforward; the same measures
can be used for both ordinal and nominal
variables since order is inconsequential
when contrasting only two categories.
In the cola example, the user may wish
to examine the proportion of diet cola
purchases that were caffeine-free versus the
proportion of regular purchases that were
caffeine-free. These are the conditional
probabilities P(caffeine-freeldiet) and
P(caffeine-freelregular). The strength of
association may be measured by the dif-
ference in these conditional proportions, by
their ratio, often called the relative risk
(reflecting the measure's medical heritage),
or by the odds ratio, e. The odds are ratios
of conditional probabilities. The odds of
purchasing caffeine-free among regular
cola buyers is P(caffeine-freeiregular)/
P(caffeinatedlregular), while the odds
of purchasing caffeine-free among diet
cola buyers is P(caffeine-freeldiet)/
P(caffeinatedldiet). The odds ratio 8 is the
ratio of the two odds. Since it can also
be expressed in terms of the four joint
probabilities, the odds ratio is also called the
cross-product ratio. If there is no association
among the variables, the relative risk and
the odds ratio are both equal to one. These
quantities range over the positive real
numbers; values far from one in either
direction indicate strong association.
Reciprocal values reflect the same strength
of association. For example, odds ratios of
15 and 1115 can arise from the same table,
depending upon which of the two variables
we use as the given in the conditional
probability.
Measures of association for I x J tables
larger than 2 x 2 are more complicated.
These measures differ depending upon
whether the variables are ordinal or nominal.
For two ordinal variables, Gamma is a
measure based on the concordance or dis-
cordance of all possible pairs of samples.
Two sample objects are concordant, if one is
higher than the other on both ordinal scales;
they are discordant, if the order is reversed.
For example, a Cheddar cheese sample,
aged 120-180 days and rated sharp, and
another sample, aged 180-360 days and
rated extra-sharp, are concordant. Gamma
is loosely analogous to a correlation co-
efficient: y is between -1 and 1, y = 0 if the
variables are independent, and y = 1 or -1
if all pairs are concordant. Other measures
of association for ordinal variables are
Kendall's 'tb and Somers's d. For two
nominal variables, it is more difficult to
summarize the association in an I x J table

by one number. Goodman and Kruskal's
concentration coefficient 't (1979) compares
the variation in the conditional distribu-
tions with the variation in the marginal
distribution.
Measures of association can be especially
helpful in comparing tables from different
studies. In the cola example, a Z test for the
equality of proportions of caffeine-free
cola purchases in the regular and diet soda
groups is equivalent to the x2 test for
association in the 2 x 2 table. (The P values
are identical; the x2 statistic is the square of
the Z statistic.) If a confidence interval
for the difference between proportions is
useful, then the two-independent-sample
approach is the recommended analysis.
Modeling with Categorical Variables
A modeling approach can provide much
more insight than x2 tests, especially for
datasets with three or more categorical
variables. This approach might allow
Cheddar cheese sharpness to be modeled as
a function of aging time and processing
method. The theory of generalized linear
models, parallel in many ways to regression,
provides goodness of fit measures, tests
for comparing nested models, tests for
specific effects, and residual analyses. The
generalized linear models that are used for
categorical responses utilize two different
transformations of the response: the logit
transformation of a proportion rc, which is
the natural log of rc/(1 - rc), and the natural
log of the cell counts. Models using the
latter transformation are called log-linear
models. The right-hand side of these models
are either of the regression form ~0 + ~ 1 X1
+ ... + ~PXP, where the X's are continous
variables, or of the ANOVA form: 11 + a; +
~j + a~;j, for example.
A model of the ANOVA form with as
many parameters as there are degrees of
freedom in the table is called a saturated
model. This model represents the situation
where no simplifying structure among the
cell probabilities is assumed. In a log-linear
Statistical Methods 783
model for a two-way table, the saturated
model has the form
where m;j denotes the expected cell count
for the ith row and jth column, 11 is an
overall mean, the 'A/ terms represent effects
for the row variable A, the 'A/ terms rep-
resent effects for the column variable B, and
the 'A// terms represent interaction effects.
A model that includes only the row and
column effects,
is the independence model.
An example with three categorical
variables gives some idea of the advantages
(and complexity) of log-linear models.
Three categories of variables A, B, and
C are mutually independent if the cell
probabilities are all equal to the product of
the corresponding marginals: P(A and B
and C)= P(A) X P(B) x P(C). B is said to
be jointly independent of A and C if P(BIA
and C) is equal to the marginal probability
P(B). A and B are said to be conditionally
independent of C if P(A and Bl C) = P(A IC)
x P(BIC). For example, it may turn out that
Cheddar cheese sharpness and processing
method are conditionally independent,
given the aging time category. Another way
of characterizing conditional independence
is P(AIB and C) = P(AIC). In the example,
this corresponds to the proportion of sharp
cheese for each aging category being equal
for each processing method. Many different
combinations of these relationships are
possible. The saturated model for the three-
way table includes terms that parallel the
three-way interactions, two-way interaction,
and main effects in ANOV A:
The model with the three-way interaction
terms removed represents the situation
784 Source Book of Flavors
where no pair of variables is jointly in-
dependent of each other. The models with
some but not all of the two-way interaction
terms represent various combinations of
joint and marginal independence. The
model with only main effects represents A,
B, and C mutually independent, an additive
model on the log scale. When two log-linear
models are nested within each other, a test
using the G 2 statistic can be used to compare
their fit. Some measures of goodness of fit
similar to R2 have been developed.
When the categorical variables are
ordinal, the interaction terms may have a
structure that is statistically simple. Models
for ordinal variables require that the user
assign numerical scores to the ordered
categories. For example, the cheese sharp-
ness variable might be assigned scores such
as medium= 1, sharp= 3, extra-sharp= 4.
Often, equally spaced integer scores are
used. If scores ~i and vj are assigned to
categorical variables A and B, the interac-
tion terms A.// may be modeled as ~~ivj,
which involves only one parameter~ (taking
the score values ~i and vj as known). This
particular model is called linear-by-linear
interaction. Interaction patterns range
in complexity from linear-by-linear (the
simplest) to completely separate A.// (the
most complex). If some but not all of the
categorical variables are ordinal, scores can
be assigned to them and hybrid models
constructed (Agresti 1990, Chapters 8
and 9).
Logistic Regression
Models that relate categorical response
variables to continuous explanatory vari-
ables Xt. ... , XP focus on predicting the
response proportion or probability for each
category.
When the response variable is binary,
having only two categories generically
termed success and failure, the logit trans-
formation is used and the resulting model
is called logistic regression. If 7t is the
probability that a population response is a
success, the model is
log(7t/(1 - 1t)) = ~0 + ~ 1 X1 + ... +
~pXp
Because of the differing distribution
assumptions and the need to translate from
the fitted logit scale to the probability
scale, algorithms specifically designed for
logistic regression should be used rather
than ordinary least squares algorithms.
Many of the logistic regression programs
implement a forward stepwise variable
selection procedure, as well as fitting user-
specified models. The method used to fit
logistic regressions in most contemporary
programs is maximum likelihood, so the test
statistics are technically different from the
familiar regression t and F tests, but the
interpretation issues are the same. Afifi and
Clark (1984, Chapter 12) and Hosmer and
Lemeshow (1989) are useful references.
Binary response variables can also be
analyzed by discriminant analysis, which
searches for linear combinations of the X
variables that maximize group separa-
tion. Because of the differing distribution
assumptions the resulting models will differ
from logistic regression models. With binary
response variables, the user is encouraged
to explore both techniques.
Expansions of the logistic regression
model to nominal categorical response
variables with more than two categories,
called polytomous variables in contrast to
dichotomous (binary) variables, are being
developed. These models address the same
question as discriminant analysis, but make
different assumptions. While discriminant
analysis is more commonly used, polytomous
regression models might be more appro-
priate if their assumptions more closely
match the data.
Methods for modeling ordinal categorical
responses are available; most of these
assume the existence of an underlying con-
tinuous variable and so require the user to
specify scores for the categories. These

models are discussed by Agresti (1990), and
in the references found there.
CONCLUSION
This chapter has been a beginning. Our goal
has been to enable the reader to use the
basic techniques competently and confident-
ly, and to interact effectively with statistical
consultants. Where would we go from here?
What sorts of techniques could be added to
the statistical tool kit of the investigator who
has mastered the methods discussed here?
The user who has a solid grasp of linear
regression can move on to generalized linear
models. These models expand the range of
functional forms relating the mean response
to the predictor variables and introduce
functions that relate the variance of the
response to the predictor variables. They
also expand the distributions used to model
the random variability. The log-linear
models we discussed for categorical data
are generalized linear models. McCullagh
and Neider (1989) is the comprehensive
reference on generalized linear models.
However, it is not a textbook, and few user-
oriented materials are available. Nonlinear
regression models expand the range of
functional forms relating response and
predictors even further, though constant
variance and the normal distribution are
usually assumed. Draper and Smith (1981)
have a good introductory chapter on non-
linear regression. Bates and Watts (1988)
address both practical and theoretical
aspects of nonlinear regression, as do Seber
and Wild (1989).
The user who frequently designs experi-
ments will need to master models that
include large numbers of factors, and com-
plicated blocking and sampling schemes.
Neter, Wasserman and Kutner (1990) dis-
cuss nested models; these often arise when
sampling product from retail outlets or
distribution centers. Box, Hunter and
Hunter (1978), and Box and Draper (1987)
have good examples of fractional factorials
and response surface modeling. Many of
Statistical Methods 785
their examples are from chemical engineer-
ing, so the nature of the examples will
not be alien to food chemists. As we have
mentioned, Cornell (1990) is the standard
reference for mixture designs.
The user who has a good background
in discriminant analysis can move on to
techniques that relax one or more of the
linear discriminant model assumptions.
Quadratic discriminant analysis allows for
non-constant variances. Techniques such as
SIMCA also allow for the possibility that a
case being classified does not come from any
of the groups used in building the model.
K-nearest-neighbor (KNN) classification, an
approach closely related to cluster analysis,
does not require any distribution assump-
tions. While classification techniques such as
SIMCA and KNN require fewer assump-
tions than linear discriminant analysis,
discriminant analysis outperforms them
when its assumptions are met. Thus, SJMCA
and KNN supplement, rather than replace,
discriminant analysis. Sharaf, Illman, and
Kowalski (1986) give a thorough introduc-
tion to both SIMCA and KNN classification.
The user who has become familiar with
multiple regression, principal components
and canonical correlation can move on to
more complicated techniques that can relate
several sets of variables. These techniques
are given different names in different fields
of applications. The one most commonly
used in chemistry is partial least squares
(PLS). Similar models are called structural
equations in the social and behavioral
sciences; those involved in sensory analysis
may hear this term used. Sharaf, Illman and
Kowalski (1986) introduce PLS modeling.
We have deliberately omitted any
references to specific statistical software.
We cannot provide anything guaranteed to
stand the test of time because of the rapid
evolution of statistical computing. Personal
computers (PC's) are becoming powerful
enough to carry out statistical analyses
that were once only feasible on centralized
"main-frame" systems. Software designed
to take advantage of this new computing
786 Source Book of Flavors
environment is much easier to learn and
use, although it is just beginning to appear.
Integrated packages (as opposed to stand-
alone specialized programs) that carry out
a variety of analyses commonly needed in
chemical laboratories are also beginning to
appear.
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Moore, D.S., and McCabe, G.P. 1989. Introduc-
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 Chapter 19
Food Colorants
THE NEED FOR FOOD COLOR
Many natural food materials are character-
istically associated with an attractive color
which, in part, may act as a guide to their
quality and edibility. Unfortunately, this
intrinsic color is often destroyed, totally or
partially, during processing, particularly if
heat is applied, so that the resulting food
product may have a far from attractive
appearance. Also, formulated foods may
lack the desired color due to too little
color, or incorrect color from ingredients.
Although one of the main attributes of
edible products is their flavor, the correct
and anticipated color also contributes sig-
nificantly to their acceptance and appeal;
flavor and color perception are intimately
linked. Home economists, having produced
a recipe with an appetizing flavor, recognize
the need for embellishing a meal to give the
correct color balance and arrangement on
presentation; this, in turn, stimulates the
desire to eat and so aids the digestion of the
food.
Colorants are used in the manufacture of
edible products for the following reasons:
a. Give the product the desired and
characteristic color, thereby creating
an appetizing appearance.
788
b. Enhance flavor appreciation.
c. Maintain the product appearance
within acceptable norms by correcting
objectionable color change or natural
variations.
d. Decorative purposes.
Colorants should never be used to dis-
guise inferior quality or deceive the con-
sumer in judging the wholesomeness of
food. In most regulations, this is expressly
forbidden.
INTERNATIONAL REGULATIONS
FOR COLORANTS
The color additives that are used for
coloring foods, drugs, and cosmetics are
divided into three groups: (1) the synthetic
organic colorings; (2) the natural pigments,
which may be of either vegetable or animal
origin; and (3) the inorganic colors, which
may be of synthetic or mineral origin. Of
these, synthetic dyes form by far the largest
proportion of coloring materials used.
The need for coloring foods, beverages,
candy, etc., is universally accepted, but as
yet there is no agreement on what may or
may not be used safely for this purpose.
Regulations and permitted lists of colors

differ widely throughout the world. Safety
in use is very important to consumers and
colorants, as food additives are under
constant and critical review by the Joint
FAO/WHO Expert Committee on Food
Additives, as well as all governmental
bodies throughout the world responsible for
their regulation.
Most countries have enacted legislation
precisely defining the nature and quality of
colorants permitted in food products. It is
implicit that the manufacturer of any such
products comply with the regulations of the
country in which the goods containing the
colorant are to be consumed. Regulations
governing this class of food additives differ
in almost all the developed countries, and
are constantly changing as toxicological in-
formation on their long-term use becomes
available. Very few food colors are univer-
sally acceptable. Current legislative action is
toward the further restriction of synthetic
colorants, even though many have been
widely used for decades. One has only to
compare the lists of food colors in use 20
years ago with those permitted at present to
realize how many have been banned over
this period. Natural colorants cannot be
assumed to be nontoxic and as they are
metabolically and toxicologically tested,
some may eventually be barred.
The dynamic nature of the list of food
colorants permitted throughout the world,
the variation in what is permitted from
country to country, and the importance that
a food company not violate the current
labeling laws of a country preclude any
attempt to publish a global listing of per-
mitted colorants in this text. One must
consult the current food colorant regula-
tions of each country regarding permissible
colorants and any restrictions in usage. The
current list of permitted food colorants
in the U.S. will be presented later in this
chapter (Hallagan 1991; Lauro 1991).
Food Colorants 789
U.S. REGULATIONS FOR FOOD
COLORANTS
Historical Perspective
Federal Food, Drug, and
Cosmetic Act of 1938
This law was passed by Congress on June
25, 1938, and became effective January 1,
1940. This Act contained the requirement
that only certified coal-tar colors could be
used in foods, drugs and cosmetics. The use
of any uncertified coal-tar color was con-
sidered as adulteration and, as such, was a
misdemeanor, punishable by law.
Under this Act, three different groups
of colorants were listed: (1) FD&C colors
were colors certifiable for use in coloring
foods, drugs and cosmetics. (2) D&C colors
were colors certifiable for use in drugs and
cosmetics, but not in foods. This constituted
a group of dyes and pigments considered
suitable for use in drugs and cosmetics for
internal use, when coming in contact with
mucous membranes or when ingested only
occasionally. (3) External D&C colors con-
stituted a group that, because of their oral
toxicity, were certifiable only for use in
products that are applied externally. They
were not permitted for use in products that
are ingested, or for use on any mucous
membrane.
Color Additives Amendments of 1960
(Public Law 86-618)
This law amended the Food, Drug and
Cosmetic Act of 1938 to authorize the use
of suitable color additives in or on foods,
drugs and cosmetics in accordance with
regulations prescribing the conditions under
which such additives may be used safely.
Under this new law, the Secretary of Health
and Human Services [formerly Health,
Education and Welfare (HEW)] was re-
quired to list separately color additives for
use in foods, drugs and cosmetics to the
extent that these listed color additives were
suitable and safe when used in accordance
with published regulations.
The Color Additive Amendments of 1960
790 Source Book of Flavors
provided that the Secretary, in determining
whether a proposed use of a color additive
was safe, must consider among other rel-
evant factors: (1) probable consumption; (2)
cumulative effect; (3) safety factors; (4)
availability of any needed practical methods
of analysis for determining the identity and
quantity of: (a) the pure dye, and all inter-
mediates and other impurities contained in
such color additive; (b) such additive in or
on any article of food, drug, or cosmetic;
and (c) any substance formed in or on such
article because of use of such additive.
Current Status of Food Colors
The current status of food colors, both in
terms of legal use and labeling require-
ments, can be found in the CFR 21 Parts
70-82. While the reader is encouraged to go
to the most recent publication of the CFR
for current information, some information
will be extracted from it and presented in
the following discussion.
CERTIFIED FOOD COLORS
Dyes
Certified colors are covered under the Food,
Drug and Cosmetic Act of 1938, section
406-B-"The Secretary shall promulgate
regulations for the certification of coal-tar
colors which are harmless and suitable for
use in foods." It should be noted that each
manufacturing batch of food colors must
be analyzed as required by law, and then
certified as meeting the established analytical
criteria prior to certification. Certification of
the colorant is typically done by the color
manufacturer through a self-certification
program rather than by the FDA. Certifica-
tion is safeguarded by the Food and Drug
Administration to such an extent that as
soon as any container of color is opened
by a person other than the food, drug or
cosmetic manufacturer who intends to use it
in his product, it is no longer considered
certified. Certified colors may not be con-
verted to liquid paste colors for resale unless
the new batch is submitted to the Food and
Drug Administration for recertification.
The use of certified, or natural color is
permitted in food products to enhance their
appearance. They are forbidden when their
use conceals inferiority or deceives the pur-
chaser. Individual states have rulings and
laws that sometimes do not conform to
Federal laws. Therefore, users should cor-
rectly inform themselves before coloring a
food product for interstate shipment. If the
coloring of a particular food product is pro-
hibited, no color, whether certified or of
natural origin, is permitted.
At present, seven certified colors are
permitted in the United States. They are
FD&C Blue No. 1, Blue No. 2, Green
No.3, Red No.3 (Lake is not permitted and
dye is limited to foods only), Red No. 40,
Yellow No. 5 and Yellow No. 6. From
these basic colorants, the entire range of
colors can be reproduced through blending.
Review articles covering their use in foods
have been published by Dziezak (1987) and
Rush (1986).
Label Declaration of Certified Colors
The currently permitted labeling of certified
colors is undergoing change in the United
States as a result of the passage of The
Nutrition Labeling and Education Act of
1990. This act has an influence on how
certified colors can be labeled in the United
States. Previously, the certified colors could
be listed in the ingredient statement as
"artificial color," "color added," "certified
color" or "U.S. certified color." The current
legislation reserves "color added" only for
the use of noncertified (exempt) colors. In
addition, certified colors would each
have to be listed by name in the ingredient
listing of the product. Previously, only
Yellow #5 had to be listed by name. This
amendment requires that the FDA issue a
final regulation within twelve months of
passage.
 Food Colorants 791

TABLE 19-1. Certified FDC Colors Permitted in Foods in the United States (Frick and Meggos 1988)

FDA Name and Current Regulatory

Common Name Chemical Class Chemical Structure Status of Lake Form•

FD&C Blue No. 1 Triphenyl methane ,...t .... Dye-Permanently

Brilliant Blue FCF t::r--lllc,HI)CI\-v listed for all uses at
C(tJ.=•.,..,~-n GMP. 21 CFR §§74.101,
74.1101,74.2101
'-\O.NI

FD&CEiueNo.l Fed. Reg. 47:42563

December 28, 1982
Lake-Provisionally
listed for all uses at
GMP. 21 CFR §82.101
FD&C Blue No. 2 Sulfonated indigo Dye-Permanently
Indigotine listed for all uses at
GMP. 21 CFR §§74.102,
74.1102
Fed. Reg. 48:5252
February 4, 1983
Lake-Provisionally
listed for all uses at

l
GMP. 21 CFR §82.102
FD&C Green No. 3 Triphenyl methane Dye-Permanently
Fast Green FCF l" 'i"
.,i~.~)..
j-- listed for all uses at
_J) y;y~-
<II),
0. -., .
so,
GMP. 21 CFR §§74.203,
74.1203,74.2203
Fed. Reg. 47:52140
November 19,1982
Lake-Provisionally
listed for all uses at
GMP. 21 CFR §82.203
FD&C Red No. 3 Fluorescein type Dye-Permanently
Erythrosine listed for foods and
ingested drugs GMP. 21
CFR §§74.303, 74.1303
Fed. Reg. 34:7446
MayS, 1969
Delisted for comestic
uses. Fed. Reg. 55:3516
February 1, 1990
Lake-Delisted for all
uses. Fed. Reg. 55:3516
February 1, 1990
21 CFR §81.10(u)
FD&C Red No. 40 Azo Dye-Permanently
AlluraRed
··~.P:=·-b
QrH,
listed for all uses at
GMP. 21 CFR §§74.340,
SO,No
74.1340,74.2340
Fed. Reg. 39:44198
December 23, 1974
Lake-permanently
listed for all uses at
GMP. 21 CFR §§74.340,
74.1340,74.2340
792 Source Book of Flavors
TABLE 19-1. Continued
FDA Name and
Common Name Chemical Class
FD&CYellowNo. 5 Azo
Tartrazine
FD&CYellowNo. 6 Azo
Sunset Yell ow FCF
• Dye forms of all seven colors are permanently listed.
FD&CDyes
There are two types of certified colorants:
dyes and lakes. Food dyes are water-soluble
compounds, most of which are either sul-
fonates, or sodium or potassium salts of acid
compounds. They may be classified on the
basis of their chemical structure (Table 19-
1). The lakes are insoluble pigments, which
have been permitted for use in the United
States only since 1959. These pigments
comprise the prime dye combined with
aluminum hydroxide under carefully con-
trolled conditions. They are quite different
from a dispersion of the dye on a suitable
edible carrier (e.g., starch).
Although representing widely different
organic structures, the features of chemical
constitution commonly associated with food
colorants are those that relate to freedom
from toxicity; high solubility in water,
ethanol and glycerol; attractiveness of hue;
and good stability over a wide range of
pH, in the presence of other food and/or
flavoring materials, food additives, etc.; and
under varying conditions of heat, light,
bacterial and chemical (primarily S0 2)
action during processing or storage. Most of
Current Regulatory
Chemical Structure Status of Lake Form•
Dye-Permanently
listed for all uses at
GMP. 21 CFR §§74.705,
74.1705,74.2705
SO,No
Fed. Reg. 50:35774
September 4, 1985
Lake-Provisionally
listed for all uses at
GMP. 21 CFR §82.705
Dye-Permanently
s~•-Q-s=s-a listed for all uses at
GMP. 21 CFR §§74.706,
so.~. 74.1706, 74.2706
Fed. Reg. 51:41765
November 19, 1986
Lake-Provisionally
listed for all uses at
GMP. 21 CFR §82.706
the soluble food colors contain about 90
percent of the pure dye, the remainder
being residual salts arising from the pro-
cessing. The tinctorial power of the dye is
directly proportional to its purity, which is
implied by the title or, if less than specifica-
tion, is clearly indicated on the label.
There is no organized system of desig-
nating colors, and many commonly used
names are those originally determined by
the manufacturer. The Color Index (1957),
published jointly by the United States and
United Kingdom societies of colorists, lists
the whole range of prime organic dyes and
assigns to each a specific number, called
the Color Index (CI), by which any color
chemical can be positively identified. Many
official lists use alternative designations
involving either numerical (e.g., FD&C
Red No. 2) or letter (e.g., Sunset Yellow
FCF) codes; but the use of the CI number as
well precludes doubts as to identity. For
example, Amaranth is known as FD&C Red
No. 2 (CI 16185) and this is not the same
chemical as Red 2G (CI 18050), which is not
permitted for use in food in the United
States. The similarity of title could lead to
 Food Colorants 793

misunderstanding, whereas the use of the CI light-stable, is very stable in acid media, but
numbers obviates this. only poorly so in alkaline media. It has good
stability in the presence of both benzoic acid
Characteristics of the Certified Food Colors and S02 . Carmoisine was not permitted for
The following dyes are used in food pro- use in foods in the United States at the time
cessing throughout the world, although their of writing, but is undergoing toxicological
use may be restricted or forbidden by testing as a possible replacement for
national legislation. amaranth.
FD&C Red #3 (Erythrosine) CI 45430
Red Colors Erythrosine is the disodium salt of 9-o-
FD&C Red 2 (Amaranth) CI 18185 carboxyphenyl-6-hydroxy-2, 4, 5, 7-tetra-
iodo-3-isoxanthone. It is a brown powder,
OH SOaNa
which is soluble in water (9 percent at
25°C) to give a cherry-red solution. It is
readily soluble in glycols and glycerol (20
percent at 25°C) and in ethanol (95 percent),
giving a solution that has a slight fluo-
rescence. Erythrosine is only fairly light-
resistant. It is insoluble in acid media, hence
SOaNa its use is limited.
Amaranth is the trisodium salt of 1- FD&C Red 4 (Ponceau SX) CI 14700
( 4-sulfo-1-naphthylazo )-2-naphthol-3,6-di-

H,C-¢=~=Nk
sulfonic acid. It is a reddish-brown
powder, soluble in water (20 percent at
25°C) to yield a magenta-red to bluish-red
solution. It is readily soluble in glycerol
(18 percent at 25°C), but poorly soluble
in glycols and ethanol (95 percent ethanol:
NaOaS yv SOaN a
5 percent water). Amaranth is moderately
light-stable and is very stable in acid media. Ponceau SX is the sodium salt of 2-
Amaranth has not been permitted for food (5-sulfo-2, 4-xylylazo )-1-naphthol-4-sulfonic
use in the United States since it was delisted acid. It is a red powder, easily soluble
in 1976, but may be returned to use since in water (11 percent at 25°C) to give an
there has been no demonstrated safety orange-red solution. It is readily soluble in
problem with it. glycerol (5.8 percent at 25°C), less so in
Carmoisine (Azorubrine) CI 14720 glycols and only slightly soluble in ethanol
(95 percent). It has a good light-resistance
and is very stable in acid media (pH 3). This
color is no longer permitted for use in foods
in the United States, as published in the
Federal Register September 23, 1976.
Ponceau 4R (Cochineal Red A) 16255

OH
Carmoisine is the disodium salt of 2-( 4-
sulfo-1-naphthylazo )-1-naphthol-4-sulfonic NaOaS-o-N=N
acid. It is a red powder, which is soluble in
water (4 percent at 25°C) to give a bright
magenta solution. It is only moderately
0 NaOaS
794 Source Book of Flavors

Ponceau 4R is the trisodium salt of Ponceau MX CI 16150

1- (4-sulfo-1-naphthylazo)-2-naphthol-6, 8- Ponceau 3R CI 16155
disulfonic acid. It is a red powder, soluble in Ponceau 6R* CI 16290
water (5 percent at 25°C) to give a scarlet- RedFB CI 14780
red solution. It has good light resistance and Red 6B CI 18055
is stable in both acid and alkaline media. It Red lOB CI 17200
has only a fair resistance to S02 • Scarlet GN* CI 14815
Red 2G CI 18050
OH flj -<"0(11~
*Classified by the Joint FAO/WHO Expert
Committee as toxicologically not acceptable

0·-·~ for use in food.

~·~~
Red 2G is a monoazo compound. It is a
red powder, which is soluble in water (6
percent at 25°C) to give a bright red solution
with a slight bluish tinge. It is fairly soluble
in glycerol, but only very slightly so in
ethanol (95 percent). Red 2G has excellent
light-fastness and is stable in both acid and
alkaline media. This color is not permitted
for use in food in the U.S.
Red No 40. (A/lura Red AC) CI 16035
OCHa OH
NaO,S-9-N=N
CHa
SOaNa
FD&C Red 40 is a dark red powder,
which is very soluble in water. It was added
to the permitted list of food colors in the
United States in 1971. Red No 40, with the
addition of various shading colors, can be
used satisfactorily to replace amaranth in
most food products. It is most effective in
opaque and translucent products, but does
not give the right shade of red in transparent
products.
Other red dyes The following other red
food colors have been used in various
countries, but are of much less importance
than those already described:
Fast Red E* CI 16045
Yellow Colors
FD&C Yellow No. 5 (Tartrazine) CI
19140 Tartrazine is the trisodium salt
of 3-carboxy-5-hydroxy-1-sulfophenyl-4-p-
sulfophenylazopyrazole. It is an orange-
yellow powder, which is very soluble in
water (20 percent at 25°C) and glycerol (15
percent at 25°C) but much less so in the
glycols (7 percent at 25°C). It is almost
insoluble in ethanol (95 percent). The solu-
tions are golden-yellow and have good light
stability. Tartrazine is very stable in acid
and weakly alkaline media, but in the pre-
sence of strong alkalis it acquires a deeper
reddish hue. It has been necessary to label
the presence of this color specifically, since
it is structurally related to aspirin and a
small segment of the population is allergic
(47,000-94,000 people in the U.S.) to it
(Frick and Meggos 1988).
D&C Yellow No. 10 (Quinoline Yellow)
CI 47005
0
~~'
v--c ;cH
~---(SOaNa)2
---1:::: N~
II
0
or
Quinoline Yellow is the disodium salt of
2-(2-quinolyl)-1, 3-indandione disulfonic
acid. It is a yellow powder, which is soluble
in water and glycerol to give a bright greenish-
yellow solution. It is only slightly soluble in

ethanol (95 percent). Quinoline yellow has
good light-resistance and is very stable in
acid media and in the presence of S0 2 ; it is
only poorly stable in alkaline media and
fades with benzoic acid. It is permitted for
use in the EEC countries. The color is used
widely throughout Europe and Central and
South America. It is currently not permitted
for use in foods in the United States, but this
may change.
FD&C Yellow No.6 (Sunset Yellow FCF)
CI 15985 Sunset yellow is the disodium
salt of 1-p-sulfo-phenylazo-2-naphthol-6-
sulfonic acid. It is an orange powder, readily
soluble in water and glycerol (both 19
percent at 25°C) to give an orange-yellow
solution. It is poorly soluble in the glycols
(2 percent at 25°C) and almost insoluble in
ethanol (95 percent). The color is light-fast
and has good stability in both acid and
alkaline media, but fades badly in the pre-
sence of S0 2 . It has good stability with
benzoic acid and is a widely permitted food
colorant.
Other yellow colors The following other
yellow food colors have been used in various
countries, but are of less importance than
those already described:
Chrysoin CI 14270
Fast Yellow AB * CI 13015
Naphthol YellowS CI 10316
Yellow RFS CI 13011
Yellow RY CI 14330
Yellow 2G CI 18965
*Classified by the Joint FAO/WHO Expert
Committee as toxicologically not acceptable
for use in food.
Green Colors
FD&C Green No. 3 (Fast Green
FCF) CI 42053 Fast Green is the disodium
salt of 4-{[ 4-(N-ethyl-p-sulfobenzylamino )-
phenyl] - (4- hydroxy- 2- sulfoniumphenyl) -
methylene }-1[ (N-ethyl-N-p-sulfobenzyl)-~2,
5-cyclohexadienimine]. It is a dull green
powder, which is very soluble in water,
glycerol and the glycols (all at 20 percent at
Food Colorants 795
25°C) but almost insoluble in ethanol (95
percent). There is slight fading of color in
acid media.
FD&C Green No. 1 (Guinea Green) CI
42085 This dye is of the triarylmethane
type and has a structural formula basically
similar to that of Fast Green. It is a dull
green powder, which is very soluble in
water, glycerol and the glycols (all at 20
percent at 25°C) and slightly soluble in
ethanol (95 percent). The color is light-fast,
has good stability in a wide range of pH, and
is stable in solutions of sodium benzoate,
but fades badly in the presence of S0 2 .
Guinea green is no longer permitted for use
in food in the United States.
Food Green S (Woo/green B) CI 44090
Food Green S is a triarylmethane dye
having a structural formula closely similar to
that of Fast Green. It is the mono sodium
salt of 4, 4-bis (dimethylamino )-diphenyl-
methylene-2-napthol- 3, 6-disulfonic acid. It
is a dull bluish-green powder, soluble in
water (8 percent at 25°C) but only slightly
soluble in glycerol and ethanol (95 percent).
It has poor light-stability, but is quite stable
in acid media and in the presence of S02 .
This color is not normally used alone, but is
a useful component of green shades.
Blue Colors
FD&C Blue No. 2 (lndigotine) CI 73015
lndigotine or indigo carmine is the disodium
salt of indigotin-5, 5' -disulfonic acid and is a
bright blue powder. It is only moderately
soluble in water (1.6 percent at 25°C), a
little less so in glycerol (1 percent at 25°C)
and very poorly soluble in either the glycols
or ethanol (95 percent). It has poor stability
and fades in acid media. It is fully accept-
able for use in foods.
FD&C Blue 1 (Brilliant Blue FCF)
CI 42090 Brilliant Blue FCF is a tri-
arylmethane dye having a structural for-
mula similar to that of Fast Green. It
is the disodium salt of 4-{ 4-(N-ethyl-p-
sulfobenzylamino- phenyl)- (2- sulfonium-
phenyl)-methylene}- [1-(N -ethyl-N -p-sul-
fobenzyl)-~2, 5-cyclohexadienimine). It is a
796 Source Book of Flavors
bright blue powder, which is very soluble in
water, glycerol and the glycols (all at 20
percent at 25°C) and is slightly soluble in
ethanol (95 percent). This color is light-fast, group is replaced by a -N(CH3h group.
and has good stability in a wide range of pH
and in the presence of so2 and sodium
benzoate.
Patent Blue V (Cl Acid Blue 3) CI 42051
Ca ++
2 are approved for specific uses as noted.
Patent Blue V is the calcium salt of
m-hydroxy-tetraethyl-diaminotriphenyl
carbinyldisulfonic acid. It is a bright blue
powder, very soluble in water (15 percent at
25°C), soluble in glycerol and fairly soluble
in ethanol (95 percent). It is very light-fast
and is heat stable, but acquires a greener
shade in acid media and in the presence of
so2 and sodium benzoate.
Other Blue Colors
The following other blue food colors are
permitted or have been used in various
countries:
Blue VRS CI 42045
*Indanthrene Blue CI 69800
*Classified by the Joint F AO/WHO Expert
Committee as toxicologically not acceptable
for use in food.
Violet Colors
FD&C Violet No. 1 (Violet No 1) CI
42640 Violet No. 1 is sometimes known as
Wool Violet 5BN. It is a triarylmethane dye
and has a structural formula similar to that
of Fast Green, except that the hydroxyl
Chemically, it is the monosodium salt of 4-
{[ 4-(N -ethyl-p-sulfobenzylamino )-phenyl]-
[4 - (N - ethyl - p - sulfoniumbenzylamino) -
phenyl]-methylene }-(N<N-dimethyl-Ll, 2,
5-cyclohexadieneimine). It is a bright violet
powder, which is very soluble in water,
glycerol and the glycols (all at 20 percent at
25°C), and is slightly soluble in a wide range
of pH. It fades critically in the presence
of S0 2 , but is stable in sodium benzoate
solution.
Violet 6B This is classified by the Joint
FAO/WHO Expert Committee as toxico-
logically unacceptable for use in food.
Orange Colors
There are no orange colors approved for
general food use. The following two colors
Orange B
The color component of Orange B
is the disodium salt of 1-(4-sulfophenyl)-
3- ethylcarboxy- 4- (4- sulfonaphthlazo)- 5-
hydroxypyrazole. This color is approved
only for the coloring of casings or surface of
frankfurters. The concentration of this color
cannot exceed 150 ppm in the finished food
(by weight).
Citrus Red #2
n
OCH 3 HO
h
v·~-·~v
v
H3 CO
The color additive is principally 1-(2,
5-dimethoxyphenylazo )-2-naphthol. Citrus

Red No 2. shall be used only for coloring
skins of oranges that are not intended for
processing.
Other Colors
Brilliant Black PN (BN) CI 28440
Na03S-o-;\J=Nq-N=N ~-CO·CH3
Na0 3 S~
S0 3Na
S0 3Na
Brilliant Black PN is the tetrasodium
salt of 2-4-(p-sulfophenylazo )-7 -sulfo-1-
naphthylazo-8-acetamino-1-naphthol-3, 5-
disulfonic acid, and is a dense black powder,
which is readily soluble in water and gly-
cerol but only slightly soluble in ethanol (95
percent). Brilliant Black has excellent light-
fastness and is stable in acid media and
under heat treatment. Although a general
purpose food color, it is used mostly in
blends. It is not permitted for use in foods in
the U.S.
Chocolate Brown HT (CI Food Brown 3)
CI 20285 This is a diazo dye that is used
for the coloring of vinegar. It is very soluble
in water and has excellent stability in acid
media.
Forms of the FD&C Dyes
The FD&C Dyes are available in a variety
of forms. Each of these forms has a specific
application. The most commonly used forms
of the dyes are discussed below.
Powder
Powdered dyes have the advantages of
being the least expensive, dissolve readily
in water, blend well in dry mixes and have
broad general application. Disadvantages
include poor flow properties and potential
dusting problems.
Liquid
The color has been dissolved by the manu-
facturer in water, propylene glycol or
glycerol and thus this step is saved for the
end user. This color form has the advantages
of being dust-free and generally exhibits few
Food Colorants 797
quality control problems. Liquid colors are
more expensive and require more storage
space than the dry forms.
Granules
Granules are manufactured by either drying
the color as a cake and then grinding to
the desired particle size, or agglomerating
the powdered dye. The primary benefit
of the granulated form is a reduction in dust
problems. Granulated colors have disad-
vantages in variable availability, too-large
particle size for use in dry mixes and ex-
truded products, and are more expensive
than powdered colors. While the granulated
form is not as dust-free as the liquid form, it
is somewhat less expensive.
Plating Dyes
Powdered dyes are not particularly well-
suited for the coloring of dry mixes. The
plating dyes are specially manufactured (a
very small particle size) to yield a product
that can both color the dry mix and act
as a dye once the product is reconstituted.
The small particle size would result in dust
problems and a higher cost.
Nonftashing Blends
A simple blend of powdered dyes will
initially show the individual colors when it
is added to water. For example, a brown
blend will show streaks of red, yellow and
blue. This is the result of nonuniform
blending and variable rates of dissolution of
the blended dyes. This problem is overcome
by having the manufacturer dissolve the
blended dyes and then redrying them
together.
Paste
The paste form is desirable in some food
products (e.g., icings, hard candies and cake
decorations). It is made by dissolving the
dye( s) in a solvent and then adding a gum to
increase viscosity.
Dispersions
Dispersions are made by suspending a dye
798 Source Book of Flavors

TABLE 19-2. Blend Formulas for Certified Primary FDC Colors (Heath 1981)

Water-Soluble FD&C Colors, Parts by Wt.

Blue Red Red Red Yellow Yellow Blue

Shade No.1 No.2 No.3 No.40 No.5 No.6 No.2

Black" 12.3 7.3 26.8 53.6

Deep blue 60 40
Brown
Caramel 5 26 49 20
Chocolate 7.5 28 26.5 38
Greenb
Medium green 35 65
Mint green 45 55
Lime 99
Orange<
Medium 3 27 70
orange 10 90
Amber 100
Orangeade
Graped
Bluish Grape 15 85
Reddish 10 90
grape 12 58 30
Wine
Rede
Cherry 60 40
Strawberry 83 3 14
Pink 95 5
Yellowf
Egg 85 14
Lemon 100

• Great care and accuracy must be exercised in blending the colors to produce a black shade as very slight
variations will throw the shade off.
bBlends of FD&C Blue No. 1 and FD&C Yellow No.5 will produce almost any shade of green.
<Blends of FD&C Yellow No.6, FD&C Yellow No.5, and FD&C Red No. 40 will produce almost any shade of
orange. Increasing the amount of FD&C Yellow No. 5 in the blends will cause the shade to become lighter and
yellower, and increasing the FD&C Red No. 40 will cause the shade to become deeper and redder.
d Blends of FD&C Red No. 2 and FD&C Blue No. 1 will produce almost any shade of grape.
e By mixing FD&C Red No. 2, FD&C Red No. 40, and FD&C Red No. 3 and adding small amounts of FD&C
Yellow No. 5, FD&C Yellow No. 6, and FD&C Blue No. 1, almost any shade of red may be produced.
f Addition of FD&C Red No. 2, FD&C Red No. 40, and FD&C Yellow No. 6 to FD&C Yellow No. 5 will produce
variations in yellow shades that are usually used.

in a liquid carrier, often adding titanium through the proper blending. Some blends
dioxide as an opacifying agent. are listed in Table 19-2.

Blending of FD&C Dyes Oil-soluble Dyes

For the average manufacturer of food pro- There are no certified oil-soluble colors
ducts, the primary dyes available are suf- listed for food use; however, since 1959 the
ficient to give the necessary shade of color lakes of the FD&C water soluble colors
 Food Colorants 799

have been permitted and are used as pig-
ments dispersed in edible fats and oils to
color nonaqueous food products. These
food color lakes are made (in accordance
with FDA regulations) by the reaction of a
certified water-soluble color with the basic
radical aluminum or calcium, while ex-
tending the resulting salt on a substratum of
alumina. For use of these lakes the pigment
color must be very finely ground and must
be mixed with the fat or oil to obtain maxi-
mum strength and shade as well as uniformly
colored product.
Lipid-based foods may also be colored by
using water-soluble food colors emulsified
in the oil or fat, or by using one of the listed
oil-soluble colors obtained from natural
sources (turmeric, curcumin, annatto, and
carotene) as well as synthetic ~-carotene
and 8-apocarotenal.
Preparation of FD&C Dye Solutions
Water-soluble Colors
Water is brought to a boil and cooled to
80°C (180°F). A weighed amount of color
is added slowly with constant stirring until
complete solution is obtained. Four ounces
of color dissolved in a gallon of water
(3 percent soln) is usually used as a stock
solution. If a stronger concentration is
desired, care must be taken not to exceed
the maximum solubility (see Table 19-3 for
approximate values). Distilled water should
be used in order to prevent precipitation of
the color due to the presence of metallic
ions in solution. Glass or enameled con-
tainers should be employed, as metals
have a decolorizing action on some of the
certified colors. If the color solution is not
for immediate use, a preservative, such
as sodium benzoate, alcohol, glycerol or
propylene glycol, should be used.
Oil-soluble Colors
A weighed amount of oil-soluble color is
added slowly with constant stirring to 70-80
percent of the amount of oil to be used,
which has been preheated to 65°-70°C
(150°-l60°F). When completely dissolved,
the solution is cooled to room temperature
and the balance of the oil is added with
thorough stirring. A quantity of color
greater than that required to give maximum
concentration should not be used. For
example, in mineral oil at (70°F) the ap-
proximate maximum concentration of D&C
Red No. 17 is 1 oz./gal. and that of D&C
Yellow No. 11 is 0.1 oz./gal.

TABLE 19-3. Solubilities of FDC Colors in g/100 ml Solvent•

Ethyl Alcohol Glycerol Propylene Glycol

Water
FD&CColor at 25°C 95% 50% 100% 50% 100% 50%
FD&C Blue No. 1 18.7 1.5 20.0 20.0 20.0 20.0 20.0
FD&C Blue No. 2 1.1 0.2 1.0 1.0 0.1 0.4
FD&C Green No. 1 24.9 4.5 8.3 20.0 20.0 20.0 20.0
FD&C Green No.2 15.0 1.1 8.3 20.0 20.0 20.0 20.0
FD&C Green No. 3 24.9 0.4 6.8 20.0 20.0 20.0 20.0
FD&C Red No. 2 17.2 0.5 18.0 12.0 1.0 2.4
FD&C Red No.3 8.5 13.2 3.9 20.0 16.0 20.0 6.6
FD&C Red No. 4 7.5 1.5 5.8 4.2 2.0 2.6
FD&C Violet No. 1 18.7 1.5 20.0 20.0 20.0 20.0 20.0
FD&C Yellow No.5 20.0 3.0 18.0 20.0 7.0 12.4
FD&C Yellow No.6 25.3 1.0 20.0 20.0 2.2 7.0
•The published solubility tables of the certified FD&C colors are only approximate and differ widely. The maximum solubility of a
given color varies from batch to batch and depends upon the relative amounts of salt, pure dye, and moisture content of the color in
question.
800 Source Book of Flavors

The use of Preservatives in Dye Solutions
Alcohol may be used for dilute solutions
such as household colors. Ten percent
(13 oz. to each gallon) is satisfactory.
Alcohol should not be used in concen-
trated solutions as it affects the solubility of
certified colors.
Sodium benzoate is a weak preservative
and best results are obtained in acid solu-
tions. Use 1/8 oz. dry sodium benzoate in
conjunction with 1/4 oz. dry fruit acid to
each gallon of color solution. One-tenth of
1 percent sodium benzoate without acid has
very little preservative value.
Glycerin or propylene glycol may be
used, but at least 25 percent by volume is
needed to ensure the keeping qualities of
color solutions.
Maximum Usage of the FD&C Dyes
The recommended maximum usages given
in Table 19-4 are, in most cases, greatly in
excess of the proportions that are normally
used. Only a fraction of the amounts in-
dicated should be necessary to produce
satisfactory color in the finished product.
However, concentrates, extracts and other
similar preparations are not considered
finished products, due to the fact that they
are reduced considerably before they are
converted into a finished food product.
Problems with the FD&C Dyes
Light, acids and alkalis may act on certified
colors, causing various reactions, such as
fading or changing of shade. The following
elements should be avoided as much as
possible: excessive sunlight, bleaching
agents (sulfur dioxide being the most
common), and tin and iron. These are the
most common offenders in causing a re-
ducing action, with resultant fading of color
solutions.
Crystallization of the sugar, as the water
dries out, is the most common cause of the
so-called fading of colored candy. The color
is not destroyed. It simply has an affinity for
other parts of the candy and thus the color
migrates. Impurities in glucose may also
cause colors to fade.

TABLE 19-4. Recommended Maximum Color Usages (Heath 1981)

%Color as Approximate Amount of Color per 100 Lb g per 100 Lb of Finished

Certified of Finished Food Equal to 0.03% (oz) Fooda Equal to 0.03%

95 112 14.3
90 112 15.1
80 315 17.0
70 7/10 19.4
60 4/5 22.7
55 9110 24.7
50 1 27.2
45 1 1110 30.2
40 1 1/4 34.0
35 1 2/5 38.9
30 1 3/5 45.3
25 2 54.4
20 2 1/2 68.0
15 3 1/5 90.7
10 5 136.0
5 10 272.1
4 12 1/2 340.2
3 16 3/5 453.6
2 25 680.4
50 1,360.8
'For those who desire greater accuracy, these calculations were made on the exact proportions-
13.608g of 100% of color per lOOlb of finished foods= 0.003%.
 Food Colorants 801

TABLE 19-5. Possible Problems with FDC Dyes (Frick and Meggos 1988)

Problem Possible Cause(s)

Precipitation from color solution • Exceed solubility limit.

or from colored liquid food.
Dulling effect instead of pleasing
shade.
Specking and spotting during
coloring of bakery and
confectionery products.
Fading of color
Fading due to retorting with
protein material.
Poor shelf life with colored,
canned carbonated beverages.
• Chemical reaction.
• Low temperatures, especially for concentrated color solution.
• Excessive color.
• Exposure to high temperature.
• Color not completely dissolved in making solution.
• Employed liquid color containing sediment.
• Attempted dispersion of an aqueous color solution in products
containing excessive fat.
• Colored products not protected from sunlight.
• Color solutions or products in contact with certain metals (zinc, tin,
aluminum) during dissolving, handling or storing.
• Color-preparing facilities not thoroughly cleaned to avoid
contamination with reducing organisms.
• Processing temperature too high.
• Contacted color oxidizers such as ozone or hypochlorites, or reducers
such as sulfur dioxide or ascorbic acid.
• Presence of strong acids or alkalies during the coloring of certain
foods.
• Color is unstable under these conditions.
• Use of an excessive amount of certified azo-type dye.

Color should be added to ice cream in the
freezers, or when the mix is ready for the
freezers. Thus, there is less possibility
of bacterial contamination. Contact with
metals should be avoided as much as
possible. If stock solutions are prepared,
they should be adequately preserved or
kept in a cool place to prevent bacterial
contamination.
Additional problems and solutions have
been presented by Frick and Meggos
(1988), and a table from their publication is
presented as Table 19-5.
Lakes
Lakes and Dyes-Differences
Dyes are colored chemical compounds that
exhibit their coloring power or tinctorial
strength when dissolved in a solvent.
Lakes are insoluble materials that color by
dispersion.
The FD&C lakes consist of a substratum
of alumina hydrate on which the dye is
absorbed or precipitated. Prior to use of
the lakes, colorants were made for some
applications by absorbing dye solutions on
insoluble material such as starch, cellulose,
etc. These can be highly colored materials,
but are of lower coloring power and perform
poorly as pigments.
The physical properties of the water-
soluble colors (dyes) are of small signi-
ficance in most products. There is, for
example, a choice between granular or
powdered forms of dye. Dissolved, both
forms produce equivalent solutions. Dyes
from different manufacturers are inter-
changeable for most uses. That is not always
true with lakes, even though they may be
the same in pure dye content. Shades of
difference can exist from one manufacturer
to another. Particle size is of critical im-
portance, and the product should pass
through a 325-mesh screen when wet-tested.
Some differences in the properties of dyes
and lakes are shown in Table 19-6.
The tinctorial strength of a water-soluble
802 Source Book of Flavors
color is proportional to the pure dye con-
tent. Thus, two units of a 45 percent pure
dye color are equivalent in color strength
and shade to one unit of a 90 percent pure
dye color. This is not true with the lakes.
One unit of a 24 percent pure dye lake is not
equivalent in strength or shade to two units
of a 12 percent pure dye color. Variation of
shade with pure dye FD&C Yellow No. 5
lake, for example, is: 5 percent pure dye,
Lemon Yellow; 15 percent, Egg Yellow;
and 25 percent, Orange-Yellow.
The lakes are insoluble in nearly all
solvents. When suspended in water, there is
a slight "bleed" of dye into the water,
but for most food applications this is of no
consequence. The lakes are stable in the pH
range of 3.5 to 9.5. Outside this range, the
substratum breaks down, releasing the dye.
The color regulations classify the FD&C
lakes as straight colors, subject to certi-
fication. Also, they must be made from dyes
that have been previously certified.
In most cases, the color regulations
specify a minimum of 85 percent pure dye
for primary dyes. However, most lots will be
in the range of 90 to 93 percent pure dye.
The FD&C lakes do not have a specified
minimum dye content and range from 10
percent to 40 percent in pure dye.
Lakes are suitable for coloring products
that are lipid-based and products where use
of water is undesirable.
TABLE 19-6. Properties of Dyes and Lakes (Heath 1981)
Solubility
Method of coloring
Pure dye content
Rate of use
Particle size
Stability
Light
Heat
Coloring strength
Shade
Uses ofLakes
Table 19-7 lists a number of products that
are easily colored with the FD&C lakes.
Compound coatings, generally mixtures
of fat and sugar, are used extensively in the
candy and baking industry. They can be
colored with FD&C dyes by use of a non-
aqueous solvent, such as propylene glycol
or glycerol. Often, lecithin is required to
emulsify in the color. The use of glycerol or
glycol involves a rather difficult dissolving
operation, and inclusion of these solvents
sometimes changes the characteristics of the
coating. A number of these coatings can be
colored by direct addition of lakes with
agitation. In some instances, it is necessary
to predisperse the lakes in a liquid to avoid
specking.
Sandwich-cookie fillings can be colored
easily with lakes. Addition of the lake can
be made to the finished product or may be
incorporated with the dry ingredients.
The use of lakes in pan coating has been
of great interest, both in aqueous sugar
coatings and nonaqueous, film-type coat-
ings. Use of lakes alone gives results similar
to the water-soluble dyes, i.e., the depth of
color is proportioned to the number of
coats. Addition of an opacifying agent such
as titanium dioxide produces a coating that
is independent of the number of coats and
produces tablets free of mottling that results
from surface indentations.
Lakes Dyes
Insoluble in most solvents Soluble in water,
propylene glycol,
glycerin
By dispersion By being dissolved
Generally 10-40% Primary colors-90-93%
0.1 to 0.3% 0.01 to 0.03%
Average 5 microns 12 mesh to 200 mesh
Better Good
Better Good
Not proportional to pure dye Directly proportional to
content pure dye content
Varies with pure dye content Constant
 Food Colorants 803

TABLE 19-7. Suitability of Lakes and Dyes for Given Applications (Heath 1981)

Product Lakes Water-Soluble Colors

Hard candy Not suitable Suitable

Striped candies (mints, etc.) Reduces color bleed Suitable
Compound coatings Easily incorporated Require dissolving in glycerin
or propylene glycol
Sandwich-cookie fillings Easily incorporated Suitable
Icings, marshmallow coatings For Pink using Red #3-the lake Suitable-Red #3 not light
is more light fast stable
Sugar coatings-gum, tablets Suitable Suitable
Inks, plastics, food can linings, Suitable Not suitable
film
Cake mixes Suitable Suitable-do not contribute
much color to the dry mix
Carbonated beverages Not suitable Suitable
Compressed tablets Very good Suitable-requires
granulation operation
Solid fats and waxes Suitable Not suitable
Dry mix products-soft drink Not suitable Suitable
powders, gelatin desserts
Chewing gum Suitable-leaves colored cud Suitable

Another area of great interest in lakes is noncrystalline powders, such as starch or

compressed-tablet operations. Use of dyes
involves addition of a solvent, generally
water. Removal of the water often results in
chromatographic separation of the color. If
a blend, this produces a separation of the
component colors. If a single dye, variable
shades are brought about by migration of
the dye. The lakes can be incorporated dry
and the material directly compressed. To
obtain the same depth of color, 7 to 10 times
as much lake as dye is required.
Dispersion
Dispersion is the distribution of the pigment
throughout the material to be colored. The
dispersion of pigment is: (1) breaking up
of the agglomerates and (2) wetting and
coating each particle with the vehicle in
cases where the material to be colored is
liquid (vehicle).
For most food and pharmaceutical ap-
plications, high-shear mixers are adequate
for lake dispersion in liquids.
Many lake applications demand dis-
persion in dry materials. In crystalline
materials, simple mixing sets up sufficient
attritive forces to obtain dispersion. In
flour, it is often necessary to prepare a
concentrated premix of 5-10 parts powder
to 1 part of lake, followed by grinding
through a hammer mill. This concentrated
premix is easily incorporated into the final
mix.
NATURAL COLORANTS
Both plants and animals are prolific in the
wide variety of colors that they display; but
from the point of view of natural coloring
materials for use in foods, beverages, etc.,
only those of plant origin are of interest.
These range through the whole spectrum of
colors, from the ubiquitous green of leaves
to the multitudinous hues and shades of
color exhibited by flowers and other plant
tissues. Recent trends in consumer attitudes
and a growing concern over the safety of all
food additives, together with a continuing
uncertainty over the interpretation of toxi-
cological data, have led to increasingly
restrictive legislation governing the use of
synthetic food colorants in foods. Market
pressure for "natural" labels and consumer
opinion that natural materials are safer has
804 Source Book of Flavors

increased the demand for natural colorants Fruit juice

(Spears 1988). Paprika and paprika oleoresin
Riboflavin
Saffron
"Permanently Listed" Natural Food
Turmeric and turmeric oleoresin
Colorants
Toasted partially defatted cooked cotton-
Regulations Regarding Usage seed flour
Vegetable juice
For Use in Foods Generally Consistent with
Good Manufacturing Practice (GMP): For Use in Foods Generally, but not to
Annatto extract Exceed the Stated Amounts:
Caramel P-Apo-8' -carotenal 15 mg/lb. of food
P-Carotene Canthaxanthin 30mg/lb. of food
Carrot Oil Titanium dioxide 1 percent by weight of
Cochineal extract and carmine food
Dehydrated beets

TABLE 19-8. Sources of Natural Colorants (Heath 1981)

Principal Color
Source Botanical Name Components Color

Alfalfa Medicago sativa L. Chlorophyll-a and ·b, lutein Green

Alkannet (anchusa) Alkanna tinctoria L. Alkannin (orcanella) Red
Annatto Bixa ore/lana L. Bixin Yellow
Beet Beta vulgaris L. Betalains (betalin) Red
Betel nut Brazil wood Coesalpinia braziliensis Brazilin Red-orange
Calendula Calendula officina/is L. Calendulin Yellow
Carrot Daucus carota L. a- and ~-Carotene Yellow
Catechu (betel nut) Acacia catechu Willd. Red-brown
Cochineal (carmine) Dactylopius coccus Costa. Carminic acid Red
Cranberry Vaccinium macrocarpon Ait. Cyanidin Red
Cudbear Locanora acharius and other
lichens
Grape Vitis vinifera L. Malvidin, anthocyanins Purple-red
Grass and green leaves Chlorophyll-a and -b Green
Kino Pterocarpus marsupium Roxb. Red
Litmus Lecanora tartarea & oth lichens zolitmin Red
Logwood Haematoxylon campechianum Haematin Blue
Marigold Tagetes patwiah and other spp. Zoaxanthin Yellow
Orange peel Citrus sinensis (L.), Osbeck Violaxanthin Yellow
Orchil Rochella, Variolana & oth.lichens Orchin, orcein Violet
Paprika Capsicum annuum L. Capsanthin, capsorubin Red, orange
Persian berry Rhamnus frangula L. Rhamnetin Red
Quercitron Quercus tinctoria L. Quercetin Yellow
Red beet Beta vulgaris L. Betalains (betanin) Red
Red Sanderswood Pterocarpus santalinus L. Santalin-A and -B Red
Roselle Hibiscus sabdaritta L. Cyanidin Red
Safflower Carthamus sativus L. Safflor yellow, carthamin Yellow
Saffron Crocus sativus L. Crocin, crocetin Yellow
Tangerine Citrus reticulata Blanco. ~-Cutrabub Orange
Turmeric Curcuma longa L. Curcumin Yellow
Yellow corn Zeamays L. Zeaxanthin, cryptoxanthin Yellow

For Use only as Indicated:
Grape skin extract (enocianina):
In still and carbonated beverages and
alcoholic beverages
Grape color extract:
In nonbeverage foods
Ferrous gluconate:
For coloring ripe olives, consistent with
good manufacturing practice.
Source and General Description
The principal sources of natural coloring
materials are given in Table 19-8 (Heath
1981). This does not in any way imply that
they are permitted for use in foods, and
reference must be made to the appropriate
legislation.
Alkanet
Alkanet is the coloring matter derived from
the roots of Alkanna tinctorial Tausch
(Anchusa tinctoria Lam.), a tree indigenous
to the Mediterranean region, which grows in
Hungary and western Asia. The coloring
principal is alkannin, which can be re-
covered by extraction with petroleum ether.
Alkannin (or orcanella) is a naphtha-
quinone derivative and is dark reddish-
brown, somewhat coppery crystalline
powder. It is insoluble in water, but soluble
in ethanol (95 percent) and fixed oils to give
CH;, CH;,
~ I ~ I
H;,COO·C-~ /~ /C~ /C~
c' C ~C Y
I
H
I
H
I
H
I
H
Food Colorants 805
a bright red solution. In alkaline solution,
the color changes to a deep blue.
Annatto
Annatto is the fruit of a shrub, Bixa ore/lana
L., which is cultivated in South America,
the southern United States (Louisiana),
India and East Africa. The principal color-
ing matter is recovered by pulping the
pericarp of the fruits with water, allowing
the mass to ferment and filtering out the
insoluble annatto which is then sundried
into cakes. These contain 6-12 percent of
the coloring principal, bixin.
Bixin is a carotenoid and chemically is
the monomethyl ester of norbixin, a sym-
metrical dicarboxylic acid. It is insoluble in
water and only slightly soluble in ethanol
(95 percent) but readily soluble in organic
solvents and fixed oils to give a brownish-
yellow solution. Alkalis saponify bixin
giving a clear reddish-brown aqueous
soluble solution; this is the alkali salt of
norbixin.
Annatto is marketed as a light-yellow to
deep orange spray-dried powder (15 percent
bixin), as a solution in vegetable oil (0.25-
0.5 percent bixin), or as a water-soluble
form. This latter product is normally in
potassium hydroxide/propylene glycol
solution with a pH in excess of 8. Some
products may contain polysorbate (Tween
80) and this is stated in the specification.
Most water-soluble annatto products con-
tain 1.5-2.5 percent bixin or are stan-
dardized on a color value.
Annatto is permanently listed in the
United States as a color additive for use
in foods and is widely employed in the
manufacture of butter, margarine, cheese
and related products (Francis 1987).
~ ~ ~ ¥ ~
/ '
~<:("
~ _.A~/~
~c(" ~C
'
~C/ ~CHCOOH
I
H
I H
I I
 806 Source Book of Flavors
TABLE 19-9. Principle Anthocyanins of Value as Food Colorants (Heath 1981)
Chemical structure
Anthocyanidin Chemical Formula
Cyanidin C, 5 H,,0 6CL
Delphinidin C,sHll07CL
Mal vi din C 17 H 15 07CL
Pelargonidin C, 5 H"0 5 CL
Peonidin C,6Hu06CL
Petunidin C,6Hu07CL
Anthocyanins
Most of the red and blue colors of flowers,
leaves and fruits are due to the presence of
anthocyanins. These are intensely colored,
water-soluble glycosides of 2-phenylbenzo-
pyrylium salts. The aglycone moiety is
known as an anthocyanidin. The color hue
and light stability characteristics are de-
pendent on the hydroxyl and methyl groups
as well as the nature of the glycoside link-
ages involved. The glycoside moiety com-
prises one or more molecules of glucose,
galactose, rhamnose or arabinose. Some
anthocyanins are acylated with p-coumaric,
caffeic or ferrulic acids at the 3'-hydroxy
group of the sugar. The principal antho-
cyanins are listed in Table 19-9 and an
excellent review has been recently published
by Francis (1989).
The color of anthocyanins is dependent
on several factors. The removal of the
3'-hydroxy group shifts the color toward
yellow; methylation results in a reddening
effect. As the anthocyanins are ionic, they
are pH-sensitive; solutions at low pH are
bright red, those at high pH are bright blue
and intermediate shades result as the pH
alters. High concentrations of anthocyanins,
such as occur in the skins of many fruits,
result in a deep purplish to almost black
appearance.
Anthocyanins are traditionally recovered
from suitable plant material by extraction
with methanol, acidified with a mineral acid
Structural Formula
R= R'= Occurrence
OH H Peaches, cherries, plums, raspberries,
blackberries, red currants, black
currants, red cabbage
OH OH Blueberries, black currants, grapes
OCH 3 OCH 3 American grapes and hybrids
H H Strawberries, mulberries, red radish
OCH3 H Cranberries
OCH 3 OH American grapes
or a fruit acid such as tartaric, followed by
removal of the solvent under vacuum and
purification by ion-exchange chromato-
graphy. The acid remains in the final pro-
duct; hence, the use of tartaric acid makes
the product more widely acceptable for use
in foods where a red color is desired.
Anthocyanins are widely permitted
throughout the world for use as a food
colorant. In the United States, they may be
used only in the form of grape skin extract
(enocianina) and grape coloring. Grape skin
extract is made from the aqueous extraction
(steeping) of fresh deseeded marc remaining
after grapes have been pressed either for
juice or wine (CFR 21, 73.170). Grape
coloring is an aqueous solution of grape
pigments made from Concord grapes or a
dehydrated powder prepared from the
aqueous solution. The aqueous solution is
prepared by extracting the pigments from
precipitated lees produced during the
storage of Concord grape juice (CFR 21,
73.169).
Beet Powder
Beet or red beet (Beta vulgaris L.) contains
up to 0.15 percent water-soluble coloring
principals known as betalains. These com-
prise the red betacyanins and the yellow
betaxanthins. The major betacyanin of red
beet is betanine, which accounts for 75-95
percent of the total betacyanins present and
far exceeds the betaxanthins present.

H
Natural colorants derived from red beets
are readily available commercially and are
comprised of concentrated syrupy liquid
beet juice (40-60 percent total solids and
0.5-1 percent betanine) or spray-dried
powder (40 percent betanine or diluted to a
stated figure). Many of these products
contain ascorbic acid as a color stabilizer
and may also contain a permitted preser-
vative whose nature must be stated in the
specification. In view of the diversity of the
products available, reference should be
made to the manufacturer for advice on
coloring power and use levels.
The color of betanine is not affected by
pH within the range 3-7, but in alkaline
media above pH 7 the color intensity is
reduced and the hue changes from red to
violet. The color is relatively heat-stable
(Padival and Sastry 1985).
Caramel
Caramel is an amorphous brown product
resulting from the controlled heating to
about 190°C (352°F) of food grade carbo-
hydrates including: dextrose, invert sugar,
lactose, malt syrup, molasses, sucrose,
starch hydolysates and fractions thereof.
Most commercial caramel is produced from
liquid corn syrup (or glucose syrup) and, by
regulating the conditions, several different
grades can be produced. Food grade acids
(acetic acid, citric acid, phosphoric acid,
Food Colorants 807
sulfuric acid and sulfurous acid), alkalis
(ammonium hydroxide, calcium hydroxide,
potassium hydroxide and sodium hydrox-
ide) and salts (ammonium, sodium, or
potassium carbonate, bicarbonate, phos-
phate, sulfate or sulfite) may be employed
to assist carmelization in amounts consistent
with good manufacturing practice (CFR 21,
73.85). The preferred catalyst is ammonium
sulfite (North 1973; Woodroof and Phillips
1974).
The chemistry of the reaction that takes
place is complex, and depends not only on
the starting material and its concentration
but on the nature of any catalysts used and
the temperature and pH of the system.
There is considerable art in the manufacture
of food grade caramels. Although the
chemical reactions are not well under-
stood, two main types are thought to occur
(Greenshields 1973): (a) Maillard reaction
and (b) pure caramelizing reactions; both
produce aldehydes and dicarbonyls of high
molecular weight.
All caramels are aqueous, colloidal
in nature and are characterized by the
electrical charges that bind the particles
together. Depending on the method of
manufacture, these may be either positive
or negative. It is the isoelectric point, or pH
at which the ionic charge is electrically
neutral, which determines the most suitable
end use of the product. At a pH above the
isoelectric point the caramel is negatively
charged, and below this pH it is positively
charged. The following test for colloidal
character is described by North (1973):
Prepare a 1 percent tannic acid (USP) solution
and filter clear. Make a 1 percent solution of the
caramel in distilled water. To 13 ml of the
caramel solution, add 12 ml of the tannic acid
solution and mix well. If the caramel is negatively
charged, the solution will remain clear and bright
for at least 24 hr. A positively charged caramel
results in a precipitate.
Numerous other more specific tests for
colloidal character and isoelectric point are
reviewed by Greenshields (1973).
808 Source Book of Flavors
Caramel is purchased not only by type,
but by tinctorial power. This is determined
either by empirical tinctometer, compara-
tive methods or spectrophotometrically. It is
now a common practice to quote the tinctorial
power in terms of EBC (European Brewers
Convention) units (Ward 1973, 1976).
The following grades of caramel are
generally available, but in many countries
caramel is manufactured for specific end
uses:
Acid proof
Isoelectric point below 2.0
Single-strength, double strength, foaming
and powdered (spray-dried or drum dried).
Bakers
Isoelectric point 4.0 or higher.
Regular, positive-type chocolate brown,
burnt sugar flavor, powdered.
Spirit
Isoelectric point below 1.0
Distillers
The physicochemical characteristics of
commercial caramels are given in Table
19-10, and a review of caramel colors has
been presented by the British Caramel
Manufacturers Association (1988).
Caramel has been evaluated toxico-
logically by the Joint FAO/WHO Expert
Committee on Food Additives and those
products not made by the ammonia process
are listed with an unlimited ADI, whereas
caramel made by the ammonia process has
been given an ADI of 100mg/kg bw based
on a product having a color intensity of
TABLE 19-10. Physicochemical Characteristics of Commercial Caramels (Heath 1981)
Positive
Color intensity (EBC units) 50,000 ± 1,000
pH 4.2 to 4.5
Specific gravity 1.3 to 1.32
Dry solids content 65%
Viscosity at 25°C 200-300cps
Insoluble matter less than 3 mg/100 g
lsoelectric point (depending on pH5.0to7.0
method of manufacture and usage)
20,000 EBC units and containing not more
than 200 mg/kg of 4-methyl imidazole.
Being viscous, it is usual to dilute caramel
products before use to facilitate handling
and incorporation into product mixes. Such
dilutions are readily fermentable and must
be used as soon as possible after prepara-
tion. It is preferable to dilute only as much
as required at the time.
Carotene and Carotenoids
A wide variety of food products and color-
ing extracts owe their distinctive yellow
to reddish-yellow color to the presence
of carotenoids. These include annatto,
apricots, butter, egg yolks, paprika, saf-
fron, salmon, tomatoes, yellow corn, etc.
Carotene itself occurs in nature in four
isomeric forms: a, p, y and K, which differ
only in the position of the double bonds.
The carotenoids are a class of oil-soluble
yellow to violet-red isoprenoid lipochrome
pigments. They are present in plant and
animal tissues, either in solution in the fats,
as colloidal dispersions, or in combination
with proteins in the aqueous phase. Some
200 carotenoids have been characterized in
nature representing aliphatic or aliphatic/
alicyclic structures and a further 200 caro-
tenoid molecules have been synthesized in
the laboratory.
The basic chemical structure of the
carotenoids consists of two rings and an
extended system of conjugated double
bonds. Most have a C40 carbon skeleton
comprising a C18 central chain of 7 double
Caramel Type
Negative Spirit
26,000 ± 1,000 20,000 to 25,000
3.0 to 3.5 4.0 to 4.5
1.34 to 1.35 1.34 to 1.35
69% 70%
50-100cps 50-lOOcps
less than 3 mg/100 g less than 3 mg/100 g
pH4.0to6.0 belowpH3.0

bonds with 4 side chain methyl groups. The
characteristic absorption spectra of these
compounds is due to the conjugated double
bond system-as the chain lengthens, the
color changes toward red and as it shortens,
the change is toward yellow. In nature,
carotenoids are primarily all trans isomers
but cis isomers do exist. Modifications in
the structure of the carotenoid molecule
account for the characteristic color shades
associated with many plants. In food pro-
ducts that are colored with carotenoids, the
observed shade is more directly related to
the concentration and physical form of
the colorant than to its precise chemical
structure.
Chemically, the carotenoids are divided
into two classes: (a) those containing only
carbon and hydrogen and (b) the oxy-
carotenoids that contain oxygen in addition.
The following are of major importance as
natural food colorants: ~-carotene, ~-apo-
8'-carotenal, canthaxanthin and bixin.
CHI CHI
CHI
Food Colorants 809
P-Carotene: Consists of two a-ionone
rings joined through an isoprenoid chain of
conjugated C: C double bonds. It was first
synthesized by Roffman-LaRoche in the
early 1950's and still forms the basis of
commercial production. Pure ~-carotene
has a deep violet-red color and forms flat
platelet crystals. It is insoluble in water, but
is partially soluble and readily dispersible in
fixed oils and organic solvents to give a
lemon-yellow to deep orange-red solution,
depending on the concentration.
~-Carotene is available commercially
in various physical forms and coloring
strengths, including: liquid suspension (30
percent carotene), semisolid suspensions
(24 percent carotene), dry powder, fine
beadlets (10 percent carotene), gels and
emulsions (3 percent carotene). Water-
dispersible products are also available; these
produce optically clear aqueous solutions
without any haze (Emodi et al. 1976).
Because they are unsaturated compounds,
/i-carotene
ti -apo-8' -carotenal
CHI
canthaxanthin
810 Source Book of Flavors
the carotenoids are susceptible to oxidation
and the dry crystals should be stored in
airtight containers at a low temperature.
The many commercial products are rela-
tively stable, have constant coloring power
and do not fade in the presence of reducing
agents, but they are decolorized by lipid
oxidizing systems, which are accelerated
by high temperature and sunlight (Riber-
Nelson 1990).
P-carotene has a provitamin A value of
1.67 million IU/g and its use in certain foods
augments the vitamin activity as well as
the color. It may be used generally in
foods consistent with good manufacturing
practice.
P-Apo-8' carotenal (Apocarotenal): Is
very similar to P-carotene and although
it occurs in orange, tangerine, etc., it is
prepared commercially by synthesis. It has
an excellent color stability, being a shade
more orange than P-carotene. In the United
States, this carotenoid is permanently listed
as a color additive for use in foods up to
15 mg/lb. of product. It has a provitamin A
value of 1.2 million IU/g and contributes to
the nutritional value of a product.
Apocarotenal is available in the following
forms: as a suspension in vegetable oil
(usually about 30 percent apocarotenal), as
beadlets (10 percent apocarotenal), and as a
2 percent solution in food grade carriers.
The ethyl ester of P-apo-8' -carotenoic
acid is also permitted for use in some coun-
tries. This crystalline compound has a more
yellow-to-orange color than apocarotenal.
Canthaxanthin: Is 4,4' -diketo-P-caro-
tene and has been approved for use in
foods since 1969. It has a more orange color
than P-carotene and although it is less
soluble, it has an unusually high tinctorial
power. This makes it a good colorant for
tomato products. It is also widely used in the
coloring of simulated meats. Canthaxanthin
is permanently listed in the United States
and may be used up to 30 mg/lb. of food
product. It is commercially sold as a water-
dispersible beadlet containing 10 percent
canthaxanthin or as a spray-dried powder
(2.5 to 10 percent canthaxanthin) in a
gelatine/carbohydrate base. These products
give clear aqueous solutions.
Chlorophyll
H,C CH=CH,
==,-:-CHO
1chlorophyll·b
C,uH:,sOOC(CH,),
(phytyl)
chlorophyll-a
Chlorophyll is the green coloring matter
of leaves by which they carry out photo-
synthesis. The chlorophyll in plants is
somewhat analogous to hemoglobin in
blood and their structural formulas are very
similar. Chlorophylls are magnesium
complexes having a porphyrin structure
and contain two hydroxy groups; one is
esterified with phytyl alcohol and the other
with methyl alcohol. In nature, the mole-
cular complex is bound with a protein
moiety.
Commercially, chlorophyll is recovered
from various grasses by alcohol or acetone
extraction of the finely powdered dehy-
drated grass-meal with the subsequent
removal of the solvent under vacuum. The
initial dark, olive-colored, firm extract is a
mixture of pigments including chlorophyll-a
(about 60 percent), chlorophyll-b (about 25
percent) together with xanthophyll (about
10 percent) and carotene (about 5 percent).
This extract is soluble in fixed oils and
organic solvents, and is used as the starting
material for the manufacture of a range of
oil- and water-soluble derivatives.
As long ago as 1909, Wilstater found that
chlorophyll was an ester of chlorophyllin
with phytol and that the compound could be
saponified by alkalis to give a nitrogenous
compound called pheophytin and the free

unsaturated alcohol, phytol. This reaction
is the basis for the production of purified
chlorophyll and chlorophyllins. The color of
chlorophyll depends on the nature of the
coordinated element, which is normally
magnesium. As a result of natural acids
present during the extraction, this element
is replaced by hydrogen. To produce a
bright green color, it is necessary to intro-
duce copper into the molecule. This is done
by treating the separated pheophytins with a
calculated quantity of copper sulfate and
removing all excess ionic copper. The total
and ionic copper content of these products is
determined in aqueous solution by atomic
absorption spectrophotometry.
Whether coppered or uncoppered, the
chlorophylls are soluble in ethanol (95
percent), hydrocarbon solvents, fixed oils
and fats. They are insoluble in diluted
alcohol and water. When oil-soluble chlo-
rophyll is hydrolyzed with alkali, the phytol
and methanol groups are split off and water-
soluble chlorophyllins are formed. The
chlorophyllins, which are either sodium,
potassium or calcium salts, are all water-
soluble. A range of uncoppered and cop-
pered chlorophylls and chlorophyllins is
now available in either semisolid, paste,
granular or powdered form.
The tinctorial power or color value of
chlorophyll products is determined by
evaluation of the blue and yellow color
components of a solution. These are deter-
mined in a Lovibond tintometer. The test
methods and units used are fully described
in the trade literature.
Chlorophyll is almost universally ac-
cepted for use in foods, but the copper
complex is not (neither is accepted in the
United States). In many countries, its use is
limited to certain products (e.g., chewing
gum). Before using the coppered chloro-
phyllins in any food product, reference
should be made to the specific regulations.
In the case of the water-soluble products, it
should be remembered that these salts are
not stable in acid solution as the pheophytin
is precipitated (Blenford 1985). In neutral
Food Colorants 811
and alkaline media, these chlorophyllins are
stable and light-fast.
Cochineal and carmine
+
OH
peonidin
Cochineal is the glycosidal coloring matter
derived from the dried insect Dactylopius
coccus Cos at (Coccus cacti L.) in Mexico,
Central America and the West Indies. The
main commercial source is in the Canary
Islands (Tenerife). Only the wingless female
insects containing eggs and larvae are col-
lected. They are processed to produce either
silver-grain or black-grain cochineal, de-
pending on the temperature used to kill and
dry the insects. It takes about 70,000 insects
to make lib. of color.
The coloring principal of cochineal is
carminic acid, an anthraquinone derivative
present at 8-10 percent. This is a dark
purplish-red compound, which is soluble
in water and ethanol to give a scarlet-red
solution.
Carmine (CI 75470) is the alkaline salt
of the aluminum lake of carminic acid,
prepared directly from cochineal and
containing not less than 50 percent of car-
minic acid. It is a bright red pigment,
which is insoluble in cold water, partially
soluble in hot water and readily soluble
in alkalis. The color of the solution is de-
pendent on the pH. Commercially, carmine
is available as a deep red powder or as a
solution in a mixture of ammonia and pro-
pylene glycol (about 0.3 percent carminic
acid).
Carmine is permanently listed in the
United States, and it is almost univer-
812 Source Book of Flavors

sally accepted for use as a natural food wine or juice manufacture. The product
colorant consistent with good manufac- may be in the form of a fluid concentrate
turing practice. or as a spray-dried powder. The coloring
Cranberry The fruit of the cranberry components are water-soluble and give a
( Oxycoccus macrocarpus L.) possesses a red-violet solution at low pH, changing to
high color value due to the presence of blue as the pH increases. Grape skin extract
anthocyanins, principally peonidin, an is most stable and suitable for use in media
enthocyanin. under pH 3, although the color is not really
Commercially, this natural colorant is stabile to heat, light, oxidation, S02 or
available as a concentrated juice (50° Brix) ascorbic acid (Hill and Weiss 1977).
or as a spray-dried powder carried on malto-
dextrin. Chriboga and Francis (1973) and Orchil
Stahl, Bordonaro and Nini (1988) have Two closely related colorants are obtained
developed a technique for the recovery of from the lichens Rocella tincotria and
anthocyanins from cranberry press cake as Licanora tartarea by extraction with
some 40 percent of the anthocyanins present aqueous ammonia. These are:
in the fresh berries remain in the press cake Orchil a thick reddish-purple liquid
after juice expression. These products whose coloring principles are a mixture of
are water-soluble and produce bright red red orcein (C28H 240 7N2 ), an amorphous
solutions at pH 2.5 or lower. Unfortunately, yellow compound (C 21 H 29N0 5 ) and a com-
cranberry juice is not a strong colorant and pound related to litmus. The wine-red color
requires a relatively high use level; it also is only slightly soluble in water, but readily
has a poor light-fastness. soluble in ethanol. It is pH sensitive, rang-
ing from yellow in acid to blue in alkaline
Grape Skin media. Orchil is permitted for use as a food
Dark-skinned varieties of grape (Vitis colorant in several countries (not including
vinifera, V. ripaira and V. labrusca) have a the United Kingdom or United States)
firm skin, which is rich in anthocyanins, and reference should be made to specific
most of which are mono- and diglycosides regulations.
of those listed in Table 19.9. Some of the Litmus A red colorant, which is used
anthocyanins are also acylated with p- primarily as a pH indicator. The coloring
coumaric and caffeic acids, making a com- principle is azolitmin (C7 H 7N0 4 ) which is
plex and variable mixture of compounds. pH sensitive, giving the well-known color
This results in commercial products that change from red in acid to blue in alkaline
display wide differences in coloring strength media.
and stability, depending on the origin of the
raw material. European grapes contain Paprika and Red Peppers
mostly malvidin-3-glucoside, whereas those Paprika (Capsicum annuum L.) and several
from the eastern United States are rich in other varieties of the genus Capsicum, are
3,5-diglucosides of cyanidin and delphinidin cultivated more for their coloring power
together with their 3-(6-0-p-coumaryl)- than for their flavoring attributes, although
glucoside acylated derivatives (Hrazdina some grades do have a distinctive flavor and
1975). These differences in composition some pungency that may limit their use as
make the European product less stable than colorants. The color is due to the presence
that from American sources. of carotenoids in the skin of the fruit.
Grape skin extract is prepared com- Commercially, the ripe fruits are dried, the
mercially by the aqueous extraction of grape seeds and pericarps separated, cleaned and
skins, which are available in considerable ground. The grade of paprika is determined
tonnage as waste after pressing grapes for by the proportion of these constituents

OH
Capsanthin
Capsorubln
that are used in the final blend. The more
powdered seeds that are present, the lower
the color value and quality of the blend.
The principal carotenoids in capsicum
species are capsanthin and capsorubin,
together with ~-carotene, crytoxanthin and
zeaxanthin and much smaller quantities of
cryptocapsin, lutein expoxide, anthera-
xanthin, violaxanthin and mutatoxanthin.
Curl (1962) carried out an extensive investi-
gation into the chemistry of the carotenoids
of red bell peppers and found that capsan-
thin accounted for about 35 percent, vio-
laxanthin about 10 percent, cryptoxanthin
and capsorubin each about 6 percent, cry-
ptocapsin about 4 percent and other minor
carotenoids a further 2 percent of the total
carotenoids. The amount and type of
carotenoids present depend on the variety
and source of the paprika or red pepper.
Philip and Francis (1971) reported that
paprika contains 10-12 percent of highly
unsaturated triglycerides and that cap-
santhin is present as the dilaurate ester.
Ground paprika or oleoresin paprika, as
Food Colorants 813
OH
OH
well as products containing these colorants,
rapidly lose their red color when exposed
to the sun. De Ia Mar and Francis (1969)
reported that the losses could amount to
some 96 percent of the carotenoids present.
This may be due to the presence of highly
autoxidizable fatty acids. The changes in
color in paprika during ripening, processing
and subsequent storage have been further
examined by Philip and Francis (1971) and
Byrne (1987).
Riboflavin (Vitamin B2 , Lactoflavin)
Riboflavin is a natural vitamin that is
present in almost all plant and animal
tissues, but particularly in milk, eggs and
yeast. Commercially, it is synthesized from
o-xylene, ribose and alloxane. Riboflavin
is only poorly soluble in water and it is
normally used as the 5' phosphate ester
monosodium salt. This is a yellow to orange-
yellow fine crystalline powder, which is
readily soluble in water to give a bright
yellow solution. Although the dry material
is light stable, the solution rapidly loses
 814 Source Book of Flavors

CH2 Turmeric and curcumin

I ;=={..OCHa
HO-CH

HO-CH
I IOCH=CH~OH
I
HO-CH CH2
I
I
CH2
L=cn--Q-on
CH3 ~NY'fo OCHa

CHa~N'YNH Turmeric is a highly colored spice, which is a

close relative of ginger and cultivated in
0 India, China, the East Indies, Caribbean
Islands and South America. It consists of
color, particularly in direct sunlight (Hill the dried rhizomes of Curcuma longa L.,
and Weiss 1977). which contain about 5 percent of a very
aromatic essential oil having a distinctive
Safflower odor, some fixed oil, resinous matter and
Safflower is the dried flower heads of a starch together with a bright yellow color-
Carthamus tinctoria L. and contains two ing principle, curcumin. This component
coloring principles: is 1,7-(bishydroxy-3-methoxyphenyl)-1 ,6-
Safflower yellow: is water-soluble heptadien-3 ,5-dione.
Carthamin (safflower red): a glycoside Turmeric is available in its natural form
that is only very slightly soluble in water (unground) or as a finely ground, bright
yellow powder. The oleoresin is available in
Saffron several forms, including a viscous paste
or oily dispersion, a solubilized product
(Tween 80), or a spray-dried powder. Pure
H22C1s< COOC,2H21 Ou)2
a-crocin curcumin is also available as a fine orange-
yellow pure crystalline powder. This ma-
CHa CHa terial is insoluble in cold water and sparingly
I
HOOC-C soluble in hot water. It is soluble in ethanol
and ether and solutions exhibit a strong
CHa green fluorescence. Curcumin is also soluble
in glacial acetic acid. The color is pH-
crocetin
sensitive, being bright yellow in acidic and
reddish-brown in alkaline solution.
Saffron consists of the dried styles and Powdered turmeric is an important con-
stigmas of Crocus sativus L., which have stituent in curry powders and gives them
not only a bright yellow color but a very their characteristic yellow color. Unfor-
distinctive flavor. Saffron is available tunately, products colored with either
commercially as a reddish brown mass of turmeric or curcumin do not have good
threads or as a red-brown to golden-yellow light-stability, particularly if exposed to
powder. The coloring matter is water- direct sunlight. In such products, severe
soluble and shows good stability (Francis fading occurs after only a few days (Hill and
1987). Weiss 1977; Side 1987).

Nonabsorbable Food Colors
Food colorants, both synthetic and natural,
if they are digestible, are absorbed into the
body on ingestion, and it is their metabolic
fate that gives rise to toxic risks. If the
colorant were not systemically absorbed and
passed through the body only within the
gastrointestinal tract, these toxic risks would
be very considerably reduced, if not com-
pletely eliminated. After several years of
research, this basic concept was applied to
food colors (Dynapol1978).
The products developed consisted of
selected colorants bonded to a stable
polymer, which had the effect of increasing
the molecular weight above 1,500, thus
precluding intestinal absorption. At the
same time, the polymer was not to be de-
gradable in any part of the gastrointestinal
tract. The products, to be effective food
colorants, had to be water-soluble, capable
of forming lakes, be tasteless, and display
normal chromophoric characteristics in-
dividually and in blends. The concept and
basic technology of these products was the
subject of an article by Furia (1977). While
the concept was extremely attractive, the
developers could not obtain FDA approval
for their products and thus the concept died.
Inorganic Color Pigments
Carbon Black
Carbon black is a finely divided form of
carbon made by the incomplete combustion
of hydrocarbons. That most widely accepted
for use in foods is of vegetable origin.
Depending on the source material and the
method of manufacture, they are normally
fine, bulky, black powders insoluble in
water and may contain a considerable
quantity of ash. Channel black is a special
grade made by the impingement of a
luminous flame of natural gas against an
iron plate from which the carbon is removed
at regular intervals. Channel black is
characterized by having a very small particle
size, but may also be somewhat aromatic.
Food Colorants 815
Its use is permitted in certain countries but
not universally.
Liquid dispersions of carbon black are
commercially available and these are much
easier and cleaner to use than the powdered
form. They are normally oil-based and may
contain added emulsifiers to stabilize
the product. Carbon black is an effective
coloring for use in the manufacture of
licorice paste.
Iron Oxides
Iron oxides occur naturally, but are mostly
manufactured by either treatment of a
solution of ferrous sulfate or chloride with
an alkali followed by oxidation of the
precipitated hydroxide in a current of air at
30°C for 12-16 hours, or by wet oxidation of
ferrous sulfate liquor in the presence of iron
and soda ash followed by calcination.
The FAO/WHO (1963) defines six
grades, namely: (a) CI Pigment Yellow 42
and 43-Ferrite yellow, Goethite or Mars
yellow; (b) CI Pigment Brown 6 and 7-
brown iron oxides and brown magnetic
oxide; (c) CI Pigment Black 11-iron oxide
black, magnetic iron oxide; (d) Red iron
oxide-Rubigo, Indian red or iron ses-
quioxide; (3) Iron oxide, Brown native-
Red hematite and (f) iron oxide, brown
precipitated.
Of the above, CI Pigment 11 (CI 77499)
is the most widely used for coloring choco-
late, cake mixes, meat paste, etc.
Titanium Dioxide
Titanium dioxide (CI 77891; E 171) is an
inorganic coloring pigment (Ti02), which is
a dense white, tasteless, odorless, unfusible
powder. It is insoluble in either cold or hot
water or dilute acids. The purified food
grade is used in the panning of sugar con-
fectionery. Although it disperses readily in
liquids, it tends to settle out unless the liquid
is viscous (e.g., sugar syrup).
Ultramarine
Ultramarine was formerly produced by
powdering the natural mineral lapis lazuli,
816 Source Book of Flavors

but it is now manufactured by fusing to- CRC Crit. Rev. Food Sci. Nutr. 28(4):273-
gether kaolin, sodium carbonate or sulfate, 314.
sulfur and carbon for about 10 hours in the Francis, F. 1987. Lesser-known food colorants.
absence of air. Chemically, ultramarine is Food Techno!. 41(4):62-68.
the polysulfide of sodium (or potassium, Furia, T.E. 1977. Nonabsorbable polymeric food
colors. Food Techno!. 31(5):34-39.
lithium or silver) alumino-silicate. Its con- Greenshields, N. 1973. Caramel. Part 2. Manu-
stitution is complex and unknown. The facture, composition and properties. Process
initial reaction produces ultramarine green, Biochem. 8(4):17-20.
which may then be treated in various ways Hallagan, J.B. 1991. The use of certified food
to produce ultramarine blue or violet. color additives in the United States. Cereal
Ultramarine blue (CI 77007) is an effec- Foods World. 36(11):945-948.
tive whitener for sugar and is also used in Heath, H.B. 1981. Source Book of Flavors.
the manufacture of salt intended for animal Westport, Conn.: A VI Publishing.
feeds. Hill, J.A. and Weiss, A.L. 1977. Naturally
Occurring Colorants. I. Drug Cosmet. Ind.
122(11):36:114. II. Ibid, 122(6):55:140.
References
Lauro, G.J. 1991. A primer on natural colors.
Blenford, D. 1985. Natural food colours. Food,
Cereal Foods World. 36(11):949-953.
Flavor., Ingred., Package. Process. 7(7):
North, R. W. 1973. Caramel-the versatile
19-21.
colouring. Flavour Ind. 4:337-338.
British Caramel Manufacturers Association.
Padival, R.A. and Sastry, L.V.L. 1985. Stability
1988. Caramel Colors. Soft Drink. Manage.
of safflower, kokum and beetroot colours in
Inter. Oct., 16-17.
model systems and some fruit products.
Byrne, M. 1987. Colours: the natural choice.
J. Food Sci. Tech., India. 22(5):346-350.
Food Manufact. Inter. 4(4):40-41.
Phillip, T. and Francis, F.J. 1971. Oxidation of
Chiriboga, C.D. and Francis, F.J. 1973. Ion-
capsanthin. J. Food Sci. 36:96-97.
exchange purified anthocyanin pigments as a
Riber-Nielson, M. 1990. Natural beta carotene as
colorant for cranberry juice cocktail. J. Food
a food color. Eur. Food and Drink Rev.
Sci. 38:464.
Autumn:113-115.
CFR 1990. Code of Federal Regulations.
Rush, S. 1986. Colour by numbers. Food,
Washington, D.C.: U.S. Government
Flavor., Ingred., Package. Process. 8(7):23-
Printing Office.
27.
Curl, A.L. 1962. The carotenoids of red bell
Side, C. 1987. Natural colours. Food Trade Rev.
peppers. J. Agric. Food Chern. 10:504-509.
57(10):541-544.
De La Mar, R.R. and Francis, F.J. 1969.
Spears, K. 1988. Developments in Food Colour-
Carotenoid degradation in bleached paprika.
ings: the natural additives. Trends in Bio-
J. Food Sci. 34(3):287-290.
technol. Nov. 283-288.
Dynapol. 1978. Developing nonabsorbable food
Stahl, H.D., Bordonaro, M.E., and Nini, D.
colorants and antioxidants. Food Can.
1988. Cranberry color extraction. U.S. Patent
38(7):58.
Dziezak, J.D. 1987. Applications of food
us 4 775 477.
Ward, R.P. 1973. Caramel in the U.K. and
colorants. Food Techno!. 41(4):78-88.
E.E.C. Flavour Ind. 4:339.
Emodi, A.S., Scialpi, L., and Antoshkiw, T.
Ward, R.P. 1976. Caramel-its qualities and
1976. Carotenoids colors. Food Techno!.
uses in food processing. Food Process. Ind.
30(7):58-60
45(540):33-34.
Frick, D. and Meggos, H. 1988. FD&C Colors-
Woodroof, J.G. and Phillips, M.S. 1974. Bever-
Characteristics and Uses. Cereal Foods
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World. 33(7):572-574.
Westport, Conn.: A VI Publishing.
Francis, F.J. 1989. Food colorants: anthocyanins.
Chapter 20
Sensory Analysis
Marianne H. Gillette
TEST OBJECTIVES
The most critical consideration in designing
and implementing a sensory test is a clear
understanding of the study's objectives.
While this logical requirement is quite
obvious, it is frequently not adequately
communicated or considered in designing a
sensory test. The result of such work leads
to invalid and/or misleading conclusions and
recommendations, and wasted testing
efforts. Stating the objectives of a study
does not require much time. It requires
a simple focus on the overall program,
answering such questions as:
• What minimal sensory information is
required in order to proceed with the
study? What form must this information
be in?
• What actions will be taken based upon
this information?
• What other tests (physical, chemical,
sensory) have been or will also be
conducted?
• What risks are involved? What is the cost
of inaccurate or insufficient information?
What levels of risk (probability of Type I,
Type II error) can the project absorb?
• If a "control" sample is involved, there
must be a clear definition of it.
Many studies have objectives that are
very clear-cut, such as a reformulation
project where the test sample must simply
match the current product at a given level of
statistical confidence. Studies that require
significant resource investment have objec-
tives that require some cross-examination
and client-supplier discussions. For
example, a simple QC question, "Does this
production sample match the control?",
leads the astute sensory scientist into a
cross-examination such as:
• What is the "control"? Its history?
• How "close" is close enough?
• What are the acceptable limits for pro-
duction variance?
• What other physical and chemical tests
are performed on this product?
• What actions, and their timings, will be
taken based upon the sensory results?
After the test objective is defined and
agreed upon, a test design is formulated.
The test methodologies selected are those
that are best suited to provide the required
information at the least cost and risk. The
sensory test is designed to fit the project
objective. Many sensory programs tend to
routinely use their favorite, or "best,"
method to address all objectives. The
817
818 Source Book of Flavors
triangle test and the employee acceptance
tests are the most frequently abused in this
way. Sometimes, standard practices don't
meet test objectives efficiently, and a situ-
ation exists where the sensory scientist
needs to adapt a current practice, or
develop a new approach, in order to meet
the project objectives.
Applications of Sensory Testing
An experienced sensory professional can
create methodologies and unique, custom-
ized approaches to sensory testing. For the
beginner, sticking to the basic methods is
recommended to ensure validity of results.
Some of the common applications of sen-
sory testing in the food and beverage indus-
try are presented below. Specific methods
are described in Section II.
New Product Development-Unfor-
tunately, many new products are imitations
or variations of some established standard.
Sensory testing would assure that the stan-
dard target has been closely matched or that
the unique "point of differentiation" has
been made. Descriptive analysis would be
the preferred method. Hedonic testing
would determine if the acceptability re-
quirements have also been met. Note that
tacos and oranges taste distinctly different,
but may have equivalent acceptance scores!
Product Matching- The objective of
product matching is to verify that there is no
perceptible difference between the test and
standard product. Most cost reduction and
ingredient substitution projects fall into this
classification. Analytical difference tests,
such as the triangle and duo-trio tests, are
used.
Product Improvement- Real improve-
ment of a product should be measured
by hedonic tests, to establish whether
the experimental product is liked more
than the control and truly represents an
"improvement."
Process Change-A process change
should maintain or improve the product.
The testing sequence is logical:
1. Analytical (difference and/or descrip-
tive) tests to determine whether the
experimental product is different from
the control (if it is not different, it cannot
be better).
2. Affective (hedonic) tests, if products
differ, to establish whether the experi-
mental product is liked as well as or
more than control.
Cost Reduction and/or Selection of a
New Source of Supply-A successful cost-
reduction program based upon lower-priced
ingredients, a lower-cost process, or pro-
duction in a different location usually must
yield an end product comparable to the
product formerly produced. Changing to a
new supplier of raw materials should also
result in an end product comparable to
the standard or control. This is a job for
analytical tests.
Quality Control-Analytical tests are
used during production, distribution and
marketing to ensure that the end product is
as good as the standard. Representative
samples are usually evaluated as follows:
1. Difference tests to determine whether
the sample is different from the standard
(if it is not different, it must be as good
as the standard).
2. Descriptive tests, if the sample is found
to be different, to indicate how the
sample differs from the standard. Re-
sults of these tests may be used to guide
remedial action, such as change in
processing procedures. Small-scale de-
scriptive panels work well.
Storage Stability-Analytical tests
evaluate product stability during trans-
portation, warehousing and retailing, and
during storage in the home. To establish
information on product shelf life, repre-
sentative samples are obtained, evaluated
initially, and subjected to controlled storage
conditions for subsequent tests. At specific
time intervals, storage samples are with-
drawn and evaluated, generally in com-

parison with a control. The control must
be of the same production lot or batch as
the test samples, and must be held under
conditions known to maintain the original
quality, such as freezing or refrigeration.
Analytical tests to determine product
storage stability may include the following:
1. Difference tests to determine whether
the storage samples are different from
the control (if no significant difference
is found, product stability is assumed).
2. Descriptive tests, used alone or in
conjunction with difference tests, to
characterize and/or quantify the changes
that may have occurred during storage.
Descriptive analysis is frequently used
in situations where maintenance of a
control is unrealistic.
3. Affective tests may be used to deter-
mine the relative acceptance of stored
products.
METHODS
In designing a sensory study, it is critical
that all standard methods, their strengths
and weaknesses, be understood. Sensory
methods can be classified as either Ana-
lytical or Affective, using the following
definitions:
ANALYTICAL TESTS: Requires the use
of objective sensory methodologies, which
define the characteristics/properties of
foods. Analytical testing answers questions
such as: Which sample is saltier? Which
sample is different? How roasted vs. toasted
vs. burnt is the sample? Analytical methods
define the sensory properties of a food
system, but will not directly predict how
much it will be liked. Analytical tests
include:
1. Difference Testing: Triangle, Duo-trio,
Paired and Multiple Comparison tests,
Signal Detection (r-index).
2. Descriptive Analysis (Flavor Profile,
Quantitative Descriptive Analysis,
Spectrum).
Sensory Analysis 819
3. Ranking (not on preference).
4. Quality Evaluations: with clearly defined
characteristics of "quality."
AFFECTIVE TESTS: Requires the use of
non-expert, non-trained, "naive" subjects
for acceptance/preference/hedonic/personal
opinion testing. True consumers of the
product are the ideal subjects, but are
costly. Affective testing can be performed
in-house by employee panelists who are not
food or flavor scientists or trained panelists.
Affective testing answers such questions as:
Which sample do you prefer? How much do
you like it? What don't you like?
Analytical Tests
Difference Testing simply answers the ques-
tion, are the samples different? Exactly
how or how much the samples differ is not
defined. These tests include the popular
triangle test, the duo-trio test, the paired
comparison test, multiple comparison test
and r-index (signal detection). Such tests
can be conducted with expert or non-expert
judges. It is generally assumed that if a
panel of experts fails to find a significant
sensory difference between products, the
consumer (who is generally less sensitive)
would not be able to discriminate. This may
not necessarily be true for extended home
use of a product. Difference tests should be
conducted with a minimum of 30 subjects,
preferably closer to 50 or 60. Increasing the
number of judges reduces~ risk-the risk of
concluding that two samples are similar,
when in fact they are different. Most often
the food researcher is interested in pre-
serving the sensory characteristics of a food
product, while effecting changes in ingre-
dients, processing, cost, etc. Thus, the
actual objective, in practice, of most "dif-
ference" testing is actually to prove simi-
larity. Unfortunately, difference tests
are designed to prove differences, not
similarities. The a probability values that
are published in the standard tables rep-
resent the risks associated with concluding
820 Source Book of Flavors
that two samples are different when they are
really the same. This risk is generally of
minimal interest in the food business. In
order to protect the business franchise, it is
wise to protect B risk and to use a higher
number of subjects (50-60), or at least a
very sensitive panel who are screened
for above-average ability to discriminate
differences. B probability values can be
calculated by using the formula provided
and discussed in Amerine, Pangborn and
Roessler (1965). Excellent discussions on
the beta-risk issue (Type II error) can also
be found in Stone and Sidel (1985) and in
Meilgaard et al. (1987). The latter reference
also includes methods for similarity tests
versus difference tests.
Triangle Test
This is probably one of the most popular
and frequently used laboratory tests. The
basic technique is to provide the judge with
two samples that are identical (from the
same batch) and a third sample that varies in
some respect. The object of the test is to
correctly identify the different sample. In
addition, the respondent is often asked to
give the reason for his decision. Published
tables (Roessler et al. 1978) are available
in all textbooks on sensory evaluation to
determine the number of correct identi-
fications required to give an indication of a
statistically significant difference.
By chance alone, if no difference exists
between the three samples, there is a one in
three possibility that the odd sample will be
identified. Therefore, if thirty judgments
are collected, at least ten would be expected
to be correct by chance alone. In order for
the samples to be found different at the 95
percent level of confidence, the sample
would have to be correctly identified at least
fifteen times. There is nothing remarkable
about a 95 percent level of confidence (a =
0.05), although it continues to be used as a
decision point by many experimenters. It is
recommended to calculate, or use Roessler
et al. 's (1978) tables, the exact probability of
the result and then make business decisions
accordingly. For example, if out of 36
subjects, 17 correctly identified the odd
sample, the resulting probability that this
effect was due to chance is a = 0.058 (the
samples are different at the 94.2 percent
"level of confidence"). If the 95 percent
confidence level is used as an arbitrary
cutoff, the samples would be considered a
match and the product would be shipped to
the customer. If this were an important
customer, would it be wise to ship the test
product? At what level of confidence should
the decision be made not to ship the pro-
duct? Every business decision varies, re-
quiring clear planning of both the test
objectives and the actions to be taken based
upon the test results.
The order in which the samples are
presented to the judge has been shown to
affect the test results. When no stimulus
variation exists, there is a tendency to select
the middle sample as being odd. To prevent
this bias, it is advisable to present all six
possible combinations in a random or
balanced order. For instance, in a test to
determine whether or not an imitation
cherry extract differentiated from a real
cherry extract, the following sample com-
binations would be suggested:
1st Sample 2nd Sample 3rdSample
Panelist 1. Real Real Imitation
Panelist 2. Imitation Real Real
Panelist 3. Real Imitation Real
Panelist4. Imitation Real Imitation
Panelist 5. Imitation Imitation Real
Panelist 6. Real Imitation Imitation
Each combination should then be
numbered and assigned randomly among
the total number of panelists/trials. A
minimum of 36 subjects is recommended. If
panelists are limited, eighteen subjects
may be used twice. The more experienced
the subjects are, the greater the likelihood
that differences will be found.
Test conditions for triangle tests must be
carefully controlled. All sample variation,
except the attribute to be measured, must

be eliminated or masked to prevent bias.
When making their decision, sensory judges
quickly learn to take advantage of every
possible clue. Therefore, all variables such
as temperature, consistency and mouthfeel
must be carefully controlled.
The advantages of the triangle test are
many: 1) it is rapid to administer, 2) it is an
easily understood task by judges, 3) data
analysis is almost immediate and, 4) the test
is well understood and universally used. The
disadvantages of this test are: 1) only two
samples (test and control) can be tested,
2) three samples of highly flavored product
may be overwhelming, and 3) no direction
on how the samples differ is provided.
Directional Triangle Test
This is a modification of the triangle test,
which sometimes makes it more efficient.
For example, if a new encapsulated choco-
late flavor becomes available at a reduced
price, a directional triangle test might be run
to check if the new flavor is different and,
if so, whether it is stronger or weaker.
Randomly arranged triangle tests are
presented and the judge is asked to identify
the odd sample, as well as which sample
(pair or odd) is stronger in some predefined
characteristic (i.e., chocolate flavor).
Data from the directional triangle test are
analyzed by using directional data from the
judges who correctly identified the odd
sample. The basic directional triangle test
chance probability is % (that is; 1/3 x Vz).
Duo-Trio Test
The duo-trio test is another three-sample
difference test. In this design, the judge
is first served a coded "control" or "refer-
ence" sample, which he/she evaluates.
After the first sample is examined, it may or
may not be removed, and two unknown
coded samples are submitted successively in
random or balanced order. The judge
is asked to indicate which of the two un-
knowns is the same as the first sample.
Although the duo-trio test is a three-sample
test, the results are analyzed by using one-
Sensory Analysis 821
tailed paired comparison tables, as the
probability of guessing the correct answer is
50 percent.
If the control is removed, this test more
closely mimics the actual "consumer" de-
cision, in that the consumer rarely has a
"control" or "reference" sample available
for comparison to a new product. The con-
sumer generally operates from a memory
standard, which is what the duo-trio test
also requires when the control is removed.
This test can be used as a form of panelist
screening and training. When training
tasters, it is essential that they be informed
of their success or failure to identify the
correct match. Even when they are in-
correct, this practice helps teach judges to
discriminate, especially if allowed to retaste
the samples and attempt to associate the
identical combination.
Paired Comparison
Comparison of two samples is commonly
referred to as the paired-comparison test. In
a simple paired comparison test the judge is
presented with two samples and asked
whether there is a difference between them.
In a directional test, two samples are
presented for comparison and the judge
must determine which of the two samples is
stronger in some well-understood and pre-
defined characteristic (i.e., personal pref-
erence, saltiness, chewiness). In either
test, the samples can be presented simul-
taneously or successively.
Simple Paired-Comparison: The presen-
tation of two samples (AA, AB, BA or
BB) is referred to as the simple paired
comparison method. The response in this
case can be either "there is a difference"
or "there is no difference." Proper
administration of this test is critical.
Judges must be informed of the prob-
ability of receiving identical or different
stimuli. They must not assume that the
samples are different (that only the AB
and BA combinations are given); they
must be instructed that all four orders
822 Source Book of Flavors
of presentation are given (AA, BB,
AB, and BA). Results are analyzed
by counting the number of correct
answers and using the two-tailed paired-
comparison tables.
Directional Paired-Comparison: This is
the most widely used paired test. There
are two orders of sample presentation,
AB and BA. The panelist is asked to
determine which sample is stronger in
some predefined and well-understood
characteristic. It is not wise to ask a
non-trained panel questions such as
"which sample has more eugenol
flavor?" or "which sample has more
terpene character?" because either the
panelist will have no idea of what the
terms "eugenol" or "terpene" mean, or
he will have the wrong idea. Thus, the
test will measure perceived differences in
undefined terms.
Positional bias is an important factor in
the paired comparison test, thus the sample
order of presentation must be balanced so
there are equal numbers of AB and BA
presentations.
Results are analyzed by use of the paired-
comparison tables (Roessler et al. 1978).
One table is for one-tailed tests, while
another is for two-tailed tests. The statistical
interpretation for the differentiation be-
tween these tests is complex. If, when
designing the test, the "correct" answer
could be either sample A or sample B (both
results being possible), the test is two-sided.
However, if it is already known that one
sample is more concentrated than the other
and the judges' ability is being tested, then
only one sample can correctly be identified
as being more intense. This latter test is a
one-tailed test and the table identified as
"one-tailed" is used to determine whether
or not a significant difference exists. It
should be noted that one-tailed tests have
lower limits. The duo-trio test is a one-tailed
paired comparison test, as there exists only
one "correct" answer.
Multiple Comparison Test
A known standard is labeled as such
("reference" or "control") and presented
to the panelist with several blind coded test
samples. The panelist is asked to compare
each coded sample to the known standard
on the basis of some identified character-
istic. This test can be used very efficiently to
evaluate four or five samples at a time, but
only on one or perhaps two characteristics.
Small differences between the test and
standard can be detected; direction and
magnitude of differences can also be mea-
sured. Results are analyzed by ANOVA
(Larmond 1977, and Meilgaard, Civille and
Carr 1987).
Signal Detection (r-index)
Adaptation of signal detection theory for
sensory difference testing has been well-
described by O'Mahoney (1983, 1986,
1988). The practical "short-cut" method
involves calculation of the "r-index," which
is a measure of sensory sensitivity to dif-
ferences between samples. It is a measure of
the likelihood that a judge can distinguish
an incoming sensory signal (such as a test
sample) from background noise (such as
a control sample). It is also said to be a
measure of the degree of difference between
two products (O'Mahoney 1983). R-indices
range from 50 to 100; 100 being a 100
percent noticeable difference between a
control and test sample, and 50 being a non-
distinguishable difference between the test
and the control.
The higher the r-index, the greater the
degree of difference between the two
samples. One advantage of the r-index test
is that it can be used to test a control sample
in comparison to several other test samples
within one fairly rapid test. The experi-
menter is not limited to a simple two-sample
design. A disadvantage is that the r-index
scale is not universally understood as well as
a probability values are. The significance of
r-indices of 0.8 versus 0. 7 is unclear. How a
business decision is made on the basis of a
given r-index is also unclear. Calculation of
 Sensory Analysis 823

PRODUCT: COLA N.&.IIE._ _ _ _ _ _ _ _ __

DATE._ _ _ _ _ _ _ _ __

1. Taste and ramiliarize rour1e1r vitb tbe control CCI.

2. Return the control and wait ror the 1ample1.
3. Evaluate the 1aaple1 rrom lert to ri&ht and au1ver the rollovin& QUeltiona.
(Cbeck onlJ ~ boJ per l&mplel

Sample LZ

_I u lUre !!...!! the control

_ I am not aure, but I think it h the control
_I u not aure, but I think it ia not the control
_ I am aure it ia not the control

Sample NP

_ I am 1ure !!...!! the control

_I 11111 not aure, but I think l t h the control

_ I am not aura, but I think it la not the control

_I 11111 1ure it iii not the control

SU!Iple Q!

_ I am 1ure l t h tbe control

_ I am not 1ure, but I think!!...!! the control

_I 1.111 not lure, but I think it h not the control

_ I am 1ure it h not tbe control

FIGURE 20-1. Sample ballot.

the r-index from raw panel data is easily
done by hand or by programming a calcu-
lator. There are no tables to refer to inter-
pret the statistical significance of the r-index
result.
To run an r-index test, the panelist is
presented with a control (usually referred to
in signal detection as the "noise" or "n")
that may remain or be removed, and then
either one or more coded "signals" (these
are the test samples) and a coded duplicate
of the control. The judge is asked whether
he is sure the coded sample is the same as
the control, whether he thinks but is not sure
that the coded sample is the same as the
control, whether he thinks but is not sure
that the coded sample is not the same as the
control and if he is sure that the samples are
different. An example of a ballot is shown in
Figure 20-1.
The formula for calculating R-Index is
shown in Table 20-1.
When 10 subjects were presented with a
control ("noise") and then with blind coded
samples of both the control (N) and a test
sample (S), the following results were found
(Table 20-2).
Because the r-index is so close to 1.0
824 Source Book of Flavors

TABLE 20-1.

S-sure not-S-sure not-N-sure N-sure

Sample Signal= S a b c d ns = a+b+c+d

presented Noise= N e f g h nN = e+f+g+h

a(f+g+h) + b(g+h) + ch + 112 (ae + bf + cg + dh)

r=
(ns) (NN)

TABLE 20-2.

s S? N? N

Sample s 6 2 2 ns = 10

Presented N 2 7

60 + 18 + 14 + 112 (2 + 4)
r = = 0.95
10 X 10

it can be concluded that the samples are "Spectrum" method of Sensory Spectrum
different. But how different? Perhaps more (Meilgaard, Civille and Carr 1987). Many
different than another test sample with an sensory departments devise their own
r-index of 0. 70. This method still leaves customized methods of descriptive analysis,
the experimenter with the need to calibrate with most methods yielding basically the
the r-index scale using products with known same type of information.
differences, so the r-index as a measure If collected using interval (or ratio)
develops practical meaning. scales, data from descriptive analysis panels
can be analyzed statistically by use of
Descriptive Analysis common statistical methods such as the
The "Descriptive Analysis" technique of t-test and analysis of variance. Data are
sensory evaluation identifies, describes and often presented graphically in a variety of
quantifies sensory (visual, textural, audi- forms ranging from histograms to circular
tory, olfactory and gustatory) qualities of a graphs. The circular graph technique pro-
given product. This technique requires a vides an immediate picture of how a product
panel of five to ten trained persons who are tastes and, therefore, is very useful in
thoroughly familiar with the product's communicating the results of a descriptive
sensory characteristics, and who can accu- panel. To interpret the graph, realize that
rately and precisely communicate their the center point represents zero on all the
perceptions. There are a variety of com- descriptive scales, and points radiating
monly used forms of descriptive analysis, outward from the center are increasing in
including the "Flavor Profile" method magnitude. Figure 20-2 illustrates the
of Arthur D. Little Inc. (Caul 1957), differences between two Bourbon Vanilla
the "Quantitative Descriptive Analysis" extracts (Madagascar and Comoros) in
method of Tragon Corporation (Stone et al. comparison to an Indonesian extract. The
1974, and Zook and Pearce 1988) and the flavor graph clearly illustrates that the
 Sensory Analysis 825

TOTAL RESIN AROMA

I
I
PRUNEY AROMA•,
''
_.WOODY AROMA
----
TOTAL AROMA-

/
/
VANILLIN FLAVOR**

• STATlSTlCAU.Y SIGNIFlCANT DIFFERENCE AT THE 95> LEVEL

"STATlSTlCAU.Y SIGINIFlCANT DIFFERENCE AT THE 99• LEVEL

-COMOROS - - - INDONESIAN "'"'" MADAGASCAR

FIGURE 20-2. A circular graph illustrating sensory differences in vanilla from

different regions.

TABLE 20-3. Black Pepper

Descriptive Analysis Term Physical Reference Verbal Definition

Woody B-caryophylene @ 100 ppm Sawdust

Musty Borneol @ 50 ppm Wet basement
Terpene oc-phellandrene@ 500ppm Citrus
Heat Piperine @ 30 ppm Burning/spicy
Floral Balsam Oil @ 500 ppm Flowery-sweet
Soapy Saddle soap@ 1.0% Soap-like

Indonesian extract does not smell or taste
the same as the Comoros and Madagascar
(Bourbon) extracts; the Indonesian extract
is significantly stronger in smoky character,
weaker in pruney character, vanillin and
overall vanilla quality.
It is important to note that not all differ-
ences on the flavor profile are statistically
significant (i.e., aroma and flavor), and that
the relative importance of each attribute
may be different. For example, a statis-
tically significant difference between
samples in the pruney character would be
considered less severe a problem than a
statistically significant difference in vanillin
character.
Descriptive Analysis is most often used as
a technical tool to aid in development or
improvement of a product, as well as to
delineate problem areas in shelf life. It is
very useful in helping to understand the
sensory qualities of a product, but it is
not the appropriate test to be used when
preference or acceptability judgements are
required. The descriptive analysis technique
can be used most satisfactorily, however, in
conjunction with hedonic tests to explain
affective results.
Today, descriptive analyses generally
employ some form of an anchored line
scale. The line scales may be anchored at
the ends (i.e., none and extreme), at a
826 Source Book of Flavors
midpoint, or at several points along the
scale. Panelists may be calibrated to these
anchor points using known references for
strength. All vocabulary terms used in
descriptive analysis should be illustrated by
some verbal and physical references,
as demonstrated in Table 20-3 and in
Mielgaard, Civille and Carr (1987).
When physical references are used rather
than verbal definitions alone, it is possible to
transfer the panel technology to a new
panel. Verbal definitions do not transfer as
well. Interpretation of descriptive panel
results may be done solely on a statistical
basis, when the ballot lists all possible
characteristics, and the number of subjects
and repetitions per sample is large enough,
generally 10-18 subjects and 2-3 reps.
Other approaches rely not only on the
statistical results, but also upon a panel
discussion that follows each test. The benefit
(and sometimes risk) of the discussion is the
learning process that can occur between
subjects, particularly when unusual or
unexpected flavor notes appear.
Descriptive panelists may be recruited
from internal or external sources. Training
usually requires 6-10 hours per product.
When part-time or temporary employees
are used solely as dedicated descriptive
panelists, the concerns about security are
often overweighed by the flexibility and
focus the panel administrator has in utilizing
these "full-time" panelists. When full-time
regular employees are used for subjects,
there are certain other benefits, such as
time and cost efficiencies, generally im-
proved communications on flavor issues
TABLE 20-4.
Judge Sample A
1 2
2 2
3 2
4 1
5 1
Rank Sum 7 9
and the overall benefits of participative
management.
Rank-order
The ranking method is a very simple, quick
and easily understood method. It is used to
determine how several samples differ on the
basis of a single characteristic (i.e., sweet-
ness, meatiness). The coded samples (which
may contain a control or standard) are
presented simultaneously to the panelist,
who is asked to rank them in order of the
intensity of a single specified characteristic.
It is critical that all panelists thoroughly
understand the meaning of this specified
characteristic; that there is no ambiguity.
When necessary, one characteristic (i.e.,
sweetness) can be ranked, after which
another characteristic (i.e., sourness) may
be ranked in another coded set of the same
samples. In order to prevent order bias, all
samples must be randomly presented.
Analysis of Ranking test results are
simplified by utilizing prepared tables
(Newell and MacFarlane 1987), providing
the number of samples is less than 13 and
the number of judges does not exceed 100.
For example, when four samples of wine
were ranked for sweetness by five judges,
the following data were obtained (Table
20-4).
Consulting the rank sum difference table
for comparison of "all treatments" (a =
0.05) we find the value "11," which is the
minimum difference between any two rank
sums needed to conclude that there is a
difference (a = 0.05).
Thus, for the wine test, if the difference
SampleB SampleC SampleD
3 4
4 3
1 3 4
3 2 4
2 4 3
16 18

between any of the rank sums is above 11,
a difference exists between those two
samples. Since our rank sums for Samples A
and D are 7 and 18, we do have a difference
in sweetness at the 95 percent level of con-
fidence. None of the other pairs of samples
is different. Newell and MacFarlane (1987)
have also published tables for comparison of
"treatments versus control" by rank sums.
Ranking data can also be analyzed by
transformation, according to the method of
Fisher and Yates (Larmond 1977) or by
Friedman's rank sums test (Meilgaard et al.
1987).
Quality Evaluations
Several industries have traditional "expert"
quality grading methods, which have been
utilized so long and so universally that
they have basically become standardized
methods. Such tests have been in long use
for agricultural products, such as edible
oils, dairy products, and meats. Most of
these "methods" do not specify definitions
or training procedures for the "quality
experts" to be calibrated. These methods
are discussed in Stone and Sidel (1985) and
will not be addressed here.
True "Quality" eventually must be
defined by the customer to accurately
measure unacceptable deviation from the
quality standard. Fortunately, in the flavor
industry the "Gold Standard" for Quality is
generally an industrial customer's sample or
a natural target. Once a Quality Standard
is identified and secured, a panel can be
trained on the concept of what "Quality" is
for that particular product, the normal and
TABLE 20-5.
Quality Scale Hedonic Scale
(trained panelist, (untrained panelist, personal
"expert" opinion) poinion)
_Excellent _Like a lot
_Good _Like slightly
_Fair _Neither like nor dislike
_Poor _Dislike slightly
_Very poor _Dislike a lot
Sensory Analysis 827
acceptable deviations from the reference,
and some of the characteristics that define
the standard. Essentially, this is a modified
form of descriptive analysis. For example, a
quality evaluation method for vanilla ex-
tract may require the expert panel to be
calibrated on the general characteristics of
vanilla flavor (vanillin, woody, pruney,
floral, etc.) and to become intimately
familiar with the range of acceptable
qualities for the Gold Standard. The
standard could be a Java vanilla (woody and
smoky) or a Bourbon vanilla (resinous and
higher in vanillin), depending upon the
customer's definition and need.
Another type of "quality" evaluation is
often confused with hedonic scaling (Table
20-5).
The hedonic scale is for use by untrained
panelists only. When untrained subjects are
given a quality scale, they essentially will
interpret it as a personal opinion scale,
although some may recognize the difference
between quality grading and personal
opinion.
When experts use the Quality scale
(Poor-Excellent), they must be calibrated or
trained in the universe of the product so
as to render a professional, not personal,
opinion. For example, a flavorist who might
personally have a strong dislike for cilantro
flavor (waxy, soapy) should be able to
recognize and score an excellent-quality
cilantro flavor (also waxy, soapy). The
customer's opinion on cilantro flavor should
be reflected in the professional "quality
score," not the personal opinion of the
judge.
Quality evaluations such as these can be
used as rapid laboratory tests to predict
customer response or to rapidly score a
large volume of products for an optimiza-
tion or similar experimental design.
Affective Tests
Employee Acceptance Tests
The use of company or college employees to
predict the hedonic response or real con-
828 Source Book of Flavors

sumers is very widely practiced (and risky, The most popular scales used are the
if not interpreted correctly). Company 9-point and 5-point hedonic scales:
employees tend to be familiar, loyal to (and
critical of changes in) company products,
Overall Acceptability Overall Acceptability
and do not reflect the dynamics of the _Like extremely _Like a lot
market (price, promotion, positioning). _Like very much _Like slightly
However, the use of employees to screen -Like moderately _Neither like nor dislike
products for relative sensory acceptability -Like slightly _Dislike slightly
prior to engaging in expensive consumer _Neither like nor dislike _Dislike a lot
_Dislike slightly
testing is wise. If employee turnover is not __J)islike moderately
too extreme, a study to calibrate the internal _Dislike very much
employee acceptance panel versus external __J)islike extremely
consumer panel results can be useful.
Generally, 40-60 office-type employees are
used for internal acceptance testing. Most Numerical values from 1-9 or 1-5 are
R&D or technical employees do not make assigned to the scales, a panel average is
legitimate panelists for acceptance testing calculated and product means are compared
because they are overexposed to product by Analysis of Variance. Frequency distri-
flavor characteristics. The scales and butions are also examined.
methods used are the same as those dis- Five-point directional scales are also
cussed under Consumer Central Location frequently used to determine optimum
Testing. levels of product characteristics such as
"saltiness," "chewiness" or "apple flavor."
An example of 5-point attribute rating
Consumer Central Location Tests scales are given below:
This testing is often performed by the
Market Research department in conjunc- Saltiness Chewiness
tion with, or independently from, the _Too salty _Too chewy
sensory function. The objective is to deter- _Slightly too salty _Slightly too chewy
mine the consumer's opinion on products. _Just right __Just right
The consumer is a user or potential user of _Slightly not salty enough _Slightly too tender
_Not salty enough _Too tender
the product being tested. "Consumers" are
generally disqualified from participating in a
consumer test on a food product if any Numerical values ranging from -2 to +2 or
member of their family works in the food, from 1 to 5 are assigned to the scale, as
market research or advertising industry. shown below:
There generally are age, sex, race, income
and lifestyle constraints as well. A minimum +2 5 Toomuch
of 75-120 subjects are used per location. +1 4 Slightly too much
Frequently as many as five cities are tested 0 3 Just right
simultaneously. In Central Location Test- -1 2 Slightly not enough
ing, the product is tested under very con- -2 1 Not enough
trolled conditions, uplike the more creative
and variable conditions that are encoun- Means, standard deviations and fre-
tered in actual home use. Generally, quency distributions are calculated for each
Central Location Testing is limited to sample. The data can first be analyzed by
analysis of appearance, texture, and flavor F-test to determine if there is a difference
characteristics. Performance and in-use in distributions of responses (variances)
information is not collectible. between two samples, and if not, then by a
 Sensory Analysis 829

chi-square analysis. The F-test is used to A first impression/gut response is probably

screen out situations such as that illustrated the more desirable statistic, which can be
in Table 20-6. measured using a single nine-point overall
acceptability scale.
TABLE 20-6. Frequency Distributions

Sample A Sample B Sensory- Instrumental Relationships

50 Too much 0 When a valid, tested relationship can be
0 Slightly too much 0 developed between the human response
0 Just right 100 and an instrument's response to a food or
0 Slightly too little 0
50 Too little 0
beverage, the instrument can be substituted
X= "Just Right" X = "Just Right" for the sensory test. These types of rela-
tionships have been successfully built
for textural attributes such as hardness,
In the table, both sample A and B are chewiness and viscosity, and with more
"just right" on the average, although not limited success for flavor ( Galetto and
one of the 100 judges rated sample A "just Bednarczyk 1975, Gillette 1984, Stone and
right." If the F test shows the two variances Sidel 1985).
to be dissimilar, the chi square test will test Substitution of instrumentation for a
for differences in distribution response sensory panel is of particular value for
between the two samples. repetitive testing, such as QA or QC testing.
Hedonic, or acceptance information can Additionally, in developing these relation-
also be obtained by conducting a two-sample ships, the underlying physical and chemical
paired preference test ("which sample do you principles responsible for flavor delivery can
prefer?"). This is essentially a directional be better understood, and thus eventually
paired comparison test (see previous section controlled. It is risky to attempt to relate
on paired comparison tests). specific instrumental measure to hedonic
There is good argument for not using any responses, as the hedonic responses are
diagnostic (too much ... too little) scales almost always non-linear. Hedonic re-
when performing consumer tests. A battery sponses are multidimensional and must be
of questions about various quality par- handled as such.
ameters may lead consumers to be overly Approaches that can be used to relate
analytical in their response to the product. sensory results to instrumental readings
include linear regression (Figure 20-3),
multiple regression, discriminant analysis
15
14
13
12
e> I I
SAGE DISCRIMINANT ANALYSIS PLOT
ZIO
~ 9
a: 8
1- 7 r•0.94
~ 6 n•60
:I: 5 TURKI5-ri
lr 4
~
0 3
~ 2
~ I
0~~·--T--r--~~.~~.~-~-,--~~--~
0 .04 .08 .12 .16 .20 .24 .28 .32 .36 .40 .44
PERCENT CAPSAICINOIDS IN RED PEPPER

FIGURE 20-3. Linear regression relating sensory FIGURE 20-4. The use of discriminant analysis for
heat rating the capsaicinoid content of red pepper. the classification of various sages.
830 Source Book of Flavors

FACTOR ANALYSIS SENSORY X INSTRUMENTAL

BLACK PEPPER

·---------SENSORY
--INSTRUMENTAL

FACTOR CITRUS
2
BLACK PEPPER GC 36 ~AROMA
AROMA • i
~- i,g~:
PIECE
SIZE
··---••,_.
'•,,,
.i ./ i /-HEAT HPLC 22
...,,.. I' Jr
........ '::;.-'
0

WOODY
AROMA
GC 9

0
FACTOR
1
FIGURE 20-5. The use of factor analysis to relate sensory attributes of
black pepper to various analytical results.

(Figure 20-4), and factor analysis (Figure
20-5).
In order to develop such models, a
significant amount of planning and a good
statistician are required. A matrix of at least
fifteen products is necessary, covering the
commercial range on all known significant
variables. If samples are of natural origin,
it can take a year or more to collect the
appropriate sample set for such a test. When
the products are easily formulated, a study
can easily be designed and implemented in a
matter of a few weeks.
Generally, the function responsible for
implementing the outcome of a sensory-
instrumental study is manufacturing, pur-
chasing or QA/QC. It is critical that these
functions are involved in the planning of
such a study, if practical implementation is
desired. Otherwise, the elegant and statis-
tically significant correlation models will
remain unimplemented in the files of R&D.
Burgard and Kuznicki (1990) have
published a practical reference manual for
the interpretation of chemical and sensory
data. ASTM (1976) has also published the
proceedings of a symposium on this topic.
SUBJECTS
Human beings provide both objective
(analytical) and subjective (affective) data
for sensory testing. It is critical to have
these human instruments properly selected,
oriented, trained and maintained, or the
data they provide will be invalid. The types
 Sensory Analysis 831

TABLE 20-7.

Affective/Hedonic Test Type of Subjects number of subjects

• Employee Acceptance Not trained. Not food, flavor 40-60

professionals or scientists.
Naive to test objectives
and project goals.
Representative of outside
consumer.
• Consumer Above criteria, plus subjects 75-200
must use the product under per location
test; meet demographic
and lifestyle criteria.

Analytical/Objective Tests

• Difference tests
-Triangle, duo-trio- Trained or untrained 36-60
Directional Paired Trained/oriented 40-60
Comparison, Ranking Must understand the
characteristics( s) being
measured.
-Signal Detection Trained or untrained 30-50
• Descriptive Analysis Fully trained, no personal 8-12
opinion allowed.
• Quality Evaluations Professionals trained on 1-10
universe of produce and
grading criteria.

of human subjects required for sensory • Smoking and Age

testing are summarized in Table 20-7. These are not important factors, although
smoke odor from a smoker will distract
other subjects. Subjects over the age of
Selection and Screening Criteria
80 may be less discriminating.
When selecting subjects for any sensory
Subjects can be recruited through:
test, the following criteria should be
considered: Internal External (non-
(employees) employees)
• Interest and Motivation
• Management • Newspaper
These are highly correlated to attendance
directives advertisements
and performance.
• Seminars • News articles on
• Availability
tasting program
For long-term panels, people who travel
• Questionnaires • Telephone
frequently or work in production may
solicitation
pose problems.
• Personal contact • Civic
• Health
organizations
Subjects should be in generally good
• Local TV
health, with no allergies/aversions to
publicity
products. Basic taste and smell function
should be tested (see screening tests).
Screening tests
• Articulateness-Literacy
Subjects must be able to communicate Panelists who are to be trained for descrip-
well in written and oral forms. tive analysis or other analytical testing
832 Source Book of Flavors

TABLE 20-8. tergreen, peppermint and/or spearmint, tur-

pentine ("paint, solvent"), vanilla, vinegar,
Concentration in Spring or
1. Basic Tastes Distilled Water
scotch, oleoresin, black pepper, ammonia.
Odors that are common to a company's own
sweet 2.0% sucrose products should be given priority. Odorants
sour 0.5% citric acid can be delivered by dropping a few drops
salt 0.3% sodium chloride
bitter 0.07% caffeine
onto a cotton ball inside a small, dark, wide-
mouth bottle, labeled with a blind code,
and capped tightly with a screw cap. Allow
TABLE 20-9.
enough headspace to concentrate the odor
Concentration in Spring and be sure that the odorant is not over-
2. Intensity Ranking or Distilled Water whelming.
sweet sucrose@ 1.0%, 2.0%,
4.0%
Other Tests
sour citric acid@ 0.25%, Before embarking on a long-term or high-
0.5%, 1.0% priority study, it is wise to devise screening
salt sodium chloride @ 0.15%, tests that will select the most sensitive
0.30%, 0.60% subjects for that product. A series of
bitter caffeine @ 0.035%,
triangle or duo-trio tests on different con-
0.07%, 0.14%
centrations of the product or different
versions of the product can be used to
should be screened for normal taste and test for subject sensitivity. More detailed
smell acuity. Subjects need not be dropped information on selection and training can
from panels because they confuse basic be found in ASTM STP 758 (1981), in
tastes such as saltiness and acidity during Meilgaard, Civille and Carr (1987) and in
screening; it may be a simple matter of Basker, D. (1988), and Leight and Warren
training. Odor is 70-80 percent of "flavor," (1988).
thus screening for odor sensitivity should be
an important part of the screening tests. A
Factors Inftuencing Sensory Measurements
basic approach to screening for taste func-
tion is described in Tables 20-8 and 20-9. In an effort to control the effects that
Provide the subject with 30 ml of each psychological factors and physical testing
solution (Table 20-8), in random order, conditions can have on human judgment,
repeating one of the samples to minimize standard laboratory procedures have been
guessing by process of elimination. developed. The psychological and physical
Provide the subjects with 20 ml of each effects (commonly called "errors" because
solution (Table 20-9), having them rank the they lead to errors in judgment) and actions
solutions in order of intensity within a that should be taken to control them are
tastant. listed in Table 20-10.

Odor Identification Test

A series of odorants is given to subjects
to determine their ability to identify, or at
least describe, commonly occurring odor-
ants. Some typical odorants include: anise
oil ("licorice, anise, fennel"), benzaldehyde
("cherry, almond"), cinnamon oil ("cinna-
mon, red-hots"), eugenol ("clove, dentist,
allspice"), lemon oil ("citrus, lemon") win-
PHYSICAL CONSIDERATIONS
OF TESTING
The conditions under which a sensory test is
executed seriously affect the outcome of the
test. Environmental odors, noise distrac-
tions, variable temperatures, inappropriate
media, etc., will transform an otherwise
well-executed test into useless results. The

TABLE 20-10.
Effect
1. Expectation Error: Any information
subjects receive about a test will
influence results. Preconceived
impressions will lead to
preconceived results.
2. Stimulus Error: In a desire to be
correct, panelists may use non-
relevant characteristics of a sample
of judge flavor, i.e., using depth of
color to judge strength of flavor.
3. Halo Effect: When more than one
characteristic of a product is being
evaluated, the subject's overall
opinion often influences each
characteristic, i.e., a vanilla flavor
rated high in vanillin aroma may
also be rated high in bourbon.
4. Contrast Effect: The presentation of
a sample of good quality or stronger
flavor just before one of poor
quality or weaker flavor causes the
panelist to rate the second sample
lower than it would normally be
rated, and vice versa.
physical requirements for valid testing relate
to the facilities and their environment, and
to the preparation and presentation of
actual samples.
Facilities
As might be expected, the ideal test facility
is a large, soundproof room, with inde-
pendent air-handling, including positive
pressure to eliminate external odors, with
an adjoining laboratory for sample prepara-
tion. However, in the absence of such a
panel room, any quiet, comfortable room
can be adapted. It is important that this
room be private when in use for sensory
testing. Facilities should also be accessible
nearby for sample preparation and cleanup.
Testing should never be conducted by
carrying samples from room to room on a
tray or cart. Judges must be free of all
distractions and bias during testing. This
cannot be accomplished when testing in the
Sensory Analysis 833
Action to Minimize Effect
• Code all products
• Keep test objectives & results secure
until test is over.
• Use naive subjects
• Don't allow discussion during a test.
• Samples must appear as uniform as
possible.
• Use red lights or covered vessels.
• Evaluate one characteristic at a
time.
• Train subjects.
• Balance the order of sample
presentation.
cafeteria, the open laboratory, or at the
judge's desk.
The seating arrangement and table space
are determined by the nature of the tests
that will be conducted in the testing facility.
For example, if only descriptive analysis will
be done, then all that is needed is a large,
preferably round, table and comfortable
chairs. If individual testing booths are occa-
sionally required, inexpensive, collapsible
fiberboard booths can easily be erected in a
few minutes for this purpose. Samples can
be wheeled in on a cart and passed around.
When most of the testing necessitates
individual booth facilities, then a different
arrangement should be considered. For
rapid service and uniform sample presenta-
tion, permanent booths should be installed
with a pass-through from the preparation
area. An ideal arrangement would be to
have a central preparative area with panel
booths on two, if not three, of the adjacent
walls. This allows the samples to be pre-
834 Source Book of Flavors
sented rapidly and also lets the panelists
enter the testing facility without passing
through the laboratory itself and viewing
the samples during their preparation. Signal
lights may be installed in each booth so that
panelists can signal their presence to the
preparation area. The panelists should not
enter the preparation area, since they might
gain information that would influence their
judgment (expectation error).
There is no one "best" design for test
facilities. Design should be situationally
customized to consider flexibility, use, and
cost. No compromise can be made, how-
ever, in regard to having a facility that
is quiet, relatively odor-free, and non-
distractive. With a little effort, these con-
ditions can be found anywhere.
Good lighting is also extremely impor-
tant. For general evaluations, as well as
many other test purposes, it is important
that the samples be viewed in natural lighting
(fluorescent-"northern daylight" works
well). If, for example, the lighting gives the
food appearance a greenish hue, then the
color of the product will usually be scored
poorly due to its unappetizing appearance.
Occasionally, special lighting must be used
to mask obvious color differences. Red is
the most common color used for masking
sample color differences; however, any
effective color (green, blue) can be used.
Sometimes a low level of illumination is
effective. Even the most basic sensory
testing facility should have some provision
for adequate "daylight" and for special
lighting effects to mask color differences.
Colored or special lighting effects should
never be used with inexperienced panels,
since the unnatural atmosphere tends to
distract and thereby influence their judg-
ment. For experienced panels, some men-
tion and at best an example of lighting
effects should be included in their orienta-
tion to panel procedures.
In 1986, ASTM published a manual
on Physical Requirement Guidelines for
Sensory Evaluation Laboratories (ASTM
1986). This manual provides detailed re-
commendations for laboratory planning and
design, as well as several case studies and
layouts.
Sample Preparation and Presentation
General
The same considerations are taken for
preparation of samples for sensory testing as
for any other type of scientific experiment.
The only variable between samples should
be the one under investigation.
Exactly the same conditions must be used
for all samples; this means that identical, if
not the same, equipment should be used
for sample preparation. Serving tempera-
ture and length of standing prior to serving
must be standardized. All samples should be
prepared with the most accurate available
measurements. Analytical balances, rather
than measuring cups and spoons, are ad-
vised, since experienced panelists can often
discriminate between even small differences
in concentration. All samples should be
presented at the same preparative time
intervals and temperatures. In most cases,
the serving temperature should be the tem-
perature that is normal for that product.
The amount of sample presented should be
constant throughout the testing and large
enough to provide the panelist with the full
effect of the sample. Always use uniform
lots or blends of product or carrier. When
a series of tests requires a common in-
gredient, secure enough of the same lot for
the entire series.
The person who is requesting the test
should provide all samples and test materials
when possible. This minimizes misunder-
standing. Obtain background information
and sample history before, not after, the
tests are conducted. The samples must be
representative and typical of the product
under test. ASTM has published tables
(ASTM 1984) of successfully used experi-
mental conditions-utensils, quantity, tem-
perature and carrier-for certain foods and
beverages. Any sensory or product evalua-
tion laboratory should maintain its own file

manual on product preparation, including
carriers (formulas for preparation), cooking
times/temperatures, cooling times/tempera-
tures, concentration levels for all ingre-
dients, serving amounts, serving vessels,
tasting procedures, etc.
Carriers/Medias
Carriers are required when it is necessary
to test a sample that is not suitable for
testing in an undiluted form. Examples of
samples that usually require carriers are
ingredients such as dehydrated vegetables,
spices, or flavors. For proper evaluation
of these materials, a test medium is re-
quired to provide a means of uniformly
dispersing and diluting the sample. The
carrier chosen for a given sample must be
simple and convenient, bland, appropriate
for the product, and reproducible; it should
possess the proper physical properties and
be non-adulterating. For a consumer or an
acceptance test, the carrier should be rep-
resentative of the final application of a
product. For an analytical test, the carrier
should be as bland and non-interfering as
possible. A brief explanation of these pro-
perties follows:
The carrier must be simple and conven-
ient, and one should avoid anything that
requires last-minute preparation or attention
and, if possible, even chilling or cooking. To
be really useful, convenience is essential.
Room temperature applesauce is a con-
venient medium for acceptance testing of
cinnamon or nutmeg, while room tempera-
ture water is the best medium for descriptive
testing.
The carrier should also be bland. While
this is not always possible, the best carriers
are not strongly flavored and provide a
subtle background that does not compete
with the sample attributes. A test medium
should be chosen that is compatible with
the sample and appropriate for the food
category. This includes avoiding combi-
nations of foods that do not usually go
together. Mashed potatoes are a bland and
appropriate carrier for acceptance testing of
Sensory Analysis 835
gravy. Gravy is best tasted straight or even
diluted for descriptive analysis.
The sample carrier should be repro-
ducible. This is needed to assure that test
results can be reproduced and verified both
by the initial investigator and by others who
desire to repeat the test or conduct related
studies at a future date. Reproducibility is
another reason why a good carrier should be
simple and convenient. The more compli-
cated the procedure, the more possibility of
difficulty in repeating the test.
It is very important that the carrier should
possess the proper physical properties to
allow it to function as it should. Therefore,
the test sample should either be soluble or
suspendable in the carrier. In addition, the
temperature of the carrier should not con-
flict with the physical properties of the
sample under investigation, e.g., hot media
should not be used for peppers or cool
media used for mint or menthol.
The carrier should represent the ultimate
use of the product and not adulterate it
through processing or other means. For
example, heat changes the flavor character
of vanilla; thus, when it is to be used in a
baked application, it should not be tested in
a cold, unheated carrier. Dehydrated onions
for soup should not just be rehydrated and
sampled, but heated in a manner similar to
soup preparation. Seasonings should not
be tested in commercial tomato sauces that
already have seasonings added.
An example of a carrier-product combi-
nation that does not fulfill these important
criteria is white sauce for spice evaluations.
Although it does suspend and partially
extract the test sample and can be made to
taste fairly bland, it is not convenient or
reproducible. The extent of variation in the
carrier thickness, temperature and topical
"skin" formation, will alter the sample's
aroma and flavor release. Retail white sauce
mixes already have flavors and seasonings
added, which will adulterate the spice under
test.
The optimal concentration of a test
sample in the carrier is the lowest concen-
836 Source Book of Flavors
tration that possesses all the appropriate
flavor and functional qualities of that
sample. Selection of the correct level usually
involves pretesting to determine the lowest
effective concentration.
It would be very convenient if a universal
carrier could be developed much like the
standard mediums or solutions for certain
biological and chemical studies. However,
since the properties of the food materials
requiring carriers are so very different,
there is no possibility of a single multipur-
pose carrier. Some carriers are appropriate
for many different purposes; biscuits, apple-
sauce, unflavored cake mix or pudding, rice,
egg and egg substitutes, mayonnaise, milk,
or water (which may be thickened slightly
with gums). There are many other food
materials that have the recommended
properties.
Carriers are not needed for all products.
In many cases, discrimination is better when
foods are tested without carriers; those that
can be consumed straight should be tested
without carriers for descriptive and differ-
ence tests. Appropriate carriers should
always be used for acceptance and prefer-
ence tests of foods; spaghetti sauce on
noodles, gravy on mashed potatoes, salad
dressing on lettuce, and icing on a cookie or
cake.
SETTING UP A SENSORY
PROGRAM
The key to implementing a successful sen-
sory program is the acquisition of a talented
and flexible professional staff. Every organ-
ization has different blends of cultural,
financial and business constraints that will
direct its sensory testing needs. There is no
one single "right" approach for building a
testing program. Too frequently, the job of
sensory testing is delegated to existing staff
with minimal training or understanding of
sensory testing. This individual learns on the
job, by studying recommended tests and/or
by attending short courses. If the individual
is broad-minded, technically flexible and
creative in his approaches to testing, this
type of situation can be successful. How-
ever, if the individual is risk-averse and
approaches all test situations "by the book,"
the sensory program is more likely to choke.
A second critical factor for assuring
success is the sincere support of manage-
ment. Since panelists are the instruments
of the sensory program, their availability
and motivation are essential. Management
and encouragement of panelist participation
is key. Ideally, panel participation should
be an important part of the organizational
culture.
Here are some recommended steps for
the sensory novice who finds himself in the
position of being asked to set up a new
sensory program:
a. Secure ASTM publications, especially
STP 913 on "Physical Requirement
Guidelines for Sensory Evaluation
Laboratories," and other recom-
mended texts (see reference section).
b. Contact professionals in the business
using a network of IFf (Institute
of Food Technologists) Sensory
Evaluation Division members, ASTM
committee E-18 (American Society
for Testing and Materials, Committee
on Sensory Evaluation), universities
and suppliers to your company. Ask
this network for advice, tours of their
facilities, written procedures they
utilize, and other practical support.
c. Attend several recognized short
courses on sensory evaluation.
d. Hire a recommended consultant to
help sell, design and kick-start your
program.
e. Adopt a flexible, innovative approach
to testing.
f. Have Fun! This is a fascinating and
satisfying technical field in which to
practice. Imagine-stimulating a
pleasure center for a living!
References
Amerine, M.A., Pangborn, R.M., and Roessler,
E. B. 1965. Principles of Sensory Evaluation of

Food. New York. Academic Press.
ASTM, 1981. STP 758; Guidelines for the
Selection and Training of Sensory Panel
Members. American Society for Testing and
Materials, 1916 Race St., Philadelphia, Pa.
ASTM, 1986. STP 913; Physical Requirement
Guidelines for Sensory Evaluation Labora-
tories, eds. Eggert, J. and Zook, K. 1916 Race
St., Philadephia, Pa.
ASTM, 1984. Standard Practice for Establishing
Conditions for Laboratory Sensory Evaluation
of Foods and Beverages. E 480-84. 1916 Race
St., Philadelphia, Pa.
ASTM, 1976. STP 594; Correlating Sensory
Objective Measurements-New Methods for
Answering Old Problems, eds. J.J. Powers
and H. Moskowitz. American Society for
Testing and Materials, 1916 Race St.,
Philadelphia, Pa.
Basker, D. 1988. Assessor Selection: Procedures
and Results. In Applied Sensory Analysis of
Foods, Volume I, ed. Howard Moskowitz,
pg. 125. Boca Raton, Fla. CRC Press.
Burgard, D.R. and Kuznicki, J.T. 1990.
Chemometrics: Chemical and Sensory Data.
Boca Raton, Fla. CRC Press.
Caul, Jean F. 1957. The Profile Method of Flavor
Analysis. In Advances in Food Research,
Volume VII, eds. E.M. Mrak and G.F.
Stewart, pp. 1-40. New York. Academic
Press 7:1-40.
Galetto, W.G. and Bednarczyk, A.A. 1975.
Relative Flavor Contribution of Individual
Volatile Components of the Oil of Onion.
J. Food Sci. 40(6):1165-67.
Gillette, M. 1984. Applications of Descriptive
Analysis. J. Food Protection. 47(5):403-9.
Larmond, Elizabeth. 1977. Laboratory Methods
for Sensory Evaluation of Food. Agriculture
Canada, Ottawa: Canadian Government
Publishing Centre.
Leight, R.S. and Warren, C.B. 1988. Standing
Panels Using Magnitude Estimation for
Research and Product Development. In
Sensory Analysis 837
Applied Sensory Analysis of Foods, ed.
Howard Moskowitz. Volume 1, pg. 225. Boca
Raton, Fla. CRC Press.
Meilgaard, M., Civille, G.V., and Carr, B.T.
1987. Sensory Evaluation Techniques. New
York. CRC Press.
Newell, G.J. and MacFarlane, J.D. 1987.
Expanded Tables for Multiple Comparison
Procedures in the Analysis of Ranked Data.
Food Sci. Vol. 52(6):1721-25.
O'Mahony, M.A.P.D. 1983. Adapting Short Cut
Signal Detection Measures to the Problem
of Multiple Difference Testing. In Sensory
Quality in Foods and Beverages: Definition,
Measurement and Control, ed. A.A. Williams
and R.K. Atkin, pp. 69-81. England: Ellis
Horwood, Ltd.
O'Mahoney, Michael. 1988. Applied Sensory
Analysis of Foods: In Sensory Difference and
Preference Testing: The Use of Signal Detec-
tion Measures: Volume I, ed. Moskowitz,
Howard. Pg. 145. Boca Raton, Fla. CRC
Press.
O'Mahoney, Michael. 1986. Sensory Evaluation
of Food, Statistical Methods and Procedures.
New York. Marcel Dekker, Inc.
Roessler, E.B., Pangborn, R.M., Sidel, J.L.,
and Stone, H. 1978. Expanded Statistical
Tables for Estimating Significance in Paired-
Preference, Paired-Difference, Duo-Trio and
Triangle Tests. Food Sci. Volume 43,
pp. 940-947.
Stone, Herbert and Sidel, Joel. 1985. Sensory
Evaluation Practices. New York. Academic
Press, Inc.
Stone, Herbert, Sidel, J., Oliver, S., Woolsey,
A., and Singleton, R.C. 1974. Sensory
Evaluation by Quantitative Descriptive
Analysis. Food Techno/. 28(11):24-34.
Zook, K.L. and Pearce, J.H. 1988. Quantitative
Descriptive Analysis. In Applied Sensory
Analysis of Foods: Volume 1, ed. Howard
Moskowitz, pg. 43. Boca Raton, Fla. CRC
Press.
Chapter 21
The Safety of Flavorings
Friedrich Grundschober
International Organization of the Flavor Industry
Geneva, Switzerland

INTRODUCTION usually unquantified, subject to multiple

confounding factors and readily usable only
The nutritional requirements of humans for acute effects. For most single chemical
can be met by a nearly endless variety of substances, or definable mixtures, toxico-
sources. Food is not merely a biological logical testing in animals-if preceded,
necessity, but also an aesthetic experience guided and interpreted by appropriate
and a cultural expression. The food choices metabolic and pharmacokinetic studies-
we make depend on cultural, economic and offers the best insight into the nature and
even genetic factors, as well as personal potency of their toxic effects. Empirical
preferences. One of the most important observation long ago suggested the dominant
characteristics of food that influences our role of doses in determining toxic hazard
choices is its flavor. It is not sufficient that (Paracelsus 1564). Accumulated experi-
foods meet basic nutritional requirements, ence, combined with information from com-
it is also necessary that foods be well parative metabolism and pharmacokinetics,
accepted. The role of flavors in the accept- permits the use of structural relationships
ance of foods is essential. to foresee possible toxic and pharmacologic
Our food supplies are diverse and ex- effects.
ceedingly complex in composition. Our Animal tests provide data on the nature
knowledge of the safety of that complex and and potency of toxic effects of a substance.
varying food supply depends primarily on The data from animal feeding studies are
two sources: translated into a summary figure in order
to assist in their effective use. This figure
1. Human experience. is called the acceptable daily intake, the
2. Toxicological evaluation, including "ADI."
information from metabolism and
pharmacokinetics.
The Safety Evaluation of Food Additives
Most of our confidence in the safety One of the leading groups evaluating toxico-
of food comes from accumulated human logical data is the Joint FAO/WHO Expert
experience, even though this experience is Committee on Food Additives (JECFA).
838

JECFA evaluates results from subchronic
or long-term animal feeding studies at
several dose levels and determines the "no
observed adverse effect level" (NOAEL or
NOEL) for food additives. This is usually
defined as the highest feeding level at which
no adverse effects were observed that were
attributable to the test substance. In order
to use this result to assess human safety, the
no-effect level is divided by a safety factor.
Very often this safety factor is 100, rational-
ized as a factor of 10 for differences between
individuals and 10 for differences between
species. The result is the acceptable daily
intake (ADI), expressed either in mg/kg of
body weight or as "not specified." That is
the amount of an additive that can be taken
daily in the diet, even over a lifetime, with-
out risk (WHO 1974).
The ADI is intended as guidance for
national health authorities to regulate food
ingredients that may require limitations on
their use. It is a guideline level against which
to measure the potential risk of an additive.
If the ADI is "not specified," this means the
no-effect level is so high that restrictions are
not necessary. If the ADI is expressed as
mg/kg-bwt, then the potential intake of
the additive from all known food uses may
need at least to be estimated, or sometimes
calculated.
These calculations are based on the tech-
nological useful concentrations of the ad-
ditive in different foods and on the average
serving size and eating frequency of these
foods. For purposes of rough estimation it is
assumed that all food products in a given
food category may contain the additive at
the highest possible doses.
Authorities compare these theoretical
figures with the available ADI, and may
thus decide to authorize an additive for
one food and another additive of the same
category for another food, or they may set
quantitative limits on usage. This procedure
for food additives that are consumed daily
over the whole lifetime of consumers leads
to the establishing of positive lists mentioning
the authorized substances and their limita-
The Safety of Flavorings 839
tions. Only authorized substances can be
used to the exclusion of all others.
This system is well established for food
additives such as antioxidants, preservatives,
etc. JECFA tried at its 11th Session (WHO
1968) to evaluate flavoring substances in the
same way, but it became obvious that such
a procedure is not feasible. It is simply
not possible for a committee to evaluate
thousands of substances one after the other.
There is not enough time available to dis-
cuss each substance in detail, and it is
neither possible nor necessary to obtain all
the animal test data needed for a detailed
evaluation of every substance.
Differences Between Food Additives and
Flavoring Substances
Food additives have certain specific and
characteristic properties:
• The number of additives in a functional
group is limited (generally <10).
• A food additive is generally used in many
food categories.
• The technological useful concentration is
relatively high (often > 1,000 ppm, most
>100ppm).
• The technological useful concentration
range is narrow.
• The volume used in the U.S. or European
food supply is relatively large (many
> 166 kg/yr, most > 105 kg/yr).
• The consumer is normally not aware of
the presence of the additive in the foods
and may consume it daily.
• Overuse will not usually render the food
unpalatable and the consumer is neither
protected against nor aware of accidental
overdosing.
• The additive occurs rarely naturally in
foods; it is added to the food product by
the manufacturer.
In comparison, the situation of flavoring
substances is significantly different:
• Several thousand flavoring substances are
known and up to a hundred different sub-
840 Source Book of Flavors
stances may be used to obtain a specific
flavor effect.
• Few flavoring substances are used in
many food categories; certain flavor notes
can be used only for certain food products
(e.g., cocoa, garlic, etc.), many flavoring
substances will therefore only be con-
sumed in a limited number of foods. Also
the foods in a given food category will not
all have the same flavor.
• Nearly all flavoring substances are used
at concentrations <l,OOOppm, most at
<lOOppm, the majority at <lOppm and
many at <lppm.
• The technological useful concentration
range is large; it may be situated some-
where between the self-limiting concen-
tration and the threshold of perception,
depending on the type of flavor desired.
• The worldwide volume of use of flavoring
substances is relatively low (very few
>106 g/yr, 80 per cent< 5 X 104 g/yr).
• Consumers are aware of the presence of
flavorings and often choose food on the
basis of the flavor. There seems to be an
innate drive to seek variation in diet.
Consumers are therefore likely to choose
differently flavored foods with the con-
sequence that they seldom-if ever-
consume the same substance every day
through a whole lifetime.
• Flavoring substances are generally self-
limiting in use since an overdosage
typically makes the food unpalatable.
• Many foods are inherently flavored.
These are a source of flavoring substances
that are a part of the human diet. Most
flavoring substances are consumed mainly
as a result of their natural occurrence.
That the safety evaluation of flavoring
substances is different from the safety
evaluation of food additives in general has
been recognized by JECFA. It states in its
17th report (WHO 1974) that the problem
of evaluating flavoring substances is one
that cannot be solved simply by adopting
the processes traditionally used to evaluate
other types of food additives. In its 20th
report (WHO 1976), JECFA considered
the vast number of flavoring substances and
agreed to establish an order of priority for
their evaluation.
Among the factors to be considered in
proposing these priorities, the most impor-
tant are:
• The total amount of each substance likely
to be consumed by the average person.
• The similarity of the chemical structure to
that of substances of known toxicological
and biochemical properties.
• The nature and source of the substance.
Priority Setting
In discussing the setting of priorities for
testing and evaluation of food additives in
its 22nd report (WHO 1978), JECFA
recognized that it would be impossible
to undertake full toxicological studies with
all known substances within a reasonable
period. Furthermore, to carry out such
studies assigning equal importance to sub-
stances posing unequal risks would be a
waste of effort.
Substances with the lowest priority for
testing and evaluation are those that, in
their structural characteristics, are not
related to substances of demonstrated
toxicity and are consumed in very small
quantities. Compounds with a high priority
either have structural features known to be
associated with toxicity or are of unknown
toxic potential and are present in human
food in appreciable quantities.
These recommendations of JECFA gave
general indications how to proceed, but
more detailed rules are needed for priority
setting for the safety evaluation of flavoring
substances.
The first definite criteria for priority
setting proposed by JECFA were an esti-
mated per capita consumption exceeding
3.65mg per year, use in food at a level
higher than 10 mg per kg of food and valid
reasons for doubting the safety of a par-
ticular substance (WHO 1968). Another

approach for priority setting based on the
Consumption Ratio was proposed by J.
Stofberg (Stofberg 1981; Stofberg and
Kirschman, 1985; Grundschober and
Stofberg 1986; Stofberg 1988).
The discussion continued in the Codex
Committee on Food Additives, a subsidiary
of the Codex Alimentarius Commission
of the Joint FAO/WHO Food Standards
Programme. It was recognized at the 16th
Session that the consumption ratio is a valu-
able tool in setting priorities. At its 19th
session, the U.S. delegation presented a de-
tailed proposition for calculating priorities
based on structure-activity considerations,
volume of use, consumption ratios and
toxicity data if available. A Joint Council
of Europe/Commission of the European
Communities Workshop on a priority
ranking system for flavorings assessed the
validity of five propositions made for a
priority ranking system. The Workshop
chooses a method (Rulis et al. 1988) that
was also endorsed by the Codex Committee
on Food Additives and approved at the 33rd
session of JECFA (WHO 1989).
This Codex priority ranking method has
been applied to substances included in a
waiting list of the Codex, the Codex List B,
as well as to nature-identical and artificial
flavoring substances having an average
exposure of more than 0.5 mg/capita/year
and a consumption ratio of less than 10.
The selection of substances of highest
priority for the agenda of the JECFA
meetings in the coming years is now under-
taken by an International Committee on
Flavor Priority Setting.
The calculation of the priority ranking
starts with the determination of an initial
ranking based on probable addition levels
to food, and on presumptive toxicity as
inferred from chemical structure. Two
schemes employing such data elements have
been developed in recent years in the
United States. These methods are, respec-
tively, the FEMA Decision Tree (Cramer,
Ford and Hall1978) and the FDA Redbook
(FDA 1982; Rulis et al. 1984).
The Safety of Flavorings 841
The Decision Tree as well as the Red book
classify all substances in three categories
based on chemical structure. When these
categories are combined with the levels of
human exposure, all substances are assigned
to one of four "FEMA Concern Levels" and
to one of three "Redbook Concern Levels."
The results of the two systems are combined
to give "Hybrid Priority Levels." Since
there are four FEMA levels and three FDA
levels, the combination of these figures gives
hybrid priority levels between seven and
two. It must be noted that exposure receives
much more "weight" in both schemes than
chemical structure.
Exposure data are based on the annual
quantities used by the flavor industry. Joint
surveys were organized in the U.S.A. by
the National Academy of Sciences and the
Flavor and Extract Manufacturers' Associa-
tion (National Research Council 1984). A
worldwide survey on the use of artificial
flavoring substances was undertaken by the
International Organization of the Flavor
Industry (IOFI) (Grundschober et al. 1975).
A comparison of U.S. and European uses
was also made. It was concluded that
although differences were found to exist
between U.S. and European figures, these
were of no significance in the context of
priority setting (Cadby 1990).
This initial priority ranking is corrected
in the next step by the consumption ratio
adjustment. The consumption ratio (CR)
compares the average intake of a flavoring
material as a component of natural and
traditional foods, with the average intake of
the same material intentionally added to
food by the flavor industry (Stofberg 1981).
The CR of a material is defined as the
numerical ratio of the intake in milligrams
per kilogram per day (mg/kg/d) from tradi-
tional food source, to the intake in mg/kg/d
from intentional addition to food. If the CR
of a flavoring substance is more than 1, this
substance is consumed predominantly as
an ingredient of foods, and it is food pre-
dominant, while a smaller CR signifies that
the compound is largely added. By defini-
842 Source Book of Flavors
tion, a CR of zero signifies that the com-
pound is entirely added with no amount yet
found to occur naturally in food. CR values
so far compiled for a number of flavoring
materials range from very small (1 x 10-3 )
to quite large (1 x 105) (Stofberg and
Grundschober 1987).
It can be argued that the priority for
toxicological scrutiny of food-predominant
flavoring substances ought to be adjusted
downward because so much of the intake of
food-predominant materials is tolerated as
part of the traditional food supply. Wide-
spread natural occurrence in the diet implies
that no adverse effects are now known to
be associated with normal patterns of con-
sumption offoods containing that substance.
Natural occurrence clearly is no absolute
guarantee of safety, but the CR is highly
relevant to understanding and dealing with
whatever risk there may be. A CR of 1,000
means that only 0.1 percent of human intake
is from intentional use and that 99.9 percent
is from natural occurrence. Any effective
effort to reduce intake would thus have to
deal primarily, if not exclusively, with those
typically widespread natural sources within
traditional diets.
A large consumption ratio of 100 or more
also assures that variations in the sources
of a substance due to individual dietary
variations will not, in these uncommon indi-
vidual cases, alter the fact that the intake of
the substance comes largely from natural
food sources. Low CR value, approaching
one, does not carry that assurance.
A high CR indicates, however, that the
actual total intake of a substance is higher
than the intake previously estimated on the
basis of intentional use. If the presumptive
risk is already low, then greater actual
intake will still not increase presumptive risk
to a level demanding attention. But if the
presumptive risk is relatively high, a high
CR, by indicating still higher intake, in-
creases that risk even more, while at the
same time posing the very difficult problem
of what, if any, control measures will be
effective.
These considerations are the justification
for the following rules, using the consump-
tion ratio adjustment for an increase or a
reduction of the concern levels, as the case
may be:
• The CR has no effect if a substance is in
hybrid priority level 7 (there is little use in
raising it above the highest level).
• If it is in level 6, however, a CR value of
> 100 raises the level by one.
• Substances in level 5 are unaffected by the
CR.
• Substances in level 4 or below have their
level reduced by the logarithm of CR
(rounded to the nearest integer) to levels
no lower than zero. This means that CR
over 3,200 reduces 4levels, CR 3,200-320
reduces 3 levels, CR 322-32 reduces 2
levels and CR 32-3 reduces 1 level.
The final priority-level assignment is
made after adjustment for toxicological
data. Several of these considerations are
simply based on common sense, e.g., that
seriously adverse data not previously evalu-
ated by JECFA raise the substance to
the highest priority level, whereas a prior
JECFA review that resulted in a specific
ADI or an ADI "not specified" reduces the
priority level to zero.
Data from chronic and subchronic studies,
showing no adverse effects at feeding levels
1,000 x probable daily intake, from sub-
stances in priority levels five and below,
reduce the priority by three levels.
Data from mutagenicity tests have no
weight unless, in the absence of chronic
data, the results from two or more different
tests are positive for mutagenicity. Data
from LD50 tests have weight only in the
absence of data from repeated dose studies
and then only if the LD50 is less than
100 mg/kg. Data of poor quality have no
weight unless seriously adverse.
Since most substances with toxicological
data have already been evaluated for their
safety, the system for priority setting is
therefore really useful for those flavoring
substances without extensive toxicological

data. There are so many substances known
that it is simply not possible for a committee
to evaluate thousands of substances one
after the other. There is not enough time
available to discuss each substance in detail,
but it is also impossible to obtain all the
animal test data needed for a detailed
evaluation.
For these reasons, it has been proposed
to use the generally accepted procedure for
priority setting as a basis for the worldwide
harmonization of flavor regulations. All
chemically defined flavoring substances
should be classified according to this pro-
cedure. Substances in the lowest priority
number rankings-3, 2 and 1-should be
given "temporarily permissible" status.
These substances could then be used under
the conditions based on which their priority
ranking had been determined.
All substances in the higher priority
rankings-7, 6, 5 and 4-would have to
be evaluated for safety in descending order
of their ranking. Safety evaluations already
performed by a panel of experts would
be fully taken into consideration and no
repetition of evaluations would be needed
(Stofberg 1990).
The Safety Evaluation of Flavoring
Substances
Thousands of flavoring substances are
known and are consumed by man in his diet.
The safety of several hundred of these
flavoring substances has been evaluated by
groups of national experts in the U.S.A.,
the U.K., Germany, the Netherlands and
other industrialized countries, as well as by
a regional group of experts of the Council of
Europe, Partial Agreement.
GRAS Substances
The first and the most important activity in
this field was initiated in 1960 in the U.S.A.,
and this work is still continuing (Oser and
Hall1977).
The statutory definition of the term "food
additive" in the Federal Food, Drug and
The Safety of Flavorings 843
Cosmetic Act exempts any substance
"generally recognized, among experts
qualified by scientific training and experi-
ence to evaluate its safety, as having been
adequately shown through scientific pro-
cedures (or, in the case of a substance used
in food prior to January 1, 1958, through
either scientific procedures or experience
based on common use in food) to be safe
under the conditions of its intended use."
This provision has come to be designated by
the acronym "GRAS." It should be em-
phasized that recognition of safety rests on
the opinion of qualified experts, not limited
to those in the regulatory agency, and relates
specifically to the conditions of use of sub-
stance in food.
In response to the Food Additives
Amendment, in 1960 the Flavor and Extract
Manufacturers' Association (FEMA) organ-
ized a panel of expert scientists, not affiliated
with the flavor industry but with special
competence in toxicology, pharmacology
and biochemistry, to evaluate the "GRAS
status" of the hundreds of organic chemicals
contained in natural and artificial foods and
flavors (Hall and Oser 1961). The Food and
Drug Administration was kept informed of
this activity of FEMA. Subsequent to the
release in 1965 of the first GRAS list of
some 1,100 flavoring substances and their
use levels (Hall and Oser 1965), the FDA
temporarily waived bulk labeling require-
ments and adopted virtually the entire
list (21 CFR 121.1163 and 121.1164; now
21 CFR 172.510, 182.10, 182.20, 182.40,
182.50 for natural flavoring substances
and 21 CFR 172.515, 182.60 for synthetic
flavoring substances).
It may be noted that "scientific pro-
cedures" as defined in the original regula-
tions included "not only original animal,
analytical, and other scientific studies, but
also an unprejudiced compilation of reliable
information, both favorable and unfavor-
able, drawn from the scientific literature
(21 CFR 121.1h)." It was later proposed
to modify this definition to include "those
human, animal, analytical and other scien-
844 Source Book of Flavors
tific studies, whether published or unpub-
lished, appropriate to establish the safety of
a substance (21 CFR 170.3)."
It is within the spirit of these definitions
that the panel has evaluated the safety of
flavoring substances. The results of these
studies have been reported in a series of
papers in Food Technology (Hall and Oser
1965, 1970; Oser and Hall 1972; Oser and
Ford 1973a,b, 1974, 1975, 1977, 1978, 1979;
Oser, Ford and Bernard 1984; Oser et al.
1985 and Burdock et al. 1990). The publi-
cations GRAS 3 to GRAS 15 cover sub-
stances with FEMA numbers 2,001 to 3,774
and report names, synonyms and average
maximum use levels in foods. The panel
employed these use levels as basis for its
judgment that the substances are generally
recognized as safe for their intended uses.
These figures do not have the meaning of
limits or restrictions (Hall and Oser 1965).
The principles and rationale adopted in
evaluating the safety of present or proposed
flavoring substances to determine whether
or not such ingredients can be regarded as
GRAS have been described in the above
cited reports and summarized in a presenta-
tion by the late Dr. Horace W. Gerarde
(1973), a member of the panel as well as by
Oser and Hall (1977) and Woods and Doull
(1991).
The evaluation of the safety of flavorings,
as practiced by the panel, involves the
simultaneous application of a series of
criteria, every one of which must be con-
sidered in arriving at a determination of
safety-in-use. No single criterion is used to
the exclusion of others or is expected to
require absolute, independent justification.
Instead, all must be mutually supportive and
unanimously agreed upon for a conclusion
on safety to be reached. These criteria
are:
• Chemical identity.
• Structure and purity.
• Natural occurrence of the chemical in
food.
• Concentration of the chemical in food and
in the total diet.
• Toxicological evidence in animals and
man.
• Metabolic fate in mammals.
The process of safety evaluation of
flavoring substances involves a balanced
appraisal of all available information rel-
evant to the above criteria, whether or not
the data or any specific criterion are ade-
quate either in amount or in kind. The
FDA has acknowledged: "It is impossible
in the present state of scientific knowledge
to establish with complete certainty the
absolute harmlessness of the use of any
substance. Safety may be determined by
scientific procedures or by general recogni-
tion of safety." (21 CFR 170.3 (i) 1976.)
However, reasonable conclusions con-
cerning safety can be arrived at even where
animal data are lacking.
A panel decision must be regarded as
a value judgment taking into account all
relevant factors. From the beginning of
its operations, the panel has considered
each flavoring substance on an individual
substance-by-substance basis with due regard
to other compounds related by chemical
structure or biological properties.
Lists of flavoring substances declared to
be safe for their intended uses in major food
classes have been published periodically in
order to expose the panel's judgments to
scrutiny and possible criticism. The absence
of sustainable challenge after a suitable,
prolonged period following publication
lends added support to GRAS status. In the
event of a successful challenge, the sub-
stance in question is denied GRAS status.
In a few instances, the panel has with-
drawn the GRAS status after review and
consideration of new evidence. The fol-
lowing eight materials have lost their GRAS
status: 2016 Alkanet root extract (Alkanna
tinctoria Tausch), 2168 Brominated vegeta-
ble oils, 2277 Calamus oil and 2566 2-
Hexyl-4-acetoxytetrahydrofuran (Hall and
Oser 1970); 2786 3-Nonanon-1-yl acetate
(Oser and Hall 1972); 3211 2-Methyl-5-
vinylpyrazine, 3248 o-Vinylanisole and 2758
Musk ambrette (Oser, Ford and Bernard

1984). The FDA has also prohibited from
direct addition to food: Coumarin and Tonka
bean extract, Safrole, Dihydrosafrole,
Sassafras oil and Calamus oil (21 CFR
189.1).
The data used for the safety evaluation
of GRAS substances have been published in
the form of Scientific Literature Reviews
(SLR), prepared by FEMA originally under
contract with the FDA.
The SLRs cover groups of substances
with related chemical structures and, there-
fore, presumably, related metabolic and
toxicologic properties. For example, SLR
Al covers 65 substances from related
chemical classes. The titles of these SLRs
together with their order number are listed
in Flavor and Fragrance Materials (Anon
1989). This publication contains for each
GRAS substance an alphanumeric code to
the SLR. The SLRs are available either
paperbound or on microfiche from the
Customer Service National Technical Infor-
mation Services (NTIS), 5285 Port Royal
Road, Springfield, VA 22161; 703/487-
4660.
FEMA continues to sponsor research on
the safety of individual and structurally
related classes of flavoring substances. Such
work has resulted in publications on
cinnamyl anthranilate (Anthony et al. 1983;
Caldwell et al. 1985) as well as trans-anethole
(Caldwell et al. 1983; Sangster et al. 1984b;
Sangster et al. 1984a) p-propylanisole
(Sangster et al. 1983), eugenol (Caldwell
et al. 1985; Sutton et al. 1985) and benzyl
acetate (Caldwell and Chidgey 1985). Work
continues on the metabolism of substituted
propyl benzene substances, cinnamyl com-
pounds and benzyl acetate.
The most recent 15th GRAS publication
(Burdock et al. 1990) gives the current
membership of the panel. The panel
reviewed the safety of d-limonene in light
of the findings of the NTP bioassay (NIH,
1988) and discussed alpha 2 f.,l-globulin
nephropathy and tumor formation in male
rats. After careful review of all the toxico-
logy, pathology and related studies, the
panel concluded that d-limonene presents
The Safety of Flavorings 845
no risk for human use and recommended
that under the conditions of intended use
as a flavoring substance, d-limonene con-
tinues to be generally recognized as safe for
humans.
Council ofEurope Blue Book
A Committee of Experts on flavoring sub-
stances of the Council of Europe, Partial
Agreement in the Social and Public Health
Field has published lists of flavoring sub-
stances and natural sources of flavorings.
The third edition of the Blue Book (Council
of Europe 1981) contains a list of botanical
and zoological source materials, subdivided
into fruits and vegetables (N1), plants
including herbs, spices and seasonings
whose use are acceptable (N2), plants with
a long history of use that are temporarily
acceptable (N3) and plants which are used,
but cannot be classified owing to insufficient
information (N4).
The use of certain source materials for
flavorings may be limited by the presence of
an active principle* whose limit in the final
product should not be exceeded. These
limits for active principles, (e.g., ~-asarone,
quassine, quinine, safrole, thujones, etc.)
have been used for many national regula-
tions, for the Codex Guidelines and for the
EC Flavor Directive.
The defined flavoring substances are
divided into List 1 (No.1-761), of flavoring
substances that may be added to foodstuffs
without hazard to public health, and List 2
(No. 2001-2353), of flavoring substances
that may be added temporarily to foodstuffs
without hazard to public health. Most of
these substances have already been pre-
viously evaluated by FEMA and FDA;
however, the GRAS substances evaluated
during the last fifteen years have not been
considered by the Council of Europe ex-
*An active principle in a natural flavouring source
material is a chemically defined substance for
which, due to existing toxicological data, it
appears necessary to set a maximum concentra-
tion limit in foodstuffs as consumed.
846 Source Book of Flavors

perts. Specific limits in foods and beverages after evaluation by experts of the Dutch
are proposed for many substances; in some government.
instances, these limits are considerably lower The list of artificial flavoring substances
than the average maximum use levels of the in the German Aromenverordnung is rather
substances, as determined by inquiries in short. Experts of the Bundesgesundheitsamt
the U.S.A. have evaluated the safety of these artificial
A 4th Edition of the list of defined substances. They also reviewed the use of
flavoring substances has been prepared and natural and nature-identical flavoring sub-
its publication was scheduled for 1991. The stances and issued a negative list of source
list will be issued in a loose-leaf folder and materials and a restrictive list of active
more detailed information and data will be principles.
given for each substance. It seems that no Lists of artificial flavoring substances of
new substances will be included in the 4th variable length can also be found in Spain,
Edition and that several substances from the Italy and Austria.
3rd Edition will be deleted. The list of flavoring substances in Japan
The Council of Europe has also pro- contains individual substances and chemical
moted the setting of priorities. The Codex groups. Experts on flavor standardization
Method for priority setting was originally are working on a Chinese list of flavoring
chosen at a Workshop organized by the substances.
Council of Europe (Rulis eta!. 1988). These
activities are in contradiction with the FAO!WHO
requirements for the evaluation of new The Joint FAO/WHO Expert Committee
flavoring substances, laid down in the 3rd on Food Additives studied at its 11th meeting
Edition of the Blue Book. (WHO 1968) 41 flavoring substances and
The Council of Europe experts are also established acceptable daily intakes for 35.
discussing smoke flavorings and process The JECFA did not continue the systematic
flavorings, but results of practical interest evaluation of flavoring substances, but
have not yet been published. The experts evaluated from time to time a few sub-
require the submission of analytical data stances of particular interest. At present,
and toxicological data for individual pro- new flavoring substances on the agenda of
ducts. This information may lead to the JECFA have been selected by the Codex
definition of certain raw materials and method for priority setting.
process conditions that could be considered A method for priority setting has not
as acceptable, but no decision has been yet been elaborated for natural source
reached so far. materials. At its 25th meeting (WHO, 1981)
JECFA evaluated several active principles.
Evaluations by National Groups It was concluded that it was not appropriate
The Food Additives and Contaminants to allocate an ADI for ~-asarone, a con-
Committee in the U.K. has published a stituent of oil of calamus. The JECFA
report on the review of flavorings in food in recommended that if oil of calamus is used,
1976. This report contains the lists of the it should contain the lowest practical level of
2nd Edition of the Council of Europe Blue ~-asarone. Coumarin should not be used as
Book. The report was never updated. a food additive, but for coumarin-containing
The Dutch flavor regulation contains a natural source materials, the level of use
long list of artificial flavoring substances. should be restricted to the minimum neces-
The large majority of these substances sary to produce the desired organoleptic
have already been evaluated by the experts effect. Source materials containing safrole
of FEMA and/or the Council of Europe. or isosafrole as the principal ingredient
A few additional substances were added should not be used, but it is not practicable

to advocate the discontinuance of spices
containing safrole or isosafrole as minor
constituents (e.g., nutmeg, mace and cinna-
mon). However, when these spices are
used, safrole and isosafrole in the finished
product should be kept to the absolute mini-
mum. Also, the amounts of thujone isomers
in foods and beverages resulting from the
addition of thujone-containing flavoring
agents (e.g., sage) should be reduced to the
lowest practicable level.
The FAO/WHO Codex Alimentarius
Commission has adopted General Require-
ments for natural flavorings (Codex 1988).
This text contains a restrictive list of active
principles and, as an annex, literature refer-
ences for lists of natural source materials.
European Communities
The Flavor Directive (EEC 1988) is based
on the conclusions of the EC Scientific
Committee for Food concerning heavy
metals, contaminants and active principles.
It is required that flavorings contain no
more than 3 mg/kg As, 10 mg/kg Pb, 1 mg/
kg Cd and 1 mg/kg Hg.
The maximum limit of 0.03j.!g/kg 3,4-
benzopyrene, introduced by the use of
flavorings in foodstuffs, can be met by the
application of special purification steps
during the fabrication of smoke flavorings.
Of particular interest is the Annex II
(Table 21-1) of the Directive, with maxi-
mum limits for certain active principles,
reproduced in the attachment.
Another safety-related provision of the
Directive is the requirement to limit the
reaction temperature of process flavorings
to 180°C for a period not exceeding 15
minutes.
At the same time as the Directive, the
EC Council of Ministers has also adopted a
Council decision, asking the EC Commis-
sion to establish an inventory of the fol-
lowing categories of source materials and
flavoring substances:
• Flavoring sources composed of food-
stuffs, and of herbs and spices normally
considered as foods.
The Safety of Flavorings 847
• Flavoring sources composed of vegetable
or animal raw materials not normally con-
sidered as foods.
• Flavoring substances obtained by
appropriate physical processes or by
enzymatic or microbiological pro-
cesses from vegetable or animal raw
materials.
• Chemically synthesized or chemically
isolated flavoring substances that are
chemically identical to flavoring sub-
stances naturally present in foodstuffs or
in herbs and spices normally considered
as foods.
• Chemically synthesized or chemically
isolated flavoring substances that are
chemically identical to flavoring sub-
stances naturally present in vegetable, or
animal raw materials not normally con-
sidered as foods.
• Chemically synthesized or chemically
isolated flavoring substances other than
those referred to above (the artificial
flavoring substances).
• Source materials used for the produc-
tion of smoke flavorings and process
flavorings, and the reaction conditions
under which they are prepared.
The flavor industry, represented by IOFI
and the European Flavour and Fragrance
Association [EFFA] (previously Bureau de
Liaison) has prepared and transmitted draft
inventories of natural source materials (lists
of plants and animals) and of defined
natural and nature-identical flavoring sub-
stances, indicating whether the natural
source is considered as food or not. An
inventory of artificial flavoring substances
was also transmitted, as well as the IOFI
Guidelines for smoke flavorings and process
flavorings (IOFI 1990).
The EC Commission is interested in har-
monizing legislation and has expressed its
intention to avoid duplication of efforts. It is
unlikely that the EC Scientific Committee
for Food will be asked to reevaluate individ-
ual flavoring substances. It can be expected
that all flavoring substances evaluated by
848 Source Book of Flavors

TABLE 21-1. Maximum Limits for Certain Substances Obtained from Flavorings and Other Food Ingredients
with Flavouring Properties Present in Foodstuffs as Consumed in Which Flavourings Have Been
Used

Foodstuffs Beverages
Substances• mg/kg mg/kg Exceptions and/or Special Restrictions

Agaric acid 20 20 100mg/kg in alcoholic beverages and

foodstuffs containing mushrooms
Aloin 0,1 0,1 50 mg/kg in alcoholic beverages
Beta Asarone 0,1 0,1 1 mg/kg in alcoholic beverages and
seasonings used in snack foods
Berberine 0,1 0,1 10mg/kg in alcoholic beverages
Coumarin 2 2 10 mglkg in certain types of caramel
confectionery
50 mg/kg in chewing gum
10 mg/kg in alcoholic beverages
Hydrocyanic acid 50 mg/kg in nougat, marzipan or its
substitutes or similar products
1 mg/% volume of alcohol in alcoholic
beverages
5 mg/kg in canned stone fruit
Hypericine 0,1 0,1 10 mg/kg in alcoholic beverages
1 mg/kg in confectionery
Pule gone 25 100 250 mg/kg in mint or peppermint-
flavoured beverages
350 mg/kg in mint confectionery
Quassine 5 5 10 mg/kg in confectionery in pastille
form 50 mg/kg in alcoholic beverages
Safrole and isosafrole 2 mg/kg in alcoholic beverges with not
more than 25% volume of alcohol
5 mg/kg in alcoholic beverages with
more than 25% volume of alcohol
15 mg/kg in foodstuffs containing
mace and nutmeg
Santonin 0,1 0,1 1 mg/kg in alcoholic beverages with
more than 25% volume of alcohol
Thuyone (alpha and beta) 0,5 0,5 5 mg/kg in alcoholic beverages with
not more than 25% volume of
alcohol
10 mg/kg in alcoholic beverages with
more than 25% volume of alcohol
25 mg/kg in foodstuffs containing
preparations based on sage
35 mg/kg in bitters
• May not be added as such to foodstuffs or to flavourings. May be present in a foodstuff either naturally or following the addition of
flavourings prepared from natural raw materials.

one group of experts will be acceptable
in the EC Member States.
Conclusions
The safety evaluation of flavoring substances
will be concentrated on the evaluation of
substances of high priority, as determined
by the Codex method for priority setting.
All substances of large use have already
been evaluated, and additional evaluations
will be needed only for the few substances
with newly reported adverse toxicological
findings.
With regard to new nature-identical
flavoring substances, it should be noted that

they have all been discovered as new trace
components among already known more
important elements of natural flavors; there-
fore, in order to be noticeable they have to
be powerful and will inevitably be used at
a very low dosage. Accordingly, their use
is very low and the collection of the data
needed for priority setting will show that
their priority for further evaluation is also
very low. In the absence of countervailing
information, substances of low priority
should be generally recognized as safe.
It is expected that also in the future there
will be no positive list of all natural
flavoring substances. The safe use of natural
source materials can be assured by the
restriction of the toxicologically important
active principles. Natural and nature-
identical flavoring substances will be listed
in inventories and have to be submitted to
priority setting. There is a large consensus
that artificial flavoring substances should be
used only after an expert safety evaluation
that is also guided by priority setting.
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Sangster, S.A., and Sutton, J.D. 1983.
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Burdock, G.A., Wagner, B.M., Smith, R.L.,
Munro, I.C., and Newberne, P.M. 1990.
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Cadby, P. 1990. Priority setting and the harmon-
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Caldwell, J. and Chidgey, M.A.J. 1985. Dose-
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Caldwell, J., Anthony, A., Cotgreave, I.A.,
Sangster, S.A., and Sutton, J.D. 1985. In-
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Caldwell, J., Sangster, S.A., and Sutton, J.D.
1985. The fate of eugenol in the rat and its
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Cramer, G.M., Ford, R.A., and Hall, R.L. 1978.
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Gerarde, H.W. 1973. Survey update: Deter-
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Vodoz, C.-A. 1975. Survey of worldwide use
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Grundschober, F. and Stofberg, J. 1986. Priority
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23-26 July 1985, ed. G. Charalambous.
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Hall, R.L. and Oser, B.L. 1961. Recent progress
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Hall, R.L. and Oser, B.L. 1965. Recent progress
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Cosmet. Toxicol. 15:457.
Oser, B.L., Weil, C.S., Woods, L.A., and
Bernard, B.K. 1985. Recent progress in the
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J., Easterday, O.D. 1988. A Codex flavour
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(88)9). Joint Council of Europe/Commission
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Chapter 22
Labeling Regulations
Klaus Bauer
The whole purpose of labeling is to inform
the user or consumer of the contents of a
given package. The aim of labeling regu-
lations is to ensure that the correct infor-
mation is made available, clearly, precisely
and in such a manner that no direct or
indirect deception as to the true nature of
the contents arises from any words, pictures
or designs used on the label. Regulations
governing labeling cover a wide range of
commodities; here we are concerned only
with those affecting foodstuffs, beverages
and other consumed products, and of flavor-
ing preparations used in their manufacture.
Article III of the IOFI recommendations
on flavoring legislation states that food to
which flavoring has been added shall be
appropriately labeled where such labeling
is necessary to prevent deception of the
consumer. It also proposes that flavorings
should be so labeled as to permit the food
manufacturer to observe the requirements
for correct label declarations imposed upon
him. The interpretation of these simple
rules is broadly similar worldwide although
national legislation may differ in detail as
applicable to flavoring materials and food-
stuffs containing flavorings. In some coun-
tries, a clear distinction is made between
"natural" and "artificial" flavorings, both
852
being declared on the label; in others, only
"artificial" flavorings need to be declared;
and in several countries, the presence of a
flavoring in the end-product does not need
declaration in the list of ingredients. A
review of labeling legislation as it applies
worldwide is given following the references
at the end of this text. It is not claimed that
this is complete, but it covers all of the
major trading nations. It must be empha-
sized that this is only intended as a guide to
the flavorist and food manufacturer. With
constantly changing regulations, it is nec-
essary to confirm the current legislative
position and requirements to ensure com-
pliance with the law. Since, in most coun-
tries, the sale of foodstuffs bearing illegal
labeling information may result in lengthy
litigation and confiscation of the goods, it
is essential that those bearing the respon-
sibility for the food product should be
completely familiar with the regulations
governing such products in the country in
which it is to be sold to the consumer or to
manufacturers for further processing.
What appears on a label depends on the
nature and end-use of the product and
whether the label has to have an eye-appeal
to the consumer. Preparations intended for
sale between manufacturers (e.g., flavoring

preparations sold to the food manufacturer
or soft drink bottler) do not generally attract
such legislative attention nor require the
same declarations as food products, etc.,
intended for sale and consumption by the
public.
LABELING FLAVORING
MATERIALS
In the case of bulk flavoring preparations as
opposed to flavorings packed and sold to the
public for domestic use, it is always nec-
essary for the label or container itself to
indicate in clear bold letters: (a) the correct
designation of the contents, including any
distinguishing product code numbers or
quality classification, (b) the net weight
or volume of the contents (in the case of
drums, the gross, tare and net weights
should be given to aid checking), (c) a dis-
tinguishing batch number by which the
contents can be directly related to a specific
manufacturing formulation, and (d) the
name and address of the manufacturer.
Additional information may be called for; if
goods are imported, it is usually necessary
to indicate the country of origin of the
contents. Frequently, end-users and carriers
who have to handle the goods may request
some or all of the following information on
the label or container: notice of any hand-
ling hazards, notice of hot or refrigerated
storage or transportation, notice of fire
risk or flammability, or any other special
instructions.
LABELING GRAS SUBSTANCES
The labeling regulations of the United
States, under 21 CFR, sec 1.12(g)(2), re-
quire that mixtures of flavoring ingredients
shipped to food processors should be fully
declared on the label. However, in place of
the full listing the following declaration
may be made as appropriate: "All flavor
ingredients contained in this product are
approved for use in a regulation of the Food
and Drug Administration" together with
Labeling Regulations 853
any nonflavor or nonapproved flavorants
which must be listed individually by com-
mon name.
FOOD PRODUCT LABELING
In most countries, the general food laws
cover not only the composition of certain
groups of food products but prescribe
regulations on labeling for both prepacked
and nonpackaged food commodities and
products on display and for sale to the
public. Although the precise format of
labels and the declarations to be made on
them differ considerably between countries,
most such regulations require foodstuffs to
be labeled to include:
a. The name of the food, giving a clear
and nondeceptive description such as
to enable the consumer to determine
the character of the product. This may
seem self-obvious, but product de-
scriptions have often been the subject
of misunderstanding, sometimes in-
tentional. With increasing consumer
demands for "all natural" products
the pressure on the food manufac-
turer and the flavor industry to pro-
vide appropriate flavorings is great.
Even the practice of adding nature-
identical synthetic chemicals to
natural essential oils means that
the pro,duct must be classified as
"imitation" in most countries.
Stanton (1976) stresses the need for
more precise definitions particularly
with respect to WONF flavorings.
Currently in the United States, the
flavor manufacturer may be called
upon to supply a certificate of authen-
ticity for entirely natural flavorants.
b. A complete list of ingredients in
descending order of their presence by
weight in the product when manu-
factured. Such a listing is intended to
give the consumer direct information
of the nature of what he or she is
consuming. This implies the use
 854 Source Book of Flavors

of specific names where these are value of the end-product does not generally
meaningful or generic terms (e.g., enter into the discussion on its sensory
antioxidants), if these are permitted, acceptance. As part of a new product devel-
which convey more information than opment team, flavor technologists should at
the use of a long chemical name. least have an understanding of the basics of
Many product groups are subject to human nutrition but the public debate on
legislation controlling their com- label declarations ranges far outside simple
position and in some countries such nutritional requirements and is outside the
products do not require a list of in- scope of this book.
gredients. Some products are speci-
fically exempted for practical reasons
References: Labeling Regulations
(e.g., bread, flour, confectionery, Andres, C. 1979. What consumers think about
servings of ice cream, etc.). ingredients on labels. Food Process. 40(12):
c. The name and address of the manu- 36, 38.
facturer, packer or importer as Anon. 1973A. Food industry briefing on food
appropriate so that product liability labeling proposals. Food Techno!. 27(4):52-
can be established in the event of any 53.
complaint. Anon. 1973B. Excerpts for the food industry
briefing on food labeling proposals-quotes.
Specific regulations may require addi- Food Techno!. 27(4):58-60, 62.
tional information or statement to be in- Anon. 1974. Nutrition labeling-a scientific
status summary. Food Techno!. 28(7):43-48.
cluded on the label. Many countries control
Anon. 1979A. First data on labeling hearings
the relative impact of pictures and drawings show ingredient percentage labeling favored
to the descriptive lettering used. Most such by consumer. Food Prod. Dev. 13(3):10.
legislation prescribes the use or prohibition Anon. 1979B. FDA's Miller doubts risk/benefit
of fruit or other foodstuff pictures, etc., if approach: sees modified food safety frame-
these are likely to deceive the consumer into work. Food Prod. Dev. 13(8):74, 76.
thinking that the product is natural when, in Babcock, M.J. 1971. A proposed scheme for
fact, it contains artificial flavorings. Some nutritive labeling. Food Techno!. 25(11):86-
countries (e.g., United Kingdom) have 87.
already adopted regulations requiring the Bauman, H. E. 1971. Nutrient labeling-purpose
date marking of perishable foodstuffs; and and approach. Food Techno!. 25(6):47-49.
Borenstein, B. 1973. Micronutrient consider-
there is considerable debate on the nature
ations in nutrient labeling. Food Techno!.
and extent of any nutritional data that 27(6):32-34.
should be provided on the label. As yet Brown, G.B. 1978. What the U.S. consumer
there is nothing like agreement on the knows, thinks and practices when it comes to
advisability or value to the consumer of such nutrition. Food Prod. Dev. 12(4):35-38.
label information. It is not uncommon for Daniels, R.W. 1974. Handbook No. 8 and
the language(s) to be used on labels to be nutrition labeling. Food Techno!. 28(1):46-
defined (e.g., Canada requires both English 47, 60.
and French). Forbes, A.L. 1978. Nutritional labeling from the
government point of view. Food Techno!.
32(12):37-38, 40-41.
Nutritional Labeling Goldblith, S.A. 1971. "Pro bono publico"-in
the best scientific tradition. Food Techno!.
This is an involved and presently a some- 25(3):32-33.
what emotive subject. The extent of the Hopper, P.F. 1974. The regulatory climate for
debate can be judged by the numerous prudent diet foods. Food Techno!. 28(1):28,
articles included in the following references. 30.
For most flavorists, participation in this Hopper, P.F. 1978. Balancing the costs and
debate is rather academic as the nutritional benefits of nutrient labeling. Food Prod. Dev.
 Labeling Regulations 855

12(9):48, 50.
Howard, H.W. 1971. Ingredient labeling: Easier
said than done. Food Techno!. 25(5):18-20.
Hutt, P.B. 1977A. Food regulations-coping
with more. Food Techno!. 31(9):82-85.
Hutt, P.B. 1977B. Balanced government regu-
lations of consumer products. Food Techno!.
31(1):58.
Johnson, O.C. 1974A. Regulations affecting
prudent diet foods. Food Techno!. 28(1):30,
32.
Johnson, O.C. 1974B. Labeling regulations.
Food Techno!. 27(3):24, 26.
Kennedy, D. 1977. Food labels and advertise-
ments are a means of educating consumers as
part of a public health mission. Food Prod.
Dev. 11(10):66.
Kinsella, J.E. 1975. Lipids and fatty acids in
foods quantitive data needed. Food Techno!.
29(2):22-23, 25-26.
Kramer, A. 1974. Storage retention of nutrients.
Food Techno!. 28(1):50-51, 53-56, 58, 60.
McCarthy, M.A. eta!. 1977. Mineral content of
legumes as related to nutritional labeling.
Food Techno!. 31(2):86, 88, 90-91.
Mermelstein, N.H. 1973. Nutrient labeling and
the independent laboratory. Food Techno!.
27(6):42-44, 46.
Middlekauf, R.D. 1975. Congressional bills
support consumer demands. Food Techno!.
28(10):66.
Oser, B.L. and Ford, R.A. 1977. Recent pro-
gress in the considerations of flavoring ingre-
dient under the Food Additives Amendment.
10. GRAS substances, Food Techno!. 31(1):
65.
Russoff, 1.1. 1978. Nutrient labeling from the
industrial point of view. Food Techno!.
32(12):32, 34, 36.
Sayer, M.D. 1975. Today's rose, by any other
name, would be misbranded. Food Prod.
Dev. 9(5):28, 30.
Schrayer, D. W. 1978. Consumer response to
nutrient labeling. Food Techno!. 32(12):42-
45.
Serritella, P.J. 1978. Dissecting a flavor prob-
lem-bulk flavor labeling. Food Prod. Dev.
12(7):43-44, 46-48.
Stanton, N.K. 1976. Flavor needs of the food
industry. Perfum. Flavorist 1(2):27-28.
Tillotson, J .E. 1977. Extending the product
labeling concept. Food Prod. Dev. 11(10):67.
Waters, A.M. 1978. Current and potential
labeling for the food industry. Int. Flavours
Food Additives 9:31.
Wodicka, V.O. 1973. FDA's omnibus labeling
proposals-an overview. Food Techno!.
27( 4):54-56.
Wyse, B.W. eta!. 1976. Nutritional quality index
(NQI) indentifies consumer nutrient needs.
Food Techno!. 29(1):22, 26-27, 32-33, 35-
37, 40.

TABLE 22-1. Worldwide Labeling Regulations

Labeling Regulations Governing
Country Flavoring Preparations Foodstuffs Containing Flavorings
ARGENTINA 1. A mixture of essential oils or their iso- No specified requirements.
lates with synthetic products, as well as
mixtures of synthetic products which
imitate natural essences shall be la-
beled: "Esencia artificial de ....," or
"Esencia artificial de fantasia."
2. Extracts prepared with synthetic prod-
ucts must be labeled: "Extracto artifi-
cial de ...."
3. Natural essences, isolates and artificial
essences in solution in a permitted sol-
vent must be labeled: "Esencia natural
de ...."or "Extracto seco de .... (solu-
cion)" or "Esencia artificial de .... (so-
lucion)."
4. Emulsions must be labeled: "Aceite es-
encial de .... (emulsion)."
5. Powdered flavorings must be labeled:
"Aceite esencial de .... (pulvo)."
6. Artificial flavorings for soft drinks sold
for domestic use must be labeled:
"Esencia artificial p,ara licor gusto" and
"Para uso familiar.'
 856 Source Book of Flavors
TABLE 22-1. Continued
Labeling Regulations Governing
Country Flavoring Preparations
AUSTHALIA 1. All states require that imitation fla-
vorings and extracts be labeled: "Imita-
tion Essence/Flavour/Extract of ...."
or "Imitation .... Essence/Flavour/Ex-
tract" as appropriate.
2. The size and type of lettering is defined State legislation exempts several classes of
in state legislation.
3. In all states it is forbidden to use any In all states a list of ingredients must be
description, designation or design on
any label of an imitation essence.
AUSTRIA No special requirements.
BELGIUM No special requirements but it is prohib- Flavorings need not be declared.
ited to give any information on the label
which is misleading with respect to na-
ture, origin or source of the material or
its proposed use.
CANADA 1. Designation appropriate to the stan-
dard given in Food & Drugs Regula-
tions, Division 10. Imitation or artificial
flavorings must be labeled "Imitation"
or "Artificial" as an integral part of the
designation.
2.
DENMARK 1. Labels must bear: (a) name and ad-
dress of manufacturer, importer or
dealer; (b) the registered trade name
(if apr,licable); (c) the words "for food"
and 'limited application"; (d) list of
additives in the preparation-flavoring
substances are declared as "Aroma" or
"Aromastof (fer)"; (e) theE numbers of
any additives; (f) percentage of each ad-
ditive (except flavorants and colors);
(g) shelf-life and batch code.
FINLAND No special requirements for flavorings but Artificial flavorings must be declared as
additive legislation requires individual
declarations of nature and quantity.
FRANCE 1. Flavorings offered for sale must be la-
beled with the correct designation of
the flavor and its proposed use. Arti-
ficial flavorings must be labeled as
"Arome artificiel (or synthetic)," or
"Composition aromatique," or "Arome
compose" with the word "artificiel" or
"synthetic." Fantasy names and code
numbers are permitted. An indication
of the use, qualitative composition and
carrier or solvent must be included; the
strength of any alcohol must be de-
clared.
Foodstuffs Containing Flavorings
In New South Wales, Victoria, S. Australia,
Queensland, Tasmania and W. Australia
products must be labeled: "Artificially
Flavoured."
foodstuffs from this requirement.
ll'iven on a product, the declaration being
m decreasing order of proportion.
Ingredients must be printed on the label in
descending order of proportion. Food ad-
ditives do not need to be included in this
ingredient list but must be declared ac-
cording to their technological effect:
"Kiinstlich aromatisiert" or "Natiirlich
aromatisiert," as appropriate; or, under
their generic name: "mit Kiinstlichem
Aroma" or "mit Natiirlichem Aroma,"
as appropriate.
Ingredients must be listed and flavorings
declared either as "flavour" if natural or
"imitation, artificial or synthetic flavour"
as appropriate. Declarations must be in
both English and French.
Where an added flavoring is not natural
and the label bears an illustration of the
natural food flavour source, the declara-
tion that the added flavoring is "imita-
tion or artificial" must be in letters of
the same size as the net quantity declara-
tion. The positioning of the declaration is
also defined.
Flavorings must be declared as ingredients
in the contents listing as: "Aroma" (for
flavors) or "Aromastof (fer)" (for flavor-
ing substances)
"artificial flavourings."
Declared on the ingredients listings as
"Arome" or "Agent d'aromatisation."
This may be 9.ualified by the addition of
"nature!" or 'artificiel" as appropriate.
In general, the label must not carry any
name, information or illustration which
will tend to mislead the consumer as to
the true nature of the product.
 Labeling Regulations 857

TABLE 22-1. Continued

Labeling Regulations Governing

Country Flavoring Preparations Foodstuffs Containing Flavorings
FRANCE 2. Artificially reinforced flavorings must
(Continued) be labeled "Arome concentres de ....
renforce artificiellement"; the degree of
concentration as "concentre x fois"
(where x is the degree of concentra-
tion); the quantity of the artificial re-
inforcing flavorinfi as "apport reforca-
teur: y pour mille where y is flavoring
in g per kg of the natural product; an
indication of proposed application; an
indication of type and percentage of
any carrier or solvent (except water and
ethanol); net weight or volume; details
of any added colorants or other addi-
tives giving the percentage if there is a
dosage limitation; and the name and
address of the manufacturer or im-
porter.
3. Pictures of fruit and flowers are not
permitted on any artificial flavoring
preparations.
GERMANY 1. All products intended for further pro- Permitted artificial flavorings must be de-
cessing must be clearly labeled in Ger- clared as "mit kiinstlichem Aromastoff';
man. those containing nature-identical syn-
thetic flavorings are marked "kiinstlich
Aromatisiert" or "mit kiinstlichem ..... .
Geschmack."
2. Flavorings must be labeled with: (a) Products containing only natural flavor-
the name of the manufacturer and ad- ings do not carry a declaration.
dress of principal location; (b) designa-
tion: "Essenz .....,"or "Aroma ....,"
or "Grundstoff ..... ," as appropriate.
Products may only be labeled "natiir-
lich" if they contain only natural mater-
ials. If the product contains permitted
solvents, diluents, preservatives, anti-
oxidants or colors it must be labeled
"mit natiirlichem Aromastoff"; flavor-
ings containing any nature-identical
synthetic flavorants must be labeled
"kunstlich" and those containing any of
the permitted artificial flavorants must
be marked "mit kiinstlichem Aroma-
staff"; (c) the contents at time of filling;
(d) an indication of application and
dosage.
3. Preparations containing any of the per-
mitted artificial flavoring substances
must carry a declaration of the quantity
present per liter or kilogram of product.
ISRAEL No special requirements. Declare as "flavours" with or without the
words "artificial" or "natural."
ITALY No special requirements but packages must Products containing natural or nature-
bear the name and address of the manu- identical flavorings must be labeled with
facturer or packer. the words "aromi naturali"; those con-
taining artificial flavorings must include
the words "aromi artificiali" in the list of
ingredients.
JAPAN Products must carry the following label Except for standardized foodstuffs flavor-
information: (a) product name, (b) date ings need not be declared.
of manufacture (or date of importation,)
(c) list of any chemical constituents other
than flavoring materials by weight pres-
ent. Information must be in Japanese of
defined size of characters.
THE NETHERLANDS No special requirements. Not necessary to declare the presence of
flavorings.
 858 Source Book of Flavors

TABLE 22-1. Continued

Labeling Regulations Governing
Country Flavoring Preparations Foodstuffs Containing Flavorings
NEW ZEALAND 1. Natural essences and extracts must be Non standardized foods must carry an
designated as specified in the regula- ingredients list~ and "flavourings"
tions. should appear in th1s.
2. If any named plant or fruit is part of Standardized food products do not gener-
the title of an artificial culinary essence, ally require an ingredients listing other
extract or flavorin~ the word "imita- than as specified in the regulations.
tion" or "artificial ' must accompany
the plant or fruit name in uniform letter
size.
NORWAY Flavorings are treated as food additives Certain s11_ecified foodstuffs must be la-
and must be labeled with the specified beled "Tilsatt kungstig smaks/aroma-
title. In mixtures the ingredients must stofr' (with addition of artificial flavor)
be declared in descending order of pro- as necessary. All other products contain-
portion. If permitted amount is limited, ing added flavorings must be declared as
the amount present must be declared by "flavours" in the ingredients list.
percentage weight. Preparations of addi-
tives must be in sealed bottles and la-
beled "Contains additives for use in
foods." The label must carry the name
and address of the manufacturer (or
packer).
PORTUGAL No special requirements. No special requirements, but food products
must carry an ingredients listing and
flavorings should be declared in this as
"Aroma."
SOUTH AFRICA Flavorings must be labeled "For use in Declared in the ingredients list as "Fla-
foodstuffs" and give a clear indication of vouring agents." Specified food product
composition. Artificial or synthetic fla- groups are exempted from this label-
voring materials must be precisely desig- ing requirement.
nated. Flavorings made from synthetic or
artificial constituents must be labeled:
"prepared from synthetic ingredients," or
"imitation," "artificial," or "synthetic" as
appropriate.
SPAIN 1. Labels must carry the following infor- No special requirements. Certain foods
mation: (a) the words "par uso alimen- must carry a list of ingredients and added
tario," (b) registered trade mark or flavorings should be listed as "aromas
name of manufacturer, (c) address of naturales" or "aromas artificiales" as ap-
manufacturer, (d) Health Registration propriate.
number, (e) net weight or volume, (f)
product designation, (g) manufacturing
identification (batch) number.
2. Products containing only natural ingre-
dients. are labeled "natural"; products
containing nature-identical synthetic
flavoring materials are labeled "aroma
al gusto de . . . . .," and those con-
taining artificial flavoring materials
must be labeled "aroma artificial."
3. The designation "natural reforzado" is
restricted to products which are pre-
dominantly natural with added flavor-
ings limited to 4 g per liter.
4. The use of misleading signs, descrip-
tions, drawings or words that might
lead to confusion with fruit juices is
prohibited.
SWEDEN Harmless flavoring preparations need on- Flavorings must be declared in the in§re-
ly be labeled with the words "essence" dients list using the words "essence or
or "flavour" as appropriate. "flavour" with an appropriate descriptive
phrase if necessary.
SWITZERLAND 1. No special requirements. Ingredient listing is not generally required.
Standards for individual food groups
specify that any artificial flavorings used
shall be declared as "a l'arome de ....."
2. Natural flavorings reinforced with not
more than 5% of harmless artificial fla-
vorants may be regarded as "natural."

TABLE 22-1. Continued
Labeling Regulations Governing
Country Flavoring Preparations
UNITED KINGDOM 1. Flavoring preparations offered for sale Label designation may not include the
as such must be labeled with (a) the
appropriate designation, (b) weight or
volume of contents, (c) name and ad-
dress of packer (or labeler) or agent in
the U.K. and the country of origin if
imported.
UNITED KINGDOM 2. Ministry of Food Code of Practice on Pictorial device may not be used to suggest
(Continued) Essences and Flavourings CP.l8 (1949)
states: Flavorings derived wholly from
naturally occurring products may be
designated "essence"; all other flavor-
ings derived wholly or partly from arti-
ficial materials shall be called "flavour,"
"flavouring," "synthetic essence," or
"artificial essence."
3.
UNITED STATES 1. Standardized flavoring preparations Flavorings must be declared on the prod-
must be labeled in accordance with the
requirements of the standard.
2. Flavoring preparations sold for use in Statements referring to a particular flavor
manufacture of foods must be labeled
(a) common or usual name, (b) if a
mixture by the common or usual names
of the constituents or "All flavor in-
gredients contained in this product are
approved for use in a regulation of the
Food and Drug Administration" or
"Flavor ingredients are listed as GRAS
in a reliable industry association list
(published)." (Note: this latter state-
ment was permissible only until July
1979).
3. Entirely natural flavoring preparations The labeling regulations specify type size
Labeling Regulations 859
Foodstuffs Containing Flavorings
name of any food or foods in such a way
as to indicate a specific flavor unless: (a)
such flavor is derived wholly or mainly
from the designated food or foods, (b) the
name of the food is immediately followed
by the word "flavour" in letters of the
same size, style and color.
directly or indirectly that a foodstuff has
imparted a specific flavor to the product
unless that flavor is wholly or mainly
from the designated food.
Additives are required to be listed in the
product ingredients list by proportion
present. Both natural and artificial fla-
vorings may be declared simply as "fla-
vouring." Where a foodstuff containing
a flavoring is used as an ingredient of
another food, provided that the flavoring
makes no effect on the final product,
then that ingredient may be declared as
" ..... with flavouring."
uct ingredients listing as follows: any
spice, natural flavor, or artificial flavor as
"spice," "natural flavor," or "artificial
flavor" as appropriate; or any combina-
tion of these declarations.
are controlled as follows: (a) If food con-
tains entirely natural flavoring to give
the characteristic flavor, the name of the
food on the principal display panel shall
be accompanied by the common name of
the characterizing flavor. The type size is
defined. (b) If the food is one which is
normally expected to contain the charac-
terizing food ingredient (e.g. strawberries
in strawberry shortcake), but most of the
characteristic flavoring is derived from a
natural source and not from the presence
of that food ingredient, then the product
may be labeled "natural ..... flavored
..... "(e.g., natural strawberry flavored
shortcake). (c) If the characteristic flavor
of the foodstuff is derived solely from
natural flavoring none of which is derived
from the product whose flavor is simu-
lated, then the product must be labeled
either with the flavor of the product
from which the characteristic flavor is
derived, or "artificially flavored." (d) If
the food contains both a natural charac-
terizing flavor that is named as part of
the product designation and other natu-
ral flavoring which simulates, resembles
or reinforces the characterizing flavor,
then the product name must be followed
by the designation "with other natural
flavor" (often abbreviated to WONF). (e)
If the food contains any artificial flavor-
ing, the name on the principal panel must
be accompanied by the words "artificial"
or "artificially flavored."
 860 Source Book of Flavors

TABLE 22-1. Continued

Labeling Regulations Governing

Country Flavoring Preparations
UNITED STATES may be designated " ..... flavor" or
(Continued) "natural ..... flavor"; where it con-
tains both natural and artificial flavor-
ings the product must be labeled "nat-
ural and artificial ..... flavor"; where
the product contains only artificial fla-
voring substances it shall be labeled
"artificial ..... flavor."
4. If the product label indicates that there
is no artificial flavor present then the
supplier must provide a certificate to
the FDA on request. The FDA is em-
powered to inspect inventories, formu-
lation and ingredients records in order
to verify any such certificate.
Foodstuffs Containing Flavorings
and layout requirements so as to avoid
misunderstanding or misrepresentation.
If a foodstuff contains three or more char-
acterizing flavors, or a blend of flavors
none of which is dominant, the product
may be described with an appropriate
generic name instead of naming each in-
gredient (e.g., "artificially flavored fruit
punch").

FLAVOR LABELING final product appear to have ingredients

UNITED STATES of higher value present than are actually
Flavor Labeling is a very important subject in the product.
when a flavor has been added to a food
product. Flavor Labeling Regulations have Flavors are usually added to processed
been developed to inform the consumer, in food products and beverages. On selected
examples highlighting the existing Flavor
a forthright manner, what can be expected
Labeling Regulations and the attendant
from a food to which flavor has been added.
In addition, Flavor Labeling Regulations portions of the Preamble, the reader can
are intended to protect the consumer and observe and appreciate the requirements of
how to label food products appropriately.
safeguard against unfair competition.
In the United States, there is more than First of all, the meaning of the Preamble
requires explanation of how it evolves and
one type of Flavor Labeling Regulation to
what impact it has on regulations. The Pre-
consider:
amble to any regulation is being published
in the Federal Register, and serves to assist
1. A flavor is sold to a food processor. The in the understanding of regulations by
label of this container must contain elaborating concepts and ideas. The Pre-
sufficient information to permit the food amble consists of a collection of comments
producer the proper use of the material. made by the public and interested groups,
2. A flavor is sold to the consumer. This to which the Commissioner has responded.
is done in small bottles, often called In the case of the Flavor Labeling Regu-
"extract." The proper labeling for this lations, the Preamble offers greater depth
category is especially important so the and appreciation of what the FDA intended
consumer handles this "concentrated when the reader studies 21 CFR Paragraph
food" in a safe manner. 101.22.
3. Flavor is being added to a food product The Preamble on the Regulation For
in which case it performs a function of Enforcement of the Federal Food, Drug and
providing pleasure through good taste. It Cosmetic Act, and the Fair Packaging and
shall be stated in a truthful manner, what Labeling Act, was published in the Federal
a food product consists of and that the Register, Volume 38, Number 231 on
addition of a flavor does not make the December 3. 1973.

The complete text of the Flavor Labeling
Regulations 21CFR, Paragraph 101.22,
leading to the publication of those re-
gulations (as published December 3,
1973) have been reprinted in this book
at the end of this chapter on Pages 871
to 875.
Instructions to the Reader
Regulations text is printed on the following
pages on the left half of the page. Portions of
the Preamble are printed on the right half of
Labeling Regulations 861
Examples follow that should help to
clarify certain issues as we now work our-
selves through the Flavor Labeling Regu-
lations. Where possible, portions from the
Preamble have been extracted to highlight,
through comparison, the meaning of the
Regulations.
the page. Preamble comments have been
provided to clarify the key issues of the
regulations.
Preamble
Title 21-Food and Drugs
CHAPTER 1-FOOD AND DRUG ADMIN-
ISTRATION, DEPARTMENT OF HEALTH,
EDUCATION AND WELFARE
SUBCHAPTER A-GENERAL
PART 1-REGULATIONS FOR THE
ENFORCEMENT OF THE FEDERAL
FOOD, DRUG, AND COSMETIC ACT AND
THE FAIR PACKAGING AND LABELING
ACT
Food Labeling, Spices, Flavorings, Colorings,
and Chemical Preservatives
In the FEDERAL REGISTER of January 19,
1973 (38 FR 2139), the Commissioner of Food
and Drugs published a proposal to revise the
requirements contained in 1.12 (21CFR 1.12)
with respect to the labeling of flavor when sold in
bulk and when contained in food. A final order
on this matter was published in the FEDERAL
REGISTER of August 2, 1973 (38 FR 20718).
A number of requests were received for recon-
sideration or modification of the August 2 order.
The Commissioner proposed further modifica-
tion of that order in the FEDERAL REGISTER
of October 5, 1973 (38 FR 27622), and permitted
four weeks for comment. Comments were
received from a number of organizations,
companies, and individuals.
The Commissioner has reviewed all of the
comments and petitions submitted with respect
to the January 19 and October 5 proposals and
the August 2 order, in promulgating the final
862 Source Book of Flavors

regulation set out below. The major points that

have been made with respect to the August 2
order and the October 5 proposal, and the
Commissioner's conclusions, are as follows:

Paragraphs 101.22(a)(l) and (a)(2) are self- useful tools in understanding those defini-
explanatory describing the terms "artificial tions. Listed examples make it easy to
flavor" and "spice" respectively. They are understand those terms.

Regulations

Subpart B-Specific Food Labeling

Requirements
101.22 Foods; labeling of spices, flavorings,
colorings and chemical preservatives.
(a)(1) The term "artificial flavor" or "artificial
flavoring" means any substance, the function of
which is to impact flavor, which is not derived
from a spice, fruit or fruit juice, edible yeast,
herb, bark, bud, root, leaf or similar plant
material, meat, fish, poultry, eggs, dairy pro-
ducts, or fermentation products thereof. Arti-
ficial flavor includes the substances listed in
172.515(b) and 182.60 of this chapter except
where these are derived from natural sources.
(2) The term "spice" means any aromatic
vegetable substance in the whole, broken, or
ground form, except for those substances which
have been traditionally regarded as foods, such
as onions, garlic and celery; whose significant
function in food is seasoning rather than nutri-
tional; that is true to name; and from which no
portion of any volatile oil or other flavoring
principle has been removed. Spices include
the spices listed in 182.10 and Part 184 of this
chapter, such as the following:
Allspice, Anise, Basil, Bay leaves, Caraway
seed, Cardamon, Celery seed, Chervil,
Cinnamon, Cloves, Coriander, Cumin seed,
Dill seed, Fennel seed, Fenugreek, Ginger,
Horseradish, Mace, Marjoram, Mustard
flour, Nutmeg, Oregano, Paprika, Parsley,
Pepper, black; Pepper, white; Pepper, red;
Rosemary, Saffron, Sage, Savory, Star
aniseed, Tarragon, Thyme, Turmeric.

Paprika, turmeric, and saffron or other spices

which are also colors, shall be declared as "spice
and coloring" unless declared by their common
or usual name.

The term "Natural Flavor" described under
Paragraph 101.22(a)(3) still stands as is. The
relevant Preamble Comment #1 has one
sentence pointing out that products ob-
tained by roasting, heating, and enzymolysis
Regulations
101.22(a)(3) The term "natural flavor" or
"natural flavoring" means the essential oil,
oleoresin, essence or extractive, protein hydro-
lysate, distillate, or any product of roasting,
heating or enzymolysis, which contains the
flavoring constituents derived from a spice, fruit
or fruit juice, vegetable or vegetable juice, edible
yeast, herb, bark, bud, root, leaf or similar plant
material, meat, seafood, poultry, eggs, dairy
products, or fermentation products thereof,
whose significant function in food is flavoring
rather than nutritional. Natural flavors include
the natural essence or extractives obtained from
plants listed in 182.10, 182.20, 182.30, 182.40,
and 182.50 and Part 184 of this chapter, and the
substances listed in 172.510 of this chapter.
As we continue to work our way through the
regulations, the subject actually begins at
Regulations 101.22(i)
(i) If the label, labeling, or advertising of a food
makes any direct or indirect representations with
respect to the primary recognizable flavor(s) by
word, vignette, e.g., depiction of a fruit, or other
means, or if for any other reason the manu-
facturer or distributor of a food wishes to de-
signate the type of flavor in the food other than
through the statement of ingredients, such flavor
shall be considered the characterizing flavor and
shall be declared in the following way:
Labeling Regulations 863
have traditionally been regarded as "natural
flavor," and that the Commissioner concurs
with this comment. The issue of "natural"
has generated much activity over the years
without coming to a satisfactory conclusion.
Preamble Comment# 1
1. Several comments, concurring with the
proposal to delete the broad category of "reac-
tion products" from the definition of natural
flavor in 1.12(a)(3), stated that the definition
should further be revised to permit products
obtained by roasting, heating, or enzymolysis.
It was pointed out that such products have tradi-
tionally been regarded as natural flavors.
The Commissioner concurs in this comment and
the definition has been so revised.
Paragraph 101.22(i) where it states: "If the
label, labeling or advertising ...
Preamble Comments #7 and #8
7. Numerous comments indicated widespread
failure to understand the relatively limited
circumstances under which 1.12(i) will apply.
Several comments reflected the erroneous inter-
pretation that all food must be so labeled with
respect to its flavor content.
The Commissioner advises that, if a food makes
no direct or indirect representations with respect
to flavor, the provisions of 1.12(i) are inappli-
cable. In such circumstances, the presence
of artificial or natural flavor, or both, may be
declared simply in the statement of ingredients,
as permitted by sections 403(i) and (k) of the act.
8. One comment requested clarification of the
circumstances under which a food name would
make representations with respect to flavor.
The Commissioner concludes that it is not
possible to set out all circumstances under which
a flavor representation is or is not implied. Any
864 Source Book of Flavors
Preamble comments number 7 and 8 are
very important for the interpretation; they
spell out the limited application envisioned
IJy the Commissioner since no flavor rep-
resentation on the front panel would obviate
further flavor labeling considerations for
this portion of the label. The actual stating
that root beer, ginger ale, and cola is not a
flavor representation (Preamble Comment
#8) are helpful examples of what is meant
by this paragraph 101.22(i).
In Preamble Comment #17 the charac-
terizing aspect of the flavor has been ex-
plained and clarified.
This discussion refers to both para-
Regulations 101.22(i)(l) and 101.22(i)(l)(i)
(1) If the food contains no artificial flavor which
simulates, resembles or reinforces the charac-
terizing flavor, the name of the food on the
principal display panel or panels of the label shall
be accompanied by the common or usual name of
the characterizing flavor, e.g., "vanilla", in
letters no less than one-half the height of the
letters used in the name of the food, except that:
(i) If the food is one that is commonly expected
to contain a characterizing food ingredient, e.g.,
strawberries in "strawberry shortcake", and the
food contains natural flavor derived from such
ingredient and an amount of characterizing
ingredient insufficient to independently charac-
terize the food, or the food contains no such
ingredient, the name of the characterizing flavor
may be immediately preceded by the word
"natural" and shall be immediately followed by
the word "flavored" in letters not less than one-
use of a vignette showing a fruit or vegetable
clearly constitutes such a representation. De-
signation of a soft drink as a "cola" beverage or
ginger ale or root beer, or with well-recognized
proprietary brand names, does not constitute a
flavor representation. On the other hand, use of
a specific fruit flavor in the food name, such as
"orange soda" does constitute such a represen-
tation and requires compliance with 1.12(i).
The Commissioner will provide advisory opin-
ions with respect to specific terminology upon
request.
graphs of the regulations 101.22(i)(1) and
101.22(i)(1)(i) and gives an excellent
selection of examples of what the Com-
missioner considers characterizing and
non-characterizing.
Another interesting passage of Preamble
Comment #17 reads: "At the same time,
this test does not include all artificial flavors,
e.g., artificial flavor that merely modifies,
rounds out, or gives a particular cast to
an existing flavor without reinforcing or
increasing it or otherwise making it appear
that more is present than is actually in the
product."
Preamble Comment#17
17. Questions have arisen as to how the "charac-
terizing flavor" is to be determined, and as to
how it will be determined whether added flavor
"simulates" a characterizing natural flavor or
otherwise characterizes the product.
The Commissioner advises that the character-
izing flavor is that which is represented in
labeling or advertising as the product flavor, or
that which is in any event the primary recogniz-
able flavor of the finished food. In determining
whether added flavor does or does not simulate,
resemble, or reinforce the characterizing flavor,
the principal test will be to separate such added
flavor from the product to determine whether it
tastes like the characterizing natural flavor or
approximates the flavor characteristics of any
principal or key flavor note. Thus, the vanillin
added to a chocolate pudding would clearly not
be a characterizing flavor because it does not
 Labeling Regulations 865

half the height of the letters in the name of the
characterizing flavor, e.g., "natural strawberry
flavored shortcake," or "strawberry flavored
shortcake". (See Figure 22-1)
FIGURE 22-1. Natural flavor added to food with
sufficient characterizing ingredients (above) is labeled
"Cherry Pie"; natural flavor added to food with in-
sufficient characterizing ingredients (below) is labeled
"Natural Cherry-Flavored Pie."
taste like chocolate, whereas the benzaldehyde
added to a cherry juice would be an artificial
flavor because it does reinforce and extend the
cherry taste. It must be emphasized that the test
is not solely whether an artificial flavor simulates
or is chemically identical to the characterizing
natural flavor, but also more broadly whether it
resembles, reinforces, or extends it. At the same
time, this test does not include all artificial flavor,
such as artificial flavor that merely modifies,
rounds out, or gives a particular cast to an
existing flavor without reinforcing or increasing
it or otherwise making it appear that more is
present than is actually in the product. Thus,
benzaldehyde is a characterizing flavor in cherry
but not in cinnamon; allyl hexanoate is a charac-
terizing flavor in pineapple but not in orange; and
ethyl valerate is characterizing in apple but not in
raspberry. In the vast majority of instances, the
conclusion will be clearcut and readily accepted
by flavor technologists. The Commissioner
believes that it would be feasible and appropriate
to prepare a list of individual flavors or com-
binations showing the circumstances under which
they are characterizing for particular flavor uses.
The Commissioner recognizes that this will in
some instances involve judgmental factors, but
believes that this requirement is as enforceable as
any that could be adopted.

Preamble Comment #18 must be con- 1. "Where the characterizing flavor is

sidered the most important explanation of solely natural and is derived from the
the Flavor Labeling categories. Comment product whose flavor is simulated, the
#18 in the Preamble addresses the con- food will be labeled only with the name
fusion incurred by industry and consumer of the flavor (e.g., 'Lemon Pudding')."
alike with which the Commissioner agrees.
The categories were then reduced to five, This statement applies to Paragraph
and they are well described, in fact, much 101.22(i)(l) and provides as example
better than in the regulations themselves. "Lemon Pudding." (See Figure 22-2)
These five categories deal with all applicable
flavor regulations in the United States.
Preamble Comment #18 also explains in
more detail the difference of a flavor derived
from a food ingredient, such as strawberries
in Strawberry Shortcake, Comment 18(3),
which must be considered as "Food Label-
!
NaN~IFlavor
Umom j
ing" and a flavor added to food, such as
lemon flavor to pudding, Comment 18(1),
._
to be considered "Flavor Labeling." This FIGURE 22-2. Natural characterizing lemon flavor
distinction is very important! added to pudding is labeled "Lemon Pudding."
866 Source Book of Flavors

Preamble Comment #18

18. A large number of comments stated that all

of 1.12(i) as proposed in the October 5 notice is
confusing both to industry and to consumers,
in that there are too many categories of flavor
labeling.
The Commissioner concurs with this comment.
For that primary reason, the number of total
categories of flavor labeling in the final regula-
tions has been reduced to five. For the vast
majority of foods, which contain added flavor but
no characterizing food ingredient, there will be
only the following three labeling categories:
1. Where the characterizing flavor is solely
natural and is derived from the product whose
flavor is simulated, the food will be labeled
only with the name of the flavor (e.g., "lemon
pudding").
2. Where the characterizing flavor is solely
natural and is derived partly from the product
whose flavor is simulated and partly from other
natural sources, the food will be so labeled (e.g.,
"lemon pudding, with other natural flavor").
3. Where (a) the characterizing flavor is solely
natural and is derived solely from sources other
than the product whose flavor is simulated, or (b)
any part of the characterizing flavor is artificial,
the food will be labeled "artificially flavored"
(e.g., "lemon pudding, artificially flavored").
For those foods which the consumer expects to
contain characterizing food ingredient (e.g.,
strawberries in strawberry shortcake or peaches
in peach pie), two additional labeling categories
will exist:
Where the food does not contain a sufficient
amount of that food ingredient independently
to characterize the food and it contains added
natural characterizing flavor, it shall be labeled as
a naturally flavored food (e.g., either "natural
peach flavored pie" or as "natural peach flavored
pie, with other natural flavors", depending upon
whether all or only part of the characterizing
flavor is derived from the product whose flavor is
simulated. (The initial use of the word "natural"
is optional.)
These are the only five labeling patterns that will
be required to be used on the principal display
panel under the final regulation. All other
designations of flavors contained in the October 5
 Labeling Regulations 867

proposal will appear in the statement of ingre-

dients. Thus, the final regulation vastly simplifies
labeling while at the same time informing con-
sumers of the essential nature of the character-
izing flavoring used.

The art and science to develop and use
flavors to benefit the consumer in good and
typical taste renditions in food products at
reasonable costs, draws from many different
natural sources. By way of example, the
single most important component respon-
sible for the lemon taste is Citral. If derived
solely from Lemon Oil where Citral can be
found at a low percentage (approximately
4%), its cost would be staggering (more
than $200 per pound, at today's prices).
Citral can be obtained from natural sources
such as Lemongrass Oil or Litsea Cubeba;
its cost presently is approximately $8.00 per
pound. Many other natural ingredients not
derived from the characterizing source of
the actual flavor-giving ingredient represent
a tremendous, cost-effective tool to develop
vibrant, recognizable flavors and convey to
the consumer that they are derived from a
natural source.
The law requires that this fact be stated
clearly on the label.
2. "Where the characterizing flavor is
solely natural and is derived partly from
the product whose flavor is simulated
and partly from other natural sources,
the food will be so labeled (e.g., 'Lemon
Pudding, With Other Natural Flavor')."
This statement applies to 101.22(i)(l)(iii).

Regulations 101.22(i)(l)(iii)

If the food contains both a characterizing flavor

from the product whose flavor is simulated and
other natural flavor which simulates, resembles
or reinforces the characterizing flavor, the food
shall be labeled in accordance with the intro-
ductory text and paragraph (i)(l)(i) of this sec-
tion and the name of the food shall be imme-
diately followed by the words "with other natural
flavor" in letters not less than one-half the height
of the letters used in the name of the charac-
terizing flavor. (See Figure 22-3)

lNatural Lemonj
Flavor
With Other
Natural Flavor

FIGURE 22-3. Natural lemon flavor with other

natural flavor added to pudding is labeled "Lemon
Pudding with other Natural Flavor."
868 Source Book of Flavors

The Flavor Extracts Manufacturers' As- vised to provide this information to its
sociation (FEMA) in 1986, examined the customers, and the food producer must
labeling practices of the food industry and place the WONF phrase right onto the
how the flavor industry could help to clarify principle display panel. It is the law.
this issue. After all, the bulk flavor regula-
3. "Where (a) the characterizing flavor is
tions of Paragraph 101.22(g) could mislead
solely natural and is derived from the
a food manufacturer and cause him to
sources other than the product whose
wrongly label his product. FEMA con-
flavor is simulated, or (b) any part of the
cluded that any natural component added to
characterizing flavor is artificial, the food
a flavor, even if it would not simulate or
will be labeled 'Artificially Flavored'
resemble, would at least reinforce a flavor
(e.g., 'Lemon Pudding, Artificially
impression. The governing phrase of the
Flavored')."
Paragraph (i)(l)(iii), is: " ... and the
name shall be immediately followed by Statement (a) applies to 101.22(i)(l)(ii) and
'WONF.'" (b) to 101.22(i)(2).
The Flavor Industry, therefore, was ad-

Regulations 101.22(i)(l)(ii) and 101.22(i)(2)

(ii) If none of the natural flavor used in the food

is derived from the product whose flavor is
simulated, the food in which the flavor is used
shall be labeled either with the flavor of the
product from which the flavor is derived or as
"artificially flavored".
(2) If the food contains any artificial flavor which
simulates, resembles or reinforces the character-
izing flavor, the name of the food on the principal
display panel or panels of the label shall be
accompanied by the common or usual name(s) of
the characterizing flavor, in letters not less than
one-half the height of the letters used in the name
of the food and the name of the characterizing
flavor shall be accompanied by the word(s)
"artificial" or "artificially flavored", in letters not
less than one-half the height of the letters in the
name of the characterizing flavor, e.g., "artificial
vanilla", "artificially flavored strawberry", or
"grape artificially flavored".

Paragraph 101.22(i)(l)(ii) could cause

confusion, since it might happen that a
natural flavor of which no portion is derived
from the name source requires "Artificial" Nm~md
I Lemon
Artificial 1
on the principle display panel, but indicates Flavor

"Natural" on the ingredient statement.

Still, both 101.22(i)(l)(ii) and 101.22(i)(2) ~

probably are the easiest portions of the

FIGURE 22-4. Natural and artificial lemon flavor
labeling regulations to understand. (See added to pudding is labeled "Lemon Pudding, Artifically
Figure 22-4) Flavored."

4. "For those foods which the consumer
expects to contain characterizing food
ingredients (e.g., Strawberries in Straw-
berry Shortcake, or Peaches in Peach
Pie), two additional labeling categories
will exist:
Where the food does not contain a
sufficient amount of that food ingredient
independently to characterize the food
and it contains added natural charac-
terizing flavor, it shall be labeled as a
naturally flavored food (e. g., either
'Natural Peach Flavored Pie' or ... )."
This portion applies where food is part of
the flavor source, stating in Paragraph
101.22(i)(1)(i) that a totally derived natural
flavor added will be so labeled on the
principal display panel. The regulations, in
addition, state that if the food product
supplies the total flavor impression to be
independently characterizing, no flavor
reference is required on the principal
display panel.
The paragraph of Preamble Comment
#18 finally makes reference to the fifth
category, the WONF portion as it compares
to the flavor-giving food source and requires
as already indicated in Preamble Comment
#18(2) the appropriate statement, namely
" ... as 'Natural Peach Flavored Pie, With
Labeling Regulations 869
{Nalural)
Ch•rry flgvored Pi•
WilhOtt1er
Natural Flavor
FIGURE 22-5. Natural flavor with other natural
flavor added to food, even with sufficient characteriz-
ing ingredients is labeled "(Natural) Cherry Flavored
Pie with other Natural Flavor."
Other Natural Flavor', depending on
whether all or only part of the character-
izing flavor is derived from the product
whose flavor is simulated. The initial use of
the word 'Natural' is optional." (See Figure
22-5)
An "Auxiliary Statement" could serve to
satisfy the regulations; the concept has been
well-defined in Comments #22 and #23.
Comment #22 takes issue with a blend of
citrus oils in an orange beverage, which
would also permit the statement "derived
from natural citrus oils" and Comment #23,
that a natural flavor of which none is derived
from the name-giving source indeed could
be labeled truthfully with the Auxiliary
Statement "like" or "type" such as "Beef-
like Flavor."
Preamble Comment #22
22. One comment objected to proposed
1.12(i)(l)(iii) on the ground that citrus oils have
been used to make "orange" beverages for over
50 years and should be allowed to continue.
The Commissioner has no objection to this use of
citrus oils, but believes that, if they simulate,
resemble, or reinforce a characterizing flavor,
and the food contains no natural orange flavor,
the consumer is entitled to understand that the
product is made solely with flavor other than that
from oranges. If natural orange flavor is used in
conjunction with other natural citrus oils that
simulate, resemble, or reinforce it, the product is
properly labeled "with other natural flavor."
Under these circumstances, auxiliary statements
explaining that the flavor is derived from natural
870 Source Book of Flavors

citrus oils are permissible and sufficient fully to

inform the consumer.
23. A comment objected to proposed
1.12(i)(l)(iii) on the ground that it is misleading
to label a natural flavor as "artificial" when it is
used to simulate another natural flavor. It was
suggested that a phrase such as "beef-like flavor"
be permitted.
As already noted, the consumer is entitled to
terminology which clearly distinguishes between
the use of a natural flavor derived from the type
of product involved, and natural flavor derived
from other sources. As has already been pointed
out, truthful auxiliary statements may be utilized
by the manufacturer to explain such other natural
flavors.

The final point on the Flavor Labeling characterizing flavors blended in a food
Regulations deserving discussion is Para- product can be labeled as "Punch Blend" or
graph (i)(3)(iii), elucidated in the Comment a similar name.
#34 of the Preamble, that three or more

Regulations 101.22(i)(3)(iii) Preamble Comment #34

If the finished product contains three or more
distinguishable characterizing flavors , or a blend
of flavors with no primary recognizable flavor,
the flavor may be declared by an appropriately
descriptive generic term in lieu of naming each
flavor , e.g. , " artificially flavored fruit punch".
(See Figure 22-6)
Natural
Cherry, Orange, Grape
Flavor
One comment suggested that the regulation
should permit the use of such a generic term as
"fruit-" where three or more characterizing
flavors are used, so that it is unnecessary to spell
out each separate flavor.
The Commissioner concurs with this comment,
and the regulation has been revised accordingly.
In situations where such a collective term is used,
the same rules will apply with respect to decla-
ration of natural and artificial flavor as where the
common or usual name of each flavor is used.

l Narunl
PuM"h na\·or ~ fruit._.
runcu

FIGURE 22-6. A blend of three or more distinguish-

able characterizing fruit flavors is labeled "Fruit
Punch."

Summary Schematic of Flavor Labeling Regulations

The United States Flavor Labeling Re- which should enable the reader to quickly
gulations have been summarized in the reference the labeling requirements to the
flow diagram "Decision Pathway" appropriate paragraph. (See Figure 22-7)

Decl""' Flavor in NO
ingredient s-rnent only. 1.-~---~
101.22(i}(1}
Natural Flavor from Primary,
Flavor added or not.
Label: "AI"
101.22(i}(1}
WothWONF
Label: "AI WONF"
101.22P}(I}(iiij
With reinforcing ArtifiCial FlavOJ" or Ex-Other
artificial Flawr?
Label: "Artificially Flavored AI" Label: "Artif"ocially Flavored AI"
101.22(i}(2}
FIGURE 22-7. Flavor labeling decision pathway.
Specific Food Labeling Requirements
§ 101.22 Foods; labeling of spices, flavor-
ings, colorings and chemical preservatives.
(a)(1) The term "artificial flavor" or
"artificial flavoring" means any substance,
the function of which is to impart flavor,
which is not derived from a spice, fruit or
fruit juice, vegetable or vegetable juice,
edible yeast, herb, bark, bud, root, leaf or
similar plant material, meat, fish, poultry,
eggs, dairy products, or fermentation
products thereof. Artificial flavor includes
the substances listed in §§ 172.515(b) and
182.60 of this chapter except where these
are derived from natural sources.
(2) The term "spice" means any
aromatic vegetable substance in whole,
broken, or ground form, except for those
substances which have been traditionally
regarded as foods, such as onions, garlic and
celery; whose significant function in food is
Labeling Regulations 871
Flavor Labeling
21CFR Paragraph 101.22(i)
Decision Pathway
YES
Artificial or Ex-Oihor
Nalural Sour<e
Label: "Artificially Fl-..! AI"
101.22(ij(l}(ii}
Added c"-terizing
noturol f1ovor
Label: •A Fl-..! B"
101.22(i}(l}(i}
AddedWONF
Natural Source Label: "A Flavored I WONF"
101.22(i}(l}(iii}
101.22(i}(2}
seasoning rather than nutritional; that is
true to name; and from which no portion of
any volatile oil or other flavoring principle
has been removed. Spices include the spices
listed in § 182.10 and Part 184 of this
chapter, such as the following:
Allspice, Anise, Basil, Bay leaves, Caraway
seed, Cardamon, Celery seed, Chervil,
Cinnamon, Cloves, Coriander, Cumin
seed, Dill seed, Fennel seed, Fenugreek,
Ginger, Horseradish, Mace, Marjoram,
Mustard flour, Nutmeg, Oregano,
Paprika, Parsley, Pepper, black; Pepper,
white; Pepper, red; Rosemary, Saffron,
Sage, Savory, Star aniseed, Tarragon,
Thyme, Turmeric.
Paprika, turmeric, and saffron or other
spices which are also colors, shall be
declared as "spice and coloring" unless
declared by their common or usual name.
872 Source Book of Flavors
(3) The term "natural flavor" or "natural
flavoring" means the essential oil, oleoresin,
essence or extractive, protein hydrolysate,
distillate, or any product of roasting, heat-
ing or enzymolysis, which contains the
flavoring constituents derived from a spice,
fruit or fruit juice, vegetable or vegetable
juice, edible yeast, herb, bark, bud, root,
leaf or similar plant material, meat, sea-
food, poultry, eggs, dairy products, or
fermentation products thereof, whose
significant function in food is flavoring
rather than nutritional. Natural flavors
include the natural essence or extractives
obtained from plants listed in §§ 182.10,
182.20, 182.30, 182.40, and 182.50 and Part
184 of this chapter, and the substances listed
in § 172.510 of this chapter.
(4) The term "artificial color" or "arti-
ficial coloring" means any "color additive"
as defined in § 70.3(f) of this chapter.
(5) The term "chemical preservative"
means any chemical that, when added to
food, tends to prevent or retard deteriora-
tion thereof, but does not include common
salt, sugars, vinegars, spices, or oils ex-
tracted from spices, substances added to
food by direct exposure thereof to wood
smoke, or chemicals applied for their in-
secticidal or herbicidal properties.
(b) A food which is subject to the re-
quirements of section 403(k) of the act shall
bear labeling, even though such food is not
in package form.
(c) A statement of artificial flavoring,
artificial coloring, or chemical preservative
shall be placed on the food or on its con-
tainer or wrapper, or on any two or all three
of these, as may be necessary to render such
statement likely to be read by the ordinary
person under customary conditions of
purchase and use of such food. The specific
artificial color used in a food shall be iden-
tified on the labeling when so required by
regulation in Part 74 of this chapter to
assure safe conditions of use for the color
additive.
(d) A food shall be exempt from com-
pliance with the requirements of section
403(k) of the act if it is not in package form
and the units thereof are so small that a
statement of artificial flavoring, artificial
coloring, or chemical preservative, as the
case may be, cannot be placed on such units
with such conspicuousness as to render it
likely to be read by the ordinary individual
under customary conditions of purchase and
use.
(e) A food shall be exempt while held for
sale from the requirements of section 403(k)
of the act (requiring label statement of any
artificial flavoring, artificial coloring, or
chemical preservatives) if said food, having
been received in bulk containers at a retail
establishment, is displayed to the purchaser
with either (1) the labeling of the bulk
container plainly in view or (2) a counter
card, sign, or other appropriate device
bearing prominently and conspicuously the
information required to be stated on the
label pursuant to section 403(k).
(f) A fruit or vegetable shall be exempt
from compliance with the requirements of
section 403(k) of the act with respect to a
chemical preservative applied to the fruit or
vegetable as a pesticide chemical prior to
harvest.
(g) A flavor shall be labeled in the fol-
lowing way when shipped to a food manu-
facturer or processor (but not a consumer)
for use in the manufacture of a fabricated
food, unless it is a flavor for which a stan-
dard of identity has been promulgated, in
which case it shall be labeled as provided in
the standard:
(1) If the flavor consists of one ingre-
dient, it shall be declared by its common or
usual name.
(2) If the flavor consists of two or more
ingredients, the label either may declare
each ingredient by its common or usual
name or may state "All flavor ingredients
contained in this product are approved for
use in a regulation of the Food and Drug
Administration." Any flavor ingredient not
contained in one of these regulations, and
any nonflavor ingredient, shall be separately
listed on the label.

(3) In cases where the flavor contains a
solely natural flavor(s), the flavor shall be so
labeled, e.g., "strawberry flavor", "banana
flavor", or "natural strawberry flavor". In
cases where the flavor contains both a
natural flavor and an artificial flavor, the
flavor shall be so labeled, e.g., "natural and
artificial strawberry flavor". In cases where
the flavor contains a solely artificial flavor( s),
the flavor shall be so labeled, e.g., "artificial
strawberry flavor".
(h) The label of a food to which flavor is
added shall declare the flavor in the state-
ment of ingredients in the following way:
( 1) Spice, natural flavor, and artificial
flavor may be declared as "spice", "natural
flavor", or "artificial flavor", or any com-
bination thereof, as the case may be.
(2) An incidental additive in a food,
originating in a spice or flavor used in the
manufacture of the food, need not be
declared in the statement of ingredients if it
meets the requirements of§ 101.100(a)(3).
(3) Substances obtained by cutting,
grinding, drying, pulping, or similar pro-
cessing of tissues derived from fruit, vege-
table, meat, fish, or poultry, e.g., powdered
or granulated onions, garlic powder, and
celery powder, are commonly understood
by consumers to be food rather than flavor
and shall be declared by their common or
usual name.
(4) Any salt (sodium chloride) used as an
ingredient in food shall be declared by its
common or usual name "salt."
(5) Any monosodium glutamate used as
an ingredient in food shall be declared by
its common or usual name "monosodium
glutamate."
(6) Any pyroligneous acid or other arti-
ficial smoked flavors used as an ingredient in
a food may be declared as artificial flavor or
artificial smoke flavor. No representation
may be made, either directly or implied,
that a food flavored with pyroligneous acid
or other artificial smoke flavor has been
smoked or has a true smoked flavor, or that
a seasoning sauce or similar product con-
taining pyroligneous acid or other artificial
Labeling Regulations 873
smoke flavor and used to season or flavor
other foods will result in a smoked product
or one having a true smoke flavor.
(i) If the label, labeling, or advertising of
a food makes any direct or indirect repre-
sentations with respect to the primary
recognizable flavor(s), by word, vignette,
e.g., depiction of a fruit, or other means, or
if for any other reason the manufacturer or
distributor of a food wishes to designate the
type of flavor in the food other than through
the statement of ingredients, such flavor
shall be considered the characterizing flavor
and shall be declared in the following way:
( 1) If the food contains no artificial flavor
which simulates, resembles or reinforces the
characterizing flavor, the name of the food
on the principal display panel or panels
of the label shall be accompanied by the
common or usual name of the characterizing
flavor, e.g., "vanilla", in letters not less
than one-half the height of the letters used
in the name of the food, except that:
(i) If the food is one that is commonly
expected to contain a characterizing food
ingredient, e.g., strawberries in "strawberry
shortcake", and the food contains natural
flavor derived from such ingredient and an
amount of characterizing ingredient insuf-
ficient to independently characterize the
food, or the food contains no such ingre-
dient, the name of the characterizing flavor
may be immediately preceded by the word
"natural" and shall be immediately followed
by the word "flavored" in letters not less
than one-half the height of the letters in the
name of the characterizing flavor, e.g.,
"natural strawberry flavored short-cake," or
"strawberry flavored short-cake".
(ii) If none of the natural flavor used in
the food is derived from the product whose
flavor is simulated, the food in which the
flavor is used shall be labeled either with the
flavor of the product from which the flavor is
derived or as "artificially flavored."
(iii) If the food contains both a charac-
terizing flavor from the product whose
flavor is simulated and other natural flavor
which simulates, resembles or reinforces the
874 Source Book of Flavors
characterizing flavor, the food shall be
labeled in accordance with the introductory
text and paragraph (i)(1)(i) of this section
and the name of the food shall be imme-
diately followed by the words "with other
natural flavor" in letters not less than one-
half the height of the letters used in the
name of the characterizing flavor.
(2) If the food contains any artificial
flavor which simulates, resembles or rein-
forces the characterizing flavor, the name of
the food on the principal display panel or
panels of the label shall be accompanied
by the common or usual name(s) of the
characterizing flavor, in letters not less than
one-half the height of the letters used in
the name of the food and the name of the
characterizing flavor shall be accompanied
by the word(s) "artificial" or "artificially
flavored", in letters not less than one-half
the height of the letters in the name of
the characterizing flavor, e.g., "artificial
vanilla", "artificially flavored strawberry",
or "grape artificially flavored".
(3) Wherever the name of the charac-
terizing flavor appears on the label (other
than in the statement of ingredients) so
conspicuously as to be easily seen under
customary conditions of purchase, the
words prescribed by this paragraph shall
immediately and conspicuously precede or
follow such name, without any intervening
written, printed, or graphic matter, except:
(i) Where the characterizing flavor and a
trademark or brand are presented together,
other written, printed, or graphic matter
that is a part of or is associated with the
trademark or brand may intervene if the
required words are in such relationship with
the trademark or brand as to be clearly
related to the characterizing flavor; and
(ii) If the finished product contains more
than one flavor subject to the requirements
of this paragraph, the statements required
by this paragraph need appear only once in
each statement of characterizing flavors
present in such food, e.g., "artificially
flavored vanilla and strawberry".
(iii) If the finished product contains three
or more distinguishable characterizing
flavors, or a blend of flavors with no primary
recognizable flavor, the flavor may be
declared by an appropriately descriptive
generic term in lieu of naming each flavor,
e.g., "artificially flavored fruit punch".
(4) A flavor supplier shall certify, in
writing, that any flavor he supplies which is
designated as containing no artificial flavor
does not, to the best of his knowledge and
belief, contain any artificial flavor, and that
he has added no artificial flavor to it. The
requirement for such certification may be
satisfied by a guarantee under section
303(c)(2) of the act which contains such a
specific statement. A flavor used shall be
required to make such a written certification
only where he adds to or combines another
flavor with a flavor which has been certified
by a flavor supplier as containing no arti-
ficial flavor, but otherwise such user may
rely upon the supplier's certification and
need make no separate certification. All
such certifications shall be retained by the
certifying party throughout the period
in which the flavor is supplied and for a
minimum of three years thereafter, and
shall be subject to the following conditions:
(i) The certifying party shall make such
certifications available upon request at all
reasonable hours to any duly authorized
office or employee of the Food and Drug
Administration or any other employee
acting on behalf of the Secretary of Health
and Human Services. Such certifications are
regarded by the Food and Drug Admin-
istration as reports to the government and as
guarantees or other undertakings within the
meaning of section 301(h) of the act and
subject the certifying party to the penalties
for making any false report to the govern-
ment under 18 U.S.C. 1001 and any false
guarantee or undertaking under section
303(a) of the act. The defenses provided
under section 303(c)(2) of the act shall be
applicable to the certifications provided for
in this section.
(ii) Wherever possible, the Food and
Drug Administration shall verify the accu-

racy of a reasonable number of certifications
made pursuant to this section, constituting a
representative sample of such certifications,
and shall not request all such certifications.
(iii) Where no person authorized to
provide such information is reasonably
available at the time of inspection, the certi-
fying party shall arrange to have such person
and the relevant materials and records ready
for verification as soon as practicable:
Provided, That, whenever the Food and
Drug Administration has reason to believe
that the supplier or user may utilize this
period to alter inventories or records, such
additional time shall not be permitted.
Where such additional time is provided, the
Food and Drug Administration may require
the certifying party to certify that relevant
inventories have not been materially dis-
turbed and relevant records have not been
altered or concealed during such period.
(iv) The certifying party shall provide, to
an officer or representative duly designated
by the Secretary, such qualitative statement
of the composition of the flavor or product
covered by the certification as may be
reasonably expected to enable the Secre-
tary's representatives to determine which
relevant raw and finished materials and
flavor ingredient records are reasonably
necessary to verify the certifications. The
examination conducted by the Secretary's
representative shall be limited to inspection
and review of inventories and ingredient
records for those certifications which are to
be verified.
(v) Review of flavor ingredient records
shall be limited to the qualitative formula
and shall not include the quantitative for-
mula. The person verifying the certifications
may make only such notes as are necessary
to enable him to verify such certification.
Only such notes or such flavor ingredient
records as are necessary to verify such cer-
tification or to show a potential or actual
violation may be removed or transmitted
from the certifying party's place of business:
Provided, that, where such removal or
transmittal is necessary for such purposes
Labeling Regulations 875
the relevant records and notes shall be
retained as separate documents in Food and
Drug Administration files, shall not be
copied in other reports, and shall not be
disclosed publicly other than in a judicial
proceeding brought pursuant to the act or
18 u.s.c. 1001.
(j) A food to which a chemical preser-
vative(s) is added shall, except when exempt
pursuant to § 101.100 bear a label declara-
tion stating both the common or usual name
of the ingredient( s) and a separate descrip-
tion of its function, e.g., "preservative", "to
retard spoilage", "a mold inhibitor", "to
help protect flavor" or "to promote color
retention".
(Sees. 402, 403, 409, 701(a), 702, 703, 704,
52 Stat. 1046, 1047, 1048-1049 as amended,
1055, 1056-1057 as amended; 21 U.S.C.
342, 343, 348, 371(a), 372, 373, 374)
[42 FR 14308, Mar. 15, 1977, as amended at
44 FR 3963, Jan. 19, 1979; 44 FR 37220,
June 26, 1979]
EFFECTIVE DATE NOTE: Paragraph (c) of§
101.22 was revised at 44 FR 37220, June 26,
1979, effective date for compliance July 1,
1981. At 46 FR 31004, June 12, 1981, the
compliance date was extended to July 1,
1982. Paragraph (c) published at 42 FR
14308, Mar. 15, 1977, and set forth below is
currently effective:
§101.22 Foods; labeling of spices, flavor-
ings, colorings and chemical preservatives.
* * * * *
(c) A statement of artificial flavoring,
artificial coloring, or chemical preservative
shall be placed on the food, or on its con-
tainer or wrapper, or on any two or all of
these, as may be necessary to render such
statement likely to be read by the ordinary
individual under customary conditions of
purchase and use of such food.
Chapter 23
International Flavor
Legislation
Klaus Bauer
The use of flavoring ingredients is a long-
standing practice both domestically and in
the commercial processing of foods, bever-
ages, confectionery, etc. Historically, most
flavorings are of natural origin (e.g., herbs
and spices, fruits, etc.) but, as the tech-
nological demands of mass production,
national and international distribution, and
convenience had to be met, many of these
are now replaced by flavorings which
simulate their natural counterpart. Because
of long usage, it is frequently assumed that
natural flavoring materials are without
hazard to the consumer; but, in fact, long
usage may well induce subtle chronic toxic
effects which pass unnoticed in an ever-
changing diet. Modern research into the
biochemistry of natural flavoring materials
is high-lighting their chemical complexity.
This is now posing serious questions con-
cerning their undisputed acceptance and
unrestricted use in foods, and emphasizes
the need for an extensive program of toxi-
cological evaluation. In view of the very
large number of materials used, their diver-
sity, their low usage rate and low total
consumption, as well as their low cost re-
lative to other food ingredients, flavorings
have not been subjected to any extensive
toxicological evaluation to establish their
876
safety in use either in the shortor long-term.
For flavorings of natural origin, long usage
without any apparent ill effects has been a
sufficient criterion for their continued use,
which indeed is essential if an adequate and
varied diet is to be provided to meet present
demands.
The laws and regulations governing the
use of food additives, whatever their nature,
are normally the result of a government's
concern for the health and well-being of its
people. In the more advanced countries,
such legislation is often complex and wide-
ranging, in others it lacks precision, and in
many countries it may be nonexistent. At
present, there is little basis for agreement
either on the extent or the nature of legis-
lation governing the use of flavorings, as is
clearly shown in reviews by Schlegel (1971),
Jenkins (1975) and Jones (1976). As food
products are required to comply with the
law of the country in which they are sold for
consumption, this lack of uniformity of
legislation and control imposes a burden on
the food manufacturer to ascertain and inter-
pret correctly the regulations as they apply
in each country. Frazer (1960) pointed out
at a symposium in London to commemorate
the centenary of the first general pure food
law in the English speaking world:

The making of laws is not necessarily beneficial.
A complex and ill-founded legislative machinery
may do more to hamper progress than to protect
the community; indeed, the interference with
technological and other advances may prove to
be more harmful to the community than any of
the alleged dangers that the law is attempting to
control.
There is a clear body of opinion that
legislation should only be promulgated
where a positive benefit to consumers can
be shown and that this benefit cannot be
obtained in any other way. It should also be
appreciated that well-intentioned legislation
may unintentionally prohibit the manu-
facture or sale of perfectly wholesome food
products due to the inflexibility of bureau-
cratic dictates. Frequently, legislative
control goes too far and no legislation
should be necessary for acceptable pro-
ducts, whatever their precise composition,
so long as the labeling is clear and suf-
ficiently adequate to ensure that consumers
are fully informed of the true nature of the
goods and so can form a judgment on their
acceptability to them. In the United States,
a Regulatory Council has been established
to coordinate regulatory activities and to
help ensure that regulatory objectives are
achieved in a fully cost-effective manner
(Federal Register, Oct 17, 1979).
Where it exists, the legislation governing
food additives is normally aimed at pro-
hibiting the sale of any article of food or
other consumable product containing in-
jurious or poisonous ingredients. This is
achieved by applying four main principles:
a. Prohibit the addition of anything to
food which may be injurious to health
in the shortor long-term.
b. Provide for standards of purity,
tolerances and methods of analysis.
c. Define the disclosure of contents on
labels as a guide to the consumer.
d. Define any exemptions.
The basic features of modern flavor
legislation have been set out in a booklet
International Flavor Legislation 877
published by the International Organization
of the Flavor Industry (IOFI 1976). This
presents a worldwide consensus of experts
in this field and, hopefully, its recommen-
dations will act as a guide to legislators in
the drafting of more uniform regulations
governing flavorings.
DEFINITIONS
Flavorings are generally considered to be
deliberate or intentional food additives and
for an understanding of the law, it is nec-
essary to have a clear definition of both
"food additive" and "flavoring."
Food Additives
The following definition was accepted by the
Commission of the Codex Alimentarius in
1974:
Any substance not normally consumed as food by
itself and not normally used as a typical
ingredient of the food, whether or not it has
nutritive value, ifthe intentional addition of
which to a food for technological (including
organoleptic) purpose in the manufacture,
processing, preparation, treatment, packing,
packaging, transport, or holding of such food
results (directly or indirectly) in it or its by-
product being a component of or otherwise
affecting the characteristics of such food. The
term does not include "contaminants" or
substances added to food for maintaining or
improving nutritional qualities. (Document:
FAO/WHO/C/73.1.)
Flavorings
The basic definition of a !'flavoring" is given
in the Food Additives and Contaminants
Committee Report on the review of
flavourings in food, 1976:
Flavoring means any substance which is capable
of imparting and is generally used to impart taste
or odour or both to a food.
It is admitted that this definition is very
wide and embraces materials which might
properly be regarded as foods in their own
878 Source Book of Flavors
right (e.g., cheese, nuts, vegetables, etc.) so
that the term "flavoring" should be taken to
exclude: (a) any naturally occurring con-
stituent of a natural food substance when it
is present in a food solely by virtue of that
natural food substance being used as an
ingredient of the food; (b) any substance
present in a food or its ingredients as a result
of changes which have taken place during
the preparation of the food; and (c) any
permitted food additives already controlled
under separate legislation.
Within this definition, flavorings may
then be further classified in order to deter-
mine the way in which they are to be
designated in product titles and label de-
scriptions. These classifications differ
between countries:
Accepted in the United States
The following U.S. definitions are accepted:
1. Natural Flavorings. The essential oil,
oleoresin, essence, extractive, protein
hydrolysate, distillate, or any product of
roasting, heating, or enzymolysis which
contains the flavoring principles derived
from a spice, fruit or its juice, vegetable
or its juice, edible yeast, herb, bark,
bud, root, leaf or similar plant material,
meat, fish, poultry, eggs, dairy products,
or the fermentation product of any of the
above.
2. Artificial Flavorings. Any flavoring
which is not derived from the sources
which yield natural flavorings.
3. Spice. Whole, broken or ground aro-
matic vegetable substances except sub-
stances traditionally recognized as foods
(e.g., onions, garlic, celery); no portion
of the volatile oil or flavoring principle
may be removed.
4. GRAS. Means "generally recognized as
safe" by experts.
Accepted By IOFI
The following definitions were accepted by
the Commission of the Codex Alimentarius
Committee on food additives:
1. Natural Flavours and Flavouring Sub-
stances. They are preparations and
single substances respectively, accept-
able for human consumption, obtained
exclusively by physical processes from
vegetable, sometime animal, raw ma-
terials either in their natural state or
processed for human consumption.
2. Nature-identical Flavouring Substances.
They are substances chemically isolated
from aromatic raw materials or obtained
synthetically; they are chemically iden-
tical to substances present in natural
products intended for human consump-
tion either processed or not.
3. Artificial Flavouring Substances. They
are those substances which have not
yet been identified in natural products
intended for human consumption either
processed or not.
These definitions were accepted by the
British Food Additives and Contaminants
Committee in their report on flavourings
except that the word "Synthetic" is used
instead of "nature-identical."
Most national legislation includes a
preamble giving the appropriate definitions
and this section should be carefully con-
strued to ensure compliance of any flavoring
products involved.
SYSTEMS OF CONTROL
Any legislation implies a system of en-
forcement; the method adopted is deter-
mined to some extent by political consider-
ations but may be dictated by the technical
and economic resources available to ensure
compliance without prejudice or undue
restriction of trade and without exposing the
community to unwarranted risks. Assuming
that some sort of flavor legislation is highly
desirable, then this may be achieved in one
of three ways:
a. Negative list-in which are defined all
flavoring substances which are pro-
hibited for inclusion in foods or may
be used only to a very limited extent;

all other nonlisted flavoring materials
are acceptable. This system is gen-
erally considered to be over-simple
and offers inadequate protection to
consumers. Even so, it is still widely
applicable in countries of the British
Commonwealth, South America, and
in Belgium, France and Denmark.
In the United Kingdom, the Food
Standards Committee in 1965 recom-
mended the prohibition of 16 flavor-
ing substances; this was not accepted
into law and the list now acts as a
guide to manufacturers.
b. Positive list-which defines all the
individual substances which are per-
mitted for use in food flavorings. Any
substance not listed is automatically
prohibited. Such a list is inevitably
incomplete. Natural products are in-
cluded even though their chemical
composition is not yet fully estab-
lished so that newly identified com-
ponents are not acceptable until
individually accepted. The inclusion
of a chemical in a positive list implies
a warranty on the part of the legis-
lative agency that the substance is
indeed safe for use under the condi-
tions stated. Such positive lists are
necessarily limited; involve consider-
able and very expensive toxicological
testing to be completed before ac-
ceptance of any new listing; are
restrictive of technological develop-
ment and research into new flavoring
materials; and are almost impossible
to enforce. Even with modern in-
strumental methods, the finite
analysis of a complex flavoring mix-
ture is very difficult to achieve with
any certainty. The system currently
being evolved in the United States is
basically a positive list, the precise
enforcement of which has still to be
demonstrated.
c. Mixed system-this offers the best of
both former options in that flavoring
materials are appraised both toxi-
International Flavor Legislation 879
cologically and by their prior use in
foods without ill-effect. Natural and
nature-identical components are per-
mitted and the use of artificial flavor-
ing materials is regulated to a degree
corresponding to the recognizable
risks. The system gives very adequate
consumer protection without undue
costs; it can be enforced technically;
and the method of approval does not
restrict research into new flavoring
substances.
The advantages and disadvantages of
these three systems of control have been
well discussed by Downer (1974), Vodoz
(1977) and in the IOFI booklet (1976).
WORLDWIDE REVIEW OF
FLAVOR LEGISLATION TO 1979
The major industrial countries have devel-
oped their food legislation independently
over a considerable number of years and
although their intentions are broadly similar
(i.e., to ensure the safety and wholesome-
ness of the food consumed by the com-
munity and to prevent fraudulent claims as
to its true nature) the methods of control
differ significantly. The following review by
countries has been updated as far as possible
but this area of legislation is under constant
consideration by the various regulatory
agencies and amendments are frequent. The
system currently in force is given in Table
23-1.
ARGENTINA
Legislation provides for commodity stan-
dards rather than specific lists of food addi-
tives. Standards for natural extracts are
defined. Short positive and negative lists are
enforced.
Legislation
Codigo Alimentario Argentino. Decree
No. 2.126, Articles 1298-1321.
 880 Source Book of Flavors

TABLE 23-1. Types of Flavoring Legislation in Use Worldwide in 19791

No Specific Flavor Negative List of Positive List of Both Positive Flavorings Requiring
Regulations-General Prohibited Permitted and Negative Prior Government
Food Laws Apply Substances Substances Listings Authorization
Austria Australia Japan Argentina Bulgaria
Belgium Brazil Romania 2 Germany Czechoslovakia
Denmark Canada Soviet Union 2 Italy Finland3
Eire Oreland) Chile Switzerland Netherlands Hungary
France India United States• Spain Peru
Greece New Zealand Yugoslavia Poland
Jamaica Singapore
Luxembourg
Norway
Portugal
South Africa
Sweden
United Kingdom 3
1 Legislation is frequently changed and reference should always be made to the appropriate authority for the up-to-
date position.
2 Very short positive list coupled with prior government authorization.
3 Positive list in preparation but not yet accepted into law.
• GRAS list with very short negative list and product group specifications.

AUSTRALIA
Flavors are considered as a food rather
than as food additives. There is no list of
approved flavoring substances and foods
may contain flavorings, both natural and
artificial, that are regarded as safe. Other
than in Victoria and Tasmania, there is a
negative list of prohibited substances which
must not be used in food flavoring.
Flavors may contain designated solvents,
carriers, emulsifiers, stabilizers, thickening
or gelling agents, acids, colors and preser-
vatives, the maximum permitted use levels
of which are prescribed. The national law
governing food and additives is subject to
state legislation and local regulations must
be checked to ensure compliance.
When flavors are incorporated into
standardized food products in accordance
with the current regulations, such products
with some exceptions (e.g., cocoa, choco-
late, cheese, confectionery, cakes and other
flour products excluding bread) must be
labeled "artificially flavored" irrespective of
the nature of the flavoring incorporated.
Nonstandardized food products may contain
added flavorings without declaration.
Legislation
Food and Drugs Act:
Regulation 3. Flavourings and Colourings
Regulation 49. Essences
This act is subject to amendment by state
legislation.
AUSTRIA
The present legislation, effective since July
1, 1975, defines food additives, which in-
cludes flavoring materials, in simple terms
and forbids the use of all nonpermitted
additives. The Ministry of Health and
Environment, acting under the advice of the
Austrian Codex Commission, determines
the acceptability and use levels of all addi-
tives whatever their nature. A positive list is
anticipated, but the extent and content of
such a list has not yet been defined.
The composition of imported food pro-
ducts must be filed with the Ministry for
prior authorization and a list of ingredients
in descending order of quantity present
must appear on the label. Flavorings are
declared either as "naturlich aromatisiert"
(naturally flavored) or "mit naturlichem

Aroma" (with natural flavor) if natural
flavors only are used; or, either "kunstlich
aromatisiert" (artificially flavored) or "mit
kunstlichem Aroma" (with artificial flavor)
in all other cases.
Legislation
Lebensmittelkennzeichnungsverordnung,
1973.
Lebensmittelgesetz, 1975.
BELGIUM
There is no specific legislation governing
flavoring materials. All substances which
are not harmful may be used in foods and
there is a negative list of materials which are
prohibited. This includes: coumarin and its
derivatives, chloral, chloroform and ether.
It is probable that Belgium will ultimately
adopt some system within the proposals of
the E.E.C.
Sodium, potassium and calcium salts of
glutamic acid are specifically permitted in
seasonings up to 200 g/kg.
Legislation
Arrete ministeriel du 18.9.67 fixant Ia liste
des additifs autorises dans le commerce des
denrees et substances alimentaires (as
amended).
Decisions ministerielles du 6.2.70 rela-
tives a l'autorisation d'emploi d'additifs
dans les denrees alimentaires.
BRAZIL
Flavorings are defined as either natural or
artificial and a small permitted list of arti-
ficial flavoring substances is published. This
includes: acetaldehyde, amyl acetates,
butyrates and valerates, anethole, benzal-
dehyde, cinnamic aldehyde, citral, cou-
marin, diacetyl, ethyl acetates, glycerol,
propenyl guaethol, and vanillin. There is
also a negative list of harmful substances
which are prohibited for use in foods. The
International Flavor Legislation 881
food additive legislation lists all permitted
additives and gives the maximum use levels
in each category of food products in which
they are permitted.
The use of added flavorings, both natural
and artificial must be declared on the label
either as "flavor from __ , (stating the
natural source), or "contains flavoring," or,
in the case of artificial flavorings, "artificial
from __, or "artificially flavored."
Legislation
Decreto No. 50.040 de 24.1.61, referente a
normas reguladoras do emprego de aditivos
para alimentos (as amended).
BULGARIA
Current legislation on food additives be-
came effective on February 12, 1972. There
is a general edict governing the use of
flavoring substances. Any flavoring material
which has a lethal dose (LD50) of less than
1000 g/kg by intraperitoneal administration
to rats cannot be used. Vodoz (1975)
points out that this is the only example of
categorization based on this type of toxi-
cological test. There is a limit for all added
flavoring materials of 300 ppm in the end
product.
The Ministry of Public Health is the
approving authority and the composition of
all flavorings must receive prior authoriza-
tion before use. Lists of permitted sub-
stances include essential oils and a limited
number of synthetic chemicals which may be
used in defined food products.
Legislation
Health Rules Nos. 0-36 (published in
D'rzaven Vestmik, 1972, 12, 4-7).
CANADA
Under the Food and Drug Regulations
both natural and artificial flavorings are
permitted for use within the regulations
882 Source Book of Flavors

governing individual food categories. No list Legislation

of permitted flavorings exists but current
Regulations to the Food and Drug Act,
usage tends to follow the GRAS lists of the
amended to date.
United States. A negative list of prohibited
Part B-Foods
substances is enforced (Section B.Ol.046)
including: mineral oil or paraffin wax or any
Division 6. Colours
preparation thereof; coumarin, an extract of
Division 7. Spices, dressings and seasonings
tonka beans, the seed of Dipteryx odorata
Division 10. Flavouring preparations
Willd. or Dipteryx oppositifolia Willd.;
nonnutritive sweetening agents; dihydro-
safrole; isosafrole; oil of American sassafras CHILE
from Sassafras albidum (Nutt) Nees.; oil of
Brazilian sassafras from Ocolea cymbarum The legislation for the use of food additives,
H.B.K.; oil of camphor sassafrassy from including flavoring materials, is based on
Cinnamomum camphorum Sieb.; oil of the Latin American Food Code and the
micranthum from Cinnamomum mic- standards of the Codex Alimentarius. There
ranthum Hayata; safrole; oil, extract or root is a prohibited list of flavoring ingredients
of calamus from Acorus calamus L.; nut and which includes: alcohols (except ethyl
nut products that contain more than 15 alcohol); acids (except citric, lactic and
parts per billion of aflatoxin and ethylene tartaric acids); benzaldehyde; and other
thiourea. harmful substances.
Flavoring preparations are defined in five
different ways depending on the source of CZECHOSLOVAKIA
their constituents and composition. These
include: natural flavour extract or essence, The use of all food additives, including
artificial or imitation flavour extract or flavoring materials, requires the prior
essence, natural flavour, artificial or imita- approval of the Department of Health.
tion flavour, and natural extract or essence There is no legislation specific to flavorings
naturally fortified (51% of the flavoring although their composition and use level
strength being derived from the named must be authorized.
fruit).
The regulations require that on any label Legislation
or in any advertisement for an artificial or
imitation flavoring preparation the word Ministry of Health, Decree No. 5190 (1967).
"artificial" or "imitation" shall be an (Reference: Recueil International de
integral part of the name of such flavoring Legislations Sanitaires, 18, 543).
preparation and in identical type and iden-
tically displayed with such name.
DENMARK
Nineteen flavor essences are specifically
defined in this legislation. These include: A new food law was introduced in June 1973
almond, anise, celery seed, cassia cinna- in which requirements for nutrition and
mon, Ceylon cinnamom, clove, ginger, quality are defined. In general terms, it is
lemon, nutmeg, orange, peppermint, rode, forbidden to sell foodstuffs contaminated
savory, spearmint, sweet basil, sweet with any material which, in the opinion of
marjoram, thyme, vanilla, and wintergreen. the Minister of the Environment, is liable to
cause any hazard to health. This legislation
includes lists of approved food additives and
their uses, with specifications for identity
and purity. A revised list was promulgated

effective July 1976. The National Food
Institute is responsible for listing detailed
permitted use levels and maximum con-
centrations. Notice of all flavoring materials
and formulations used must be filed with the
Institute. Although the use of food additives
in various types of food products is defined,
flavorings are presently excluded from these
listings. The Danish food standards for
cocoa and chocolate products permit the use
of vanillin and ethyl vanillin but other than
this no general listing of flavorings has yet
been issued. Legislation restricting the use
of certain aromatic substances in foodstuffs
was published in March 1978. The list
includes: substances (Annexes 1 and 2) or
extracts or concentrates thereof of agaricin,
P-asarone, berberine, coumarin, ethyl-
3-phenyl2,3-epoxybutanoate, 5( or 6)-hexyl-
1,4-dioxanone-(2), hydrogen cyanide,
isosafrole, hypericin, quassin, nitrobenzene,
pulegone, ricin, safrole, santonin, sparteine,
thujone, trichloromethane, and the follow-
ing natural plant materials:
Anemone hepatica (herb), Atropa bella-
donna (whole plant), Bryonia dioica
(roots), Chenopodium ambrosioides
(herb), Convallaria majalis (whole
plant), Daphne mezereum (whole plant),
Dryopteris filix-mas (rhizomes), Helio-
tropium europaeum (leaves), Piscidia
erythrine (roots), Polypodium vulgare
(roots), Punica granatum (roots), Ruta
graveolens (herb), Ulmus fulva (bark),
Uragoga ipecacuanha (roots), and
Urginea scilla (bulb).
The following substances may not appear
naturally in quantities exceeding those
stated in Annex 3 in foodstuffs or in addi-
tives sold for use domestically: agaricin
(0.5ppm); P-asarone (0.1ppm); berberine
(0.1 ppm); coumarin (0.2 ppm); hydrogen
cyanide (0.1ppm); hypericin (0.1ppm);
isosafrole (0.1 ppm) with the total of saffrole
and isosafrole a max 0.1 ppm; quassin
(0.1 ppm); pulegone (0.1 ppm); ricin
(0.1 ppm); safrole (0.1 ppm); santonin
International Flavor Legislation 883
(0.1 ppm); sparteine (0.1 ppm); and thujone
(0.5 ppm). Further limitations on these
substances are listed in specified foods in
Annex 4 of the legislation.
Legislation
Fortegnelse over godkendte tilsaetningsstoff
til levnedsmidler (Positivlisten), Oktober
1975.
FINLAND
Natural flavorings and products made
from fruit, vegetables, herbs and spices by
pressing, extracting or distilling are all
permitted without declaration. Flavorings
containing any nature-identical or artificial
ingredients may only be used in the 15
specified groups of food products in accor-
dance with the list of food additives at the
maximum prescribed levels or in quantities
which do not constitute a hazard to health.
New flavoring legislation is under review. In
this, flavorings will be divided into three
classes, namely, natural, nature-identical
and artificial, all of which would have to be
declared on the end-product label. The draft
legislation includes (a) a restrictive list
of natural and nature-identical flavorings
stating their maximum permitted use levels,
(b) a positive list of artificial flavoring
substances, and (c) a list of other food
additives.
Presently, artificial flavorings are per-
mitted without declaration in cake mixes,
chocolate and chocolate fillings, sugar
confectionery, chewing gum, artificial
sweetening agents, and in certain soft drinks
(lemonade). They are permitted with
declaration (i.e., "essence artificiella") in
milk, jelly, edible ices, meat broth and
concentrates, processed breakfast foods,
crisps, crackers, and snack products, flour
confectionery, imitation fruit juices and
jellies, fruit berry and vegetable beverages,
imitation milk beverages, and mead and
cider. Artificial flavorings are specifically
limited with declaration in dried milk pro-
884 Source Book of Flavors
ducts to max 0.1% (diacetyl max 0.1%;
butter acids max 0.03%); oil and fats emul-
sion and mayonnaise max 0.006%; flour
confectionery (vanillin and ethyl vanillin
max 0.1% ); flavored sugars (vanillin and
ethyl vanillin max 2%); imitation milk
beverages (diacetyl max 0.01%); other
foods (vanillin and ethyl vanillin max
0.1% ). Flavorings are not permitted in eggs
and egg products, fish and fish products,
vegetables, salt, vinegar, spices and natural
flavorings, coffee and tea.
Legislation
Forteckning over tillsatsamnen tillatna for
anvanding i livsmedel (Nr.953/73,20.12.73).
FRANCE
Currently no flavoring regulations have
been promulgated although the legislation
governing foods prohibits adulteration and
the use of harmful or toxic ingredients and
imposes strict penalties. A code of practice
adopted by the French flavor industry de-
fines various types of flavorings: natural
flavors are permitted without restriction;
nature-identical and artificial flavorings are
acceptable provided that their use is con-
sidered to be safe either by long usage or on
the basis of toxicological data.
Only natural flavorings may be added to
dairy products and beverages.
When flavorings are used, the following
declarations must be made as appropriate:
Arome naturel-when the added flavoring
is entirely natural.
Arome artificiel-when the flavor con-
tains nature-identical and/or artificial
substances.
Arome autorise-when the added flavoring
is in accord with specific regulations
governing the use of artificially reinforced
flavors. These comprise a natural flavor-
ing boosted by the addition of small
quantities of nature-identical flavoring
substances. They may be used in specified
food products, namely: sugar and flour
confectionery, chocolates, pastries, fill-
ings, decorations, instant dessert prep-
arations, beverage powders including
all vegetable flavors except citrus fruit
and vanilla at max 4 g of nature-identical
flavoring per kilo of natural flavor which
has been concentrated at least 4-fold (or
3-fold in the case of coffee).
Yogurt, curdled or gelled milk, flavored
milk: apricot, pineapple, banana, straw-
berry, raspberry, pear, plum, and cherry
at max 2 g per kilo of natural flavor
which has been concentrated at least
4-fold.
Preparations with fruit and sugar for yogurt
and fresh cheese with fruit: apricot,
pineapple, cherry, strawberry, banana,
raspberry, pear, and plum at max 4 g per
kilo of natural flavor which has been
concentrated at least 4-fold. The total
addition of nature-identical substances
must not exceed 200 mg per kilo of
preparation at the time of use.
References
Le commerce des matieres aromatiques
pour les industries alimentaires. Convention
entre les fabricants. Juin, 1957.
Legislation
Decret No. 72,937 du 12 octobre 1972
portant application de la loi du ler aout 1905
sur la repression des fraudes.
GERMANY
Food flavorings are governed by the general
food law "Lebensmittelgesetz" which
forbids falsification and mislabeling and
prohibits the use of any substances in
foods which may be hazardous to health.
Under specific regulations "Essenzen
Verordnung," effective August 1974,
natural and nature-identical flavoring sub-
stances are not regarded as food additives.

Such materials are regulated by a prohibited
list which includes: agaric acid; bittersweet
stems; coumarin; tonka bean; wild vanilla;
yellow melilot and (sweet) woodruff;
pennyroyal; quillaia bark; tansy; rue;
safrole; sassafras wood; leaves, bark and oil
of camphor wood; camphor oils containing
safrole but not nutmeg: polypody root;
birch tar oil; bitter almond oil containing
free or combined hydrocyanic acid; juniper
tar or cade oil; thujone with the exception of
plants and parts of plants containing thujone
such as wormwood and mugwort; calamus
oil containing more than 10% asarone.
In addition to the above, the following
natural products have a restricted use:
Peruvian bark, cinchona, quinine and its
salts, quassia wood, calamus oil containing
less than 10% asarone.
Artificial flavoring materials which
are not nature-identical are classified as
"Fremdstoffe" and may only be used as
defined in a short positive permitted list of
17 substances which includes: ethyl vanillin
hydroxycitronellal, propenyl guaethol, and
dimethyl resorcinol. These substances are
permitted for use in artificial drinks, cream
desserts, puddings, jellies, syrups, artificial
ice cream, flour confectionery, sugar con-
fectionery, chocolate fillings, chewing
gum, and tobacco. In all cases, their use
must be declared as "mit kunstlichem
Aromastoffe."
Some food categories have further re-
straints on the use of added flavorings (e.g.,
ethyl vanillin may be used in chocolate
without declaration so long as the flavor
does not predominate). Nature-identical
substances are not regarded as natural
flavorings and hence may not be used in
certain categories of foods (e.g., ice cream,
soft drinks) in which only natural flavorings
are permitted.
Solvents and carriers permitted for use in
flavorings are also specified and the addition
of flavor enhancers is regulated.
International Flavor Legislation 885
Legislation
Verordnung uber Essenzen und Grund-
stoffe in der Neufassung vom 9.10.70; last
amended January 1, 1978.
Lebensmittel und Bedarfsgegenstan-
degestz vom Aug. 15, 1974; last amended
April 9, 1976.
GREECE
A new Greek Food Code was introduced
into the legislation in April 1971. This is a
basic law embracing the use of food addi-
tives, spices and essential oils and defines
11 groups of food products. Flavoring
materials are not specifically controlled.
HUNGARY
The acceptance of natural flavoring ma-
terials for use in foodstuffs is authorized by
the Ministry of Health, which also deter-
mines what chemicals and food additive.s are
considered to be hazardous to health. These
are prohibited for use in foods although a
negative list has not been published. The
legislation requires prior authorization for
use.
Legislation
Ministry of Health, Decree No. 27 and 50
(1961). Reference: Recueil International de
Legislations Sanitaires, 12, 361.
INDIA
Food and food additives are controlled
under the India Health Laws and the as-
sociated regulations. Act No. 37, which has
been in force since September 1954, makes
provision for the prevention of adulteration
in food products. The Prevention of Food
Adulteration Rules 1955, have since been
significantly amended and now include
sections covering food colorings and flavor-
ing agents. There is a short negative list of
prohibited flavorings as well as a list of
permitted solvents and a section on spices.
 886 Source Book of Flavors

Legislation trolled by means of a permitted list which

Prevention of Food Adulteration Rules,
1955, Part XIII made under the India
Health Law, Act No. 37, 1954.
ITALY
Italy permits the use of natural flavorings,
listed in the Ministerial Decree of March 31,
1965 and its amendments, together with the
following products derived from edible
plants: alcoholized, concentrated or de-
hydrated juices; essential oils, simple,
rectified or terpeneless; essences, concen-
trates and extracts of flavoring substances;
tinctures and infusions; distilled flavors;
constituents of natural flavors, extracted,
isolated, or reproduced by chemical syn-
thesis; constituents of natural substances,
even if not flavorings extracted, isolated or
reproduced by chemical synthesis and which
enhance the flavor or odor of food. All of
the above may be declared as "natural
flavors."
Artificial flavoring substances are con-
contains only 17 chemicals, the maximum
use of which in certain food categories is
stipulated (Table 23-2).
Completely natural flavorings are
permitted provided that they have not
been chemically modified or in any way
synthesized.
Legislation
Decreto ministeriale 31 marzo 1965.
Disiplina degli additivi chimici consentiti
nella preparazione e per Ia conservazione
delle sostanze alimentari (as amended).
JAMAICA
The Food and Drug Regulations made
under the Food and Drugs Act 1964 were
published in March 1975. These control the
manufacture and sale of foods, drugs, cos-
metics and devices. Division II-Food
specifies levels of permitted preservatives
and artificial sweeteners but does not in-

TABLE 23-2. Arficial Flavoring Substances Permitted for Use in ltaly 1

...."'
...;.
Q) Q)

...
Q)
~
.2...."'
Q)
r:n
..."'
Q)

'1Q)
::1 "'
Q) '1::1 Q)

e ...
... ....,"' r:..'1::1
p..
~
~ "' e
J ....
0 Q)

...."'s:: ..."' p..

"'bll
Q)

·o::s::
r:n~ ..."'
·s...."' 8"'
;:l

.s-"' :§'1::1 ....s:: s:: :a

Q)
iil;:l bll
"'2.'l
Q)

"'
Q)
'1::1
... s:: u
"' "' s::
- -"'
'1::1 '1::1 Q)

Chemical Substances and ~

& u"' :E"'
0
~
Q)
~
"' .S'
"'
,..c:; ,..c:; ·o Q)

Permitted Use in ppm :r: r:..0 ...:l i:iS ~

;:l
p.. u u
Allyl hexanoate 2
Allyl cyclohexyl propionate 2 1
Amyl hexanoate 2
Dimethyl resorcinol 1
Ethyl acetoacetate 2 2
Ethyl ~-naphthol 1 1
Ethyl methyl phenyl glycidate 10 5 10 100
Etht vanillin 200 50 50 200 200 200 100 100 100 100 900 5
Hy roxycitronellal 0.5 0.25 0.5
Methyl cyclopentolone 1
Methyl heptine carbonate 2 1
Methyl ionones 0.25 0.25 0.25 0.25
'Y- Nonalactone 1 0.5
Naphthyl methyl ketone 0.1
P~nyl guaethol 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2
b olualdehyde
ndecalactone 10
2 2
5 5

'Some of the above chemicals are now recognized as nature-identical but must still be declared as artificial.

elude other food additives. The definition of
"food additives" does not include spices,
seasonings, flavouring preparations, essen-
tial oils, oleoresins, and natural extractives.
In general, foodstuffs are manufactured to
comply with the regulations of the United
Kingdom. There is a list of prohibited sub-
stances which includes: mineral oil (at a
level above 0. 3%); paraffin wax (except as a
base in chewing gum or as a coating for
turnips and cheese and, at no more than
0.3%, for fresh fruit and other vegetables);
coumarin; tonka-bean extracts; specified
Dipteryx seeds; synthetic sweeteners other
than saccharin; cottonseed flour containing
more than 450ppm free gossypol; fatty acids
and their salts containing "toxic factors";
dihydrosafrole; isosafrole; oil of American,
Brazilian or camphor sassafras; oil of
Micranthum hyata; and safrole.
Legislation
Food and Drugs Act 1964, as amended.
Food and Drug Regulations 1974 (pub-
lished in Jamaica Gazette Supplement,
1975, 98, (18), 129 dated March 3, 1975.
JAPAN
Natural flavorings are regarded as foods and
are not directly controlled. All permitted
food additives, including nature-identical
and artificial flavoring substances are listed
as specific chemical compounds and also by
chemical groups; e.g., aliphatic higher
aldehydes (except harmful substances). This
gives a degree of latitude to the positive
listings. Other food additives are listed
according to their application. Maximum
use levels are prescribed although flavoring
agents are listed only as "for purpose of
flavor." Chemical substances which may be
imported for use in flavorings are also listed.
Legislation
Food Sanitation Law No. 233 dated Dec.
24, 1947, last amended Jan. 25, 1976.
International Flavor Legislation 887
Enforcement regulations to the Food
Sanitation Law, No. 23, dated July 13, 1948,
last amended Feb. 18, 1977.
Reference
Food Sanitation Law and Food Additives in
Japan, Revised 7th Edition. The Federation
of Food Additives Associations in Japan,
1978. (English)
THE NETHERLANDS
Flavor legislation has recently been intro-
duced. There is now a short restrictive list of
natural and nature-identical substances, but
otherwise these categories of flavoring
agents are permitted. There is a fairly long
list of artificial flavoring agents which may
be used within the maximum limits pre-
scribed for each group of finished food-
stuffs. There is also a list of other flavoring
adjuncts.
Legislation
Warenwet dated Dec. 28, 1935, as amended.
Reference: Beschikking geur-en maak-
stoffen, Nederlandse Staatscourant, Feb.
13, 1980.
NEW ZEALAND
The legislation permits the use of any
flavoring substance which is wholesome and
presents no hazard to health. The use of
flavorings and other food additives to
specific food product groups and commo-
dities is the subject of individual regula-
tions. There is a short negative list of
prohibited substances which includes: cade
oil, coumarin, nitrobenzene, pyroligneous
acid, safrole and isosafrole, and sassafras
oil. The following solvents are permitted in
the manufacture of flavorings: ethyl acetate,
ethyl alcohol, glycerol, glyceryl acetates,
isopropyl alcohol, and propylene glycol.
In the list of ingredients to be declared on
the label of food products any added
888 Source Book of Flavors
flavoring materials must be shown as
"flavour."
Legislation
The Food and Drug Regulations, 1973.
Part 1. Food Additives, 20. Flavouring
substances.
Part 11. 212. Culinary essences, extracts
and flavourings.
213. Artificial culinary essences, extracts
and flavourings.
NORWAY
The current legislation groups foods into ten
categories and defines the additives per-
mitted in each. Essential oils, natural
essences and nontoxic artificial flavorings,
vanillin and ethyl vanillin are listed and may
be used in milk and milk products; ice
cream; wholly preserved and semipreserved
fish products; flour and baker's goods,
pastries, biscuit creams; preserved fruits and
vegetables; candied fruit and substitutes;
fats, oils, margarine, bakery fats and
shortening; cocoa, chocolate and confec-
tionery; and certain other products. Only
natural flavorings may be added to fruit
drinks and lemonade but artificial flavorings
may be used in other carbonated beverages.
No flavorings are permitted in egg products,
meat and meat products.
Legislation
Fortegnelse over de for 1975 godkjente
tilsetningsstoffer.
PERU
Legislation is in line with the Latin
American Food Code and imported
flavoring materials must be registered and
receive prior authorization by the Inspector
General of Pharmacy.
POLAND
Natural and artificial flavorings are con-
trolled by legislation effective June 1971.
Natural flavoring materials, essential oils,
distillates and juices are all permitted and
there is a list of permitted artificial flavoring
substances. Blended flavorings may only be
made with ethanol as the solvent. With the
exception of milk, butter, margarine, edible
fats, oils, wine, and certain beverages in
which flavorings are prohibited, all other
products may contain flavorings as con-
sidered desirable; there are no specified use
level limits.
PORTUGAL
There are no regulations governing the use
of flavorings in foodstuffs.
ROMANIA
All natural flavorings are authorized with-
out restriction. A short permitted list of
artificial flavorants includes only ethyl
vanillin, butyl acetate, ionone, methyl
naphthyl ketone, and diactyl; all other
artificial flavoring substances are prohibited.
Legislation
Ministry of Health and Welfare, Decree
No. 846, (1963), Article 305.
SINGAPORE
Food Regulations which were introduced in
1974 provide standards for several natural
essences and define spices and artificial
flavorings. There is no positive list but there
is a short prohibited list of natural flavoring
materials. Glyceryl di- and triacetates are
not permitted as solvents for flavorings.
Legislation
The Food Regulations, 1974, Article 18.

SOUTH AFRICA
Both natural and artificial flavorings are
permitted and there is presently no listing of
approved flavoring substances. Standards
are prescribed for certain individual food
products and the use of flavorings and other
food additives in these must comply with the
regulations. The use of flavorings in foods
must be declared on the label as "flavouring
agents."
Legislation
Foodstuffs, Cosmetics and Disinfectants
Act and Regulations, 1972, as amended.
SOVIET UNION (RUSSIA)
The present legislation covers natural
flavorings, essential oils, extracts and spices.
It provides a short positive list of permitted
synthetic flavourants defining their maxi-
mum use levels and specific applications. In
general, prior authorization is necessary for
the use of any additives in food products.
This is carried out by the All State Union
Sanitary Inspectorate of the Ministry of
Public Health. A short list of prohibited
flavoring materials includes coumarin,
~-naphthol ester, acetaldehyde, chloroform,
propylene glycol, and triacetin.
SPAIN
The Spanish Food Code has been effective
since March 12, 1975. It permits the use
of natural, nature-identical and artificial
flavorings which present no health hazards
and prohibits the use of the following sub-
stances in foods: hydrocyanic acid, methyl
and amyl alcohols, coumarin and tonka
beans, diethylene and triethylene glycol,
nitrobenzene, nux vomica, safrole and
sassafras oil, saponins, and other toxic
substances. The format of the regulations is
closely similar to those recommended by
IOFI.
The permitted lists include 294 artificial
International Flavor Legislation 889
substances and 10 nature-identical com-
pounds; and maximum use levels are de-
fined. A list of permitted solvents is also
prescribed.
Legislation
Decreto No. 406/1975 de 7 de marzo,
por el que se aprueba Ia Reglamentacion
Technico-Sanitaria de los Agentes Aro-
maticos para Ia Alimentacion.
SWEDEN
There is currently no legislation specifically
controlling flavoring materials. Nontoxic
essences and flavorings which are generally
regarded as safe may be used in foods as
permitted for the individual product group,
namely: baby foods; cheese; margarine and
minarion; edible ices; meat products other
than meat, minced meat, organs and meat
by-products; bread and certain bakery
products; fruit and vegetables; jam, mar-
malade and jelly; carbonated beverages;
and certain other foods. Spices and
oleoresins are permitted for use in fish and
fishery products which are fully preserved,
semipreserved or chilled, but some classes
of product are excluded.
Flavorings may not be added to milk and
milk products; butter, lard and edible
tallow; meat, minced meat, organs and meat
by-products; fish products including alkali-
cured products; cooked crustaceans and
certain other products; eggs and egg pro-
ducts; macaroni and spaghetti; fruit nectars
and syrups; fruit juice; sugar; honey; coffee;
tea; salt; and vinegar.
The incorporation of other food additives
is precisely controlled; maximum use levels
and applications are prescribed for each
additive.
The use of any flavoring in a food pro-
duct must be declared on the label as
"Smakamne" (flavoring).
890 Source Book of Flavors
Legislation
Statens livsmedelsverks kungorelse om
livsmedelstillsatser, SLY 1975, dated June
3, 1975, as amended by SLY, 1977.
SWITZERLAND
Like all other food additives, both natural
and artificial flavoring substances are re-
garded as foreign substances and may not
be used unless specifically permitted in
the regulation governing each group of
food products. There is now a list of per-
mitted flavoring materials and all harmless
flavorants may be used within the above
restrictions. All flavors must receive prior
authorization by the Department of Health.
In practice, the Council of Europe and
FEMA lists of approved flavoring sub-
stances are used as the basis of assessment
and acceptance.
The use of flavorings in any product must
be declared on the label using the term "mit
Aroma."
Natural flavorings may be reinforced up
to a maximum of 5% of added artificial
flavorants and still be considered as
"natural."
Legislation
Lebensmittelverordnung dated May 25,
1936, as amended.
UNITED KINGDOM (GREAT
BRITAIN)
Currently, there are no specific regulations
governing the use of flavoring materials in
foods. The Food and Drugs Act, 1955,
prohibits the use in food of any substances
injurious to health and regulates the sale of
any foodstuff which is not of the nature,
substance or quality purported to the pur-
chaser. This legislation is supported by the
Labelling of Food Regulations and numer-
ous other regulations specific to food addi-
tives and/or product groups.
In 1965, the Food Standards Committee
of the Ministry of Agriculture, Fisheries and
Food made its report on flavoring agents
after reviewing the problems associated with
the control of flavor usage. The committee
recommended that future legislation should
consist of a negative list prohibiting the
use in food of 16 flavoring agents the
pharmacological properties and probable
toxicity of which had been established. All
other flavoring materials presently in use
would continue to be acceptable. In 1966, a
joint statement was issued by the Ministry of
Agriculture, Fisheries and Food and the
Ministry of Health and the Home Office
accepting these recommendations only as a
guide to manufacturers and, at the same
time, expressing the opinion that the most
effective control of flavoring agents was by
means of a permitted list having a sound
scientific basis of toxicological data and
safety in use.
Subsequently, the Food Additives and
Contaminants Committee (FACC) of the
Ministry of Agriculture, Fisheries and Food,
studied the problem and issued its com-
prehensive report on the review of flavor-
ings in food (1976). This recommends that
future legislation in the United Kingdom
should be based on the following: (a)
Flavorings, whether natural, synthetic (i.e.,
nature-identical), or artificial should be
controlled by permitted lists. (b) No flavor-
ings should be authorized for use without
being included in the published permitted
lists. (c) The term "flavoring" should be
used in all regulations made under the Food
and Drugs Act to describe the class of food
additives and the substances within the
group. (d) Flavoring regulations should
control herbs and spices as well as naturally
occurring consituents of natural food sub-
stances (not themselves being natural food
substances) when they are used as flavorings
in their own right. The legislation should
exempt from control natural food sub-
stances, naturally occurring substances
present in a food as a result of using a
natural food substance, substances present

in food as a result of changes which have
already taken place during its preparation,
and food additives already controlled under
other regulations.
The report then lists those flavorings
which it recommends should be included in
the permitted lists under the following
headings:
App. 1. Natural flavouring substances
which are or are derived from natural con-
stituents of food such as edible fruits and
nuts.
App. 2. Natural flavouring substances
consisting of or derived from vegetables,
herbs or spices to be used in small quantities
as additions to foods provided that they
are not used in amounts exceeding those
occurring naturally in foods.
App. 3. Natural flavouring substances
which are used at present but which are not
widely consumed foodstuffs, herbs or
spices.
App. 4. Flavouring substances for which
the available evidence suggests possible
toxicity and which accordingly ought not to
be allowed in food. This appendix includes
13 natural products.
App. 5. Artificial and synthetic flavour-
ing substances that the available evidence
suggests are acceptable for use in food,
subject to limits of concentrations stated,
namely:
(i) No limit-good manufacturing prac-
tice.
(ii) Technological level in food acceptable
as a flavoring.
(iii) Limit in food not to be exceeded on
technological or toxicological grounds.
This appendix lists 744 chemicals.
These recommendations have yet to be
translated into legislation. Burke (1976) has
critically examined and questions the need
and practicality of these recommendations
as the basis of workable legislation. The
difficulty of enforcing such a positive list is
obvious and authorities would have to rely
International Flavor Legislation 891
to a large extent on the integrity of the
flavor manufacturer for compliance just as
they do at the present.
Legislation
The Food and Drugs Act, ·1955, as
amended.
The Labelling of Food Regulations, 1970
(Statutory Instrument 1970, No. 400 as
amended by Statutory Instrument, 1972,
No. 1510).
References
Food Standards Committee Report on
Flavouring Agents, Her Majesty's Sta-
tionery Office, London, 1965.
Food Additives and Contaminants
Committee Report on the Review of
Flavourings in Food. Her Majesty's Sta-
tionery Office, London, 1976.
UNITED STATES OF AMERICA
The United States has always been in the
forefront of legislation aimed at the well-
being of its people. The first federal legis-
lation governing food and drugs was the
Food and Drug Law of 1906. This was a
relatively simple piece of legislation aimed
at controlling misrepresentation, limiting
the use of a number of chemicals and estab-
lishing hygiene requirements for food
processors. This act was replaced by the
Federal Drug and Cosmetic Act, 1938. This
is still the basic legislation but new pro-
visions to meet the requirements of better
consumer protection were incorporated by
the Food Additives Amendment, 1958.
These amendments had a three-fold
purpose: (a) protection of the public health
by requiring proof of safety in use of any
food additive, (b) regulation of the safe use
in foods of substances deemed techno-
logically necessary to improve the food
supply, and (c) the forbidding for use in
food of any substance in any amount what-
ever which is found to induce cancer when
ingested by man or animal (the Delaney
892 Source Book of Flavors
Clause). This latter clause is currently under
criticism as being too restrictive and over-
protective (1978). These amendments were
of considerable importance as they intro-
duced the concept of "generally recognized
as safe" (GRAS) as well as containing the
Delaney Clause, which has resulted in a
tremendous increase in toxicological testing.
Any substance which is "generally re-
cognized among experts qualified by scien-
tific training to evaluate its safety, as having
been adequately shown through scientific
procedure or experience based on common
use in food, to be safe under the conditions
of its intended use" is not subject to restric-
tive control in the same way as are the
defined and permitted food additives. This
concept necessitated the drawing up of lists
of materials which could be classified as
GRAS. In 1960, the Flavor & Extract
Manufacturers Association (FEMA) set up
an Expert Panel which was given the task of
accumulating data on the usage of flavoring
materials. As a result of this survey, the
Expert Panel drew up a list of about 1100
chemicals and natural flavoring substances
which were then in use in the United States,
classifying them into the following categories
(Hall 1960): (a) no further action (NFA),
(b) foods, (c) generally recognized as safe
(GRAS), and (d) food additives. The basic
biochemical and toxicological criteria used
in the assessment of safety-in-use of flavor
chemicals has been reviewed by Gerarde
(1973) and this topic is further discussed in
the section, Toxicology and Consumer
Safety. This initial classification certainly
helped to clarify the available use data and
collate such information as was available on
toxicity. However, it resulted in some dis-
agreement on the onus of responsibility for
deciding the precise classification of flavor-
ing substances for legislative purposes.
Between 1958 and 1962, the Food and Drug
Administration (FDA) also compiled lists of
natural and artificial flavoring materials
based on available toxicological data and in
1966 these were accepted as "safe under
specified conditions of use." In 1971, the
FDA announced that it would be the sole
judge of what substances are to be classified
as GRAS and this decision has resulted in
considerable dissent, particularly on what is
to be the basis for such judgment (Stofberg
1978). Many of the FDA GRAS substances
are also included in the FEMA GRAS list
but the two lists do differ in detail. Those
accepted under the food and drugs legis-
lation were included under sections CFR
121.1163 for natural materials and 121.1164
for synthetic chemicals but these sections
have recently been revised and renumbered
as sections 172.510 and 172.515, respec-
tively (BIBRA 1977). The FDA published
the criteria used in assessing a chemical for
inclusion in the GRAS list in the Federal
Register dated June 25, 1971. This brings
into line the acceptance of flavoring ma-
terials and other food additives in spite of
many dissimilarities in use levels, etc. The
term GRAS with respect to flavorings has
acquired a special connotation involving a
low priority for their detailed toxicological
evaluation and their acceptance for use in
foods at levels within the normal tech-
nological needs and sensory requirements of
the product.
Both FDA and FEMA recognize that
there is a considerable degree of over-
lapping in their activities in the field of
toxicological evaluation and safety assess-
ment. Even though the basis for acceptance
is apparently different, the lists are under
review by both organizations with the aim of
producing a single GRAS list of all flavoring
materials which are permitted as safe for use
in foods under good manufacturing practice.
The progress of these deliberations under
the Food Additives Amendment legislation
is likely to be slow. The GRAS classifica-
tions accepted by FEMA have been pub-
lished in a series of lists (No. 1 to 15) by Hall
(1960), Hall and Oser (1961,1965,1968,
1970), Oser and Hall (1972), Oser and Ford
(1973,1974,1975,1977 ,1978,1979), Oser,
Ford, and Bernard (1984), Oser, Weil,
Woods, and Bernard (1985), and Burdock,
Wagner, Smith, Munro, and Newberne

(1990). This work is progressive and later
lists are expected. The current legislation
with regard to flavorings in the United States
has been thoroughly reviewed by Lenane
(1977,1978). Regular update articles appear
monthly in Food Technology and Inter-
national Flavours and Food Additives.
Announcements of specific legislation and
amendments are published regularly in the
BIBRA Information Bulletin.
Flavor legislation in the United States
is very involved and the use of flavoring
materials may be restricted by other food
additive regulations, by defined food stan-
dards, and in certain nonstandardized food
products and commodities. In the next
section will be found details of U.S. De-
finitions and Standards Under the Federal
Food, Drug & Cosmetic Act.
The following flavoring substances are
specifically prohibited for use in foods:
calamus oil, coumarin and safrole.
Legislation
Federal Food, Drug and Cosmetic Act,
1938, as amended by the Food Additives
Amendment, 1958.
Code of Federal Regulations, Title 21, as
amended 1977.
YUGOSLAVIA
All foodstuffs which include substances
which are regarded as biologically active
(including vitamins, mineral salts, colorants,
preservatives, antioxidants, etc.) require
prior registration and authorization by the
Sanitary Inspectorate of the Republic.
Regulations permit the use of artificial
flavoring preparations in sugar confec-
tionery and cakes. There is a negative list of
prohibited flavoring materials (which is the
same as that enforced in Germany plus
coumarin).
Legislation
Yugoslav Law No. 157 (1957)-Sanitary
Control of Foodstuffs. Reference: Receil
International Flavor Legislation 893
International de Legislations Sanitaires, 8,
520.
Yugoslav Regulation . dated May 16,
1963. Reference: Current Food Aoditives
Legislation (1964), No. 71, 953.
References: International Flavor
Legislation
The BIBRA issues Information Bulletins
which contain regular sections on current
development in food legislation by coun-
tries. Contact British Industrial Biological
Research Association, Woodmansterne
Rd., Carshalton, Surrey, SM5 4DS, United
Kingdom.
Also, FAO of the United Nations issues
Food Additive Control Series, a series of
booklets dealing with food additive legis-
lation in specific countries. Write Food and
Agriculture Organization, United Nations,
Rome, Italy.
Alfano, M.C. 1980. Nutrition, sweeteners and
dental caries. Food Techno!. 34(1):70-74.
Amoore, J.E. 1976. Synthetic flavors-a new
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Anon. 1961. Food Additives, What They Are
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Manufacturing Chemists Association, 1825
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Anon. 1970. Changes in food regulations. Food
Techno!. Austr. 22:630-631, 633, 635.
Anon. 1971a. Flavour legislation-the present
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Anon. 1971b. International flavour legislation.
Flavour Ind. 2:265.
Anon. 1974a. Basic features of modern flavour
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Anon. 1974b. Natural flavor added to F.F. may
be legally "artificial." Quick Frozen Foods
36(8), 38-39.
Anon. 1975a. Evolution of controls. Int.
Flavours Food Additives 6(2), Editorial.
Anon. 1975b. Cocoa and chocolate products.
Proposed regulations. Int. Flavours Food
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Anon. 1976a. Report on the 2nd symposium of
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Flavours; safety and regulations. Perfum.
Flavorist 1(4):1-19.
894 Source Book of Flavors
Anon. 1976b. Flavorings in food-a report of
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Anon. 1977a. U.S. cold front over Britain. Int.
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Anon. 1977b. Basic features of modern flavour
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Anon. 1979. FDA's Miller doubts risk/benefit
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Barros, C. 1978. The food legislation situation in
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Blede, E.E. 1973. Food regulations in Latin
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Burdock, G.A., Wagner, B.M., Smith, R.L.,
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44(2):78.
Council of Europe. 1974. Natural Flavouring
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Fritzsche Brothers, Inc. 1966. Guide to flavoring
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223-230.
Haigh, R. 1978. Harmonization of legislation on
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Working procedures. J. Food Techno!.
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Hall, R.L. 1960. Recent progress in the con-
sideration of flavoring ingredients under the
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14(10):488.
Hall, R.L. 1968. Flavor and flavoring: Seeking a
concensus of definition. Food Techno!.
22(11):162.
Hall, R.L. 1975. GRAS-concept and applica-
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Hall, R.L. and Oser, B.L. (then Oser, B.L. and
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19(2), part 2, 151. No. 4. GRAS substances.
Ibid. 24(5):25-34. No. 5. GRAS substances.
Ibid. 26(5):35-37. No. 6. GRAS substances.
Ibid. 27(1):64-67. No. 7. GRAS substances.
Ibid. 27(11):56-57. No. 8. GRAS substances.
Ibid. 28(9):76-80. No. 9. GRAS substances.
Ibid. 29(8):70-72. No. 10. GRAS substances.
Ibid. 31(1):65-74. No. 11. GRAS substances.
Ibid. 32(2):60-70. No. 12. GRAS substances.
Ibid. 33(7):65-73.
Hallstrom, C.H. et al. 1978. A food scientist's
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Hanold, T. 1976. What causes strained relations
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Iofi. 1976. Basic Features of Modern Flavour

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Knights, J. 1975. Legislation causes difficulties.
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Liberman, A. 1979. The European patents-its
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McCormick, R.D. 1979. The flavor report-
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International Flavor Legislation 895
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Miller, S.A. 1979. A prototype for biological
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Roberts, W. 1978. Food law and its enforcement.
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896 Source Book of Flavors
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9(2):77-79, 85.
Ward, A.G. 1979. Innovation in food, the
consumer and the law. Food Technol. Aust.
31(10):422-425.
Weisberg, S.M. 1974. Food acceptance and
flavor requirements in the developing world.
Food Technol. 27(11):48, 50-52.
Wells, W.G., Jr. and Ostenso, G.L. 1980.
Applying science and technology in the
political decision-making process. Food
Technol. 34(1):81-83.
Wendt, A.S. (Ongoing Current Dates) News
from America-a regular feature article
dealing with aspects of current legislation
in the U.S.A. as affecting flavorings. Int.
Flavours Food Additives.
Wendt, A.S. 1975. Joint FAO/WHO Committee
Reports. Int. Flavours Food Additives
6(2):95-98, 102.
Wendt, A.S. 1976. FEMA annual convention-a
report. Int. Flavours Food Additives 7(4):
155-157.
Wodicka, V.O. 1974. Regulatory problems with
flavours. Flavour Ind. 5:293-294, 298.
Wodicka, V.O. 1977. Quality assurance and the
government-understanding the dialogue.
Food Technol. 31(10):20, 22, 24, 28.
EUROPEAN ECONOMIC
COMMUNITY FLAVOR-RELATED
ACTIVITIES
The European Economic Community
(EEC) currently comprises twelve coun-
tries, namely: Belgium, Denmark, France,
Germany, Greece, Ireland, Italy, Luxem-
burg, The Netherlands, Portugal, Spain,
United Kingdom. Legislation within the
Community is the responsibility of the in-
dividual national governments.
One must appreciate the complexity of
developing food legislation within the
European Community (EC) Member states
in Europe. We are looking at tremendous
differences in cultures, philosophies, social
systems, tastes and traditions, not to men-
tion the many languages. They all must be
factored into the harmonization of food
regulations. Yet by the end of 1992 we can
look toward a reasonable completion of this
harmonization process in Europe. The
concept of harmonization addresses the
following needs:
• To protect public health.
• To provide consumers with information
and protection in matters other than
health.
• To ensure fair trading.
• To provide for necessary public controls.
Briefly to the Harmonization Process:
Legislation can only be initiated with a
proposal from the EC Commission. This
proposal is being sent to the Council and the
 International Flavor Legislation 897

Drawing Up EEC Food Legislation

Commission
Presents Draft Directive
to Council

Council
Examines, Approves Eurapean Parliament
Passes Draft to Supervises Commission
Directive (Unanimous), European Parliament
then Promulgates and Council;
for Opinion Advises, Passes
Legislation
(Regulation or Diredive)

Regulation (Agricultural Produds) is binding, has dired

force of law in Member State

Diredive is binding on Member State as to intention and

State implements in its own way

FIGURE 23-1. Implementation of EEC food legislation.

European Parliament. The Parliament reads Authorizes marketing of flavors in com-

the proposal for the first time, gives its
advice, and the Council reaches a common
position. The common position is returned
to Parliament for further consideration. If
the European Parliament adopts the com-
mon position of the Council, a final decision
is reached. The three partners who bring
about harmonization are, therefore, the
European Parliament, the Commission, and
the Council. (See Fig. 23-1.)
1. COUNCIL DIRECTIVE OF
JUNE 22, 1988
"On the approximation of the laws of the
Member States relating to flavorings for
use in foodstuffs, and to source materials
for their production." (88/388/EEC)
Directive defines flavoring components used
in the manufacture of food flavors, and
how the bulk flavor container must be
labeled on the front label and the in-
gredient listing.
Prescribes how to convey the classes of
ingredients in a flavor to the food
manufacturer.
pliance by June 22, 1990.
Prohibits marketing of flavors not in com-
pliance by June 22, 1991.
This development is of importance also to
the United States manufacturer of flavors
and food products intended for sale in the
EC, since Article Eleven states: "This
Directive shall also apply to flavoring
intended for use in foodstuffs, and to food-
stuffs imported into the Community."
Under this Council Directive on the same
date, a Council Decision had been issued to
establish, within 24 months, an inventory of
all possible ingredients, including sources
used for the manufacture of flavors.
2. COMMISSION DIRECTIVE OF
JANUARY 16, 1991
"Completing Council Directive 88/388/EEC
on the approximation of the laws of the
Member States relating to flavorings for
use in foodstuffs, and to source materials
for their production." (91/71/EEC)
898 Source Book of Flavors

Directive applies to the labeling of flavors Permits trade of products in compliance by

for sale to the final consumer. (Flavor
Extracts)
Permits trade of product in compliance by
June 30, 1992.
Prohibits trade of products not in com-
pliance by January 1, 1994.
3. COMMISSION DIRECTIVE OF
JANUARY 16, 1991
"Amending Council Directive 79/112/EEC
in respect of the designation of flavorings
in the list of ingredients on the labels of
foodstuffs." (91/72/EEC)
Directive applies to the flavor portion of the
ingredient label on the food product.
June 30, 1992.
Prohibits trade of products not in com-
pliance by January 1, 1994.
Council Directive 79/112/EEC had been the
first document on the labeling, presentation
and advertising of foodstuffs for the sale to
the ultimate consumer. Flavor labeling was
not addressed at that time.
Food Labeling on front panel must still
be decided upon.
Each country must ratify the Directives
and this process has been rather slow.
Now to the term "Nature-Identical" as it
is being applied in Europe: Nature-Identical
means a chemical identified in nature pre-

TABLE 23-3. Non-Nature-Identical Ingredients in Germany and Italy-a Comparison

Maximum permissible quantity in finished product,

expressed in ppm.

FEMANumber Ingredient Germany Italy

2385 m-Dimethoxy Benzene 5 1.0 hard candy

2464 Ethyl Vanillin 250 50-90 various most 200
2583 Hydroxycitronellal ---------- 0.5-2.5
2584 Hydroxycitronellal total of 25 calculated as
Diethyl Acetal ------------ Hydroxycitronellal not permitted
2585 Hydroxycitronellal
Dimethyl Acetal ---------- not permitted
2723 Methyl-Beta-Naphthyl Ketone 5 0.2 hard candy
2922 Propenylguaethol 25 0.1-0.2 various
2038 Allyl Phenoxy Acetate 2 not permitted
2061 alpha-Amylcinnamaldehyde 1 not permitted
3487 Ethyl Maltol (Flavor Enhancer, 50 not permitted
Additive)
2672 4-(p-Methoxyphenyl)-2-Butanone 25 not permitted
2699 6-Methylcoumarine 30 not permitted
2729 Methyl-2-0ctynoate 4 not permitted
2886 2-Phenylpropionaldehyde 1 not permitted
2913 Piperonyl Isobutyrate 3 not permitted
3108 Vanillin Acetate 25 not permitted
2026 Allyl Cyclohexylpropionate not permitted 1.0-2.0 various
2444 Ethyl Methyl Phenyl Glycidate not permitted 5-100 various
2711 Methyl-Alpha-Ionone not permitted 0.25 various
2768 Beta-Naphthyl Ethyl Ether not permitted 1.0 liqueur, hard candy
Ingredients recently identified as nature-identical
2415 Ethyl Aceto Acetate permitted 2.0various
2032 Allyl Hexanoate permitted 2.0 hard candy
2781 Gamma Nonalactone permitted 0.5-1.0 various
3091 Gamma Undecalactone permitted 5-10 various
 International Flavor Legislation 899

Bulk Flavor Bulk Flavor

Flavor consisting of nature identical alone
Natural flavor, derived almost solely from
or nature identical and permitted non-nature
the foodstuff or the flavoring source
identical ingredients.
concerned, described such as Strawberry.
e.g. a Strawberry flavor:

"r----~ ..
v
Finished Food Finished Food

lttgredientt:
FICJYoring tH'
lngtedi•nts; S.tr awb.rwy
Attvoring or Flovoring or

s;~=::;,;v a._ '\ Notu~~;=~!!"t ...

FIGURE 23-2. Resulting ingredient listing of a FIGURE 23-4. Resulting ingredient listing of a
nature-identical flavor added to food. completely natural flavor added to food.

Bulk Flavor The United States permits the use of

Natural flavor, containing flavoring
preparation and/or natural flavoring
substances.
more than 400 of such non-nature-identical
ingredients. This is one of the most difficult
issues on which to achieve harmonization .
The ingredient labeling requirements for
flavored products in Europe will be rather
straightforward , as the following pictures

l "' " demonstrate . (See Figures 23-2-23-4.)

..
Finished Food

Stn~~"1
1)'JK flaH)t ,
NaiU ral
J The Directive describes five flavoring
categories which must be listed in descend-
Ingredient$:
Flowering or ing order by weight when describing the
Strowb4""
'\ Na~~~;~'~:.=;rl9 ... ingredients of a flavoring preparation.
Ingredients which do not fit into either
FIGURE 23-3. Resulting ingredient listing of a category must be identified by name or their
natural flavor plus natural flavoring substances added EEC numbers.
to food .

1. Natural Flavoring Substances-Single

pared by synthesis. Artificial means a natural chemical; examples are Citral,
non-nature-identical ingredient. Certain Benzaldehyde , Eugenol.
countries in Europe presently permit only a 2. Nature-Identical Flavoring Substances
very limited number of such non-nature- 3. Artificial (Non-Nature-Identical) Flavor-
identical ingredients. (See Table 23-3.) ing Preparations-Examples: Pepper
The Netherlands and Spain have a rather Extract, Apple Essence
comprehensive list of non-nature-identical 4. Processed Flavorings
ingredients. 5. Smoke Flavorings
Council
Council Directive
of 18 December 1978
on the approximation of the laws of the
Member States relating to the labelling,
(79/112/EEC)
THE COUNCIL OF THE EUROPEAN
COMMUNITIES
Having regard to the Treaty establishing the
European Economic Community, and in par-
ticular Articles 100 and 227 thereof,
Having regard to the proposal from the
Commission 1 ,
Having regard to the opinion of the European
Parliament2 ,
Having regard to the opinion of the Economic
and Social Committee3 ,
Whereas differences which exist at present
between the laws, regulations and administraive
provisions of Member States on the labelling of
foodstuffs impede the free circulation of these
products and can lead to unequal conditions of
competition;
Whereas, therefore, approximation of these laws
1 OJ No C. 91.22.4. 1976. p. 3.
2 01 No C. 178.2.8. 1976. p. 52.
3 01 No C. 285.2.12. 1976. p. 3.
presentation and advertising of foodstuffs
for sale to the ultimate consumer
would contribute to the smooth functioning of
the common market;
Whereas the purpose of this Directive should be
to enact Community rules of a general nature
applicable horizontally to all foodstuffs put on
the market;
Whereas rules of a specific nature which apply
vertically only to particular foodstuffs should
be laid down in provisions dealing with those
products;
Whereas, moreover, the field of application of
this Directive should be limited to foodstuffs
intended for sale to the ultimate consumer, and
the rules governing the labelling of products
intended for subsequent processing or prep-
aration should be fixed at a later stage;
Whereas the prime consideration for any rules on
the labelling of foodstuffs should be the need to
inform and protect the consumer;
Whereas, therefore, a list should be drawn up of
all information which should in principle be
included in the labelling of all foodstuffs;
901
902 Council
Whereas, however, the horizontal nature of this
Directive does not allow, at the initial stage, the
inclusion in the compulsory indications of all
the indications which must be added to the list
applying in principle to the whole range of
foodstuffs; whereas, during the second stage,
Community provisions should be adopted, aimed
at supplementing the existing rules; whereas
it would accordingly seem necessary to adopt
as a matter of priority Community provisions
regarding the indication of certain ingredients in
the sales description or by indicating a quantity;
Whereas, furthermore, if in the absence of
Community rules of a specific nature Member
States should retain the right to lay down certain
national provisions which may be added to the
general provisions of this Directive, nevertheless
these provisions should be subject to a Com-
munity procedure;
Whereas the said Community procedure may
consist simply in informing the Commission and
the Member States when the matter concerns the
maintenance of national provisions that precede
this Directive, but must be that of a Community
Decision when a Member State wishes to enact
new legislation;
Whereas provision should also be made for the
Community legislator to derogate, in exceptional
cases, from certain obligations that have been
fixed generally;
Whereas the rules on labelling should also pro-
hibit the use of information that would mislead
the purchaser or attribute medicinal properties
to foodstuffs; whereas, to be effective, this
prohibition should also apply to the presentation
and advertising of foodstuffs;
Whereas Member States should retain the right,
depending on local conditions and circumstances,
to lay down rules in respect of the labelling of
foodstuffs sold in bulk; whereas, in such cases,
information should nevertheless be provided for
the consumer;
Whereas, with the aim of simplifying and
accelerating the procedure, the Commission
should be entrusted with the task of adopting
implementing measures of a technical nature;
Whereas in all cases where the Council makes the
Commission responsible for implementing rules
laid down in respect of foodstuffs, provision
should be made for a procedure instituting close
cooperation between Member States and the
Commission within the Standing Committee on
Foodstuffs, set up by Decision 69/414/EEC\
Whereas foodstuffs in Greenland are manu-
factured and marketed under conditions funda-
mentally different from those prevailing in the
other parts of the Community because of the
island's general situation and, in particular,
because of its commercial structures, low popu-
lation, considerable area and special geographical
situation,
HAS ADOPTED THIS DIRECTIVE
Article I
1. This Directive concerns the labelling of food-
stuffs to be delivered as such to the ultimate
consumer and certain aspects relating to the
presentation and advertising thereof.
2. Without prejudice to the Community pro-
visions to be adopted in this field, this Directive
shall apply also to foodstuffs intended for supply
to restaurants, hospitals, canteens and other
similar mass caterers, in so far as the Member
States shall so decide.
3. For the purpose of this Directive,
(a) "labelling" shall mean any words, par-
ticulars, trade marks, brand name, pictorial
matter or symbol relat ng to a foodstuff and
placed on any packaging, document, notice,
label, ring or collar accompanying or refer-
ring to such foodstuff;
(b) "pre-packaged foodstuff" shall mean any
single item for presentation as such to the
ultimate consumer, consisting of a foodstuff
and the packaging into which it was put
before being offered for sale, whether such
packaging encloses the foodstuff completely
or only partially, but in any case in such a
way that the contents cannot be altered
without opening or changing the packaging.
Article 2
1. The labelling and methods used must not:
(a) be such as could mislead the purchaser to a
material degree, particularly:
1 01 No I. 291.29.11. 1969, p. 9.

(i) as to the characteristics of the foodstuff
and, in particular, as to its nature,
identity, properties, composition,
quantity, durability, origin or prove-
nance, method of manufacture or
production,
(ii) by attributing to the foodstuff effects or
properties which it does not possess,
(iii) by suggesting that the foodstuff
possesses special characteristics when
in fact all similar foodstuffs possess
such characteristics;
(b) subject to the provisions applicable to
foodstuffs for particular nutritional uses,
attribute to any foodstuff the property of
preventing, treating or curing a human
disease, or refer to such properties; Com-
munity provisions or, where there are none,
national provisions may derogate from this
rule in the case of natural mineral waters.
The procedure laid down in Article 16 shall
apply to any such national provisions.
2. The Council, in accordance with the pro-
cedure laid down in Article 100 of the Treaty,
shall draw up a non-exhaustive list of the claims
within the meaning of paragraph 1, the use
of which must at all events be prohibited or
restricted.
3. The prohibitions or restrictions referred to in
paragraphs 1 and 2 shall also apply to:
(a) the presentation of foodstuffs, in particular
their shape, appearance or packaging, the
packaging materials used, the way in which
they are arranged and the setting in which
they are displayed:
(b) advertising.
Article 3
1. In accordance with Articles 4 to 14 and
subject to the exceptions contained therein,
indication of the following particulars alone shall
be compulsory on the labelling of foodstuffs:
(1) the name under which the product is sold,
(2) the list of ingredients,
(3) in the case of prepackaged foodstuffs, the
net quantity,
(4) the date of minimum durability,
Council 903
(5) any special storage conditions or conditions
of use,
(6) the name or business name and address of
the manufacturer or packager, or of a seller
established within the Community.
However, the Member States shall be
authorized, in respect of butter produced in
their territory, to require only an indication
of the manufacturer, packager or seller,
Without prejudice to the notification pro-
vided for in Article 22, Member States shall
inform the Commission and the other
Member States of any measure taken
pursuant to this paragraph,
(7) particulars of the place of origin or prove-
nance in the cases where failure to give such
particulars might mislead the consumer to a
material degree as to the true origin or
provenance of the foodstuff,
(8) instructions for use when it would be im-
possible to make appropriate use of the
foodstuff in the absence of such instructions.
2. Notwithstanding the previous paragraph,
Member States may retain national provisions
which require indication of the factory or pack-
aging centre, in respect of home production.
3. The provisions of this Article shall be without
prejudice to more precise or more extensive
provisions regarding weights and measures.
Article 4
1. Community provisions applicable to specified
foodstuffs and not to foodstuffs in general may
provide for derogations, in exceptional cases,
from the requirements laid down in Article 3 (1),
points 2 and 4, provided that this does not result
in the purchaser being inadequately informed.
2. Community provisions applicable to specified
foodstuffs and not to foodstuffs in general may
provide that other particulars in addition to those
listed in Article 3 must appear on the labelling.
Where there are no Community provisions,
Member States may make provision for such
particulars in accordance with the procedure laid
down in Article 16.
Article 5
1. The name under which a foodstuff is sold shall
be the name laid down by whatever Jaws, regu-
904 Council
lations or administrative provisions apply to the
foodstuff in question or, in the absence of any
such name, the name customary in the Member
State where the product is sold to the ultimate
consumer, or a description of the foodstuff and,
if necessary, of its use, that is sufficiently precise
to inform the purchaser of its true nature and to
enable it to be distinguished from products with
which it could be confused.
2. No trade mark, brand name or fancy name
may be substituted for the name under which the
product is sold.
3. The name under which the product is sold
shall include or be accompanied by particulars as
to the physical condition of the foodstuff or the
specific treatment which it has undergone (e.g.
powdered, freeze-dried, deep-frozen, concen-
trated, smoked) in all cases where omission of
such information could create confusion in the
mind of the purchaser.
Article 6
1. Ingredients shall be listed in accordance with
this Article and the Annexes.
2. Ingredients need not be listed in the case of:
(a) - fresh fruit and vegetables, including
potatoes, which have not been peeled,
cut or similarly treated,
carbonated water, the description
of which indicates that it has been
carbonated,
fermentation vinegars derived exclu-
sively from a single basic product, pro-
vided that no other ingredient has been
added;
(b) cheese,
butter,
fermented milk and cream,
provided that no ingredient has been added
other than lactic products, enzymes and
micro-organism cultures essential to manu-
facture, or the salt needed for the manufac-
ture of cheese other than fresh cheese and
processed cheese;
(c) products consisting of a single ingredient.
3. In the case of beverages containing more than
1.2% by volume of alcohol, the Council, acting
on a proposal from the Commission, shall, before
the expiration of a period of four years following
notification of this Directive, determine the rules
for labelling ingredients and, possibly, indicating
the alcoholic strength.
4. (a) "Ingredient" shall mean any substance,
including additives, used in the manu-
facture or preparation of a foodstuff and
still present in the finished product, even
if in a'tered form.
(b) Where an ingredient of the foodstuff is
itself the product of several ingredients,
the latter shall be regarded as ingredients
of the foodstuff in question.
(c) The following shall not be regarded as
ingredients:
(i) the constituents of an ingredient
which have been temporarily
separated during the manufacturing
process and later reintroduced but
not in excess of their original
proportions;
(ii) additives:
whose presence in a given
foodstuff is solely due to the
fact that they were contained
in one or more ingredients of
that foodstuff, provided that
they serve no technological
function in the finished
product,
which are used as processing
aids;
substances used in the quantities
strictly necessary as solvents
or media for additives or
flavouring.
(d) In certain cases Decisions may be taken
in accordance with the procedure laid
down in Article 17 as to whether the
conditions described in (c) (ii) are
satisfied.
5. (a) The list of ingredients shall include all the
ingredients of the foodstuff, in descend-
ing order of weight, as recorded at the
time of their use in the manufacture of
the foodstuff. It shall appear preceded by
a suitable heading which includes the
word "ingredients".

However:
added water and volatile products
shall be listed in order of their weight
in the finished product: the amount of
water added as an ingredient in a
foodstuff shall be calculated by de-
ducting from the total amount of the
finished product the total amount of
the other ingredients used. This
amount need not be taken into con-
sideration if it does not exceed 5% by
weight of the finished product;
ingredients used in concentrated or
dehydrated form and reconstituted at
the time of manufacture may be listed
in order of weight as recorded before
their concentration or dehydration;
in the case of concentrated or de-
hydrated foods which are intended to
be reconstituted by the addition of
water, the ingredients may be listed
in order of proportion in the recon-
stituted product provided that the list
of ingredients is accompanied by an
expression such as "ingredients of the
reconstituted product", or "ingre-
dients of the ready-to-use product";
in the case of mixtures of fruit or
vegetables where no particular fruit
or vegetable significantly predomi-
nates in proportion by weight, those
ingredients may be listed in another
order provided that the list of in-
gredients is accompanied by an
expression such as "in variable
proportion";
in the case of mixtures of spices or
herbs, where none significantly pre-
dominates in proportion by weight,
those ingredients may be listed in
another order provided that that list
of ingredients is accompanied by an
expression such as "in variable
proportion";
(b) ingredients shall be designated by their
specific name, where applicable, in
accordance with the rules laid down in
Article 5.
However:
Council 905
ingredients which belong to one of
the categories listed in Annex I and
are constituents of another foodstuff
need only be designated by the name
of that category;
ingredients belonging to one of the
categories listed in Annex II must
be designated by the name of that
category, followed by their specific
name or EEC number; if an ingre-
dient belongs to more than one of the
categories, the category appropriate
to the principal function in the case of
the foodstuff in question shall be
indicated; amendments to this Annex
based on advances in scientific and
technical knowledge shall be adopted
in accordance with the procedure laid
down in Article 17;
flavouring matter shall be described
in accordance with the national
provisions applicable thereto, until
the entry into force of the Com-
munity provisions;
the Community provisions or, where
there are none, the national pro-
visions applicable to certain specified
foodstuffs, many also provide for
categories additional to those speci-
fied in Annex I. Without prejudice to
the notification provided for in
Article 22, Member States shall
inform the Commission and the other
Member States of any measure taken
pursuant to this indent.
6. Community provisions or, where there are
none, national provisions may lay down that the
name under which a specific foodstuff is sold is to
be accompanied by mention of a particular
ingredient or ingredients.
The procedure laid down in Article 16 shall apply
to any such national provisions.
7. In the case referred to in paragraph 4 (b), a
compound ingredient may be included in the list
of ingredients, under its own designation in so far
as this is laid down by law or established by
custom, in terms of its overall weight, provided
that it is immediately followed by a list of its
ingredients.
Such a list, however, shall not be compulsory:
906 Council
where the compound ingredient constitutes
less than 25% of the finished product;
however, this exemption shall not apply in
the case of additives, subject to the pro-
visions of paragraph 4 (c),
where the compound ingredient is a foodstuff
for which a list of ingredients is not required
under Community rules.
8. Notwithstanding paragraph 5 (a), the water
content need not be specified:
(a) where the water is used during the manu-
facturing process solely for the reconstitu-
tion of an ingredient used in concentrated or
dehydrated form;
(b) in the case of a liquid medium which is not
normally consumed.
Article 7
1. Where the labelling of a foodstuff places
emphasis on the presence or low content of one
or more ingredients which are essential to the
specific properties of the foodstuff, or where the
description of the foodstuff has the same effect,
the minimum or maximum percentage, as the
case may be, used in the manufacture thereof
shall be stated.
This information shall appear either immediately
next to the name under which the foodstuff is
sold or in the list of ingredients in connection
with the ingredient in question.
In accordance with the procedure laid down in
Article 17, it may be decided that, in the case of
certain ingredients, the percentage referred to in
this paragraph shall be expressed in absolute
terms.
2. Paragraph 1 shall not apply:
(a) in the case of labelling which is intended to
characterize a foodstuff in accordance with
Article 5 (1) or which is required under
Community provisions or, where there are
none, under national provisions applicable
to certain foodstuffs;
(b) in the case of ingredients used in small
quantities only as flavourings.
3. Community provisions or, where there are
none, national provisions may stipulate for
certain foodstuffs, as well as in the case referred
to in paragraph 2 (a), that quantities of certain
ingredients must be indicated either in absolute
terms or as percentages and that, where appro-
priate, mention should be made of any alteration
in the quantities of these ingredients.
The procedure laid down in Article 16 shall apply
to any such national provisions.
Article 8
1. The net quantity of prepackaged foodstuffs
shall be expressed:
in units of volume in the case of liquids,
in units of mass in the case of other products,
using the litre, centilitre, millilitre, kilogram or
gram, as appropriate.
Community provisions or, where there are none,
national provisions applicable to certain specified
foodstuffs may derogate from this rule.
The procedure laid down in Article 16 shall apply
to any such national provisions.
2. (a) Where the indication of a certain type
of quantity (e.g. nominal quantity,
minimum quantity, average quantity) is
required by Community provisions or,
where there are none, by national pro-
visions, this quantity shall be regarded as
the net quantity for the purposes of this
Directive.
Without prejudice to the notification
provided for in Article 22, Member
States shall inform the Commission and
the other Member States of any measure
taken pursuant to this point.
(b) Community provisions or, where there
are none, national provisions may, for
certain specified foodstuffs classified by
quantity in categories, require other
indications of quantity.
The procedure laid down in Article
16 shall apply to any such national
provisions.
(c) Where a prepackaged item consists of
two or more individual prepackaged
items containing the same quantity of the
same product, the net quantity shall be
indicated by mentioning the net quantity
contained in each individual package and
the total number of such packages.

Indication of these particulars shall not,
however, be compulsory where the total
number of individual packages can be
clearly seen and easily counted from the
outside and where at least one indication
of the net quantity contained in each
individual package can be clearly seen
from the outside.
(d) Where a prepackaged item consists of
two or more individual packages which
are not regarded as units of sale, the net
quantity shall be given by indicating the
total net quantity and the total number of
individual packages. Community pro-
visions or, where there are none, national
provisions need not, in the case of certain
foodstuffs, require indication of the total
number of individual packages.
Without prejudice to the notification
provided for in Article 22, Member
States shall inform the Commission and
the other Member States of any measure
taken pursuant to this point.
3. In the case of foodstuffs normally sold by
number, Member States need not require indica-
tion of the net quantity provided that the number
of items can clearly be seen and easily counted
from the outside or, if not, is indicated on the
labelling.
Without prejudice to the notification provided
for in Article 22, Member States shall inform the
Commission and the other Member States of any
measure taken pursuant to this paragraph.
4. Where a solid foodstuff is presented in a liquid
medium, the drained net weight of the foodstuff
shall also be indicated on the labelling.
For the purposes of this paragraph, "liquid
medium" shall mean the following products,
possibly in mixtures, provided that the liquid is
merely an adjunct to the essential elements of
that preparation and is thus not a decisive factor
for the purchase: water, salt water, brine,
vinegar, aqueous solutions of sugars, and fruit or
vegetable juices in the case of tinned fruit or
vegetables.
Methods of checking the drained net weight shall
be determined in accordance with the procedure
laid down in Article 17.
5. It shall not be compulsory to indicate the net
quantity in the case of foodstuffs:
Council 907
(a) which are subject to considerable losses in
their volume or mass and which are sold by
number or weighed in the presence of the
purchaser;
(b) the net quantity of which is less than 5 g or
5 ml; however, this provision shall not apply
to spices and herbs.
Community provisions or, where there are none,
national provisions applicable to specified food-
stuffs may in exceptional cases lay down thresh-
olds which are higher than 5 g or 5 ml provided
that this does not result in the purchaser being
inadequately informed.
Without prejudice to the notification provided
for in Article 22, Member States shall inform the
Commission and the other Member States of any
measure taken pursuant to this paragraph.
6. Until the end of the transitional period during
which the use of the imperial units of measure-
ment contained in Chapter D of the Annex to
Directive 71 354/EEC of 18 October 1971 on the
approximation of the laws of the Member States
relating to units of measurement 1 , as last
amended by Directive 76 770/EEC2 , is author-
ized in the Community, Ireland and the United
Kingdom may permit the quantity to be ex-
pressed only in imperial units of measurement
calculated on the basis of the following con-
version rates:
1 ml-0.0352 fluid ounces,
11-1.760 pints or 0.220 gallons,
1 g-0.0353 ounces (avoirdupois),
1 kg-2.205 pounds.
Article 9
1. The date of minimum durability of a foodstuff
shall be the date until which the foodstuff retains
its specific properties when properly stored.
It shall be indicated in accordance with the pro-
visions of this Article.
2. The date shall be preceded by the words:
"Best before ... " when the date includes an
indication of the day,
"Best before end ... " in other cases.
1 01 No 1. 243,29. 10. 1971, p. 29.
2 01 No 1. 262, 27. 9. 1976, p. 204.
908 Council
However, in the case of certain foodstuffs which,
from the microbiological point of view, are highly
perishable, Member States may require the
words "use before: ... " to be indicated. Without
prejudice to the notification provided for in
Article 22, Member States shall inform the
Commission and the other Member States of any
measure taken pursuant to this subparagraph.
Before the expiry of a period of six years from
the date of notification of this Directive, the
Council, acting on a proposal from the Commis-
sion, shall decide on the common date-indication
arrangements for highly perishable foodstuffs
of the sort referred to in the second sub-
paragraph.
3. The words referred to in paragraph 2 shall be
accompanied by:
either the date itself, or
a reference to where the date is given on the
labelling.
If need be, these particulars shall be followed by
a description of the storage conditions which
must be observed if the product is to keep for the
specified period.
4. The date shall consist of the day, month and
year in uncoded chronological form.
However, in the case of foodstuffs:
which will not keep for more than three
months, an indication of the day and the
month will suffice.
which will keep for more than three months
but not more than 18 months, an indication
of the month and year will suffice,
which will keep for more than 18 months, an
indication of the year will suffice.
The manner of indicating the date may be
specified according to the procedure laid down in
Article 17.
5. In their own territories the Member States
may permit the minimum durability period to be
expressed otherwise than in terms of the date of
minimum durability.
Without prejudice to the notification provided
for in Article 22, Member States shall notify the
Commission and the other Member States of any
measure taken under this paragraph.
6. Subject to the Community provisions govern-
ing the products below, an indication of the date
of minimum durability shall not be required for:
fresh fruit and vegetables, including
potatoes, which have not been peeled, cut or
similarly treated,
wines, liqueur wines, sparkling wines,
aromatized wines, fruit wines and sparkling
fruit wines,
beverages containing 10% or more by
volume of alcohol,
bakers' or pastry-cooks' wares which,
given the nature of their content, are nor-
mally consumed within 24 hours of their
manufacture,
vinegar,
cooking salt,
solid sugar,
confectionery products consisting of
flavoured and/or coloured sugars.
Article 10
1. The instructions for use of a foodstuff shall be
indicated in such a way as to enable appropriate
use to be made thereof.
2. Community provisions or, where there are
none, national provisions may, in the case of
certain foodstuffs, specify the way in which the
instructions for use should be indicated.
The procedure laid down in Article 16 shall apply
to such national provisions.
Article 11
1. (a) When the foodstuffs are prepackaged,
the particulars provided for in Article 3
and Article 4 (2) shall appear on the
prepackaging or on a label attached
thereto.
(b) Notwithstanding point (a) and without
prejudice to Community provisions on
nominal amounts, Member States may
authorize that all or some of the par-
ticulars provided for in Article 3 and
Article 4 (2) be given only on the relevant
trade documents when the foodstuffs are
prepackaged and marketed prior to their
sale to the ultimate consumer.

Without prejudice to the notification
provided for in Article 22, Member
States shall inform the Commission and
the other Member States of any measure
taken pursuant to this point.
The Council, acting on a proposal from
the Commission, shall lay down the
provisions to apply subsequently in this
connection not later than nine years after
notification of this Directive.
2. These particulars shall be easy to understand
and marked in a conspicuous place in such a
way as to be easily visible, clearly legible and
indelible.
They shall not in any way be hidden, obscured or
interrupted by other written or pictorial matter.
3. (a) The particulars listed in Article 3 (1),
points 1, 3 and 4, shall appear in the same
field of vision.
This requirement may be extended to the
particulars provided for in Article 4 (2).
(b) However, for glass bottles intended for
re-use, upon which one of the particulars
listed in point (a) is indelibly marked, this
requirement shall not apply for a period
of 10 years following notification of this
Directive.
4. Member States may:
(a) permit that only the particulars listed in
Article 3 (1), points 1, 3 and 4, be indicated
on packaging or containers the largest sur-
face of which has an area of less than 10 cm 2 ,
(b) require the indication of only some of the
particulars listed in Article 3 in respect of
milk or milk products in bottles intended for
re-use; in this case they may also provide for
derogations from paragraph 3 (a).
Without prejudice to the notification provided
for in Article 22, Member States shall inform the
Commission and the other Member States of any
measure taken pursuant to this paragraph.
Article 12
Where foodstuffs are offered for sale to the
ultimate consumer without prepackaging, or
where foodstuffs are packaged on the sales pre-
mises at the consumer's request or prepackaged
for direct sale, the Member States shall adopt
Council 909
detailed rules concerning the manner in which
the particulars specified in Article 3 and Article 4
(2) are to be shown.
They may decide not to require the provision of
all or some of these particulars, provided that the
consumer still receives sufficient information.
Article 13
This Directive shall not affect the provisions of
national laws which, in the absence of Com-
munity provisions impose less stringent require-
ments for the labelling of foodstuffs presented in
fancy packaging such as figurines or souvenirs.
Article 14
Member States shall refrain from laying down
requirements more detailed than those already
contained in Articles 3 to 11 concerning the
manner in which the particulars provided for in
Article 3 and Article 4 (2) are to be shown.
The Member States shall, however, ensure that
the sale of foodstuffs within their own territories
is prohibited if the particulars provided in Article
3 and Article 4 (2) do not appear in a language
easily understood by purchasers, unless other
measures have been taken to ensure that the
purchaser is informed. This provision shall not
prevent such particulars from being indicated in
various languages.
Article 15
1. Member States may not forbid trade in food-
stuffs which comply with the rules laid down
in this Directive by the application of non-
harmonized national provisions governing the
labelling and presentation of certain foodstuffs or
of foodstuffs in general.
2. Paragraph 1 shall not apply to non-
harmonized national provisions justified on
grounds of:
protection of public health,
prevention of fraud, unless such provisions
are liable to impede the application of the
definitions and rules laid down by this
Directive,
protection of industrial and commercial
property rights, indications of provenance,
registered designations of origin and pre-
vention of unfair competition.
910 Council
Article 16
Where reference is made to this Article, the
following procedure shall app
(1) When a Member State maintains the pro-
visions of its national laws, it shall inform the
Commission and the other Member States
thereof within a period of two years after
notification of this Directive;
(2) Should a Member State deem it necessary to
adopt new legislation, it shall notify the
Commission and the other Member States of
the measures envisaged and give the reasons
justifying them. The Commission shall
consult the Member States within the
Standing Committee on Foodstuffs if it con-
siders such consultation to be useful or if a
Member State so requests.
Member States may take such envisaged
measures only three months after such
notification and provided that the Commis-
sion's opinion is not negative.
In the latter event, and before the expiry of
the abovementioned period, the Commis-
sion shall initiate the procedure provided for
in Article 17 in order to determine whether
the envisaged measures may be imple-
mented subject, if necessary, to the appro-
priate modifications.
Article 17
1. Where the procedure laid down in this Article
is invoked, the matter shall be referred to the
Standing Committee on Foodstuffs (hereinafter
called "the Committee") by its chairman, either
on this own initiative or at the request of a
representative of a Member State.
2. The representative of the Commission shall
submit to the Committee a draft of the measures
to be taken. The Committee shall give its opinion
on that draft within a time limit set by the chair-
man having regard to the urgency of the matter.
Opinions shall be delivered by a majority of 41
votes, the votes of the Member States being
weighted as provided for in Article 148 (2) of the
Treaty. The chairman shall not vote.
3. (a) Where the measures envisaged are in
accordance with the opinion of the
Committee, the Commission shall adopt
them.
(b) Where the measures envisaged are not in
accordance with the opinion of the
Committee, or if no opinion is delivered,
the Commission shall without delay
submit to the Council a proposal on the
measures to be taken. The Council shall
act by a qualified majority.
(c) If the Council has not acted within three
months of the proposal being submitted
to it, the proposed measures shall be
adopted by the Commission.
Article 18
Article 17 shall apply for 18 months from the date
on which the matter was first referred to the
Committee pursuant to Article 17.
Article 19
If temporary measures prove necessary to
facilitate the application of this Directive, they
shall be adopted in accordance with the proce-
dure provided for in Article 17.
Article 20
This Directive shall not affect Community pro-
visions relating to the labelling and presentation
of certain foodstuffs already adopted at the time
of its notification.
Any amendments necessary to harmonize such
provisions with the rules laid down in this Direc-
tive shall be decided in accordance with the
procedure applicable to each of the provisions in
question.
Article 21
This Directive shall not apply to products for
export outside the Community.
Article 22
1. Member States shall make such amendments
to their laws as may be necessary to comply with
the provisions of this Directive and shall forth-
with inform the Commission thereof; the laws
thus amended shall be applied in such a way as
to:
permit trade in those products which comply
with the provisions of this Directive no later
than two years after its notification,
 Council 911

prohibit trade in those products which do not the date of minimum durability in the case
comply with the provisions of this Directive of:
four years after its notification.
foodstuffs whose mmtmum durability
2. However, Member States may: exceeds 18 months,
(a) in the case of certain foodstuffs, reduce the deep-frozen foodstuffs,
period specified in the second indent of
ice creams,
paragraph 1;
chewing gums and similar chewing
(b) in the case of certain foodstuffs which keep
products,
for a long time, extend the period specified
in the second indent of paragraph 1; fermented cheese intended to ripen
completely or partially in prepackaging;
(c) without prejudice to the first indent of
Article 23 (1) (b), in the case of foodstuffs (c) the information provided for in Annex I to
which will keep for more than 12 months, supplement the designation "oil" or "fat".
extend to six years the period laid down in
2. Without prejudice to the information
the second indent of paragraph 1 above as
provided for in Article 22, Member States
regards the obligation to indicate the date of
shall inform the Commission and the other
minimum durability.
Member States of any measure taken pursuant to
3. In the case referred to: paragraph 1.
(a) in paragraph 2 (a), the procedure laid down 3. After a period of five years following noti-
in Article 16 (2) shall apply to any national fication of this Directive, the Council shall, in
provision; accordance with the procedure laid down in
Article 100 of the Treaty, decide upon the
(b) in paragraph 2 (b) and (c), Member States
common rules to apply in the cases referred to in
shall inform the Commission and the other
paragraph 1.
Member States of any measure taken
pursuant to the said points.
Article 24
4. Member States shall also ensure that the
This Directive shall also apply to the French
Commission receives the text of any essential
overseas departments.
provision of national law which they adopt in the
field governed by this Directive.
Article 25
This Directive shall not apply to foodstuffs
Article 23 marketed in Greenland, intended for local
consumption.
1. By way of derogation from the second indent
of Article 22 (1), Member States may make
Article 26
implementation of the provisions relating to the
following matters optional: This Directive is addressed to the Member
States.
(a) the designation, provided for in the second
indent of Article 6 (5) (b), of the specific
Done at Brussels, 18 December 1978.
name or EEC number of the ingredients
belonging to one of the categories listed in
For the Council
Annex II;
The President
(b) the indication provided for in Article 9, of J. ERTL
912 Council
ANNEX I
Categories of ingredients which may be
designated by the name of the category
rather than the specific name
Definition
Refined oils other than olive oil.
Refined fats.
Mixtures of flour obtained from two or more
cereal species.
Starches, and starches modified by physical or
enzymatic means.
All species of fish where the fish constitutes an
ingredient of another foodstuff and provided that
the name and presentation of such foodstuff does
not refer to a specific species of fish.
All types of poultrymeat where such meat
constitutes an ingredient of another foodstuff and
provided that the name and presentation of such
a foodstuff does not refer to a specific type of
poultrymeat.
Designation
"Oil", together with
either the adjective "vegetable" or "animal",
as appropriate, or
an indication of their specific vegetable or
animal origin.
The adjective "hydrogenated" must accompany
the indication of a hydrogenated oil where the
vegetable origin or the specific vegetable or
animal origin is mentioned.
However, in either case, Member States may lay
down requirements which are more stringent in
the case of foodstuffs consisting essentially of oils
and fats, emulsified sauces or preparations where
the oil serves as a liquid medium; in that case the
procedure laid down in Article 16 shall apply.
"Fat", together with
either the adjective "vegetable" or "animal",
as appropriate, or
an indication of their specific vegetable or
animal origin.
However, in either case, Member States may lay
down requirements which are more stringent in
the case of foodstuffs consisting essentially of oils
and fats or emulsified sauces; in that case the
procedure laid down in Article 16 shall apply.
"Flour", followed by a list of the cereals from
which it has been obtained in descending order
by weight.
Starch.
Fish.
Poultrymeat.
 Council 913

Definition Designation

All types of cheese where the cheese or mixture Cheese.

of cheeses constitutes an ingredient of another
foodstuff and provided that the name and
presentation of such foodstuff does not refer to a
specific type of cheese.

All spices and spice extracts not exceeding 2% by Spice(s) or mixed spices.
weight of the foodstuff.

All herbs or parts of herbs not exceeding 2% by Herb(s) or mixed herbs.

weight of the foodstuff.

All types of gum preparations used in the Gum base.

manufacture of gum base for chewing gum.

All types of crumbed baked cereal products. Crumbs or rusks as appropriate.

All types of sucrose. Sugar.

Anhydrous dextrose and dextrose monohydrate. Dextrose.

All types of caseinates. Caseinates.

Press, expeller or refined cocoa butter. Cocoa butter.

All crystallized fruit not exceeding 10% of the Crystallized fruit.

weight of the foodstuff.
914 Council

ANNEX II
Categories of ingredients which must be
designated by the name of the category to

Colour Acidity regulator

Preservative Anticaking agent
Antioxidant Modified starches 1
Emulsifier Artificial sweetener
Thickener Raising agent
Gelling agent Antifoaming agent
Stabilizer Glazing agent
Flavour enhancer Emulsifying salts 2
Acid Flour improvers

1 Indication of specific name or EEC number is not

required.
2 Only for processed cheeses and processed cheese

products.
Index

Absolute, 201 Ambrette, 365

Acceptable daily intake, 839 essential oil, 381
Acetic acid, 638 American Society for Testing and Materials, 17
Achillea, 365 American Spice Trade Association, 18
Acidulants, 635 Amygdalin, 342
Activated flavor Amyris, 365
sensory/instrumental correlations, 762 Analyses, see Flavor analysis
Adipic acid, 640 Analytical methods
Adsorption techniques, 201 in quality control, 716
Adulteration, 731-742 see Flavor chemistry
addition of synthetic compounds, 732 Angelica, 257,365,366
essential oils, 739 essential oil, 381
gas chromatography, 733 Angola, 366
incentive, 731 Angostura, 366
Affective tests, sensory, 819 essential oil, 381
Agrimony, 365 Anise, 258, 366
Ajowan,365 essential oil, 381
Alant, 365 Anise, China Star, 260,366
Alcohol content Anise pepper, 366
method, 718 Annatto, 805
Alcohols ANOVA, 745
microbially produced, 171 Anthocyanins, 806
Aldehydes Apple, 208
microbially produced, 170 juice, 210
Alexanders, 365 preservation, 212
Alfalfa, 365 Apricot, 213
Alispice, 365 Apricot kernel, 366
Ali tame, 635 Areca, 366
Alkanet, 805 Arnica, 366
Alkanna, 365 Artemisia, 366
Alliaceous flavors, 178-185 essential oil, 381
Allspice (pimento, Jamaican pepper), 255 Artichoke, 366
essential oil, 381 Artificial flavor, specifications, 729
Allyl isothiocyanate, 86 Asafetida, 178, 366
Almond, 342, 365 essential oil, 381
bitter, 365 Ash, 366
sweet, 365 Aspartame, 634
Aloe, 365 Association of Official Analytical Chemists (AOAC),
Althea, 365 18

915
916 Index

Associations related to the flavor industry, 15-20 Black cumin, 266

American Society for Testing and Materials, 17 Black currant, see Currant
American Spice Trade Association, 18 Black mustard, see Mustard, black
Association of Official Analytical Chemists Black pepper, 318
(AOAC), 18 see Pepper also
British Industrial Biological Research Association sensory profile, 830
(BIBRA), 19 Black tea aroma, 94
Chemical Sources Association (CSA), 19 Blackberry, 366
Codex Alimentarius Commission, 15 Blackberry (Bramble), 214
Food Chemicals Codex, 17 Blueberry, 215
International Organization for Standardization, 16 Bog myrtle, 366
Astringency, 652 Bois de rose, 366
Avens, 366 essential oil, 382
Avocado, 214 Boldus, 367
Borage, 367
Balm, 366 Boronia, 367
Balm (lemon balm), 260 Bouquet garni, 337
essential oil, 381 Boysenberry, 215
Balsam of Tolu, 347, 366 Brazil nut, 343
Balsam Peru, 347,366 Brilliant Black PN (BN), 797
essential oil, 381 Brominated vegetable oil, 577
Banana, 214 Brooklime, 367
Barbecue spice, 268 Bryonia, 367
Basil, bush, 366 Buchu, 367
Basil, sweet, 261, 366 essential oil, 382
essential oil, 381 Buckbean, 367
Bay, West Indian, 265,366 Buckthorn, 367
essential oil, 382 Burdock, 367
Bay laurel (sweet bay), 264,366 Burnet, 367
essential oil, 382
Beet powder, 806 Cacao, 189, 367
Benzaldehyde essential oil, 382
natural, 216 Caffeine, 649
Benzenoid compounds, 76, 77 Cajeput, 367
Benzoin, 347, 366 Calamint, 367
Bergamot, 366 Calamus, 367
essential oil, 382 Calendula, 367
Betony, 366 Calumba, 367
Beverage emulsions Camomile, 367
methods of evaluation, 718 Camomile (German chamomile)
British Industrial Biological Research Association essential oil, 382
(BIBRA), 19 Camomile (Roman or English chamomile)
Biogenesis of fruit aroma, 63-69 essential oil, 382
Biotechnology, 155-175 Camphor, tree, 367
biotransformation of flavor precursors, 161 essential oil, 382
definition, 156 Cananga, 367
enzymatic bioconversion, 172 essential oil, 382
fermentation, 164-172 Candlenut, 367
microbial production of pure flavor chemicals, 165 Canella (white cinnamon), 267
microbially produced, 167 Canonical correlations, 745, 780
plant tissue culture-derived flavors, 157-163 Canthaxanthin, 810
Birch bark Caper, 367
essential oil, 382 Capsaicin, 651
Birch, sweet, 366 Capsaicinoid
Bitter almond, 216, 366 sensory/instrumental relationships, 829
essential oil, 382 Capsaicinoids-capsaicin, 270
Bittering agents, 186, 187 Capsicum, types of, 267-269, 367
natural, 187 barbecue spice, 268
Bitterness, 648-651 biotechnology, 161
 Index 917

cayenne pepper, 269 Chicory (endive), 368

chili pepper and chilies, 269 Chili pepper and chilies, 269
pimiento, 269 Chili powder, 337
Caramel, 807 Chiral compounds
Caramelization, 100 adulteration, 734
Caraway, 274,367 measurement,47
essential oil, 382 Chirata, 368
Caraway, black (black cumin), 367 Chive, 180, 368
Carbon black, 815 Chloroanisoles, 117
Cardamom, 275,367 Chlorogenic acid, 197
essential oil, 383 Chlorophenols, 117
Carmoisine (Azorubrine), 793 Chlorophyll, 810
Carob, 194, 367 Chocolate
Carotene and carotenoids, 808 flavor constituents, 193
Carrot, 367 Chocolate Brown HT (CI Fod Brown 3), 797
essential oil, 383 Chocolate fudge, 192
Cascara sagrada, 367 Chocolate liquor, 192
Cascarill bark, 367 Cinchona, 368
essential oil, 383 Cinnamon, 280-284,368
Cashew nut, 343 Batavia cinnamon, 283
Cassava, 368 Ceylon cinnamon, 281
Cassia,368 China Cassia-cinnamon, 282
see Cinnamon Saigon cinnamon, 282
Cassia, Chinese, 367 Cinnamon bark, cassia
essential oil, 383 essential oil, 383
Cassia buds, 278 Cinnamon bark, Ceylon
Cassie, 368 essential oil, 383
Castor oil, 368 Cinnamon leaf, Ceylon, 283
Catechu, black, 368 essential oil, 383
Catmint (catnip), 368 Cinquefoil, 368
Cayenne pepper, 269, 368 Citric acid, 640
Cedar, white, 368 Citron, 221
essential oil, 383 Citronella, 368
Celery, 278,361,368 Citronella, Ceylon
Celery seed, 368 essential oil, 383
essential oil, 383 Citronella, Java
Centaury, 368 essential oil, 383
Centrifugal coating, 622 Citrus fruits, 221-225
Centrifugation, in manufacturing, 571 citrus oils, 222
Certified food colors, 790 composition of, 224
Character impact, in creation, 702 grapefruit, 223
Cheese lemon-cold-pressed, 223
see Dairy flavor, 89,93 lemon-distilled, 223
Chemical Sources Association (CSA), 19 lime-distilled, 223
Cherry, 215-220 lime-expressed, 223
Dalmatian cherries, 215 orange-bitter, 223
English Morello cherries, 215 orange-sweet, cold-pressed, 224
Montmorency cherries, 215 orange-sweet, distilled, 224
sweet cherries, 215 tangerine (Mandarin), 224
wild cherry, 216 terpeneless and concentrated citrus oils, 224
Cherry, wild bark, 368 citron, 221
essential oil, 383 grapefruit, 221
Cherry laurel, 368 kumquat, 221
Cherry pits, 368 lemon, 221
Chervil, 368 lime, 221
essential oil, 383 mandarin, 221
Chestnut, 343, 368 orange,221
Chewing gum, 347 tangerine, 222
Chicle gum, 347 Citrus peels, 368
918 Index

Citrus Red #2, 796 Costus, 369

Clarification, 564 Council directive of December 18, 1978, 901
apple juice, 211 Council directive of June 22, 1988, 897
Clary sage, 368 Council of Europe blue book, 845
Clove, 285-287,368 Cranberry,225,81 2
Clove bud Cress, 369
essential oil, 383 Crocetin, 814
Clove leaf Cubeb, 369
essential oil, 383 essential oil, 384
Clove stem Cumin, 288,369
essential oil, 383 essential oil, 384
Clover, 369 Cumin, black, 369
essential oil, 383 Curacao orange, 369
Cluster analysis, 745,778 Curcuma, 369
Coacervation, 588, 620 Curcumin, 336
Coca, 369 Currant, 225
Cochineal and carmine, 811 Currant, black, 369
Cocillana, 369 Curry leaf, 369
Cocoa and chocolate, 186-195 Curry powder, 337
chocolate fudge, 192 Cusparia, 369
chocolate liquor, 192 Cyclamates, 633
cocoa production, 190 Cyclodextrins, 617-620
constituents of cocoa, 191
major sources of cacao beans, 188 Daikon, 369
pH values of cocoa, 191 Dairy flavors, 144-149
types of cocoa, 191 butter flavor, 147
Cocoa powder extenders and replacers, 193 cheese flavors, 148
Coconut, 344, 369 cultured dairy flavors, 147
Codex Alimentarius Commission, 15 enzyme modification, 144
Coffee, 195-200,369 guidelines for production and labeling of process
coffee flavor, 198 flavors, 150
coffee substitutes, 198 milk and cream flavors, 146
commercial sources of green coffee beans, 195 regulatory issues, process flavors, 149
instant (soluble) coffee, 197 Dairy products, 88
U.S. per capita consumption, 195 cheese, 89
Cognac oil amino acids and peptides, 92
essential oil, 384 carbonyls, 91
Cola, 369 fatty acids, 90
Cola nut, see Kola nut sulfur compounds, 91
Color Additives Amendments of 1960, 789 milk, 88
Color evaluation Roquefort (blue) cheese flavor, 93
in quality control, 716 Damiana, 369
Comfrey, 369 Damson, see Plum
Commission directive of January 16, 1991, 897 Dandelion, 369
Concrete, 201 Date, 226
Coniferin, 650 Davana, 370
Consumer central location tests, 828 essential oil, 384
Consumption ratio (CR), 841 Deep fat-fried flavor, 98
Conversions, weight/volume, 601 Diacetyl, 102
Cooling, 652 Dictam, 370
Copaiba, 369 Difference testing, 819
Copaiba balsam, 348 Digestion, 548
Coriander, 287, 369 Dill, 290-292,370
essential oil, 384 Dill, Indian, 370
Cork oak, 369 essential oil, 384
Com syrup, 630 Dill seed, 290
composition, 630 essential oil, 384
Correlation matrix, 776 Dill weed, 291
Costmary, 369 essential oil, 384
 Index 919

Diluents for flavors, 702 manufacturing methods, 200

Directional triangle test, 821 absolute, 201
Discriminant analysis, 773 adsorption techniques, 201
Disodium guanylate, 643 concrete, 201
Disodium inosinate, 643 enfleurage,201
Distillates, 557 expression (or pressing), 200
Dittany,370 isolate, 201
Dittany of Crete, 370 solvent extraction, 200
Dog grass, 370 steam distillation, 200
Dragons blood, 370 nitrogen compounds, 85
Drum dryers, 587 oxygenated terpenoid compounds, 75, 76
Dry flavor production, 578-589 producing countries, 381-390
Dry mixing and blending, 589-595 specifications, 201
Dryers, 579 sulfur compounds, 85
Dulse, 370 terpenes, 74-85
Duo-trio test, 821 terpenoid content, 78
yield, 381-390
Essential oils and oleoresins of herbs, 255-337
Elder flowers, 370 Esters
essential oil, 384 microbially produced, 168
Elecampane, 370 Estragon, 292,370
Elemi, 370 essential oil, 384
essential oil, 384 Ethylene oxide, 244
Emulsifying agents, 573 Eucalyptus, 370
Emulsion production, 574 essential oil, 384
Emulsions European economic community
manufacturing, 572-574,608 labeling, 897-914
methods of evaluation, 718 European Flavour and Fragrance Association (EFFA),
spice, 253 847
Encapsulated spices, 254 Extraction, 546-553
Encapsulation, 605-625 Extrusion-encapsulation method, 613-617
coacervation, 620
extrusion, 613
fat encapsulation, 620 Factor analysis, 745, 777
miscellaneous processes, 622 FAO/WHO, 846
molecular inclusion via cyclodextrins, 617-620 Fast Red E, 794
spray drying, 605 Fat encapsulation, 620
drier operating parameters, 612 FD&C Blue No.1 (Brilliant Blue FCF), 795
encapsulation matrices, 605 FD&C Blue No. 2 (Indigotine), 795
flavor retention, 607 FD&C Green No.1 (Guinea Green), 795
flavor stability, 611 FD&C Green No.3 (Fast Green), 795
Enfleurage, 201 FD&C Red #2 (Amaranth), 793
Enzymatic flavor changes, 129 FD&C Red #3 (Erythrosine), 793
Enzymes FD&C Red #4 (Ponceau SX), 793
bioconversion of flavor chemicals, 172 FD&C Yellow No.5 (Tartrazine), 794
dairy flavors, 144 FD&C Yellow No.6 (Sunset Yellow FCF), 795
off-flavor, 129, 130 FD&C Yellow No. 10 (Quinoline Yellow), 794
EOAdata FD&C Violet No. 1 (Violet No.1), 796
example for methyl ionone, 723 FDA redbook, 841
Erigeron, 370 Federal Food, Drug, and Cosmetic Act of 1938, 789
essential oil, 384 Federal Register
Essences labeling, 861
recovery process from fruit, 218 Fennel, 292
spice, 253 Fennel, bitter, 370
Essential oils, 381-390 Fennel, sweet, 370
benzenoid compounds, 76, 77 essential oil, 384
botanical source, 381-390 Fenugreek,294,370
chemistry, 74-86 Fermentation, 100-106
deterioration, 596 acids, 101
920 Index

alcohols, 103 artifical flavor, 862

biotechnology, 164-172 decision pathway, 871
carbonyls, 102 naturalflavor,863
esters, 101 regulations 21CFR, 861
flavors formed via, 100 spice, 862
lactones, 105 with other natural flavor, 867
terpenes, 103 Flavor library
Fig, 226, 370 see Library, 696
Filtering, 566-570 Flavor manufacturing, 538-625
Filtering aids, 567 centrifugation, 571
Fine herbes, 338 distillation, 553-558
Fir, 370 fractional distillation, 554
essential oil, 384 molecular distillation, 556
Flash point, organic chemicals, 514-529 steam distillation, 554
Flashing, in colors, 797 dry flavor production, 578-589
Flavor, formation in plants, 62-74 dry mixing and blending, 589-595
biogenesis of fruit aroma, 63-69 emulsions, 572-574
flavor formation in vegetables, 69-73 extraction, 546-553
glycosides, 67 liquid flavor production, 560-578
influence of genetics, nutrition, environment, packaging and storage, 595
maturity, and storage on flavor, 73 packaging materials, 599
location of flavor in plant, 73 raw materials handling, 540
Flavor analysis, 24-60 comminution, 541-544
concentration, 42-44 spoilage, 596
adsorption, 44 factors affecting product deterioration, 597
evaporation, 43 sterilization/pasteurization, 577
freeze concentration, 44 Flavor scalping, 123-125
direct injection, 44 Flavoring ingredients classified as GRAS
gas chromatography, 45-50 FEMA number, 655-670
high-pressure liquid chromatography, 50 Flavorist, 691-711
identification of volatile flavors, 51 attributes, 692
isolation of food flavors, 26-42 effective interfaces, 706
distillation methods, 32-35 flavor creation, 701-706
headspace methods, 26-32 flavor laboratories, 699
individual classes, 40-42 flavoring components, 700
solvent extraction, 35-40 laboratory glassware, 701
sample preparation, 25,26 responsibilities, 691
supercritical fluid chromatography, 51 samples, 711
Flavor and Extract Manufacturers' Association training flavorists, 694
(FEMA), 12, 843 Flavors from lipids, 98-100
decision tree, 841 Fluidized bed coating, 621
number, organic chemicals, 514-529 Food Additives and Contaminants Committee, 846
Flavor chemicals Food Chemicals Codex, 17
usage level, 166 Food colorants, 788-816
Flavor chemistry, 61-115 certified food colors, 790
Flavor contributory, in creation, 702 colors permitted in the United States, 791
Flavor creation, 701-706 dyes,790
Flavor differential, in creation, 702 forms of the FD&C dyes, 797
Flavor directive (EEC, 1988), 847 label declaration, 790
Flavor industry, 1-23 Color Additives Amendments of 1960, 789
future, 8 Federal Food, Drug, and Cosmetic Act of 1938, 789
history, 2 international regulations for colorants, 788
legislation, 10 lakes, 800
relationships with consumers, 7 dispersion, 803
relationships with the government, 6 uses of lakes, 802
research, 5 oil-soluble dyes, 798
size and market, 2 solubilities of FDC colors, 799
technical service, 5 Food product labeling, 853
Flavor labeling in the United States, 860 Foods used as sweeteners, 629
 Index 921

Fructose, 627 ground spices, 238

Fruit flavors, 86-88 microbiological contamination in spices, 243
aromatic components, 87 spice products, 237
fruit flavors with other natural flavors (WONF), 206 sterilized spices, 243
fruit juice and flavor, 204 test applied to, 238
sugars and acids, 87 United States imports, 235
Fumaric acid, 640 use and chief producing areas, 241
Fungi, 93 whole spices, 238
Hesperidin, 650
Galangal, 370 Hickory, 371
essential oil, 385 High-pressure liquid chromatography, 50
Galbanum, 370 in adulteration, 739-741
essential oil, 385 High-intensity sweeteners, 630-635
Gambir,371 Homogenization, 575
Garlic, 86, 180, 371 Honey,629
essential oil, 86, 385 Hops,371
Gas chromatography, 45-50 essential oil, 385
in quality control, 723 Horehound, 371
Genet,371 Horsemint, 371
Gentian, 371 essential oil, 385
Gentian, stemless, 371 Horseradish, 372
Geranium, 371 Horseradish tree, 372
East Indian, 371 Huckleberry, 227
essential oil, 385 Hyacinth, 372
rose,371 Hybrid priority levels, 841
Germander, 371 Hydrolyzed vegetable proteins, 141
Ghatti gum, 371 Hydroxybenzyl isothiocyanate, 86
Ginger, 295,371 Hyssop,372
essential oil, 385 essential oil, 385
Ginkgo, 371
Glucose, 627 Iceland moss, 372
Glycerol abietate, 577 Identification of volatile flavors, 51
Glycerol tribenzoate, 577 Immortelle, 372
Glycosides, 67 essential oil, 385
bitter, 649 Imperatoria, 372
Glycyrrhiza, 371 Information services, 20-22
Glycyrrhizin, 631 abstracts, 20
Gooseberry, 226 associations and societies, 21
Grains of paradise, 300, 371 journals and trade magazines, 21
Grape,226 Inorganic acids, 641
Grape skin, 812 phosphoric acid, 641
Grapefruit, 221,371 Inorganic color pigments, 815
essential oil, 385 carbon black, 815
GRAS substances, 843 iron oxides, 815
Ground ivy, 371 titanium dioxide, 815
Guaiac ultramarine, 815
essential oil, 385 International Committee on Flavor Priority Setting,
Guaiacwood, 371 841
Guarana, 371 International flavor legislation, 876-913
Guava, 227, 371 definitions, 877
flavorings, 877
Hamamelis, 371 food additives, 877
Haw, black, 371 European economic community, 897-914
Hazelnut, 344 systems of control, 878
Hemlock, 371 worldwide review, 879
essential oil, 385 Argentina, 879
Herbs and spices, 234-255 Australia, 880
composition, 239 Austria, 880
distillation of herbs and spices, 246 Belgium, 881
922 Index

Brazil, 881 Kola nut, 345

Bulgaria, 881 Kumquat, 221
Canada, 881 Kuromoji, 372
Chile, 882
Czechoslovakia, 882 Labdanum,348,372
Denmark, 882 essential oil, 386
Finland, 883 Labeling regulations, 853-875
France, 884 flavoring materials, 853
Germany, 884 food product labeling, 853
Greece, 885 GRAS substances, 853
Hungary, 885 nutritional labeling, 854
India, 885 worldwide labeling regulations, 855
Italy, 886 Lactic acid, 640
Jamaica, 886 Lactones, 100
Japan, 887 formation due to heating, 100
Netherlands, The, 887 formation via fermentation, 105
New Zealand, 887 microbially produced, 167, 168
Norway,888 Lactose, 628
Peru, 888 Laurel (sweet bay), 372
Poland, 888 essential oil, 386
Portugal, 888 Lavandin (Abrialis type), 372
Romania, 888 essential oil, 386
Singapore, 888 Lavender,372
South Africa, 889 essential oil, 386
Soviet Union (Russia), 889 Lavender,spikeleek,372
Spain, 889 essential oil, 386
Sweden, 889 Leek, 181
Switzerland, 890 Lemon, 221, 372
United Kingdom (Great Britain), 890 essential oil, 386
United States of America, 891 Lemon oil, 739
Yugoslavia, 893 adulteration, 739
International Organization for Standardization, 16 Lemon verbena, 372
International Organization of the Flavour Industry essential oil, 386
(IOFI), 13, 847 Lemongrass, 372
guidelines for production and labeling of process essential oil, 386
flavors, 150 Library, 696
Invertsugar,628 applications, 699
Iron oxides, 815 chemistry, 696
Irradiation general, 696
spices, 245 marketing, 696
Isolate, 201 Licorice (liquorice), 338, 372
Iva,372 Licorice root, 631
Light-induced off-flavors, 129
Jaborandi, 372 Light-oxidized off-flavor
Jackknifing, 775 sensory/instrumental correlations, 774
Jasmine, 372 Lime, 221,372
essential oil, 385 essential oil, 386
Joint FAO\ WHO Expert Committee on Food Lime (Linden), 372
Additives (JECFA), 838 Limonin, 650
Juice and concentrate tables, 208 Linaloe wood, 372
Juniper berry, 372 essential oil, 386
essential oil, 385 Linden, 372
Lindenleaves,373
Ketones Lipase, off-flavor, 130
microbially produced, 170 Lipid oxidation
Kino,348 off-flavor, 126-128
Kirschwasser, 216 Lipids, thermally generated aroma, 98-100
Kiwi fruit, 227 Lipoxygenase, off-flavor, 130
Kola,372 Liquid flavor production, 560-578
 Index 923

Locust, 373 Moisture content

Long, 375 method, 722
Lovage, 373 Molasses, 374, 630
essential oil, 386 Molecular inclusion via cyclodextrins, 617-620
Lungmoss, 373 Monosodium glutamate (MSG), 642
Lungwort, 373 Monoterpene alcohols, 78-80
Lupulin, 373 Monoterpene aldehydes, 82, 83
Monoterpene ketones, 83, 84
Mace, 305,373 Mullein, 374
essential oil, 386 Multidimensional scaling, 745, 778
see Nutmeg/mace Multivariate analysis of variance (MANOVA), 745,
Maceration, 548 772
Maguey,373 Mushrooms and fungi, 339-341,374
Maidenhair, 373 extract, 341
Malic acid, 641 Musk, 372
Malt, 373 Mustard, 86, 302, 303
Maltol,645 black mustard, 303, 374
Maltose, 629 brown, 374
Mandarin (tangerine), 221,373 essential oil, 86, 387
essential oil, 387 white mustard, 302, 374
Mango,227 Myrrh, 348, 374
Mannitol, 629 essential oil, 387
MANOVA, 745,772 Myrtle,374
Maple, mountain, 373 essential oil, 387
Maple sugar, 629 Narcissus, 374
Marigold, pot, 373 Naringin, 374, 650
Marjoram, sweet, 300, 373 Nasturtium, 374
essential oil, 387 National Academy of Sciences, 841
Marjoram, wild, 302 National organizations, 7
Mastic, 373 Natural
Mate, 373 definition, 156
Measures, conversion, 599 Natural colorants, 803
Meat and savory flavors, 140-144 see individual colorant by name
Melilotus, sweet clover, 373 sources of natural colorants, 804
Melon, 228 Natural flavoring materials, 177-364
Mentha arvensis (corn mint) alliaceous flavors, 178-185
essential oil, 387 classification, 176
Menthol, 373 Natural sweeteners, 630
microbially produced, 171 Nature, identical,
Menthyl acetate, 373 European definition, 898
Microbial off-flavors, 131-133 Nepeta (catnip), 374
Microbial production of pure flavor chemicals, 165 Neroli, bigarade, 374
Microbiology, 728 Nettle, 374
spices, 243 Nigella, 374
Mignonette, 373 Nomenclature, organic chemicals, 529-537
Milfoil (Yarrow), 373 Nonabsorbable food colors, 815
Milk, 88 Nonenzymatic browning
Mimosa (black wattle), 373 flavor formation, 94-98
Mints off-flavor, 128, 129
cologne mint, 373 Nonvolatile components
corn mint, 373 see Taste, 626
culinary, 302 Nucleotides, 643-645
horse mint, 373 Nutmeg, 374
peppermint, 373 essential oil, 387
round mint, 373 Nutmeg/mace, 304
spearmint, 373 Nuts, 342-346, 374
water mint, 373 composition, 342
Mixed pickling spice, 338
Mixing, 560 Oak, English, 374
 924 Index

Oak, white, chips, 374 Origanum (wild marjoram), 309

Oak moss, 374 essential oil, 387
resin, 348 Orris, 375
Ocimum essential oil, 388
essential oil, 387 Overall liking scores
Odorants tests, 693 statistical discussion, 765
Off-flavors in foods, 116-138 Oxidation of lipids, 98
chlorophenols, 117 Oxygenated terpenoid compounds, 75,76
disinfectants, pesticides, and detergents, 121 principal compounds and their sources, 78
flavor scalping, 123-125
microbial off-flavors, 131-133 Packaging and storage, 595
off-flavors due to chemical changes in the food, Paired comparison, 821
126-131 Palmarosa, 375
off-flavors due to genetics or diet, 125 essential oil, 388
packaging catalyzed off-flavors, 125 Pandanus, 375
packaging sources, 122 Pansy, 375
waterborne sources, 117-121 Papaya,228
Oil of bitter almond, 343 Paprika, 311, 375
Oleoresin of vanilla, 359 Paprika and red peppers, colorants, 812
Oleo resins Parijata, 375
extraction, 250 Parsley, 312,375
preparation, 250 essential oil, 388
quality, 252 Parsley seed
residual solvents, 251 essential oil, 388
specifications, 253 Passion flower, 375
spice, 250 Passion fruit, 228
uses of oleoresins, 253 Pastry spice, 338
Olibanum (frankincense), 348,374 Patchouly, 375
Olive, 228, 374 essential oil, 388
Onion, 85, 86, 181-184, 374 Patent Blue V (CI Acid Blue 3), 796
biotechnology, 161 Patents, 671-690
essential oil, 85, 86, 387 source, 671
Opopanax,349,374 Peach,229,375
Optical rotation Peanut, 375
method, 717 Pear,229
Orange,221 Pecan nut, 345
Orange, bitter, 374 Pennyroyal, 375
essential oil, 387 essential oil, 388
Orange, sweet, 375 Pepper (black and white), 315-321
essential oil, 387 black, 375
Orchil, 812 essential oil, 388
Oregano (Mexican sage), 308, 375 cayenne, 375
Oregano (wild marjoram), 375 white, 375
Organic chemicals Peppermint, 321,375
boiling point, 514-529 essential oil, 388
FEMA number, 514-529 rectification, 248
flash point, 514-529 Percolation, 548
melting point, 514-529 Persic oil, 375
nomenclature, 529-537 Peru balsam, 350
regulatory status, 514-529 Peruvian balsam, 375
solubility, 514-529 Petitgrain, 375
specifications, 514-529 essential oil, 388
synonyms, 514-537 Photo-induced off-flavors, 129
Organizations of the flavor industry, 12-15 Physiochemical tests in quality control, 725
Flavor & Extract Manufacturers Association Pickling spice, 338
(FEMA), 12 Pimento (allspice), 324,375
International Organization of the Flavour Industry essential oil, 388
(IOFI), 13 Pimento berry, 256
The British Essence Manufacturers' Association Pimiento, 269
(BEMA), 13 Pimpinella, 375
 Index 925

Pine, dwarf Raisin, 230

essential oil, 388 Raspberry, 230,376
Pine, Scotch, 376 Reaction flavors
essential oil, 388 chocolate, 193
Pine, white, 376 see Process flavors and Thermal processing, flavor
bark,376 formation
essential oil, 388 Rectification
Pine nut, 376 peppermint, 248
Pineapple, 229 Red,375
Piperine, 318 Red No. 40 (Ailura Red A C), 794
Pipsissewa, 376 Red Saunders, 376
Pistachio nut, 345,376 Red2G, 794
Plant materials used in flavorings, 365-380 Refractive index
list of names, 365-380 method, 717
regulatory status, 365-380 Regression, 745
sensory properties, 365-380 Regulary status
Plant tissue culture-derived flavors, 157-163 definition of status, 380
Plum,230 colorants, 788
Pomegranate, 230, 376 essential oils, oleoresins (solvent-free), and
Poplar, 376 natural extractives (including distillates), 380
Poppy,324,376 international labeling, 876-913
Pot Marigold, 376 natural extractives (solvent-free) used in
Pot Marjoram, 376 conjunction with spices, seasonings, and
Potato, 361 flavorings, 380
Potentiators and enhancers, 642-648 natural flavoring substances, 380
Poultry seasoning, 338 organic chemicals, 391-515
Prickly ash, 376 plant materials, 365-380
Principal components, 745, 776 process flavors, 149
Process flavors, 139-154 spices and other natural seasonings and flavorings,
meat and savory flavors, 140-144 380
protein hydrolysates, 141 Residual solvents
sea also Thermal processing ,flavor formation during method, 720
types of process flavors, 140 Resins, 347-351
yeast and autolyzed yeast extracts, 143 Response surface models, 745,768
Propionic acid, 641 Rhatany, 376
Propylene oxide, 244 Rhubarb, 362,376
Protein hydrolysates, 141 Ribbon blenders, 591
Proteolytic enzymes, off-flavor, 131 Riboflavin (vitamin B 2 , lactoflavin), 813
Prussic acid, 342 Roquefort (blue) cheese flavor, 93
Pumpkin pie spice, 338 Rose,376
Pungency,271,272,319,651 essential oil, 389
capsicum, 651 Rose geranium, 377
ginger, 651 Roselle,377
pepper,651 Rosemary, 324,377
Purslane, 376 essential oil, 389
Pyrolysis reactions, 99 Rosin, 377
Rowan,377
Quality control, 713-730 Rue,377
analytical methods, 716
sensory analysis, 713-716 Saccharin, 632
Quassia, 376 Safety of flavorings, 838-851
Quassin, 650 consumption ratio, 841
Quebracho, 376 Council of Europe blue book, 845
Quillaia, 376 evaluation of food additives, 838
Quince, 376 food additives and flavoring substances, 839
Quinine, 649 GRAS substances, 843
priority setting, 840
Racombole, 376 Safflower, 377,814
Radioactive isotopes Saffron, 326, 377
adulteration, 738 Sage,327
926 Index

sensory profile, 829 Sensory /instrumental correlations

Sage, Dalmation, 377 see Statistical methods, 761,829
essential oil, 389 Serpentaria, 378
Sage, Greek, 377 Sesame, 331
essential oil, 389 Sesame (Benne seed), 378
Sage, Spanish, 377 Sesquiterpene alcohols, 81, 82
essential oil, 389 Sesquiterpene ketones, 84, 85
Salt, 645 Setting up a sensory program, 836
Salt substitutes, 648 Shallot, 378
Samphire, 377 Sieve sizes, 243
Samples for customers, 711 Sieving, 544
Sandalwood, 377 Signal detection (r-index), 822
Sandalwood, West Indian (amyris) Simaruba, 378
essential oil, 389 Sinigrin, 649
Sandalwood, white (East Indian) Sloe, 231,378
essential oil, 389 Snakeroot, 378
Sandarac, 377 Soluble essences, 552
Sarsaparilla Solvent extraction, 551
Ecuador, 377 Sorbitol, 629
Honduras, 377 Sorrel, 378
Mexican, 377 Southernwood, 378
Sassafras, Brazilian, 377 Soy,378
essential oil, 389 Spanish origanum, 378
Sausage seasoning, 338 Spearmint, 331, 378
Savin, 377 essential oil, 389
Savory,330,377 Specific gravity
summer-essential oil, 389 method, 717
winter-essential oil, 389 Specifications
Schinus molle, 377 oleoresins, 253
essential oil, 389 organic chemicals, 514-529
Scientific literature reviews (SLR), 845 Spice and herb mixes, 337,338
Scoville heat units, 722 Spikelavender,378
Scoville test method, 271 essential oil, 389
Seafood flavor, 100 Spoilage,596
Senna, Alexandria, 377 Spoonwort, 378
Sensory analysis, 817-837 Spray chilling, 621
affective tests, 827 Spray-dried flavor, specifications, 728
applications of sensory testing, 818 Spray drying, 605-613
consumer central location tests, 828 Spray dryers, 582
descriptive analysis, 824 Spruce,378
rank-order, 826 St. Johnswort, 377
in quality control, 713 St. John's bread, 377
methods, 819 Stable isotopes
difference testing, 819 adulteration, 736
directional triangle test, 821 Star anise, 378
duo-trio test, 821 essential oil, 389
multiple comparison test, 822 see Anise
paired comparison, 821 Statistical methods, 743-787
triangle test, 820 analysis of variance, 760
physical considerations of testing, 832 ANOVA, 751
facilities, 833 building, comparing, and selecting models, 759
quality evaluations, 827 comparing variances, 771
sample preparation and presentation, 834 discriminant analysis, 773
carriers/medias, 835 estimation and hypothesis testing, 748
sensory-instrumental relationships, 829 general overview, 743
setting up a sensory program, 836 interpreting regression coefficients, 757
subjects, 830 MANOVA, 772
selection and screening criteria, 831 multivariate observations, 771
test objectives, 817 regression, 753
 Index 927

selecting techniques, 746 pyrolysis reactions, 99

variable and data types, 744 seafood flavor, 100
Sterilization Thistle, holy, 378
herbs and spices, 558 Thyme, 334, 378
Sterilization/pasteurization, 577, 578 essential oil, 389
Storage of flavoring materials, 601 Titanium dioxide, 815
Storax, 350, 378 Tolu,379
essential oil, 389 Tolu balsam, 350
Strawberry, 231 essential oil, 389
biotechnology, 162 Tomato, 362, 379
Structure, organic chemicals, 529-537 Toxicological data, 838
Succinic acid, 641 Trace metals, 598
Succinic anhydride, 641 Trainee flavorists, 694
Sucralose, 635 Triangle test, 820
Sucrose, 627 Trigeminal effects, 651
Sucrose acetate isobutyrate, 577 Triticum, 379
Sumbul,378 True fruit extract from extracts, 209
Sunflower, 378 Truffle
Supercritical fluid chromatography, 51 African, 379
Surface oil Black French, 379
method, 721 Red English, 379
Sweet basil, see Basil White Italian, 379
Sweet bay, see Bay laurel Winter, 379
Sweet cicely, 378 Tuberose, 379
Sweet marjoram, see Marjoram, sweet essential oil_, 389
Sweet savory, see Savory Tumbler mixers, 593
Sweet woodruff, 378 Turmeric, 336, 379
Sweetness, 626 essential oil, 389
Synthetic sweeteners, 632-635 Turmeric and curcumin, 814
Turmerone, 336
Tagetes, 378 Turpentine, 379
Tagetes (marigold)
essential oil, 389 Ultramarine, 815
Tamarind, 378
Tangerine,222,378 Valerian, 379
Tansy,378 Vanilla, 351-360,379
Tarragon (estragon), 332,378 analytical standards for vanilla extract, 358
essential oil, 389 biotechnology, 162
Tartaric acid, 641 blending of vanilla beans, 357
Taste, 627-654 composition of vanilla extract, 359
acidulants, 635 composition of vanilla flavor, 357
bitterness, 648-651 extraction, 358
potentiators and enhancers, 642-648 Madagascarvanilla,354
sweetness, 626 classification, 355
trigeminal effects, 651 Mexican vanilla, 352
Tasting media classification, 353
in quality control, 713 oleoresin of vanilla, 359
Tea,378 sensory profile, 825
Terpenes, 74-85 specifications, 4-fold, 728
The British Essence Manufacturers Association Vegetables, 361-363
(BEMA), 13 Verbean, 379
Theobromine, 649 Veronica, 379
Thermal processing, flavor formation during, 95-100 Vervain, 379
caramelization, 100 Vetiver, 379
deep fat-fried flavor, 98 Violet, 379
flavors from lipids, 98-100 Violet, Swiss, 379
lactones, 100 Violet 6B, 796
nonenzymatic browning, 94-98 Volatile oil
oxidation, 98 method, 721
928 Index

Walnut, 345,379 Xylitol, 629

Watercress, 379
Weighing agents, 577 Yarrow,379
White pepper, 316 Yeast and autolyzed yeast extracts, 143
Wild cherry, 379 Yeast autolysates
Wintergreen, 379 biotechnology, 165
essential oil, 389 Y erba santa, 379
Witch hazel, 379 Ylang-ylang, 380
With other natural flavors (WONF) essential oil, 389
fruit flavors, 206 Yucca, 380
labeling, 867
Wood sorrel, 379 Zdravetz, 380
Woodruff, sweet, 379 Zedoary, 380
Worldwide labeling regulations, 855 essential oil, 389