Identification of hydroxyl and hydroperoxyl carbonyls in autoxidized triglyceride.

The degradation products in autoxidized linseed oil which are reactive to amino acids were investigated. The degradation product fractions prepared by gel chromatography on Sephadex LH-20, followed by HPLC on μ-Porasil, were allowed to react with GLY, and the presence of the reactive compounds in the fractions was confirmed by GLC and GC-MS analyses. Furthermore, after the reduction with NaBH4 and SnCl2 and by the catalytic hydrogenation, and the subsequent conversion of the carbonyl grouo into dimethylhydrozane and the hydroxyl group into trimethylsilyl ether, the reactive compounds were analyzed in detail by GC-MS and high resolution mass spectrometry. In the results, 4-OH-and 4-OOH-2-hexenals, 4-OH-and 4-OOH-2-nonenals, 6-OH- and 6-OOH-2, 4-octadienals, 3, 4-diOH-hexanal, 4, 5-diOH-3-heptenal, and 6, 7-diOH-2, 5-nonadienal were identified. Except for the first four, these compounds from autoxidized lipids are reported for the first time.