Antioxidative Effect of Maillard Reaction Intermediates

  • Karl Eichner

Abstract

During oxidation of unsaturated fatty acids via a radical-chain mechanism (Schultz, Day and Sinnhuber, 1962) primarily hydroperoxides are formed, which are decomposed to free radicals entering again the radical-chain thus further promoting fat oxidation. They are split to aldehydes (rancid products) as it is demonstrated in Fig. 1 for linoleic acid. The decomposition of the two isomeric hydroperoxides shown in Fig. 1 to radicals and volatile aldehydes is taking place according to the following reaction pattern:

Keywords

Sugar Peroxide Corn Hexanal Glycine 

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Literature References

  1. Bauernfeind, J.C. (1953): The use of ascorbic acid in processing foods. Adv. Food Res. 4, 359.Google Scholar
  2. Crowe, L.K., Jenness, R. Coulter, S.T. (1948): The reducing capacity of milk and milk products as measured by a modified ferricyanide method. J. Dairy Sci. 31, 595.CrossRefGoogle Scholar
  3. Eichner, K. Karel, M. (1972): The influence of water content and water activity on the sugar-amino browning reaction in model systems under various conditions. J. Agr. Food Chem. 20, 218.Google Scholar
  4. Eichner, K. (1975): The influence of water content on nonenzymic browning reactions in dehydrated foods and model systems and the inhibition of fat oxidation by browning intermediates. Proceedings of an International Symposium on Water Relations of Foods. Academic Press, p. 417–434 ( R.B. Duckworth, Ed. )Google Scholar
  5. Euler, H.V. Eistert, B. (1957): Chemie und Biochemie der Reduktone und Reduktonate. F. Enke Verlag, Stuttgart.Google Scholar
  6. Evans, C.D., Moser, H.A., Cooney, P.M. Hodge, J.E. (1958): Amino-hexose-reductones as antioxidants. I. Vegetable Oils. J. Amer. Oil Chemists Soc. 35, 84.CrossRefGoogle Scholar
  7. Findlay, J.D., Higginbottom, C., Smith, J.A.B. Lea, C.H. (1946): The effect of the pre-heating temperature on the bacterial count and storage life of whole milk powder spray-dried by the Krause process. J. Dairy Res. 14, 378.CrossRefGoogle Scholar
  8. Griffith, T. Johnson, J.A. (1957): Relation of the browning reaction to storage stability of sugar cookies. Cereal Chem. 34, 159.Google Scholar
  9. Hodge, J.E. (1953): Chemistry of browning reactions in model systems. J. Agr. Food Chem. 1, 928.Google Scholar
  10. Hodge, J.E. Rist, C.E. (1953): The Amadori rearrangement under new conditions and its significance for nonenzymic browning reactions. J. Amer. Chem. Soc. 75, 316.Google Scholar
  11. Hwang, C.-J. Kim, D.H. (1973): The antioxidant activity of some extracts from various stages of a Maillard-type browning reaction mixture. Chem. Abstr. 79, 114189e.Google Scholar
  12. Jwainsky, H. Franzke, Cl. (1956): Zur antioxydativen Wirkung der Melanoidine. Dtsch. Lebensmittle-Rdsch. 52, 129.Google Scholar
  13. Koch, S.D., Hyatt, A.A. Lopiekes, D.V. (1971): Basis of the stability of amine salts of linoleic acid. 1. Generally of the oxidation protection and effect of physical state. J. Food Sci. 36, 477.CrossRefGoogle Scholar
  14. Kuhn, R. Dansi, A. (1936): Ber. dt. chem. Ges. 69, 1745.CrossRefGoogle Scholar
  15. Linow, F., Roloff, M. Täufel, K. (1966): Zur Analytik der Carbonylverbindungen und Hydroperoxide bei der Autoxydation olefinischer Fette. 2. Mitteilung: Bestimmung von Carbonylen neben Hydroperoxiden in essigsaurem Miliue. Fette, Seifen 68, 866.Google Scholar
  16. Lundberg, W.O. (1961): Autoxidation and antioxidants. John Wiley and Sons, Inc., New York.Google Scholar
  17. Maleki, M. (1973): The effect of non-enzymic browning in the presence of glucose and glycine on the development of rancidity in corn oil. Fette, Seifen 75, 103.Google Scholar
  18. Mottern, H.H., Spadaro, J.J. Gallo, A.S. (1969): Cooking- extrusion-expansion of rice. Food Technol. 23, 567.Google Scholar
  19. Neurath, H. Bailey, K. (1953): The Proteins. Academic Press, Inc., New York.Google Scholar
  20. Obata, H. (1972): Antioxidative effects of reductones on vegetable oils. Chem. Abstr. 77, 3944n.Google Scholar
  21. Patton, S. (1955): Browning and associated changes in milk and and its products: a review. J. Dairy Sci. 38, 457.CrossRefGoogle Scholar
  22. Rhee, C. Kim, D.H. (1975): Antioxidant activity of acetone extracts obtained from a caramelization-type browning reaction. J. Food Sci. 40, 460.CrossRefGoogle Scholar
  23. Rockland, L.B. (1960): Saturated salt solutions for static control of relative humidity between 5° and 40°C, Analytical Chemistry 32, 1375.CrossRefGoogle Scholar
  24. Sato, K., Hegarty, G.R. Herring, H.K. (1973): The inhibition of warmedover flavor in cooked meats. J. Food Sci. 38, 398.CrossRefGoogle Scholar
  25. Schultz, H.W., Day, E.A. Sinnhuber, R.O. (1962): Lipids and their oxidation. The AVI Publishing Company, Westport, CT.Google Scholar
  26. Tarr, H.L.A. Cooke, N.E. (1950): Comparative value of carbonyl enediols in retarding enzymic browning of fruits. Food Technol. 4, 245.Google Scholar
  27. Yamaguchi, N. et al. (1968): Browning reaction products produced by the reaction between sugars and amino acids. IV. Relationship between potassium ferricyanide-reducing power and stability of lard in cookies. V. Effect of browning reaction products and legal antioxidants on the stability of fats. Chem. Abstr. 68, 2027s, 48427a.Google Scholar
  28. Yamaguchi, N. et al. (1969): Browning reaction products produced by the reaction between sugars and amino acids. VII. Decomposition of lipid hydroperoxides by the browning products. Chem. Abstr. 70, 10526k.Google Scholar
  29. Yamaguchi, N. et al. (1970): Browning reaction products from reducing sugars and amino acids. X. Fractionation of browning reaction products on Sephadex column and anti-oxidative activity of the fractionated material. Chem. Abstr. 73, 97607w.Google Scholar
  30. Zipser, M.W. Watts, B.M. (1961): Lipid oxidation in heat sterilized beef. Food Technol. 15, 445.Google Scholar

Copyright information

© Springer Science+Business Media New York 1980

Authors and Affiliations

  • Karl Eichner
    • 1
  1. 1.Fraunhofer-Institute für Lebensmitteltechnologie und VerpackungMünchen 50Germany

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