caa a22 4500 46576536X CHVBK 20180323111912.0 cr unu---uuuuu 170327e19900101xx s 000 0 eng 10.1007/BF02562425 doi (NATIONALLICENCE)springer-10.1007/BF02562425 Autoxidation of polyunsaturated triacylglycerols. I. Trilinoleoylglycerol [Elektronische Daten] [W. Neff, E. Frankel, K. Miyashita] The hydroperoxides and secondary products formed from trilinoleoylglycerol autoxidized at 40°C were isolated and characterized to clarify their contribution to oxidative deterioration of vegetable oils. The products were purified by high performance liquid chromatography (HPLC) and identified, as intact triacylglycerols, by ultraviolet, infrared,1H NMR and13C NMR analyses, and after derivatization by lipolysis, gas chromatography, and gas chromatography-mass spectrometry. The main, primary products included mono-,bis- and tris-9-hydroperoxy-trans-10,cit-12-; 9-hydroperoxy-trans-10,trans-12; 13-hydroperoxy-cis-9,trans-11; and 13-hydroperoxy-trans-9,trans-11-linolenoyl glycerols. The structures of the minor secondary products analyzed after derivatization were consistent with known oxidative degradation products of linoleate hydroperoxides. HPLC analyses showed that thebis- and tris-hydroperoxides were formed from the mono-hydroperoxides during autoxidation at peroxide values above 18 and 28 meq/kg. Studies on the further oxidation of the mono-hydroperoxides support a mechanism for the consucutive formation ofbis- and tris-hydroperoxides from the monohydroperoxides. HPLC analyses showed that no preferential oxidation occurred between the 1(3)- and 2-triglyceride positions. Hydroperoxides of linoleate triacylglycerols may be important precursors of volatile compounds contributing to off-flavors of vegetable oils. the American Oil Chemists' Society (AOCS), 1990 Neff W. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut Frankel E. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut Miyashita K. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut Lipids Springer-Verlag 25/1(1990-01-01), 33-39 0024-4201 25:1<33 1990 25 11745 https://doi.org/10.1007/BF02562425 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02562425 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Neff W. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut NATIONALLICENCE 700 1- Frankel E. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut NATIONALLICENCE 700 1- Miyashita K. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/1(1990-01-01), 33-39 0024-4201 25:1<33 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer