caa a22 4500 465765343 CHVBK 20180323111912.0 cr unu---uuuuu 170327e19900101xx s 000 0 eng 10.1007/BF02562426 doi (NATIONALLICENCE)springer-10.1007/BF02562426 Autoxidation of polyunsaturated triacylglycerols. II. Trilinolenoylglycerol [Elektronische Daten] [E. Frankel, W. Neff, K. Miyashita] The hydroperoxides and secondary products formed from trilinolenoylglycerol autoxidized at 40°C were isolated and characterized to clarify the mechanism of oxidative deterioration of polyunsaturated vegetable oils. The products were purified by high performance liquid chromatography (HPLC) and identified either as intact triacylglycerols spectrophotometrically, or after lipolysis (pancreatic lipase) and capillary gas chromatography and gas chromatography-mass spectrometry. The products included 9-, 12-, 13-, and 16-mono-,bis-, tris-hydroperoxy, 9- and 16-hydroperoxy epidioxy, 9- and 16-hydroperoxy bicycloendoperoxy and 9,12-, 13,16-, and 9,16-dihydroperoxy linolenoylglycerols. The mono-hydroperoxides and sydroperoxy epidioxides were the only main products initially formed at peroxide values (PV) below 30.Bis- and tris-hydroperoxides were formed consecutively as minor products from the mono-hydroperoxides at PV's between 31 and 47. Hydroperoxy bicycloendoperoxides and monodihydroperoxides were also formed as minor secondary products at PV's above 75. HPLC analyses show a small preference for the formation of 16-hydroperoxides on the 1(3)-position over the 2-position of trilinolenoylglycerol. However, there was no selectivity for the formation of the 9-, 12- and 13-hydroperoxides and for the hydroperoxy epidioxides between the 1(3)- and the 2-positions in trilinolenoylglycerol. Mono-hydroperoxides and hydroperoxy epidioxides of linolenate triacylglycerols may be important precursors of volatile compounds contributing to oxidative deterioration of vegetable oils. the American Oil Chemists' Society (AOCS), 1990 Frankel E. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut Neff W. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut Miyashita K. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut Lipids Springer-Verlag 25/1(1990-01-01), 40-47 0024-4201 25:1<40 1990 25 11745 https://doi.org/10.1007/BF02562426 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02562426 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Frankel E. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut NATIONALLICENCE 700 1- Neff W. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut NATIONALLICENCE 700 1- Miyashita K. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 N. University St., 61604, Peoria, IL aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/1(1990-01-01), 40-47 0024-4201 25:1<40 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer