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Inevitable generation of primary alcohols during reduction of oxidized lipids with sodium borohydride
Author(s) -
Nakamura Takashi,
Maeda Hiroyuki,
Takahashi Yoshino,
Hama Yoichiro
Publication year - 1990
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/bf02537169
Subject(s) - chemistry , sodium borohydride , palmitic acid , sodium methoxide , glyceride , chromatography , high performance liquid chromatography , organic chemistry , solvent , derivatization , fatty alcohol , fatty acid , nitrile , methanol , catalysis
This report deals with the fluorometric determination of fatty alcohols generated by the reduction of the ester linkage of lipids with NaBH 4 , and with the limitations of the reduction method for assaying oxidized lipids. Optimum conditions for the fluorometric analysis of primary and secondary alcohols using 1‐anthroyl nitrile were obtained. After reduction with NaBH 4 in MeOH or in MeOH/benzene (8∶2, v/v), the formation of 1‐hexadecanol from a variety of palmitic acid esters was measured fluorometrically by reverse‐phase high‐performance liquid chromatography (HPLC): From glycerides and methyl palmitate, 1–3% (w/w) 1‐hexadecanol was produced and a trace was produced from cholesteryl palmitate (10 min, 21°C). 1‐Hexadecanol was never generated from palmitic acid. Although considerable improvement occurred with the choice of the solvent for the NaBH 4 reduction, the generation of primary alcohols from ester lipids usually seems inevitable.