Merck
  • Home
  • Search Results
  • 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.)

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.)

Lipids (2000-10-12)
B A Gallasch, G Spiteller
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylamine hydrochloride, ≥98%
Supelco
O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylamine hydrochloride, for GC derivatization, LiChropur, ≥99.0% (AT)