What it is
Benzyl acetate is an organic ester with the molecular formula CH₃C(O)OCH₂C₆H₅. It belongs to the family of benzyloxycarbonyls, organic compounds containing a carbonyl group substituted with a benzyloxyl group. It is both an acetate ester and a benzyl ester.
Occurrence
Benzyl acetate is a constituent of jasmine and of the essential oils of ylang-ylang and neroli. It occurs in apple, cherry, guava fruit and peel, plum and quince. It is also found in alcoholic beverages. Benzyl acetate was identified as a volatile component of roasted filberts and in the juice of Japanese Kogyoku apples. Benzyl acetate makes up 23.7% of the composition reported for Jasminum grandiflorum, followed by benzyl benzoate at 20.7%. The same jasmine species contains phytol at 10.9%, linalool at 8.2%, isophytol at 5.5%, geranyl linalool at 3.0%, methyl linoleate at 2.8% and eugenol at 2.5%. These components together contribute to the jasmine fragrance of the species. Benzyl acetate is a main constituent of several flower oils and absolutes, among them ylang-ylang, cananga, neroli, jasmine, hyacinth, gardenia and tuberose. It has also been reported in wine grape, white wine, tea, cooked rice, Bourbon vanilla, naranjila fruit and Chinese cabbage. It has also been reported in Mandragora autumnalis and in Streptomyces.
Properties and behaviour
Benzyl acetate is practically insoluble in water and miscible with alcohol and ether. With an activated sludge seed and an initial concentration of 100 mg/l, it reached 92 to 96% of its theoretical BOD over 4 weeks. Its estimated bioconcentration factor is 18, which suggests that bioconcentration in aquatic organisms is low. In air, vapor-phase benzyl acetate is degraded by reaction with photochemically-produced hydroxyl radicals, with an estimated half-life of about 2.5 days.
Identity and classification
Benzyl acetate has the PubChem compound number 8785. Its SMILES string is CC(=O)OCC1=CC=CC=C1. It has a role as a metabolite.
Physical properties
Its vapour is about 5.1 times as dense as air. It is soluble in benzene, chloroform, ethanol, ethyl ether and acetone, and it is also soluble in oils. Its autoignition temperature is about 460 °C. Its taste is bitter and pungent. When heated to decomposition it emits irritating fumes.
Environmental fate
Benzyl acetate is expected to exist solely as a vapor in the ambient atmosphere. In water, its reaction with peroxy radicals has a rate constant of 2.3 L/mol s at 30 °C, which corresponds to an estimated half-life of 9.6 years at an aqueous peroxy radical concentration of 1 × 10⁻⁹ mol/l.
Industrial manufacture
Commercial benzyl acetate has been prepared synthetically from benzyl chloride, acetic acid and triethylamine. In one industrial process, benzyl chloride made by chlorinating toluene is hydrolysed with alkali, and the benzyl alcohol formed is then esterified with acetic acid. This route has several stages and forms a large amount of a salt by-product.
Metabolism
In man, benzyl acetate is hydrolysed to benzyl alcohol and acetate, and the benzyl part is oxidised to benzoic acid and excreted as hippuric acid.
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