Perfumes musk ambrette

Our next example emphasises one aspect of guideline 1. Some functional groups are so deactivating that it is difficult to do any further chemistry once they have been inserted. In other contexts it may be that they are so unstable that we would not wish to risk any further reactions. Musk ambrette 6 is a synthetic musk, essential in perfumes to enhance and retain the fragrance. It has five substituents round a benzene ring. Two of these, the nitro groups, are so deactivating that we want to add them last. So we disconnect them first. 

Cosmetic products that are photoallergenic include fragrances, such as musk ambrette and 6-methylcoumarin, and sunscreens (e.g., para-aminobenzoic acid and its derivatives, benzophenones, dibenzoylmethanes).17 Oil of bergamot, previously a popular ingredient in fragrances, has now been eliminated from most perfumes due to its phototoxic properties.24... 

The base note also contains the important accord between methyl ionone (10%), vetiveryl acetate, sandalwood, musk ketone, and originally musk ambrette. These materials together with the carnation make up the immediately recognizable central character of the perfume. 

Musk ambrette, a perfume ingredient (from compounds with 7 carbons or fewer)... 

Pure meto-cresol has been used for manufacture of synthetic musk— musk ambrette, used as a fixative to perfumes, for manufacture of synthetic Thymol and Menthol amd also leather preservative p-chloro-meto-cresol, synthetic pyre-throids, and lastly for manufacture of 2,3,6-trimethylphe-nol—an intermediate for vitamin E. o-Cresol has been used for manufacture of Coumarin and some derivatives which are employed in perfumery as fixative. o-Cresol has also been used for making Novolac and epoxy resins and also for the herbicides based on di-nitro-oAt/io-cresol, etc. In sum, individual cresols have been very successfully converted to important intermediates in the organic chemical synthesis. It is expected that further development work will lead to synthesis of many more organic chemicals of vital importance. While new chemicals using individual cresols are in the pipeline... 

Musk ambrette (4), a synthetic musk, essential in perfumes to enhance and retain the odour, is an aromatic compound with five substituents on the benzene ring. The nitro groups are by far the most electron-withdrawing so we can disconnect them first. 

Following is a structural formula for musk ambrette, a synthetic musk used in perfumes to enhance and retain fragrance (See Examples 9.7, 9.9)... 

Fisher AA, Dooms-Goossens A (1976) The effect of perfume ageing on the allergenicity of individual perfume ingredients. Contact Dermatitis 2 155-159 Fisher AA (1980) Perfume dermatitis. Part 1. General considerations and testing procedures. Cutis 26 458-463,477 Fisher AA (1990) Perfume dermatitis in children sensitized to balsam of Peru in topical agents. Cutis 45 21-23 Fisher AA (1995) Consort contact dermatitis due to musk ambrette. Cutis 55 199-200... 

Opdyke DLJ (1976) Inhibition of sensitization reactions induced by certain aldehydes. Fd Cosmet Toxicol 14 197-198 Panconesi E, Sertoli A, Spallanzani P, Giorgini S (1980) Balsam of Peru sensitivity from a perfumed cutting fluid in a laser factory. Contact Dermatitis 6 297-298 Parodi G, Guerrera M, Rebora A (1987) Lichenoid photocontact dermatitis to musk ambrette. Contact Dermatitis 16 136-138... 

Baur went on to synthesize even better nitromusks, notably Musk Xylene, Musk Ketone and Musk Ambrette. These and similar molecules e.g. Musk Moskene and Musk Tibetine) became widely used in the perfume industry. The famous French perfumer Ernest Beaux reportedly used over 10% nitromusks, especially Musk Ketone, in Chanel No. 5 (1921), which reports indicate is still used in No. 5 today (see p333). Musk Ambrette s additional floral note was used to advantage... 

Oil and absolute are used in sophisticated types of perfumes and in soaps, detergents, creams, and lotions maximum use level reported is 0.12% for the oil in perfumes. The oil is valued for its sweet, rich wine or brandy-like, floral, musky scent with a unique bouquet and roundness. While resembling animal-derived musk scents, ambrette seed oil lacks the fecal note sometimes found in the former (csir i) one of the most expensive essential oils. 

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