Abstract
Commercially refined soybean oil was heated at 180 C for 50, 70 or 100 hr with aeration. The triacylglycerol fractions separated from the oils by column chromatography on silica gel were fractionated further by silicic acid thin layer chromatography (TLC), and species compositions were determined by argentation TLC and lipase hydrolysis. There was a decrease in the absolute amounts of the triacylglycerols with longer heating periods, such as 21% for 50 hr and 42% for 100 hr. Relatively large changes occurred in the proportion of the molecular species of the triacylglycerols during heating; there was an increase in the more saturated species, 1–4 double bonds, and a decrease in species containing 5–7 double bonds. Although these changes occurred in the percentage of each triacylglycerol species, the positional distribution of the fatty acids in the 2-position remained virtually unchanged throughout heating. Oleic and linoleic acids were commonly found in the 2-position of the acylglycerol moiety, whereas most of the palmitic and stearic acids favored esterification in the 1- and 3-positions. The results indicate that unsaturated fatty acids located in the 2-position are protected significantly from thermal oxidative decomposition.
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References
Brockerhoff, H., and Yurkowski, M. (1966) J. Lipid Res. 7, 62–64.
Lindgvist, B.; Sjogren, I.; and Nordin, R. (1974) J. Lipid Res. 15, 67–73.
Wada, S.; Koizumi, C.; and Nonaka, J. (1977) Yukagaku 26, 95–99.
El-Hamdy, A.H.; and Perkins, E.G. (1981) J. Am. Oil Chem. Soc. 58, 867–872.
Petersson, B.; Podlaha, O.; and Toregard, B. (1981) J. Am. Oil Chem. Soc. 58, 1005–1009.
Langstraat, A. (1976) J. Am. Oil Chem. Soc. 53, 241–247.
Industry News, (1980) J. Am. Oil Chem. Soc. 57, 264A-268A.
Akiya, T., and Shimizu, T. (1965) Yukagaku 14, 520–522.
Poling, C.E.; Warner, W.D.; Mone, P.E.; and Rice, E.E. (1962) J. Am. Oil Chem. Soc. 39, 315–320.
Alexander, J.C. (1978) J. Am. Oil Chem. Soc. 55, 711–717.
Alexander, J.C. (1981) J. Toxicol. Environ, Health 7, 125–138.
Kawada, K.; Krishnamurthy, R.G.; Mookherjee, B.D.; and Chang, S.S. (1967) J. Am. Oil Chem. Soc. 44, 131–135.
Chang, S.S.; Peterson, R.T.; and Ho, C.-T. (1978) J. Am. Oil Chem. Soc. 55, 718–727.
Artman, N.R. (1969) in Advances in Lipid Research (Paoletti, R. and Kritchevsky, D., eds) Vol. 7, pp. 245–330, Academic Press Inc., New York, NY.
Perkins, E.G., and Wantland, L.R. (1973) J. Am. Oil Chem. Soc. 50, 459–461.
Waltking, A.E.; Serry, W.E.; and Bleffert, G.W. (1975) J. Am. Oil Chem. Soc. 52, 96–100.
Come, N.; Constantin, M.I.; and Emtressangles, B. (1981) Lipids 16, 8–16.
Paulose, M.M., and Chang, S.S. (1973) J. Am. Oil Chem. Soc. 50, 147–154.
Meltzer, J.B.; Frankel, E.N.; Bessler, T.R.; and Perkins, E.G. (1981) J. Am. Oil Chem. Soc. 58, 779–784.
Yoshida, H., and Alexander, J.C. (1982) Nutr. Rep. Int. 26, 655–665.
Renkonen, O. (1961) Biochem. Biophys. Acta 54, 361–362.
Billek, G.; Guhr, G.; and Waibel, J. (1978) J. Am. Oil Chem. Soc. 55, 728–733.
de la Roche, I.A.; Weber, E.J.; and Alexander, D.E. (1971) Lipids 6, 537–540.
Blank, M.L.; Verdino, B.; and Privett, O.S. (1965) J. Am. Oil Chem. Soc. 42, 87–90.
Morrison, W.R., and Smith, L.M. (1964) J. Lipid Res. 5, 600–608.
Mattson, F.H., and Volpenhein, R.A. (1961) J. Lipid Res. 2, 58–62.
Privett, O.S., and Nutter, L.J. (1967) Lipids 2, 149–154.
Raghuveer, K.G., and Hammond, E.G. (1967) J. Am. Oil Chem. Soc. 44, 239–243.
Catalano, M.; de Felice, M.; and Sciancalepore, V. (1975) Ind. Aliment. (Pinerolo, Italy) 14, 89–92.
Fatemi, S.H., and Hammond, E.G. (1980) Lipids 15, 379–385.b
Frankel, E.N.; Evans, C.D.; and Cowan, J.C. (1960) J. Am. Oil Chem. Soc. 37, 418–424.
Perkins, E.G. (1967) Food Technol. 21, 611–616.
Selke, E.; Frankel, E.N.; and Neff, W.E. (1978) Lipids 13, 511–513.
Waltking, A.E., and Zmachinski, H. (1970) J. Am. Oil Chem. Soc. 47, 530–534.
Holman, R.T., and Elmer, O.C. (1947) J. Am. Oil Chem. Soc. 24, 127–129.
Wada, S., and Koizumi, C. (1983) J. Am. Oil Chem. Soc. 60, 1105–1109.
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An erratum to this article is available at http://dx.doi.org/10.1007/BF02534733.
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Yoshida, H., Alexander, J.C. Changes in the structure of soybean triacylglycerols due to heat. Lipids 19, 589–593 (1984). https://doi.org/10.1007/BF02534716
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DOI: https://doi.org/10.1007/BF02534716