Jasmine fragrance

The cycloaddition between 25 and 26 is a crucial step for the synthesis of methyl cA-dihydrojasmonate, a key constituent of the commercial jasmine fragrance Hedione 27. 

Ketones are most widely represented and include cyclopentanone derivatives, such as the jasmin fragrance substances, and cyclic ketones with 15-17-membered carbon rings, such as muscone and civetone, which are constituents of the extremely expensive animal products, musk and civet. Cyclopentadecanone, a natural musk fragrance, and the unsaturated 5-cyclohexadecen-l-one, which has not yet been found in nature, have odor characteristics similar to those of muscone and civetone and are more easily synthesized. They are, therefore, often used as substitutes. 

The main volatile component of jasmin oil is benzyl acetate. However, minor components such as indole [120-72-9], cw-jasmone [488-10-8], and methyl jas-monate [1211-29-6] contribute strongly to the typical jasmin fragrance [544-549]. 

Kuhimann, H., Stetter, H. The addition of aldehydes to activated double bonds and its application in the synthesis of jasmine fragrances. Fragrance Flavor Subst, Proc. Int. Haarmann Reimer Symp., 2/ af1980, 99-110. 

C13H22O3, Mr 226.31, < ,I] 0.998-1.006, re 01.457-1.462, is a jasmine fragrance that is closely related to methyl jasmonate, which occurs in jasmine oil. Methyl dihydrojasmonate has been identified in tea. It is a liquid with a typical fruity, jasmine-like blossom odor. 

C13H22O3, Mr 226.31, 6/>8pa 85 °C, rej3° 1.4562, is a colorless liquid with a long-lasting, floral, jasmine-like odor, that has only little of the fatty aspect characteristic of many jasmine fragrances. The product has not yet been found in nature. 

Toxicology TSCA listed Uses Fragrance in cosmetics, jasmine fragrances, beauty care, soaps, laundry care, household prods. flavoring agent... 

PHENYLACETIC AGIO Very important fragrance chemical. Only recently was it banned by the DEA. Fragrance companies still can t believe they cannot openly sell it. It makes up 15% of jasmine oil (very expensive). 

A commercially important outlet in the fragrance industry is the methyl dihydrojasmonate [24851-98-7] (26) which is made by Michael addition of a malonate to 2-pentyl-2-cyclopenten-l-one [91791 -21 -8] (52) and which is used in perfumery for blossom fragrances, particularly jasmine (see Perfumes). 

As early as 1967, IFF chemists (11), in an in-depth study of jasmin absolute, identified an ultratrace amount of one of the key compounds in the entire fragrance repoitoire, hydroxycitroneUal [107-75-7] (21). This chemical has been used for many years in almost every "white flower" fragrance to give a very diffusive and lasting lily-of-the-valley and jasmin note, but this represents the only known identification of the compound in nature. This illustrates that the human nose can often predict the presence of a molecule well before the instmmentation becomes sufficiently sensitive to detect it. 

Famesol is manufactured from nerohdol by isomerization over a vanadium catalyst (55). Famesol occurs in several essential oils, such as ambrette seed, neroh, rose, cyclamen, and jasmine it is also used in floral and oriental fragrances. 

Uses. Cinnamyl alcohol and its esters, especially cinnamyl acetate, are widely employed in perfumery because of their excellent sensory and fixative properties. They are frequently used in blossom compositions such as lilac, jasmine, lily of the valley, hyacinth, and gardenia to impart balsamic and oriental notes to the fragrance. In addition, they ate utilized as modifiers in berry, nut, and spice flavor systems. The value of cinnamyl alcohol has also been mentioned in a variety of appHcations which include the production of photosensitive polymers (49), the creation of inks for multicolor printing (50), the formulation of animal repellent compositions (51), and the development of effective insect attractants (52). 

A fragrance company in Japan conducted tests in an attempt to determine the effects of smell on people. They pumped different fragrances into an area where a number of keyboard entry operators were stationed and monitored the frequency of mistakes the workers made. The results showed that pleasant odors like jasmine and lavender were associated with significant reductions in errors. 

Dihydrojasmone is used in perfumery in jasmin bases and, more generally, in blossomy and fruity fragrances. 

Methyl jasmonate is used in fine fragrances where it provides rich soft effects in jasmin and muguet compositions. 

Methyl dihydrojasmonate is used in perfumery for blossom fragrances, particularly in jasmin types. 

Raw materials derived from intensive agricultural cultivation are usually relatively inexpensive. However, the prices of some natural materials may exceed 1000 per kilogram because cultivation and harvesting of these plants are tedious and product yields are very low. Examples of extremely valuable ingredients of fragrance and flavor creations include rose oil, jasmine absolute, tuberose absolute, orris root oil, ambrette seed oil, angelica root oil, and orange flower oil [220]. 

Annual worldwide production of jasmin concrete is ca. 101. The absolute is one of the most valuable blossom fragrances used in fine fragrances. FCT 1976 (14) p.331 [8022-96-6], [84776-64-7]. 

In plants the 13-hydroperoxide produced from linolenic acid by lipoxygenase (Sect. 23.4.1.2) can be converted to the allene oxide by allene oxide synthase followed by cyclisation, reduction and -oxidation to form jasmonic acid, an important plant growth factor the corresponding methyl jasmonate is a valuable flavour and fragrance compound that imparts a sweet-floral, jasmine-like note... 

Benzyl alcohol (1) occurs widely in essential oils both as the free alcohol, and, more importandy from a fragrance standpoint, in the form of various esters. Although benzyl alcohol itself is rather bland in odor, combined with its much more fragrant esters it is an important part of the odor of jasmine, ylang-ylang, gardenia, some rose varieties, narcissus and peony, as well as castoreum, balsams of peru and tolu, and propolis. Benzyl alcohol occurs primarily in flower oils and tree exudates, whereas a large number of essential oils obtained from other parts of a wide variety of plants contain no benzyl alcohol or its esters (1). 

Distantly related plants, such as rose, jasmin, and lavender have quite independently gone down this road of complexity, based on different groups of chemical constituents. We may conclude, therefore, that complexity of odor has evolved as being the most effective way of evoking a desired response from an animal with the ability to smell and the ability to memorize odor. What is remarkable is that the particular combinations of materials that individual flowers produce to make up their fragrance have, to our own sense of smell, an identity far greater than a random mixture of as many ill-assorted chemicals. Perhaps we may infer from this, in view of the similarity of our receptor cells, that the balance of materials is as important to the olfactory mechanism of the bee as it is to our own in producing a sense of identity and aesthetic pleasure. 

Although natural flower absolutes are less important than in Chanel No. 5 and Arpege in establishing the essential character of the fragrance, rose, jasmin, and tuberose may be added, together with tonka, to back up the coumarin (1.5%), and a trace of natural vanilla. A trace also of ambrette seed can give a wonderful smoothness to the composition, working particularly well as part of the rose accord. 

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