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Structure and intraglyceride distribution of coriolic acid
Author(s) -
Tallent W. H.,
Harris Jeanne,
Spencer G. F.,
Wolff I. A.
Publication year - 1968
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/bf02531282
Subject(s) - chemistry , double bond , hydrolysis , permanganate , periodate , ozonolysis , chromic acid , organic chemistry , conjugated system , triglyceride , acid hydrolysis , linoleic acid , bstfa , fatty acid , catalysis , biochemistry , silylation , polymer , cholesterol
Coriolic [( R )‐13‐hydroxy‐ cis ‐9, trans ‐11‐octadecadienoic] acid (III, R=Z=H) was isolated as the methyl ester from two Coriaria seed oils in 66 and 68% yields. The double bonds and hydroxyl group were located by periodate‐permanganate oxidation before, and chromic acid oxidation after, hydrogenation of the double bonds. Alternatively the positions of the functional groups were indicated by a convenient micro‐ozonolysis‐gas‐liquid chromatographic procedure. Determination of products from partial hydrolysis of the Coriaria oils with pancreatic lipase (EC 3.1.1.3) revealed a preference of the corioloyl group for the 1,3‐positions in triglyceride molecules. The possible significance of coriolic acid as an intermediate in the biogenetic conversion of linoleic acid to conjugated trienoic acids is discussed.