Skip to main content
Log in

Recent advances in the determination of the structure of fatty acids via ozonolysis

  • Technical
  • Published:
Journal of the American Oil Chemists Society

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Benton, F. D., A. A. Kiess and H. S. Harwood, JAOCS36, 457 (1959).

    Article  CAS  Google Scholar 

  2. Harwood, H. J., Chem. Rev.62, 99 (1962).

    Article  CAS  Google Scholar 

  3. Young, W. G., A. C. McKinnis, I. D. Webb and J. D. Roberts, J. Am. Chem. Soc.68, 293 (1946).

    Article  CAS  Google Scholar 

  4. Tullock, A. P., and B. M. Craig, JAOCS41, 322 (1964).

    Google Scholar 

  5. Jones, E. P., and V. L. Davison, Ibid.42, 121 (1965).

    Article  CAS  Google Scholar 

  6. Criegee, R., Record Chem. Progr.18, 111 (1957).

    CAS  Google Scholar 

  7. Privett, O. S., and E. C. Nickell, JAOCS41, 72 (1964).

    CAS  Google Scholar 

  8. Milas, N. A., “The Chemistry of Petroleum Hydrocarbons,” Vol. 2. Reinhold Publishing Corporation, New York, 1955, p. 399.

    Google Scholar 

  9. Criegee, R., “Peroxide Reaction Mechanisms,” Interscience Publishers, Inc., New York, 1960, pp. 29–39.

    Google Scholar 

  10. Bailey, P. S., S. B. Mianthia and C. S. Abshire, J. Am. Chem. Soc.82, 6136 (1960).

    Article  CAS  Google Scholar 

  11. Privett, O. S., and E. C. Nickell, J. Lipid Res.4, 208 (1963).

    CAS  Google Scholar 

  12. Bailey, P. S., Chem. Rev.58, 925 (1958).

    Article  CAS  Google Scholar 

  13. Moore, D. J., E. H. Pryde and J. C. Cowan, JAOCS,42, 893 (1965).

    Article  Google Scholar 

  14. Ackman, R. G., M. E. Retson, L. R. Gallay and F. A. Vandenheuvel, Can. J. Chem.39, 1956 (1961).

    Article  CAS  Google Scholar 

  15. Riezebos, G., J. C. Grimmelikhuysen and D. A. Van Dorp, Rec. trav. chim.82, 1234 (1963).

    Article  CAS  Google Scholar 

  16. Privett, O. S., and E. C. Nickell, JAOCS39, 414 (1962).

    Article  CAS  Google Scholar 

  17. Schlenk, H., and J. L. Gellerman, Ibid.42, 504 (1965).

    Article  CAS  Google Scholar 

  18. Whitcutt, J. H., and D. A. Sutton, Biochem. J.63, 469 (1956).

    CAS  Google Scholar 

  19. Stoffel, W., JAOCS42, 583, (1965).

    Article  CAS  Google Scholar 

  20. Klenk, E., and W. Bongard, Z. physiol. Chem.290, 181 (1952).

    CAS  Google Scholar 

  21. Klenk, E., and G. Kremer, Ibid.320, 111 (1960).

    CAS  Google Scholar 

  22. Bonner, W. A., J. Chem. Educ.30, 452 (1953).

    Article  CAS  Google Scholar 

  23. Privett, O. S., M. L. Blank, D. W. Codding, and E. C. Nickell, JAOCS42, 381 (1965).

    Article  CAS  Google Scholar 

  24. Hoagman, P. W., and J. P. Wibault, Rec. trav. chim.60, 842 (1941).

    Google Scholar 

  25. 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.

  26. Tullock, A. T., and B. M. Craig, JAOCS41, 322 (1964).

    Google Scholar 

  27. Jones, E. P., and V. L. Davison, Ibid.42, 121 (1965).

    Article  CAS  Google Scholar 

  28. Stein, R. A., and N. Nicolaides, J. Lipid Res.3, 476 (1962).

    CAS  Google Scholar 

  29. Privett, O. S., M. L. Blank and O. Romanus, Ibid.4, 260 (1963).

    CAS  Google Scholar 

  30. Urbach, G., J. Chromatog.12, 196 (1963).

    Article  CAS  Google Scholar 

  31. Privett, O. S., and E. C. Nickell, “Determination of the Specific Positions ofcis andtrans Double bonds in Polyene,” JAOCS, in press.

  32. Lindlar, H., Helv. Chim. Acta35, 446 (1964).

    Article  Google Scholar 

  33. Stoll, M., and A. Rouve, Ibid.27, 950 (1944).

    Article  CAS  Google Scholar 

  34. Briner, E., Ibid.22, 591 (1939).

    Article  CAS  Google Scholar 

  35. Briner, E., and R. Meier, Ibid.,12, 529 (1929).

    Article  CAS  Google Scholar 

  36. Pasero, J., L. Comeau and M. Naudet, Bull soc. chim. 1794 (1963); 493 (1965).

    Google Scholar 

  37. 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.

  38. Nickell, E. C., and O. S. Privett, unpublished data.

  39. Gunstone, F. D., and P. J. Sykes, J. Chem. Soc. 3058 (1962).

  40. deJong, K., IFS Meeting, London, 1962.

  41. deVries, B., Chem. Ind. (London) 1049 (1962).

  42. Morris, L. J., Ibid. Chem. Ind. (London) 1238 (1962).

  43. Scholfield, C. R., O. Butterfield and H. S. Dutton, Abstract No. 5, Division of Agricultural and Food Chemistry, ACS Meeting, Chicago, 1964.

  44. Hopkins, C. Y., and M. J. Chisholm, J. Chem. Soc. 907 (1965).

  45. Mikolajczak, K. L., and M. O. Bagby, JAOCS42, 43 (1965).

    Article  CAS  Google Scholar 

  46. Dauben, W. G., E. Hoerger and J. W. Petersen, J. Am. Chem. Soc.75, 2347 (1953).

    Article  CAS  Google Scholar 

  47. 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.

  48. Showell, J. S., and I. S. Shepherd, Paper No. 97, “The Perchloric Acid Isomerization of Monoethylenic Compound,” AOCS Meeting, Houston, 1965.

  49. Gunstone, F. D., J. Chem. Soc. 1611 (1954).

  50. Gunstone, F. D., and L. J. Morris, Ibid. J. Chem. Soc. 2127, (1959).

  51. Gunstone, F. D., and W. C. Russell, Ibid. J. Chem. Soc. 3782 (1955).

  52. Borka, L., and O. S. Privett, unpublished data. The Hormel Institute, University of Minnesota. Austin, Minnesota.

  53. Nickell, E. C., and O. S. Privett, Paper No. 55, “Studies on the Ozonization of Sterculinecis andtrans-9-Octadecene,” AOCS Meeting, Chicago, 1964.

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

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

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02646797

Keywords

Navigation