Summary
Previously, we reported the discovery of a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) which was produced from oleic acid by a new bacterial isolate PR3 [6,7]. The reaction is unique in that it involves a hydroxylation at two positions and a rearrangement of the double bond of the substrate molecule. Now, we have isolated another compound from the reaction mixture determined by GC/MS to be 10-hydroxy-8-octadecenoic acid (HOD). NMR and IR data indicate that the unsaturation is probablycis. The optimum pH and temperature for the production of HOD by strain PR3 were 6.5 and 30°C, about the same as those for DOD. However, the amount of HOD detected remained small throughout an 48-h reaction period during which the amount of DOD increased sharply. At 48 h of reaction, the ratio between HOD∶DOD was 1∶10. HOD may be an intermediate in the biosynthesis of DOD from oleic acid.
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Hou, C.T., Bagby, M.O. 10-Hydroxy-8(Z)-octadecenoic acid, an intermediate in the bioconversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid. Journal of Industrial Microbiology 9, 103–107 (1992). https://doi.org/10.1007/BF01569740
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DOI: https://doi.org/10.1007/BF01569740