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.)
2000; Wiley; Volume: 35; Issue: 9 Linguagem: Inglês
10.1007/s11745-000-0605-z
ISSN1558-9307
AutoresBernd A. W. Gallasch, Gerhard Spiteller,
Tópico(s)Lipid metabolism and biosynthesis
ResumoAbstract 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.
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