Isobutyl butyrate

Description

Isobutyl butyrate has a fruity odor reminiscent of apple or pineapple and a sweet flavor reminiscent of rum. May be prepared by esterification of butyric acid with isobutyl alcohol in the presence of concentrated H2S04; or by enzymatic action of hog pancreas on a mixture of isobutyl alcohol and butyric acid in the absence of water.

Chemical properties

Isobutyl butyrate has a fruity, ethereal odor reminiscent of apple or pineapple and a sweet flavor reminiscent of rum.

Definition

ChEBI: A butyrate ester resulting from the formal condensation of butanoic acid with isobutanol. It is used as a food flavour ingredient for apple, banana, peach and pinapple flavours in ice cream and confectionery.

Preparation

By esterification of butyric acid with isobutyl alcohol in the presence of concentrated H2SO4, or by enzymatic action of hog pancreas on a mixture of isobutyl alcohol and butyric acid in the absence of water.

Taste threshold values

Taste characteristics at 20 ppm: sweet, fruity, pineapple, apple, bubble gum and tutti-frutti. Natural occurrence: Reported found in apricot, banana, apple, strawberry, blue and Gruyere cheeses, cognac, port wine, rum, honey, olive, passion fruit, plum, beans, mushrooms, mango, apple brandy, quince, cherimoya, kiwifruit and Chinese quince pee

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 5307, 1991 DOI: 10.1021/jo00018a019

General Description

Isobutyl butyrate is an aliphatic ester that can be used as a food flavoring agent. It is one of the volatile flavor compounds produced in ripening bananas.

Safety Profile

Mdly toxic by ingestion and intraduodenal routes. A skin irritant. See also ESTERS. When heated to decomposition it emits acrid smoke and irritating fumes.