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Hydroxy fatty acids through hydroxylation of oleic acid with selenium dioxide/ tert. ‐butylhydroperoxide
Author(s) -
Knothe G.,
Weisleder D.,
Bagby M. O.,
Peterson R. E.
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02552714
Subject(s) - chemistry , selenium , oleic acid , hydroxylation , organic chemistry , hydrazine (antidepressant) , fatty acid , chromatography , biochemistry , enzyme
Oleic acid was hydroxylated in the allylic positions with the selenium dioxide/ tert. ‐butylhydroperoxide system to give 8‐hydroxy‐9( E )‐octadecenoic acid, 11‐hydroxy‐9( E )‐octadecenoic acid and the novel 8,11‐dihydroxy‐9( E )‐octadecenoic acid. This is a viable method for obtaining hydroxy fatty acids. The unsaturated hydroxy acids were hydrogenated with the hydrazine/air system to give the cor‐responding saturated products. 8,11‐Dihydroxyoctadecanoic acid thus obtained is also a novel compound. The saturated and unsaturated dihydroxy products were obtained as erythro/threo isomers as determined by nuclear magnetic resonance.