Vernolic acid

Vernolic acid (leukotoxin) is an organic compound and a fatty acid. This monounsaturated long chain carboxylic acid contains an epoxide and consists of two optical isomers. The (+) optical isomer's IUPAC designation is (+)-(12S,13R)-epoxy-cis-9-octadecenoic acid; it is also termed 12S,13R-EpOME, cis-12-epoxyoctadeca-cis-9-enoic acid, and (9Z)-(12S,13R)-12,13-epoxyoctadecenoic acid. The (-) isomer's IUPAC designation is (-)-(12R,13S)-epoxy-cis-9-octadecenoic acid; it is also termed 12R,13S-EpOME, cis-12-epoxyoctadeca-cis-9-enoic acid, and (9Z)-(12R,13S)-12,13-epoxyoctadecenoic acid. It is an isomer of coronaric acid, which is itself the (+) and (-), i.e. R,S and S,R optical isomers of 9,10-epoxy-12Z-octadecenoic acid (also termed 9(10)-EpOME and (+/-)-9(10)-epoxy-12Z-octadecenoic acid). Vernolic acid was first definitively characterized in 1954. It is the key component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.