Abstract
Monocarbonyl compounds formed by the decomposition of autoxidized triolein, methyl linolenate, and methyl arachidonate were converted into their 2,4-dinitrophenylhydrazone derivatives and analyzed by thin layer and paper chromatographies. From decomposition of autoxidized triolein with acid-washed Fuller’s earth alkanals were the only monocarbonyl products found, whereas, with metal catalysts or heat, 2-alkenals were the primary products. Autoxidized methyl linolenate and methyl arachidonate decomposed with metal catalysts or heat yielded 23–55% of 2,4-alkadienals but minor amounts with acid-washed Fuller’s earth. The differences in distribution of monocarbonyl products were attributed to a selective course of scission of the hydroperoxides that depended upon the conditions of decomposition.
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References
Ellis, R., A.M. Gaddis, G.T. Currie, and S.L. Powell, JAOCS 45:553 (1968).
Ellis, R., A.M. Gaddis, and G.T. Currie, J. Food Sci. 31:191 (1966).
Dolev, A., W.K. Rohwedder, and H.J. Dutton, Lipids 2:28 (1967).
Frankel, E.N., C.D. Evans, D.G. McConnell, E. Selke, and H.J. Dutton, J. Org. Chem. 26:4663 (1961).
Kimoto, W.I., and A.M. Gaddis, JAOCS 46:403 (1969).
Schwartz, D.P., H.S. Haller, and M. Keeney, Anal. Chem. 35:2191 (1963).
Gaddis, A.M., and R. Ellis, Ibid. 31:870 (1959).
Hammond, E.G., and F.D. Hill, JAOCS 41:180 (1964).
Smith, P.A.S., in “Molecular Rearrangements,” Part 1, Edited by P. DeMayo, Interscience Publishers, New York, N.Y., 1963, pp. 568–577.
Hiatt, R., in “Organic Peroxides,” Vol. 2, Edited by D. Swern, Wiley-Interscience, New York, N.Y., 1971, 67–71.
Hiatt, R., K.C. Irwin, and C.W. Gould, J. Org. Chem. 33:1430 (1968).
Hiatt, R., and K.C. Irwin, Ibid. 33:1436 (1968).
Privett, O.S., and E.C. Nickell, Fette Seifen Anstrichm. 61:842 (1959).
Farmer, E.H., and D.A. Sutton, J. Chem. Soc. (London), 119 (1943).
Walling, C., in “Molecular Rearrangements,” Part 1, Edited by P. DeMayo, Interscience Publishers, New York, N.Y., 1963, pp. 407–431.
Greene, F.D., M.L. Savitz, F.D. Osterholtz, H.H. Lau, W.N. Smith, and P.M. Zanet, J. Org. Chem. 28:55 (1963).
Walling, C., and A. Padwa, J. Amer. Chem. Soc. 85:1593 (1963).
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Kimoto, W.I., Gaddis, A.M. Monocarbonyl compounds from catalytic decomposition of autoxidized unsaturated fatty acid esters. J Am Oil Chem Soc 51, 307–311 (1974). https://doi.org/10.1007/BF02633003
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DOI: https://doi.org/10.1007/BF02633003