Benzyl alcohol jasmine

Benzyl alcohol, C Hj. CHjOH, is the lowest member of the normal series of aromatic alcohols containing the benzene nucleus. It exists to a certain extent in the free state, but more often in the form of esters, principally of acetic, benzoic, and cinnamic acids, in a number of essential oils, such as those of jasmin, tuberose, cassie fiowers, and ylang-ylang. 

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). 

Benzyl Alcohol, NF. Ben/yl alcohol (phenylcarbinol. phenylmethanol) occurs naturally as the unesteriried form in oil of jasmine and in esters of acetic, cinnamic, and benzoic acids in gum benzoin,. storax re.sin. Peru balsam, tolu balsam, and some volatile oils. It is. soluble in water and alcohol and is a clear liquid with an aromatic odor. 

Esters are colorless, volatile liquids that often have pleasant odors. Many occur naturally in flowers and fruits. Isoamyl acetate (Fig. 7.27a) is generated in apples as they ripen and contributes to the flavor and odor of the fruit. Benzyl acetate, the ester formed from acetic acid and benzyl alcohol (see Fig. 7.27b), is a major component of oil of jasmine and is used in the preparation of perfumes. 

R = CH3, C9H10O2, Mt 150.18, fepiookPa 215 °C, 4° 1.0550, reg1 1.5232, is the main component of jasmine absolute and gardenia oils. It occurs as a minor component in a large number of other essential oils and extracts. It is a colorless liquid with a strong, fruity, jasmine odor. Benzyl acetate is prepared by esterification of benzyl alcohol with acetic anhydride (e.g., with sodium acetate as a catalyst) or by reaction of benzyl chloride with sodium acetate. In terms of volume, benzyl acetate is one of the most important fragrance and flavor chemicals. 

Being of high value, jasmine scent excited the interest of chemists at a very early stage. Between 1899 and 1904, Albert Hesse and Friedrich Muller identified more than 70 % by mass of the scented components, including the floral-scented benzyl alcohol, its acetate and benzoate esters, and the lavender perfume, linalool. The characteristic scent of jasmine, however, could not be completely explained (Fig. 3.20). 

Benzyl acetate is usually used as jasmine flavor. It is produced in industry through the add-catalyzed esterification of acetic acid and benzyl alcohol. This is a non-green low-yield route. So Huang et al. made an attempt to biosynthesize benzyl acetate via hpase-catalyzed transesterification of vinyl acetate with benzyl alcohol in water-in-[Bmim][PFg] microemulsion stabiHzed by AOT and Triton X-100. Owing to the high dispersion of lipase, large interface, removal of the byproduct, and activation of imidazole cation, a maximum yield of 94% was obtained [99] (Figure 15.29). 

Essential oils are obtained from fruits and dowers (61,62). Volatile esters of short- and medium-chain carboxylic acids or aromatic carboxylic acids with short- and medium-chain alcohols are primary constituents of essential oils, eg, ethyl acetate in wines, brandy, and in fruits such as pineapple benzyl acetate in jasmine and gardenia methyl salicylate in oils of wintergreen and sweet birch. Most of these naturally occurring esters in essential oils have pleasant odors, and either they or their synthetic counterparts are used in the confectionery, beverage, perfume, cosmetic, and soap industries (see Oils,... 

Many floral notes overlap in the types of material from which they can be made. The same eight materials—phenylethyl alcohol, hydroxycitronellal, benzyl acetate, phenylactaldehyde, citronellol, hexyl cinnamic aldehyde, terpineol, and indol—mixed together in different proportions can produce either a jasmin, a lilac, a muguet, or a hyacinth. The list also includes three materials that occur in nearly all rose compounds. If used together in a formula, bases that contain only... 

Amyl cinnamic aldehyde Other jasmin chemicals Hexyl cinnamic aldehyde Cinnamic alcohol Benzyl cinnamate... 

The middle part of the perfume is a bouquet of floral notes reduced to their simplest components. Terpineol for lilac, styrallyl acetate for gardenia, phenylethyl alcohol for rose, hydroxycitronellal (10%) for muguet, and benzyl acetate and amyl cinnamic aldehyde for jasmin. 

Benzyl Acetate, the ester obtained from bonxyl alcohol and acetic acid. This has a very strong and somewhat coarse, penetrating odour, distinctly resembling jasmine. Its specific gravity at 15 0. is 1 062-1 065 refractive index at 20" C., 1 5020 and it should contain at least 97-98 per cent, ester, calculated as benzyl acetate. 

Jasmine Jasmine is one of the most precious florals used in perfumery. The concrete of jasmine is produced by hydrocarbon extraction of flowers from Jasminum officinale (var. Grandiflorum). The concrete is then converted to absolute by alcoholic extraction, filtration, and solvent removal. It is produced in many countries, the most important of which is India, followed by Egypt. Jasmine products are rather expensive and are produced in relatively small amounts compared with other materials. However, jasmine is particularly important in perfume creation for its great power and aesthetic qualities. Four of the principal odor contributors to jasmine are cis-jasmone [488-10-8] (15), methyl jasmonate [91905-97-4] (16), benzyl acetate [140-11-4], and indole [120-72-9] (17). 

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