153491-94-2Relevant academic research and scientific papers
Synthesis of (2,3-13C2) eruric acid
Olsen,Bukata
, p. 899 - 906 (1993)
The synthesis of (2,3-13C2) erucic acid, for use in metabolic studies, is reported. The synthesis employs a repeated 3 step reaction sequence using 13C labeled triethylphosphonoacetate to extend C(18:1), oleyl alcohol, by 4 carbons. The starting alcohol is first oxidized with PCC and the resulting aldehyde is condensed with triethyl(1-13C)phosphonoacetate. The product, an α,β unsaturated ester, is reduced with (Ph3PCuH)6 to ethyl eicosenoate. Reduction with LAH gives eicosenoyl alcohol. A repetition of the reaction sequence using triethyl(2-13C) phosphonoacetate results in ethyl(2,3-13C2)erucate. The (2,3-13C2) erucic acid, obtianed by hydrolysis with alcoholic KOH, gave 13C NMR signals of δ 24.6 and 34.1 ppm for C-3 and C-2 respectively with a J = 34.9 Hz. The overall yield was 5.5%.
