Methyl 4-phenylbutanoate

Description

Methyl 4-phenylbutyrate has a powerful, sweet, fruity, floral odor. Below 10 ppm, the flavor is extremely sweet and fruity. May be prepared by direct esterification of γγ-butyric acid.

Chemical properties

Methyl 4-phenylbutyrate has a powerful, sweet, fruity, floral odor. The flavor becomes extremely sweet and fruity at concentrations below 10 ppm

The Uses of Methyl 4-phenylbutanoate

Methyl 4-phenylbutanoate finds some use in flavor compositions, mainly as a modifier in Strawberry imitation, where is seems to do a better job, although perhaps not with the same power-as Methyl cinnamate and Methyl-hydrocinnamate. It is also used in trace amounts in Honey imitations and in various fruit complexes.

Definition

ChEBI: Methyl 4-phenylbutanoate is a fatty acid methyl ester.

Preparation

By direct esterification of γ-butyric acid.

Synthesis Reference(s)

Synthetic Communications, 20, p. 3131, 1990 DOI: 10.1080/00397919008051536
Tetrahedron Letters, 30, p. 219, 1989 DOI: 10.1016/S0040-4039(00)95164-5

Synthesis

Methyl 4-phenylbutyrate is synthesized by direct esterification of gamma-Phenylbutyric acid, which may be obtained from Benzoyl propionic acid by Clemmensen type reduction.