93-92-5

Description

α-Methylbenzyl acetate has an intensive green odor suggestive of gardenia with a bitter, acrid taste, interesting on dilution. May be prepared by acetylation of methyl phenyl carbinol; from benzaldehyde by reacting with magnesium methyl bromide and subsequent acetylation; from 1-bromoethylbenzene and silver acetate in acetic acid.

Chemical Properties

α-Methylbenzyl acetate has an intensive green odor suggestive of gardenia and a bitter, acrid taste, interesting on dilution.

Occurrence

Reported found in gardenia flower oil and avocado.

Uses

Perfumery, flavoring.

Preparation

By acetylation of methyl phenyl carbinol; from benzaldehyde by reacting with magnesium methyl bromide and subse quent acetylation; from 1-bromoethylbenzene and silver acetate in acetic acid.

Taste threshold values

Taste characteristics at 12.0 ppm: fruity, berry, green, seedy and slightly nutty.

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 1833, 1966 DOI: 10.1021/ja00960a057Synthetic Communications, 8, p. 33, 1978 DOI: 10.1080/00397917808062180

Flammability and Explosibility

Nonflammable

Metabolism

Although no published data exist on the metabolism of methylphenylcarbinyl acetate, it is likely that hydrolysis to the carbinol and acetic acid is the initial step. Williams (1959) reports studies in which 50% of a dose of (±)-methylphenylcarbinol given to rabbits was excreted as the glucuronide in the urine within 24 hr. There was some evidence of oxidation and demethylation, as mandelic and hippuric acids were found in the urine. Previously, El Masry, Smith

Consumer Uses

This substance is used in the following products: perfumes and fragrances, air care products, biocides (e.g. disinfectants, pest control products), polishes and waxes, washing & cleaning products and cosmetics and personal care products. Other release to the environment of this substance is likely to occur from: indoor use as processing aid and outdoor use as processing aid.