Lamenallenic acid

Lamenallenic acid is a linear octadecatrienic fatty acid with the structural formula CH3-CH=CH-8-CH=C=CH-3-COOH. The delta notation is 18:3-delta-5,6allene,16t. This is one of the rare allenic fatty acids found in nature, probably biosynthesized from laballenic acid.

Physical properties

Some authors have attributed the cis-configuration to the double bond in the position 16=17.
The allene group is responsible for the marked optical activity of the acid. Lamenallenic acid is levorotatory with -configuration.

Discovery

The acid was initially isolated in 1967 by Mikolajczak, Rogers, Smith, and Wolff in the seed oil of Lamium purpureum, a plant of the Lamiaceae family. The compound is also found in the seed oil of other Lamiaceae: Lamium maculatum, Lamium album, Lamium amplexicaule.

Synthesis

The acid can be obtained by a highly enantioselective synthesis, utilizing the recently developed EATA reaction and aerobic oxidation reaction.