Abstract
When linoleic acid or its esters were heated in the presence of valine a number of interaction products were formed. The major product was 2-pentylpyridine which is thought to be produced by the reaction of 2,4-decadienal with ammonia. Also formed were two secondary amides, isobutyloctanamide and isobutyllinoleylamide. Additional interaction products found include alkylpyridines and alkylpyrroles. The formation of these compounds is similar to the formation of 2-pentylpyridine. They can result by reaction of an aldehyde with an amine or ammonia to form a Schiff base intermediate, followed by cyclization and rearrangement to form either the pyridine ring or the pyrrole ring. In addition, a branched nitrile compound was produced. This compound is considered to be formed by cleavage of the pyridine ring in 2-pentylpyridine.
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References
Nawar, W.W., J.R. Champagne, M.F. Dubravcic and P.R. LeTellier, J. Agric. Food Chem. 17:645 (1969).
Metcalfe, L.D., and A.A. Schmitz, Anal. Chem. 33:363 (1961).
Budzikiewicz, H., C. Djerassi, A.H. Jackson, G.W. Kenner, D.J. Newman and J.M. Wilson, J. Chem. Soc. 89:1949 (1964).
Duffield, A.M., H. Budzikiewicz, D.H. Williams and C. Djerassi, J. Am. Chem. Soc. 87:810 (1965).
Porter, Q.N., and J. Baldas, “Mass Spectrometry of Heterocyclic Compounds,” Wiley Interscience, New York, NY, 1971, pp. 310, 331, 376–384.
Millar, I.I., and H.D. Springall, “The Organic Chemistry of Nitrogen,” Clarendon Press, Oxford, 1966, pp. 619–637, 667–696.
Fischer, H., and E. Bartholomaus, S. Physiol. Chem. 77:185 (1912); Chem. Abs. 2068, (1912).
Spiteller, G., in “Advances in Heterocyclic Chemistry,” Vol. 7, 1966, pp. 317–319.
Gilpin, J.A., Anal. Chem. 31:935 (1959).
Sims, R.J., and J.R. Fioriti, JAOCS 52:144 (1975).
Lien, Y.C., and W.W. Nawar, J. Food Sci. 39:911 (1974).
Gohlke, R.S. and F.W. McLafferty, Anal. Chem. 34:1281 (1962).
Mooher, H.S., in “Heterocyclic Compounds,” Vol. 1, edited by R.C. Elderfield, John Wiley and Sons, Inc., New York, NY, 1950, pp. 397–616.
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Henderson, S.K., Nawar, W.W. Thermal interaction of linoleic acid and its esters with valine. J Am Oil Chem Soc 58, 632–635 (1981). https://doi.org/10.1007/BF02672381
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DOI: https://doi.org/10.1007/BF02672381