10-hydroxy-8-octadecenoic acid formation

Hamberg, M. and B. Gotthammar. 1973. A new reaction of unsaturated fatty acid hydroperoxides formation of 11-hydroxy-12,13-epoxy-9-octadecenoic acid from... 

The production of DOD from oleic acid is unique in that it involves an addition of two hydroxy groups at two positions and a rearrangement of the double bond of the substrate molecule. The reaction at the A9,10 position resembles hydration, and the reaction at the C-7 position seems like a hydroxylation. Subsequent investigation of reactions catalyzed by PR3 led to the isolation of another new compound, 10-hy-droxy-8-octadecenoic acid (HOD) (34). From the structure similarity between HOD and DOD, it is likely that HOD is an intermediate in the formation of DOD from oleic acid by strain PR3. Kinetic studies (34) showed that the conversion from HOD to DOD is not a rate-limiting step. The bioconversion pathway for flie production of DOD from oleic acid is postulated as follows (Fig. 3) a hydratase in strain PR3 attacks oleic acid at the C-10 position, introduces a hydroxy group, and at the same time shifts the double bond from C-9 to C-8. The resulting product (HOD) is then oxidized by a hydroxylase at the C-7 position to produce DOD. 

Hou, C.T., and M.O. Bagby, 10-Hydroxy-8(Z)-Octadecenoic Acid, an Intermediate in the Formation of 7,10-Dibydroxy-8( )-octadecenoic Acid from Oleic Acid by Pseudomonas sp. PR3, J, Indust. Micwbiol. 9 103-107 (1992). 

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