Abstract
Methyl linoleate, diluted with an equal weight of methyl laurate, was heated without exclusion of air at 200C for 200 hours. The reaction mixture was separated by means of molecular distillation, urea adduction, column chromatography, and gas chromatography. Cyclic and aromatic materials were detected in the nonurea adductable monomer fractions. The dimer was separated into polar and nonpolar fractions. Analytical data for the nonpolar dimer are consistent with a cyclic Diels-Alder product. Bioassays showed the nonadductable monomer, the polar dimer, and a fraction of intermediate boiling point to be toxic when administered to weanling male rats. Urea-adductable fractions, nonpolar dimer, and polymer were not toxic. The concentrations of the toxic components were so low that the heated linoleate, before fractionation but after removal of the laurate, was not toxic.
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Crampton, E. W., R. H. Common, F. A. Farmer, A. F. Wells and D. Crawford, J. Nutr.49, 333–346 (1953).
Kaunitz, H., C. A. Slanetz and R. E. Johnson, J. Nutr.55, 577–587 (1955).
Johnson, O. C., T. Sakuragi and F. A. Kummerow, JAOCS33, 433–435 (1956).
Perkins, E. G., and F. A. Kummerow, J. Nutr.68, 101–108 (1959).
Brown, J. B., Nutr. Rev.17, 321–325 (1959).
Perkins, E. G., Food Technol.14, 508–514 (1960).
Friedman, L., W. Horwitz, G. M. Shue and D. Firestone, J. Nutr.73, 85–93 (1961).
MacDonald, J. A., JAOCS33, 394–396 (1956).
Frankel E. N., C. D. Evans, H. A. Moser, D. G. McConnell and J. C. Cowan, JAOCS38, 130–134 (1961).
Hutchison, R. B., and J. C. Alexander, J. Org. Chem.28, 2522–2526 (1963).
Paschke, R. F., L. E. Peterson and D. H. Wheeler, JAOCS41, 723–727 (1964).
Melnick, D., JAOCS34, 351–356, 578–582 (1957).
Melnick, D., F. H. Luckmann and C. M. Gooding, JAOCS35, 271–277 (1958).
Keane, K. W., G. A. Jacobson and C. H. Krieger, J. Nutr.68, 57–74 (1959).
Rice, E. E., C. E. Poling, P. E. Mone and W. D. Warner, JAOCS37, 607–613 (1960).
Poling, C. E., W. D. Warner, P. E. Mone and E. E. Rice, J. Nutr.72, 109–120 (1960).
Poling, C. E., W. D. Warner, P. E. Mone and E. E. Rice, JAOCS39, 315–320 (1962).
Warner, W. D., P. N. Abell, P. E. Mone, C. E. Poling and E. E. Rice, J. Am. Dietet. Assoc.40, 422–426 (1962).
Wilding, M. D., E. E. Rice and K. F. Mattil, JAOCS40, 55–57 (1963).
Kaunitz, H., R. E. Johnson and L. Pegus, JAOCS42, 770–774 (1965).
Raju, N. V., M. N. Rao and R. Rajagopalan, JAOCS42, 774–776 (1965).
Firestone, D., W. Horwitz, L. Friedman and G. M. Shue, JAOCS38, 253–257 (1961).
Hirsch, J., and E. H. Ahrens, Jr., J. Biol. Chem.233, 311–320 (1958).
Kishimoto, Y., and N. S. Radin, J. Lipid Res.1, 72–78 (1959).
de Vries, B., JAOCS40, 184–186 (1963).
de Vries, B., Chem. Ind. (London) (1962) 1049–1051.
Knight, H. B., and D. Swern, JAOCS26, 366–370 (1949).
Mehlenbacher, V. C., “The Analysis of Fats and Oils,” The Garrard Press, Champaign, Illinois, 1960, p 489.
Paschke, R. F., and D. H. Wheeler, JAOCS26, 278–283 (1949).
Paschke R. F., J. E. Jackson and D. H. Wheeler, Ind. Eng. Chem.,44, 1113–1118 (1952).
Mehta, T. N., and S. A. Sharma, JAOCS34, 448–450 (1957).
Kaunitz, H., C. A. Slanetz, R. E. Johnson, H. B. Knight, D. H. Saunders and D. Swern, JAOCS33, 630–634 (1956).
Kaunitz, H., C. A. Slanetz, R. E. Johnson, H. B. Knight, R. E. Koos and D. Swern, JAOCS36, 611–615 (1959).
Kaunitz, H., C. A. Slanetz, R. E. Johnson, H. B. Knight and D. Swern, Metab. Clin. Exptl.9, 59–66 (1960).
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Michael, W.R., Alexander, J.C. & Artman, N.R. Thermal reactions of methyl linoleate. I. Heating conditions, isolation techniques, biological studies and chemical changes. Lipids 1, 353–358 (1966). https://doi.org/10.1007/BF02532680
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DOI: https://doi.org/10.1007/BF02532680