Fragrances ambergris

When allylic compounds are treated with Pd(0) catalyst in the absence of any nucleophile, 1,4-elimination is a sole reaction path, as shown by 492, and conjugated dienes are formed as a mixture of E and Z isomers[329]. From terminal allylic compounds, terminal conjugated dienes are formed. The reaction has been applied to the syntheses of a pheromone, 12-acetoxy-1,3-dode-cadiene (493)[330], ambergris fragrance[331], and aklavinone[332]. Selective elimination of the acetate of the cyanohydrin 494 derived from 2-nonenal is a key reaction for the formation of the 1,3-diene unit in pellitorine (495)[333], Facile aromatization occurs by bis-elimination of the l,4-diacetoxy-2-cyclohex-ene 496[334],... 

P., Bughbauer, G., Tropsha, A. Combinatorial QSAR of ambergris fragrance compounds./. Chem. Inf. Comput. Sci. 2004, 44, 582-595. 

Sclareol is used as a starting material for a number of ambergris fragrances. Major cultivation areas for S. sclarea L. are Russia, the Mediterranean countries, and the United States. 

Ambergris oxide (Ambrox ) is one of the most important ambergris fragrance compounds and is a key compound of ambra, a secretion product of the... 

Ohloff G, Vial C, Wolf HR, Job K, Jegou E, Polonsky J, Lederer E.. Stereochemistry—odor relationships in enantiomeric ambergris fragrances. Helv. Chim. Acta. 1980 63 1932-1946. 

Kovatcheva A, Golbraikh A, Oloff S, Xiao YD, Zheng W, Wolschann P, et al. A combinatorial QSAR of Ambergris fragrance compounds. J Chem Inf Comput Sci 2004 44 582-95. 

Kovatcheva, A., Golbraikh, A., Oloff, S., Xiao, Y.D., Zheng, W., Wolschann, P. et ai. (2004) A combinatorial QSAR of ambergris fragrance compounds. Journal of Chemical Information and Computer Sciences, 44, 582-595. 

Some L. have been reported to have cytotoxic, fungicidal, and antiviral activities. Sclareol, for example, is used in the perfume industry for the synthetic production of ambergris fragrances such as ambrox. 

Ohloff, G., C. Vital, H.R. Wolf, K. Job, E. Jfecou, J. Polonsky, and E. Lederer Stereochemistry-Odor Relationship in Enantiomeric Ambergris Fragrances. Helv. Chim. Acta 63, 1932-1946 (1980). 

The fragrance (-)-Ambrox (a commercial substitute for ambergris from the blue sperm whale) was made by oxidation of (-)-sclareol (1) with RuClj/aq. Na(IO )/ CC1 -CH3CN/40°C a mixture of (+)-sclareolide (2) with the (-)-acetoxy acid... 

Together, these compounds largely represent the odor of ambergris. Ambergris is applied as a 3% tincture in 90% ethanol, which is matured by standing over a period of time with occasional shaking. It was used in fine fragrances. FCT 1976 (14) p. 675. 

G. Ohloff, The Fragrance of Ambergris. In Fragrance Chemistry The Science of the Sense of Smell E. T. Theimer, Ed. Academic Press London, 1982 pp 535-573. 

Ambergris has always been very expensive and the decline in the whale population has exacerbated the situation. The price and availability of the natural material essentially preclude its use in fragrance and so, much work has been done on synthetic substitutes. The... 

Cyclic ethers used as fragrances include a number of terpenoid compounds. Some of them, such as 1,4-cineole [470-67-7] and 1,8-cineole, occur in essential oils in significant quantities. Others are only minor components examples are rose oxide, ner-ol oxide [1786-08-9], and rose furan [15186-51-3], which contribute to the specific fragrance of rose oil. Caryophyllene oxide [1139-30-6], which has a woody, slightly ambergris-like odor, can be prepared by treatment of -caryophyllene with organic peracids. a-Cedrene oxide [11000-57-0] is another wood-fragrance compound, which can be easily prepared by epoxidation of cedarwood oil hydrocarbons. 

Ambergris has always been very expensive and supply is precarious since it essentially relies on beachcombing. The decline in the whale population as a consequence of the whaling industry in the nineteenth century has exacerbated the situation. The price and availability of the natural material preclude its use in all but occasional fine fragrances and hence, much work has been done on synthetic substitutes. Obviously, the naphthofuran (8.10) has received most attention. Quite a number of total syntheses of this material have been published but the most important... 

Jeger s Ketal from Manool. Manool (8.42) is another labdane terpenoid which has found use as a precursor for fragrance ingredients with an ambergris odour. It differs from sclareol in that it has an... 

Aim, the son of Pierre-Frangois-Pascal Guerlain (1798-1864), the company s founder, created the perfume Jick in 1889, and thereby set down a milestone in the history of perfumes. - Tabac , designed for male customers, was created by Maurer Wirtz. It is said to have floral and spicy herbal fragrances, accented with tobacco, oakmoss and vanilla and rounded off with a blend of musk and ambergris. 

Ambergris is a waxy and flammable substance that is produced in the digestive system of sperm whales. Initially, it has a marine odor. With time, as it ages, it becomes sweeter, related to the fragrance of rubbing alcohol. Castoreum is the exudate from the castor sacs of the beaver. It is used in perfumes and as a food additive. 

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