ARS | Publication request: 10(S)-HYDROXY-8(E)-OCTADECENOIC ACID, AN INTERMEDIATE IN THE CONVERSION OF OLEIC ACID TO 7,10-DIHYDROXY-8(E)-OCTADECENOIC ACID

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 24, 1999
Publication Date: N/A

Interpretive Summary: Hydroxy fatty acids are important industrial materials derived from vegetable oils. Scientists at the National Center in Peoria have discovered hydroxy fatty acids produced from converting vegetable oils by microbial enzymes, which may be useful as starting materials for the synthesis of specialty chemicals, special military nylon, plasticizer, and anti-microbial agents. One of the hydroxy fatty acids, 7,10-dihydroxy-8(E)-octadecenoic acid was produced from oleic acid, a component of soybean and corn oil, by a soil microorganism. During our scale-up production of this product, we isolated another hydroxy fatty acid as an intermediate in its biosynthesis. The structure of this new product was determined by many chemical and instrumental analyses. Application of these hydroxy fatty acid products either as agents for anti- pathogenic fungi or as high volume starting materials for the synthesis of special military nylon will benefit the U.S. farmers.

Technical Abstract: The new bacterial isolate Pseudomonas aeruginosa (PR3) has been reported to produce a new compound 7,10-dihydroxy-8(E)- octadecenoic acid (DOD) from oleic acid with 10-hydroxy-8- octadecenoic acid (HOD) being possible intermediate. The reaction is unique in that it involves an introduction of two hydroxyl groups at carbon number 7 and 10 and a rearrangement of the double bond from carbon 9 to 8. In a previous report, HOD has been shown that its 8 unsaturation is possibly in cis form. Now we report that the rearranged double bond of HOD is trans rather than cis by NMR and FTIR data, and we also found out that carbon number 10 on which a hydroxyl group was introduced represented S-configuration by (-)-menthoxycarbonylchloride (MCO) derivatization of the hydroxyl group followed by oxidative cleavage of the double bond and methyl esterification. This result coincided with our recent findings that the main final product DOD represented 7(S),10(S)-dihydroxy configuration. In addition, a minor isomer of HOD (about 3%) with 10(R) configuration was also detected. From the data obtained herein, we concluded that oleic acid was bio-converted by PR3 mainly to 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid with 10(S)- hydroxy-8(E)-octadecenoic acid and a minor isomer (about 3%) of 10(R)-hydroxy-8(E)-octadecenoic acid being possible intermediate.