Jasmine, perfume products from

The famous Chanel No.5 was the first and still is the commercially most successful perfume that used synthetic fragrant chemicals in addition to those from natural sources. Coco (Gabriel) Chanel asked her perfumer Ernst Beaux to produce several feminine perfumes. He presented to her ten products numbered, out of which Ms. Chanel picked No. 5, because 5 was her lucky number. Chanel No.5 was further popularized by Ms. Marilyn Monroe. It uses jasmine oil obtained from jasmine... 

The perfume of the Jasmine flower is principally marketed in the form of enfleurage products or similar preparations, but the oil is of the highest importance, an I its examination has led to the preparation of a synthetic jasmine oil of considerable commercial value. The jasmine perfume of commerce is almost entirely prepared from the flowers of Jasminum grandiflorum, but as there are many closely allied species the lollowing details of them are of considerable interest. 

Jasmine. Jasmine is one of the most precious florals used ia perfumery. The concrete of jasmine is produced by hydrocarbon extraction of flowers from Jasminum officinale (var. GrandijJorum). The concrete is then converted to absolute by alcohoHc extraction. It is produced ia many countries, the most important of which is India, followed by Egypt. Jasmine products are rather expensive and are produced ia relatively small amounts compared with other materials. However, jasmine is particularly important ia perfume creation for its great power and aesthetic quaUties. Eour of the principal odor contributors to jasmine are OT-jasmone [488-10-8] (14), methyl jasmonate [91905-974-] (15), benzyl acetate [140-11 ], and iudole [120-72-9] (16). 

The examples of the cis-trans-isomerizoXion are the photoreaction of a-ionone 1 and jasmone 2 as shown in Scheme 6. a-Ionone has a fresh violet-like odor and a warm-woody balsamic-floral odor of deep sweetness and moderate tenacity. It is used widely in all types of perfume compositions (Shibamoto and Mihara, 1983). cz5-a-Ionone is yielded from trans-a-ionone by photo irradiation (Buchi and Yang, 1955). Jasmone, which has a jasmine-like odor, is the principal aroma component in jasmine oil (Nofal et al. 1982 Toda et aL, 1983). On irradiation, jasmone gives the final products trans- and cis-2- 2 -ethylcyclopropyl)-3-methyl-2-cyclopenten-l-one (Tateba and Mihara, 1986). These two products are described as having a waxy, oily, and cz -jasmone-like odor for trans-form and a cz -jasmone-like odor with a mild, minty, and woody undertone for cz5--form. 

It is easier and cheaper to synthesize benzyl acetate rather than extract it from jasmine. Most perfumes use synthetic benzyl acetate, but the compound is identical to the natural product. 

The perfume industry makes considerable use of naturally occurring substances such as those obtained from rose and jasmine extracts. In many cases, the quantities of fragrant oils available by natural product isolation are so small that it is necessary to synthesize them. Examples are the olfactory components of violets, which include fro s-2-cis-6-nonadien-l-ol and the corresponding aldehyde. An intermediate in their large-scale synthesis is cis-3-hexen- l-ol, whose industrial preparation is described as a closely guarded secret. Using the methods in this and the preceding sections, propose a synthesis from 1-butyne. 

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