ARS | Publication request: ALL (S) STEREOCONFIGURATION OF 7,10-DIHYDROXY-8(3)-OCTADECENOIC ACID FROM BIOCONVERSION OF OLEIC ACID BY PSEUDOMONAS AERUGINOSA

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 27, 1999
Publication Date: N/A

Interpretive Summary: Previous work showed the bioconversion of vegetable oil into a compound could be useful either as a replacement for castor oil, surfactant manufacture, an ingredient in cosmetics, or as a precursor of pharmaceuticals. If this compound is to become useful to the pharmaceutical industry, its structure must be known in detail. This work now gives the complete structure of this bioconversion product, which previously was partly known. This work would be of interest to the biotechnology industry.

Technical Abstract: A previously established method was utilized to determine the stereoconfiguration of 7,10-dihydroxy-8(E)-octadecenoic acid (DHOE) 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 workers, the 2(S)-MC derivatives elute at earlier times by gas chromatography (GC) than the 2(R)-MC derivatives. Comparing the GC analysis of the 2-(MC) derivatives obtained from DHOE with that obtained from a partially racemized sample, DHOE was determined to be 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid.