Skip to main content
Log in

Analysis of cyclopropenoid and cyclopropanoid acids in fats and oils

  • Technical
  • Symposium: Analysis Of Unusual And Minor Constituents, Part II
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

The analysis of cyclopropenoid acids may be considered, from a historical standpoint, to have started with the discovery of the Halphen test. Although this test as orginally conceived was utilized as a means of detecting adulteration of premium edible oils with cottonseed oil, it has since been shown to be a characteristic test for cyclopropenoid fatty acids and has been adapted with various modifications as a quantitative colorimetric test for these substances. More recently, spectrophotometric methods particularly in the IR region have been applied to the analysis of these substances. The 9.8 µ band, characteristic of the cyclopropane, and the 9.91 µ band, characteristic of the cyclopropene group, as well as the 11.0 µ band, characteristic of some of the noncyclic degradation derivatives, have been utilized. Gasliquid chromatography (GLC) has been applied to the methyl esters of cyclopropanoid and hydrogenated cyclopropenoid acids. The reactivity of the cyclopropene ring toward hydrohalogens has been the basis of several analytical methods developed for use with cyclopropene acid-containing oils. Both aqueous and nonaqueous solutions of hydrohalogens have been employed. The hydrohalogenation methods are the most precise methods currently available for these analyses but only GLC has the inherent potential of identifying the specific cyclopropenoid or cyclopropenoids involved.

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. Bailey, A. V., G. Boudreaux and E. L. Skau, unpublished data.

  2. Bailey, A. V., F. C. Magne, G. J. Boudreaux and E. L. Skau, JAOCS40, 69 (1963).

    CAS  Google Scholar 

  3. Bailey, A. V., F. C. Magne, R. A. Pittman and E. L. Skau, JAOCS38, 505 (1961).

    CAS  Google Scholar 

  4. Bailey, A. V., R. A. Pittman, F. C. Magne and E. L. Skau, JAOCS in press.

  5. Cornelius, J. A., and G. Shone, Chem. & Ind. (London) 1246 (1963).

  6. Dasler, W., and C. D. Bauer, Ind. Eng. Chem. Anal. Ed.18, 52, (1946).

    Article  CAS  Google Scholar 

  7. Derfer, J. M., E. E. Pickett and C. E. Boord, J. Am. Chem. Soc.71, 2482 (1949).

    Article  CAS  Google Scholar 

  8. Deutschman, A. J., and I. S. Klaus, Anal. Chem.32, 1809 (1960).

    Article  CAS  Google Scholar 

  9. Dijkstra, G., and H. J. Duin, Nature176, 71 (1955).

    Article  CAS  Google Scholar 

  10. Durbetaki, A. J., Anal. Chem.28, 2000 (1956).

    Article  CAS  Google Scholar 

  11. Earle, F. R., C. A. Glass, G. C. Geisinger, I. A. Wolff and Q. Jones, JAOCS37, 440 (1960).

    CAS  Google Scholar 

  12. Earle, F. R., and Q. Jones, Econ. Botany16, 221 (1962).

    CAS  Google Scholar 

  13. Earle, F. R., E. H. Melvin, L. H. Masson, C. H. Van Etten and I. A. Wolff, JAOCS36, 304 (1959).

    CAS  Google Scholar 

  14. Elsdon, G. D., “Edible Oils and Fats,” Ernest Benn, Ltd., London, 1926, pp. 79–80.

    Google Scholar 

  15. Faure, P. K., Nature178, 372 (1956).

    Article  CAS  Google Scholar 

  16. Fawcett, R. F., J. C. Smith, Chem. & Ind. (London) 871 (1960).

  17. Fichter, M., Pharm. Acta Helv.13, 123 (1938).

    CAS  Google Scholar 

  18. Gastaldi, E., J. Soc. Chem. Ind.31, 934 (1912).

    Google Scholar 

  19. Gaylord, N. G., “Reduction With Complex Metal Hydrides,” Interscience Publishers, Inc., New York, 1956, pp. 420–438.

    Google Scholar 

  20. Halphen, G., J. Pharm.6, 390 (1897); Analyst22, 326 (1898).

    Google Scholar 

  21. Harris, J. A., F. C. Magne and E. L. Skau, JAOCS40, 718 (1963).

    CAS  Google Scholar 

  22. Harris, J. A., F. C. Magne and E. L. Skau, JAOCS41, 309 (1964).

    CAS  Google Scholar 

  23. Harris, J. A., F. C. Magne and E. L. Skau, unpublished.

  24. Hofmann, K., O. Jucker, W. Miller, A. C. Young, Jr., and F. Tausig, J. Am. Chem. Soc.76, 1799 (1954).

    Article  CAS  Google Scholar 

  25. Hofmann, K., and R. A. Lucas, J. Am. Chem. Soc.72, 4328 (1950).

    Article  CAS  Google Scholar 

  26. Hopkins, C. Y., JAOCS38, 664 (1961).

    CAS  Google Scholar 

  27. Hopkins, C. Y., and M. J. Chisholm, JAOCS37, 682 (1960).

    CAS  Google Scholar 

  28. Jamieson, G. S., “Vegetable Fats and Oils,” 2nd Ed., Reinhold Publishing Corp., New York, 1943, pp. 419–420.

    Google Scholar 

  29. Kartha, A. R. S., and J. V. Ojha, Indian J. Chem.1, 51 (1963).

    CAS  Google Scholar 

  30. Kühn, B., and F. Bengen, Z. Nahr. Genussm.12, 145 (1906).

    Google Scholar 

  31. Masson, J. C., Thesis, “Chemical and Biological Effects of Sterculic and Analogous Fatty Acids,” University of Arizona, Tucson, Arizona, 1959.

    Google Scholar 

  32. Masson, J. C., M. G. Vavich, B. W. Heywang and A. R. Kemmerer, Science126, 751 (1957).

    Article  CAS  Google Scholar 

  33. Macfarlane, J. J., F. S. Shenstone, and J. R. Vickery, Nature179, 830 (1957).

    Article  CAS  Google Scholar 

  34. Magne, F. C., A. V. Bailey, E. R. McCall, S. H. Miles and E. L. Skau, Anal. Chem.36, 681 (1964).

    Article  CAS  Google Scholar 

  35. Magne, F. C., J. A. Harris and E. L. Skau, JAOCS40, 716 (1963).

    CAS  Google Scholar 

  36. Mehlenbacker, V. C., Chem. Eng. News22, 606 (1944).

    Google Scholar 

  37. Nordby, H. E., B. W. Heywang, H. W. Kircher and A. R. Kemmerer, JAOCS39, 183 (1962).

    CAS  Google Scholar 

  38. Nunn, J. R., J. Chem. Soc.1952, 313.

  39. Official and Tentative Methods of the American Oil Chemists’ Society, 2nd. ed. rev. to 1962, Method Ca 9f-57.

  40. Ibid., Method Cb 1-25.

  41. Rinehart, K. L., Jr., S. I. Goldberg, C. L. Tarimu and T. P. Culbertson, J. Am. Chem. Soc.83, 225 (1961).

    Article  CAS  Google Scholar 

  42. Shenstone, F. S., and J. R. Vickery, Nature177, 94 (1956).

    Article  CAS  Google Scholar 

  43. Shenstone, F. S., and J. R. Vickery, Nature190, 168 (1961).

    Article  CAS  Google Scholar 

  44. Smith, C. R., Jr., M. C. Burnett, T. L. Wilson, R. L. Lohmar and I. A. Wolff, JAOCS37, 320 (1960).

    CAS  Google Scholar 

  45. Smith, C. R., Jr., T. L. Wilson and K. L. Mikolajczak, Chem. & Ind. (London)1961, 256.

  46. Swift, C. E., W. G. Rose and G. S. Jamieson, Oil and Soap20, 249 (1943).

    CAS  Google Scholar 

  47. Varma, J. P., S. Dasgupta, B. Nath and J. S. Aggarwal, JAOCS34, 452 (1957).

    CAS  Google Scholar 

  48. Wilson, T. L., C. R. Smith, Jr., and K. L. Mikolajczak, JAOCS38, 696 (1961).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

So. Utiliz. Res. Dev. Div., ARS, USDA.

About this article

Cite this article

Magne, F.C. Analysis of cyclopropenoid and cyclopropanoid acids in fats and oils. J Am Oil Chem Soc 42, 332–336 (1965). https://doi.org/10.1007/BF02540141

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02540141

Keywords

Navigation