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Epoxy oils from plant seeds

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

Abstract

Epoxy acids have been reported in seed oils from more than 60 species in 12 plant families. The discovery of 9,10-epoxyoctadec-12-ynoic and 9,10-epoxy-trans-3,cis-12-octadecadienoic acids brings to six the number of natural epoxy acids now known to occur in seed oils. These latest epoxy acids and 15,16-epoxy-cis-9,cis-12-octadecadienoic acid have been found in only one species each and at levels lower than 5% of the oil. Coronaric (9,10-epoxy-cis-12-octadecenoic) acid and 9,10-epoxystearic acid have been encountered in several seed oils, the first as much as 15% of the oil and the latter in only small amounts. Vernolic (12,13-epoxy-cis-9-octadecenoic) acid, which has been identified in numerous oils, is the only epoxy acid known to occur in seed oils at levels above 15%, and it may constitute as much as 75%. On the basis of data available to date,Vernonia anthelmintica appears to have the best potential for commercial production of an epoxy oil. Although one improved line has been selected, continued improvement is needed. Formation of epoxy acids in oilseeds during storage after harvest has been demonstrated, and may be partly responsible for the small amounts of epoxide detected in oils from a wide variety of seeds.

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References

  1. Gunstone, F. D., “Fatty Acids and Their Glycerides,” Chapman and Hall, Ltd., London, 1967.

    Google Scholar 

  2. Hilditch, T. P., and P. A. Williams, “The Chemical Constitution of Natural Fats,” 4th Edition, John Wiley & Sons, Inc., New York, 1964.

    Google Scholar 

  3. Markley, K. S., “Fatty Acids,” 2nd Edition, Part 5, Edited by K. S. Markley, Interscience Publishers, New York, 1968.

    Google Scholar 

  4. Smith, C. R., Jr., in “Progress in the Chemistry of Fats and Other Lipids,” Edited by R. T. Holman, Vol. 11, Pergamon Press, Ltd. Oxford, England, 1970, p. 137–177.

    Google Scholar 

  5. Wolff, I. A., Science154, 1140–1149 (1966).

    Article  CAS  ADS  Google Scholar 

  6. Krewson, C. F., JAOCS45, 250–256 (1968).

    CAS  Google Scholar 

  7. Wolff, I. A., and T. K. Miwa, Ibid.42, 208–215 (1965).

    Article  CAS  Google Scholar 

  8. Morris, L. J., R. T. Holman and K. Fontell, J. Lipid Res.2, 68–76 (1961).

    CAS  Google Scholar 

  9. Fioriti, J. A., and R. J. Sims, J. Chromatogr.32, 761–763 (1968).

    Article  PubMed  CAS  Google Scholar 

  10. Dobinson, B., W. Hofmann and B. P. Stark, “The Determination of Epoxide Groups” Pergamon Press, Ltd., Oxford, England, 1969, 79 p.

    Google Scholar 

  11. Jay, R. R., Anal. Chem.36, 667–668 (1964).

    Article  CAS  Google Scholar 

  12. Smith, C. R., Jr., M. C. Burnett, T. L. Wilson, R. L. Lohmar and I. A. Wolff, JAOCS37, 320–323 (1960).

    CAS  Google Scholar 

  13. Harris, J. A., F. C. Mage and E. L. Skau, Ibid.40, 718–720 (1963).

    Article  CAS  Google Scholar 

  14. Tallent, W. H., D.G. Cope, J. W. Hagemann, F. R. Earle and I. A. Wolff, Lipids1, 335–340 (1966).

    Article  CAS  Google Scholar 

  15. Karstens, H., Fette, Seifen, Anstrich.71, 267–269 (1969).

    Article  CAS  Google Scholar 

  16. Kanno, S., and Z. Ninomiya, J. Japan Oil Chem. Soc.17, 685–688 (1968).

    CAS  Google Scholar 

  17. Swern, D., T. W. Findley, G. N. Billen and J. T. Scanlon, Anal. Chem.19, 414–415 (1947).

    Article  CAS  Google Scholar 

  18. Morris, L. J., and R. T. Holman, J. Lipid Res.2, 77–82 (1961).

    CAS  Google Scholar 

  19. Soucek, J., and J. Vašátková, Collect. Czechoslov. Chem. Commun.31, 2860–2865 (1966).

    CAS  Google Scholar 

  20. Fioriti, J. A., M. J. Kanuk and R. J.Sims, J. Chromatogr. Sci.7, 448–450 (1969).

    CAS  Google Scholar 

  21. Herb, S. F., P. Magidman and R. A. Barford, JAOCS41, 222–224 (1964).

    CAS  Google Scholar 

  22. Kleiman, R., G. F. Spencer and F. R. Earle, Lipids4, 118–122 (1969).

    Article  CAS  Google Scholar 

  23. Maerker, G., and E. T. Haeberer, JAOCS43, 97–100 (1966).

    CAS  Google Scholar 

  24. Kleiman, R., G. F. Spencer, L. W. Tjarks and F. R. Earle, 60th AOCS Meeting, San Francisco, 1969, Abstract 102.

  25. Mizuno, G. R., E. C. Ellison and J. R. Chipault, Microchemical J.14, 227–234 (1969).

    Article  CAS  Google Scholar 

  26. Kleiman, R., G. F. Spencer, F. R. Earle and I. A. Wolff, Lipids4, 135–141 (1969).

    Article  CAS  Google Scholar 

  27. Vioque, E., J. Chromatogr.39, 235–237 (1969).

    Article  CAS  Google Scholar 

  28. Gunstone, F. D., J. Chem. Soc.1954, 1611–1616.

  29. Chisholm, M. J., and C. Y. Hopkins, Can. J. Chem.35, 358–364 (1957).

    Article  CAS  Google Scholar 

  30. Chisholm, M. J., and C. Y. Hopkins, Chem. Ind. (London)1960, 1134–1135.

  31. Smith, C. R., Jr., M. O. Bagby, R. L. Lohmar, C. A. Glass and I. A. Wolff, J. Org. Chem.25, 218–222 (1960).

    Article  CAS  Google Scholar 

  32. Smith, C. R., Jr., Kay F. Koch and I. A. WOlff, Chem. Ind. (London)1959, 259–260.

  33. Gunstone, F. D., and L. J. Morris, J. Chem. Soc.1959, 2127–2132.

  34. Chisholm, M. J., and C. Y. Hopkins, Chem. Ind. (London)1959, 1154–1155.

  35. Conacher, H. B. S., and F. D. Gunstone, Lipids5, 137–141 (1970).

    Article  PubMed  CAS  Google Scholar 

  36. Powell, R. G., C. R. Smith, Jr., and I. A. Wolff, JAOCS42, 165–169 (1965).

    Article  CAS  Google Scholar 

  37. Earle, F. R., and Quentin Jones, Econ. Bot.16, 221–250 (1962).

    CAS  Google Scholar 

  38. Morris, L. J., M. O. Marshall and E. W. Hammond, Lipids3, 91–95 (1968).

    Article  CAS  Google Scholar 

  39. Spencer, G. F., R. Kleiman, F. R. Earle, and I. A. Wolff, Ibid.4, 99–101 (1969).

    Article  CAS  Google Scholar 

  40. Earle, F. R., A. S. Barclay and I. A. Wolff, Ibid.1, 325–327 (1966).

    Article  CAS  Google Scholar 

  41. Phillips, B. E., C. R. Smith, Jr., and J. W. Hagemann, Ibid.4, 473–477 (1969).

    Article  PubMed  CAS  Google Scholar 

  42. Mikolajczak, K. L., R. M. Freidinger, C. R. Smith, Jr., and I. A. Wolff, Ibid.3, 489–494 (1968).

    Article  CAS  Google Scholar 

  43. Jones, Q., and F. R. Earle, Econ. Bot.20, 127–155 (1966).

    CAS  Google Scholar 

  44. Smith, C. E., “Observations on the Stengeloid Species ofVernonia,” Agricultural Handbook, U.S. Department of Agriculture, in press.

  45. Badami, R. C., and F. D. Gunstone, J. Sci. Food Agr.14, 481–484 (1963).

    Article  CAS  Google Scholar 

  46. Smith, C. R., Jr., Kay F. Koch and I. A. Wolff, JAOCS36, 219–220 (1959).

    Article  CAS  Google Scholar 

  47. Powell, R. G., C. R. Smith, Jr., and I. A. Wolff, Lipids2, 172–177 (1967).

    Article  CAS  Google Scholar 

  48. Barucha, K. E., and F. D. Gunstone, J. Sci. Food Agr.7, 606–609 (1956).

    Article  Google Scholar 

  49. Gunstone, F. D., and P. J. Sykes, Ibid.12, 115–123 (1961).

    Article  CAS  Google Scholar 

  50. Kleiman, R., C. R. Smith, Jr., S. G. Yates and Q. Jones, JAOCS42, 169–172 (1965).

    Article  Google Scholar 

  51. Krewson, C. F., and W. E. Scott, Ibid.43, 171–174 (1966).

    CAS  Google Scholar 

  52. Hopkins, C. Y., and M. J. Chisholm, Ibid.37, 682–684 (1960).

    Article  CAS  Google Scholar 

  53. Hopkins, C. Y., and M. J. Chisholm, Ibid.36, 95–96 (1959).

    CAS  Google Scholar 

  54. Morris, L. J., J. Chem. Soc.1963, 5779.

  55. Tulloch, A. P., Can. J. Chem.38, 204–207 (1960).

    Article  Google Scholar 

  56. Tulloch, A. P., B. M. Craig and G. A. Ledingham, Can. J. Microbiol.,5, 485–491 (1959).

    Article  PubMed  CAS  Google Scholar 

  57. Tulloch, A. P., Can. J. Chem.43, 415–420 (1965).

    Article  CAS  Google Scholar 

  58. Vioque, E., L. J. Morris and R. T. Holman, JAOCS38, 489–492 (1961).

    CAS  Google Scholar 

  59. Riser, G. E., R. W. Riemenschneider and L. P. Witnauer, Ibid.43, 456–457 (1966).

    CAS  Google Scholar 

  60. Krewson, C. F., G. R. Riser and W. E. Scott Ibid,43, 377–379 (1966).

    CAS  Google Scholar 

  61. Berry, C. D., K. J. Lessman, G. A. White and F. R. Earle, Crop Sci.,10, 178–180 (1970).

    Article  Google Scholar 

  62. Krewson, C. F., J. S. Ard and R. W. Riemenschneider, JAOCS39, 334–340 (1962).

    CAS  Google Scholar 

  63. Fioriti, J. A., N. Buide and R. J. Sims, Ibid.,46, 108–112 (1969).

    Article  CAS  Google Scholar 

  64. Mikolajczak, K. L., C. R. Smith, Jr., and I. A. Wolff, Ibid.47, 24–25 (1970).

    CAS  Google Scholar 

  65. Knoche, H. W., 43rd AOCS Meeting, Minneapolis, 1969, Abstract 154.

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Authors and Affiliations

  1. Northern Regional Research Laboratory, 61604, Peoria, Illinois

    F. R. Earle

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  1. F. R. Earle
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No. Utiliz. Res. Dev. Div., ARS, USDA.

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Earle, F.R. Epoxy oils from plant seeds. J Am Oil Chem Soc 47, 510–513 (1970). https://doi.org/10.1007/BF02639239

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  • DOI: https://doi.org/10.1007/BF02639239

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