Epoxy acid in seed oils of Malvaceae and preparation of (+) threo-12,13-Dihydroxyoleic acid

Abstract

Seed oils of six species of Malvaceae, representing four genera, were found to contain cis-12,13-epoxyoleic acid in amounts estimated at 1,5–7% of the total fatty acids. Acetolysis of the oils gave the corresponding dihydroxyoleic acid, which was shown to be predominantly a dextro-rotatory form of threo-12,13-dihydroxyoleic acid. It was obtained optically pure, and its structure was confirmed by orthodox methods. The hydrogenation product, (+)- threo-12,13-dihydroxystearic acid, was also obtained optically pure and characterized. The best yield of dihydroxyoleic acid was obtained from the seed oil of Malope trifida. Samples of oil from four other species of Malvaeae had a very low or negligible content of epoxy acid. © 1960, The American oil Chemists’ Society. All rights reserved.