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.)

Overview

Journal Lipids

Specialty Biochemistry

Date 2000 Oct 12

PMID 11026615

Citations 4

Authors

B A Gallasch

G Spiteller

Affiliations

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Abstract

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-l0(E)-decenoic acid, and derivatives. EI-MS, nuclear magnetic resonance and gas chromatographic data of these compounds and synthetic intermediates are discussed.

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