Jasmine

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). 

Many cycHc ketones occur in natural oils. Jasmone [488-10-8] (3-meth5l-2-(2-pentyl)-2-cyclopenten-l-one) (4) is an odoriferous component of the oil obtained from jasmine flowers. /-Menthone [14073-97-3] (5) is the most frequently occurring of four optically active isomers, and is a colorless Hquid with a minty odor obtained from Mentha species of plants. Muscone [541-91-3] (6) and civetone [542-46-1] (7) are expensive animal products. 

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). 

Odors are measured by their intensity. The threshold value of one odor to another, however, can vary greatly. Detection threshold is the minimum physical intensity necessary for detection by a subject where the person is not required to identify the stimulus, but just detect the existence of the stimulus. Accordingly, threshold deterrninations are used to evaluate the effectiveness of different treatments and to estabflsh the level of odor control necessary to make a product acceptable (8). Concentration can also produce different odors for the same matenal. For example, indole (qv) in low concentrations has the smell of jasmine and a low threshold of perception. In high concentrations, it has a strong odor of feces and CX-naphthyl amine as well as a considerably higher threshold of perception. 

Pommade. These are botanical extracts prepared by the enfleurage method wherein flower petals are placed on a layer of fat which extracts the essential oil. This method is appHed to low odored flowers, which do not yield appreciable oil on steam or water distillation, or flowers of valuable but dehcate odor (such as jasmin), which are destroyed on such treatment. Pommades, as such, are seldom used by the industry at present (ca 1995), but are further processed to provide more concentrated extracts such as absolutes. Absolutes, being alcohol-soluble, are much more convenient forms for the perfumer. 

Jasmin. "If the rose is the queen of flowers, the jasmin is the fairest and prettiest priacess. The two together reign supreme ia the world of flowers as well as ia the world of perfume" (12). As ia the case of rose, jasmin has been the subject of many iavestigations, and mote than 95 compounds have been identified to date ia extracts of Jasminum officinale L. vat. grandijlorum, the source of commercial jasmin ok, concrete, and absolute. The principal components ate shown ia Table 3 (13). 

Of the 11 compounds which constitute approximately 86% of jasmin volatiles, only benzyl acetate, i7t-jasmone (18), and methyl jasmonate possess the characteristic odor of jasmin. Trace components including i7t-j asrnin lactone [34686-71-0] (20) (0.9%) andmethyl ( /-jasmonate (6) (0.1%) are the key contributors to the jasmin odor. 

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. 

Orange Flower (Neroli) Oil. "The rose we call the queen of flowers, the jasmin the fairest and prettiest princess, but the orange flower is the most fragile and dainty of out royal family of flowers. If the rose stirs our memories, the jasmin our hopes, the orange flower stirs sentiments—sentiments most romantic " (14). Commercial neroh oil [8016-38 J is obtained by steam distillation of the freshly picked blossoms of the bitter orange Citrus aurantium L. subspecies amara, which is cultivated in Mediterranean countries as well as in Haiti and several other tropical countries. More than 125 components have been identified in the oil the principal ones are shown in Table 4 and Figure 1. 

Orienta.lFa.mily. In these perfumes, a mossy, woody, and spicy accord combines with the sweetness of vanilla or balsam and is accented with animal notes such as amber, civet, and musk. The most important floral accords used are rose and jasmine. 

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). 

Orange Flower. Extraction of freshly picked flowers of the bitter orange tree, dims aurantium (subspecies amard) for the production of concrete is carried out mainly ia Morocco and Tunisia. Most of this material is processed further to give orange flower absolute, one of the most important absolutes used ia perfumes after rose and jasmine. It is highly valued ia perfumery, even when used at low levels, for its long-lasting, rich, warm, yet dehcate and fresh floralcy. The material is a complex mixture, to which methyl anthranilate [134-20-3] linalool (3), methyl jasmonate (15), and iadole (16) are important odor contributors. 

In an important next step, it has been found that flowers and other plant parts can be analyzed by using head space techniques without removing them from the living plant (3). It was immediately observed that there are remarkable differences in the volatile compositions observed from Hve and picked flowers. This is exemplified for jasmine flowers in Table 3. Reconstitutions produced from this information have provided perfumers with novel and fresh notes for use in their creations. This technique continues to be appHed to many kinds and varieties of flowers, leaves (herbs, spices), and fmits. The reasons for the remarkable differences observed are not known. 

Table 3. Head Space Constituents of Jasmine Flowers...

Minor Varieties. Brick teas are prepared in the former Soviet Union and in parts of the People s RepubHc of China (82). These products are often cooked as a soup with butter or other fats. Flavorants such as jasmine flowers maybe added during processing. Oil of bergamot is used to prepare Ead Grey tea. 

Nerolidol and Farnesol. The alcohols nerohdol [7212-44-4] (96) and famesol [4602-84-0] (97) are isomeric and are both important perfumery products. Nerohdol has been isolated from neroH oil, jasmine, citroneUa oil, and pepper oil. It has a mild and woody-floral, slightly green odor with excellent tenacity and good blending and fixative properties (190). 

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