Configurational Purity of Lesquerolic Acid

Article abstract of DOI:10.1007/BF02660724

Conversion of the methyl ester of lesquerolic acid, (R)-14-hydroxy-Z-11-eicosenoic acid, to a carbamate with (S)-1-(1'-naphthyl)ethylisocyanate gave a single diastereomer.Comparisons of elution orders of the relevant diastereomers obtained from the racemic ester and from a sample of lesquerolic acid synthesized from ricinoleic acid, (R)-12-hydroxy-Z-9-octadecenoic acid, were consistent with the original assignment of (R)-configuration for the longer-chain acid.Although the configuration had not been in doubt, this work demonstrates the configurational purity of the lesquerolic acid.KEY WORDS: Configuration, 1H NMR (of diastereomers), HPLC (of diastereomers), lesquerolic acid, ricinoleic acid.