Skip to main content
SpringerLink
Log in

The analysis ofCis-trans fatty acid isomers using gas-liquid chromatography

  • Technical
  • Symposium on Methodology of Fats and Oils Conducted by The American Oil Chemists’ Society at Its 53rd Annual Meeting, New Orleans, Louisiana May 8–9, 1962 Raymond Reiser, Presiding R. T. O’Connor, Program Chairam Part II
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

The geometric isomers of many unsaturated fatty acid methyl esters can be separated using high-resolution gas-liquid chromatography on polyester or Apiezon columns. Separations reported for the geometric isomers of monounsaturated, ricinoleic, linoleic, conjugated, and epoxy fatty acids are reviewed here. New data is presented on the resolution of linolenate geometric isomers on both polyester and Apiezon columns. The separation of methyl oleate and methyl elaidate on a polyester column has also been accomplished. Techniques for preparing and using the high-resolution columns necessary for these separations are reviewed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. James, A. T., and A. J. P. Martin, Biochem. J.63, 144 (1956).

    CAS  Google Scholar 

  2. Lipsky, S. R., J. E. Lovelock, and R. A. Landowne, J. Am. Chem. Soc.81, 1010 (1959).

    Article  CAS  Google Scholar 

  3. Lipsky, S. R., R. A. Landowne, and J. E. Lovelock, Anal. Chem.31, 852 (1959).

    Article  CAS  Google Scholar 

  4. Kauffman, F. L., and G. D. Lee, JAOCS37, 385 (1960).

    Article  CAS  Google Scholar 

  5. Litchfield, C., A. F. Isbell, and R. Reiser,Ibid., 39, 330 (1962).

    Article  CAS  Google Scholar 

  6. Beerthuis, R. K., G. Dijkstra, J. G. Keppler, and J. H. Recourt, Ann. N. Y. Acad. Sci.72, 616 (1959).

    Article  CAS  Google Scholar 

  7. Keppler, J. G. in Devine, J., and P. N. Williams, “The Chemistry and Technology of Edible Oils and Fats,” Pergamon Press, New York, 1961, pp. 91–92.

    Google Scholar 

  8. Morris, L. J., R. T. Holman, and K. Fontell, J. Lipid Research1, 412 (1960).

    CAS  Google Scholar 

  9. James, A. T. in Glick, D., “Methods of Biochemical Analysis,” Vol. 8, Interscience, New York, 1960, pp. 1–59.

    Book  Google Scholar 

  10. Landowne, R. A., and S. R. Lipsky, Biochem. Biophys. Acta46, 1 (1961).

    Article  CAS  Google Scholar 

  11. Body, D. R., and F. B. Shorland, Chem. & Ind. …, 1665 (1961).

  12. Miwa, T. K., K. L. Mikolajczak, F. R. Earle, and I. A. Wolff, Anal. Chem.32, 1739 (1960).

    Article  CAS  Google Scholar 

  13. Method Cd-14-61, “IsolatedTrans Isomers,” in “Official and Tentative Methods of the AOCS,” Chicago, 1961.

  14. Scholfield, C. R., E. P. Jones, and H. J. Dutton, Anal. Chem.33, 1745 (1961).

    Article  CAS  Google Scholar 

  15. Sreenivasan, B., J. Nowakowska, E. P. Jones, E. Selke, C. R. Scholfield, and H. J. Dutton, “Hydrogenation of Linolenate. VII. Separation of Isomeric Dienes and Monoenes,” presented at the AOCS meeting in Chicago, 1961.

  16. Morris, L. J., R. T. Holman, and K. Fontell, J. Lipid Research2, 68 (1961).

    CAS  Google Scholar 

  17. James, A. T., Fette, Seifen, Anstrichmittel 59, 73 (1957).

    Article  CAS  Google Scholar 

  18. James, A. T., J. Chrom.2, 552 (1959).

    Article  CAS  Google Scholar 

  19. Farquhar, J. W., J. Lipid Research3, 21 (1962).

    CAS  Google Scholar 

  20. Hoffman, G., and J. G. Keppler, Nature185, 310 (1960).

    Article  Google Scholar 

  21. Hoffman, G., JAOCS38, 31 (1961).

    Article  Google Scholar 

  22. Fieser, L. F., and M. Fieser, “Organic Chemistry,” 3rd edition, D. C. Heath and Co., Boston, 1956, pp. 290–291.

    Google Scholar 

  23. Data taken from original work described elsewhere in this paper.

  24. Litchfield, C., J. E. Lord, A. F. Isbell, and R. Reiser, “Cis-Trans Isomerization of Oleic, Linoleic, and Linolenic Acids,” paper presented at the AOCS meeting in Toronto, Ont., Canada, 1962.

  25. Jackson, J. E., R. F. Paschke, W. Tolberg, H. M. Boyd, and D. H. Wheeler, JAOCS29, 229 (1952).

    Article  CAS  Google Scholar 

  26. Magidman, P., S. F. Herb, R. A. Barford, and R. W. Riemenschneider,Ibid. 39, 137 (1962); Herb, S. F., P. Magidman, F. E. Luddy, and R. W. Riemenschneider,Ibid. JAOCS,39, 142 (1962).

    Article  CAS  Google Scholar 

  27. Manufactured by Crawford Fitting Co., Cleveland 10, Ohio.

  28. Raulin, J., C. Loriette, A. Prevot, C. Defromont, and F. Cabeza, Revue Francaise des Corps Gras9, 75 (1962).

    CAS  Google Scholar 

  29. Stein, R. A.,JAOCS 38, 636 (1961).

    CAS  Google Scholar 

  30. McCutchon, M. A., R. T. O’Connor, E. F. DuPre, L. A. Goldblatt, and W. G. Bickford,Ibid., 36, 115 (1959).

    Article  CAS  Google Scholar 

  31. Rollett, A., Z. Physiol. Chem.62, 422 (1909).

    Google Scholar 

  32. Kass, J. P., and G. O. Burr, J. Amer. Chem. Soc.61, 1062 (1939).

    Article  CAS  Google Scholar 

  33. Kass, J. P., J. Nichols, and G. O. Burr,Ibid. 63, 1060 (1941).

    Article  CAS  Google Scholar 

  34. Kaufmann, H. P., G. Mankel, and K. Lehmann, Fette, Seifen, Anstrichmittel63, 1109 (1961).

    Article  Google Scholar 

  35. Farquhar, J. W., W. Insull, Jr., P. Rosen, W. Stoffel, and E. H. Ahrens, Jr., Nutrition Revs.17, August Supplement (1959).

  36. Kitagawa, I., M. Sugai, and F. A. Kummerow, JAOCS39, 217 (1962).

    Article  CAS  Google Scholar 

  37. Manufactured by Posen and Klein Tube Co., Inc., and Superior Tube Co., Norristown, Pa.

  38. Burchfield, H. P., and E. E. Storrs, “Biochemical Applications of Gas Chromatography,” Academic Press, New York, 1962.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Biochemistry and Nutrition, Texas Agricultural Experiment Station, College Station, Texas

    Carter Litchfield, Raymond Reiser & A. F. Isbell

  2. Department of Chemistry, A & M College of Texas, College Station, Texas

    A. F. Isbell

Authors
  1. Carter Litchfield
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Raymond Reiser
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. F. Isbell
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Supported in part by a grant from the National Institutes of Health (A-6011).

About this article

Cite this article

Litchfield, C., Reiser, R. & Isbell, A.F. The analysis ofCis-trans fatty acid isomers using gas-liquid chromatography. J Am Oil Chem Soc 40, 302–309 (1963). https://doi.org/10.1007/BF02633702

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02633702

Keywords

Search

Navigation