Optically active trihydroxy acids ofChamaepeuce seed oils

Abstract

Two trihydroxy acids have been isolated fromChamaepeuce 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 unidentifiedChamaepeuce species apparently contain these same two acids but in different proportions fromC. afra oil.