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January 2017 | Vol. 42 no.

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.

PF1701_cover_final.indd 1 12/16/16 4:24 PM


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84900

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CONTENTS VOL. 42, NO. 1 | JANUARY 2017

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.

22 Flavor Bites: Geraniol


The rose character of geraniol is very bright and fragrant,
but it also possesses considerable depth, which is especially
helpful in flavors.
By John Wright

48 Organoleptic Characteristics of Flavor Materials


This month’s column features organoleptic discussions on
22 Boronia leaf absolute, theaspirane, white cognac oil, pyrazine
mix #36 natural and more.
By Judith Michalski

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

52 62 Endpoint: Synesthesia is Music to our Taste Buds


How can sound influence the way we smell and taste? Research
in cross-modal perception and synesthesia is offering innovative
answers in creating richer, more engaging products in F&F.
By Rachel Grabenhofer

INGREDIENTS
20 Raw Material Bulletin

26 Tea Leaf and Vanilla Pod: Commonalities in Chemistry,


Biochemistry and Processing
62 Using a multidisciplinary approach to better understand the
ripening and senescence processes of tea and vanilla, the
authors propose the development of milder processes for
natural materials.
By Patrick Dunphy, Ph.D. and Krishna Bala, Ph.D.

52 Progress in Essential Oils


Spike lavender oil.
By Brian M. Lawrence

2 Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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EDITORIAL

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
Rachel L. Grabenhofer, Managing Editor • 1-630-344-6072/rgrabenhofer@allured.com
Nicole Urbanowicz, Research Analyst • 1-630-344-6053/nurbanowicz@allured.com
Jennifer Novoseletsky, Assistant Editor • 1-630-344-6045/jnovoseletsky@allured.com
Savannah Saunders, Assistant Editor • ssaunders@allured.com
Brooke Schleehauf, Assistant Editor • 1-630-344-6032/bschleehauf@allured.com
Lisa Schryver, Assistant Editor • 1-630-344-6068/lschryver@allured.com
Ryan Daily, Digital/Social Media Editor • 1-630-344-6058/rdaily@allured.com
ADVERTISING SALES
Paige Crist, Associate Publisher/ Flavorcon & World Perfumery Congress Exhibits &
Sponsorship • 1-630-344-6060/pcrist@allured.com
Kasia Smialkowski, Coordinator • 1-630-344-6025/ksmialkowski@allured.com
AUDIENCE DEVELOPMENT

48
Linda Schmitt, Director
Marie Galvan, Marketing Specialist
Alyssa Howard, Marketing Assistant
Customer Service • 1-866-366-9220/customerservice@perfumerflavorist.com

DESIGN
Lisa Hede, Graphic Design Manager
Hon Bannapradist, Senior Graphic Designer
Bryan Crowe, Production Manager
EVENTS
Sandy Chapin, Group Show Director
Mary Richter, Show Manager • 1-630-344-6023/mrichter@allured.com
Andrea Blood, Exhibits Coordinator • 1-630-334-6038/ablood@allured.com
Mark Rosenblum, Event Specialist • 1-630-334-6071/mrosenblum@allured.com
CORPORATE
Janet Ludwig, Partner & President
George Fox, Partner & CEO

INDUSTRY Linda Getner, Controller


Rose Southard, Digital Products Director
Maria Romero, Executive Assistant
6 Editor’s Note: A New Experience
What makes an F&F product memorable? Depth.
Layer. Texture. And its coinciding political climate.

8 Industry: News, Events and Analysis


SUBSCRIPTIONS
Perfumer & Flavorist magazine (ISSN 0272-2666) is published monthly by Allured Business Media.

19 Events Subscriptions: Subscribe online: www.PerfumerFlavorist.com/subscribe


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E-mail: customerservice@perfumerflavorist.com

61
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Other products brought to you by Allured:
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4 Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Editor’s Note

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?

MATTHIAS GUENTERT A Change of the Guards


Independent flavor consultant Last year marked an unprecedented election process in the United States
with the results leaving the country in a state of economic and political uncer-
BRIAN M. LAWRENCE tainty. Prior to the U.S. election, England waved goodbye to the European
Natural Products Editor, Union in its infamous Brexit vote. With two global powers undergoing a chang-
Perfumer & Flavorist magazine; ing of the proverbial guards, how will these changes affect the global F&F
Editor-in-Chief, industry in 2017?
Journal of Essential Oil Research The results of Brexit are still uncertain, however, changes in global trade
routes, labor flow and a possible tariff-free trade with the European Union are
JUDITH MICHALSKI to be expected. As a result of the exit strategy, the U.K.’s growth is projected
Senior flavorist, abelei flavors to decrease to 1.2% this year due to a downturn in business investments and
changes in trade relationships.a
LESLIE SMITH According to Euromonitorb, the U.S. GDP is predicted to slow down 0.3%
President, Leslie C. Smith Consulting in 2017, which is 1.8 points lower than the original baseline projected by the
firm. These figures are based on President-elect Trump’s proposed tax cuts,
JOSH VERNOSKI anti-immigration, renewable energy and trade relation policies.
Regulatory affairs manager, Despite these changes, the rise in political and economic uncertainty can
FONA International, Inc. be a strength for the F&F industry. It’s a new experience and an opportunity
for the industry as a whole to build stronger, more transparent supply chain.
JOHN WRIGHT Perhaps all of this change is the trigger for the next renaissance in the industry.
Independent flavorist and author Happy learning to you.

With warmth from New York City,

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

6 Editor’s Note Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Industry

World Essential Oil Market Expected to Reach $115 Billion by 2020


According to a report published by Allied Market of the overall market revenue, according to the report.
Research, the world essential oil market is expected to reach Orange essential oil is expected to remain the highest
$11.5 billion by 2022, with a compound annual growth rate contributor by 2022, with a projected CAGR of about 11
(CAGR) of 10.1 percent from 2016 to 2022. percent from 2016 to 2022.
Key driving factors include consumers’ rising preference From a growth perspective, the market for corn mint
for natural products, the growing popularity of relaxation essential oil is expected to register the highest compound
therapies, increasing dispos- annual growth due to its
able income resulting in increasing global demand
better standards of living, and thanks to its antibacterial
growing awareness of side properties and strong menthol
effects of chemical substances. aroma.
According to the report, Based on geography,
the spa and relaxation sector Europe dominates the essen-
is anticipated to grow at the tial oil market, accounting
highest CAGR of over 10 for around 40 percent of the
percent during the forecast overall revenue in 2015. The
period, followed by the food region is expected to maintain
and beverage, and medical its dominant position through-
sectors. The increase is due to the growing popularity of out the analysis period on account of the growing demand
spa and relaxation therapies coupled with increasing dispos- for natural cosmetic products, rising awareness and increas-
able income of the consumers in this area. Additionally, ing adoption of innovative essential oil solutions in varied
the superior antibacterial and antiseptic properties, and application sectors.
aromatic flavor of these essential oils have boosted their Europe is the dominant market and is expected to be
overall popularity. the leading contributor to the global revenue throughout
The essential oil market is highly dependent on the raw the reported period. The Asia-Pacific region is expected
material prices, which are expected to be steady in the near to record the highest CAGR during the forecast period,
future. Market growth has been fueled by the increasing owing to increasing demand for organic and natural beauty
use of essential oils in the spa, aromatherapy, flavoring and products in countries such as China and Japan, favorable
fragrance industries. government regulations and technological developments
In 2015, orange essential oil contributed the highest in production and extraction processes of essential oils,
revenue in the global market making up around 22 percent according to the report.

Symrise Introduces Sweet Modulators, Reduces Sugar by 35%


Under Symrise’s Taste for Life Platform, the creation of SymLife
Sweet, a sweetness modulator, offers sugar replacement into the beverage
segment. SymLife Sweet reduces 35% of sugar in a product in response
to consumer and retailer demand for viable sweet solutions without “high
intensity sweeteners with off-tastes,” explained Emmanuel Laroche, vice
president of Symrise’s marketing and consumer insights group and global
marketing leader.

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.

8 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Biolandes Buys Golgemma
In order to expand its range of organic products, Biolandes has
acquired Golgemma, a French company that produces vanilla, black,
white and pink pepper. Biolandes was founded by Jean-Claude Pichot
and Patrick Colin, two pioneers who are focused in aromatherapy.
Golgemma is a provider of more than 300 items in its catalog with 20
years of experience. With partnerships and expertise in organic prod-
ucts, Golgemma grew its company in order to include vegetable oils,
hydrolates and organic spices to its knowledge.
Establishing a long-standing goal in 2012, Golgemma established
a direct tie with Madagascar by installing a processing facility for
ingredients. The company took over the management of farm produc-
ing ylang-ylang, vetiver and palmarosa in 2015.

So, What’s the Plan for Biolandes?


Golgemma earned 20 ESR-certified products, which is what
interested Biolandes the most. The company’s ambition is to develop
new ESR channels and with the acquisition of Golgemma, Biolandes
purchased clientele that were ready to pursue the approach. Both
Pichot and Colin will also be working with Madagascar to complete a
smooth integration in order for the growth of Biolandes to continue.

Nick Pickthall Joins IFRA UK as Agilex Strategically Acquires


New Chairman Creative Fragrances
After joining CPL Agilex Fragrances, a company that provides air
Aromas 16 years ago, care, home care, personal care and fine fragrances,
Nick Pickthall has been has recently purchased Creative Fragrances in order
selected as the chair- to continue to grow as a middle market fragrance
man of IFRA UK. company in the U.S. The company is trying to grow its
Pickthall has worked presence in certain geographic areas in order to make
in key management its product lines available to new groups of fragrance
positions at CPL clients.
Aromas for the past 16 President Craig Neely said, “Everyone at Creative
years, and most recently Fragrances Ltd. appreciates the trust our customers
as the COO where he has have placed with us in the past, and firmly believes that
worked in the United States, Agilex’s unique combination of large company resources
United Kingdom and South America. and small company values makes them the perfect
His role as the chairman for IFRA UK is an honorary partner. Agilex offers the highest quality fragrances,
position, and a new one for the trade association. world-class customer service, comprehensive regulatory
Pickthall will uphold IFRA UK’s mission to support, and superior manufacturing capabilities. There
develop and advance the fragrance industry by will be a seamless transition. We are also very excited
encouraging members to maintain high standards that our clients have now immediate access to the
and working practices. additional expertise and resources of Agilex.”

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Industry

IFF Q3 Results Show Growth and Decline


Throughout the third quarter of IFF’s financial and
strategic accomplishments, the reported net sales reached
$777 million, showing a 2% improvement from last year’s
third quarter. Also, currency neutral sales increased 3% due
to the acquisition of Lucas Meyer Cosmetics.

Financial Gains and Losses


IFF also experienced losses throughout the third quarter
in both operating profit and earnings per share (EPS). The
company recorded $124.3 million this year compared to the
$156.7 million from last year. The currency neutral adjusted
the operating profit with a 4% decrease. The EPS was
recorded at a $1.31 per diluted share in 2015 while this year’s
record has noted a 1% drop down to $1.12 per diluted share.

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.

Jennifer Beltz Joins FEMA


Jennifer Beltz has been hired by FEMA as the director of communications
to work with members and staff to help with strategic communication, PR
and media relations. Previously, she served as the head of communication of a
global software association.
Beltz has also had experience as a manager of a gubernatorial campaign,
a leader of public affairs at the health company Best Doctors, Inc. and ran a
boutique firm’s PR for several years. In the upcoming months, Beltz will be
attempting to reach out to members and ensure their understandings are up
to speed of what the companies’ issues and policies are.

Photo courtesy of FEMA.

10 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Biolandes Expands in Madagascar ACI Welcomes New President and CEO
with Acquisition From the American Fuel &
Petrochemical Manufacturers,
Melissa Hockstad comes well
prepared to ACI, ready to
accept her new position as
president and CEO on January
1, 2017. She will be replac-
ing Ernie Rosenberg, who has
accepted an advisor position
until January 2018.
Hockstad served as vice
president for seven years at
the American Fuel & Petrochemical Manufacturers and
as vice president of the material suppliers council and vice
On October 5th, 2016, Biolandes group acquired French president of science, technology and regulatory affairs at the
company Golgemma. Golgemma, a supplier of certified Plastics Industry Trade Association.
organic essential oils, has more than 300 items in their “The Board of Directors believes that Melissa Hockstad
catalog and connections to raw materials in Madagascar. will be a strong, dynamic, and forward-thinking leader for
ACI, building upon the wonderful foundation that already
Madagascar’s Raw Materials exists at the association,” said Tom O’Brien, ACI board
In 2012, Golgemma installed vanilla, pepper (white and chair and senior vice president, Performance Chemicals,
black) and pink pepper processing facilities in the country. Sasol. “This strong foundation is because of the terrific
Then in 2015, Golgemma took over management of a farm work done for many years by Ernie Rosenberg and the
producing ylang-ylang, vetiver and palmarosa. This has amazing staff at ACI.”
enabled Golgemma to set-up purchasing channels that meet Hockstad also brings five years of director experience
Ecocert’s ESR criteria, enabling Golgemma to offer 20 from her time as director for Performance Improvement at
ESR-certified products. the Synthetic Organic Chemical Manufacturers Association.
Biolandes hopes that with this acquisition it will help She began her work into the field when she was awarded her
expand its range of organic products and lead to more ESR- B.S. in engineering science from the University of Virginia
certified supply channels. and an M.S. in materials science and engineering.

Sustainability in Madagascar’s Supply Chain


Since 2015, The Sustainable Vanilla Initiative (SVI) goal
has been to help improve vanilla bean farmers’ livelihoods
and assure the quality of natural vanilla. In addition to this,
they have attempted to address over-arching issues facing
the international vanilla bean community such as price
volatility, falling quality, and insufficient product traceability.
The SVI represents 70% of worldwide vanilla bean pur-
chasers which currently include 20 members ranging from
major consumer good manufactures to global fragrance
and flavor companies. There has been a special focus on
Madagascar, which represents 80% of the world supply of
vanilla bean.
Additionally, the SVI in conjunction with the
Improving Conditions for Partners International Labor Organization received a grant for $4
Despite only being active for two years, the SVI has million in 2016 by the U.S. Department of Labor to prevent
already made progress with its goals. In 2016, it helped child labor, improve sector governance and traceability and
created a Code of Conduct for Malagasy vanilla market assist grower groups.
participants.

11

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Industry

Earthoil Contributes 3,000 Liter Water Tanks to Farmers


In the next three years, Earthoil will be providing 3,000-liter water tanks
to 615 farmers to the Kenya Organic Oil Farmers Association. The first 40
tanks have just been installed for tea tree farmers in Kenya. This is just the
beginning as Earthoil will be helping more than 2,000 family members of
the farmers.

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).

How Will Sustainability Goals of Big Retailers Affect F&F?


Walmart has updated its sustainability plan to
promote locally grown, fresh foods and encouraging sup-
pliers to use 100% recyclable packaging. The company
intends to produce half of its energy from renewable
sources by 2025 and will reduce its greenhouse gas emis-
sions by 18% and one gigaton by suppliers in 2030.
So what does this mean for the flavor industry? As
Walmart pushes for a more sustainable, supply chain
(with a goal to be the most affordable and sustainable by
2025), the trend is likely to affect competing retailers,
consumer packaged goods companies and flavor houses.
In order to keep up with the sustainability trend, the
F&F industry is challenged to improve its formulations
to keep up with retailers’ agendas.
However, as more consumers are concerned with
natural products, the industry is faced with pressing
regulatory issues on ingredient safety. The Federal Drug
Administration (FDA) is continuing to narrow down
its definition of what is “natural,” while the industry,
retailers and consumers continue to hold their breath.
How can the industry communicate that natural does not
necessarily equate safe? These bridges in understanding
could certainly affect the sustainability agendas of both
industry and retailers alike.

12 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Industry

Frutarom Makes Eighth Acquisition, DuPont Tate & Lyle Celebrate 10 Years,
Purchases Piasa Expand Facility

Celebrating 10 years of shipping biomaterial, DuPont


Tate & Lyle have announced an expansion that will increase
its Loudon, Tennessee facility by 35% and will source its
products to customers around the globe through the con-
sumer and industrial market segments.

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.”

14 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Smell the Perfume at the Grand Musée du Parfum
The Grand Musée du Parfum in Paris will open
December 16, 2016, providing an interactive experience for
guests to learn about the history and craft of perfumery. The
building was previously owned by French fashion house,
Christian LaCroix.
The 1,400 square meter space is supported by Syndicat
français de la parfumerie (SFP). International Flavors
and Fragrances (IFF) designed the “sceneography” which
entails a full sensory immersion for guests. Attendees are
provided the opportunity to discover an olfactory collection
of more than 60 scents. Aside from learning the history,
experiencing sensory immersion and understanding the craft
behind the world’s most famous perfumes, guests will leave
with their own perfumed business card.

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

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Industry

Natural Fragrance Ingredient Market Worth $5.3 Billion by 2024


According to a recently released report from the
Transparency Market Research (TMR), it was estimated
that by 2024 the natural fragrant ingredient market will be
worth $5.3 billion.

Middle Class Demands Naturals


One of the main drivers for growth has been the
European natural fragrance ingredient market. This region
is expected to acquire 29.74% of the overall market share by
2024, with a progress of 6.5% CAGR during the period.
This is directly attributed to consumers’ sentiment
moving towards products that are naturally sourced. In addi-
tion, the rise of globalization and urbanization has expanded extracting raw ingredients are expected to damper some of
the middle class, which generally have more disposable the potential growth.
income to buy personal care products and fine fragrance. However, efforts have been made globally to address
these issues, such as the SVI investing in Madagascar and
Overcoming Environmental Concerns industry efforts in sustainable sourcing.
Despite the increase in demand, this growth isn’t without
its struggles. Environmental issues and the high cost of

TFS Corporation to Partner with Young Living Essential Oils


TFS Corporation and Young Living Essential Oils have partnered together to provide
Young Living with double its production of sandalwood oil in order to meet the current and
future demands of the market. TFS’ sandalwood oil will complement the company’s existing
supply of Royal Hawaiian Sandalwood from its partner in Hawaii.
“We admire TFS’ commitment to high quality, sustainably grown sandalwood,” said Jared
Turner, Young Living chief operating officer. “Its practices align with our commitment to
stewardship of the earth and follow our strict ‘Seed to Seal’ standards for quality.”

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.”

16 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Industry_fcx.indd 16 12/16/16 3:10 PM


Flavorist Profile: Gail Underwood
In this exclusive interview with Perfumer & Flavorist, Underwood shares her experience on
the evolving flavor industry, creativity in formulations and why we need flavors in products.

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.

Perfumer & Flavorist: You can see the pattern here


of smaller companies being taken over through the
years. It’s remarkable to see how the industry land-
scape changes through these acquisitions.
Gail Underwood: That’s one of the biggest changes the analytical techniques we have now, it makes it easier, but
I’ve seen are these company takeovers. Companies that had years ago you didn’t have that. It was really down to the skill
major names, like Fritzsche, all got swallowed up basically. of the flavorist.

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

PF1701_Industry_fcx.indd 17 12/16/16 3:10 PM


Industry

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

18 Industry Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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manufacturers have their own idea what they want and
don’t want. You have to be wary of that. That can sometimes
restrict you a bit. If a company just wants natural products
Events
you don’t always have the availability of the raw materials More events are posted at www.PerfumerFlavorist.com/
that will make the best products, so you’ve got to be creative events. Filter events by topic and region; submit event
to make it the best you possibly you can without having announcements; access exclusive event coverage and
access to key raw materials that you may have in a non- photo albums.
natural form.

P&F: Right. The buzzword along with “natural” is 2017


“safety.” As these labels are growing more transpar- January 19—Society of Flavor Chemists Meeting;
ent and consumers are paying more attention to what Los Angeles, CA; www.flavorchemists.com
they’re consuming, the safety of these ingredients is
put into question. February 7–9—FEMA Winter Regulatory + Policy
Conference; Baltimore, MD; www.femaflavor.org/events
GU: Yes, I think in the case of the UK, it’s quite
straightforward. The label will give you all of the ingredi- February 15–16—Biobased World Tradeshow; Cologne,
ents of the product and then have “flavoring” or “natural Germany; www.biobasedworld.de/en/home.html
flavoring” and that really doesn’t give insight to the con- February 16—Society of Flavor Chemists Meeting;
sumers of what it is. I’ve been in the industry a long time Philadelphia, PA; www.flavorchemists.com
and people will still think that if you buy a raspberry flavor February 22–23—FlavourTalk Amsterdam; Amsterdam,
sweet, they assume the flavor has come from a raspberry. Holland; www.flavourhorizons.com
Where in most cases, it hasn’t at all and instead has come
from a multitude of sources. March 9—Chemical Sources Association, NAFFS and SFC
Joint Meeting; Anaheim, CA; www.chemicalsources.org
P&F: Do you think that the industry could do more March 17–19—Phyt’Arome; Grasse, France;
to educate consumers? Is it worth it for flavor houses www.phytarom-grasse.fr/en/
and CPGs to go down this road? May 7–9—FEMA Annual Business Meeting &
GU: Probably not. It might frighten people if they Leadership Conference; Naples, FL; www.femaflavor.org/
knew flavors are basically a bunch of chemicals. What they events
wouldn’t understand is that these chemicals are closely May 11—Chemical Sources Association Roundtable;
monitored and we couldn’t use anything that isn’t safe. But Newark, NJ; www.chemicalsources.org
the minute you use the word ‘chemical’ in front of a con-
sumer, they panic. June 14–15—SIMPPARR; Paris, France; www.simppar.fr/
As far as flavorings go, flavor is a good thing. If you have a June 25–28—IFT; Las Vegas, Nevada;
concentrated liquid flavoring (versus a seasoning), it hardly http://am-fe.ift.org/cms/?pid=1001034
has a calorific value and certainly the dosage that it goes into July 3–7—Design with Scents; London, UK; www.arts.
the food. So if you have a product—say a dairy product— ac.uk/fashion.courses/short-courses/fashion-marketing-
and you wanted to reduce the fat content that tastes as communications/perfumery-course/
good as the full fat—which is impossible—you can still get
September 24–28—IFEAT; Athens, Greece; www.ifeat.org/
somewhere close to it. You can make an improvement on it
with the addition of a flavoring, which isn’t giving you any October 12—35th Annual WFFC Gala; Woodland Park,
fat or calorific value. NJ; www.wffc.org/page-703537
A lot of the foods that are processed, the natural flavor- October 23–25—FEMA 47th Fall Symposium;
ing pretty much gets destroyed, so you have to add it back. New Brunswick, NJ; www.femaflavor.org/events
What you’re adding back is a natural flavoring or synthetic,
October 25–27—Flavorcon; Rosemont, Illinois;
whichever your customer needs, to continue and even
enhance that consistency in taste perception in a product. www.flavorcon.com/
Flavoring is not a bad thing.
2018
P&F: Right. Ultimately, we want to not only enjoy June 5–7—World Perfumery Congress; Palais des Congres
what we are consuming, but understand it as well. Nice Acropolis, Nice, France; wpc.perfumerflavorist.com
July 15–18—IFT; McCormick Place, Chicago, Illinois;
http://am-fe.ift.org/cms/?pid=1001034

19

PF1701_Industry_fcx.indd 19 12/16/16 3:10 PM


Raw Material Bulletin
Want to connect with a supplier? Contact our assistant editor at jnovoseletsky@allured.com.

Mugetanol (CAS# 63767-86-2) Natural Advantage N


is a Symrise ingredient with now offers two chocolate H3C CH3
a floral odor profile of lily of OH recipes featuring: natural
the valley elements and rosy chocolate thiazole S
aspects. Mugetanol gives body (FEMA# 3680, CAS#
and volume to rose notes and 15679-12-6) and natural O
twists fruitiness. This top note cocoal FCC (FEMA#
product implements light floral and liveliness, while offer- 3199, CAS# 21834-92- H
ing stable properties. The recommended use level is from 4). Using both chocolate
1% up to 10%. thiazole and cocoal FCC at
1.66 ppm provides a cherry
cordial-like flavor. For a
Sigma-Aldrich Flavors & Fragrances has launched creamy dark chocolate H3C
b-damascone, ≥95%, sum of isomers (FEMA# 3243,
CAS# 23726-91-2), a kosher ingredient with taste char-
flavor, chocolate thiazole CH3
should be used at 1.66 ppm
acteristics of green, wood, mint, herbal and floral. Odor and cocoal FCC should be used at 3.33 ppm.
characteristics consist of fruity, floral, berry, plump, blackcur- Both ingredients are E.U. and U.S. natural, kosher,
rant, honey, rose and tobacco. This ingredient can be used for non-GMO and vegetarian.
marjoram, marigold, blackcurrant, plum, ginger ale and more.
Additionally, the company introduced undecylenic acid,
natural, ≥97%, FG (FEMA# 3247, CAS# 112-38-9). The
taste characteristics are woody and mildly acidic and the
odor resembles sweet wood. This ingredient is best used
with woody-like applications.

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

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Untitled-2 1 12/12/16 1:52 PM
Flavor Bites

Geraniol
The rose character of geraniol is very bright and fragrant but it also
possesses considerable depth, which is especially helpful in flavors.

n BY JOHN WRIGHT, johnwrightflavorist@gmail.com

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

PF1701_Wright_irv.indd 22 12/16/16 3:12 PM


characteristically of roses in subtly Elderflower: This minor but very Tropical Fruit Flavors
different ways. All three can find interesting flavor profile can be quite Lychee: Far too many lychee flavors
interesting uses in a wide range of challenging to creative flavorists. seem to represent very little beyond the
flavors. All three could find dedicated Typically, a modest addition of this obvious rose note and lack realism and
proponents within the creative com- ingredient, around 300 ppm, can be complexity. That common failing should
munity but, although I like nerol and very helpful. still not deter a flavorist from using
citronellol, my personal preference is geraniol as the best central anchor in a
distinctly for geraniol (FEMA# 2507, Citrus Fruit Flavors lychee flavor. 2,000 ppm is ideal.
CAS# 106-24-1). Lemon: Geraniol can fill two inter- Mango: Mango flavors are a study
The rose character of geraniol is esting roles in lemon flavors. Firstly, it in contrasting notes, some bright
very bright and fragrant but it also can add realism and depth, taking away and sharp, some sweet and heavy.
possesses considerable depth, which a great deal of the harshness of citral. Geraniol can help to unify these
is especially helpful in flavors. It can Secondly, it can provide a modest notes. 1,000 ppm is a good starting
find a place in a wide range of different hedge against the loss of citral during point in mango flavors.
flavors, invariably adding authenticity end product storage through oxidation. Kiwi: Although kiwi flavors are
and complexity. Geraniol oxidizes first to geranial (one quite delicate they can still accom-
Note that the dose rates given of the two components of citral), giving modate a reasonable level of this
throughout this article are the levels a little added stability to the flavor. ingredient. Again, 1,000 ppm is a good
suggested for use in flavors intended 2,000 ppm is a good starting point in starting point.
to be dosed at 0.05% in ready-to-drink lemon flavors. Passion Fruit: More moderate levels
beverages or in a simple bouillon. Bergamot: Bergamot oil is clearly work best in passion fruit flavors, adding
more floral than lemon oil but geraniol pleasant complexity at around 500 ppm.
Floral Flavors only plays a secondary role in berga-
Rose: If rose otto represents the mot flavors. Nevertheless, it can be Berry Fruit Flavors
best rose profile unfortunately it is far very useful at levels in the region of Raspberry: Raspberry flavors
from the most economical. Most rose 1,000 ppm. always benefit from a significant level
flavors are built round a compounded Orange: Geraniol is also a second- of damanscenone. This ingredient is
base and geraniol is a key ingredient. ary character in orange flavors but also very important in the profile of
The best use levels are quite high, it fills out the profile of orange juice rose otto and in that context it forms
around 10,000 ppm in rose flavors. flavors very nicely at around 500 ppm. a superb alliance with geraniol. The
Neroli: Geraniol should not be Grapefruit: Slightly lower levels, same is equally true of raspberry
dominant in orange blossom flavors but nearer 300 ppm, perform a very flavors and geraniol enhances the
it can add very useful depth at around similar function in realistic grapefruit balance of all raspberry flavors at levels
3,000 ppm. juice flavors. up to 1,000 ppm.

23

PF1701_Wright_irv.indd 23 12/16/16 3:12 PM


Flavor Bites

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

24 Flavor Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Wright_irv.indd 24 12/16/16 3:12 PM


And you thought 2016 was nuts...
2017 has only just begun
NATURALS FROM THE NAME YOU TRUST!
At Natural Advantage, both our natural Cocoal FCC (FEMA 3199)
and our natural Chocolate Thiazole (FEMA 3680) feature
soothing nut, chocolate and cocoa flavor notes sure
to keep your taste buds satisfied all year!

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)

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p000_pf_natadv_chocolate thiazole.indd 1 12/8/16 1:20 PM


Ingredients

A Natural
and a Pod:
Shared chemistry,
biochemistry and
processing in tea leaf
and vanilla pod.

n BY PATRICK DUNPHY, Ph.D., flavor & vanilla consultant, U.K. and


KRISHNA BALA, Ph.D., president, Flavor Innovations, St. Louis, Mo., USA

Introduction considered both the common and inherent differences these


The cultivation and processing of many natural raw materials share regarding biochemistry, chemistry and pro-
materials conducted in tropical or semi-tropical climates cessing. By taking a multidisciplinary approach, it may be
employ conditions that have not materially changed over possible to utilize information from these individual tissues
the last 50 years. to mutual benefit.
Our understanding of the molecular biology and bio-
chemistry of plant tissues, especially the ripening and Tea Processing
senescence processes, have developed extensively over the Both green and black teas are manufactured from the
last 10-15 years. Newer ways of handling plant materials young leaves of Camellia sinensis L. of the genus Camellia
using milder processing have supplemented our capability to and the family Theaceae. By a spectrum of processing proto-
manipulate these systems. However, the exploitation of this cols—from mild to more robust—families of teas including
understanding and these technologies in terms of improved white through green and oolong to black are produced.
natural materials processing has not been extensively Fresh cut tea leaves contain between 75-80% moisture and
implemented. a unique family of polyphenolic catechins whose concen-
On the basis of this developing knowledge we have high- tration in the fresh tealeaf range from 13-25% of the dry
lighted two key natural raw materials—tea and vanilla—and weight. Four monomeric catechins comprise this group
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
26 Ingredients Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Dunphy_fcx.indd 26 12/16/16 3:15 PM


HONEYFLO
OR
Honeyflo or’s oddor imparts a powerful green note with
hyyacinth and hooneey undertones. Honeyflflorr exxcels at adding
and enhancing nattural honey notess in flflavo or formulations. It
also works well fo or addinng a strong flo
oral ho
oney character to
a variety of fruit and
d chocolate compositionss.
For spec sheets and other product information, visit us att
bedoukian.com or contact us by phone (203)830-4000
or email at customerservice@bedoukian.com.

Untitled-4 2 8/24/16 1:25 PM


Ingredients

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.

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F-1.
OH OH
OH OH OH OH
H H
OH OH
HO O HO O
H H
OH

(-)-epicatechin (EC) (-)-epigallocatechin (EGC)

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

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Ingredients

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

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horseradish peroxidase/hydrogen peroxide rapidly dimerises These oxidation/browning reactions in vanilla beans
to di-vanillin [6]. The pathway to the di-phenylmethanes were shown to be dependent on the presence of molecular
has not been defined though radical coupling of appropriate oxygen. Under conditions where oxygen was limited or
phenols, such as vanillin, vanillyl alcohol, guaiacol and other excluded, browning of vanilla beans does not occur even
suitable phenols catalyzed by POD/hydrogen peroxide and/ over a 10 day fermentation period at 60oC. Introduction of
or PPO/molecular oxygen, which could be the route of for- air into vanilla beans incubated in an anaerobic or anoxic
mation. Rathore and Kochi (1995) described the synthesis environment resulted, within 2-3 hours, in brown color-
of di-phenylmethanes via dealkylative coupling of benzylic ation of the green beans [8]. The browning of ripe, green,
ethers in the presence of the stable cation radical oxidizing vanilla beans under these conditions is a molecular oxygen
agent Orange CRET [7]. dependent reaction. It also appears that anoxic or anaerobic

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

Blue Boxes: Compounds already reported in cured vanilla beans

Brown Boxes: Novel compounds found only in cured vanilla beans

(Continued on Page 34)

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Untitled-1 2 12/12/16 1:49 PM
Untitled-1 3 12/12/16 1:49 PM
Ingredients

(Continued from Page 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.

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Dopaquinone cyclizes to leuco-dopachrome which is then quinones can react with nucleophiles, such as µ-amino
oxidized to give orange dopachrome. Following a series of acids or polymerize to complex polyphenols. In addition,
further reactions, dopachrome then polymerizes to melanin the o-quinones can oxidize monophenols, such as vanillin
[14]. In the context of browning in vanilla beans during the to dimeric di-phenols. The latter compounds may also be
fermentation stage, it is well established that the mono-phe- generated by reaction of the monophenol with POD/H2O2
nol vanillin is readily oxidized by POD/hydrogen peroxide, (see F-5).
an enzyme active in vanilla beans, to yield di-vanillin 6. There are clear similarities and some differences
It is likely therefore, that phenol oxidation in fermenting between vanilla and tea taste compounds in terms of:
vanilla beans proceeds to dimeric and polymeric, brown
pigments, as follows: • Precursor molecules. In both cases phenolic and poly-
phenolic respectively
• PPO/molecular oxygen oxidation of o-diphenols to the • The enzymes responsible for the oxidation of the
corresponding o-quinones which by further oxidation can phenols. In both raw materials, the enzymes POD and
realize complex colored polymeric structures, as well as PPO are the oxidation catalysts for the reactions, which
reaction of the o-quinones with nucleophiles, such as the take place principally during the fermentation phase fol-
–NH2 groups of µ-amino acids to yield colored addition lowing initial tissue damage.
products • In tea processing, PPO and POD work in sequence
• Mono-phenols such vanillin, in the presence of POD/ to produce from catechins the theaflavins followed by
hydrogen peroxide, react to produce C-C bridged dimers further oxidation of the latter to thearubigins. These
• Co-oxidation of phenols such as vanillin by the semi- compounds are responsible for the color and taste/
quinone intermediates in the oxidation of o-diphenol by mouth-feel characteristics of tea. Limitation of molecu-
PPO/O2 [15]. lar oxygen, degree of cell damage and length of the
fermentation process can influence the final mix of the
The role of molecular oxygen in this browning scheme is catechins, theaflavins and thearubigins. In the most limit-
evident. The PPO/O2 reaction is required for browning to ing cases, white or green teas are produced with minimal
occur. The primary role of this enzyme is to oxidize o-diphe- transformation of catechins. More extensive or complete
nols to the corresponding o-quinones. These reactive oxidation generates oolong and black teas, respectively,

F-5. Possible pathways of oxidation in vanilla beans during fermentation

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Ingredients

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

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Green tea

that belongs to a structural family of NADPH dependent Darjeeling Black Tea


reductases. The petunia enzyme catalyzes the reduction The key aroma compounds of Darjeeling black tea were
of coniferyl acetate to (E)-isoeugenol by a direct reductive characterized by analysis of the volatile fraction from the
elimination or via a quinone methide intermediate [19, tea infusion. Aroma extract dilution analysis of the 24 odor-
20]. A petunia acetyltransferase was shown to be most active compounds with FD factors from 4-128, highlighted
active with coniferyl alcohol as the substrate. Suppression vanillin (vanilla-like), 4-hydroxy-2,5-dimethyl-3(2H)-
of the gene encoding the acetyltransferase resulted in furanone (caramel), 2-phenylethanol (flowery) and (E, E,
the inhibition of (E)-isoeugenol biosynthesis suggesting Z)-2,4,6-nonatrienal (oat-flake-like) as the most odor potent
this enzyme was the catalyst for conversion of coniferyl compounds. Determined Odour Activity Values (OAV’s)
alcohol to the corresponding acetate; the latter being the highlighted (E ,E, Z)-nonatrienal, geraniol and linalool as key
substrate for the reductase conversion to (E)-isoeugenol odorants in the infusion [23].
[21]. (E)-isoeugenol may also arise by thermal degra- As in the green tea volatiles above, the two terpene
dation of coniferyl alcohol. Pyrolysis of a number of alcohols, geraniol and linalool, and the substituted phenol
phenylpropanoids exhibited homolytic cleavage around vanillin may arise by hydrolysis of their glycosidic precur-
C-O- and -O-H bonds. Pyrolysis of coniferyl alcohol, at sors in the intact, young, leaf. Phenylethanol is formed
600oC, yielded 4-vinylguaiacol and (E)-isoeugenol as the in tomato fruit by the decarboxylation of phenylalanine
major products with lesser amounts of vanillin, guaiacol to phenylamine. Removal of the –NH2 group generates
and coniferyl aldehyde. The formation of (E)-isoeugenol phenylacetaldehyde which on reduction by an aldehyde
was initiated by the elimination of the Cg-hydroxyl group reductase/NADPH realizes the aromatic alcohol [24].
of coniferyl alcohol followed by addition of a proton to Phenylethanol may also be present in the intact leaf as the
the resulting methylene radical. Further isomerization of glucoside. The trienoic compound (E, E, Z)-nonatrienal,
(E)-isoeugenol to the (Z)- isomer can also occur but to a first described in oat flake, is probably derived from lino-
lesser extent [22]. lenic acid by enzymatic or chemical oxidative routes [25].

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Ingredients

Transformation of amino acids by Strecker degradation to


produce Cn-1 aldehydes catalyzed by the naturally occur- T-1. Aroma active compounds from Mexican V. planifolia
ring 1.2- or 1,4-quinones in tea dhool, cut/damaged tea leaf, cured vanilla beans [from PJ Dunphy and K Bala, “The
at ambient temperatures occurs during fermentation [26]. quality of cured vanilla beans,” Perfumer & Flavorist, 36,
This same reaction is also possible at elevated temperatures 2-10, (2011) and modified from reference 31]
during the firing and drying process.
Carotenoids are precursors of aroma compounds par- Compound (ppm) Odor quality
ticularly in oolong and black tea production via two main
pathways. The enzymatic oxidation pathway is catalyzed Phenolics
by dioxygenases during fermentation which lead to oxy- Guaiacol 9.3 Chemical, sweet spicy
scission products which by further transformations realize
4-Methyl quaiacol 3.8 Sweet, woody
the final aroma compounds [27]. The most active precursor
carotenoid are b-carotene, zeaxanthin and lutein. Oxidized 4-Vinyl quaiacol 1.2 Chemical, phenolic
tea flavanols-quinones formed during fermentation can also p-Cresol 2.6 Balsamic, woody, spicy
co-oxidize carotenoids to aroma active molecules including 4-Vinyl phenol 1.8 Sweet, woody
b-ionone, b-damascenone and theaspirone 28. Vanillin 19118.0 Vanilla, sweet, honey
Acetovanillone 13.7 Vanillalike
Cured Vanilla Aroma
At least 200 aroma compounds have been identified p-Hydroxybenzaldehyde 873.0 Vanillalike, biscuit
in solvent extracts of cured Vanilla planifolia beans by a p-Hydroxybenxyl alcohol 65.1 Vanillalike, sweet
combination of gas chromatography/ mass spectrometry Methyl salicylate < 1.0 Chalk
(GC-MS) and high pressure liquid chromatography [29]. Methyl cinnamate 1.1 Sweet
If we assume that this list encompasses all the molecules
that are key for vanilla aroma, then simplification of the Aliphatic acids
list from >200 to a manageable group is feasible. This can Acetic acid 124.0 Sour, vinegar
be achieved by identification of the key compounds and Isobutyric acid 1.7 Buttery
their quantification by GC-MS in conjunction with deter-
Butyric acid < 1.0 Buttery, oily
mination of FD factors [16]. This exercise was conducted
on extracts of MV red Madagascan V. planifolia whole Isovaleric acid 3.8 Buttery, oily
cured beans. AEDA of the sample detected 15 active odor Valeric acid 1.5 Chesse
compounds with FD factors of >125. The seven most
important of these compounds included vanillin, guaiacol, C4 Alcohols & Keynotes
ethyl-(E)-cinnamate, 2- and 3-methylbutanoate, b-dama- 2, 3-Butandiol 8.0 Floral, oily
scenone and p-cresol [30]. The major flavor contribution 3-Hydroxy-2-butanone 14.6 Buttery
of all 15 compounds was confirmed by reconstitution
experiments. The compounded flavor based on these com- Aldehydes
pounds showed strong similarity to the original MV red 2-Heptenal 2.1 Green, oily
whole bean extract based on sensory evaluation of seven (E)-2-Decenal 1.8 Herblike, floral
key vanilla aroma attributes.
(E,Z)-2, 4-Decadienal 1.4 Herblike, fresh
Earlier work by Perez-Silva et al identified a total of 65
aroma compounds in solvent extracts of cured Mexican V. (E,Z)-2, 4-Decadienal 1.2 Fatty, wood
planifolia beans [31]. Of the total some 25 were considered
to be the compounds accounting for most of the aroma of
the cured beans (T-1)
Reconstitution experiments based on these 25 com- b-oxidation and/or fatty acid synthesis and from amino acids
pounds, at their measured concentrations in the cured beans by Strecker type degradation [34]. These reactions realize
were sensorially similar to a Mexican vanilla extract [32]. short chain compounds, mainly unsaturated aldehydes, that
The biochemical and/or chemical origin of most of the above contribute to the overall final flavor impact of cured vanilla
aroma compounds has not been established though it is clear beans [33, 35, 36]. It is clear that there are similarities in
that virtually all are released or generated during curing. the profiles and pathways of formation of aroma compounds
Vanillin and most of the phenols are present in the green in tea processing and vanilla curing. In the case of the vanilla
beans as the b-D-glucosides and are liberated by hydrolysis bean, the primary reaction involves release of the free
primarily during the fermentation stage of curing [33]. phenols by hydrolysis of their b-D-glucosides. Secondary
Further transformation of some of the liberated phenols reactions involving further transformation of the liberated
may occur to realize additional functionalized phenols. mono-phenols may occur under mild drying conditions
Non-phenolics may arise from polyunsaturated fatty acids by employed. In tea processing a number of the important

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aroma compounds appear to rise during firing/drying. These Comparison of the vanilla curing operation with that of
include the furanones and perhaps (E)-isoeugenol. Geraniol, tea processing shows some similarities.
linalool and phenylethanol may be present in the green tea In vanilla curing and tea processing they similarly require:
leaf as the glycosides, yielding the free alcohols on hydro-
lysis. The major difference between the two raw materials • Good quality raw material. For tea, the new, young
in terms of flavor generation may be a reflection of more leaves; whilst for vanilla, the ripe pods are utilized
extensive thermal treatment during tea processing. • A tissue wounding stage. In the case of tea leaves, the
Tea processing as indicated above can be very mild, white wounding is induced by partial dehydration and subse-
tea through green, through oolong to very extensive black quent tissue disruption by withering and leaf bruising.
tea. An outline of the processing regimes for the four tea For vanilla beans, the wounding is initiated by sub-
types alongside the vanilla curing operation is shown in F-6. jecting the beans, usually by hot water immersion, at
The principal differences between the four tea pro- 60o-65oC, for ca.3 minutes. In both instances, cellular
cesses are: integrity is compromised to variable extents with conse-
quent activation of enzymes, primarily hydrolases and
• The degree of tissue damage. This defines the potential oxido-reductases.
for extensive oxidation of the endogenous catechins. • A critical fermentation stage where free or liberated
• The length of the fermentation stage. This dictates the phenols are partially or totally oxidized by PPO/molecular
extent of oxidation of catechins to theaflavins and thea- oxygen and POD/hydrogen peroxide result in complex
rubigins resulting in green through black/brown product polymeric “brown” pigments that have mouth-feel and
appearance as well as the generation of characteristic taste characteristics. In addition, aroma compounds are
aroma compounds. In unfermented teas, green notes generated from simple phenols and amino acids as well
predominate whereas in fully fermented teas aroma notes as by degradation of carotenoids.
associated with Strecker/Maiillard reactions as well as • An enzyme inactivation stage (firing) and subsequent
carotenoid scission products appear. drying stage that finalizes the formation of the mix of
• The absence or length of the firing and drying stages. aroma compounds in the final product. This thermal
Firing and drying stages enhance Strecker/Mailard and process is important in the tea firing/drying process.
carotenoid scission reactions. During vanilla curing lower temperatures are employed

F-6. Principal stages in tea and vanilla processing

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Ingredients

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
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40 Ingredients Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Dunphy_fcx.indd 40 12/16/16 3:15 PM


4. T Tanaka, Y Betsumiya, C Mine and I Kouno, Theanaphthoquinone, a 24. D Tieman, M Taylor, N Schauer, AR Fernie, AD Hanson and HJ Klee,
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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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42-49, (2010),
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dilution analysis, Trends in Food Sci. and Technol., 4, 68-73, (1993). 36. PJ Dunphy and K Bala, Green vanilla bean quality, Perfumer & Flavorist,
36, 38-46, (2011).
17. R Baba and K Kamazawa, Characterisation of the potent odourants
contributing to the characteristic aroma of Chinese green tea infusions 37. K Anuradha, BN Shyamala and MM Naidu, Vanilla-its science of
by aroma extract dilution analysis, J. Agric. Food Chem., 62 (33), 8308- cultivation, curing, chemistry and nutraceutical properties, Crit. Rev.
8313, (2014). Food Sci. Nutr., 53 (12), 1250-1276, (2013)

18. I Blanc and LB Fay, Formation of 4-hydroxy-2,5-dimethyl-3 (2H)-furanone


and 4-hydroxy-2(or5)-ethyl-5(or 2)-methy-3(2H)-furanone through
Maillard reaction based on pentose sugars. J. Agric. Food Chem., 44 (2), To purchase a copy of this article or others,
51-536, (1996). visit www.PerfumerFlavorist.com/magazine.

19. T Koeduka, E Fridman, DR Gang, DG Vassao, BL Jackson, CM Kish, I


Orlova, SM Spassova, NG Lewis, JP Noel, TJ Baiga, N Dudareva and E
Pichersky, Eugenol and isoeugenol, characteristic aromatic constituents
of spices, are biosynthesised by reduction of coniferyl alcohol ester, PNAS,
103 (26), 10128-10133, (2006).

20. JK Muhlemann, BJ Woodworth, JA Morgan and N Dudareva, The


monolignol pathway contributes to the biosynthesis of volatile
phenylpropenes in flowers, New Physiol., 204, 61-670, (2014).]

21. R Dexter, A Qualley, CM Kish, CG Ma, T Koeduka, DA Nagegowda,


N Dudereva, E Pichersky and D Clark, Characterisation of a petunia
acetytransferase involved in the biosynthesis of the floral volatile isoeugeol,
Plant J., 49 (2), 265-275, (2007).

22. M Akazawa, Y Kojima and Y Kato, Reaction mechanisms of pyrolysis of


four different phenylpropanoids. US Open Pyrolysis Technol. J., 1 (1),
1-12, (2015).

23. C Schuh and P Schieberle, Characterisation of the key aroma compounds in


the beverage prepared from Darjeeling black tea. Quantitative differences
between tea leaves and the infusion, J. Agric. Food Chem., 54 (3), 916-
924, (2006).

41

PF1701_Dunphy_fcx.indd 41 12/16/16 3:15 PM


The Juice

Wolfgang Krause, Ph.D.


Krause’s work with geraniol, citral and menthol introduced him
to the world of flavor and fragrance where he continues to
foster an advocacy for the industry by active participation in
the community and education to the trade and public.

n BY PIA LONG, director, Olfiction Ltd., Pia@Olfiction.com, United Kingdom

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.

Most of my time at BASF has gone


into being involved with inventing a new
process for menthol, which took me 10
years from the first steps to finally making
it happen.

An Unexpected Route Wolfgang Krause, Ph.D.


“Most of my time at BASF has gone into being involved
with inventing a new process for menthol, which took me 1981 to 1989, I felt more or less caged by that wall and
and my colleagues more than 10 years from the first steps to wanted to escape Berlin and find an appropriate job in an
finally making it happen,” said Wolfgang. industry that would give me the opportunity to find some-
The team has developed a completely new synthesis route thing new.”
for menthol from citral. In September 2016, this longstanding “My professor had contacts at the Swiss company
project was awarded with the BASF Innovation Award. Hoffman LaRoche and I was invited for a job interview
Wolfgang attended the Technical University of Berlin in there with a German director of fine chemicals. It was about
the 1980s and spent his formative years feeling trapped by vitamins. After this Swiss interview, I had another appoint-
the Berlin Wall. ment in Ludwigshafen – and I remember how stressed I was
“Most of the good things in life come from trial and error about this – to interview with BASF on the same day. I had
and everything is based on a specific sequence of events, a telephone confirmation on the train back to the Frankfurt
you know,” he reminisces. “When I studied chemistry from airport, five minutes before passing Ludwigshafen that

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

PF1701_Long_fcx.indd 42 12/16/16 3:19 PM


A flower hanging on the Berlin Wall on November 2, 2013 in Berlin, Germany. It is part of the original Berlin Wall which collapsed in 1989.

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

PF1701_Long_fcx.indd 43 12/16/16 3:19 PM


The Juice

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.

44 Fragrance Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Long_fcx.indd 44 12/16/16 3:19 PM


you can get a fine product from citral, but if you start your Henkel, Symrise – Weleda; small companies, and we have
geraniol synthesis with turpentine chemistry, you inevitably about 200 members at the moment.”
get some remaining trace odor from that process. That’s the “Perfumers are very important, but you need the other
natural effect of the synthesis – it’s about trace substances functions. You need the chemists and the sales people
and purity. and the engineers to make it happen. You need marketing
Indeed, a buyer in a fragrance house might consider van- teams. Everything is interlinked. I believe in our approach –
illin from any source interchangeable, but vanillin ex lignin some people think that the German fragrance association is
versus vanillin ex eugenol will have noticeable odor and a little bit strange because it is not so exclusive to perfumers
flavor fingerprints and perfumers and flavorists will notice but I think our industry needs to be united,” says Wolfgang.
the difference in quality. He calls the new The International Society of Perfumer
“Finally, you can really destroy good qualities by not Creators (SIPC) “a great and valuable mission” – and strongly
having adequate production environments. It is very believes it will help protect customers and perfumers alike.
important to produce chemicals in a really clean, proper Members of press and the general public often turn to
way, using dedicated processes, which lead to homogenous societies like the DGP for any fragrance-related advice.
qualities. This is an advantage.” Wolfgang recalls one such story: “We were approached
about ten years ago by someone who was very excited,
Perfumery Advocate after finding a piece of ambergris on the beach weighing
Krause is the current president of the German several kilos. He told me on the phone that it must be
Association of Perfumers (Deutsche Gesellschaft der worth several million and how he was going to buy a house.
Parfümeure, DGP). He takes his perfumery advocacy He just wanted us to take a look. Unfortunately it turned
seriously by active participation in the community and out to be oil.”
getting the message out there – not just to trade, but to the
general public. There’s Always One
The German association was formed in 1979 as a profes- In his 15 year involvement at the DGP and his
sional network of not just perfumers, but also of other experts role at BASF, Wolfgang has been actively involved in
within the field. Wolfgang feels the society’s inclusiveness of
the whole team of people who make fragrance happen is what
sets them apart from other international societies.
“We try to represent perfumery in Germany and drive
the emotional aesthetic element, and to educate the general
public about perfumery,” explains Wolfgang.
“There are study trips for our members to explore raw
material sources; we’ve been to Italy and Bulgaria in 2010
and 2013, and are planning a trip to Spain in 2017 – but we
also hold external events. There is an awareness program
during the annual SEPAWA (detergents, cosmetics and
toiletries association) congress, where we always actively
participate with an afternoon program around perfumery
issues. More than 2000 people attend, and there has been
steady growth in visitor numbers over the years to the
exhibition and lectures. We cover emotional aesthetics of
perfumery, awareness of the beauty of perfumery – and
in 2016 we presented the value chain of perfumed prod-
ucts from ingredient to composition to finished product.
Finally, we have our own DGP stand where the general
public are invited to raise questions about perfumery,”
explains Wolfgang.
“Sometimes the moments of discovery can be really
simple, yet profound – like seeing a piece of sandalwood
and making the connection between that, an ingredient they
can smell and a finished product, so the stand we have there
can really bring in a lot of wow effects.”
The German Association of Perfumers has approximately
70 perfumer members, and the rest of the society’s members
perform other functions in the industry. “There are all kinds
of professionals from the industry here – perfumers from

45

PF1701_Long_fcx.indd 45 12/16/16 3:19 PM


The Juice

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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PF1701_Long_fcx.indd 46 12/16/16 3:19 PM


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Untitled-1 1 5/27/16 10:05 AM


Flavor

Organoleptic Characteristics
of Flavor Materials
n BY JUDITH MICHALSKI, Senior Flavorist, abelei flavors; jmichalski@abelei.com

Possible applications: This interesting material will fit nicely


Organoleptic Evaluation Panelists into flavors that have a green, vegetable-like note, espe-
• Gerard Mosciano, Consulting Flavorist cially cucumber, green pepper, honeydew melon, pear
• Deborah Barber, Senior Flavorist, FONA and apple.
• Cyndie Lipka, Senior Flavorist, Prinova Essential Oils of Tasmania: www.eotasmania.com
• Susie Sadural, Senior Flavorist, Sensient Flavors
Orange Carbonyls EO LV #40826
• Tom Gibson, Vice President of R&D and Applications, Source: Cvista
Silesia Flavors FEMA# 2821, CAS# 68606-94-0, natural, Citrus sinensis
• Robert Pan, Principal Development Scientist, Givaudan Osbeck
Flavors Corp. Odor: @ 100%. Sweet, orange, peely, waxy and slightly floral.
Taste: @ 2 ppm. Sweet, slightly floral, orange, citruslike
and peely.
Green Pea KiiNote1 R2641 Taste: @ 5 ppm. Heavy, citruslike, orange, peely, waxy and
slightly floral.
Possible applications: This fraction of orange oil will contrib-
ute to deep heart notes in citrus flavors, especially orange,
mandarin, tangerine, clementine and punch flavors. It
will be especially helpful in marmalade flavors.
Cvista: www.cvista.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

PF1701_Michalski_fcx.indd 48 12/16/16 3:21 PM


C E L E B R AT E

YEARS OF
ARTICLES
At your fingertips when you subscribe online
www.PerfumerFlavorist.com

PF_40Yrs_FullPg.indd 2 12/12/16 10:46 AM


Flavor

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

White Cognac Oil


Source: Charkit
FEMA# 2332, CAS# 8016-21-5, natural
Odor: @ 100%. Waxy, alcoholic, winey, fruity, whiskeylike
and soapy.
Taste: @ 2 ppm. Winey, oily, slightly fruity and soapy.
Taste: @ 5 ppm. Winey, soapy, fermented and fruity.
Possible applications: Not only will cognac and brandy fla-
vors benefit from this product, but champagne, cider, Source: Excellentia
tequila, wine, whiskey and beer will as well. It will also FEMA# 3149, 4434, 3150, CAS# 55031-15-7, 15707-34-3,
add ripe notes to fruit flavors like banana, grape, blue- 13925-07-0, natural
berry, pineapple, peach, apple and golden kiwi. Natural occurrence: All three are found together in various
Charkit: www.charkit.com roasted products like coffee, cocoa and peanut. Separately
they’re found in hazelnut, Swiss cheese, tobacco, beef,
Coffee CO2 Heavy Roasted (water soluble) #505099 potato, rum, whiskey, barley, lavender and popcorn.
Source: Vigon Odor: @ 1%. Earthy, raw nuts, dank, musty, cocoalike and
GRAS, CAS# 68916-18-7, natural, Coffea arabica baked potato skin.
Odor: @ 100%. Roasted, coffee, nutty, slightly cocoalike Taste: @ 1 ppm. Nutty, musty, brown, toasted and slightly
and ashy. chocolatelike.
Taste: @ 0.01%. Ashy, roasted, coffee, slightly smoky and Taste: @ 2 ppm. Nutty, earthy, roasted, chocolatelike and
dark chocolatelike. coffeelike.
Taste: @ 0.02%. Ashy, roasted, coffee, slightly smoky and Possible applications: All nut flavors, but especially pecan,
dark chocolatelike. hazelnut, black walnut and peanut, are great applica-
Possible applications: This particular extract will add some tions for this pyrazine mixture as well as non-sweet
serious depth to all flavors coffee like mocha, espresso, brown flavors like bread, coffee, baked potato, toasted
tiramisu, liqueur types as well as dark chocolate, dark grain and roasted meat. Of course, chocolate and cocoa
beer, roast beef and grill flavors. flavors are a given.
Vigon: www.vigon.com Excellentia: www.excellentiainternational.com

1-(Methylthio)octan-3-one 2-Methyl-3-tetrahydrofuranthiol Nat, 0.1% in EtOH


Source: DeLong Chemicals America Source: Excellentia
FEMA# 4707, CAS# 61837-77-2 FEMA# 3787, CAS# 57124-87-5, natural
Natural occurrence: Tomato Natural occurrence: Beef and pork.
Odor: @ 1%. Earthy, mushroomlike, vegetablelike, slightly Odor: @ 0.1%. Meaty, beefy, sulfurous, savory, onion/garliclike
meaty, cruciferous, tropical and metallic. and brothy.
Taste: @ 0.5 ppm. Earthy, green, vegetablelike and wasabilike Taste: @ 0.2 ppm. Meaty, savory, sulfurous, brothy and
with a burn. onionlike.
Taste: @ 1 ppm. Green, cruciferous, alliaceous, vegetablelike, Taste: @ 0.5 ppm. Cooked beeflike, savory, meaty, onionlike
mushroomlike and tropical. and brothy.
Possible applications: This savory chemical will enhance Possible applications: This almost umami-like component will
cruciferous flavors like wasabi, cauliflower, cabbage, enhance roasted meat flavors like beef, chicken, turkey,
horseradish and also onion and garlic. Its earthy notes will pork and bacon. Its brothy quality will add depth to ‘au
enhance onion, garlic, mushroom, potato and perhaps jus’, broth, gravy, soup and cooked onion/garlic flavors.
mold-ripened cheeses like gorgonzola, brie and blue. At Excellentia: www.excellentiainternational.com
very low levels it will open up the profile of fruits like
durian, guava, melon and papaya. To purchase a copy of this article or others,
DeLong Chemicals America: www.delongchemicals.com visit www.PerfumerFlavorist.com/magazine.

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Progress in Essential Oils

Spike Lavender Oil


n BY BRIAN M. LAWRENCE, Consultant

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

PF1701_Lawrence_fcx.indd 52 12/16/16 3:26 PM


T
he taxonomic origin sabinene (<0.1–1.6%) camphor (0.8–23.5%)
of spike lavender oil b-pinene (<0.1–4.1%) citronellal (<0.1–0.1%)
is Lavandula latifolia 3-octanone (<0.1–0.2%) d-terpineol (0.2–1.2%)
myrcene (<0.1–0.4%) borneol (0.4–10.1%)
Medic. A survey of
a-phellandrene (<0.1–0.1%) lavandulol (0.2–1.5%)
the published reviews
a-terpinene (<0.1–0.3%) terpinen-4-ol (0.3–2.3%)
on spike lavender oil p-cymene (<0.1–1.4%) r-cymen-8-ol (<0.1–0.4%)
(Lawrence, 1978, 1980, 1983, 1984, limonene (0.2–3.2%) a-terpineol (0.5–10.8%)
1987, 1990, 1993, 2001, 2006) revealed 1, 8-cineole (18.8–42.4%) hexyl butyrate (<0.1–0.4%)
that the constituents which were (Z)-b-ocimene (<0.1–4.2%) myrtenol (0.1–0.8%)
unequivocally characterized in this oil, (E)-b-ocimene (<0.1–1.3%) trans-carveol (<0.1–0.1%)
listed in elution order from a non-polar g-terpinene (0.1–0.6%) nerol (<0.1–0.7%)
capillary G/C column, were as follows: cis-sabinene hydrate (0.2–0.9%) cis-carveol (<0.1–0.5%)
terpinolene (0.1–0.7%) hexyl 2-methybutyrate (<0.1–0.4%)
p-cymenene (<0.1–0.2%) carvone (<0.1–0.5%)
a-thujene (<0.1–0.2%) linalool (11.0–53.8%) geraniol (<0.1–1.8%)
a-pinene (1.1–6.8%) a-thujone (<0.1–0.1%) linalyl acetate (<0.1–3.4%)
camphene (0.1–2.1%) cis-linalool oxidef (<0.1–6.9%) bornyl acetate (<0.1–0.7%)
1-octen-3-ol (<0.1–0.1%) trans-linalool oxidef (<0.1–6.4%) cuminyl alcohol (0.1–0. 2%)

53

PF1701_Lawrence_fcx.indd 53 12/16/16 3:26 PM


Progress in Essential Oils

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

54 Ingredients Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Lawrence_fcx.indd 54 12/16/16 3:26 PM


carvacrola (0.2%)
T-2. Comparative percentage composition of the volatiles of Lavandula latifolia terpinen-4-yl acetate (0.2%)
produced by different processes geranyl acetate (0.7%)
a-cubebene (0.1%)
Compound 1 2 3 dihydroeugenol† (0.1%)
a-ylangene (0.1%)
a-thujene 0.6 0.2 – a-copaene (0.7%)
camphene 0.2 0.2 – b-bourbonene (<0.1%)
b-elemene (2.1%)
sabinene 0.3 0.2 0.6
longifolene† (0.3%)
b-pinene 0.9 0.4 t b-cubebene (0.7%)
myrcene 1.0 0.5 t aromadendrene (0.3%)
d-3-carene 0.1 t t b-bisabolene (0.3%)

p-cymene 0.6 0.3 t † incorrect identification


aidentity requires corroboration
b-phellandrene 0.3 t t
1,8-cineole 22.8 14.6 11.8
Munoz – Bertomeu et al. (2007)
(Z)-b-ocimene t 1.2 t examined the composition of the
(E)-b-ocimene 0.6 0.4 t hydrodistilled oils of spike lavender
trans-sabinene hydratea 0.8 1.1 0.2 leaves and flowers that were collected
linalool 29.6 29.2 18.3 from plants harvested in full flower
camphor 6.9 6.4 8.1 from seven different location in Spain.
The results of the analyses that were
borneol 14.2 16.1 19.0
performed using GC/MS only can be
terpinen-4-ol 0.9 1.4 1.6 seen in T-1
a-terpineol 2.6 2.8 10.5 Eikani et al. (2008) compared the
isobornyl formate† 0.3 0.3 1.8 volatile composition of a hydrodistilled
cuminaldehyde 1.0 1.2 1.9 oil with those of a solvent extract and
linalyl acetate 1.8 2.8 6.4 an extract produced by superheated
water of L. latifolia, which was har-
lavandulyl acetate 0.6 0.3 1.0
vested from plants in full flower from
9-epi-b-caryophyllene† 0.2 0.3 3.8 an experimental field in Kashan (Iran).
(E, E)-a-farnesene t 0.2 t The volatiles, which were analyzed by
T-cadinol 0.9 1.1 t a combination of GC/FID and GC/MS
a-bisabolol 2.7 3.1 t can be seen in T-2.
Williams (2008) reported that a
b-caryophyllene 0.1-0.2 0.5-1.1
commercial sample of spike lavender oil
caryophyllene oxide 0.2-0.7 0.2-0.7 contained the following constituents:
1=hydrodistillation, 2=Soxhlet extraction 3= superheated water extraction
t = trace (<0.1%) a = should be cis-isomer a-pinene (1.9%)
†incorrect identification
camphene (0.7%)

55

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Progress in Essential Oils

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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Progress in Essential Oils

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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Endpoint.

Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2017 Allured Business Media.
62 Endpoint Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1701_Endpoint_fcx.indd 62 12/16/16 3:29 PM


n BY RACHEL GRABENHOFER, managing editor, Cosmetics & Toiletries

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.

The Sound of the Senses


A great example is an award-winning paper presented
at the 2016 International Federation of the Societies of
Cosmetics Chemists (IFSCC) Congress, on “Sonification:
Translating Product Performance into Sound.” Here, Damien
Velleman of Nihon L’Oréal showed how the tactile experience
of hair could be translated to sound. For instance, smooth,
soft hair matched the gentle glide of a harp.
Cosmetic industry expert John Jiménez, of Belcorp, has
spent his career in the neuromarketing area and thinks
synesthesia has potential to be the next big movement for
personal care. “I am sure we will see new product launches
around this concept very soon,” he said.
The concept of crossing sensory boundaries is perhaps
most prominent in the flavor and fragrance industry, espe-
cially considering how the very organs for these sensations
are biologically connected. But Oxford researchers have
expanded this duet to a trio, as The Daily Mail recently
reported.[1]
“Listening to different musical notes while eating choco-
late can change how the sweet treat tastes,” it stated. “Food
scientists have found they can alter the sensation of creami-
ness in a piece of chocolate by playing different sounds to
people as they eat.”
The article explained that a series of soft notes could
make a piece of dark chocolate taste creamier. Short, sharp
notes plucked on a violin, on the other hand, could make
the same chocolate taste sharper or bitter. The research was
published online in advance of the January 2017 edition of
Appetite.[2]

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

PF1701_Endpoint_fcx.indd 63 12/16/16 3:29 PM


Endpoint.

influences taste but also the subtler qualities of food.[3]


“It is totally about textures. It is not in the scope of taste
“Creaminess is much more related
anymore, it is in the scope of flavors, which are much more to consonant harmonics, legato
complex.” This should come as no surprise to flavorists.
“Creaminess is much more related to consonant harmon-
and reverberation. Roughness is an
ics, legato and reverberation. Roughness is an opposite opposite auditory universe.”
auditory universe,” he added. The authors are develop-
ing real-world uses for their findings, including working The authors concluded these results provide support for
with Belgian chocolatiers to market boxes with special the claim that the cross-modal correspondence between a
soundtracks. higher level musical attribute, i.e., harmony, and basic taste
In related cross-modal research, Wang and Spence can be used to modify the evaluation of the taste of a drink.
published[4] an article on the effects of various soundtracks It’s interesting how all this advanced research comes back
and the taste perception of mixed fruit juices. Participants to primal instincts and reactions. No doubt there’s something
evaluated samples of mixed fruit juice while listening to beyond the basic senses when you combine them. That puts
music harmonized with consonant or dissonant tones. Each the F&F market at an advantage, considering the very nature
sample of juice was rated on three scales: one ranging from of olfaction and taste. Use these powers wisely, and for good.
sour to sweet, while others involved hedonic ratings of the
References
music and juice.
According to the study abstract, the results of an inter- All websites accessed on Nov. 30, 2016.
net-based pre-test found participants reliably associated the 1. dailymail.co.uk/sciencetech/article-3956566/Can-music-change-taste-
consonant soundtracks with sweetness and the dissonant chocolate-test-different-sounds-trick-tastebuds.html
soundtracks with sourness. On-site, participants rated the 2. sciencedirect.com/science/article/pii/S0195666316306134
juices as significantly sweeter in the consonant than in the 3. rt.com/news/367685-chocolate-music-creamy-taste/
dissonant music condition—regardless of the melody or 4. http://booksandjournals.brillonline.com/content/
journals/10.1163/22134808-00002505
instrumentation.

64 Endpoint Vol. 42 • January 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

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Untitled-1 1 12/12/16 1:35 PM
Developing Better Products
through Natural Chemistry
Penta Manufacturing Company is Family Owned and Operated for Over 40 Years.
Here is a partial listing of our Family of Vitamin ingredients utilized in flavor and nutritional formula tions.
For detailed paperwork on all of our items consult our web site at www.pentamfg.com

■■VITAMIN A ALCOHOL ■■VITAMIN C STEARATE


■■VITAMIN A ACETATE ( L-ASCORBYL-6-STEARATE)

■■VITAMIN A PALMITATE ■■VITAMIN D2 (CALCIFEROL)


■■VITAMIN B1 (THIMINE MONONITRATE) ■■VITAMIN D3 (COLECALCIFEROL)
■■VITAMIN B2 (RIBOFLAVIN) ■■VITAMIN E (ALPHA-TOCOPHEROL)
■■VITAMIN B3 (NIACINAMIDE) ■■VITAMIN E ACETATE
■■VITAMIN B4 (ADENINE) ■■VITAMIN H (D-BIOTIN)
■■VITAMIN B5 (D-CALCIUM ■■VITAMIN K1 (PHYTONADIONE)
PANTOTHENATE) ■■VITAMIN K3 (MENADIONE)
■■VITAMIN B6 (PYRIDOXINE HCL) ■■VITAMIN P (RUTIN)
■■VITAMIN B7 ■■VITAMIN U
■■VITAMIN B8 (ADENOSINE PHOSPHATE)
■■VITAMIN B9 (FOLIC ACID)
■■VITAMIN B12 (CYANOCOBALAMIN)
■■VITAMIN B13 (OROTIC ACID)
■■VITAMIN B17 (D-AMYGDALIN)
■■VITAMIN C (ASCORBIC ACID)
■■VITAMIN C PALMITATE
(ASCORBYL PALMITATE)

For a complete list of all our natural, natural identical and synthetic ingredients
visit us at our www.pentamfg.com

Penta Manufacturing Company


A Division of Penta International Corporation

50 Okner Parkway, Livingston, New Jersey 07039-1604 Phone: (973) 740-2300 Fax: (973) 740-1839
E-Mail: sales@pentamfg.com Web: www.pentamfg.com

PF1701_penta_babycooking.indd 1 12/16/16 3:43 PM

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