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From Ambergris to Cetalox Laevo* Tradition, innovation and creation by Corinne Chauffat and Anthory Mortis, Frmenich ho would have imagined just a few decades ago that perfumers today would have at their disposal an amher product of entirely synthetic origin with a purity that corresponds to more than 99 percent of (-) Ambrox (5? This achievement has a long and captivating history of sciontfie discoveries and creative ingenuities, all linked to the enchanting perfume of amber, Tradition tobacco, musk, and tho smell of the ovean, In most ‘The manner in which ombergris is cases, the amber note is immediately appealing t0 formed by the sperm whale? and then the untrained nose and its scent, despite being very subsequently discovered on far away characteristi, is difficult to describe; warm, anisnal, hooabse softer havins)psen i’cransported exciting arid mysterious. by ocean currents, contributes much to Long before it played a key part in perfumery, the mystery and magie ofthis perfumery smbergris was valued for other properties. In the substance. This legendary ingredient of times of The Thousand and One Nizhts, its curative the perfumer’ pallette comes from a effects on heartaches were widely recognized: t was pathological animal reaction, which also burnt like incense for enjovment of its pleasant cannot he produced by breeding or scent, Moreover, some East-Asian dishes were spiced cultivation. The prolonged stay inthe sea with it, whereas the Chinese believed it to be one of and the combined action of oxygen and the most effective aphrndisizes solar radiation contribute to ambergris’ The first traces of ambergns’ use in perfumery go unique odor. Its complex and subtle back to the 0 Century BC. Arabs recognired its character shows facets of amber, incense, fixative effects on the evaporation of other oils. In the exotic wood, earth, camphoraceous, 14 Century AD, ambergris became one of the mest valued perfumery ingredients, along with civet and musk, Tkvas used asa tincture that needed to mature over many months, somtetianes even years, before fa, Grsambrol, Ambrinol, Fratear 404 ani Arlirow DL. are regitered trae names of Fimcach in hisetcle the wthon we the revealing ts full fragrance, The most appreciated Silvingromensare Ambo vichudestss fineiures were male up ofthe gray and most valeable Mechinw Sonpacdohsperctt ashe, pastof the ambergris, which has consequently given U'hmbonvhehingeatesticcumiiomerteor same to the precious substance. The white part has Livro. ofthe molecule called CAS Napkto2.1-b) 9 odor: the black part is not highly valued, whereas for dedealrro—,6,6,01-—tetranety thi prestcamoptia ate 2) And “hich indter the enantiomer Do Destro, the molecule calld Ga pio (2-0) ray ‘ ‘edeedncet a, 6.6.98 tetramethyl nd MNoVation which prewris at optal saiey (2) Ambion Tn the 1990s, Firmenich initiated a vast research the brown part is used in some perfumery products. Mihm sai'S| dutsticopitalcatyaod Program on the composition of ambergrs, The study facemies winch qualities whe [2) Auibeos, OF is main component, a triterpene called ambreine (3), complemented research pasformed by L “ancy 4 wan sulstanee, fs protuel by dhe Ruzicka a long-term collaborator based in Zi igestve tarts th protect rom th hy Faple— the gat 4 sperm Wile. pros © pax Stoll and his Genevachased teu also counted among the pioneers in this research. E. Lederer group joied the teantin 1947, after the results on the structural form of ambreine ‘were presented. Though ambreine counts for ust 25-45 percent of the non-volatile components of ambergris, and is odorless it was regarded as tie proba source of the yolatile components of 2 These volatiles originating from chemical degradation processes contain soine of the key elements ofits fragrance At the end of the 1940s, Stall turned away from the research on the original ambergris. aanitnal substance and initiated research on iseovery of Ambrox was just around Ue Selareolide [2], derived from selarcol, raw material. In fact, this lactone could bobtaiued throughs ambreine oxidation: ho already shared a similar bieyelic structure lleseribed hy Leceret:* The link was takin Stoll suygested a synthesis by the reductie sclareolide with LiAIH,, followed by an tion of the resalting diol [4] (¥-2) to obta '5] named Ambrox.? These findings mats point in the commercial production of tri nner products of vegetal origin, The Ans molecule as only is part of the amborgris tincture some 30 yes ated fron he chusen he inoleeules Vas Ioape of Ueyelia- the oxide atuming lie ve volatile hater, amber products derived from selareol [1]. thus confiming ils natural origin as ane ole key ‘which is fonmd in clary sage (Salcie selarea), odorous components of this precions subst ee.* ‘This alcool was known to have a light Until the 1950s, the so-called amber ness were amber odor. Stoll and his collaborators usually specialties baseel on labdamnm, eith, “in a undertook a systematic sclareol degrada processed form to give a perfume base or a blend tion to obtain all oxidation praduets with vith vanilla andor other balsamic wotes, Ar Her 205 an odor, Ariong these products. an unsuturuted alvobol and an oxide were selected, The oside indeed had an amber ‘odor and could be prepared fairly easily This observation encouraged the research: cs to continne their investigations. The (1923) and Ambrarome Synarome (1936 specialties used in fine pesfuamery in adits to amnbergrs, which contributed to the succes of many classie perlunes Shorth-after Stalls liscovery, Birmenieh unehed two specialties: Fsstenr 404 (1952), based ap proximately 10 percent of Ambros, and Gris nbrol (1954), whieh included both Ambrox aad a sarin, ‘This ambeagris component gave its naine to third W alee alma 9 ea evelopment as Ruck s. th loti dre Cryin ry Blended Formulas: eee : e feoen a Betncncnt Formation of sclare (4 Sclarecl [1] (¥) Sclareolide [2] (4) Selareolide [2] [-) Dioxylorea! [a] product erested in 1954 — Armbrinol —a mixture of a B- and isomers, These products were considered. to be important alternatives to the original animal substance, which was rare and expensive. Hixateur 404 particularly influenced perfurnery of the 1950s gnd the. 108s. as it beeame a dominant amber note in fine perfumery. together with Kephalis (Roure, 1965), Fisateur 404 was used in very small quantities beeause of its pow However inthe mid 1970s, some perfumes realized that the use of Ambroxwas not necessarily solely restricted to fine perfumery, and that it showed excellent performance in shampoos, soaps and Uetergents, Its smell, diffusion, stability, substantivity — | and tenacity made it an ingredient with outstanding SHAPE." Amnbrox was not commercialized as such until the end of tho 1970s, eoncureent with the emergence of the first competitive material Ambroxan (Henke) | ‘The manufacturing of such x product by a soap and detergent company confirmed tho importance ofits use in functional perfumery. The emergence of | Ambros-type products in turn induced an increase emand in sclaroolide from clary sage. At that time, there was only one producer worldwide and so, as | cary sage i sensitive to climatic conditions, as with and distinetive character. ATE je pon Derlomanee and aw ater (4) Ambreine [3] () Ambrox [5] KOSHER CERTIFIED | FLAVOUR & FRAGRANCE CHEMICALS. WE SPECIALIZE IN: ANISYL ACETONE GINGRONE 6-METHYL COUMARIN PARA CRESYL METHYL ETHER, PROPENYL GUAETHOL RESORCINOL DI METHYL ETHER VERATRALDEHYDE, De rr Poot meta) eee eee ea eee et | | 0 i/ Hv | i OMe 2 | a Nes, | La? oe ‘ Ester BC, (6) EB luna ost i ce e Dedanninteed There combined actor Indvousrere shore 1958 The aie tees contac th co ihe devekrrmes aun ene yet in 195 eagerto ake prt nthe George Be co of Back Sel and Lod amber adventur | the and in the early 1980s he proposed a first c£) Ambros from B-ionone.” This racemic product was different from the 9 percent of =) Ambros product derived from dlary sage. Othe groups started to he active in the sam eld, andl at this time experiments wer carvied out with Beionone, suggesting | sentheses hased specifically on th Gcelzation of homofarneste acid.” The reproduction afte amber odor from petrochemical derivatives had started snnouncing the ari Vand vegetal derived substances, al of an alternative to The kneneledlge ane Know-hiw ace nonated cventwally enabled an economically viable Drochiction of £) Ambre | tion of Cy alcohol (7) ant Ambros DL. (81 more than 30 percent of 4) Ambrn was Tanmchesl in 1959 not as Ambros but as an altermitive ariber over many years of investigation naterial contain substitute t ingredient Subsequent years were devoted to the sprovenient of the Ambros DL synthesis to obtain a purer racemic quality and eventually th 1993. after 10 years of inves the syuthetic prexl vwith the involv optically active product. In tion of the Asmbri snent af piwne reached, with the launch of Getalos. The SS 90,1121 \ Alcohal f C,(71 = RS seni ) A Y ~~ 4 /\i Ambrox DL [8] Offactive chart of Cetalox Laevo, CeCe eee Ct) fee uated i Anbe () Annbrax ] om |e tater “Catalo | cototane | Arbroxer syuthesis of this racemic product of more th 96 pereent parity sas anilestone i both ong nist. aml process technology: The lane cocess whieh required meticulous developmeit ane uptinn ation of the reaction conditions, benefited catly From eatalstie chemistry in order to achiewe -« desired quality, The next step? To mene on» reach ww optically pure quality of ai entirely syuths ic Cotalox — and so toda. with Cetalos Leave, range has been extended Creation Perfinmery intensst in the amber waterialy «tain: ing more than 99 pereent of -) Ambran der From eliry sage lod to the marketing of Xn sivanean and Sekurogam (Charabot i n to Aubreaan (inv KAO), to tucntion a fe Hows Feit that materials having the sie elier cal structure cam fave different ular muaices"1 of production ingredients nts a ehtly modife the odlor of a chaps the conditioning of the product — whether Oe eeines hana Cetalox Lacvo Cetalox ‘Ambroxan ion of the volume and diffusion of Cetalox Laevo, Cetalax, Ambrox DL, ay Amibrox OL fs) am ‘Summary of the isomeric composition of Cetalox Laevo, Cetalox, Ambrox DL, Ambrox and Ambroxan-type products Composition Origin Cetalox Laevo > 89 percent (-) Ambrox Synthetic, Cotalox > 96 porcont (2 Ambrox Synthetic Ambrox DL >SOpercent (t} Ambroxand.= 99 percent (-) Ambrox Natural erystals or as pellets — ean also make a With at least 50 percent of racemic Amb x and difference. In regards to the composition of the various materials, the (£) Ambros isomer ratio is particularly important for the odor Ambros is described as more anibery nicl as much as hwo to three times more powesfil than (+) Ambrox, which is re wood! Howeve considered although this variation exists in the odor. it should aot be forgotten that according to ‘one or the other enantiomers differently Ambros, the historical refevence metic inheritance, people sinell ie inheritance, peop contains approsimately 9 percent Ambros and various ambrols, The latter Drings elegance and olibanun nuance (© this fine amber, cound. powerful and iffusive note. Ambroxan is probably one of ne most powerful anber notes. 1s ver dlillusive, dry snd animal, with an earthy patchowll and dusty character, Cetalox ~~ Li irnilar to Amloraxan, iti diliasive, som ~v9 is & powerful aninial amber nore hat dusty, with a vetyver orvis effect Cetalon covers a broader olactive spect than the products mentioned above. 1 an amber, woody notes warm, Full and rich chanseters, Although at fist it seems less iMfhisive than Ambrot or Ambros aratively filler Getales develops into « com other diastereolsomers, Ambros DI. is prol-bly the most distinctly dissociated product in this g> up. The woody character is more pronounced thank in particular to the presence of a di s woody, cedar tere Dis described a Its warm »h note is awoaxdy, cedar vetyver, camples with a hint e lahe dana. T-1, Pot and F-5 simmarize these « varacte istics and olfactive evaluations When studying the characteristies of thi» various materials, one notes that Cetalos Luevo an rosa ate very effective in small quantities Hanks ver and diffusion, However, bey vd a certain proportion, the dry animal characte: prevail + Lean give an aggressive, dirty effect. Cetalos, on +e othe destroys the lurmoay of the eompesitic wand. ean he used in considerably larger qi tities, ind although the amber note is cleurls effes wwe, the elegance and harmony of the perfume are j eserved The series of aceords in T-2 eleurhsilhastrat this phenomenon, In A. the amber note harnion izes with the powder notes of the accord, whereas in 8, the second is unbalanced by the too-high cone: tration o Ambrowan, In Cand D. Cetaloy lifts the ful! bodied aul powdery character, despite the high cat sentra tion, giving the accord an elegant sofiness o! aracter acd bya rich amber note, Being able to us. Cetalot 1 greater quantities increases the substants ty of th Greations while preserving their original olf. ts Uifections — ah important asset for product applied tothes odor Frage ilepe cost Ack The Mint will & A T coumarin 20 percent IPG 10 © Raspberry ketone 10 percent DIPG 10 | Aabanolide £0 percent DIPS 10 © Ambroxan 5 percent DIPG a2 | GotaloxS percent DIPS 3 ‘The ontcome of the Ambrox story is certainly not amystery; the synthetic reproduction of a natural calor is a direction that is well entrenched in the fragrance industry. The goal, of course, is to equal, or ‘even qualitatively improve upon, nature without depending on it, thus allowing mankind to offer essential perfumery products with an ever-improved cost/performance ratio, Acknowledgments ‘The authors wish to th Mimoun, Roger Snowden, Chri Willian k Cyril Mahaim, Hubert jan Vial and Alvin ress comrespondence to Covinne Chanflat, Fizmenich $4, A-T211, Genesa 8, Seitzerand: corine chanflit@rmenich com Aaferencos LH Janystn, Por. Kosmet 30,53. 60(1902 2. E. Lederer F. Marks, D. Mercer and C. Poni, Hely. ‘Ato 29, 1354-1955 946) 3. be Ruricha amd MM. Jat, Hels. Chim, Acta, 14, 645 (1930. 4. Leskerer and D. Mercer, Espen 3,188 (198 5. a) CHL-Pateat N° 298509, and I. Hinder, Helv Chim. Acta 38,125 5.1950, M. 308 (1950 Pinova, a divi performance food-grade rosin and terpene products and di ‘Some of our product lines: Rosin, modified rosin, rosin esters yroganated rosin devatives 6 8 c D 19 10 19 10 10 10 10 10 19 05 : Z 20 30 B.D. Mockesee and RR. Patel, Proceed. 7 Gong Fat. Oe Kyat pan paper 196 39 AXKMornis, What sluence do new fragrance ‘mutrils hase in perme? erful. 24 os ALP. Morais, Natural Synthetics, erkum, Flavor 913) 968, Firmenich $A, EP 170655, 1956 (Chem_ abst 1986, 105, 209257). Buch and H, Wiest, He! Chim, Acta, 72,996 (1389 Coneortinm file olecktrechemische Industri Gorbit, DE 9240054, 1964 (Chem. Abt, 198 101, 136925) Masog, JP 90229451, 1985( chem Abstr 1986, 104, 168353); Karary, JP 02255773. 1980 (Chem. Abstr 160], 114, 18747), ©. Licius, Chom. Bor, 98, 2563 (1050), Kawnobe,K, Kopendand M, Matsui, Agi. Bil (Chere 1475 (1956), apd references cited terete, Fimnensh SA, EP 403945, 1890 (Chem, Abst 19st. 114. 347117}: RIL. Snowlen, JC Eincheoborger §.M. Linder, P-Sennay, Vsland KN. Sctule-Bke, J. Org. Chem, 87,955 (1992) Firmenich SA WO 9612504, 195 (Chet, Abstr 1996, 135 istry. Fat. ET er (189) 535, The Fascination al. Perspectives, Do dens tn. 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