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Lack of regioselectivity in formation of oxohydroxy octa decenoic acids from the 9 hydro per oxide or 13 hydro per oxide of linoleic acid

, : Lack of regioselectivity in formation of oxohydroxy octa decenoic acids from the 9 hydro per oxide or 13 hydro per oxide of linoleic acid. Lipids 14(10): 848-851

Either 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid or 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid was treated with the catalyst, cysteine-FeCl3, in the presence of O2. Oxohydroxyoctadecenoic acids were among the many products formed as a result of hydroperoxide decomposition. A mixture of 9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoic acids (.delta.-ketols) was produced from either isomeric hydroperoxide. The formation of isomeric .delta.-ketols from 9-hydroxy-trans-12,13-epoxy-trans-10-octadecenoic acid (epoxyol), a known product of 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid decomposition, implies that the epoxyol is an intermediate. The mechanism was elucidated by the facile conversion of the epoxyol (methyl ester) to methyl-9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoates with a Lewis acid, BF3-etherate.


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