Introduction

44
Flavor and Fragrance Chemisy FYS wi Dr. Turk H CH 3 OH O O OH H O HO OCH 3

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Transcript of Introduction

Page 1: Introduction

Flavor and FragranceChemistry

FYS with Dr. Turk OH CH3

OH

O

O

OH

H

O

HOOCH3

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CHO

citral limonene

O

OOH

CHO

furaneol 3(Z)-hexenal

From Lemons and Strawberries,

To Lavender and Rose...

HO

linalool

HO

lavandulol

OH O

rose alcohols beta-damascenone

O

rose oxide

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From Sandalwood and Amber,

To Musk and Cedarwood...

OH

beta-santalol

O

ambrox

O

muscone

OH

cedrol

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--- perhaps the most primitive and the most powerful of our five senses.TASTE

& SMELL

In some cases, stripping nature of c h e m i c a l s t h a t c a u s e t h e s e wonderful sensations for use in household products, fine fragrances, and foods depletes many of our natural resources.

Did you know the popular

odor of musk comes from

a deer?

Did You Know...

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provides a way to make molecules with exactly the same sensory properties as many natural products - not only can this make these chemical ingredients cheaper, but…

This can help preserve

The continual harvest of natural resources to isolate the chemicals responsible for their flavors and odors has driven the PRICE of these ingredients UP!!

$$$

our Natural Resources!

Chemical Synthesis

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can also identify molecules with new and interesting structures that have odor qualities that can not be reproduced in nature!

Chemical Synthesis

OH3C

(R)-Muscone“very nice musky note,rich and powerful musk”

1200 times strongerthan muscone

O

O

CH3(R,Z)-Nirvanolide

“intense musky, fruity,powdery odor”

Obtained via research and chemical

synthesis

Odor Threshold = 61 ppb 0.05 ppb

Obtained from a glandular secretion of

musk deer

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Burberry: Burberry Brit, Burberry Touch, Society…

Calvin Klein: CK One, Crave, Escape, Eternity, Obsession, Truth

Cristian Dior: Dior Addict, Fahrenheit, Poison

Estee Lauder: Beautiful, Intuition, Pleasures

Ralph Lauren: Chaps, Polo, Romance

Tommy Hilfiger: Freedom, Tommy Girl, Tommy for Men

Heard of any of these companies

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> 75 % of all these were created by chemists and perfumers or flavorists who work at LARGE fragrance companies such as:

Givaudan, NJ, NY, CA, + locations in nearly 40 other countries

International Flavors and Fragrances, NJ, NY, GA, Fl, + locations in nearly 40 countries

Firmenich, NJ, NY, Fl, MN, CA, + locations in nearly 40 other countries

Top 3

Smaller

companies

Symrise, Takasago, Degussa, Rhodia, Sensient Technologies, Proctor and Gamble, Frutarom, Sensient, Danisco, Bedoukian, Unilever, and

MORE…

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There are hundreds of companies that create flavorings and fragrance ingredients.

Their names never appear on the perfume bottle or the bag of potato chips. All the liquid scents sold by the Giorgio Armanis, Vera Wangs, or Ralph Laurens, are not, in fact, created by Mr. Armani or Ms. Wang or Mr. Lauren at all.

How does this work in INDUSTRY?

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The Perfume Brief

Say Miuccia Prada wants a fragrance…

“I want the smell of bitter apples frozen in a Chinese snow”

Or

“I want the scent of a young girl swimming in a dark Mediterranean sea...”

Prada’s marketing team goes to work

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FiFi Awards 2005

PRADA FRAGRANCE, Prada

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Regarding Perfumery, an article published on CNNMoney.com (January 21, 2004) titled:

States: “A good nose and a good head for chemistry are two key traits for perfumers…”

“The field is small. There are only about 300 members of the American Society of Perfumers and likely no more than 1,000 official perfumers worldwide.”

“A low headcount has helped keep the price for top talent high, said Steve Herman, a chemist in the fragrance industry who teaches in a graduate cosmetic science program.”

“A junior perfumer may start out making $60,000… but perfumers who come up with formulas for hit fragrances can easily command six figures.”

“Getting into the field usually requires a bachelor's degree in chemistry and time spent working as a lab technician at a fragrance house. But there are some perfumers who don't have college degrees… Once you prove you have a keen sense of smell, you may serve as apprentice to a senior perfumer for five years, or the company may send you to perfumery school…”

Six-Figured Jobs, Take 3

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Did You Know?????

Approximately 80 - 90% of whatyou perceive as TASTE is actually

due to the sense of SMELL???

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1701 Observations that some flowers provided essential oil on steam distillation 1759 Reaction of oil of amber with fuming nitric acid gave a musky odor 1800 Investigations into ambra component chemistry 1833 Empirical formula reported for anethole, borneol and camphor 1834 Isolation of cinnamic aldehyde Preparation of nitrobenzene 1837 Isolation of benzaldehyde 1843 Methyl salicylate determined as main component of wintergreen oil 1853 Preparation of benzyl alcohol Synthesis of aliphatic aldehydes 1856 Synthesis of cinnamic aldehydes 1859 Preparation of aldehydes from pyrolysis of calcium formate mixtures 1859-60 Large-scale preparation of salicylic acid 1863 Preparation of benzaldehyde 1865 Determination of structure of benzene 1866 Structure of cinnamic acid determined 1868 Synthesis of coumarin 1869 Discovery of heliotropin 1871 Structure of heliotropin determined 1874 Synthesis of vanillin from guaiacol 1876 Discovery of phenylacetic aldehyde 1875-77 Synthesis of cinnamic acid 1877 Production of anisaldehyde from p-hydroxybenzaldehyde 1878 Structure of terpin hydrate determined 1880 Quinolines discovered

A Little History...

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1884 Identification of d-limonene and dipentene 1885 Structure of terpineol determined 1888 Discovery of nitro musks 1889 Discovery of citronellal 1890 Synthesis of heliotropin from saffrole 1891 Discovery of Rhodinol 1893 Synthesis of ionone 1894 Structure of alpha-pinene determined 1898 Discovery of Musk Ketone 1903 Discovery of methyl heptin carbonate and homologues Fundamental work on aromaticity Methyl nonyl acetic anhydride 1904 Isolation of muscone Glycidic method of synthesizing aldehydes 1905 Synthesis of cinnamic alcohol 1905-08 Hydroxycitronellal prepared and marketed 1908 Discovery of gamma-undecalactone 1913 Discovery of farnesol 1919 Discovery of cyclamen aldehyde Synthesis of linalool1921 ‘Chanel No. 5’ 1923 Discovery of alpha amyl cinnamaldehyde Discovery of nerolidol 1926 Identification of muscone structure Structural determination work on ambra, civet Exaltone®

1927 Ambrettolide®

1928 Civetone®, Exaltolide®

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1933 Structural determination of jasmone Jasmone1934 Synthesis of muscone 1946 Perfection of Wallach’s isoprene rule for terpenoids 1947 Structural determination of irone 1949 Ambrox®

1953 New synthesis of linalool 1959 cis-3-hexenol 1962 Methyl dihydro-jasmonate1970 Damascones alpha and beta Damascenones alpha and beta Development of

NMR spectroscopy

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A Brief Historyof Fragrances

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Juniper Berries

Frankincense

Calmus

Cinnamon

Myrrh

Galangal

Early Raw Materials

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Huang-ti Nei-ching2674 BC

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Egyptian Pharaoh Khufu

Great Pyramid (2700 BC)

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Ebers Papyrus (1550 BC) - Medical papyri of ancient Egypt purchased by Georg Ebers in 1873-1874

For asthma - mix of herbs heated on a brick so the fumes could be inhaled

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Ebers Papyrus (1550 BC)

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Temple of Edfu (237 BC - 57 BC)

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Ancient Perfume RecipeTemple of Edfu

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Frankincense Myrrh

1st Century AD, Romans used 3000 tonnes frankincense and 500 tones myrrh annualy

Nero Claudis Caesar Augustus Germanicus (37-68), Roman Emperor

$100,000 to scent one party

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Napoleone di Buonaparte (1769 -1821)Emperor of France

2 quarts of violet Cologne each week

60 bottles of jasmine extract per month

Jean-Francois Houbigant appointed personal perfumer to Napoleon and

Empress Josephine

1912 - Quelques Fleurs

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Ernest Beaux (1881-1961)

Bouquet de Napoléon, A. Rallet & Co.Moscow, 1912

Admired Houbigant, and was known for mixing large quantitiesof aldehydes with florals (rose, jasmine)

Napoleonic Wars - Invasion of Russia (1812)

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Le Bouquet de Catherine, honoring Catherine the Great (of Germany)

Empress of Russia (1762-1794)

After Russian German war of 1914 (WWI 1914-1919), anti-German

sentiment was fierce

Le Bouquet de Catherine renamed Rallet

No1

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(1920) Gabrielle “Coco” Chanel + Grand Duke Dimitri Pavlovitch

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(1920) Gabrielle “Coco” Chanel + Grand Duke Dimitri Pavlovitch

U.S. launch in 1950’s

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Top note: Aldehydes, Bergamot Lemon, Neroli

Middle note: Jasmine, Lily of the Valley, Orris

Bottom Note: Vetiver, Sandal, Vanilla, Amber

$260 / 1 oz bottle

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1892 Allyl-sulfide identified in garlic1900 Saccharin first used as a sweetener1912 Maillard reaction first described1926 Furfuryl mercaptan identified in coffee1931 Amadori products recognized in the Maillard reaction1933 Structural determination of jasmone Jasmone1934 Synthesis of muscone 1937 Sweetener cyclamate discovered1946 Perfection of Wallach’s isoprene rule for terpenoids 1947 Structural determination of irone 1949 Ambrox®

1953 New synthesis of linalool 1959 cis-3-hexenol 1962 Methyl dihydro-jasmonate1970 Damascones alpha and beta Damascenones alpha and beta

Cyclamate banned in the USA1981 Aspartame gains FDA approval1982 Grapefruit mercaptan identified1998 Sucralose approved by the FDA

Flavor Chemistry

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1960 Ready-salted cheese and onion Bag of ready-salted and a bottle of red pop

1970 Salt and vinegar

1980 Smoky baconRoast chickenRoast ox

1990 Roast beef and mustard

2000 Sea salt and balsamic vinegar Salsa and mesquite

Pack of Montery Jack kettle chips and a mango and passionfruit smoothie

The Potato Chip

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Recent LiteratureJournal of Agricultural and Food Chemistry

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The Flavors and

Fragrances

Industry

$20.5 billion industry

The Big Producers(Givaudan, Firmenich, IFF)

43.7 % of the market

Total

Others

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The Flavors and

Fragrances

Industry

$20.5 billion industry

Total

Others

The Consumers

food groups: Kerry, Danisco, Kraft, Nestleconsumer goods: P&G, Unilever, L’Oreal

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Global Market for Flavors 2006(US$ Million)

The Flavors and

Fragrances

Industry

Global Market for F&F 2006

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The Flavors and

Fragrances

Industry

Global Market for F&F 2006

Global Market for Fragrances 2006(US$ Million)

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A Note on Regulations

Fragrances: Raw materials and finished products

Geneva-based International Fragrance Association (IFRA)

US-founded Research Institute for Fragrance Materials (RIFM)

testing and monitoring of fragrance materials

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A Note on Regulations

Flavors: More localized legislation (less international)

US-based Flavor and Extract Manufacturers Association (FEMA)4000 materials that are Generally Recognized As Safe (GRAS)

FEMA GRAS - may be used at ‘set levels’, and may not be listed as individual substances on ingredient list

Nature-identical syntheticsEurope: ‘contains flavoring’

US: ‘contains artificial flavoring’{

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Problems of Using Natural Flavors 1) Many natural flavor have low intensity, it should be used at a high dosage which

results in an unsatisfactory texture and poor stability. 2) Concentration of natural flavors is usually accompanied by significant changes in

the flavor profile. 3) Natural flavors exhibit variations in strength and quality. 4) The supply of natural materials is becoming uncertain. 5) Most natural flavors are unstable and undergo changes during postharvest

handling, processing or storage. 6) Many natural products contain enzyme systems which may result in decomposition

and/or the formation of off-notes. 7) The toxicity of many natural products has yet to be established.

Natural or ImitationPrice

Availability of raw material

Permissibility under current legislation (toxicity test)

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Disadvantages of Using Imitation Flavors 1) Original natural flavor is more subtle - imitation flavor sometimes

described as “chemical” 2) Difficulties in “labeling” 3) Many natural flavors have a built in reservoir of flavor precursors which can result in the generation of additional flavor imitation flavors are not. 4) Imitation flavor generally require the use of either a solvent or a carrier 5) Restriction by legislation 6) Problems with texture in the end product

Natural or Imitation


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