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Model experiments about the formation of volatile carbonyl compounds

  • Technical
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Journal of the American Oil Chemists’ Society

Abstract

Autoxidation of linoleic acid, 9-hydroperoxy-10, 12-octadecadienoic acid (9-HPOD), 13-hydroperoxy-9, 11-octadecadienoic acid (13-HPOD), 2-octenal and 2,4-decadienal at 38 C were investigated with respect to the formation of volatile carbonyl compounds. The 13-HPOD and all compounds having a double bond in ω-6-position produce hexanal. After initiating by small amounts of alkoxy radicals, both hexanal and 2,4-decadienal autoxideize further. While, individually, hexanal reacts somewhat faster than 2,4-decadienal, forming the corresponding acid, in a mixture of the two aldehydes, hexanal is protected to a certain extent by the unsaturated aldehyde against autoxidation. This explains the predominance of hexanal among the volatile carbonyl compounds resulting from linoleic acid autoxidation. Small amounts of 2-octenal originate from both the 9-HPOD and the 2,4-decadienal as a result of oxidation of the ω-8-double bond of these compounds. Aside from its acid as main autoxidation product, 2-octenal yields heptanal and hexanal as volatile compounds.

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References

  1. Forss, D.A., Prog. Chem. Fats Other Lipids 13:177 (1973).

    Article  CAS  Google Scholar 

  2. Badings, H.T., Ned. Melk Zuiveltijdschr. 24:147 (1970).

    CAS  Google Scholar 

  3. Sephton, H.H., and D.A. Sutton, JAOCS 33:263 (1956).

    Article  CAS  Google Scholar 

  4. Dolev, A.W., W.K. Rohwedder and H. Dutton, Lipids 2:28 (1967).

    Article  CAS  Google Scholar 

  5. Frankel, E.N., W.E. Neff, W.K. Rohwedder, B.P.S. Khambay, R.F. Garwood and B.C.L. Weedon, Ibid. 12:908 (1977).

    Article  CAS  Google Scholar 

  6. Chan, H.W.-S., and G. Levett, Ibid. 12:99 (1977).

    Article  CAS  Google Scholar 

  7. Bell, E.R., J.H. Raley, F.F. Rust, F.H. Seubold and W.E. Vaughan, Faraday Soc. Disc. 10:242 (1951).

    Article  Google Scholar 

  8. Frankel, E.N., J. Nowakowska and C.D. Evans, JAOCS 38:161 (1961).

    Article  CAS  Google Scholar 

  9. Kimoto, W.J., and A.M. Gaddis, Ibid. 46:403 (1969).

    Article  CAS  Google Scholar 

  10. Evans, C.D., G.R. List, A. Dolev, D.G. McConnel and R.L. Hoffman, Lipids 2:5 (1967).

    Article  Google Scholar 

  11. Badings, H.T., JAOCS 36:648 (1959).

    Article  CAS  Google Scholar 

  12. Chan, H.W.-S., F.A.A. Prescott and P.A.T. Swoboda, Ibid. 53: 572 (1976).

    Article  CAS  Google Scholar 

  13. Grosch, W., Z. Lebensm. Unters. Forsch. 163:4 (1977).

    Article  CAS  Google Scholar 

  14. Swoboda, P.A.T., and C.H. Lea, J. Sci. Food Agric. 16:680 (1965).

    Article  CAS  Google Scholar 

  15. Lillard, D.A., and E.A. Day, JAOCS 41:549 (1964).

    CAS  Google Scholar 

  16. Matthews, F.F., R.A. Scalan and I.M. Libbey, Ibid. 48:745 (1971).

    Article  CAS  Google Scholar 

  17. Michalski, S.T., and E.G. Hammond, Ibid. 49:563 (1972).

    Article  CAS  Google Scholar 

  18. Loury, M., Lipids 7:671 (1972).

    Article  CAS  Google Scholar 

  19. Forney, M., Rev. Fr. Corps Gras 21:429 (1974).

    CAS  Google Scholar 

  20. Morita, M., and M. fujimaki, J. Agric. Food Chem. 21:860 (1973).

    Article  CAS  Google Scholar 

  21. Esterbauer, H., Fette Seifen Anstrichm. 70:1 (1968).

    Article  CAS  Google Scholar 

  22. Grosch, W., Z. Lebensm. Unters. Forsch. 137:216 (1968).

    Article  CAS  Google Scholar 

  23. Bartlett, P.D., E.P. Benzing and R.E. Pincock, J. Am. Chem. Soc. 82:1762 (1960).

    Article  CAS  Google Scholar 

  24. Purr, A., Fette Seifen Anstrichm. 55:239 (1953).

    Article  CAS  Google Scholar 

  25. Schieberle, P., B. Tsoukalas and W. Grosch, Ibid. 168:448 (1979).

    CAS  Google Scholar 

  26. Johnston, A.E., K.T. Zilch, E. Selke and H.J. Dutton, JAOCS 38:367 (1961).

    Article  CAS  Google Scholar 

  27. Schlenk, H., and J.L. Gellerman, Anal. Chem. 32:1412 (1960).

    Article  CAS  Google Scholar 

  28. Heimann, W., K.-H. Franzen and A. Rapp, Z. Lebensm. Unters. Forsch. 158:65 (1975).

    Article  CAS  Google Scholar 

  29. Schwartz, D.P., O.W. Parks and M. Keeney, Anal. Chem. 34:669 (1962).

    Article  CAS  Google Scholar 

  30. Schormüller, J., M. Walther and W. Wachs, Z. Lebensm. Unters. Forsch. 139:273 (1969).

    Article  Google Scholar 

  31. Grosch, W., G. Laskaway and K.-H. Fischer, Lebensm. Wiss. Technol. 7:335 (1974).

    CAS  Google Scholar 

  32. Badings, H.T., and J.G. Wassink, J. Chromatogr. 18:159 (1965).

    Article  CAS  Google Scholar 

  33. Tsoukalas, B., and W. Grosch, JAOCS 54:490 (1977).

    CAS  Google Scholar 

  34. Ohloff, G., in “Fette als funktionelle Bestandteile von Lebensmitteln,” edited by J. Solms, Forster Verlag, Zürich, 1973.

    Google Scholar 

  35. Streitwieser, A., and C.H. Heathcock, “Organische Chemie,” Verlag Chemie, Weinheim, 1980, p. 470.

    Google Scholar 

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Authors and Affiliations

  1. Deutsche Forschungsanstalt für Lebensmittelchemie, 8046, Garching, Germany

    P. Schieberle & W. Grosch

Authors
  1. P. Schieberle
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  2. W. Grosch
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Schieberle, P., Grosch, W. Model experiments about the formation of volatile carbonyl compounds. J Am Oil Chem Soc 58, 602–607 (1981). https://doi.org/10.1007/BF02672374

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  • DOI: https://doi.org/10.1007/BF02672374

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