Malvalic acid

This unusual molecule is thought to be one of the causes of abnormalities that develop in animals that ingest cottonseed oil.

An α-oxidation reaction removes one carbon from the chain to form the 17-carbon-chain structure of malvalic acid.

Smith and Bu'Lock[5] showed that in Hibiscus seedlings the chains of sterculic and malvalic acids, but not the ring methylene carbon, were derived from acetate.

They explained the shortening by α oxidation occurring during the biogenesis of malvalic acid.

Hooper and Law[6] demonstrated that the ring methylene carbon of both cyclopropane and cyclopropene acids was derived from the methyl group of methionine in Hibiscus, and suggested from the distribution of label that the pathway was oleic → dihydrosterculic → sterculic acid.

Biosynthesis