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Fragrance Chemistry Š Milestones and Perspectives

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Fragrance Chemistry Š Milestones and Perspectives FLAVOURS AND FRAGRANCES 379 CHIMIA 2001,55, No, 5 Chimia 55 (2001) 379-387 © Schweizerische Chemische Gesellschaft ISSN 0009-4293 Fragrance Chemistry - Milestones and Perspectives Markus Gautschi*, Jerzy A. Bajgrowicz, and Philip Kraft Abstract: This mini-review on Fragrance Chemistry focuses on milestones in the timelines of musk, ionone/ woody and sandalwood odorants, as well as on new perspectives arising from the development of fragrance precursors. After a brief introduction of the history of perfumery, its mutual interaction with the chemistry of odorants, and the current state of the fragrance industry, the whole spectrum of musk odorants is discussed from the accidental discovery of nitro musks like Musk Ketone® via the parallel evolution of benzenoid and macrocyclic musks, to new structures like Cyclomusk® and Moxalone®. Following a description of the structure elucidation of violet odorants, ionone and irone,lso ESuper®and the structurally related Georgywood®, but also Koavone® and Timberol® are treated. Weissenborn's discovery of terpenylcyclohexanols lead to sandalwood synthetics that today are mainly derivatives of campholenic aldehyde like Sandalore®, Sandal Mysore Core®, Polysantol®, Ebanol®, and Javanol®. Finally, lipase labile precursor systems, for instance digeranyl succinate, or UV-radiation labile ones like citronellyl coumarate and citronellyl cyclohexylglyoxylate are presented, and views on 'secondary benefits', 'anti-perfumes' and exclusive 'Editions de Parfums' conclude this overview on the driving forces and the serendipities in the chemistry of fragrant substances. Keywords: Fragrance precursors· lonones . Musks· Odorants· Sandalwood 'Sailing on the scent o{your perfume 'through smoke' - per fumum - the treas- perfumes. Vanillin blended with resins, Only memories to guide ures of nature to please the Gods [2]. Al- animalic notes and a floral accord with Distant thoughts inside ... ' coholic extracts of plants and resins as hesperidic elements, was the basis of G. Duke, 'Illusions' [1] well as composites thereof were used in 'Shalimar' created by Jacques Guerlain the middle age as both perfume and med- in 1919, the prime example of an oriental icine (aqua mirabilis), aphrodisiac and fragrance. And in 'Chypre' (19]7), 1. Introduction elixir oflife (aqua vitae). After Napoleon which gave the name to the third big fra- Bonaparte had ordained by decree in grance family, Franc;:ois Coty already From the fresh, sparkling shower gel in 1810 that manufacturers and vendors had used the newly available quinolines, es- the morning to the sensual, seductive per- to make a distinction between pharma- pecially iso-butyl and iso-propyl quino- fumes that surround us during a romantic ceuticals and perfumes, eaux de Co- line, though leathery Chypre fragrances candle-light dinner, we experience fra- lognes were no longer drunk. The newly like 'Bandit' (Piguet, 1944) became fash- grances at almost any time and almost defined 'perfumes', still composed ex- ionable only much later. everywhere. Even our shopping is ac- clusively of natural ingredients, mainly With the beginning of the age of fash- companied by pleasant scents, and when essential oils, became more and more so- ion, the creativity of both designers and we reach out for personal and homecare phisticated, and consequently luxury perfumers gave another boost to a rapidly products we very often have the choice items for monarchs and their entourage, growing industry. After World War II, between different fragrance variants of aristocrats and patricians. The use of syn- the rise of the consumer purchasing the same brand. thetic ingredients marked the beginning power finally made perfumes available to The use of perfumes has a long his- of modern perfumery at the end of the everybody and led the way for their intro- tory: In biblical times people sacrificed 19th century, and enriched the perfumers duction into many functional products. palette with new odor notes. Today, perfume is an everyday item, In 1882, Paul Parquet created 'Fou- even sold in supermarkets, and people in gere Royale' around an accord composed genera] possess more than just one fra- of coumarin, oakmoss, geranium and grance. Whereas 50 years ago a perfume 'Correspondence: Dr. M. Gautschi bergamot, and with its launch by Hou- was still considered a precious item, and Givaudan Dubendorf AG Fragrance Research bigant the new era commenced. In the women would use the same fragrance Oberlandstrasse 138 following years, major achievements in over many years (while men's fragrances CH-8600 DObendorf the synthesis of fragrant compounds as were barely accepted that time), today Tel.: +41 1 8242324 Fax: +41 1 8242926 well as the discovery of new odorants men and women choose which fragrance E-Mail: [email protected] catalyzed the creation of many landmark to wear according to their daily mood. FLAVOURS AND FRAGRANCES 380 CHIMIA2001, 55, No.5 Behind the scenes, the Flavor and ated with a commercial firm, the 'Societe Naef & Co. (today Firmenich), elucidat- Fragrance (F&F) industry is striving des produits chimiques de Thann et de ed its structure [11] - and overturned constantly to lower prices and to increase Mulhouse', and pursued his studies on Baeyer's theory of strain in multimem- quality and performance of perfumery in- nitro arenes systematically. In 1894, he bered rings [12]. Ruzicka and M. Naef & gredients, i.e. to make them more stable discovered and developed Musk Ketone Co. were originally aiming at an industri- and last longer. The fragrance industry, (1), which was prepared by nitrating al synthesis of muscone (2), which, with situated in between the petrochemical acetylated tert-butyl-m-xylene [9]. Musk an odor threshold of 4.5 ngll, was not and the pharmaceutical industry, has Ketone, possessing an excellent odor even extremely powerful. However, their been growing over the last hundred years threshold of 0.1 ngll, is considered to re- cyclization method employing thorium to an estimated market size of 7000 Mio semble the natural Tonkin musk closer salts [13] did not tolerate the ~-methyl CHF. While the production scale of fra- than any other nitro musk, and until re- substituent, and thus cyclopentadecan- grance compounds is closer to that of cently was amongst the most used per- one, under the name of Exaltone®, was pharmaceuticals, the product prices are fumery ingredients. introduced instead - at the exorbitant closer to those of the bulk-chemical in- Tonkin musk is the dried solidified se- price of 50000 CHFlkg [14], while Musk dustry. Some ingredients, namely those cretion (musk grains) from a preputial Ketone (1) cost less than 100 CHF/kg at with an extremely low odor threshold, follicle of the male musk deer (Moschus that time! are produced in kilogram quantities only. moschiferus L.), which inhabits the Considering the prices of the nitro At the other end, some perfumery Himalayas from Afghanistan to China. musks, it was more than reckless from a ingredients, mainly for use in detergents Its odoriferous principle, (- )-(3R)-mus- commercial point of view to subject Ex- and homecare products, are produced in cone (2), was isolated by Heinrich Wal- altone®, which was produced in just quantities of up to 10000 t/a, e.g. linalool baum of Schimmel & Co. in 1906 [10], about 6% yield from thapsic acid and had (8000-10000 t/a), 2-phenylethanol and makes up only 0.5-2% of the musk to be purified via its semicarbazone, to a (7000-9000 t/a), benzyl acetate (7000- grains. He was able to establish its mo- Baeyer-Villiger oxidation. The resulting 9000 t/a), Galaxolide® (7000-8000 t/a), lecular formula, and show that it was a 15-pentadecanolide (3) possessed, how- Lilial (5000-6000 t/a), Hedione® (4000- ketone, but it was only 20 years later that ever, superior olfactory characteristics, 5000 t/a) and Iso E Super® (2500-3000 t/ Leopold Ruzicka, in the laboratory of M. and was also introduced into perfumery year), cf also [3]. In the following, we want to point the reader to some selected milestones of the most important odor notes and to give an 5 idea of how Fragrance Chemistry devel- Galaxolide oped, what driving forces were active, (1965) 0.9 ng/l and which future direction the industry might take. A general overview on the developments of the F&F industry from the end of 1945-1994 was given by Paul 3 Z. Bedoukian in his annual reviews [4], 15-penta- o while processes and compounds of gen- decanolide eral technical and industrial relevance 1 (1927) 2.1 ng/l 7 were summarized in a more recent re- Musk Ketone Moxalone view [5]. Information on the newest (1894) 0.1 ng/l (1983) 1.0 ng/l trends and highlights in the chemistry of odorants can be found in [6], and details .. on the production and uses of individual I! I· I I I! 0 0 0 0 0 0' 0 0 C) 8 <0 .... lil substances are treated in [7]. c;; d'i "':C) , al §~ ~ ~ ~'" ~'"' ~ -: ~ ~ ~ ~ ",' , , , , 2. Timelines of Odor Notes 2 4 8 (-)-(3R}-muscone Phantolide Nirvanolide 2.1. Musks (1926) 4.5 ng/l (1952) 6.7 ng/l (2001) 0.1 ng/l As for many other disciplines, seren- dipity is also a key factor in Fragrance Chemistry, and the fortunate finding of the aromatic nitro musks by Albert Baur in 1888 marks the origin of the timeline of musk odorants (Fig. 1). Baur was actu- o ally searching for new explosives when he noticed that the product of the Friedel- Crafts reaction of trinitrotoluene (TNT) 6 with tert-butyl halides emanated a pleas- Cyclomusk ant musky smell. 2-tert-Butyl-4-methyl- (1975) 4.5 ng/l 1,3,5-trinitrobenzene was an immediate commercial success and became known as 'Musk Baur' [8]. Baur became associ- Fig. 1. The musk timeline FLAVOURS AND FRAGRANCES 381 CHIMIA 2001,55, No.5 in 1927.
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