Determination of oxidation products of N-phenyllinoleamide: Spanish toxic oil syndrome studies.
The early identification of fatty acid anilides in suspect oils directed attention to their possible role in the Spanish toxic oil syndrome. These anilides or their oxidized derivatives could have been spontaneously formed during the handling and/or storage of the oil. The exact cause of the intoxication is still unknown but free radical and peroxidative mechanisms have been implicated in its etiology. Epoxy-hydroxylated derivatives from linoleic acid anilide were obtained using a model of accelerated oxidation. Their mass spectral patterns agree with the trimethylsilyl ethers of N-phenyl-9,10-epoxy-11-hydroxy-12-octadecenamide and N-phenyl-12,13-epoxy-11-hydroxy-9-octadecenamide, respectively. These compounds were also identified is rapeseed oil samples supplemented with N-phenyl-linoleamide and submitted to the reported accelerated oxidation method.
Cárdenas
A
A
Department of Neurochemistry, Centro de Investigación y Desarrollo (CSIC), Barcelona, Spain.
Abián
J
J
Bulbena
O
O
Roselló
J
J
Gelpi
E
E
D000813:Anilides / Q000032:analysis*; D001937:Brassica / Q000032:analysis; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000302:isolation & purification; D005506:Food Contamination / Q000032:analysis*; D008401:Gas Chromatography-Mass Spectrometry; D008041:Linoleic Acids / Q000032:analysis*; D010084:Oxidation-Reduction; D010938:Plant Oils / Q000032:analysis / Q000506:poisoning*; D012997:Solvents
D000813:Anilides; D005227:Fatty Acids; D008041:Linoleic Acids; D010938:Plant Oils; D012997:Solvents; C039294:linoleylanilide