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.)
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.
Gallasch
B A
BA
Organische Chemie I, Universität Bayreuth, Germany.
Spiteller
G
G
D002849:Chromatography, Gas; D007887:Fabaceae / Q000737:chemistry* / Q000378:metabolism; D005229:Fatty Acids, Monounsaturated / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D006898:Hydroxylamines / Q000378:metabolism; D007850:Lauric Acids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D008041:Linoleic Acids / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal; D012639:Seeds / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D005466:Fluorocarbons
D005229:Fatty Acids, Monounsaturated; D006898:Hydroxylamines; D007850:Lauric Acids; D008041:Linoleic Acids; C418762:9,12-dioxo-10-dodecenoic acid; C010277:Florox Reagent; D005466:Fluorocarbons; C049606:9-hydroperoxy-11,12-octadecadienoic acid