Perfumerflavorist201702 DL

February 2017 | Vol. 42 no.
2
www.PerfumerFlavorist.com
Sensory
Satisfaction:
Is Liking Enough?
+ Defining natural in
flavor materials
+ Alexander Mohr, EFFA
+ g-Nonalactone
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CONTENTS VOL. 42, NO. 2 | FEBRUARY 2017
FLAVOR
6 Editor’s Note: Natural Matters
18 IfFlavor Bites: g-Nonalactone
it is not found in coconuts, g-nonalactone is actually found
in an unusually wide variety of other natural foods and offers a
bright, aggressive and unique note to flavors.
By John Wright
22 Defining Natural
How can the flavor industry overcome the challenges,
legislations and regulations of configuring the naturalness of
flavor substances?
By Fanny Lambert & Christine Schippa
42 Organoleptic Characteristics of Flavor Materials

This month’s column features organoleptic discussions on
36
cucumber pure extract, carrot heart oil, ethyl-2-methyl-3-
pentanoate, methionyl butyrate natural and more.
By Judith Michalski
FRAGRANCE
18 36 When
Sense and the Subconscious
it comes to product design, a simple “like” is not enough.
How does consumer emotion play a role in developing engaging
and successful products on the shelves?
By Daniel Blatt & Michelle Niedziela
60 Endpoint: Thinking Outside the Perfume Bottle

How might texture and feel push new F&F limits? How might
texture pair with color, flavor, scent and collective experiences?
All gimmicks aside, we’re now entering that familiar concept of
cross-modal perception.
By Rachel Grabenhofer
INGREDIENTS
16 Raw Material Bulletin
46 This
Progress in Essential Oils
month’s issue features the chemical compositions of celery
leaf and seed oil.
By Brian M. Lawrence
22
2 Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
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EDITORIAL
Jo-El M. Grossman, Director
Jeb Gleason-Allured, Editor in Chief • 1-630-344-6069/[email protected]
Deniz Ataman, Managing Editor • 1-630-344-6070/[email protected]
Rachel L. Grabenhofer, Managing Editor • 1-630-344-6072/[email protected]
Nicole Urbanowicz, Research Analyst • 1-630-344-6053/[email protected]
Jennifer Novoseletsky, Assistant Editor • 1-630-344-6045/[email protected]
Savannah Saunders, Assistant Editor • [email protected]
Brooke Schleehauf, Assistant Editor • 1-630-344-6032/[email protected]
Lisa Schryver, Assistant Editor • 1-630-344-6068/[email protected]
Ryan Daily, Digital/Social Media Editor • 1-630-344-6058/[email protected]
ADVERTISING SALES
Paige Crist, Associate Publisher/ Flavorcon & World Perfumery Congress Exhibits &
Sponsorship • 1-630-344-6060/[email protected]
Kasia Smialkowski, Coordinator • 1-630-344-6025/[email protected]
60 AUDIENCE DEVELOPMENT
Linda Schmitt, Director
Marie Galvan, Marketing Specialist
Alyssa Howard, Marketing Assistant
Customer Service • 1-866-366-9220/[email protected]
46 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/[email protected]
Andrea Blood, Exhibits Coordinator • 1-630-334-6038/[email protected]
Mark Rosenblum, Event Specialist • 1-630-334-6071/[email protected]
CORPORATE
Janet Ludwig, Partner & President
George Fox, Partner & CEO
Linda Getner, Controller
Rose Southard, Digital Products Director
Maria Romero, Executive Assistant
INDUSTRY
8 Industry: News, Events and Analysis
10 Alexander
Q&A: EU’s Regulation Progression
Mohr, Ph.D., executive director at European
SUBSCRIPTIONS
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4 Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
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Editor’s Note
Natural Matters
D
efining natural has been an evolving
topic both in our industry and the
world at large. According to an
article from researchers at the University
of California at Berkeleya, the definition of
science given in 2005 by the Kansas State Board
of Education was a polarizing debate in schools, in
terms of what it meant to study the natural world.
DENIZ ATAMAN Back then, science was defined by the board as “the
Managing Editor human activity of seeking natural explanation for
[email protected] what we observe in the world around us.” In 2007,
the definition—which is nearly identical to
the Oxfordb dictionary definition—
shifted to “a systematic method
P&F Magazine of continuing investigation that
Editorial Advisory Board uses observation, hypothesis
testing, measurement, experi-
mentation, logical argument and
DOLF DEROVIRA
theory-building to lead to more adequate explanations of natural phenomena.”
President and CEO,
Flavor Dynamics, Inc. Clearly, the definition has evolved into a more refined one.
An Evolving Definition
PATRICK DUNPHY This got me to thinking about the current challenge in F&F to define
Ph.D, Independent vanilla and flavor
natural. Now more than ever, consumers are looking at labels with an eagle
consultantt
eye for natural ingredients. The U.S. Food and Drug Administration (FDA)
is still sifting through hundreds of public comments to reach a decision
MATTHIAS GUENTERT on what to call natural. In Europe, regulations by the European Flavor
Independent flavor consultant Association (EFFA) are investing in communication strategies with a wider
public audience regarding flavors via the internet, the flavor process and the
BRIAN M. LAWRENCE professionals involved in flavor development (page 10); and natural ingredi-
Natural Products Editor, ents are a major influence behind the discussion.
Perfumer & Flavorist magazine; There’s a lot at stake to coming up with the magic definition. Another
Editor-in-Chief,
article from Berkeleyc refers to natural as any element of the physical
Journal of Essential Oil Research
universe; including energy, matter, the forces that act on matter, biological
constituents, humans, human society and the products of society. That’s a lot
JUDITH MICHALSKI of common ground to cover, no?
Senior flavorist, abelei flavors
In research, quality control continues to push boundaries to understand
the naturalness of a material (page 22). It appears that multiple levels of
LESLIE SMITH testing scan a broader spectrum to help identify the relevant components
President, Leslie C. Smith Consulting and determine a material’s naturalness.
Perhaps, then, the definition of natural may never be finite. Maybe, just
JOSH VERNOSKI like humans, science, technology and the world at large, the definition will
Regulatory affairs manager, continue to evolve.
FONA International, Inc. I hope you enjoy this issue. Happy learning to you.
With warmth from New York City,
JOHN WRIGHT
Independent flavorist and author
Deniz Ataman
Managing Editor
a http://undsci.berkeley.edu/article/natural_matters
b https://en.oxforddictionaries.com/definition/science
c http://undsci.berkeley.edu/article/natural
6 Editor’s Note Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
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Industry
Summer Johnson to Lead IFRANA’s Communications

With 17 years of leading branding and communication operations,
Summer Johnson will be overtaking the International Fragrance
Association North America’s (IFRANA) direct communications.
Johnson will be impacting the fragrance industry by educating the
public on policies. Her previous experience includes leading
campaigns and serving as a spokesperson for elected officials.
Johnson will be advising clients through three public rela-
tions firms. She has successfully created messaging campaigns for
the development and promotion of brands directly to consumer
audiences.
“Fragrance has the power, beyond all frontiers and cultures, to
enhance lives including yours, mine, and millions of farmers in the
U.S. and the developing world. It’s time to tell this story and we are
thrilled to have Summer on-board to help us in this important effort,”
said Farah Ahmed, president & CEO, IFRANA.
Hershey Hands Michele Buck a Sweet Presidential Treat

internal and external candidate interviews during the
hiring process.
Hershey Losing Ground to Start-ups?

Over the past couple of quarters, Hershey’s
and other large food and beverage manufacturers
have faced challenges with its start-up competitors.
Consumer preferences are heading towards local
companies, which in turn are affecting sales. The
company’s $7.42 billion dropped to $7.39 billion in
2015, but is expected to increase around 1% by the
end of this year to slowly begin growth once again.
Michele Buck Mondelez found that Hershey was a possible
target, but the deal died earlier in the year when the
On March 1, Michele Buck will take over
companies failed to reach an agreement. The $23
Hershey as the new president and CEO. As smaller,
billion takeover was halted by the Milton Hershey
start-up businesses begin to emerge as rivals for the
Trust, controlling 80% of shareholder votes. As
company, Buck will uses her 11 years of experience
president, Buck will press forward so that Hershey
to try and keep ahead of its competitors. She will
can remain as a stand-alone company.
succeed John Bilbrey, who is scheduled to retire
as a candy maker in 2017. Both Buck and Bilbrey
are making compensation arrangements as Bilbrey
The Rise of Female Leaders in F&F
plans to continue as a non-executive chairman of Buck is also a notable president for Hershey, as
the board. the 27th woman to run a Fortune 500 company once
Buck plans to use successful strategies through she takes the position. Her presidency adds another
the acquisition of Krave beef jerky and healthy woman to the growing list of female executives that
chocolate brand barkThins. Her participation in lead large food companies. Women like Indra Nooyi
the company’s growing confectionery portfolio will from PepsiCo, Denise Morrison from Cambell
aid her in the upcoming opportunities in the candy Soup and Irene Rosenfeld from Mondelez will soon
market. Her possibilities for success appealed add another executive to Fortune’s Most Powerful
to Hershey as the company moved forward with Women list.
Reproduction in English or any other language of all or part of this article is strictly prohibited. © 2016 Allured Business Media.
8 Industry Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
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Industry
Firmenich Nominates Master Howard Smith, Jr. Appointed

Perfumers as IOFI President
Nathalie Lorson and Tony Reichert are the most

recent to join the ranks of Firmenich’s circle of 12
master perfumers. The company nominated both
perfumers at a ceremony in Geneva, Switzerland,
which showcased their achievements and careers.
Lorson has spent her entire career in perfumery
and fine fragrance. She joined Firmenich in 2000
and has earned awards for her work for LVMH, The International Organization of the
L’Oreal, Clarins, Coty, InterParfums, P&G and Bath Flavor Industry (IOFI) named Howard
and Body Works. She recently received the 2015 Smith, Jr., a fourth generation flavor industry
Fifi award for “Best Prestige Fragrance” in France, executive, as president of the trade organiza-
Germany and the UK for her fragrance Black tion. The appointment was announced at
Opium. IOFI’s 2016 general assembly in Vienna.
Reichert has been with Firmenich for 21 years In his new position, Smith will be respon-
as a body and home care perfumer. He is passion- sible for a 10-person board in strategy
ate about helping the company’s next generation of development where he will work closely with
young perfumers to thrive. With many major market Sven Ballschmiede, executive director.
successes, he is a category leader in laundry soften- Previously, Smith served as the president
ers and air care and has created multiple air and of Virginia Dare Extract Company and a
fabric care bestsellers. representative of the Flavor and Extract
Manufacturers Association (FEMA) on the
IOFI board. Smith has been involved with
Establishing a Fragrant Legacy
the IOFI’s initiative for more than 10 years
The title of master perfumer is given to one who where he served as the treasurer and vice
has created olfactive signatures that are consid- president.
ered benchmarks for success and creativity in the “IOFI continues to invest in the scientific
industry. They have been responsible for helping to studies required to assess the safety of flavor-
nurture the company’s legacy and values since 1969, ings. We support innovative approaches that
when Firmenich created the title. are on the cutting edge of scientific research
“On behalf of Firmenich, I extend my deepest in this area,” said Smith. “In the regulatory
congratulations to Nathalie and Tony who inspire us arena, we actively support emerging markets
every day with their passion, creativity and endless where standards are being developed – this
commitment to creative excellence. Throughout is a way to share best practices while foster-
their illustrious careers, they have pioneered some ing the harmonization of flavor regulations to
of the world’s most loved fragrances which have promote global trade.”
become timeless references for consumers world-
wide,” said Gilbert Ghostine, Firmenich CEO.

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Industry
Q&A: EU’s Regulation Progression

Alexander Mohr, Ph.D., executive director at
European Flavor Association (EFFA), shared his
views with Perfumer & Flavorist on improving
communication with companies and the public
amidst regulatory changes and evolving consumer
preferences.
Perfumer & Flavorist: What are some areas of

concern for the 2017 EFFA agenda?
Alexander Mohr: More than concerns, I see

opportunities in many areas. For example, it is
crucial for us here in Europe that the different
countries have the same understanding of European
Union (EU) legislation. This is something we, as
EFFA, have been working on over the past years.
A big step in that direction was by publishing our
guidance document on the European Commission’s
Regulation on Flavorings, which was printed and
distributed this yeara and our constant update of it.
In close collaboration with our membership (compa-
nies and national associations) we will keep working
on this aspect.
Regarding the EU institutions, we have done a
great job in 2016 increasing our visibility with differ-
ent EU stakeholders, and I think it is very important
to keep working in this direction, to be a reliable
partner for the European institutions and to make
sure they understand the complexity and added Alexander Mohr, Ph.D.
value of our industry.
Of course, another key topic is communica-
infographics with data about the industry and much
tion; not only for the association, but [also] for
more. By February we will know if we have won the
the industry in general. I think there is a common
award, we will keep you posted.
understanding that it is important to tell the flavor
story to the world in a proactive way because it is
P&F: In your opinion, how do you see sustain-
indeed a fascinating one. This is why cooperation
ability affecting regulation in the EU? Are there
and partnership is crucial and also the reason we are
areas of improvement?
working closely with other regional associations such
as the Flavor & Extract Manufacturing Association
AM: Sustainability is a key issue for consumers
(FEMA) in the U.S. and the Japanese Flavor
worldwide, but it is also a multifaceted topic, which
and Fragrance Manufacturing Association, in the
includes environmental, economic and societal
context of working groups of the global association,
components. I think there are always areas of
IOFI, the International Organization of the Flavor
improvement as sustainability touches upon many
Industry.
aspects of the EU legislation: food waste, circu-
For EFFA, one of our main achievements on
lar economy, sustainable growth, etc. The flavor
communication was our new website,b [which] has
industry certainly has a role to play on all of these
been nominated as a finalist in the best website cat-
fronts and solutions to provide. Most of our flavor
egory of the European Association Awards. In 2017
houses are already involved in developing sustain-
we will continue to improve and feed the website
ability initiatives for transports, recycling, etc. Since
with videos of the many different flavor professions,
sustainability is a major global challenge, EFFA is
a http://www.effa.eu/library/guidance-documents working closely with our international partners to
b http://www.effa.eu encourage a sustainable future.

EFFA’s new website provides users with the latest updates on EU legislation, as well as a consumer-facing section that explains
the flavor development process.
P&F: The Brexit decision earlier this year

certainly made an impact on the global industry; do Sustainability is a key issue
you see any major changes that will affect regulatory
decisions? for consumers worldwide,
AM: The actual process for leaving the EU has
but it is also a multifaceted
not yet been initiated so the road might be long. topic which includes
There are many ongoing discussions and EFFA is
following them closely since one of our members is environmental, economic
the UK Flavor Association. I would like to highlight
that EFFA has European members who are not part
and societal components.
of the EU, such as Switzerland and Turkey, therefore
nothing will change for the organization from that
point of view and the UK will continue to be a valu-
able member of our association. We will of course be Consumers are also looking for diversity. Flavor
following the regulatory decisions closely and inform preferences vary according to each country since
our members and global partners accordingly. taste is a highly cultural aspect. Business opportuni-
ties in France might not be the same in Denmark,
P&F: What are key growth opportunities for the for example. This provides opportunities for the
EU’s flavor industry? industry to adapt to each consumer’s expectations.
AM: ‘Food’ in general, is a trending topic and P&F: “Safety” is a buzzword that is growing to be
consumers who are increasingly ‘conscious’ of their synonymous with “natural.” How will safety influ-
diet can find, thanks to flavorings, suitable alterna- ence flavor production?
tives, while maintaining great taste. I think this is
going to be a key opportunity for the flavor industry: AM: I think safety is rather related to the safety
reaching the consumer’s expectations of “improved assessment. In Europe there is the European Food
food,” while keeping them palatable and enjoyable. Safety Agency, in the U.S. you have the FEMA
13
PF1702_Industry_fcx.indd 13 1/13/17 2:39 PM

Industry
Generally Recognized as Safe program. Safety has ‘open the doors’ to our member companies, showing
always been a priority for our industry and it is the different steps involved and the passion of the
not linked to the fact that flavorings are natural or people working on flavors. We really want to connect
synthetic, but rather to a responsible production and with a larger public and show them the excellence of
careful quality control. the science and masterful work behind our products.
P&F: How are consumers shaping innovation in P&F: The U.S. Department of Agriculture
Europe? is currently in the process of defining “natural.”
Is it possible to reach a global agreement on the
AM: Consumers are indeed at the heart of the definition?
innovation. Marketing teams constantly analyze
consumer expectations of food and drink dynam- AM: In the EU, the definition of natural is speci-
ics to identify the taste of today… and of course of fied in the EC Regulation on Flavoringsc and at the
tomorrow. Our industry is a highly innovative one. EFFA, we also have a guidance document for the pro-
Around 10% of the turnover is invested in research, duction of natural flavoring substances and (natural)
flavoring preparations in the EU. I feel this is a good
first step; it is important to know what exactly it means
in each region so we can then work together and see
if it is possible to agree on the essentials.
Safety has always been a
priority for our industry and c http://www.effa.eu/eu-legislation/flavouring-regulation
it is not linked to the fact

that flavorings are natural
or synthetic but rather to a Events
responsible production and More events are posted at www.PerfumerFlavorist.
careful quality control. com/events. Filter events by topic and region;
submit event announcements; access exclusive
event coverage and photo albums.
development and innovation—this can start from March 9—CSA, NAFFS and SFC Joint Meeting;
new raw materials to new combinations of ingredi- Anaheim, CA; www.chemicalsources.org
ents, or new applications. This is really what makes March 17–19—Phyt’Arome; Grasse, France;
this industry full of opportunities. Our compa- www.phytarom-grasse.fr/en/
nies use different tools such as sensory panels to June 14–15—SIMPPARR; Paris, France;
determine market trends and flavor preferences www.simppar.fr/
and then they work together with expert flavorists
June 25–28—IFT; Las Vegas, Nevada;
to propose innovations adapted to the consumer’s
http://am-fe.ift.org/cms/?pid=1001034
expectations.
September 24–28—IFEAT; Athens, Greece;
P&F: How can the industry better connect with www.ifeat.org/
customers and the general public on the safety and October 25–27—Flavorcon; Rosemont, Illinois;
quality of flavors? www.flavorcon.com/
AM: The safety and quality of the products have

always been a priority for the industry, but maybe
2018
we considered it as a given and we have not com- June 5–7—World Perfumery Congress; Palais des
municated enough with a larger public. I think it is Congres Nice Acropolis, Nice, France;
important to show them the great and responsible wpc.perfumerflavorist.com
work we are doing, to let them understand the July 15–18—IFT; McCormick Place, Chicago,
lifecycle of flavor production and the excellent profes- Illinois; http://am-fe.ift.org/cms/?pid=1001034
sional know-how of the flavor houses. This is why we
are going to focus on a series of videos now that will

Untitled-1 1 1/9/17 2:05 PM
Raw Material Bulletin
Want to connect with a supplier? Contact our assistant editor at [email protected].
E.U. and U.S. natural, 2-methyl-4-propyl-1,3-ox- Bedoukian Research announces tropical dienoate
athiane (FEMA# 3578, CAS# 63767-86-2) is a (FEMA#s 3682 and 3344, CAS#s 72276-09-6 and
Natural Advantage ingredient CH3 34495-71-1), a reaction blend for use in both fra-
containing flavor characteristics grances and flavors. This ingredient is kosher, halal
of purple passion fruit with sweet, and occurs naturally in passion fruit. Its aroma
juicy and fruity notes. Used at 0.1 S
ppm, this kosher, vegetarian and
O
non-GMO ingredient is useful for
passion fruit and other complex CH3
tropical flavors.
The company also offers E.U. and U.S. natural,
2-octen-4-one (FEMA #3603, CAS # 4643-27-0),
which is kosher,
vegetarian and CH3
non-GMO H3C
certified. This O
ingredient occurs
naturally in roasted hazelnuts and features a ripe,
canned peach note. It is used to create ripe or overripe presents a powerful, sweet and juicy ethereal note,
strawberry, cherry, peach and apricot flavors at use which can be useful in an assortment of formulations.
levels of 2-5 ppm. In addition to tropical accords, it excels in a variety of
floral and citrus fragrance applications, imparting the
Sigma-Aldrich Flavors & Fragrances has intro- warmth of tropical fruits to the top and middle notes
duced d-Undecalactone, mixture of isomers, in particular. In flavors, tropical dienoate captures
natural, 98%, FG (FEMA# 3294, CAS# 710-4-3), naturalistic, fresh, ripe pineapple notes and works in
which has taste characteristics of creamy dairy, waxy a variety of tropical flavors.
lactonic, creamy with fruity peach, apricot and tropi-
cal richness with buttery, nutty nuances reminiscent *Kancor has launched OxiKan CLS (FEMA# 2992,
of pecan and macadamia at 1-5 ppm. At 1% EtOH, CAS# 84604-14-8), which is a completely refined, fully
the odor characteristics include sweet lactonic, fruity deodorized and decolorized
peach and apricot with waxy, creamy dairy depth notes. rosemary extract with highly
The potential applications include fruit flavors such functional antioxidant mol-
as apricot, peach and tropical fruits like mango and ecules. Rosemary extracts
papaya. Additionally, the ingredient can be potentially when used as an antioxidant
applied to dairy flavors such as fresh and cooked imparts flavor, aroma and
butter, ghee, buttermilk, ice cream, fluid milk, con- color to the end application.
densed milk, coffee creamers and nut flavors such as OxiKan CLS does not impart
macadamia and pecan. any flavor, aroma or color
The company also launched 2-Isopropyl-3- to the end application and
methoxypyrazine, 99%, FG (FEMA# 3358, CAS# has water and oil solubility.
25773-40-4) with taste and odor characteristics It is used in beverages and
consisting of pea, earthy and beany. This ingredient’s helps retain the flavor for an
application uses include beans, green pepper, tomato extended period of time.
and potato.
Excellentia International now offers pure and
ACS International has introduced e declactone natural anise oil Spanish (Pimpinella anisum)
(FEMA# 3613, CAS# 5579-78- 2). The ingredient has (FEMA# 2094, CAS# 8007-70-3). The ingredient’s
a spicy, vegetal and celery like odor with some typical taste and odor characteristics include spicy, warm,
lactonic creamy, milky and licorice-like and herbaceous.
fruity character. On taste, The company also introduced rosemary oil
it has a waxy, coconut, Spanish organic (FEMA# 2992, CAS# 8000-25-7).
dairy and creamy note H3C O The natural ingredient is certified organic and has
O
and will find good use in herbal, woody and camphoraceous odor and taste
sweet brown as well as savory flavors. It adds depth characteristics.
to chocolate and vanilla applications and could be an
ideal replacement for lovage or fenugreek. *OxiKan CLS is a registered trademark of Kancor.
16 Ingredients Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
PF1702_RMB_fcx.indd 16 1/13/17 11:47 AM

YOU’LL LOVE OUR NEW
NATURAL CHIRAL
MUSHROOM ALCOHOL
Introducing our new Natural (R)-1-Octen-3-ol, FEMA 2805. At 1.66ppm,
it gives a salty, white button mushroom taste with a satisfying mouthfeel.
If you prefer buttery, creamy or smooth mushroom, try 3.33ppm.
We also carry Natural

1-Octen-3-one,
FEMA 3515. At 1.66ppm,
it emits a fresh mushroom
aroma with an earthy taste.
At 3.33ppm, the taste is
like biting into a freshly
picked mushroom.
Combine both at 1.66ppm

for a fresh, earthy mushroom,
pleasing mouthfeel and a creamy
saltiness on the backend with savory notes.
For sample requests: [email protected]
TECHNOLOGY IMPROVING TASTE!

1050 Cypress Creek Rd 318-215-1456 3135 Drane Field Road
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p000_pf_natadv_mushroom.indd 1 1/10/17 2:00 PM

Flavor Bites
g-Nonalactone
If it is not found in coconuts, g-nonalactone is actually found
in an unusually wide variety of other natural foods and offers
a bright, aggressive and unique note to flavors.
n BY JOHN WRIGHT, [email protected]
A
n old boss once a little like old shoes. In the dim Some determined soul may
advised me, “Don’t and distant past g-nonalactone well eventually find “Aldehyde
throw away your (FEMA #2781, CAS #104-61-0), C18” to be present in coconuts in
old shoes before frequently, but oddly, misnamed nature, but that, in my opinion, is
you’re certain as “Aldehyde C18”, was the main stretching things. The key coconut
your new shoes driver behind all coconut flavors. recognition chemical is d-octa-
fit.” Good advice, but advice we Aldehyde C18 was an excellent lactone, the subject of a previous
all probably find hard to put into example of chemically driven article. g-Nonalactone is relatively
practice. Flavor chemicals can be research. bright and harsh compared to
d-octalactone and, in my coconut
flavors at least, it has been well
and truly thrown out with the rest
of the old shoes. g-Octalactone
has the additional advantage of
blending far more harmoniously
with the creamy higher delta
lactone that are also present in
coconuts.
This does not mean g-nonalac-
tone should be totally discarded. It
is a useful chemical and can be very
helpful in other categories. If it is
not found in coconuts it is actually
found in an unusually wide variety
of other natural foods. The rather
bright and aggressive note can
find good use in a number of other
flavors where its unique characteris-
tics can be turned to advantage.
Note that the dose rates given
throughout this article are the
levels suggested for use in flavors
that are intended to be dosed at
0.05% in a ready-to-drink bever-
ages or in a simple bouillon.
Dairy Flavors
Butter: Butter, along with all
dairy products, contains an unusu-
ally wide range of lactones, but the
lactones are especially important in
butter flavors. g-Nonalactone can
play a very effective role at around
18 Flavor Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
PF1702_Wright_fcx.indd 18 1/13/17 11:55 AM

1,500 ppm in authentic style butter soy sauce flavors, but they scarcely and related roasted notes can
flavors, brightening the profile and convey authenticity. g-Nonalactone be higher and generate a similar
adding realism. can help considerably at around problem of lack of depth. The ideal
Milk and Cream: The same 300 ppm. level of this ingredient in peanut
is true of milk and cream flavors, Seafood: This ingredient can flavors is around 800 ppm.
but the levels are lower, 500 ppm provide a good counterbalance to Pistachio: Simple pistachio
being a good starting point. the pungent phenolic notes in all flavors are dominated by benzal-
seafood and seaweed flavors. 200 dehyde, but more realistic flavors
Savory Flavors ppm is an ideal level of addition. have a notable roasted note and
Beef: Flavorists struggle to g-nonalactone can be very benefi-
reproduce the characteristic Nut Flavors cial at 800 ppm.
brightness of barbequed or grilled Hazelnut: g-Nonalactone
beef with individual ingredients. forms a perfect counterbalance to Stone Fruit Flavors
Instead they all too often fall back the unsaturated ketones that play Peach: g-Nonalactone is a long
on the same old familiar process such an important role in defining way from being the dominant
flavors. g-Nonalactone, more this flavor category. If the ketones lactone note in peach flavors, but
than any other lactone, can help are overly dominant the resultant the addition of around 1,000 ppm
to achieve a part of this elusive flavor may be very characteristic can be very helpful by adding an
complex. Levels of use vary dra- but it can also tend to be a little attractive complexity to the main
matically depending on the effect thin. The lactone offsets this effect higher gamma lactones.
required, but 500 ppm is a good without in any way detracting from Apricot: Exactly the same com-
place to start. the recognizable character. Levels ments apply equally to apricot and
Chicken: The same comments vary, depending on the effect nectarine flavors but the ideal level
are true of chicken flavors, perhaps desired, starting around 200 ppm, of addition of this ingredient is a
to a slightly lesser degree. Again, but going up to 1,000 ppm in very little lower, nearer 600 ppm.
levels vary tremendously, but 500 bright hazelnut flavors. Plum: Plum flavors are more
ppm is also a good starting point. Peanut: Peanut flavors differ delicate than peach and apricot
Soy Sauce: This flavor category from hazelnut flavors in that the flavors so the ideal level of this
is deceptively difficult. A few ketone notes are often less promi- ingredient is even lower, around
obvious chemicals are dominant in nent, but in contrast, the pyrazine 400 ppm.
19

Flavor Bites
Tropical Fruit Flavors in “French” style vanilla flavors, ageing and the ubiquitous, but
Passion Fruit: g-Nonalactone where it performs well at 1,000 more costly, whisky lactone. It is
plays a useful role in passion fruit ppm. especially beneficial in rum flavors
in nature and this can be mod- Brown Sugar: The shoe is well because it also contributes help-
estly exaggerated in flavors to very and truly on the other foot here fully to the raw sugar note. An
good effect. A good starting point and g-nonalactone forms an impor- ideal level in lighter rum flavors
is 800 ppm. tant part of brown sugar flavors in is 200 ppm, rising to 500 ppm in
Mango: The same comments nature, adding depth and realism aggressive dark rum styles.
apply to mango flavors and the to flavors in the region of 800 ppm. Whiskey: Here, as with brandy
added creamy character is especially Chocolate: More modest levels and Cognac flavors, lower levels
attractive at levels around 600 ppm. are effective in all styles of cocoa are more appropriate and 100 ppm
Pineapple: Pineapple flavors and chocolate flavors. A good place is a good starting point. Outside
also fall into the same category to start is 200 ppm. the important category of rum
where a modest overemphasis of Coffee: The ideal level in flavors it is arguable that, unless
the natural effect can be beneficial. coffee flavors is quite subtle, 50 cost reduction is vital, whiskey
An ideal starting point is 600 ppm ppm, but the effect even at this lactone may be a better bet than
in this flavor category. level is still quite noticeable, g-nonalactone.
adding a hint of creaminess.
Brown Flavors To purchase a copy of this article or others,
Vanilla: g-Nonalactone can Spirit Flavors visit www.PerfumerFlavorist.com/magazine.
play a small part in rounding out Rum: This ingredient is useful
realistic vanilla bean flavors, but it in all spirit flavors, reproducing
is more suited to a dominant role something of the character of oak

Untitled-2 1 1/12/17 2:38 PM
Flavor
DEFINING
NATURAL How can the flavor industry overcome the challenges,
legislations and regulations of configuring the naturalness
of flavor substances?
PF1702_Lambert_fcx.indd 22 1/13/17 11:58 AM

n BY FANNY LAMBERT, Joseph Zucca, Biotechnology Department, MANE SA, Le Bar sur Loup, France;
B Christine Schippa, Analytical Department, MANE SA, Le Bar sur Loup, France
A
uthentifying the natural status of approaches: through purified enzymes, whole
flavors is more often than not a cells (fungi, bacteria, yeasts) or through physical
challenge that the indutsry faces. treatments.
When configuring the naturalness
of flavor substances, multilevel Legislation on Flavorings
approaches might offer more reliable results,
creating a more transparent supply chain, The aim of the legislation is to ensure the effec-
In Europe, the naturalness of food flavors is tive functioning of the market by providing a system
defined legally by regulations, especially European for regulation of flavors and food ingredients which
regulation CE 1334/2008. A substance can be con- is harmonized throughout the European Union.a
sidered “natural” when it comes from plant, animal The legislation also aims to ensure a high level
or microbial origin with an enzymatic, microbial or of human health and consumer protection, the
physical treatment. protection of consumer interests, fair practices in
In this context, biotechnology can be used food trade and the protection of the environment.
to obtain natural substances by three possible Guidance has been established to clarify issues
surrounding flavorings for use in food. Legislative
requirements on natural flavors are defined in
Regulation 1334/2008, adopted in 2008.
The legislative instrument gives the reference of
European Union legislation on natural flavorings
currently applicable and lays down the legisla-
tive requirements for flavorings and certain food
ingredients with flavoring properties for use in and
on foods.
The definition of a natural flavoring substance,
according to the European regulation, is as follows:
Article 3 (2) (c) - ‘Natural flavoring substance’
shall mean: a flavoring substance obtained by
appropriate physical, enzymatic or microbiologi-
cal processes from material of vegetable, animal or
microbiological origin either in the raw state or after
processing for human consumption by one or more
of the traditional food preparation processes listed in
Annex II. Natural flavoring substances correspond to
substances that are naturally present and have been
identified in nature.
The SNIAA (Syndicat National des Industries
Aromatiques Alimentaires), which is the French
National Association for Food Flavors Professionals,
invites the actors of the industry to guarantee the
conformity of the natural flavors through a high level
of scientific requirements. As it has been discussed at
a http://eurlex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:200
8:354:0034:0050:EN:PDF
23

Flavor
the SNIAA congress in January 2016 (Isabelle Girod- dictate not only the taste or odor quality, but also its
Quilain, January 14th 2016), multi-criteria visions intensity or detection threshold.
constitute the basis necessary to ensure compliance Authentifying the natural status of flavors is often
with regulation. Naturalness of aromatic substances a challenging problem. Besides GC/MS analysis
should be defined with the use of three criteria: the (identification of by-products), chiral separation of
naturalness of the substrate, the natural qualification enantiomers and isotope ratio mass spectrometry
of the process used to obtain said substances and the (IRMS) have been recognized as efficient tools for
analytical authentication of the products involved in characterizing the natural or synthetic origin of given
this procedure (F-1). chemical species. Commonly in nature, both enan-
tiomers are found even if one isomer is predominant
Authentifying the Natural Status in the mixture. It is very rare to find flavoring
substances with an enantiomeric excess of 100%. In
of Flavors the same way, very few, if any, aroma compounds
From a chemist point of view, a molecule are found to be “racemic”. The European Flavor
extracted from plants or chemically synthesised in Association (EFFA)b published its interpretation for
a laboratory is the same if the chemical structure is optically active flavoring substances in a guidance
identical. This introduces an issue in a regulation document in 2015: “mixture of optical isomers shall
process: to be applicable, it must be able to clearly be allowed in any ratio provided that all the isomers
differentiate between the same flavoring substance have been identified in nature”.
resulting from enzymatic catalysis or chemical syn- With this in mind, the determination of enan-
thesis. Furthermore, the interaction of compounds tiomeric ratios provides data to evaluate if chiral
with biological systems has long been shown to be compounds are present in a racemic form or not.
mostly stereo selective. These chiral enantiomers For many years now the overall content of active
components and their relative percent-
age determined with the use of effective
F-1. EFFA / SNIAA guiding principles for the production of natural methods were an accepted criterion in the
flavourings [8]. assessment of flavorings [18]. However, this
information is not an absolute evidence of
naturalness as not all chiral compounds are
Raw material prepared / found in a stable ratio of both enantiomeric
Raw material: processed: forms. As a result, if the analysis of chiral
Identified in nature (plant, Traditional food preparation discrimination is a great opportunity for
animal or microbial) processes (as defined in Annex II of
the EU regulation). quality control, it also has some limitations.
These restrictions are further developed in
the following points:
EFFA GUIDANCE 1. Enantiomeric excess can be dif-

ferent in various natural raw materials.
Traditional food Several analytical studies showed that lac-
preparation tones are found with specific enantiomeric
distributions depending on the raw material
and the molecule considered. In raspberry
for example, Dufossé et al (1994-1998) dem-
Identified in
Microbial / onstrated that g-dodecalactone is present
enzymatic with a high enantiomeric excess of the (R)
Nature
process
form even if both enantiomers are found
in nature. Krammer et al (2006) confirmed
these data and extended analysis to the
other lactones. T-1 illustrates these results:
Physical
process chiral distribution shows that g-decalactone
occurs in high enantiomeric purities while
homologous lactones, such as g-octa- and
g-nonalactone, are present only in minor
enantiomeric purity.
Natural flavouring substances and natural flavouring preparations b www.effa.eu

One of the most popular aromas in foodstuffs is the fruity compound ionone, which was identified as a flavor component of raspberries, carrots,
black tea and violet flowers.
2. During processing or storage a racemiza-

T-1. Enantiomeric flavor analysis of raspberry water
tion may occur and enantiomers ratios may phase extracts after freeze-drying. A multidimensional
vary. This can be illustrated with a hazelnut ketone gas chromatography equipped with chiral cyclodextrin
called filbertone. Both enantiomers are found in GC columns allowed a rapid determination of
nature and have a nutty, soft, butter impact however enantiomeric excess data [13].
it has been noticed that (+)-(E,R)-Filbertone has
an effect about 10 times lower than for (-)-(E,S)- R(+) S(-)
Filbertone. In nature, there is a slight excess of the d-Octalactone 39.8% 60.2%
(E,S)-isomer, the amount varies depending upon the g-Octalactone 64.6 % 35.4 %
source of hazelnut. The enantiomeric excess in the
g -Nonalactone 57% 43%
extracted filbertone is greater under mild processing
conditions (T-2). d-Decalactone 47.5% 52.5%
g-Decalactone 98.1% 1.9%
3. Ethyl ester of 2-methylbutyric acid is
d-Dodecalactone 66% 34%
another substance in which enantiomeric
distributions of chiral compounds showed g-Dodecalactone 99.5% 0.5%
a high excess of the
(S)-configuration. This T-2. Enantiomeric composition of filbertone in hazelnut extracts.
first observation is the main
reason which prompted Raw hazelnuts 80-85% (+)-(E ,S) and 15-20%(-)-(E ,R)c ee = 60-70%
some people to consider Roasted hazelnuts 71.5-72.5% (+)-(E,S) and 27.5-28.5% (-)-(E,R)c ee = 43-45%
racemic ester as artificial
even though literature c www.Leffingwell.com
25

Flavor
T-3. Enantiomeric distribution of 2-methylbutyric acid from carrots, black tea and violet flowers. The specific
various origins [11d ],[4e]. aroma of raspberry is formed from carotenoids and
has been studied by various authors for many years.
Origin R(+) S(-) Identified in raspberry fruits at first, results showed
a nearly strict homochirality with an enantiomeric
Strawberriesd <1% 99% excess of the R-isomer (99.9%). In order to answer
Veratum album d 5% 95 % authenticity related questions rapidly, these results
have led to the wrong conclusion that the detection
Chamomiled 32% 68% of a racemic a-ionone in fruit products shows that a
Rheum rhabarbarum e (Rhubarb) 36% 64% nature identical synthetic compound was added.
Still, there are also reports which show that
both chiral forms of a-ionone are found in nature
demonstrated a large enantiomeric distribution of the even if the R-form is predominant. Haarmann &
substrate 2-methylbutyric acid in nature due to the Reimer (1991) worked on a variety of foodstuffs
numerous possible pathways used by organisms to to determine the naturally occurring enantiomeric
produce 2-methylbutyric acid (T-3) [14]. composition of a-ionone in concentrates of violet
On the other hand, esterification of (S)-2- flowers, fresh raspberries, carrots, vanilla pods
methylbutyric acid with ethanol leads to varying as well as absolutes of Osmanthus fragrans and
results depending on the conditions applied. It Boronia megastigma. The published results dem-
has been demonstrated by Zucca et al (2003) that onstrated that the S-isomer was found at a level of
enzymatic process or soft thermal treatment result 5% in Darjeeling tea (by solvent extraction) [(R)/
in an ethyl ester with a high (S)-configuration excess (S) = 95/5], 3% in vanilla pods [(R)/(S) = 97/3] and
compatible with natural characteristics [(R)/(S) = 5% in carrots [(R)/(S) = 95/5] (both by headspace
1/99], while a more severe thermic treatment led to analysis). Boronia absolute has been found to
racemization of the ester (T-4). contain 9% of S-isomer and in raspberry also, there
In this case, literature data show that the enantio- were some S-isomer present even if it was found to
meric ratios of ethyl ester obtained by biotechnology occur in trace amounts (only 0.1%). These analytical
or chemical synthesis are not significantly different results are in concordance with the natural pathway
and cannot be the sole criteria for authentication of observed in plants for the synthesis of carotenoids
natural substances. derivative compounds. Literature demonstrates the
In conclusion, the enantiomeric distribution of presence of a large range of carotenoids varieties
natural molecules and the analysis of chiral dis- from which mixtures of a- (R and S) and b-ionones
crimination for authenticity have to be investigated have been produced (F-3).
carefully with regard to the interpretation of the Carotenoid-derived aroma compounds are
natural origin of flavoring substances. Multilevel important flavor substances in the scent of fruit
approaches should be considered for those kinds and flowers. These compounds are formed in
of flavor compounds to confirm the authenticity of three steps: the oxidative cleavage by carotenoid
natural substances. oxygenases, the enzymatic transformation to polar
intermediates, and the acid catalyzed conversion
4. Chiral analysis of ionones. One of the most into volatiles (F-4).
popular aromas in foodstuffs is the fruity compound Over the last years, the number of publications
ionone (F-2). a-Ionone is formed by enantioselec- on carotenoid cleavage enzymes (subsequently
tive enzyme catalyzed cleavage of carotenoids. It also named as carotenases – STEP I, F-3), have
was identified as a flavor component of raspberries, increased rapidly. These enzymes are isolated from
F-2. The ionones a and b

F-3. Carotenes found in nature
natural sources, for example from nectarine peel e-Carotene splits on the cleavage site 9, 10 (9', 10')
(Prunus persica var. nucipersica), flower petals of and leads directly to the formation of a-ionone (R
Osmanthus (Osmanthus fragrans var. aurantiacus), and S) (T-5).
or Japanese Green Tea (Camellia sinensis) and Plant CCDs have been shown to be involved in
volatile compounds have been investigated by many the continuous synthesis and degradation of carot-
research groups [1]. enoids and chlorophyll. These mechanisms are of
Osmanthus fragrans is a shrub native to East- critical importance in the maintenance and regula-
Asia belonging to the Oleaceae family and shows, tion of active photosynthesis and for adaptation to
by far, the highest diversity of carotenoid derived changing light conditions. Depending on its localiza-
aroma compounds among the flowering plants. tion, CDDs have various substrate specificities (T-3:
Among the over 100 identified volatiles, b-ionone,
a-ionone, dihydro-b-ionone, dihydro-b-ionol, and T4. Enantiomeric distribution of ethyl-2-methylbutyrate
cis- and trans-theaspirane are major components depending on esterification conditions. Reaction time
(F-5) [9; 10].
40H [20].
At the same time, Lashbrooke et al identi-
fied, isolated and characterized grapevine CCDs Ethyl-2-methylbutyrate
Esterification
(Carotenoid Cleavage Dehydrogenase) involved
conditions (R)-(-) (S)-(-)
in flavor and aroma related to apocarotenoid
production. They elucidated the biological role Enzymatic 1% 99%
of these genes and its respective enzymes. Their
study reports a summary of plant CCDs identified 150°C 1% 99%
in literature, including grapevine enzymes, with 170°C – 10 bars 4% 96%
cleavage sites, substrates and products showing
the presence of CCDs specific to e-Carotene. 280°C – 20 bars 40% 60%
27

Flavor
T-5. Summary of plant carotenoid cleavage enzymes identified and characterized in grapevine, strawberry
and sweet Osmanthus [15].
Species Enzyme substrates products
Zeaxanthin 3-hydroxy-b-ionone
Lutein 3-hydroxy-b-ionone
VvCCD1
Lycopene MHO
e-carotene Alpha-ionone
Vitis vinifera
VvCCD4a Neurosporene Geranylacetone
Lycopene 6-methyl-5-hepten-2-one
VvCCD4b Neurosporene Geranylacetone
z-carotene Geranylacetone
Zeaxanthin b-ionone
Fragaria ananassa FaCCD1 Lutein 3-hydroxy-b-ionone
b-apo-8’-carotenol 3-hydroxy-b-ionone
a-carotene a-ionone
Osmanthus fragrans OfCCD1
b-carotene b-ionone
VvCCD1 localized in the cytosol; VvCCD4a and Based on this conclusion, (R)-a-ionone pure
VvCCD4b localized in the chloroplast). This allows enantiomer biosynthesis has been realized by
considering the possibility to produce, by bioconver- genetic engineering. Katrin Schullehner (Phytowelt
sion, a large range of carotenoids derivatives and Green Technologies GmbH, Germany) shared her
in particular both enantiomers of a-ionone with studies on biosynthetic routes for ionone biosynthe-
specific ratios. sis during the Bioflavor International Conference in
Frankfurt (Sept. 2015).
To biosynthesize enantiomeric pure (R)-alpha-
ionone, Schullehner et al engineered a strain of E.
F-4. General steps for the conversion of carotenoids coli and proposed a pathway via the synthesis of
into flavour compounds in plants e-carotene and then its cleavage to (R)-a-ionone
(F-6). To do so, Phytowelt Green Technologies
CAROTENOID
GmbH had to engineer a specific lycopene epsilon
cyclase to optimize the carotenoid pathway (wild
STEP I: oxidative cleacage
type enzyme screening / directed evolution / clones
screening) and further used a carotene cleavage
Primary cleavage enzyme CCD to convert it to enantiomeric pure
product (R)-a-ionone. This CCD was isolated from plant
with a characterized activity on e-carotene and
STEP II: enzymatic transformation led to the biosynthesis of the (R) pure candidate
enantiomer.
On the other hand, J. Lopez [16] presented a
Non-volatile metabolite
work on the production of b-ionone by combined
(aroma precursor)
expression of carotenogenic and plant CCD1
genes in Saccharomyces cerevisiae. Integration of
STEP III: Acid catalyzed conversions various genes from the carotenoid pathway resulted
in carotenoid producing cells. Lycopene is then
transformed via a lycopene beta-cyclase widely
Aroma compound present in the plant kingdom (F-7). Various vectors
or cloning strategies were tried and resulted in a
final 0.63 ± 0.02 mg/g of b-ionone concentration.

F-5. Main volatile carotenoids derivatives volatiles (key odorants) identified in Osmanthus fragrans.
F-6. Ionone biosynthesis pathway in plants (Bioflavour 2015 - Phytowelt Green Technologies GmbH,
Germany)
Phytoene
z-carotene
Lycopene g-carotene b-carotene
d-carotene a-carotene b-ionone

lycopene epsilon
cyclase
e-carotene a-ionone + b-ionone
lycopene epsilon
cyclase
a-ionone
29

Flavor
F-7. a-Ionone biosynthesis pathway [16]
NATIVE PATHWAY
Acetyl-CoA
tHMG1
Mevalonic-CoA
IPP DMAPP HETEROLOGOUS PATHWAY

ERG20
DPP1
BTS1 crtYB
Farnesol X FPP GGPP Phytoene
X
LPP1 crtl
Squalene Neurosporene
crtl
Lycopene
Ergosterol crtYB
b-carotene
PhCCD1
HMG-CoA 3-hydroxy-3-methylglutaryl-CoA,
IPP isopentenyldiphosphate,
FPP farnesyl diphosphate,
b-ionone + C14 dialdehyde
GGPP geranylgeranyldiphosphate
Batch fermentations with this strain resulted in a Metabolic processes regulated by biological mol-
final specific concentration of 1 mg/g in 50 h. In this ecules are sensitive to stereochemistry and different
case, a b-ionone producing yeast platform has been reactions can be observed when comparing the
constructed. activity of pairs of enantiomers.
These studies prove that with an enlightened Aromatic substances present in foodstuff are
choice of enzymes used for the bioconversion, a submitted to the same law and aroma perception
chiral ratio specification can be set up. In these depends on the effectiveness of interactions between
cases, chiral analyses are not sufficient to answer the gustatory receptors and the flavor compounds.
authenticity related questions. Natural flavoring As a consequence, it is often believed that nature
substances are often showing high complexity provides pure enantiomers of chiral flavor compounds
which requires the application of combined analysis whereas it produces various ratios of stereoisomers
to guarantee the naturalness of the product on a with the predominance of one enantiomer. For many
strict scientific point of view. years now, the chiro-specific differentiation of opti-
cally active flavoring substances and the measurement
New Challenges and New of its relative percentages have created a powerful
tool in the assessment of natural flavors. However, for
Solutions some chiral flavor compounds, there is a wide varia-
The human organism is chiral and chiral recep- tion of enantiomeric distribution in nature. In such
tion is the primary criterion in biological activity. case, the assessment of their naturalness has to be

done by a combination of techniques, including but depending on the enzymes chosen in the biosyn-
not limited to chiral analysis. thetic pathway. In addition, European Regulation
In this context, issues surrounding chirality EC 1334/2008 defined precisely the “natural”
and natural authentication in food flavors are a definition of flavoring substances. It allows the use
good example to describe the new challenges of physical, enzymatic and microbiological treat-
for flavor and fragrance companies for analytical ments. These processes lead to the formation of
quality control and performance analysis. Any test natural molecules with analytical characteristics
method has its limitations with regard to accuracy, specific to the process used to produce them and
precision, sensitivity, linearity, reproducibility and not derived from aroma materials extracted from
specificity. Flavoring substances are often showing plants. Cutting-edge analytical tools are essential to
high complexity, which requires the application assess authenticity of natural flavoring substances,
of combined analytical methods. Besides chiral but these studies must nevertheless be comple-
separation of enantiomers, GC/MS analysis and mented with process scrutiny and auditing of the
isotope ratio mass spectrometry (IRMS) are receiv- manufacturing premises.
ing increased attention. Authentication of a natural
flavoring substance can also be done through
a comprehensive knowledge of the production Acknowledgements
process compatible with EU regulation. We would like to thank Eric Angelini for his
Since it is known that both enantiomers of expert advice on natural regulation.
a-ionone occur in many raw material containing
carotenoids, a detailed analysis of these qualities
References
is necessary and the chiro-specific analysis should
be completed by other data. Using a metabolic 1. S Baldermann, M Kato, P Fleischmann, N Watanabe. Acta
Biochim Pol. 2012; 59 (1):79-81 (2012). Biosynthesis of
engineering approach, we have shown that it is pos- a- and b-ionone, prominent scent compounds, in flowers of
sible to produce ionones with specific chiral ratio, Osmanthus fragrans.
(Continued on Page 34)
31

Untitled-1 1 1/9/17 2:08 PM
Untitled-1 2 1/9/17 2:08 PM
Flavor
(Continued from Page 31)

2. S Baldermann, Göttingen, Cuvillier, 2008. Carotenoid 13. GE Krammer, B Weckerle, S Brennecke, B Weber, G
oxygenases from Camellia sinensis, Osmanthus fragrans, and Kindel , J Ley, JM Hilmer, G Reinders, D Stöckigt, FJ
Prunus persica nucipersica: kinetics and structure. Hammerschmidt, F Ott, I Gatfield, CO Schmidt, HJ Bertram
Mol. Nutr. Res. 50: 345-350 (2006).
3. JM Barbosa-Filho, AA Alencar, XP Nunes, AC de Andrade
Tomaz, JG Sena-Filho, PF Athayde-Filho, MS Silva, MF 14. DA Krueger ACS Symposium Series 596; American
Vanderlei de Souza, EV Leitão da-Cunha Revista Brasileira Chemical Society: Washington, DC, 70−78 (1995). Detection
de Farmacognosia Brazilian Journal of Pharmacognosy 18(1): of adulterated fruit flavors. In Fruit Flavors: Biogenesis,
135-154, Jan./Mar. 2008. Sources of alpha-, beta-, gamma-, Characterization, and Authentication; Rouseff, R. L., Leahy,
delta- and epsilon-carotenes: A twentieth century review M. M., Eds.
4. M Dregus, HG Schmar, E Takahis, KH Engel, J. Agric. 15. JG Lashbrooke, PR Young, SJ Dockrall, K Vasanth, MA
Food Chem, 51, 7086–7091 (2003). Enantioselective Vivier BMC Plant Biology. 13:156 (2013). Functional
analysis of methyl-branched alcohols and acids in rhubarb characterization of three members of the Vitis vinifera L.
(Rheumrhabarbarum L.) stalks. carotenoid cleavage dioxygenase gene family.
5. L Dufossé, A Latrasse A, HE Spinnler, Science des aliments. 16. Lopez et al. a-ionone biosynthesis pathway. Santiago
1994. 14 : 17-50. Importance des lactones dans les arômes University - Bioflavour 2015.
alimentaires : structure, distribution, propriétés sensorielles
et biosynthèse. 17. SMM Malowicki, R Martin, MC Qia, J. Agric. Food Chem.
56, 4128–4133 (2008). Volatile composition in raspberry
6. L Dufossé, A Latrasse, HE Spinnler, Sci Aliments 14 :17- cultivars grown in the Pacific Northwest determined by
50 (1994). Importance des lactones dans les arômes stir bar sorptive extraction-gas chromatography-mass
alimentaires ; structure, distribution, propriétés sensorielles spectrometry.
et biosynthèse.
18. U Schäfer, J Kiefl, W Zhu, M Kempf, M Eggers, M Backes,
7. L Dufossé, G Feron, G Mauvais, P Bonnearme, A Durand, T Geissler, R Wittlake, K V. Reichelt, J P. Ley, G Krammer,
HE Spinnler J. Ferment. Bioeng. 86(2): 169-73 (1998). Engel and Takeoka; Importance of Chirality to Flavor
Production of g-decalactone and 4-hydroxy-decanoic acid in Compounds. Chapter 1. ACS Symposium Series; American
the genus Spridiobolus. Chemical Society: Washington, DC, 2015. Authenticity
Control of Food Flavorings - Merits and Limitations of
8. EFFA Guidance Document on the EC Regulation on Chiral Analysis
Flavouring (2015) p 47 Chapter 5.2: Geometric and optical
isomers. http://www.effa.eu/en/publications/guidance- 19. P Werkhoff , W Bretschneider, M Güntert, R Hopp, H
documents. Surburg Zeitschrift für Lebensmitteluntersuchung und
-Forschung A, 1431–4630, 192 (1991). Chirospecific
9. R Kaiser American Chemical Society, Washington, DC,
analysis in flavor and essential oil chemistry Part B. Direct
2002, p160. Carotenoid-derived aroma compounds in flower
enantiomer resolution of trans-a-ionone and trans-a-
scents, in winterhalter, P. and Roussef R., Eds., Carotenoid-
damascone by inclusion gas chromatography.
derived aroma compounds.
20. J Zucca, C Marin, M Schroeder 34th International
10. R Kaiser and P Kraft P, Chem. Zeit. 35, 8 (2001). Neue und
Symposium on Essential Oils (Würzburg, September 7-10
ungewöhnliche natur faszinierender blütendüfte.
2003). Enantiomeric behaviour of 2-methyl butyric acid
11. V Karl, J Guster, A Dietrich, B Maas, A Mosandl A. Chirality during yeast bioconversion from 2-methyl butanol and during
,6, 427–434 (1994). Stereoisomeric flavour compounds esterification by enzymatic or physical treatment.
LXVIII. 2-, 3-, and 4-alkyl-branched acids, ) part 2.
chirospecific analysis and sensory evaluation.
12. WA König, P Evers, R Krebber, S Schulz, C Fehr , G To purchase a copy of this article or others,
Ohloff, Tetrahedron 45: 7003–7006 (1989); corrigendum: visit www.PerfumerFlavorist.com/magazine.
Tetrahedron 48: 1771 (1992). Determination of the absolute
configuration of a-damascone and a-ionone from black tea by
enantioselective capillary gas chromatography.

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Untitled-2 1 5/27/16 1:21 PM

Fragrance
When it comes to product design,

a simple “like” is not enough. How
does consumer emotion play a
role in developing engaging and
successful products on the shelves?
36 Fragrance Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
PF1702_Q Research_fcx.indd 36 1/13/17 12:05 PM

n BY DANIEL BLATT, SVP, Research Services, Q Research
Solutions; MICHELLE NIEDZIELA, Scientific Director, HCD
roduct research traditionally assesses

cognitive, or System 2: reactions to
stimuli to guide product development.
To diagnose what is well liked and why, traditional
cognitive consumer product research typically utilizes
Likert scales, or check-all-that-apply attribute lists to
score different products. The consumer responds to
how they feel about the product with time allowed to construct
and rationalize their opinions.
Some research disciplines have advanced beyond cogni-
tive methods to measure System 1: subconscious reactions.
Studying the subconscious allows researchers to understand
consumers’ emotions that influence their behavior and
experience, yet cannot verbalize. Applied consumer neurosci-
ence is a growing field which measures the subconscious via
physiological responses. For example, the field of advertis-
ing research has been an early adopter of applied consumer
neuroscience. In advertising, it has been used to identify
such things as effectiveness (emotional engagement), impact
of branding moments, and to specify areas of ads that need
improvement. Applied consumer neuroscience reports have
been used to optimize communications in TV advertisements,
print ads, messaging, branding, social media and website UX.
Here it has become an increasingly popular tool for measur-
ing engagement with communications and for providing data
points to deliver relevant advertising experiences.
When consumers experience a product, they do so
5-dimensionally via the five sensory systems: taste, touch,
sound, sight and smell. Each of these senses becomes an
opportunity for communication of a product’s concept,
branding and even higher-order benefits (such as stress
relief, moisturization, etc.). These sensory communications
become part of the overall product and brand messaging as
well. Therefore, it is important to assure there is alignment of
37

Fragrance
product sensory attributes with brand and product purchased tropical or exotic fruits plug-in scented
concepts to ensure a positive and cohesive product oil air fresheners in the past six months. The panel-
experience. For example, the emotional qualities of lists were tested for both cognitive and subconscious
the fragrance should be aligned with the emotional responses to the four different products—identi-
communications of the package, the brand and the fied here as Product A, Product B, Product C and
advertising. When these pieces are not cohesive, Product D.
it can contribute to consumer dissatisfaction and
negatively impact consumer liking.
The need for understanding the emotional Test protocol and samples
responses in sensory and consumer studies has The consumers tried the four products in a
become more and more frequent and necessary in sequential monadic two-stage study over two days.
the last ten years. The studies were carried out following ASTM proto-
col, using eight identical
air flow controlled booths
which use positive airflow
Studying the subconscious to eliminate cross contam-
ination. In the first stage,
allows researchers to consumers entered a
pre-fragranced booth and
understand consumers’ provided ratings on liking,
emotions that influence their fragrance intensity and
other explicit measures.
behavior and experience, yet In the second stage,
neuro-physiological
cannot verbalize. procedures involved
measuring physiological
responses from electrodes
placed on the consumers’
The introduction of applied consumer neurosci- face (facial EMG), hand
ence in consumer product research is a relatively (Galvanic Skin Response)
new yet rapidly growing field. Q Research Solutions and wrist (heart rate
(Q) set out to examine the value of incorporating variability)
neuroscientific measurements in consumer product Electrodes are placed on
They entered the
subjects' face, hand and wrist
research. If we can measure the system 1 responses fragranced booth while to measure neuro-physiological
of subconscious reactions, could there be valu- wearing nose clips in responses for each fragrance.
able additional insights? How could going beyond order to avoid fragrance Photo courtesy of the authors.
measuring pleasure, or hedonics, to understand exposure until prompted;
experiences—which are not verbalized by consum- once seated they were instructed to remove the
ers—help guide product development? nose clip to start the test. Consumers were asked
To investigate, Q conducted a study employ- to sit and breathe normally for 15 seconds while
ing applied consumer neuroscience, working with physiological responses to fragrance exposure were
HCD’s HedonicsPlusa methodology to see if and captured. They then moved on to the next fragrance
how neuro-physiological testing would result in booth and repeated these steps.
enhanced emotional profiles, an improved under-
standing of consumer preferences and subsequently
provide better guidance for product development. Ratings
In the traditional explicit stage, 10 attributes
– happy, contented, comforted, refreshed, sex,
Materials and Methods energized, irritated, relaxed, sad and boring – were
Q & HCD chose to conduct the study with the assessed via a check-all-that-apply list. These were
four different tropical plug-in scented air fresheners, selected to cover positive and negative valence as
chosen because it is a lead olfactive direction within a well as high and low arousal.
well-developed category. The consumers who partici- Check-all-that-apply data was analyzed using
pated in the test were female, aged 18 – 60, who had a simple frequency table so that we can see the
percent of consumers who selected each attribute
a HedonicsPlus is a registered trade mark of HCD per fragrance. The higher the percent of consumers

T-1. Results from explicit testing
T-2. Results from neuro-physiological testing
who selected an attribute, the better that attribute profiles from the explicit measures yielded key
described the fragrance. Hedonic and intensity mea- insights. Namely most of the products were rated as
sures were analyzed using an Analysis of Variance happy and refreshed by the consumers (T-2).
with a Fisher LSD Post Hoc test. We found that by layering on applied consumer
neuroscientific measures, we uncovered additional
Results of the Explicit and understanding of emotional resonance. Positive
emotion was not as clear from the biometrics,
Neuro-physiological Testing for instance. Three of the four fragrance profiles
All of the fragrances tested scored parity for overall included negative valence with attributes such as
liking, a familiar problem within product testing (T-1). irritation, annoyance and negative arousal. Further,
Therefore, product development guidance would it revealed how the emotional reactions changed
need to come from other measures. The emotional over the time course of fragrance exposure. In the
39

Fragrance
F-1. Neuro-physiological responses to Fragrance D
case of one fragrance, we were able to measure how left to try to decide which is the best to move
the response which was initially neutral became forward with.
more approachable or welcoming towards the end of When a consumer approaches a product on shelf,
the experience. she may pop open the top to sniff it. Does she like
For Product A, the experience, as revealed by the it? Probably, it was a well-designed fragrance. But is
neuroscientific approach, was fairly neutral – even that enough to drive purchase? The product experi-
boring. There was a positive valence at the beginning ence is more than just a hedonic experience, there is
which began to significantly decrease over the period also an emotional and functional experience which
of exposure. The testing of Product A also showed a must be considered. Which is why in addition to
moment of significantly decreased negative valence. understanding how much consumers like a product,
With Product B, there was a decrease in positive we also need to assess attributes such as comforted,
valence immediately, followed by a decrease in energized, refreshed, happy etc. to understand if
negative valence. In other words, this fragrance was the product will meet all the needs of the consumer
arousing, but not immediately. The responses indi- beyond liking.
cated some disengagement with the fragrance with Seeing how the fragrance changed consumer
a combination of increased arousal and decreased perception over time based off of physiological
attention. measures has allowed us to better understand the
Product C was found to be arousing up front and consumer experience. For example, Fragrance D
for most of the experience. This was negative as well evolved over time, becoming more approachable,
as positive, however, resulting in a tension between signaling that this product would perform well over
the two responses. At the same time the consumers longer exposures in an in-use environment. While
found this fragrance to be less approachable, sug- first impressions are very important to the consumer,
gesting some distraction or disengagement. understanding how perception and experience
Product D had an overall negative valence reac- changes over time allows us to differentiate similar
tion and the arousal was sustained for half of the test samples in ways that traditional research cannot.
experience. The fragrance was initially aversive, These nuances can reveal large differences between
becoming more approachable and welcoming over samples, differences in experience that consum-
the period of exposure (F-1). ers may not even be aware of or able to articulate,
but that influence their overall perception of the
product.
Conclusions This novel holistic approach to consumer science
What does this all mean? will provide product developers and consumer
The fragrances we examined all scored well scientists with a sensitive and efficient way to better
hedonically. In fact, they were parity for liking. This understand consumer behavior and emotion, differ-
is a very common result in flavor and fragrance entiate changes to product attributes and make more
testing. A fragrance house is charged with making informed product design decisions.
several options to choose from and, of course, they
are able to offer really great, well-liked samples. To purchase a copy of this article or others,
Brand managers and product developers are then visit www.PerfumerFlavorist.com/magazine.

Where Delicious Innovation Begins
October 24–26, 2017

Hyatt Regency O’Hare
Rosemont, IL USA
(5 minutes from Chicago O’Hare International Airport)
SAVE THE DATE

Presented by: Produced by:
www.Flavorcon.com
Flavorcon17_SaveTheDate_FullPg.indd 1 1/10/17 2:48 PM

Flavor
Organoleptic Characteristics
of Flavor Materials
n BY JUDITH MICHALSKI, Senior Flavorist, abelei flavors; [email protected]
Organoleptic Evaluation Panelists

• Gerard Mosciano, Consulting Flavorist
• Deborah Barber, Senior Flavorist, FONA
Odor: @ 100%. Sweet, terpeney, carrot, woody,
• Cyndie Lipka, Senior Flavorist, Prinova tobaccolike and rooty.
• Susie Sadural, Senior Flavorist, Sensient Flavors Taste: @ 2 ppm. Sweet, fruity, oily, earthy and
• Tom Gibson, Vice President of R&D and Applications, slightly green.
Silesia Flavors Taste: @ 5 ppm. Carrot, oily, slightly spicy, terpeney
• Robert Pan, Principal Development Scientist, and slightly floral.
Givaudan Flavors Corp. Possible applications: This lovely oil will lend depth
and sweet, earthy character to root flavors like
carrot and beet and sweet spice flavors like anise,
Cucumber Pure Extract cinnamon and clove. Other areas where it will add
Source: Robertet richness are pumpkin, sweet potato, rose, tropical
GRAS, natural, Cucumis sativus L. flavors like mango, lychee and rambutan and veg-
Odor: @ 100%. Fresh, green, cucumber, vegetable- etable juice blends.
like and slightly rindy. Excellentia: www.excellentiainternational.com
Taste: @ 0.01%. Fresh, green, vegetablelike and
cucumber. Blood Orange Oil Sanguinello
Possible applications: Obviously this material will be Source: Global Essence
great in all flavors of its ilk. That being said, it will FEMA# 2825, CAS# 8028-48-6, natural, Citrus
equally grace melon flavors, especially green vari- sinensis L. variety Moro
eties like honeydew, fresh, green vegetables like Odor: @ 100%. Sweet, juicy, orange, fresh, waxy and
celery, green pepper and lettuces and some fresh peely.
fruits like guava and kiwi. Taste: @ 10 ppm. Sweet, citrus, orange, juicy and
Robertet: www.robertet.com slightly albedolike.
Taste: @ 20 ppm. Fresh, juicy, sweet and orange.
Golden Apple “S” Pure Possible applications: Of course this essential oil
Source: Robertet should be considered for use in all orange, tan-
GRAS, natural, Pyrus malus L. gerine, mandarin and citrus blend flavors. But at
Odor: @ 100%. Sweet, apple, green, trans-2-hexe- lower levels it will add a lovely subtle citrus depth
nallike, slightly winey, slightly waxy and fresh. to mocha, tropicals, peach, apricot and alcoholic
Taste: @ 0.02 %. Apple, fresh, ripe, slightly green flavors a la SoCo to name a few.
and pulpy. Global Essence:vwww.globalessence.com
Possible applications: This material is highly char-
acteristic of a golden delicious apple. Along with Orange Light Fraction WONF
apple flavors it will shine in pear, quince, banana, Source: Cvista
cider, kiwi, berry and combinations thereof. Natural
Robertet: www.robertet.com Odor: @ 100%. Sweet, waxy, orange, slightly grassy
and citruslike.
Carrot Heart Oil Taste: @ 5 ppm. Fresh, sweet and citruslike with top
Source: Excellentia notes of orange.
FEMA# 2244, CAS# 8015-88-1, natural, Daucus Taste: @ 10 ppm. Fresh, fruity, juicy, and citruslike
carota L. with orange top notes.
PF1702_Michalski_fcx.indd 42 1/13/17 12:06 PM

Untitled-2 1 10/31/16 1:29 PM
Flavor
Possible applications: As citrus greening disease cuts Taste: @ 1 ppm. Savory, metallic, meaty, cooked,
into the citrus oil harvest, extenders such as this onionlike and vegetablelike.
material will be very helpful in stretching cur- Taste: @ 2 ppm. Savory, metallic, mashed potatolike
rent and future supplies of orange oil, the basis and slightly fishy.
of orange, tangerine, mandarin, fruit punch and Possible applications: This molecule will reinforce
other flavors which contain it. cooked, savory notes in gravy, soup, potato, stew,
Cvista: www.cvista.com meat, fish, mushroom, onion, bacon, ham, veg-
etable and tomato flavors. It will also add depth to
Ethyl-2-methyl-3-pentanoate (aka Fruitaleur) cheese flavors like cheddar.
Source: Bedoukian Research Natural Advantage: www.natural-advantage.net
FEMA# 3456, CAS# 1617-23-8
Not yet found in nature. 1-Methyldithio-2-propanone
Odor: @ 100%. Sweet, ethereal, fruity, juicy and Source: DeLong Chemicals America
slightly tangy. FEMA# 4696, CAS# 122861-78-3
Taste: @ 1 ppm. Sweet, fruity and slightly candylike. Natural occurrence: Salmon and roasted sesame seeds.
Taste: @ 3 ppm. Sweet, fruity, juicy and ‘bright.’ Odor: @ 0.1%. Metallic, sulfurous, onion/garlic,
Possible applications: The sweet, ethereal, almost gassy, slightly meaty and cheesy.
effervescent nature of this ester will be much Taste: @ 1 ppm. Metallic, savory, meaty, onion/garlic,
appreciated in almost all fruits, especially, rasp- cheesy and cooked vegetablelike.
berry, apple, strawberry, pineapple, cherry and Taste: @ 2 ppm. Onion/garliclike, meaty, sulfurous
banana, as well as sparkling wines like champagne and cooked vegetablelike.
and prosecco and non-sparkling like white and Possible applications: The meaty, oniony quality of
red wine. this rather whiffy offering makes it a good candi-
Bedoukian Research: www.bedoukian.com date for savory flavors meat, bacon, onion, garlic,
shallot and pungent soft cheeses like brie, lim-
trans-2-Nonenol natural, 1% in EtOh burger and Époisses. Its sulfurous notes may also
Source: Natural Advantage enhance hard-boiled egg flavors.
FEMA# 3379, CAS# 31502-14-4, natural DeLong Chemicals America: delongchemicals.
Natural occurrence: Asparagus, cucumber, chicken com
fat, cognac, kelp, melon, prickly pear, pumpkin
and nectarine. 2-Propyl-4-methyl-1,3-oxathiane (synonym –
Odor: @ 1%. Fresh, green, cucumberlike, vegeta-
blelike and waxy.
4-tropical oxathiane)
Source: DeLong Chemicals America
Taste: @ 0.2 ppm. Green, waxy, cucumberlike and
FEMA# 4677, CAS# 1064678-08-5
fatty.
Not yet found in nature.
Taste: @ 0.4 ppm. Waxy, green, fatty and mutton/
Odor: @ 1%. Fruity, sulfurous, rubberlike, sweet and
tallowlike.
tropical fruitlike.
Possible applications: Best to keep the dosage of this
Taste: @ 0.5 ppm. Sweet, tropical fruitlike, and
very powerful alcohol on the lower side since it
slightly cooked onionlike.
presents an entirely different profile at higher
Taste: @ 1 ppm. Slightly savory, sulfurous, tropical
levels. At the lower levels it will add character
fruitlike and slightly onionlike.
notes to cucumber and melon flavors like water-
Possible applications: The sweet, sulfurous, fruity
melon and honeydew and fresh, green notes to
notes of this material will enhance the profile of
vegetables like green pepper, lettuce and celery.
fruits like guava, pineapple, passion fruit, white
Higher dosages will emphasize fatty, green notes
grape, rambutan, lychee and durian. Other flavors
characteristic of animal fats in mutton, lamb,
where it can be considered are green onion and
chicken and beef.
cooked meat flavors.
Natural Advantage: www.natural-advantage.net
DeLong Chemicals America: delongchemicals.
com
Methionyl butyrate natural
Source: Natural Advantage
FEMA# 4160, CAS# 16630-60-7, natural To purchase a copy of this article or others,
Natural occurrence: Cheese powder and passion fruit. visit www.PerfumerFlavorist.com/magazine.
Odor: @ 1%. Savory, metallic, fried potatolike,
slightly onionlike, overripe fruitlike, mushroom-
like and slightly cheesy.
PF1702_Michalski_fcx.indd 44 1/13/17 12:06 PM

Allured’s FFM BUYER’S GUIDE
SEARCH SUPPLIERS AND MATERIALS
EASY-TO-USE! CONVENIENT!
Find it in FFM Online !
In addition to the properties

and regulatory data found
here in print, FFM Online
provides even more
information on the flavor
and fragrance materials,
including:
• Molecular structure
• FCC reference
• RIFM reference
• FDA reference
• Council of Europe number
• EINECS
• Empirical formula
• Flash point
• And more!
Visit www.perfumerflavorist.com/ffm
Questions? Contact [email protected]
FFM Print-BuyersGuideAd.indd 1 12/16/16 3:49 PM

Celery seed and leaf oils

n BY BRIAN M. LAWRENCE, Consultant
C
elery is an annual Two less recognized celery vari- coarsely toothed at their apex arise.
or biennial member eties are A. graveolens var. filicium Each plant produces numerous
of the Apiaceae Crovetto which is cultivated in small, tightly-spaced, white five
(Umbelliferae) Egypt, as is A. graveolens var. seca- petal flowers aggregated in umbel-
family. Although linum Alef. (also known as Chinese lets and umbels. It is estimated
there are two well-known varieties celery). Celery (A. graveolens var. that there are typically 300 umbells
of Apium graveolens L., celery dulce) is an erect, herbaceous plant and 10–14 umbellates per plant.
seed oil is obtained by steam that grows to a height of 60–90 cm. The aggregated floral system
distillation of A. graveolens It has a succulent, shallow tap root attracts insects for natural cross-
var. dulce (Mill.) Pers. The with numerous small feeder roots. and self-pollination even within
other variety, A. graveolens The stem is branched, somewhat flowers on the same plant (Jamwal
var. rapaceum (Mill.) Gaudich, succulent, fistular (hollow), angular and Kaul, 1996).
possesses dark green leaves and is and ridged from which deeply The fact that A. graveolens
grown for its root tubers (celeriac). divided pinnate leaves that are var. dulce can be both cross- and
self-pollinated suggests that it
can be readily grown in various
environments. Once pollinated the
small two-seeded ellipsoid-shaped
schizocarp (split fruit) are formed.
It is estimated (Choudhary et
al. 1993) that the seed yield per
umbell is 5–7.5 and 1,654 seeds
weigh 1 kg. As with all Apiaceae
fruit, the essential oil is found in
the internal schizogenous cavities
(cells separated from each other)
in the oil ducts found longitu-
dinally along the seed. Because
celery has a complex floral biology,
selective hybridization is extremely
difficult, as a result new cultivars
have been developed by mass
selection and random hybridization
(Choudhary and Kaul 1992).
A study on 11 selected geno-
types by Choudhary and Kaul
determined that the environmental
(extrinsic) conditions were the
most influenced factors rather
than the intrinsic conditions for
the inheritability of plant height
and seed formation. Consequently,
the grower has to select a cultivar
based on its seed yield in his local
environment.
Celery, which is a long dura-
tion crop taking 190–210 days
PF1702_Lawrence_fcx.indd 46 1/13/17 12:08 PM

to mature, is grown for seed and it behaves as an annual during one batch (amount not given). The
seed oil production in northern first season (Sudheendram et al. average oil yield of celery seed
and eastern Europe, China, India, 1993). The authors determined the is 2.0–2.5%, which equates to a
several African countries and the maximum seed yield of 1540 kg/ha. field (plantation) oil yield of 20–30
USA (Krishnamurthy 2008). In could be attained when the seeds kg/ha. (Facooqui and Sreerama,
India (the main seed oil produc- are sown on June 1st. In the Punjab 2001). Sowbhagya et al. (2007)
ing country) the main cultivation region, the average seed yield is examined the effect of grinding
regions are in the districts of 1,000–1500 kg/ha., however, with either in combination with cooling
Amritsar, Ferozepur and Jalandhar good farming practices, a selected or not. They found that through
(Punjab), Ladwa (Haryana) and cultivar yields of 1,600 kg/ha. or the use of a mini plate mill, the
Saharanpur (Uttar Pradesh). greater can be achieved. Bhagat et seeds were flaked whereas the seed
Smaller scale production can al. (1980) reported that the highest was powdered using a hammer
also be found in Jagadhari (U.P.), oil yield of celery seed could be mill. On distillation, flaking the
Karnal (Haryana) and Kirama, found in seed harvested 185–198 seed resulted an oil yield of 1.76%
Ludhiana and Shami (Punjab) days after sowing. compared to yield of 1.42% if
(Malhotra, 2012). The annual The steam distillation of celery the seed was powdered. Also
production of celery seed in India seed is very time consuming. The the authors found that the water
in 2008 was ca. 40,000 metric amount of time is dependent on soluble portion of the oil containing
tons of which 70–75% is exported the charge size, whether the seed the phthalides could be recovered
mainly to the USA (Sowbhagya et is whole or flaked (comminuted), using hexane extraction of the
al. 2010). the dryness of the seed and the condensate from steam distillation.
Although celery is an important pressure and wetness of the steam Previously, celery seed oil has been
cash crop in NW India, when (Verghese, 1990). the subject of review (Lawrence,
grown in the Bangalore region According to Malhotra (2012) 1980, 1989, 1985, 1989, 1990,
of Karnataka (Southern India), it takes 10–12 hours to steam distil 1995, 1998 and 2005).
47

Celery seed oil was found by with molecular weights of 400 or ‘celebrity’ and ‘RRL-85-1’ cultivars
Lawrence (1970) to contain the less are solubilized in the extract. grown in an experimental field in
following major constituents: Furthermore, Moyler noted that Jammu–Tawi (Kashmir, India).
the oil contained limonene (74%), They found that the ‘RRL-85-1’
a-pinene (0.1–1.1%) 5-pentyl-1,3-cyclohexadiene, cultivar, which was developed by
b-pinene (t–1.5%) pentylbenzene, b-selinene, the Regional Research Laboratory
sabinene (t–0.8%) valerophenone, 3-butylphthalide in Jammu–Tawi, yielded seeds with
myrcene (0.5–3.1%) (3%) and sedanoic anhydride the highest total phthalide content.
limonene (58.0–75.5%)
(2.3%). In contrast, he reported Momin et al. (2000)
p-cymene (t–1.0%)
the CO2 extract contained 60% characterized b-selinene,
pentylcyclohexadiene (0.5–3.5%)
pentylbenzene (1.0–4.0%) lipids and 40% oil, which in turn 3-butyl-4,5-dihydrophthalide
linalool (0.1–1.5%) contained limonene (8%), 3-butyl and 5-allyl-2-methoxyphenol in a
b-elemene (1.5–3.5%) phthalide (10%) and sedanoic hexane extract of celery seed.
b-caryophyllene (0.1–2.4%) anhydride (14%). Celery seed harvested from the
b-selinene (8.0–15.9%) Fischer et al. (1991) used Saharanpur area of Uttar Pradesh
3-butyl-4, 5-dihydrophthalidea (0.5–6.0%) high-speed counter-current was subjected to hydrodistillation
butyl-3a, 4, 5, 6-tetrahydrophthalideb chromatography and a multi-layer by Chowdhury and Kapoor (2000)
(0.1–2.0%) oil separator-extractor to examine to produce an oil in 2.2% yield.
butyl phthalide (0.1-6.0%) the aroma-relevant components Analysis of the oil using GC/MS
ligustilide (0.1–2.5%)
of a commercial sample of celery only revealed it possessed the fol-
aalso
balso
known as sedanenolide or senkyunolide seed oil. Using a solvent system lowing composition:
known as sedanolide
of acetonitrile–t.butyl methyl
ether-hexane in a 10:3:10 ratio, a-pinene (1.0%)
Moyler (1989) reported that the authors were able to separate b-pinene 1.0%)
limonene (0.2%)
the yield of oil produced by steam sedanenolide, 3-butyl phthalide,
b-phellandrene (0.4%)
distillation and an extract of celery (E)-butylidene phthalide, sedano-
penthylbenzene (6.8%)
seed produced by subcritical CO2 lide, (Z)-butylidene phthalide and linalool (0.8%)
extraction was 2.5–3.0% and 3.0%, benzyl benzoate. b-elemene (1.3%)
respectively. He noted that under Choudhary and Kaul (1992) a-humulene (1.9%)
the subcritical conditions lipids compared the phthalide content of b-selinene (29.2%)

trans-carveol (1.7%)
caryophellene oxide (3.8%) T-1. Comparative percentage composition of celery seed oils
b-eudesmol (3.0%)
3-butyl phthalide (10.6%) Compound Oil 1 Oil 2
isovaleraldehyde - 0-t
A number of other compounds, a-pinene 0.3 0.2
which were listed as constituents, b-pinene 2.1 1.2-1.6
are not included because they sabinene 0.2 t
were incorrectly identified. myrcene 1.4 1.3-1.4
Celery seed, which was limonene 50.1 63.7-65.5
obtained from two cultivation b-phellandrene - 0.3-0.6
areas of Punjab and one in Kanpur
(Z)- b-ocimene - t
(Uttar Pradesh, India), were sepa-
rately subjected to hydrodistillation g-terpinene - 0–t
by Philippe et al. (2002). Analysis p-cymene t t
of the oils was performed using pentylcyclohexa-1,3-diene 3.6 3.9-4.5
GC/MS only. The results of this 1-octen-3-yl acetate - t
study in which kessaue was found pentylbenzene 0.7 0.4- 0.7
as a minor constituent of each oil
trans-limonene oxide t 0 –t
can be seen in T-1. The oils from
dihydrocarvone* 0.5 t -0.3
Kanpur and one of the regions of
Punjab were similar, which is why trans-menth-3-en-1-ol 0.2 0–t
they were combined. linalool 0.1 t – 0.1
Wei and Shibamoto (2007) b-elemene 0.2 0.2 – 0.3
screened a number of com- b-caryophyllene 0.7 0.7 – 0.8
mercially available oils for their trans-pinocarvyl acetate - 0–t
antioxidant activity, among which
a-humulene - 0–t
was a sample of celery seed oil.
The only components of the oil phellandral† 1.9 0-0.6
the authors characterized were g-selinene 0.4 0.2-0.4
limonene (74.6%) and b-selinene a-guaiene - 0.2
(16.0%). The authors found both drima-7,9(11)-diene† - 0-0.3
limonene and celery seed oil pos- dihydroagarofuran - 0.2
sessed inhibitory activity toward allo-aromadendene - 0.2
malonaldehyde formation from
b-selinene 22.2 11.2-11.4
squalene or UV–irradiation.
Kurobayashi et al. (2008) a-selinene - 2.7-2.8
examined the enhancement of kessane 7.6 2.2-2.3
celery on the flavor of chicken ar-curcumene - 0–t
broth. They found the key aroma valencene - 0-t
constituents of celery seed oil were trans-carveol 0.2 t
3-butylphthalide, sedanolide and valerophenone† 0.3 t-0.5
sedanenolide.
caryophyllene oxide 0.2 t-0.2
Sowbhagya et al. (2010)
examined the effect of spraying elemol 0.1 0-t
four different enzymes (cel- eugenol - 0-t
lulose, protease, pectinase or a-eudesmol t 0-t
viscozyme) onto celery seeds, b-eudesmol 0.4 0.3-0.4
mixed and incubated at 45° C myristicin - 0-t
for 30–120 min. (Viscozyme is a 3-butyl phthalide 1.8 1.4-1.6
commercial mixture of a pectinase
sedanolide 0.3 0.2-0.3
and a fungal glucanase). After
drying the seed it was powdered sedanenolide 0.2 2.9-3.8
to pass through a BSS mesh size t = trace (<0.05%)
*correct isomer not identified
20 sieve and subjected to steam † incorrect identification
49

distillation. The authors found the

use of the enzymes increased the T-2. The effect of enzyme treatment of celery seed on the percentage
oil yield from 1.8% to 2.2–2.3% composition of the oils
depending upon the enzyme.
Analysis of the oils using cellulose, Compound Control C-oil V-oil
viscozyme or no treatment on b-elemene 0.6 0.8 0.4
the seed by GC-FID and GC/ myrcene 0.5 0.3 0.3
MS revealed there were some limonene 63.9 82.2 67.7
quantitative differences in the oil g-terpinene 0.7 t t
compositions as shown in T-2. pentylbenzene 1.1 1.4 1.1
Khalid and Hussein (2012) ana-
carvone 0.2 0.2 0.2
lyzed a number of oils produced
b-caryophyllene 0.1 0.4 0.2
by hydrodistillation from celery
seed grown in Egypt using differ- b-selinene 16.4 9.0 17.6
ent fertilization regimens. The oils a-selinene 2.6 1.4 2.8
were analyzed using GC/MS only. caryophyllene oxide 0.7 0.2 0.7
A summary of the results of this 3-butyl phthalide 5.3 1.1 3.9
study are shown in T-3. sedanenolide 5.7 1.1 2.1
Freshly harvested A. graveolens
sedanolide t t t
var. dulce plants were subjected
to either simultaneous distillation C-oil = cellulose-treated seed
V-oil = viscozyme-treated seed
(Lihens-Nickerson)–extraction
using methylene chloride as the
solvent or direct solvent extraction
using diethylether as the solvent
T-3. Comparative percentage composition of celery seed oil produced
(Wassenhove et al. 1987). Analysis
from plants grown with and without liquid manure treatment
of the celery plant oil using GC/
MS only resulted in the character- Compound Oil 1 Oil 2
ization of 1-methyl-4-ethylhexane,
a-pinene 0.3 t
a-thujene, a-pinene, camphene,
sabinene 1.9 0.1
sabinene, b-pinene, myrcene,
p-cymene, limonene, (Z)- and b-pinene t 0.1
(E)-b-ocimene, g-terpinene, an myrcene 1.8 2.0
isomer of allo-ocimene, pentyl- p-cymene 0.3 t
cyclohexadiene, terpinen-4-ol, limonene 36.7 37.5
b-caryophyllene, a-humulene, b-ocimene* 0.6 t
b-selinene, a-selinene and butyl linalool 0.1 0.1
phthalide.
trans-p-mentha-2,8-dien-1-ol 1.2 t
Unfortunately, the authors
did not present any quantitative 1-methyl-4-acetylcyclohexene † 0.1 0.1
information. GC/MS analysis of limonene oxide * 0.1 0.2
the solvent extract of the fresh menthofuran † 0.2 0.1
celery plants resulted in the menthol † 0.1 0.1
characterization of 3-methyl- a-terpineol 1.1 0.1
4-ethylhexane, a- and b-pinene, dihydrocarvone * 0.6 0.9
myrcene, limonene, an isomer
p-mentha-1(7),8(10)-dien-9-ol 1.1 t
of b-ocimene, g-terpinene,
terpinolene, pentylcyclohexadiene, dodecane 0.1 t
butyl phthalide and linoleic acid. citronellol 0.1 t
Wassenhove et al. also exam- carveol* 0.5 0.8
ined a phthalide fraction of the geranial † 0.1 t
Likens-Nickerson oil isolation carvone 7.1 8.5
and found that the fraction phellandral † 0.1 t
comprised butyl hexahydroph-
trans-pinocarvyl acetate 0.3 1.8
thalide, (Z)-butylidene phthalide,

cnidilide, (Z)-ligustitide, butyl
T-3. Comparative percentage composition of celery seed oil produced phthalide, trans-neocnidilide,
from plants grown with and without liquid manure treatment (Cont.) cis-neocnidilide, senkyunolide and
(E)-ligustilide, the major pholides
Compound Oil 1 Oil 2 being trans-neocnidilide and
cis-carvyl acetate 0.1 0.9 senkyunolide.
b-elemene t 0.1 Wassenhove et al. (1990)
examined the volatile composi-
tetradecane 0.1 t
tions in oils produced by the
b-caryophyllene 0.1 t Likens–Nickelson simultaneous
a-humulene 0.1 0.1 distillation and extraction process
(E)- b-farnesene 0.1 t of four cultivars (‘Blancato’, ‘Avon
ar-curcumene 0.2 t Pearl’, Golden Sparten’ and
b-selinene 21.6 23.1 ‘Lorat’) of blanching celery and
a-selinene 0.1 0.1 five cultivars (‘Monarch’, ‘Tropa’,
‘Cobra’, ‘Correcta’ and ‘Snehvide’)
caryophyllene oxide 0.3 t
of celeriac. The oils were analyzed
sedanolide 10.4 11.4 using GC-FID and GC/MS and
sedanenolide 10.5 11.3 the results of this study are shown
Oil 1 = no liquid manure treatment of plants
in T-4.
Oil 2 = liquid manure treatment of plants The free and glycosidically-
t = trace (<0.05%) bound volatiles found in fresh
* correct isomer not identified
† incorrect identification celery were examined by Tang et
al. (1990) using GC/MS only. The
51

volatiles characterized in fresh leaves and roots of a celery cultivar root and leaf extracts can be seen
celery were as follows: grown in Lithuania. The authors in T-7.
used GC-FID and GC/MS as their The authors inferred that
(Z)-3-hexenol (0.86)a method of analysis. The authors although the use of supercritical
hexanol (0.12) found that the extract yields varied fluid CO2 as a solvent to extract
b-pinene (0.02) from 0.52–1.59% (roots) and celery roots and leaves, the low
2-pentylfuran (0.04)
0.56–1.26% (leaves). The composi- yield of volatiles makes the process
p-cymene (0.02)
tions of the volatiles found in the uneconomical.
limonene (0.27)
g-terpinene (0.03)
camphor (0.01)
pentylbenzene (0.01) T-4. Comparative percentage range of volatiles of four cultivars of
cis-verbenol (0.02) blanching celery and five cultivars of celeriac
trans-carveol (0.03)
b-caryophyllene (0.04) Blanching Celeriac
a-selinene (0.02) Compound
celery volatiles volatiles
butyl phthalide (0.87)
(E)-butylidene phthalide (0.18) 3-methylbutanal 0.2- 0.6 1.5-4.0
sedanenolide (20.40) 2-methylbutanal 0.1-0.3 0.7-1.5
(Z) ligustilide (2.18)
2-methylhexane 0.1 0.4-1.1
sedanolide (4.39)
psoralen (0.27) pyridine - 7.6-9.1
9-methoxypsoralen (0.06) hexanal 0.1-5 0.2-10.8
4-methoxypsosalen (0.02)
furfural 0.1-0.6 2.1-4.7
linoleic acid (1.78)
4,9-dimethoxypsoralen (0.24) 3-methyl-4-ethylhexane 0.5-0.9 7.2-12.3
a = ppm
a-thujene 0.1 0.1-0.4
a-pinene 0.4-1.2 0.2-0.4
camphene <0.1-.01 <0.1
Trace amounts of a-pinene,
myrcene, d-3-carene, a-terpineol, sabinene 0.2-0.4 0.4-0.9
a dihydrocarvone isomer, 3-pentyl- b-pinene 1.8-5.1 7.1-14.0
4,5-dihydrophthalide, (E)-ligustilide myrcene 0.7-1.1 2.1-6.6
and scopolotein were also found p-cymene 0.3-0.6 1.1-2.1
among the fresh celery volatiles.
limonene 18.7-36.7 13.8-29.4
D’Antuono et al. (2002) col-
lected the celery trimming waste (Z)-b-ocimene 2.1-7.5 2.6-4.9
materials from the ‘Darklet’ celery (E)-b-ocimene <0.1-0.2 0.1-0.2
cultivar produced from plants g-terpinene 6.2-16.4 1.3-8.0
grown with different nitrogen pentylcyclohexadiene 0.2-0.4 0.3-0.9
levels and subjected them to
terpinen-4-ol <0.1 <0.1
hydrodistillation. The results of the
analyses of the oils by GC/MS only b-caryophyllene 0.4-1.1 0.3-0.5
can be seen in T-5. a-humulene 0.1 <0.1
Oils produced from celery b-selinene 0.2-0.9 0.1-1.8
leaves (fresh and dried), which a-selinene <0.1-0.1 <0.1
were obtained from stalk celery
butyl hexahydrophthalide <0.1-0.1 <0.1-0.2
grown in Estonia, were the subject
of analysis by Orav et al. (2003). (Z)-butylidene phthalide <0.1-0.2 0.1-0.6
The components characterized in cnidilide <0.1 0.1-0.3
the fresh leaf oil (0.37% yield) and (Z)-ligustilide 0.1-0.7 0.2-0.5
dried leaf oil in 3.8% yield can be butyl phthalide 0.3-0.9 0.4-1.6
seen in T-6.
trans-neocnidilide 0.6-2.1 0.4-3.9
Sipailiene et al. (2005) exam-
ined the volatiles found in the cis-neocnidilide 0.1-0.4 0.5-4.1
various processes used to make a senkyunolide 1.1-4.8 0.4-1.2
range of supercritical fluid CO2 (E)-ligustilide <0.1-0.1 <0.1
extracts of the comminuted dried

T-5. Comparative percentage composition of the oils produced from the celery wastes from plants grown
under different nitrogen levels
Compound O 60 a 180 240 300

a-pinene 1.4 0.7 1.2 0.1 -
myrcene 1.5 0.9 0.9 0.1 -
1,8-cineole 0.8 0.5 0.2 0.1 0.1
limonene 32.5 51.7 51.3 10.7 4.0
p-cymene 3.6 2.5 2.7 1.0 0.6
g-terpinene 2.6 1.2 1.3 0.5 0.4
terpinen-4-ol 2.5 - - 0.1 -
b-caryophyllene 7.8 3.8 5.7 8.1 10.0
a-humulene 2.3 0.4 0.6 0.7 0.9
a-selinene 7.2 7.2 7.1 9.5 11.4
b-selinene 4.1 1.0 1.0 1.4 1.6
phthalidesb 33.6 30.6 27.9 67.6 71.0
Oil yield 4.9a 6.8 6.8 4.8 3.7
a = kg/ha; b = total phthalides
T-6. Comparative percentage composition of fresh and dried leaf oils

of Apium graveolens A leaf oil of A. graveolens of
Nigerian origin was reported by
Compound Fresh leaf oil Dried leaf oil Ehiabhi et al. (2006) to contain the
a-pinene 0.2 0.2 following constituents:
sabinene 0.2 0.2
b-pinene (1.1%)
b-pinene 0.4 0.4
limonene (40.5%)
myrcene 1.3 1.3 (Z)-b-ocimene (12.5%)
a-phellandrene 0.1 0.4 g-terpinene (8.8%)
p-cymene 0.1 0.1 b-caryophyllene (10.5%)
a-humulene (2.2%)
limonene 70.3 62.4
b-selinene (16.3%)
b-phellandrene 0.1 0.3 a-selinene (1.3%)
(Z)-b-ocimene 10.1 10.5 neophytadiene (3.1%)
(E)-b-ocimene 0.3 0.2
g-terpinene 2.3 1.6 Trace amounts (<0.1%) of
p-mentha-1,3,8-triene t t a-pinene, camphene, a-copaene,
1-phenyl-2-butene † 0.3 0.3 zingiberene and (E)-phytol were
b-caryophyllene 0.1 0.2 also found in the oil.
b-farnesene* t Sellami et al. (2012) used
viridiflorol 0.1 0.1 GC-FID and GC/MS to examine
the composition of oils produced
phthalide isomer* t 0.1
by hydrodistillation from leaves,
phthalide isomer* 0.3 0.8 stalks and roots of A. graveolens
phthalide isomer* 0.7 1.7 var. dulce grown in the region
apiole 0.1 0.7 of Soliman (N.E. Tunisia). The
farnesol* 0.1 0.1 compositions of the various oils are
phthalide isomer* 2.9 4.9 presented in T-8.
trans-pinocarvyl acetate
Saleh et al. (1998) analyzed an
oil produced by hydrodistillation
t = trace (<0.05%)
*correct isomer not identified of the whole plant of A. graveolens
† incorrect identification
var. filicinum that was grown in
53

Giza, Egypt using column chroma-

tography, GC-FID, GC/MS and T-7. Comparative percentage composition of the volatiles found in the
low pressure liquid chromatog- supercritical fluid CO2 extract of celery roots and leaver
raphy. The oil, produced in 2.3% Compound root volatiles leaf volatiles
yield, was found to contain the a-pinene 0.1 0.2
following constituents: camphene 0.2 –
b-pinene 0.5 0.2
a-pinene (6.6%)
b-pinene (0.1%) myrcene 0.2 9.1
sabinene (0.4%) ethyl hexanoate 0.1 –
myrcene (20.3%) octanal 0.3 –
a-phellandrene (0.4%) methyl heptanoate – 0.6
o-cymene (0.4%)
limonene 21.9 32.2
limonene (15.3%)
(Z)-b-ocimene (0.2%) (Z)-b-ocimene 0.5 –
g-terpinene (1.2%) (E)-b-ocimene – 0.3
p-cymenene (1.2%) g-terpinene 0.5 0.1
terpinolene (0.7%) methyl octanoate – 0.1
p-mentha-1,3,8-triene (8.8%)
fenchone 0.2 –
2-methylprop-1-enyl-cyclohexa-1,3-diene*
(0.1%) linalool 1.6 –
6-nor-butyl-cyclohepta-1,4-diene*(2.2%) (E, E)-allo-ocimene – 0.2
b-caryophyllene (0.7%) limonene oxide* – 0.1
a-humulene (0.2%)
camphor 0.1 –
b-selinene (1.0%)
myristicin (4.1%) pentylbenzene 0.8 0.1
elemicin (0.1%) menthol 0.5 –
3-butyl phthalide (0.5%) ethyl octanoate 0.3 –
apiole (3.4%) trans-carveol – 0.3
sedanenolide (2.8%)
carvone 17.7 0.2
sedanolide (20.6%)
3,5-dimethylbenzyl (E)-2-decenal 0.2 –
3,4-dimethylbenzoate* (0.7%) methyl nonanoate – 0.1
*incorrect identification isobornyl acetate 1.3 –
(E, Z)-2,4-decadienal 0.3 –
undecanone* – 0.1
Finally, it is interesting to (E, E)-2, 4-decadienal 0.4 –
note how Ogura and Watanabe
methyl decanoate – 0.2
(2011a) synthesized the four
myrtenyl acetatet 0.1 –
stereoisomers of sedanolide and
determined the odor-threshold of trans-carvyl acetate – 0.2
(3S,3aR)-sedanolide was 1.3x10-2 g-nonalactonet 0.2 –
ppm. It was found to possess a a-cubebene – 0.1
natural celery leaf, herbal odor a-copaene – 0.2
with a strong bitterness. Ogura 1-tetradecene 0.4 –
and Watanabe (2011b) also tetradecane 0.4 –
synthesized two stereoisomers of b-caryophyllene 0.5 1.8
sedanenolide (also called senkyu-
a-humulene 0.3 4.3
nolide) and two stereoisomers of
allo-aromadendrene 0.2 –
butyl phthalide. They determined
the (S)-(-) isomers of sedaneno- 9-epi-b-caryophyllenet 0.1 –
lide and butyl phthalide were 0.14 germacrene D – 0.7
ppm and 0.07 ppm, respectively. b-selinene 1.5 1.8
Both isomers were found to d-selinene – 6.0
possess a celery stem and a fresh a-selinene – 1.3
celery leaf-like odor. neryl propionatet – 0.4
g-cadinene – 0.5

References
T-7. Comparative percentage composition of the volatiles found in the
B.M. Lawrence, unpublished data (1970).
supercritical fluid CO2 extract of celery roots and leaver (Cont.)
B.M. Lawrence, “Celery Seed and Leaf
Compound root volatiles leaf volatiles Oils” In: “Progress in Essential Oils”.
d-cadinene – 0.6 Perfum. Flavor. 5(1), 56-58 (1980); 5
(21, 34) (1980); 8 (3), 71-71 (1983); 10
caryophyllene oxide 1.0 0.7 (5), 93-94 (1985); 14 (5), 52-53 (1989);
3-butyl phthalide 11.6 12.6 15 (5) 57-58 (1990); 20 (1), 52-53
(1995); 24 (4), 37-39 (1998); 30 (7),
(Z)-3-butylidene phthalide 1.8 0.4 73-74 (2005).
sedanenolide 4.8 –
N.R. Bhagat, M.L. Maheshwari and M.W.
sedanolide 7.0 – Hardas, “Effect of seed maturation
octadecane 0.3 – on essential content of celery (Apium
graveloens L.).” Indian Perfum. 24 (3),
ethyl hexadecanoate 2.4 – 121-123 (1980).
(Z)-falcarinolt 1.7 –
F. van Wassenhove, P. Dirinck and
methyl linoleate 1.6 – N. Schamp, “Analysis of the
t = tentative identification key components of celery by
* correct isomer not identified two dimensional capillary gas
chromatography.” Bioflavour ’87, 137-
144. Edit
T-8. Comparative percentage composition of the leaf, stalk and root S.D. Schneider, Walter de Gruyter , Berlin,
Germany (1987)
oil of Apium graveolens vor. dulce
D. A. Moyler, “CO2 extraction of essential
Compound Leaf oil Stalk oil Root oil oils. Part III. Pimento berry, coriander
a-thujene 9.9 14.0 12.4 and celery seed oil.” Flavors and Off-
Flavors. Edit. G. Charalambous, 263-
a-pinene t 0.9 0.5 280. Elsevier. Sci Pub., Amsterdam,
sabinene – – 1.0 The Netherlands (1989).
b-pinene – – 0.3 J. Verghese, “In the Kaleidoscope: Celery.”

Perfum. Flavor., 15 (3), 55-59 (1990).
a-terpinene 0.7 – 0.1
limonene 3.6 1.7 0.9 F. van Wassenhove, P. Dirinck, G. Vulsteke
and N. Schamp, “Aromatic volatile
1,8-cineole – – 2.2 composition of celery and celeriac
phenol† – 4.9 1.7 volatiles.” Hort Sci., 25, 556-559
(1990).
g-terpinene 2.4 1.6 5.2
terpinolene – – 0.5 J. Tang, Y-G. Zhang, T. G. Hartman,
R.T. Rosen and C-T. Ho, “Free
linalool – 0.8 0.1 and glycosidically bound volatile
camphor – 0.6 0.3 compounds in fresh celery (Apium
gravedens L.)”. J. Agric. Food Chem.,
borneol 2.1 – – 38, 1937-1940 (1990).
geraniol 0.3 0.6 –
S. Sudheendra, A.A. Farooqi, R. Lokesh
thymol 0.7 0.7 0.3 and B. Raju, “Influence of sowing
myrtenyl acetate – – 0.3 date on growth, yield and essential oil
content of celery (Apium graveolens
a-terpinyl acetate – 0.1 – L.). Indian Perfum., 37 (4), 327-329
eugenol – 3.0 1.1 (1993).
methyl eugenol – 3.3 1.7 M. Jamwal and B.L. Kaul, “Preliminary
b-caryophyllene 1.4 0.4 – studies on pollination system of celery
(Apium graveolens). Indian Perfum.,
b-selinene 0.4 7.5 8.9 40 (4), 103-106 (1996).
spathulenol – – <0.1
M.M. Saleh, F.A. Hashem and K.W.
3-butyl phthalide 3.9 2.0 14.8 Glombitza. “Cytotoxicity and in vitro
(Z)-3-butylidene phthalide 38.4 30.5 30.5 effects on human cancer cell lines
of volatiles of Apium graveolens var
apiole 0.8 0.7 1.7 filicinum”. Pharm. Pharmacol. Lett., 8
3-butyl-4,5-dihydrophthalide 34.2 24.1 12.3 (2), 97-99 (1998).
nonadecane – 0.3 0.1 A.R. Chowdhury and V.P. Kapoor,
eicosane – 0.5 1.3 “Essential oil from the fruit of Apium
graveolens.” J. Med. Aromatic Plants
† incorrect identification Sci., 22, 621-623 (2000).
55

F. van Wassenhove, P. Dirinck, G. Vulsteke A. Orav, T. Kailas and A. Jegorova, Y. Kurobayashi, Y. Katsumo, A. Fujika, Y.
and N. Schamp, “Aromatic volatile “Composition of the essential oil of Morimitsa and K. Kubota, “Flavor
composition of celery and celeriac dill, celery and parsley from Estonia.” enhancement of chicken broth from
volatiles.” Hort. Sci., 25, 556-559 Proc. Estonian Acad. Sci., Chem., 52 boiled celery constituents.” J. Agric.
(1990). (4), 147-154 (2003). Food Chem., 56, 512-516 (2008).
N. Fischer, B. Weinreich, S. Nitz and F. A.A Farooqi and B.S. Sreerama, “Celery in: H.B. Sowbhagya, P. Srinivas and N.
Drawert. “Applications of high-speed Cultivation of medicinal and aromatic Krishnamurthy, “Effect of enzymes
counter-current chromatography for crops. Revised edition.” 389-393, on extraction of volatiles from celery
the separation and isolation of natural University Press, Hyderabad, India seeds.” Food Chem., 120, 230-234
products.” J. Chromatogr., 528, 193- (2004). (2010).
202 (1991).
A. Sipailiene, P.R. Venskutonis, A. Sarkinas D. Oguro and H. Watanabe, “Synthesis and
D.K. Chowdhary and B.L. Kaul, “Volatile and V. Cypiene, “Composition and sensory evaluation of all stereoisomers
aroma constituents of celery (Apium antimicrobial activity of celery (Apium of sedanolide.” Tetrahedron, 67, 777-
graveolens L. var. dulce, cv. ‘RRL-85- graveolens) leaf and root-extracts 781 (2011 a).
1’”. Indian Perfum., 36(1), 17-19 (1992). obtained with liquid carbon dioxide.”
Acta Hort., 677, 71-77 (2005). D. Oguro and H. Watanabe, “Asymmetric
D.K. Chowdhary and B.L. Kaul, “Genetic synthesis and sensory evaluation of
parameters of celery (Apium O.S. Ehiabhi, U.U. Edet, T.M. Walke, sedanenolide.” Biosci. Biotechnol.
graveolens L.)”. Indian Perfum., 36(4), J.M. Schmidt, W.N. Setzer, I.A. Biochem., 75, 1502-1505 (2011 b)
297-299 (1992). Ogunwande, E. Essien and O.
Ekundayo, “Constituents of essential S.K. Malhotra, “Celery.” Handbook of Herbs
R. A. Momin, R.S. Ramsewak and M.G. oils of Apium graveolens L., Allium and Spices”. Second Ed., Vol 2, 249-
Nair, “Bioactive compounds and cepa L. and Voacanga Africana Staph. 267, Woodhead Publishing, Oxford,
1,3-di[(cis)-9-octadecenol 1]-2-[(cis, from Nigeria.” J. Essent. Oil Bear. U.K. (2012).
cis)-9, 12-octadecadienoyl ] glycerol Plants, 9, 126-132 (2006).
from Apium graveolens seeds. Journal K.A. Khalid and M.S. Hussein, “Effect of
of Agricultural Food Chemistry. 48, H.B. Sowbhagya, S.R. Sampathu and N. cattle and liquid manures on essential
3785-3788 (2000). Krishnamurthy, “Evaluation of size oil and antioxidant activities of celery
reduction on the yield and quality of (Apium graveolens L.) fruits.” J.
A.A. Farooqi and B.S. Sreeramu, “Celery.” celery seed oil.” J. Food Engineer., 80, Essent. Oil Bear. Plants, 15, 97-107
In:“Cultivation of medicinal and 1255-1260 (2007). (2012).
aromatic crops.” pp.308-312, University
Press, Hyderabad, India (2001). A. Wei and T. Shibamoto, “Antioxidant I.H. Sellami, I. Bettaieb, S. Bourgou, R.
activities and volatile constituents of Dahmani, F. Limam and B. Marzouk,
J. Philippe, G. Suvarnalatha, R. Sankar and various essential oils.” “J. Agricultural “Essential oil and aroma composition
S. Suresh, “Kessane in Indian celery and Food Chemistry, 55, 1737-1742 of leaves, stalks and roots of celery
seed.” J. Essential Oil Res., 14, 276-277 (2007). (Apium graveolens var dulce) from
(2002). Tunisia.” J. Essential Oil Res., 24, 513-
K.S. Krishnamurthy, “Celery.” Chemistry 521 (2012).
L.F. D’Antuono, R. Neri and A. Moretti, of Spices. Edits. V.A. Parthasarahy,
“By-products of vegetable celery B. Chempakam and T.J. Zachariah,
(Apium graveolens L. var dulce) as To purchase a copy of this article or others,
pp. 401-412, CABI, Wallingford, UK
potential source of flavours.” Acta visit www.PerfumerFlavorist.com/magazine.
(2008).
Hort., 576, 327-331 (2002).

Worldwide Sources
CHINA COLOMBIA
EGYPT
HAITI
INDIA
57
PF1702_WWS_fcx.indd 57 1/13/17 12:09 PM

Worldwide Sources
58 Worldwide Sources Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
PF1702_WWS_fcx.indd 58 1/13/17 12:09 PM

Ad Index
Advertiser Web site Page

Allured’s Flavor & Fragrance Materials www.PerfumerFlavorist.com/FFM 45
Aroma Aromatics & Flavours www.aromaaromatics.com 43
Aurochemicals, Inc. www.aurochemicals.com 35
Axxence Aromatic GmbH www.axxence.com 15
Bedoukian Research, Inc. www.bedoukian.com 9
Berjé, Inc. www.berjeinc.com Cover 3
Cilione Srl www.cilione.com 47
Ernesto Ventos SA www.ventos.com 32–33
Flavorcon www.flavorcon.com 41
Fleurchem, Inc. www.fleurchem.com 56
Gulcicek Kimya www.gulcicek.com 5
Gusmer Enterprises, Specialty Products www.gusmerenterprises.com 31
Hangzhou Grascent Co., Ltd. www.grascent.com 19
Indukern www.indukern-ffingredients.com 7
MilliporeSigma sigma-aldrich.com/flavors-fragrances Cover 2
Natural Advantage www.natadv.com 17
Organica Aromatics www.organicaaroma.com 51
Penta Manufacturing Co. www.pentamfg.com Cover 4
Symrise www.symrise.com 1
Vigon International, Inc. www.vigon.com 3
Xiamen Bestally Biotechnology Co., Ltd www.bestally.com.cn 21
Yongzhou Samshiang Flavours & Fragrances Corp. www.samshiang.com 11
59
PF1702_Ad Index_fcx.indd 59 1/13/17 12:09 PM

Endpoint.
60 Endpoint Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com
PF1702_Endpoint_fcx.indd 60 1/13/17 12:10 PM

n RACHEL GRABENHOFER, Managing Editor, Cosmetics & Toiletries
O
Editor’s note: Adapted from R Grabenhofer, Unexpected Paths to
Sunscreens, Cosm & Toil 132(1) (Jan 2017)
nce upon a time, science fiction would

have us believe a remote scan could
physically teleport us through space
and time, instantly zapping away the
headaches of an outer space commute.
As it turns out, this wasn’t too far from
the truth. We can be transported, or
rather our likenesses can, via Facetime,
Skype or Facebook Live. It’s not exactly
what sci-fi writers had in mind, but we reached nearly the same conclusion
in an indirect, completely unexpected way. I sense this may be the path to
future F&F development.
This is not to say the discovery and development of traditional flavor
and fragrance materials shouldn’t continue. Indeed, this is the crucial
lifeblood of the industry. But insights from peripheral disciplines could
uncover entirely new approaches to taste and smell experiences, catapult-
ing beyond incremental molecule design tweaks. How?
61

Endpoint.
Take semiotics, the study of meaning-making, The extent to which these systems are intertwined
for example. A new reviewa explores how food and and appeal to emotion are the epitome of what
language share “modes for making meaning and fragrance design is all about. How could this insight
wielding power in human societies,” especially benefit the F&F industry? A few interesting areas on
through the multiple senses they engage. According which we’ve previously reported are described here,
to the review, these interrelationships seem self- to help us to think outside the perfume bottle.
evident because both speaking/communicating and
eating seem so necessary to human existence.
Color Me Yummy
Four analytics are proposed to study how these
The influence of color on flavor is well-known. A
two systems are intertwined: language through food,
few years ago, color supplier for food and beverages,
language about food, language around food, and
D.D. Williamson, conducted an informal taste testb
language as food. The goal is to help researchers
with 24 students who were presented carbonated
analyze how food and language acquire symbolic
drinks colored brown, pink or colorless (clear), and
meaning and market value.
a semioticreview.com/index.php/thematic-issues/issue-food-and- b perfumerflavorist.com/flavor/research/Study-Reveals-
language/40-tasty-talk-expressive-food-an-introduction-to-the- Color-Affects-Taste-Perception--200479401.html?utm_
semiotics-of-food-and-language.html source=Most+Read&utm_medium=website&utm_
campaign=Most+Read#sthash.Uk920MvA.dpuf
Insights from peripheral disciplines could uncover entirely new approaches to

taste and smell experiences.

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 1/10/17 2:46 PM

Endpoint.
asked to describe how each drink tasted. The three Crunchy: Yogurt with a granola or muesli add-in
beverages were the same flavor: lemon-lime. and similar products made up 7% of new items
The colorless soft drink was accurately described using texture marketing in 2016. Also popular were
as lemon-lime or citrus by 81% of the testers. A small products that mixed soft and crunchy textures.
segment said it was flavorless. The brown-colored Creamy: Creamy foods made up 4% of 2016’s
drink was described as sweet or fruity by 34% of the new texture-driven products, and companies
testers. Cola was the next flavor identified by 15% of rebranded existing products to show off their smooth
the testers; nearly half did not offer a flavor descrip- textures.
tion. The pink drink was described as fruity, berry or Crispy: Thin is in, at least for chips, biscuits and
sweet by more the one-third (38%). Other responses pizzas. Labels for baked goods stressed the crisp-
included “cola, “ginger-ale” and/or flavorless. Of the ness of products in order to appear authentic and to
three, the pink drink was identified as the favorite. appeal to the health and wellness market.
Drink density: Finally, drinks with textures and
health properties, including energy gels and bever-
ages with chia or other hard seeds, rose in popularity
How might texture and feel in 2016, making up 2% of new products.
push new F&F limits? How How might texture and feel push new F&F
limits? Warming or crackling fragrances? Flavor that
might texture pair with color, reassembles as you eat it? How might texture pair
with color, flavor, scent and collective experiences?
flavor, scent and collective And what about sound? All gimmicks aside, we’re
experiences? And what about now entering that familiar concept of cross-modal
perception.
sound? All gimmicks aside,
we’re now entering that Sweet, Creamy Sound
Last month, we discussed how music influences
familiar concept of cross-modal the way we think.e As The Daily Mail reported,
food scientists found they can alter the sensation of
perception. creaminess in chocolate by playing different sounds
to people as they eat it. Soft, harmonious notes
made dark chocolate taste creamier whereas short,
Prior to this study, the color of plates on which sharp dissonant notes plucked on a violin made same
food was served was foundc to influence taste chocolate taste sharper or bitter.
perception. White, round plates signified a sweeter Skin care developers wonder whether music
taste. The authors of the study said these findings could improve or boost the sense of skin hydration.
may be due to specific learned associations, or some How might it impact F&F development? Perhaps
sort of familiarity/novelty effect. integrating sound into fragrance atomizers? Or
What could F&F take from these findings? utensils that serve up flavor with forte?
Product and packaging colors are the most obvious In the end, the goal is to elicit an emotion that
implications, to appeal to the primary senses. But consumers respond to and will pay for. While the
what about these “learned associations” might be answers may not lie in color textures and sounds,
leveraged in F&F development? Could targeted something that provides “nearly the same conclu-
marketing extend from demographics to collective sion” certainly lies in the imagination.
experiences?
e cosmeticsandtoiletries.com/research/universitydata/Synesthesia-
is-Music-to-Our-Feel-and-Taste-Receptors-402629836.
A Feel for Flavor html#sthash.inYuBRO9.dpuf
Taste is more than just flavor. It integrates mouth-
feel, sensory cues, texture and more—and textures
are grabbing the attention of evolving consumer To purchase a copy of this article or others,
visit www.PerfumerFlavorist.com/magazine.
taste buds, according to a recent report.d
c perfumerflavorist.com/flavor/research/Study-a-Plates-Shape-and-
Color-Influences-Taste-Perception.html#sthash.v1kkBaTs.dpuf
d perfumerflavorist.com/flavor/trends/A-Bunch-of-Crunch-
for-2017-408605465.html#sthash.HcYnDTi3.dpuf

Untitled-1 1 1/9/17 2:06 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 Naturally derived flavor and fragrance ingredients. All items are Food Grade Kosher and Organic Compliant.
For a complete list of all our natural, natural identical and synthetic ingredients visit us at www.pentam fg.com
■■ACETAL ■■TRANS-2-OCTENAL ■■PROPYL ■■5,6,7,8-TETRAHYDRO- ■■TRITHIOACETONE

■■ACETIC ACID ■■2-OCTEN-4-ONE THIOACETATE QUINOXALINE ■■TURPENTINE
■■ACETOL ■■3-OCTYL ACETATE ■■D-PULEGONE ■■2,3,5,6-TETRAMETHYL ■■L-TYROSINE
■■ACETONE ■■OCTYL BUTYRATE ■■PYRAZINE PYRAZINE
■■2,4-UNDECADIENAL
■■ACETYL BUTYRYL ■■OLEIC ACID ETHANETHIOL ■■THEASPIRANE ■■DELTA-
■■ALLYL HEPTOATE ■■PIPERINE ■■2-PYRIDINE ■■THEOBROMINE UNDECALACTONE
■■ACETOPHENONE ■■PRENYL ACETATE METHANETHIOL ■■2,2-(THIODIMETHYL- ■■TRANS-2-UNDECENAL
■■ALPHA-DAMASCONE ■■PRENYL MERCAPTAN ■■QUININE ENE) DIFURAN
■■UNDECYLENIC ACID
■■BETA-DAMASCONE ■■L-PROLINE ■■RHODINOL ■■THIOGERANIOL ■■VALENCENE
■■3,4-DIMETHYL-1,2- ■■PROPIONALDEHYDE ■■D-RIBOSE ■■THIOPHENOL ■■GAMMA-
CYCLOPENTADIONE ■■PROPIONIC ACID ■■RUM ETHER ■■THYMOL CRYSTALS VALEROLACTONE
■■DIMETHYL DISULFIDE ■■2-PROPIONYL ■■SAFRANAL ■■DELTA- ■■VALERALDEHYDE
■■CIS-JASMONE THIOPHENE ■■SCLAREOLIDE TRIDECALACTONE ■■VALERIC ACID
■■MESITYL OXIDE ■■PROPYL ACETATE ■■SKATOLE ■■TRIETHYL CITRATE
■■METHYL ALCOHOL ■■PROPYL ALCOHOL ■■VALSPICE
■■STEARIC ACID ■■2,4,6-TRIISOBU- ■■VANILLIN
■■MYRCENE ■■PROPYL BUTYRATE TYL-5,6-DIHYDRO-
■■DELTA- ■■PROPYL CAPROATE ■■STYRALLYL ACETATE 4H-1,3,5-DITHIAZINE ■■VANILLIN ACETATE
NONALACTONE ■■PROPYL CAPRYLATE ■■STYRALLYL ALCOHOL ■■TRIMETHYLAMINE ■■VANILLIN
■■CIS-6-NONENAL ■■PROPYL DISULFIDE ■■STYRALLYL ISOBUTYRATE
■■2,6,6-TRIMETHYLCY- ■■4-VINYL GUAIACOL
■■CIS-6-NONENOL ■■PROPYLENE GLYCOL ISOBUTYRATE CLOHEX-2-ENE-1,
■■4-NONANONE ■■PROPYL ■■SUCCINIC ACID 4-DIONE ■■VITAMIN E
■■CIS-6-NONENAL ISOBUTYRATE ■■GAMMA-TERPINENE ■■2,3,5-TRIMETHYL ■■WINTERGREEN OIL
■■3-NONEN-2-ONE ■■PROPYL MERCAPTAN ■■TERPINYL ACETATE PYRAZINE ■■XYLITOL
■■2,4-OCTADIENAL ■■PROPYL-2- ■■DELTA- ■■2,4,5-TRIMETHYL ■■D-XYLOSE
■■3-OCTANOL METHYLBUTYRATE TETRADECALACTONE THIAZOLE ■■ZINGERONE
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: [email protected] Web: www.pentamfg.com
PF1702_penta_1702.indd 1 1/9/17 1:40 PM

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February 2017 | Vol. 42 no.

PF1702_cover.indd 1 1/13/17 2:22 PM

42 Organoleptic Characteristics of Flavor Materials

60 Endpoint: Thinking Outside the Perfume Bottle

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

PF1702_TOC-Masthead_fcx.indd 2 1/13/17 2:35 PM

4 Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1702_TOC-Masthead_fcx.indd 4 1/13/17 11:43 AM

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

PF1702_EdNote_fcx.indd 6 1/13/17 11:44 AM

Summer Johnson to Lead IFRANA’s Communications

Hershey Hands Michele Buck a Sweet Presidential Treat

Hershey Losing Ground to Start-ups?

PF1702_Industry_fcx.indd 8 1/13/17 11:46 AM

Firmenich Nominates Master Howard Smith, Jr. Appointed

Nathalie Lorson and Tony Reichert are the most

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

PF1702_Industry_fcx.indd 10 1/13/17 11:46 AM

Q&A: EU’s Regulation Progression

Perfumer & Flavorist: What are some areas of

Alexander Mohr: More than concerns, I see

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

PF1702_Industry_fcx.indd 12 1/13/17 11:46 AM

P&F: The Brexit decision earlier this year

PF1702_Industry_fcx.indd 13 1/13/17 2:39 PM

it is not linked to the fact

AM: The safety and quality of the products have

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

PF1702_Industry_fcx.indd 14 1/13/17 11:46 AM

PF1702_RMB_fcx.indd 16 1/13/17 11:47 AM

We also carry Natural

Combine both at 1.66ppm

For sample requests: [email protected]

TECHNOLOGY IMPROVING TASTE!

p000_pf_natadv_mushroom.indd 1 1/10/17 2:00 PM

n BY JOHN WRIGHT, [email protected]

PF1702_Wright_fcx.indd 18 1/13/17 11:55 AM

PF1702_Wright_fcx.indd 19 1/13/17 11:55 AM

20 Flavor Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1702_Wright_fcx.indd 20 1/13/17 11:55 AM

22 Flavor Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1702_Lambert_fcx.indd 22 1/13/17 11:58 AM

PF1702_Lambert_fcx.indd 23 1/13/17 11:58 AM

EFFA GUIDANCE 1. Enantiomeric excess can be dif-

Natural flavouring substances and natural flavouring preparations b www.effa.eu

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

PF1702_Lambert_fcx.indd 24 1/13/17 11:58 AM

2. During processing or storage a racemiza-

PF1702_Lambert_fcx.indd 25 1/13/17 11:58 AM

F-2. The ionones a and b

26 Flavor Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1702_Lambert_fcx.indd 26 1/13/17 11:58 AM

PF1702_Lambert_fcx.indd 27 1/13/17 11:58 AM

Species Enzyme substrates products

28 Flavor Vol. 42 • February 2017 | Perfumer & Flavorist www.PerfumerFlavorist.com

PF1702_Lambert_fcx.indd 28 1/13/17 11:58 AM

Lycopene g-carotene b-carotene

d-carotene a-carotene b-ionone

e-carotene a-ionone + b-ionone