Optically active trihydroxy acids of Chamaepeuce seed oils

Abstract

Two trihydroxy acids have been isolated from Chamaepeuce afra (Jacq.) DC, seed oil and identified as (+)-threo-9,10,18-trihydroxyoctadecanoic (phloionolic) acid (9%) and (+)-threo-9,10-,18-trihydroxy-cis-12-octadecenoic acid (14%). The unsaturated acid has not previously been found in nature. Nuclear magnetic resonance, infrared, thin-layer chromatography, optical rotation, and identification of the oxidative cleavage products show that these two trihydroxy components have the structures indicated. Chamaepeuce hispanica DC. seed oil and the seed oil of an unidentified Chamaepeuce species apparently contain these same two acids but in different proportions from C. afra oil. © 1967 American Oil Chemists' Society.