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Naturally occurring epoxy acids. IV. The absolute optical configuration of vernolic acid
Author(s) -
Morris L. J.,
Wharry D. M.
Publication year - 1966
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02668123
Subject(s) - absolute configuration , epoxy , ricinoleic acid , stereospecificity , absolute (philosophy) , chemistry , organic chemistry , fatty acid , chromatography , stereochemistry , catalysis , philosophy , epistemology , castor oil
Vernolic acid [(+)‐ cis ‐12,13‐epoxyleic acid] was transformed by stereospecific reactions to a mixture of threo ‐9,10,12‐and threo ‐9,10,13‐trihydroxyoctadecanols. The four components of this mixture were separately isolated by chromatography on thin layers impregnated with glycol‐complexing agents. The 9,10,12‐trihydroxyoctadecanols so obtained were identical to the corresponding derivatives of D‐(+)‐ricinoleic acid, thereby proving the absolute optical configuration of the epoxy group of vernolic acid to be D. As a corollary to this the absolute configurations of some other oxygenated fatty acids have been deduced.