DL-3-Methylvaleric acid

Description

3-Methylpentanoic has a sour, herbaceous, slightly green odor. This is synthesized from the diethylester of sec-butyl-malonic acid.

Chemical properties

clear colorless to slightly yellow liquid

Occurrence

Reported found in the oil from tobacco leaves (d-form), baked potato, parmesan, provolone and romano cheese, goat and sheep cheese, lamb fat, rum, cocoa, black tea and chempedak (Arthocarpus polyphema).

The Uses of DL-3-Methylvaleric acid

3-Methylvaleric acid (3-Methylpentanoic acid) was used in the synthesis of 3-methyl-1-pentanol.

Preparation

From the diethylester of sec-butyl-malonic acid.

Definition

ChEBI: 3-methylvaleric acid is a methyl-branched fatty acid that is pentanoic acid which carries a methyl group at position 3. It has a role as a plant metabolite, an animal metabolite, a fungal metabolite and a flavouring agent. It is a methyl-branched fatty acid, a short-chain fatty acid, a branched-chain saturated fatty acid and a monocarboxylic acid. It is a conjugate acid of a 3-methylvalerate.

Aroma threshold values

Detection: 46 to 280 ppb

Taste threshold values

Taste characteristics at 30 ppm: sour, cheesey, fresh with fruity notes

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 6342, 1953 DOI: 10.1021/ja01120a539
The Journal of Organic Chemistry, 65, p. 397, 2000 DOI: 10.1021/jo991218a
Organic Syntheses, Coll. Vol. 2, p. 416, 1943