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United States Department of Agriculture

Agricultural Research Service

Title: Configurational Purity of Lesquerolic Acid

Authors
item Sonnet, Philip
item Hayes Douglas,

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: July 1, 1995
Publication Date: N/A
Full Text Available

Interpretive Summary: Seed oil from Lesquerella fendleri, a potential new crop currently under development by the U.S. Department of Agriculture and private sector partners, contains a hydroxylated fatty acid that could be of use as an industrial lubricant. This acid could be of additional use in general organic synthesis for fine chemicals if the configuration (geometry) about the hydroxyl-bearing carbon was ascertained with certaint to be homogeneous. This report determines the configurational purity of that acid, and indicates its potential utility for the production of value-added materials.

Technical Abstract: 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.

Last Modified: 4/15/2014
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