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.)

被引：16

作者：

Gallasch, BAW ^{[1
]}

Spiteller, G ^{[1
]}

机构：

[1] Univ Bayreuth, D-95440 Bayreuth, Germany

来源：

LIPIDS | 2000年 / 35卷 / 09期

关键词：

D O I：

10.1007/s11745-000-0605-z

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The previously unknown linoleic acid peroxidation product 9,12-dioxo-10(Z)-decenoic acid (Z5) was detected in lentil seed flour (Lens culinaris Medik.) by electron impact mass spectrometry (EI-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.

引用

页码：953 / 960

页数：8

共 35 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].