Abstract
Four compounds were isolated from the acidic fraction of 1-linoleyl-2,3-distearin which was heated at 200 C for 24 hr with aeration. Following saponification of the oxidation mixture, the fatty acids were partitioned between ethanol and pentane-hexane (Skellysolve F). The ethanol soluble acids were subsequently esterified with methanol and subjected to further separation by preparative thin layer and gas liquid chromatography. A combination of chemical and instrumental analyses as well as a comparison with standard compounds was used to determine the structures. Substances characterized were isomeric C18 aromatic esters, isomeric methyl keto-octadecanoates, isomeric methyl keto-octadecenoates and dimethyl undecane-1,11-dioate.
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References
Endres, J. G., V. R. Bhalerao and F. A. Kummerow, JAOCS 39:118 (1962).
Endres, J. G., V. R. Bhalerao and F. A. Kummerow, Ibid. 39:159 (1962).
Crossley, A., T. D. Heyes and B. J. F. Hudson, Ibid. 39:9 (1962).
Wantland, L. R., and E. G. Perkins, in press.
Perkins, E. G., JAOCS 44:197 (1967).
Stahl, E., Chemiker Ztg. 82:323 (1958).
Wood, R., and R. Reiser, JAOCS 42:159 (1965).
Miwa, T. K., Ibid. 40:309 (1963).
Brown, C., Anal. Chem. 39:1882 (1967).
Vogel, A. I. in “A Text Book of Practical Organic Chemistry,” John Wiley, New York, 1962, p. 520.
Argoudelis, C. J., and E. G. Perkins, Lipids 3:379 (1968).
Schneider, F. L., “Quantitative Organic Microanalysis, Cognition and Recognition of Carbon Compounds,” Academic Press, New York, 1964, p. 182–184.
Nichols, J., and E. Schipper, J. Am. Chem. Soc. 80:5705 (1958).
Bellamy, L. J., “The Infrared Spectra of Complex Molecules,” John Wiley, New York, 1958, p. 65.
Tunnicliff, D., R. R. Brattain and L. R. Zumwalt, Anal. Chem. 21:891 (1949).
American Petroleum Institute, Research Project, No. 44, Spectra No. 63, 71, 123 and 194, Carnegie Institute of Technology, Pittsburgh, 1947.
McLafferty, F. W., “Interpretation of Mass Spectra,” W. A. Benjamin, New York, 1966, p. 212–214.
Michael, W. R., Lipids 1:359 (1966).
Barrett, C. B., M. S. J. Dallas and F. B. Padley, JAOCS 40:580 (1963).
Stenhagen, E., in “Analysis and Characterization of Oils, Fats and Fat Products”, Vol. 2, Edited by H. A. Boekenoogen, Interscience Publishers, New York, 1968, p. 22ff.
Ryhage, R., and E. Stenhagen, in “Mass Spectrometry of Organic Ions,” Edited by F. W. McLafferty, Academic Press, New York, 1963, p. 446.
Ryhage, R., and E. Stenhagen, Ibid. in “, p. 430–432.
Keeney, M., in “Symposium on Foods: Lipids and Their Oxidation,” Edited by H. W. Schultz, E. A. Day and R. O. Sinnhuber, The Avi Publishing Co., Westport, Conn., 1962, p. 80.
Artman, N. R., and J. C. Alexander, JAOCS 45:643 (1968).
Ryhage, R., S. Stallberg-Stenhagen and E. Stenhagen, Arkiv Kemi 18:179 (1959).
Gunstone, F. D., “An Introduction to the Chemistry of Fats and Fatty Acids,” Chapman and Hall, London, 1958, p. 120.
Miwa, T. K., K. L. Mikolajczak, F. R. Earle and I. A. Wolff, Anal. Chem. 32:1739 (1960).
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This work represents a portion of a thesis presented by L. R. Wantland as partial fulfillment of the requirements for the Ph.D. degree at the University of Illinois.
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Wantland, L.R., Perkins, E.G. Characterization of the nonvolatile compounds formed during the thermal oxidation of 1-linoleyl-2,3-distearin: II. The acidic fraction. Lipids 5, 191–200 (1970). https://doi.org/10.1007/BF02532468
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DOI: https://doi.org/10.1007/BF02532468