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Preparation of methyl 5,11,14,17-eicosatetraenoate-8,8,9,9-d 4

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Lipids

Abstract

For studies of incorporation, elongation and desaturation of fats in humans and animals, methyl 5,11,14,17-eicosatetraenoate-8,8,9,9-d 4 was prepared by Wittig coupling, in the presence of sodiumbis(trimethylsilyl) amide, of 6,9,12-pentadecatrienal-3,3,4,4-d 4 and 4-carboxybutyltriphenylphosphonium bromide. The all-cis isomer was separated fromtrans isomers and other impurities by silver resin chromatography. Location and configuration of the double bonds and deuterium atoms were affirmed by nuclear magnetic resonance and mass spectrometry.

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Abbreviations

DHP:

dihydropyran

EE:

diethyl ether

GC:

gas chromatography

NMR:

nuclear magnetic resonance

PE:

petroleum ether (35–60°C)

p-TSA:

p-toluenesulfonic acid

THF:

tetrahydrofuran

THP:

tetrahydropyranyl

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Authors and Affiliations

  1. Food Quality and Safety Research, National Center for Agricultural Utilization Research, ARS, U.S. Department of Agriculture, 1815 N. University Street, 61604, Peoria, Illinois

    Henry Rakoff

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  1. Henry Rakoff
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Rakoff, H. Preparation of methyl 5,11,14,17-eicosatetraenoate-8,8,9,9-d 4 . Lipids 28, 47–50 (1993). https://doi.org/10.1007/BF02536359

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  • DOI: https://doi.org/10.1007/BF02536359

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