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Syntheses with stable isotopes: Oleic-1-13C acid and triolein-1′,1″, 1″′-13C3

✍ Scribed by T. W. Whaley; G. H. Daub; R. D. Walker; D. L. Williams

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
438 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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%.

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