Related Experiment Video
Updated: Jul 12, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Optically active trihydroxy acids ofChamaepeuce seed oils
1Northern Regional Research Laboratory, Peoria, Illinois.
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.
Related Concept Videos
Prochirality
Properties of Enantiomers and Optical Activity
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Direct-Acting Cholinergic Agonists: Pharmacokinetics
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
The direct-acting...

