The effect of high pressure on the formation of volatile products in a model Maillard reaction

Abstract

Reaction progress in the formation and subsequent decay of several of the volatile products from a model Maillard reaction between lysine and xylose has been followed at pH 7 and 10 and at elevated pressures. At low pH, the buildup and decay of 5-methyl-4-hydroxy-3(2H )-furanone and several minor products were observed. The application of high pressure results in a much diminished maximum concentration of each although the time to the maximum is unaffected. At pH 10, products contain nitrogen heterocycles with 2-methylpyrazine being the principal one which builds up and only slowly decays with time. Again, the yield is greatly reduced by pressure. The results are interpreted in terms of the inhibition by pressure of the formation of the precursor, the Amadori rearrangement product which affects subsequent products. In some instances rates of formation are also found to be slightly inhibited while degradation of these products is accelerated. The corresponding mechanisms are examined in the light of these results.

References

1. High Pressure Processing of Foods, D. A. Ledward, R. G. Earnshaw, D. E. Johnston and A. P. M. Hastings(eds.), University of Nottingham Press, Loughborough, 1995.
2. High Pressure Bioscience and Biotechnology, R. Hayashi and C. Balny(eds.), Elsevier Science BV, Amsterdam, 1996.
3. D. Knorr, V. Heinz, O. Schlüter and M. Zenker, High Pressure Food Science, Bioscience and Chemistry, N. S. Isaacs, (ed.), Royal Society of Chemistry, 1998, p. 227.
4. J. E. Hodge, J. Agric. Food Chem., 1953, 1, 928.
5. H. E. Nursten, Food Chem., 1980, 6, 263.
6. J. M. Ames, The Maillard Reaction in Biochemistry of food proteins, B. J. F. Hudson(ed.), Elsevier Applied Science Publishers, London, 1992, p. 99.
7. N. S. Isaacs and M. Coulson, J. Phys. Org. Chem., 1996, 9, 639.
8. A. Apriyantono and J. M. Ames, J. Sci. Food Agric., 1993, 61, 477.
9. R. Hayashi, Agric. Biol. Chem., 1991, 55, 2071.
10. N. S. Isaacs, High pressure techniques in chemistry and physics, W. Holzapfel and N. S. Isaacs(eds.), Oxford University Press, 1997, p. 324.
11. From a data base made available by courtesy of D. S. Mottram whose help in identification we acknowledge with gratitude.
12. I. Blank and L. B. Fay, J. Agric. Food Chem., 1996, 44, 531.
13. V. Hill, PhD Thesis, Reading University, 1998.
14. T. Shono and Y. Matsumura, Tetrahedron Lett., 1976, 1363; S. Torii, H. Tanaka, T. Anoda and Y. Shimizu, Chem. Lett., 1976, 495.
15. M. Kim and W. Baltes, J. Agric. Food Chem., 1996, 44, 282.
16. G. Brule and P. Dubois, Ann. Technol. Agri., 1971, 20, 305.
17. T. Shibamoto and R. A. Bernhard, J. Agric. Food Chem., 1977, 25, 609.
18. A. Arnoldi, C. Arnoldi, O. Baldi and A. Grini, J. Agric. Food Chem., 1988, 36, 988.
19. H. I. Hwang, T. G. Hartman, R. T. Rosen and C. T. Ho, J. Agric. Food Chem., 1993, 41, 2112 (ibid., 1994, 42, 1000).
20. P. E. Koehler, M. E. Mason and J. A. Newell, J. Agric. Food Chem., 1969, 17, 393.