Skip to main content
SpringerLink
Log in

Autoxidation of polyunsaturated triacylglycerols. I. Trilinoleoylglycerol

  • Published:
Lipids

Abstract

The hydroperoxides and secondary products formed from trilinoleoylglycerol autoxidized at 40°C were isolated and characterized to clarify their contribution to oxidative deterioration of vegetable oils. The products were purified by high performance liquid chromatography (HPLC) and identified, as intact triacylglycerols, by ultraviolet, infrared,1H NMR and13C NMR analyses, and after derivatization by lipolysis, gas chromatography, and gas chromatography-mass spectrometry. The main, primary products included mono-,bis- and tris-9-hydroperoxy-trans-10,cit-12-; 9-hydroperoxy-trans-10,trans-12; 13-hydroperoxy-cis-9,trans-11; and 13-hydroperoxy-trans-9,trans-11-linolenoyl glycerols. The structures of the minor secondary products analyzed after derivatization were consistent with known oxidative degradation products of linoleate hydroperoxides. HPLC analyses showed that thebis- and tris-hydroperoxides were formed from the mono-hydroperoxides during autoxidation at peroxide values above 18 and 28 meq/kg. Studies on the further oxidation of the mono-hydroperoxides support a mechanism for the consucutive formation ofbis- and tris-hydroperoxides from the monohydroperoxides. HPLC analyses showed that no preferential oxidation occurred between the 1(3)- and 2-triglyceride positions. Hydroperoxides of linoleate triacylglycerols may be important precursors of volatile compounds contributing to off-flavors of vegetable oils.

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

Abbreviations

bis-OOH:

bis-hydroperoxides

GC:

gas chromatography

GC-MS:

gas chromatography mass spectrometry

HPLC:

high performance liquid chromatography

IR:

infrared

mono-OOH:

mono-hydroperoxides

NMR:

nuclear magnetic resonance

OTMS:

trimethylsilyl

PV:

peroxide value

RI:

refractice index

TLC:

thin-layer chromatography

tris-OOH:

tris-hydroperoxides

UV:

ultraviolet

References

  1. Frankel, E.N. (1980)Prog. Lipid Res. 19, 1–22.

    Article  PubMed  CAS  Google Scholar 

  2. Frankel, E.N. (1982)Prog. Lipid Res. 20, 1–33.

    Google Scholar 

  3. Frankel, E.N. (1985)Prog. Lipid Res. 23, 197–221.

    Article  Google Scholar 

  4. Paquette, G., Kuptanycz, D.B., and Van de Voort, F.R. (1985)Can. Inst. Food Sci. Technol. J. 18, 112–118.

    CAS  Google Scholar 

  5. Paquette, G., Kuptanycz, D.B., and Vande Voort, F.R. (1985)Can. Inst. Food Sci. Technol. J. 18, 197–206.

    CAS  Google Scholar 

  6. Chan, H.W.-S., (1987)Autoxidation of Unsaturated Lipids, Academic Press, New York, NY.

    Google Scholar 

  7. Sohde, K., Izutani, S., and Matsushita, S. (1973)Agr. Biol. Chem. 37, 1979–1981.

    CAS  Google Scholar 

  8. Terao, J., and Matsushita, S. (1978)Agric. Biol. Chem. 42, 667–668.

    CAS  Google Scholar 

  9. Terao, J., and Matsushita, S. (1981)Agric. Biol. Chem. 45, 601–608.

    CAS  Google Scholar 

  10. Park, D.K., Terao, J., and Matsushita, S. (1981)Agric. Biol. Chem. 45, 2071–2076.

    CAS  Google Scholar 

  11. Park, D.K., Terao, J., and Matsushita, S. (1981)Agric. Biol. Chem. 45, 2443–2448.

    CAS  Google Scholar 

  12. Peers, K.E., and Coxon, D.T. (1983)Chem. Phys. Lipids 32, 49–56.

    Article  CAS  Google Scholar 

  13. Cosgrove, J.P., Church, D.F., and Pryor, W.A. (1987)Lipids 22, 299–304.

    Article  PubMed  CAS  Google Scholar 

  14. Chapman, R.H., and MacKay, K. (1949)J. Am. Oil Chem. Soc. 26, 360–363.

    CAS  Google Scholar 

  15. Oette, K. (1965)J. Lipid Res. 6, 449–454.

    PubMed  CAS  Google Scholar 

  16. Bus, J., Seis, J., and Lie Ken Jie, M.S.F. (1977)Chem. Phys. Lipids 18, 130–144.

    Article  PubMed  CAS  Google Scholar 

  17. Neff, W.E., Frankel, E.N., and Weisleder, D. (1982)Lipids 17, 780–790.

    Article  CAS  Google Scholar 

  18. Neff, W.E., Frankel, E.N., Selke, E., and Weisleder, D. (1983)Lipids 18, 868–876.

    Article  CAS  Google Scholar 

  19. Frankel, E.N., Neff, W.E., Rohwedder, W.K., Khambay, B.P.S., Garwood, R.F., and Weedon, B.C.L. (1977)Lipids 12, 908–913.

    Article  PubMed  CAS  Google Scholar 

  20. Neff, W.E., Frankel, E.N., Scholfield, C.R., and Weisleder, D. (1978)Lipids 13, 415–421.

    Article  CAS  Google Scholar 

  21. Yoshida, H., Murata, K., and Kajimoto, G. (1985)Nutrition Reports International 32, 707–717.

    CAS  Google Scholar 

  22. Mack, C.H., and Bickford, W.G. (1953)J. Org. Chem. 18, 686–692.

    Article  CAS  Google Scholar 

  23. Gardner, H.W., and Weisleder, D. (1972)Lipids 7, 191–193.

    Article  CAS  Google Scholar 

  24. Chan, H.W.-S., and Levett, G. (1977)Lipids 12, 99–104.

    Article  PubMed  CAS  Google Scholar 

  25. Bus, J., and Frost, D.J. (1984)Recl. Trav. Chim. Pays-Bas 93, 213–242.

    Google Scholar 

  26. Bus, J., Sies, I., and Lie Ken Jie, M.S.F. (1976)Chem. Phys. Lipids 17, 501–518.

    Article  CAS  Google Scholar 

  27. Bus, J., Sies, J., and Lie Ken Jie, M.S.F. (1977)Chem. Phys. Lipids 18, 130–144.

    Article  PubMed  CAS  Google Scholar 

  28. Gunstone, F.D., Pollard, M.R., Scrimegeour, C.M., and Vedanayagam, H.S. (1977)Chem. Phys. Lipids 18, 115–129.

    Article  PubMed  CAS  Google Scholar 

  29. Tulloch, A.P., and Mazurek, M. (1976)Lipids 11, 228–234.

    Article  CAS  Google Scholar 

  30. Miyashita, K., Fujimoto, K., and Kaneda, T. (1982)Agric. Biol. Chem. 46, 751–755.

    CAS  Google Scholar 

  31. Miyashita, K., Hara, N., Fujimoto, K., and Kaneda, T. (1985)Lipids 20, 578–587.

    Article  CAS  Google Scholar 

  32. Frankel, E.N. (1987)Chem. Phys. Lipids 44, 73–85.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Author notes

  1. E. N. Frankel

    Present address: Department of Food Science and Technology, University of California, 95616, Davis, CA

  2. K. Miyashita (Visiting scientist)

    Present address: Hokkaido University, Hakodate, Japan

Authors and Affiliations

  1. Northern Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, 61604, Peoria, IL

    W. E. Neff, E. N. Frankel & K. Miyashita (Visiting scientist)

Authors
  1. W. E. Neff
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. N. Frankel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Miyashita
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Neff, W.E., Frankel, E.N. & Miyashita, K. Autoxidation of polyunsaturated triacylglycerols. I. Trilinoleoylglycerol. Lipids 25, 33–39 (1990). https://doi.org/10.1007/BF02562425

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02562425

Keywords

Search

Navigation