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United States Department of Agriculture

Agricultural Research Service

Title: All (S) Stereoconfiguration of 7,10-Dihydroxy-8(e)-Octadecenoic Acid from Bioconversion of Oleic Acid by Pseudomonas Aeruginosa Nrrl Strain B-18602 (Pr3)

Authors
item Gardner, Harold
item Hou, Ching

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 12, 1999
Publication Date: N/A

Technical Abstract: A previously established method was utilized to determine the stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) from bioconversion of oleic acid by Pseudomonas aeruginosa NRRL strain B-18602 (PR3). The method involved formation of the (-)-menthoxycarbonyl (MC) derivative of the two hydroxyls, oxidative cleavage of the double bond, and gas chromatographic analysis of the two methyl esterified diastereomeric fragments, methyl 2-(MC)-decanoate and dimethyl 2-(MC)-octanedioate. As described by previous work, the 2(S)-MC derivatives elute before the 2(R)-MC derivatives by gas chromatography (GC). Comparing the GC analysis of the 2-(MC) derivatives obtained from DOD with that obtained from a partially racemized DOD, this fatty acid was determined to be 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid.

Last Modified: 11/26/2014
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