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Syntheses with stable isotopes: Oleic‐1‐ 13 C acid and triolein‐1′,1″, 1″′‐ 13 C 3
Author(s) -
Whaley T. W.,
Daub G. H.,
Walker R. D.,
Williams D. L.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580181105
Subject(s) - triolein , chemistry , oleic acid , hydrolysis , yield (engineering) , sodium , organic chemistry , condensation , nuclear chemistry , medicinal chemistry , lipase , biochemistry , materials science , metallurgy , enzyme , physics , thermodynamics
A synthesis of oleic‐1‐ 13 C acid and its conversion to triolein‐1′,1″,1″′‐ 13 C 3 are described. 9‐Octadecynenitrile‐1‐ 13 C was prepared from 1‐bromo‐8‐heptadecyne and sodium cyanide‐ 13 C. Hydrolysis afforded stearolic‐1‐ 13 C acid, which was reduced to oleic‐1‐ 13 C acid by the action of disiamylborane on methyl stearolate‐1‐ 13 C. Hydrogenation of stearolic acid in the presence of Lindlar's catalyst was also investigated. Condensation of glycerol and oleic‐1‐ 13 C acid to give triolein‐1′,1″,1″′‐ 13 C 3 was effected with dicyclohexylcarbodiimide and 4‐dimethylaminopyridine. The overall yield of triolein‐ 13 C 3 from sodium cyanide‐ 13 C was 40%.