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Synthesis of 9,12‐Dioxo‐10( Z )‐dodecenoic acid, a new fatty acid metabolite derived from 9‐hydroperoxy‐10,12‐octadecadienoic acid in lentil seed ( Lens culinaris medik.)
Author(s) -
Gallasch Bernd A. W.,
Spiteller Gerhard
Publication year - 2000
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/s11745-000-0605-z
Subject(s) - derivatization , chemistry , diazomethane , trimethylsilyl , linoleic acid , metabolite , chromatography , linolenic acid , gas chromatography–mass spectrometry , fatty acid , mass spectrometry , hydroxylamine , hydrochloride , organic chemistry , biochemistry
Abstract The previously unknown linoleic acid peroxidation product 9,12‐dioxo‐10( Z )‐decenoic acid ( Z5 ) was detected in lentil seed fluor ( Lens culinaris Medik.) by electron impact mass spectrometry (El‐MS) after derivatization with pentafluorobenzyl‐hydroxylamine‐hydrochloride, methylation of acidic groups with diazomethane, and protection of hydroxylic groups with N ‐methyl‐ N ‐trimethylsilyl‐trifluoroacetamide. The structure of the natural product was confirmed by synthesis of Z5 , 9,12‐dioxo‐10( E )‐decenoic acid, and derivatives. EI‐MS, nuclear magnetic resonance and gas chromatographic data of these compounds and synthetic intermediates are discussed.