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1
www.PerfumerFlavorist.com
Improving the
Natural
Processes
+ Geraniol in Flavor
+ A Natural and a Pod:
Commonalities in Vanilla and Tea
+ Perfumer Profile:
Wolfgang Krause, Ph.D.
Aroma Chemicals
Sugars
The life science business of Merck KGaA, Darmstadt, Germany operates as MilliporeSigma in the U.S. and Canada.
Copyright © 2016 EMD Millipore Corporation. All Rights Reserved. MilliporeSigma and the vibrant M are trademarks of Merck KGaA, Darmstadt, Germany.
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FLAVOR
26
17 Flavorist Profile: Gail Underwood
In this exclusive interview with Perfumer & Flavorist, Underwood
shares her knowledge on the evolving flavor industry, creativity
in formulations and why we need flavors in products.
FRAGRANCE
42 The Juice: Wolfgang Krause, Ph.D.
Krause’s work with geraniol, citral and menthol introduced him
to the world of flavor and fragrance where continues to foster
an advocacy for the industry through active participation in the
community and education to the trade and public.
By Pia Long
INGREDIENTS
20 Raw Material Bulletin
42
Jo-El M. Grossman, Director
Jeb Gleason-Allured, Editor in Chief • 1-630-344-6069/jallured@allured.com
Deniz Ataman, Managing Editor • 1-630-344-6070/dataman@allured.com
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ADVERTISING SALES
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AUDIENCE DEVELOPMENT
48
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DESIGN
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EVENTS
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CORPORATE
Janet Ludwig, Partner & President
George Fox, Partner & CEO
61
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A New Experience
DENIZ ATAMAN
Managing Editor
dataman@allured.com
P&F Magazine
W
Editorial Advisory Board hat makes an F&F product memorable? Depth. Layer. Texture.
And its coinciding political climate. By combining these elements
DOLF DEROVIRA together, our senses are engaged, offering a new experience that
President and CEO, reflects our current cultural landscape. So, how are we to continue providing
Flavor Dynamics, Inc. unique experiences in the new year, and under new global government policies?
Deniz Ataman
Managing Editor
a https://www.theguardian.com/uk-news/2016/nov/15/uk-tax-cuts-pwc-philip-hammond-autumn-
statement-gdp-growth
b http://blog.euromonitor.com/2016/11/trump-election-victory-us-economy-consumers.html
Complementing Stevia
“Health conscious consumers – and their number keeps growing –
are looking for better nutrition without compromising great taste so it’s
logical that interest in reduced-sugar and low-sugar products is high…For
example, it works well in products formulated with Stevia to help provide
a more natural sugar taste,” Laroche said.
Ideally, the sweet modifier is intended to create the taste of natural
sugar with minimal caloric value. SymLife Sweet is currently in progress
as the company’s team finalizes its completion.
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
Strategic Growth
Strategically, IFF has succeeded in multiple areas,
preparing the company to continue growing through 2020.
IFF’s encapsulation sales grew to double digits for personal
wash and home care. The sweetness and savory modulation
portfolio is continuing its growth towards double digits also. growth by many consumer packaged goods companies, we
IFF launched four new flavor modules along with commer- are pleased to say that we are in a position to deliver solid
cializing a captive fragrance ingredient. top- and bottom-line growth in 2016,” said Andreas Fibig,
chairman and CEO of IFF.
Global Success
IFF explored growing its business throughout the world The Future of IFF
with success in the Middle East and Asia in both flavors and Looking towards quarter four, IFF will have acquired
fragrances. There was a more than 6% increase in fabric David Michael in order to improve the U.S. flavor busi-
care in the U.S. and home care increased by double digits nesses. The company will also be intending to purchase
in Greater Asia. The company also achieved growth in Fragrance Resources to strengthen IFF in both the U.S.
both its regional and global accounts while it accomplished and Germany.
being the first flavor and fragrance company to join the “Longer-term, we believe that our investment in innova-
World Economic Forum. The World Business Council for tion will enable us to accelerate sales performance while
Sustainable Development executive committee elected IFF simultaneously driving productivity improvements to ensure
as a member this quarter. sustainable profit growth. We’re confident that by doing so,
“For the full year, despite challenging conditions given the cumulative benefits will lead to improved value creation
a higher level of economic uncertainty and limited volume for our customers, employees and shareholders,” Fibig said.
11
Improving Flow
Without proper water storage systems for farmers, maintaining a sustain-
able farm is a challenge. Farmers are forced to rely on water from a nearby
stream or piped water from a water supply project, but nothing is guaranteed.
This project is in place to help communities and farmers, but it will also
promote efficiency as farmers no longer have to rely on neighboring water
sources. The dry season creates water restrictions, forcing farmers to water
two to three times a week. The need for water is dire enough that the farmers
will request water from neighboring farms who are receiving water that week.
As the water tanks are implemented, river flow will improve in dry areas
since there will be no need to fetch water from the natural source. The tanks
will cater to farmers for months and will reduce the conflict between them
and the Samburu and Isiolo areas due to reduced water supply.
To learn more about our global water crisis and conservation efforts, Photo courtesy of Earthoil.
please check out the documentary, Flow for Love of Water (flowthefilm.com).
Frutarom Makes Eighth Acquisition, DuPont Tate & Lyle Celebrate 10 Years,
Purchases Piasa Expand Facility
A Successful Partnership
DuPont Tate & Lyle’s joint venture has made it possible
Frutarom has announced its acquisition of 75% of the
to develop a proprietary process for plant-based feedstocks.
Mexican savories company, Piasa, and will assume $20.5
This will make it possible for the company to further
million of its debt. This is Frutarom’s eighth acquisition this
produce its ingredient 1,3-propanediol. It also allows for
year. The deal will include real estate housing on Piasa’s
other solutions within the company, like Susterra and Zemea
main production site and headquarters in Monterrey.
propanediol, to spread through markets and applications.
Exploring Latin America
“This joint venture started as a revolutionary innovation
Frutarom is gradually becoming one of the 10 largest
project that applied the tools of modern biotechnology
companies in the flavor industry. The company is experienc-
to make high-performance biomaterials in a much more
ing rapid growth with its fifth purchase in Latin America and
sustainable way than traditional petro-chemistry,” stated
its first in the Mexican market.
Michael Saltzberg, global business director of biomaterials
“This is an important strategic acquisition that provides
for DuPont. “Its track record of success has inspired the
Frutarom significant entry into the Mexican market, one of
academic and industrial science community around the
Latin America’s main markets and among the most impor-
world to invest in industrial biotech and is a case study of
tant and fastest growing in the world,” said Ori Yehudai,
how to successfully innovate in this space.
Frutarom CEO.
The purchase agreement will offer the opportunity for
Frutarom to purchase the balance of shares beginning five Multifunctional Portfolio
years after the completion of the transaction and based on Zemea is a biomaterial ingredient that is a multifunc-
the company’s future business performance. The deal is tional humectant that boosts preservatives and can be used
expected to be completed within the next couple of weeks for various consumer products like cosmetics, personal care,
and will be financed through bank debt. food, flavor, pharmaceuticals and laundry and household
At the end of September 2016, Piasa’s sales reached $45 cleaning. Susterra is another biomaterial ingredient that
million in a 12-month period. This was an 8% growth that is a building block for a multitude of applications such as
occurred for the company over the past five years. polyurethanes and heat-transfer fluids.
“Piasa is a leader in Mexico’s savory solutions market and “We’ve grown past what was previously imagined,”
we intend to continue expanding its activity with the support explained Todd Sutton, president, DuPont Tate & Lyle
of Frutarom’s global infrastructures and based on Piasa’s Bio Products. “The versatility of the product allows us to
quality production infrastructure with its excess capacity support the DuPont Sorona fiber business as well as grow
as well as through exploiting cross-selling opportunities by organically with Zemea and Susterra propanediol. The
offering Frutarom’s broad portfolio of solutions to Piasa’s benefits of creating high-performing solutions in combina-
Mexican customers and gaining new customers in the local tion with renewability allows us to continue to expand our
market, along with expanding Piasa’s activity to those coun- market reach in the personal care, food, polyurethanes
tries in the region where Frutarom already has a sales and and heat transfer fluids markets as well as many other
marketing infrastructure in place.” applications.”
History of Fragrances
The tour will be spread out across four floors and divided
into three stages. Guests will first discover the history of
fragrances by focusing on different uses of scents through- to the final product, guests will learn how perfumes are
out the world. The tour will also involve stories from famous created and its journey through the marketing process.
historical figures.
What to do After the Tour?
Sensory Immersion
After the tour, the museum is set to offer additional plans
This part of the tour will demonstrate the power of the and events to complement the sensory tour. There will also
olfactory senses and provide new technologies that immerse be temporary workshops and exhibitions as the museum
the visitors in a scent filled world. More than 60 fragrances continues to draw in visitors with a nasal curiosity.
can be experienced throughout the tour. Why is perfumery associated with France? How is our
olfactory sense linked to memory? What are the founda-
A Perfumer’s Art tional steps in creating a perfume? With these questions
The last stage of the tour explores different aspects of in mind, attendees will get an exclusive sneak peek at the
the fragrance process. From the initial concept of the scent magic and romance of perfumery.
15
Sustainable Sandalwood
TFS has established one of the world’s largest sandalwood
trees in Australia’s tropical north. After harvesting from
15-year-old-trees, TFS replaces and replants saplings as
part of its sustaina¬bility initia-
tives, which also include
renewable energy and water
recycling systems.
“We’re proud to work
with Young Living to
share our premium oil with
consumers across the globe,”
said Mario Di Lallo, head of global
products for TFS Corporation.
“We are honored to align our busi-
ness with Young Living, a like-minded,
environm¬entally conscious, global company.”
G
ail Underwood’s transition from apprentice to
senior flavorist throughout various mergers and
acquisitions, regulatory changes and evolving
consumer preferences offers insight into how amorphous
the industry really is.
Gail began her career in the flavor industry in 1973 as a
soft drink technologist where she was introduced to flavor-
ings in products. As her interest peaked in flavor, she started
an apprenticeship under a senior flavorist. Underwood
worked as a flavorist for 13 years at Barnett and Foster (now
owned by Firmenich), then to Fritzsche Dodge Olcott for
six years until the company was bought by Givaudan. At
Givaudan, Underwood held a senior flavorist position until
she moved to Haarmann and Reimer, which was eventually
bought by Symrise.
P&F: Do you think these acquisitions are a positive “Generally I would feel, as a flavorist
change for smaller companies?
you have to please other people
GU: I think it creates opportunities for new startup
companies and I’ve seen that happen during all of these big with what you’re making. You have
mergers. Smaller companies emerging on to the market can to convince someone else that your
benefit from major manufacturers because maybe compa-
nies are too busy trying to sort out their consolidation with flavor is the best. ”
another company.
P&F: You mentioned that there was no formal
P&F: To go back to the how the industry has training program when you started out in the indus-
changed, you were working at a time when the flavor try. Even to this day, to become a flavorist, you’re
industry was starting to pop off with processed foods working through an apprenticeship with a senior
and emerging technologies. Can you speak to what flavorist. Do you think implementing flavor education
it was like before the analytical technology was would be helpful? Or is being a flavorist more about
available? learning these skills and acquiring this knowledge on
GU: It was hard as a flavorist years ago because we didn’t the job?
have access to the analytical techniques that we have avail- GU: I really believe you need on-the-job training
able now. You have to work that much harder. Often in the to become a good flavorist. There is a school in France
industry, manufacturers want to work with cheaper flavors. (ISIPCA) and a few smaller training courses like the British
If they have a flavoring that they are buying from a certain Society of Flavorists, who have worked with the Reading
company they will quite often look to get it cheaper. With University in running the annual flavor course for recently
17
Underwood began her career as a soft drink technologist where she was introduced to flavorings in products. Ultimately, flavors are a
good thing, she says, as products have evolved over the years to engage consumers’ senses in more advanced ways.
graduated flavorists-in-training who have been employed to GU: If you get to know your customer, you get to know
learn about flavor and raw materials. That gives them a good what they like. You create to satisfy their product needs.
background and it takes the pressure off the companies to You may have to go backwards and forwards until you get it
actually have to do that early training. But ultimately, I think right—especially if you’re creating something new—until
you really need to learn on the job. Nobody can tell you how you get exactly what is considered the best product. You
these raw materials smell and how they react with other need to have a good understanding of your customer’s
things. You need experience that is hands-on. requirements. You need to know what they like and what
their product ranges are and what flavors they tend to go for.
P&F: It’s interesting because nowadays you can That creativity is also based on the knowledge of the
Google and Youtube just about anything. Yet there ingredients that make a good flavor. It’s also subjective
isn’t anything readily available for the public to learn because what I think is the best may not be their idea of it,
how to create a flavor. and vice versa. Generally I would feel, as a flavorist you have
GU: No, because that is all proprietary information to to please other people with what you’re making. You have to
that company. Flavorists move from company to company, convince someone else that your flavor is the best.
but there is a code that you don’t divulge secrets from one
company to another. But basically, the majority of raw mate- P&F: How has the career of a flavorist evolved? Has
rials you’re using are the same within every flavor company. it become more of a pressure to constantly churn out
There are the big flavor companies that have their own raw wins? Or is there time to mull over a formula?
materials and if they think they’re really special, they’ll keep GU: If I make a new flavoring, I need to present that to a
them captive for a certain number of years. It gives them an panel to get that agreement. It probably goes to the applica-
edge. For example, if an ingredient is created that gives a tions team and then to a taste panel; and some will say they
flavor the best taste in the world, a company will not release do or don’t like it. So there will be major and minor modifi-
it until the patent runs out. cations until you get a majority of people who like it. You do
all of this before the customer even sees the product.
P&F: When it comes to working with raw materials
and having to deal with cost and availability, ulti- P&F: Are there any ethical issues that a flavorist
mately, there is still that pursuit of creativity, because has to deal with in their job?
you’re creating flavors in products for people to GU: Certainly, there’s food and flavor legislation that
enjoy. How do you deal with creativity in the stress of we have to follow. Every flavorist should be aware of the
having to perform under these constraints? restrictions of what you can and can’t use. Some food
19
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
20 Ingredients Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
Geraniol
The rose character of geraniol is very bright and fragrant but it also
possesses considerable depth, which is especially helpful in flavors.
N
ature should, in been thrown together by a madman perfect; despite the fact that it did not
many respects, be on a Friday afternoon, the extra quite accurately represent the true
admired. Sadly, not ingredients simply highlighting the character of fresh roses. In my opinion
all essential oils worst aspects of cinnamaldehyde. This it was actually artistically superior in
really represent may seem a little overstated but some many respects. Part of my apprecia-
nature at her finest. oils actually are more interesting and tion of rose otto was driven by the fact
Cassia oil is a case in point. Where impressive from a creative point of that it displayed an optimum level of
true cinnamon oil seems to me to view than others. complexity but the character of the
represent a perfect showcase for the My first encounter with an essential three terpene alcohols that formed
main ingredient, cinnamaldehyde, oil that represented a sublime natural the core of the oil was key. All three,
cassia oil in contrast smells as if it has balance was rose otto. It was, to me, geraniol, nerol and citronellol, smell
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
22 Flavor Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
23
Blackcurrant: The same combina- Grape: An ideal level of addition ale styles. An ideal level of addition is
tion is equally effective in blackcurrant in grape flavors is 1,000 ppm. The 800 ppm.
flavors, but at a rather less prominent addition of this ingredient is most Honey: A similar level of addi-
level. The best level of addition of obviously useful in floral grape styles, tion, 800 ppm, is also useful in honey
geraniol is in the region of 200 ppm. such as Muscat, but it also works well flavors. All styles of honey flavor
Blueberry: Geraniol can add in Concord grape styles. benefit from the addition of geraniol,
a pleasant floral complexity to the Peach: The same combination with not just the most obviously floral styles.
dominant linalool note in blueberry linalool that works in apricot flavors Tomato: Geraniol adds authenticity
flavors at levels of addition between also works well in peach flavors but the and depth to tomato flavors. A good
100 and 200 ppm depending on the ideal level of addition is a little lower, starting point, 400 ppm, will emphasize
effect desired. near 600 ppm. ripeness.
Strawberry: A level of addition of Cherry: Benzaldehyde-dominated
100 ppm also adds a subtle element cherry flavors can be enhanced by the
of depth and fragrance to strawberry addition of geraniol but this ingredi- To purchase a copy of this article or others,
visit www.PerfumerFlavorist.com/magazine.
flavors, enhancing ripeness. ent really comes into its own in more
authentic styles. A level of 400 ppm is
Other Fruit Flavors a good starting point.
Apricot: As with blueberry flavors,
linalool is also the dominant floral note Other Flavors
in apricot flavors. Geraniol adds attrac- Ginger: Geraniol adds fragrance
tive complexity and depth at around and lift to ginger flavors, especially
1,000 ppm. in the context of the subtler ginger
For a rich,
dark chocolate
flavor with a
creamy mouthfeel,
combine 1.66ppm of
Chocolate Thiazole with
3.33ppm of Cocoal FCC
For an almond and milk chocolate
extravaganza, combine 1.66ppm of
Chocolate Thiazole, 3.33ppm of Cocoal FCC
and 1.66ppm of our d-Hazeltone (FEMA 3761)
A Natural
and a Pod:
Shared chemistry,
biochemistry and
processing in tea leaf
and vanilla pod.
namely (-)-epicatechin (EC), (-)-epicatechin-3-O-gallate contribute to the black/brown color of dry oxidized teale-
(ECg), (-)-epigallocatechin (EGC) and (-)-epigallocate- aves. Lipids, amino acids and carotenoids are transformed to
chin-3-O-gallate (EGCg). The structures of (-)-epicatechin produce tea aroma compounds.
(EC) and (-)-epigallocatechin (EGC) are shown in F-1 The process of withering involves placing the leaves in
Other constituents of note in the young leaves include large open holding vessels in the sun or in a cool airy room
amino acids, caffeine, the carotenoids and chlorophyll. for sufficient time to achieve about 20-25% moisture loss.
Oxidation reactions are responsible for the browning of This stage is followed by mechanical tissue damage by
tea leaves as well as the production of taste and aroma com- maceration or rolling or tumbling the tea leaves. Maceration
pounds in the finished products. Depending on the type of is typically used to create CTC (cut, tear, curl) or other
tea, oxidation is almost totally inhibited in white and green broken-leaf teas. Due to extensive cellular disruption, it is
teas; or deliberately initiated, controlled then stopped which the most rapid route to initiate polyphenol oxidation and is
is seen in oolong and black tea a achieved using a rotorvane or a CTC machine. Oxidation
Most of the oxidation processes involve the catechins begins when the integrity of the cell walls within the tea
and the oxido-reductase enzymes polyphenol oxidase (PPO) leaves are compromised. Rolling is a mild process result-
and peroxidase (POD) along with their respective hydrogen ing in a much slower and gentler oxidation and is usually
acceptors. Cell damage in the tea leaf initiates the interac- conducted using a rolling table or by hand. Tumbling is an
tion between molecular oxygen, the polyphenols in the cell even milder route to initiate oxidation and is achieved using
vacuole, PODs in the cell peroxisome and cytoplasmic PPO. large cylinders in which the leaves are tumbled.
In the same oxidative environment, chlorophylls are Control of oxidation in the fermentation stage is managed
degraded to pheophytin and pheophorbide pigments, which by introducing warm, moist, air. The extent to which
oxidation is allowed to occur has a significant effect on the
ahttps://www.worldoftea.org/tea-leaves-oxidation/
finished tea. Oxidation occurs optimally at temperatures
Tea processing includes, in its most protracted operation, the stages of withering and maceration, fermentation then finally firing and drying.
between 27o-30oC and relative humidity of 98%. Oxidation Tea Taste Compounds
is virtually inhibited at 60o-66oC by heating the leaves and The key biochemical reaction relevant to the taste of tea
denaturing the oxido-reductase enzymes. occurs mainly during fermentation and is characterized by
Firing (drying) is achieved by heating the leaves to the oxidation of catechins by PPO with molecular oxygen as
approximately 66oC. the hydrogen acceptor. The initial products from the reac-
The most common firing methods are pan firing, steam-
tion are a family of dimeric theaflavins (F-2). Theaflavins
ing, heat tumbling or baking. Alternative processes include
possess a characteristic benzotropolone moiety, which is
sun drying, microwaving or hot water blanching. The drying
produced by condensation between a catechol-type B-ring
process realizes a final leaf moisture content of 2-3%.
of EC and a pyrogallol-type B-ring of EGC.
If oxidation is totally prevented, tea leaves retain their
The theaflavins are reddish in color and contribute
green color and appearance and the catechins remain
briskness and astringent character to tea. In vitro oxida-
largely intact (white and green teas).
When a semi-oxidized tea is produced, partial conversion
tion of a mixture of EC and EGC with polyphenol oxidase
of catechins to theaflavins and the latter to thearubigins suggested that the enzyme preferentially oxidizes EC to
occurs, resulting in a slight browning in the leaves and a EC-quinone. This electron deficient EC-quinone then
yellower liquor (oolong tea). reacts with the electron-rich EGC B-ring. Subsequent
When fully oxidized black tea leaves exhibit an aroma and oxidation and decarboxylation afforded theaflavins.
taste profile totally distinguishable from un-oxidized finished These compounds are not final products and are oxidized
tea. Drying is conducted to achieve reduced moisture further as EGC was consumed faster than EC during
content for shelf stability and for flavor enhancement. For theaflavin formation since oxidative coupling between
the latter roasting may be employed to generate toasty and two molecules of EGC readily occurs. When EGC is
burnt notes as well as a darker appearance. exhausted in the reaction mixture, the EC-quinone begins
Oolong tea
29
F-2. F-3.
OH OH OH O
O
OH O
HO O
H H
O OH
OH
OH O H OH O
HO
H
OH
OH
HO OH HO OH
Theaflavin Theanaphthoquinone
to oxidize theaflavin via the electron withdrawing action americanin A and 4’,6’-dihydroxy-3’,5-dimethoxy-[1,1’-
of the EC-quinone from the benzotropolone ring. This biphenyl]-3- carboxaldehyde (F-4)
transformation of theaflavins leading to thearubigins is Sensory studies revealed human recognition thresholds
catalyzed by POD with hydrogen peroxide as the hydro- for these compounds with velvety mouth-coating sensa-
gen acceptor. The thearubigens are red in color and tion between 1.0 and 5.0 mmol/kg in water. Quantitative
contribute body to tea [2,3]. Several oxidation products analysis of the compounds in cured beans from different
of the theaflavins are known; the major one being the- geographical origins as well as in non-cured beans revealed
anaphthoquinone [4]. In black tea fermentation, coexisting that, with the exception of americanin A, all the other taste
substances may react with theaflavin quinones or the- compounds were absent in the green bean and found only
anaphthoquinone to form further complex polyphenols. after curing.
The theaflavins and thearubigins, in combination, are the Concentration and taste threshold data for a number
principal contributors to taste, mouth-feel and color of of these velvety mouth-coating compounds were deter-
fermented teas. mined. Highest concentration/taste threshold values, in the
commercial Madagascan vanilla cured extracts evaluated,
Vanilla Taste Compounds in parenthesis, were found for (1-O-vanilloyl)-(6-O-
Traditional vanilla bean curing is characterized by the feruloyl)-b-D-glucopyranoside (234), di-vanillin (281) and
activation of hydrolytic and oxido-reductase enzymes. The 4’,6’-dihydroxy- 3‘,5’-dimethoxy-(1,1’-biphenyl)-3-carboxal-
ripe, green beans, like the young tea leaf contain mainly dehyde (266). Similar data was obtained for cured Vanilla
mono-phenols as the b-D-glucosides account for 12-15% of planifolia beans of Papua New Guinea origin. It is probable
the dry weight of the vanilla pod. An endogenous b-glu- that these compounds contributed significantly to the taste/
cosidase hydrolyzes the phenyl-b-D-glucosides to the free mouth-coating character of cured vanilla beans.
phenols among which the mono-phenol vanillin is the major
compound generated. These phenols are then oxidized New Compounds Linked to Vanillin
principally by PPO/molecular oxygen and/or POD/hydro- Of the new compounds identified (1-O-vanilloyl)-(6-O-
gen peroxide to dimeric and polymeric “brown” pigments. feruloyl)-b-D-glucopyranoside would seem to be linked to
A number of novel phenol oxidation products from cured the known vanillin precursor, vanillin-O-b-D-glucopyran-
vanilla beans were recently isolated and structurally deter- oside commonly known as gluco-vanillin. One of the other
mined. Some of these compounds have interesting taste and compounds was a di-phenol whilst three others were di-
velvety mouth-feel attributes [5]. phenylmethanes. Di-vanillin, a known component of cured
The above authors identified six compounds previously not vanilla beans, was also identified. The routes of formation of
reported in cured vanilla beans namely 5-(4-hydroxybenzyl) these dimeric compounds may involve oxidation, via radical
vanillin, 4-(4-hydroxybenzyl)-2-methoxyphenol, 4-hydroxy- intermediates, mediated by POD/hydrogen peroxide and/
3-(4- hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde, or PPO/molecular oxygen. In the case of the di-phenol
(1-O-vanilloyl)-(6-O-feruloyl)-ß-D-glucopyranoside, compounds, it is established that vanillin in the presence of
F-4. Novel mouth-coating compounds identified in cured Madagascan Vanilla planifolia beans
(modified from reference 5)
O
HO OH
OH
O
H H OH
O HO
O HO O O
OH O
H O
1 2 H3CO 3 OH
O O H
O H H O
H3CO
O 5
O
HO H
HO
HO O
4 OH O
OCH3
OH H3CO OCH3
H3CO
HO
OH OH
O H OCH3 6
O H
HO
HO HO 9 OH
OCH3
H3CO OCH3
7 OH
8 OH
OCH3
vanillin (1)
vanillin-O-b-D-glucopyranoside (2)
5-(4-hydroxybenzyl) vanillin (7)
americanin A (3)
4-(4-hydroxybenzyl)-2-methoxyphenol (9)
4-hydroxy-3-(4-hydroxy-3-methoxybenzyl)-5-methoxybenzaldehyde (8)
(1-O-vanilloyl)-(6-O-feruloyl)-b-D-glucopyranoside (4)
Divanillin (6)
4’,6’-dihydroxy-3’,5-dimethoxy-[1,1’-biphenyl]-3-carboxaldehyde (5)
Key: Green Box: Compound found in cured and uncured vanilla beans
31
It would seem that browning during vanilla bean fermentation is dependent on polyphenol oxidase/molecular oxygen, unless peroxidase is active but limited in
hydrogen peroxide.
conditions have a sparing effect on vanillin loss relative addition. The new catechols formed can readily be
to that observed under aerobic conditions [9]. Both PPO re-oxidized to new o-quinones, which by further function-
and POD are active enzymes in vanilla pods [10,11]. PPO alization can achieve more complex structures. Reaction of
utilizes molecular oxygen as the hydrogen acceptor whilst o-quinones with electron rich nucleophiles, such as amino
hydrogen peroxide performs the same function for POD. acids, result in intra- or inter-molecular addition. With amino
It would seem that browning during vanilla bean fermenta- acids, the reaction is primarily through the -amino groups,
tion is dependent on PPO/molecular oxygen, unless POD is with the exception of lysine and cysteine, to give red or
active but limited in hydrogen peroxide. brown adducts. The products of these reactions are mono-
Purified monomeric PPO from ripe vanilla beans with a substituted phenols that may be oxidized further to colored
molecular weight of ca.34 kDaltons utilizes as primary sub- quinone derivatives [13]. Ortho-quinones can react further
strates the o-diphenols catechol and 4-methylcatechol. The with quinones, phenols, peptides and proteins. The reactions
products from oxidation of these substrates are the corre- of o-quinones with amino acids compete less successfully
sponding ortho-quinones [12]. Other o-diphenol substrates with the non-enzymatic polymerization of o-quinones. In this
present in plants include caffeic and chlorogenic acids. manner, labile o-quinones may react together to yield “mela-
The dominant feature of the biochemistry of o-quinones is noid” type pigments. The mechanism of polymerization is
their ability to readily undergo redox reactions involving a not well defined since the final, colored, melanin products
semi-quinone radical intermediate following single electron are dependent on the nature of the reactants.
reduction. Ortho-quinones are reactive electron deficient
species and when generated in biological environments they The Role of Molecular Oxygen
can react rapidly, often by non-enzymatic pathways, to give The best understood o-quinone polymerization pathway
more stable products. The driving force for this reactivity is is that of the conversion of tyrosine to melanin. Tyrosine
their conversion to aromatic catechols. is first hydroxylated to L-3,4-dihydroxyphenylalanine
Catechol formation occurs by reduction, by addition of (DOPA). The latter is then oxidized to dopaquinone; both
a nucleophile, or by tautomerism followed by nucleophilic reactions were catalyzed by the PPO enzyme cresolase/O2.
35
which are rich in theaflavins in the former, whilst in the Tea Aroma
latter almost complete conversion of catechins to theafla- The volatile fractions of infusions of Chinese green
vins and thearubigins occurs. cultivars, Longjing, Maofeng and Biluochun, produced by
• In vanilla beans, the phenolic precursors are mostly withering and pan-firing were analyzed by aroma extract
present as the b-D-glucosides. These glucosides are dilution analysis [16]. A total of 58 odor active compounds
hydrolyzed enzymatically during the fermentation stage with flavor dilution (FD) factors between 41 and 47 were
of curing to release the mono-phenols. These compounds identified. In all three cultivars and irrespective of the har-
are oxidized readily to dehydro-diphenols by POD/ vesting season, the following compounds—all with high FD
hydrogen peroxide. The other characterized dimeric factors—namely 4-hydroxy-2,5-dimethyl-3(2H)-furanone,
phenylmethane compounds may also be generated by 3-hydroxy-4,5-dimethyl-2(5H)-furanone, coumarin, vanil-
POD/PPO oxidation. PPO/molecular oxygen appears to lin, geraniol, (E)-isoeugenol and 2-methoxyphenol, were
be involved in oxidation of di-phenols, including chloro- identified. These seven compounds are probably essential
genic and caffeic acid, especially to o-diphenols which contributors to the aroma of Chinese green teas [17]. Of
can further react with amino acids or polymerize to form the above chemicals vanillin, geraniol and 2-methoxyphenol
complex uncharacterized polyphenols. Opportunities were probably present as glycosides in the green leaf and
exist within this latter oxidation process for the co- liberated during the withering and fermentation stages. The
oxidation of mono-phenols. The vanilla phenol oxidation two furanones probably arise during the firing and drying
products comparable to the tea theaflavins/thearubigins stages of tea processing by Maillard reaction between the
are the dimeric diphenols and the diphenylmethanes. pentose sugars xylose, arabinose or ribose and the amino
Some of these compounds contribute to the taste/mouth- acids alanine or glycine [18].
feel of cured vanilla bean extracts. The brown coloration The floral compound (E)-isoeugenol was shown to
of cured vanilla beans is probably due to uncharacterized originate from coniferyl alcohol, the latter being derived
oxidation/polymerization of o-diphenols of the chloro- from the amino acid phenylalanine. The formation
genic/caffeic family; a reaction initiated and dependent pathway for the phenylpropene (E)-isoeugenol in Petunia
on the presence of molecular oxygen. hybrida cv. Mitchell flowers were catalyzed by an enzyme
Black tea
37
39
resulting in extensive moisture loss with concomitant with extensive conversion of phenolic glucosides to free
enzyme inactivation but perhaps limited thermal activity. phenols, as a consequence of extensive tissue damage,
with characteristic phenolic notes and associated cara-
From a fixed base of reactants and enzymes in young mellic and other notes due to Strecker/Maillard type
tea leaves, a range of processing treatments realizes a wide reaction products, e.g. isobutanal and 2-methylbutanal,
spectrum of products with differing appearance, taste/ and other thermal process notes [32].
mouth-feel and aroma character. The resulting product
types include white, green, oolong and black teas. These Summary
different treatments as indicated above include: Comparison of the phenolic composition between vanilla
beans and tea leaves show similarities in terms of the mono-
• The degree of tissue damage. This defines the potential phenols, as the glucosides and the catechins, respectively.
for extensive oxidation of the endogenous catechins Both fresh tissues have active PPO/molecular oxygen and
• The length of the fermentation stage. This dictates the POD/hydrogen peroxide oxido-reductase activities. PPO
extent of oxidation of catechins to theaflavins and thea- seems to be associated principally with oxidation of ortho-
rubigins resulting in green through black/brown product di-phenols to the reactive o-quinones. These latter can
appearance; as well as the generation of characteristic undergo reaction with amino acids to form brown addi-
aroma compounds. In unfermented teas, green notes tion compounds or polymerize to form complex colored
predominate; whereas in fully fermented teas, aroma polyphenols. Though not characterized in taste terms,
notes associated with Strecker/Maillard reactions, as well these compounds contribute at least to the color of the
as carotenoid scission products appear cured vanilla bean. In tea, the theaflavins and thearubigins
• The absence or length of the firing and drying stages. are mostly responsible for tea color and taste/mouth-feel.
Firing and drying stages enhance Strecker/Maillard reac- Molecular oxygen is required for such reactions to occur.
tions and potentially other chemistries. The o-quinones can additionally co-oxidise mono-phenols,
such as vanillin or guaiacol, to carbon linked dimer and
Opportunities in Vanilla Curing trimers with known taste/mouth-feel character. In addition,
Traditional vanilla curing in processing terms has evolved POD can oxidize mono-phenols to C-C linked di-phenols.
into a fairly standard operation, as exemplified by the The processing of vanilla beans is a fairly unchanged
Bourbon process, which is virtually and universally adopted series of operations which realize a general uniformity
[37]. Despite this process constancy, there is little control of flavor composition with some variability due to laxity
or management of the individual stages of the operation in process control. Tea processing exhibits a flexibility
leading to variability in product quality that manifest in part resulting in virtually unprocessed white tea through to
as reduced levels of vanillin. Tea processing, on the other extensively treated black tea. Key features of this range of
hand, provides a selection of tea product types reflecting the options include the extent of cellular damage, the absence
processing variable outlined above. or extended fermentation stage and finally the degree of
Opportunities for novelty in vanilla curing can be evaluated heating and its intensity. Opportunities exist to model some
with processing regimes based on tea treatments as follows: vanilla curing operations on the spectrum of interventions,
which represent tea processing. The ingenuity of vanilla
• Limited damage to the ripe vanilla bean followed by curer can realize new directions for vanilla flavor based on
drying to remove moisture. Color would be green and exploitation of tea processing.
with aroma characteristic of the ripe bean and processing
is equivalent to that of white tea. Acknowledgements
• Limited damage to the ripe vanilla bean followed by This paper recognizes the efforts of all the scientists
heating/drying to give the equivalent of green tea. Color and technologists whose knowledge and enthusiasm have
would be expected to be green to slight brown with brought us to our current understanding of the complexities
aroma characteristic of the green bean with perhaps of tea and vanilla chemistry, biochemistry and processing.
some phenolic notes.
• Extensive pod bruising or cutting followed by a short
References
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heating/drying operation. This would be equivalent to 1. N Subramanian, P Venkatesh, S Ganguli and VP Sinkar, Role of polyphenol
oolong tea production. Color would be brown with aroma oxidase and peroxidase in the generation of black tea theaflavins, J. Agric.
Food Chem., 47 (7), 2571-2578, (1999).
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indication of caramellic notes. 2. R Kusano, Y Matsuo, Y Saito and T Tanako, Oxidation mechanism of black
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• Extensive maceration of the whole vanilla bean followed (2015).
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elevated and extended heating would be invoked. The produced during processing of tea and selected foods, Int. J. Mol. Sci.,11,
product would be expected to be dark brown in color 14-40, (2010).
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Application Publication, US 2011/0081448 A1, Apr. 7, 2011. Wellness, 4 (1), 9-27, (2015).
9. P Dunphy, An evaluation of vanilla flavour and curing, Flavour Horizons, 29. AK Sinha, YK Sharma and N Sharma, A comprehensive review on
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Sci. Technol., 41, 1372-1379, (2008). Robles-Olvera, MA Garcia-Alvarado and Z Gunata, GC-MS and GC-
olfactometry analysis of aroma compounds in a representative organic
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41
A
n animated, moustachioed man with slightly
ruffled ginger hair works his way up and
down a conference room packed full of
delegates. He tells us: “dl-menthol really
is the neglected baby of the fragrance
industry.” We are at the 2016 British Society
of Perfumers annual symposium and Wolfgang Krause,
Ph.D., is presenting for BASF.
Wolfgang’s inimitable style has everyone engaged. People
are guffawing on cue and intently listening to a presentation
on materials that were already familiar to this room full of
seasoned perfumers. It is clear that Wolfgang would have
done well, had he chosen to become a chemistry teacher.
There is a reason he speaks of menthol with the same love
and enthusiasm people usually reserve for their children.
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
42 Fragrance Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
finally led to my decision to enter BASF in the same field of If you want to be an inventor, chemistry
vitamin synthesis. Indeed, sometimes there are very narrow
decision trees...” is the perfect career. You can find
“Of course the wall came down shortly after I left Berlin something absolutely new.
– and people sometimes ask me: would you have left if you
had known? I answer yes, absolutely. The wall had already chemistry is the perfect career. You can find something
left its mark.” absolutely new.”
Of course young Wolfgang set about exploring everything
Cloudy With the Chance of Aldehydes he had to hand around the house first.
Wolfgang’s passion for chemistry was ignited by an inno- “I took sugar and fermented it on the bench. Then I used
cent childhood gift of a chemistry set. drops of the alcohol to make some aldehydes and felt very
“I got the set at the age of about 14 or 15 and it was a happy with myself,” Wolfgang laughs. “After that I tried to
very creative tool - it was a little bit challenging; the results extract some materials from plants.”
were not so obvious. This is the right sort of thing for people This interest in plants and their chemistry led Wolfgang
who want to be inventors. If you want to be an inventor, to study organic chemistry with a very specific focus on
43
total synthesis, isolation and issues around sesquiterpenes “Over the last 20 years, Francis has taught me a lot about
during his time at the Technical University of Berlin. His fragrance – he has 50 years of experience and knows so
experiments there mainly based on geraniol and citral which much. We have become good friends,” explains Wolfgang.
naturally gave him an interest in fragrance chemistry and Part of Wolfgang’s current role involves creating demon-
gave him the foundation for his later work on citral. stration formulas for presentations of fragrance materials
to perfumers, but he absolutely does not consider himself a
The Chemistry of Perfumery perfumer.
When Wolfgang joined BASF in 1989, he went into “In terms of education and skills there might be some
developing intermediates for vitamin synthesis. “This is not parallels, of course,” says Wolfgang, “but I like the clear
so far from fragrance materials,” says Krause, “and those segmentation of professions. I have a deep respect for per-
days I had colleagues who worked on menthol, which meant fumers; a deep respect for their talent. It’s a very traditional
I was always in contact with fragrance and flavor chemists.” art. Fundamentally, there is a different approach to how
In 1995, Wolfgang joined the aroma ingredients division chemists and perfumers view the world, though—a per-
and became far more involved with technical marketing fumer is looking at things from an artistic and commercial
and R&D projects for aroma. “We had a very broad port- perspective—they would like to have the next best seller. A
folio. This was not easy to handle, I would almost call it a chemist would want to one day win the Nobel prize.”
learning phase for me to focus on important large volume As a chemist working closely with perfumers, Wolfgang
products. This finally led to many product launches for is very well versed in the sometimes subtle technical details
important ingredients. And from that moment on, my that can alter the quality of a finished product. Everyone
passion for fragrances began. talks about getting the best quality and best ingredients, but
Wolfgang made contact with an external perfumery this is sometimes erroneously attributed to price alone.
consultant living in the south of France, who turned out to To create a beautiful rose accord, you need a consistent
be the master perfumer, Francis Bocris. high quality geraniol. And depending on your feedstock,
A cool type of chemistry: Wolfgang and his team developed a completely new synthesis route for menthol from citral.
45
The German Association of Perfumers, (Deutsche Gesellschaft der Parfümeure, DGP), which Wolfgang serves as current president, advocates active participation
in educating both the industry and the public in perfumery.
communicating about perfumery and science to a number experience of menthol’s deep cooling effect which becomes
of different audiences. apparent after two minutes. I still recall the ‘OOOOO!’
“I cannot really resist the opportunity to do a presenta- sound he made and the sounds from the room when he also
tion and to work closely together with our colleagues all didn’t believe me when I told him that applying chilli on the
over the world. Ten years ago I was very heavily involved in affected area would not, in fact, cancel out the effect, but
India, and India has a really great spirit of perfumery that only make it worse as your receptors would just get over-
a lot of us here in the West are not so aware of,” explains whelmed. So he got the second lesson shortly after.”
Wolfgang. By the end of our interview, Wolfgang has shared many
“To see other cultures in perfumery is very important,” anecdotes from his life and career. His passion for chemis-
he adds. try, invention and adventure shines through. He is clearly
“Learning the use of different materials alone – for not just a working chemist and a supporter of perfumery,
example, the Japanese are totally different from the Chinese but very much an advocate for science communication, too.
in how they react to different scents.” I ask him what the biggest lesson he himself has learned
“In 2011, I was doing a road show in Tokyo and there during his career.
was a very nice Japanese man in the audience during my “Oh, I hope that is yet to come,” Wolfgang says and laughs.
menthol presentation who used a menthol sample like an
aftershave and after two minutes of silence, we all heard To purchase a copy of this article or others,
a big ‘WOW’ from the back. He basically got first-hand visit www.PerfumerFlavorist.com/magazine.
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Organoleptic Characteristics
of Flavor Materials
n BY JUDITH MICHALSKI, Senior Flavorist, abelei flavors; jmichalski@abelei.com
d—Tridecalactone
Source: Sigma
FEMA# 4685, CAS# 73370-92-5
Source: Omega Ingredients Natural occurrence: Not yet found in nature.
GRAS, natural Odor: @ 100%. Sweet, milky, oily, creamy and fatty with a
Odor: @ 100%. Green, earthy, musty, sweet, vegetablelike hint of peach.
and raw pea. Taste: @ 5 ppm. Creamy, milky, and oily with a fatty
Taste: @ 0.2%. Green, earthy and fresh. mouthfeel.
Possible applications: This product will add a distinctive fresh, Taste: @ 10 ppm. Creamy, oily, slightly peach/coconutlike
earthy top note to vegetable flavors like pea, corn, radish, with a fatty mouthfeel.
cauliflower, broccoli, cabbage, wasabi and their blends. Possible applications: The delicate nature of this lactone will
Omega Ingredients: www.omegaingredients.co.uk/home add subtle, creamy, milky notes to all dairy flavors includ-
ing milk, cream, butter, fresh cheeses and yogurt. Its
Boronia Leaf Absolute addition to nut flavors like macadamia, cashew, pecan and
Source: Essential Oils of Tasmania peanut and fruits like mango, peach, apricot, papaya will
FEMA# 2167, CAS# 91771-36-7/8053-33-6, natural, complement the fatty notes without being obvious.
Boronia megastigma Nees Sigma: www.sigmaaldrich.com
Odor: @ 100%. Green, fresh, woody, leafy and melon/
cucumberlike. Theaspirane
Taste: @ 2 ppm. Green, sweet, melon/cucumberlike and Source: Charkit
vegetablelike with a trigeminal tingle. FEMA# 3774, CAS# 36431-72-8
Taste: @ 4 ppm. Green, vegetablelike , melon/cucumberlike Natural occurrence: Blackberry, grape, guava, tea, passion
and slightly pepperlike with a trigeminal tingle. fruit, raspberry and osmanthus.
Odor: @ 100%. Sweet, cooling, eucalyptollike, spicy, clovelike
1 Green Pea KiiNote is a registered tradename of Omega Ingredients and woody.
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2016 Allured Business Media.
48 Flavor Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
YEARS OF
ARTICLES
At your fingertips when you subscribe online
www.PerfumerFlavorist.com
Taste: @ 0.5 ppm. Slightly cooling, camphoraceous, green, Pyrazines Mix #36 Natural
minty and slightly spicy.
Taste: @ 1 ppm. Cooling, camphoraceous, spicy and clovelike.
Possible applications: This material will provide a subtle,
cooling lift in spice flavors like clove, anise, cinnamon,
ginger, black pepper and their blends. Other flavors
where it will add interest are gin, berries and tea.
Charkit: www.charkit.com
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
52 Ingredients Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
53
lavandulyl acetate (<0.1–1.6%) from the vicinity of Bizerte (Tunisia) p-cymene (1.5%)
hexyl tiglate (<0.1–0.8%) were air-dried and subjected to steam 1, 8-cineole (11.7%)
neryl acetate (<0.1–0.9%) distillation for 2½ hrs by Alatrache (E)-b-ocimene (0.8%)
hexyl hexanoate (<0.1–0.2%) g-terpinene (0.3%)
etal. (2007). The resulting oil that was
b-caryophyllene (0.2–2.2%) fenchonea (0.7%)
produced in 2.4% was analyzed by
coumarin (<0.1–2.4%) linalool (32.6%)
trans-a-bergamotene (<0.1–0.2%)
GC-FID and GC/MS. The constitu- a-campholenal (0.3%)
a-humulene (0.1–0.5%) ents characterized in this oil were: camphor (12.4%)
(E)-b-farnesene (<0.1–4.8%) isoborneol (0.1%)
germacrene D (<0.1–1.0%) a-thujene (0.1%) lavandulol (8.7%)
(Z)-a-bisabolene (0.3–2.1%) a-pinene (0.7%) terpinen-4-ol (7.7%)
b-bisabolene (<0.1–0.5%) camphene (0.7%) a-terpineol (1.5%)
(E)-a-bisabolene (<0.1–2.3%s) sabinene (0.1%) myrtenol (<0.1%)
g-cadinene (0.1–0.8%) b-pinene (1.6%) cis-carveol (0.5%)
d-cadinene (<0.1–1.0%) myrcene (1.1%) a-fenchyl acetatea (0.2%)
caryophyllene oxide (<0.1–2.4%) a-phellandrene (0.3%) methyl carvacrola (1.9%)
T-cadinol (<0.1–0.5%) d-3-carene (0.5%) linalyl acetate (1.8%)
a-cadinol (<0.1–0.2%) 1, 4-cineole (0.1%) bornyl acetate (4.2%)
a-bisabolol (<0.1–2.6%)
f = furanoid form
T-1. Comparative percentage composition of the leaf and flower oils of spike
For comparison purposes, the data lavender of Spanish origin
presented in the ISO Mongraph (1996)
for spike lavender oil is as follows: Compound leaf oils Flower oils
a-pinene 0.1 0.5–1.8
limonene (0.5–3.0%) camphene 0.2–0.4 0.3–0.5
1,8-cineole (20.0–35.0%)
camphor (8.0–16.0%)
b-pinene 0–0.1 0.8–2.9
linalool (30.0–50.0%) sabinene – 0.3–1.0
a-terpineol (0.5–2.0%) 1-octen-3-ol 0.1–0.2 0.2–0.3
linalyl acetate (t–1.5%)
myrcene – 0.5–1.0
(E)-a-bisabolene (0.5–2.5%)
a-terpinene – 0–0.1
t = trace (<0.1%)
p-cymene 0.3–0.4 0.1–0.2
limonene 0–0.1 0.2–0.9
R.ter Heide (1985) examined the
headspace of Spanish spike lavender 1,8-cineole 46.8–54.6 20.8–47.9
oil and characterized acetaldehyde, g-terpinene 0-0.1 0.1–0.2
butanal, isobutanal, 2-methylbutanal, terpinolene – 0.1–0.3
valeraldehyde, isovaleraldehyde, cis-sabinene hydrate 0.1–0.2 0.3–1.1
hexanal, (E)-2-hexenal, ethanol,
linalool 0–0.1 15.1–54.7
isopropanol, isobutanol, 2-butanol,
1-penten-3-ol, 2-methyl-3-buten-2-ol, trans-pinocarveol 0.5–1.2 0.1–0.3
hexanol, isopropyl formate, hexyl cis-verbenol 0.1–0.2 0–0.1
formate, ethyl acetate, allyl acetate, camphor 31.5–43.5 11.4–18.6
2-butyl acetate, butyl acetate, hexyl borneol 1.8–2.7 0.9–1.8
acetate, methyl butyrate, acetone,
lavandulol 0.4–1.0 0.2–0.3
2-butanone, 3-buten-2-one, 2-pen-
tanone, 3-methyl-2-butanone, a-terpineol 0–0.1 0.6–2.2
3-hexanone, 2-methyl-3-pentanone, myrtenal 0.1–0.2 0.2–0.3
4-methyl-2-pentanone, 2-methyl- myrtenol 0.1–0.2 0.1–0.2
1-penten-3-one, 3-octanone, hexyl 2-methylbutyrate – 0–0.1
2-methylfuran, 3-methylfuran, 2-eth-
geraniol 0.3–0.5 0.1–0.4
ylfuran, 3-isopropylfuran, hexyl methyl
ether, isoprene and toluene as head- geranyl acetate – 0.1–
space volatiles. b-caryophyllene 0.1-0.2 0.5-1.1
The flowering heads of spike caryophyllene oxide 0.2-0.7 0.2-0.7
lavender plants that were collected
55
sabinene (0.7%)
b-pinene (2.1%)
T-3. Comparative percentage composition of the volatiles of spike lavender
myrcene (0.5%)
produced by three different methods
limonene (0.5%)
1,8-cineole (30.7%)
(Z)-b-ocimene (0.3%) Compound 1 2 3
cis-sabinene hydrate (0.9%) a-pinene 1.5 1.3 1.1
linalool (36.4%)
camphor (13.1%) camphene 0.6 0.5 0.4
borneol (0.7%) sabinene 0.6 0.4 0.5
d-terpineol (0.3%) b-pinene 2.0 1.7 1.5
terpinen-4-ol (0.5%)
a-terpineol (1.1%) myrcene 0.5 0.4 0.4
b-caryophyllene (1.3%) a-terpinene 0.2 0.2 t
(E)-b-farnesene (0.3%)
p-cymene 0.2 0.2 t
germacrene D (0.5%)
b-bisabolene (0.3%) 1, 8-cineole + limonene 38.0 42.6 37.4
(E)-a-bisabolene (1.7%) (Z)-b-ocimene 0.3 0.2 0.2
caryophyllene oxide (0.5%)
g-terpinene 0.3 0.3 t
a-bisabolol (1.8%)
T-cadinol (0.3%) cis-sabinene hydrate 0.6 0.3 1.3
cis-linalool oxidef t 0.2 0.4
In addition, trace amounts (<0.1%) trans-linalool oxidef t 0.1 0.4
of p-cymene, (E)-b-ocimene, g-terpi- terpinolene 0.3 0.2 t
nene, terpinolene, cis-linalool oxide and linalool 35.8 34.4 32.6
trans-linalool oxide (furanoid forms),
a-campholenal 0.2 0.1 0.1
cryptone, linalyl acetate, hexyl butyrate,
hexyl isobutyrate, hexyl 2-methylbu- nopinone 0.1 0.1 0.2
tyrate, bornyl acetate, lavandulol and trans-sabinol 0.4 0.2 0.3
trans-a-bergamotene were also listed as camphor 8.6 9.1 9.0
constituents of this oil. pinocarvone 0.4 0.3 0.4
Spike lavender plants that were
harvested in full flower from an experi- borneol 2.2 2.2 2.5
mental garden in Segeza (Foggia, Italy) terpinen-4-ol 0.5 0.7 0.3
were hydrodistilled (the flowers only) a-terpineol 1.0 0.9 1.0
for 3hr by Fiocco etal. (2011). Analysis myrtenal 0.5 0.5 0.6
of the oil by GC-FID and GC/MS
verbenone 0.1 0.2 0.5
revaled that it possessed the following
composition: trans-carveol 0.1 0.1 0.2
isobornyl formate 0.2 0.1 0.1
a-thujene (0.2%) hexyl 2-methylbutyrate 0.1 0.1 0.3
a-pinene (0.7%)
camphene (0.4%) hexyl isovalerate 0.1 0.1 0.1
sabinene (0.3%) b-caryophyllene 0.8 0.3 2.2
b-pinene (0.6%) (E)-b-farnesene 0.2 0.1 0.8
3-octanone (0.2%)
myrcene (1.0%) germacrene D 0.3 0.1 1.3
a-phellandrene (0.1%) g-cadinene 0.1 t 0.3
d-3-carene (0.2%) caryophyllene oxide 1.2 0.6 1.2
a-terpinene (0.1%)
p-cymene (4.7%) ledol 0.1 t 0.1
1,8-cineole (11.0%) a-muurolol 0.6 0.3 0.6
(Z)-b-ocimene (1.3%) a-bisabolol 0.8 0.3 1.0
(E)-b-ocimene (1.3%)
g-terpinene (0.4%) t= trace (<0.1%)
terpinolene (0.4%) f = furanoid form
hydrodistilled oil
1-octen-3-ol (0.6%)
microdistilled oil
linalool (44.5%) methylene chloride extract
camphor (3.6%)
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terpinen-4-ol (9.8%) the volatiles from the three isolation and its relation to their ecological areas.
borneol (10.9%) Biochem. Syst. Ecol., 35, 479–488 (2007).
procedures.
a-terpineol (0.9%) M. H. Eikani, F. Golmohammad, S.
lavandulyl acetate (1.3%) Shokrollahzadeh, M. Mirza and S.
Spike lavender oil. In: Progress in Essential oils.
geranyl acetate (0.7%) Rowshanzamir, Superheated water extraction
Perfum. Flavor; 3(3) 48–49 (1978); 5(1), 58
b-farnesene* (0.7%) of Lavandula latifolia Medik Volatiles:
(1980); 5(2), 38(1988); 8(5), 20–22(1983);
Comparison with conventional techniques. J.
9(1), 56(1984); 12(5), 62 (1987); 15(5),
*correct isomer not identified Essent. Oil Res., 20, 482–487 (2008).
58–59(1990); 18(6), 53(1993); 26(3,
75–76(2011); 31(7), 47–48 (2006). D. G. Williams, The Chemistry of essential oils.
2nd Edn., pp. 188–189, Micelle Press, Port
The volatiles produced from spike R.ter Heide, Concentration of odorous headspace
Washington, NY (2008).
lavender plants, that were harvested volatiles. In: Essential oils and Aromatic
Plants. Edits, A. Baerheim Svendsen and D. Fiocco, D. Fiorentino, L. Frabbori, S.
in full flower, by hydrodistillation, J. J. C. Scheffer, pp. 43–60, Martinas Benvenutti, G. Orlandi, F. Pellatti and A.
microdistillation and methylene Nijhoff/D.W. Junk Publishers, Dordrecht, Gallone, Lavender and Peppermint essential
chloride extraction were the subject of The Netherlands (1985). oils as effective mushroom tyrosinase
inhibitors: a basic study. Flav. Fragr. J., 26,
a study by Mendez-Tovar et al. (2015). ISO No. 1668 Essential oils. Oil of Spike lavender 441–446 (2011).
The comparative results determined [Lavandula latifolia (Linnaeus fils) Medikus.
(1996). I. Mendez-Tovar, S. Sponza, C. Asensions-
using GC-FID and GC/MS as their Manzanera, C. Schmiderer and J.
method of analysis can be seen in T-3. A. Alatrache, B. Jamoussi, R. Tarhouni and M. Novak, Volatile fraction differences for
In addition trace amounts (<0.1%) of Abdrabba, Analysis of the essential oil of Lamiaceae species using different extraction
Lavandula latifolia from Tunisia. J. Essent methodologies. J. Essent oil Res., 27,
tricyclene, a-thujene, thuja-24(10)- Oil Bear. Plants, 10, 446–452 (2007). 497–550 (2015).
diene, a-phellandrene, (E)-b-ocimene,
J. Munoz-Bertomeu, I. Arrillaga and J. Segura,
cis-p-menth-2-en-1-ol, hexyl butyrate Essential oil variation within and among To purchase a copy of this article or others,
and d-cadinene were also found in natural populations of Lavandula latifolia visit www.PerfumerFlavorist.com/magazine.
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62 Endpoint Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
M
usic can be one of life’s
most influential sensory
experiences, crescendoing
its way into our neuronal
networks and very being. It
evokes deep emotion, stirring
up old memories or giving us
new hope.
Music influences the way we think. In fact, many great
scientists have a musical or artistic hobby. Coincidence? I
doubt it, especially considering all the recent work happen-
ing in the realm of cross-modal perception and synesthesia.
Listening to Texture
According to another source, RT, which also reported
on this paper, Felipe Reinoso Carvalho, co-author of the
study, said that the experiment showed that sound not only
63
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