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United States Department of Agriculture

Agricultural Research Service

Title: 10(s)-Hydroxy-8(e)-Octadecenoic Acid, An Intermediate in the Conversion of Oleic Acid to 7,10-Dihydroxy-8(e)-Octadecenoic Acid

Authors
item Kim, Hakryul
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: The new bacterial isolate Pseudomonas sp. 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 intermediate. The reaction is unique in that it involves an introduction of two hydroxyl groups at carbon number 7 and 10 and a rearrrangement of the double bond from carbon 9 to 8. In another paper presented at this meeting, Gardner & Hou reported that the chiral properties of DOD is in 7(S), 10(S) configuration with a minor isomer (about 3%) in its 7(S), 10(R) form. On HOD, our previous report indicated that its 8,9 unsaturation is possibly in cis form. Now we report that the rearranged double bond of HOD turned out to be trans rather than cis by NMR and IR data, and we also found out that carbon number 10 on which a hydroxyl group was introduced represented S configuration by methoxycarbonyl- chloride (MC) derivatization of hydroxy group and followed oxidative cleavage of the double bond and methyl esterification. In addition, a minor isomer of HOD (about 3%) with 10(R) configuration was also detected, which coincided with our recent findings that the main final product DOD represented 7(S), 10(S)-dihydroxy configuration (97%) with 7(S), 10(R)-dihydroxy configuration as minor isomer (about 3%).

Last Modified: 11/25/2014
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