Usee
Isobutyl butyrate is a metabolite of Rifampicin, a Rifamycin antibiotic.
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.
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.
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.
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.
