Abstract
Important factors and new techniques in the application of ozonolysis to the localization of double bond positions in unsaturated fatty acids are elaborated. Solvent polarity was shown to exert a profound influence on the yield and composition of ozonides. The influence of fatty acid structure on ozonide formation and the thin-layer chromatography (TLC) of ozonides of a number of different types of unsaturated fatty acids are illustrated. Simple methods for the ozonization of unsaturated fatty acid esters and the cleavage of ozonides by reduction and pyrolysis are described. Applications of ozonolysis to the determination of the structures of geometric isomers, hydroxy, epoxy and cyclic olefinic fatty acids, and the localization of radioactivity along the chain of unsaturated fatty acids are illustrated.
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References
Benton, F. D., A. A. Kiess and H. S. Harwood, JAOCS36, 457 (1959).
Harwood, H. J., Chem. Rev.62, 99 (1962).
Young, W. G., A. C. McKinnis, I. D. Webb and J. D. Roberts, J. Am. Chem. Soc.68, 293 (1946).
Tullock, A. P., and B. M. Craig, JAOCS41, 322 (1964).
Jones, E. P., and V. L. Davison, Ibid.42, 121 (1965).
Criegee, R., Record Chem. Progr.18, 111 (1957).
Privett, O. S., and E. C. Nickell, JAOCS41, 72 (1964).
Milas, N. A., “The Chemistry of Petroleum Hydrocarbons,” Vol. 2. Reinhold Publishing Corporation, New York, 1955, p. 399.
Criegee, R., “Peroxide Reaction Mechanisms,” Interscience Publishers, Inc., New York, 1960, pp. 29–39.
Bailey, P. S., S. B. Mianthia and C. S. Abshire, J. Am. Chem. Soc.82, 6136 (1960).
Privett, O. S., and E. C. Nickell, J. Lipid Res.4, 208 (1963).
Bailey, P. S., Chem. Rev.58, 925 (1958).
Moore, D. J., E. H. Pryde and J. C. Cowan, JAOCS,42, 893 (1965).
Ackman, R. G., M. E. Retson, L. R. Gallay and F. A. Vandenheuvel, Can. J. Chem.39, 1956 (1961).
Riezebos, G., J. C. Grimmelikhuysen and D. A. Van Dorp, Rec. trav. chim.82, 1234 (1963).
Privett, O. S., and E. C. Nickell, JAOCS39, 414 (1962).
Schlenk, H., and J. L. Gellerman, Ibid.42, 504 (1965).
Whitcutt, J. H., and D. A. Sutton, Biochem. J.63, 469 (1956).
Stoffel, W., JAOCS42, 583, (1965).
Klenk, E., and W. Bongard, Z. physiol. Chem.290, 181 (1952).
Klenk, E., and G. Kremer, Ibid.320, 111 (1960).
Bonner, W. A., J. Chem. Educ.30, 452 (1953).
Privett, O. S., M. L. Blank, D. W. Codding, and E. C. Nickell, JAOCS42, 381 (1965).
Hoagman, P. W., and J. P. Wibault, Rec. trav. chim.60, 842 (1941).
Nickell, E. C., and O. S. Privett, Paper No. 80, “A Simple Micromethod for the Determination of the Structure of Unsaturated Fatty Acids Via Ozonolysis,” American Oil Chemists' Society Meeting, Clincinnati, 1965.
Tullock, A. T., and B. M. Craig, JAOCS41, 322 (1964).
Jones, E. P., and V. L. Davison, Ibid.42, 121 (1965).
Stein, R. A., and N. Nicolaides, J. Lipid Res.3, 476 (1962).
Privett, O. S., M. L. Blank and O. Romanus, Ibid.4, 260 (1963).
Urbach, G., J. Chromatog.12, 196 (1963).
Privett, O. S., and E. C. Nickell, “Determination of the Specific Positions ofcis andtrans Double bonds in Polyene,” JAOCS, in press.
Lindlar, H., Helv. Chim. Acta35, 446 (1964).
Stoll, M., and A. Rouve, Ibid.27, 950 (1944).
Briner, E., Ibid.22, 591 (1939).
Briner, E., and R. Meier, Ibid.,12, 529 (1929).
Pasero, J., L. Comeau and M. Naudet, Bull soc. chim. 1794 (1963); 493 (1965).
Davison, V. L., and H. J. Dutton, Paper No. 87A, “Simplified Micro-ozonolysis Procedures for the Quantitative Determination of Double Bond Positions,” American Oil Chemists' Society Meeting, Cincinnati, 1965.
Nickell, E. C., and O. S. Privett, unpublished data.
Gunstone, F. D., and P. J. Sykes, J. Chem. Soc. 3058 (1962).
deJong, K., IFS Meeting, London, 1962.
deVries, B., Chem. Ind. (London) 1049 (1962).
Morris, L. J., Ibid. Chem. Ind. (London) 1238 (1962).
Scholfield, C. R., O. Butterfield and H. S. Dutton, Abstract No. 5, Division of Agricultural and Food Chemistry, ACS Meeting, Chicago, 1964.
Hopkins, C. Y., and M. J. Chisholm, J. Chem. Soc. 907 (1965).
Mikolajczak, K. L., and M. O. Bagby, JAOCS42, 43 (1965).
Dauben, W. G., E. Hoerger and J. W. Petersen, J. Am. Chem. Soc.75, 2347 (1953).
Stearns, E., and F. W. Quackenbush, Paper No. 37, “Radioactivity of Individual Carbons in the Chains of Unsaturated Acids From the Soybean,” AOCS Meeting Chicago, 1964.
Showell, J. S., and I. S. Shepherd, Paper No. 97, “The Perchloric Acid Isomerization of Monoethylenic Compound,” AOCS Meeting, Houston, 1965.
Gunstone, F. D., J. Chem. Soc. 1611 (1954).
Gunstone, F. D., and L. J. Morris, Ibid. J. Chem. Soc. 2127, (1959).
Gunstone, F. D., and W. C. Russell, Ibid. J. Chem. Soc. 3782 (1955).
Borka, L., and O. S. Privett, unpublished data. The Hormel Institute, University of Minnesota. Austin, Minnesota.
Nickell, E. C., and O. S. Privett, Paper No. 55, “Studies on the Ozonization of Sterculinecis andtrans-9-Octadecene,” AOCS Meeting, Chicago, 1964.
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Privett, O.S., Nickell, E.C. Recent advances in the determination of the structure of fatty acids via ozonolysis. J Am Oil Chem Soc 43, 393–400 (1966). https://doi.org/10.1007/BF02646797
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DOI: https://doi.org/10.1007/BF02646797