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Chemistry of Fragrance Ingredients

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Presentation on theme: "Chemistry of Fragrance Ingredients"— Presentation transcript:

1 Chemistry of Fragrance Ingredients
Dr. William L. Schreiber Chemlumina LLC Monmouth University Presented at Fairleigh Dickenson University November 7, 2006

2 To be discussed What is a perfume? History Natural Ingredients
Synthetic Ingredients Chemical Process Examples Research on New Synthetics The Science of Olfaction

3 What Are Perfumes? Mixtures that are created for use in a wide variety of applications: expensive couturier perfumes, cosmetics, personal grooming products, laundry products, household cleaning products, air fresheners, candles, etc., etc., etc.. From a palette of several thousand materials, most of which are manufactured by chemical processing methods.

4 History of Perfumes 5000 BC – Egyptian First Dynasty – earliest evidence 3000 BC – Mesopotamia: extraction pots, early apparatus 1400 BC – Book of Exodus “anointing with oils” 370 BCE – Theophrastus writings on use of oils to make fragrances longer lasting. 800 AD – Alembic distillation apparatus – Jabir ibn Hayyan 1200 AD – Essential oils produced in pharmacies 1600 AD – Quality of many natural extracts established 1860 AD – First synthetics (naturally occuring materials) 1900 AD – First non-natural synthetics (ionones, nitro-musks)

5 Alembic Distillation Appratus

6 What are Fragrance Ingredients?
Odorants, Diluents and Fixatives Naturals and Synthetics Chemicals having 6 – 18 carbon atoms (mostly), and usually one oxygenated functional group. There are also some multi-functional materials as well as a few sulfur- and nitrogen-containing chemical compound.

7 What are Fragrance Ingredients?

8 Performance in Use Volatility Stability
Function of molecular weight (how many carbons) and chemical type. Stability Function of chemical type and use condition (acidity, alkalinity, oxidizing, open, closed). Odor Threshold and dose/response Function of chemical structure (molecular shape and chemical type).

9 Natural Ingredients Mostly of vegetative origin, a few from animal secretions – largely replaced. Any part of a plant may be used: flowers, fruits, leaves, twigs, roots, wood. Synthetics have long overtaken naturals in volume of use. Naturals still very valuable and provide odor reference points for all materials.

10 Types of Naturals Concretes – extracts with solvent removed
Absolutes – concretes re-dissolved and filtered to remove waxes, etc. Essential oils – distillates, often with steam

11 Narcisse Concrete

12 Most important constituents:
Rose Most important constituents:

13 Most important constituents
Jasmine Most important constituents

14 Patchouli Most important constituents:
tricyclic sesquiterpene alcohols

15 Sandalwood Alpha Santalol: Beta Santalol:

16 First Synthetics

17 Synthesis of Vanillin

18 Synthesis of Coumarin

19 Synthesis of Ionones

20 Terpene Alcohols from -Pinene

21 Terpene Alcohols from -Pinene

22 More Products from -Pinene via Myrcene

23 Sandalwood “Molecular Engineering”
Alpha Santalol: Beta Santalol:

24 Synthetic Sandalwoods

25 Musks

26 Galaxolide Synthesis

27 Newer Musk Synthesis

28 Research and Development
Analytical Application of new gc methods (head space with spme) Use of more sensitive and better computerized instrumentation: gc-ms, nmr, ft-ir. Live flowers – above methods used to analyze odors of flowers before picking. New extraction methods for naturals: supercritical CO2

29 (often a combination of all three)
Synthetic Research Considerations: Structure – relationship to materials of known value – natural or synthetic Raw materials Process (often a combination of all three)

30 Synthetic Research Practical only for largest companies.
Hundreds of materials synthesized each year for evaluation. In-depth evaluation must include testing in fragrances and in applications. Decision to develop cannot be taken lightly.

31 Development of New Synthetics
Processes must be very well worked out in laboratory, pilot plant and factory. Best economics, safety and workplace hygiene. Testing is required to meet industry safety standards and international PMN requirements for all new chemicals. Cost to register new ingredients worldwide is well over $300,000.

32 How We Smell

33 Smell and Taste are Chemical Senses
In order to perceive smells or tastes, chemical substances must contact receptors in the nose or on the tongue. Perception is the result of the processing of signals from these receptors by the brain.

34 Recent Developments 1991 – Richard Axel and Linda Buck discover a family of genes that appear to be responsible for olfactory receptors. (received Nobel Prize – 2005) 1998 – Stuart Firestein expresses a receptor from one of those genes and shows it responds to different odorants. 2000 – Linda Buck shows that odor perception is based on combinatorial interaction of odorants with receptors.

35 Combinatorial Odor Perception
We have ~350 active odor receptors. One odorant activates multiple receptors. Each receptor binds multiple odorants. Perception of different odors results from distinct combinations of activated receptors. L. Buck, et. al., Cell, 1999.

36 A Code in the Nose

37 Combinatorial Detection
Receptors …. A           B           C           D           E           F           Odorants 350 Receptors: = 2.3X10105 Combinations  = Unactivated  = Activated

38 In Conclusion… Fragrance ingredients are a complex part of a the even more complex world of perfumes. Understanding what they are, where they come from and what they do is the key to making better smelling and better performing fragrances. Thank you for the opportunity to participate in your class this evening.

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