Isotope labeling studies on the origin of 3,4-hexanedione and 1,2-butanedione in an alanine/glucose model system

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 20, 2009, Pages 9740-9746

  Fono Chu, L A M ^a   Yaylayan, Varoujan A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

1,2 butanedione; 3,4 hexanedione; Alanine glyoxal; Isotope labeling; Oxidative and nonoxidative pyrazine formation

Indexed keywords

ALANINE; ALKANONE; CARBON; GLUCOSE; NITROGEN;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; GLYCATION; ISOTOPE LABELING; OXIDATION REDUCTION REACTION;

ALANINE; BUTANONES; CARBON ISOTOPES; GLUCOSE; HEXANONES; ISOTOPE LABELING; MAILLARD REACTION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROGEN ISOTOPES; OXIDATION-REDUCTION;

EID: 70350316489     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf902117v     Document Type: Article

References (22)

1. (1) Yaylayan, V. A.; Keyhani, A. Origin of 2,3-pentanedione and 2,3butanedione in in L-glucose/L-alanine Maillard model systems. J. Agric. Food. Chem. 1999, 47, 3280-3284. (Pubitemid 29422028)
2. Cerny, C. The aroma side of the Maillard reaction. Ann. N. Y. Acad. J. Agric. Food. Chem. 2008, 1126, 66-111
3. Mosciano, G. Organoleptic characteristics of flavor materials. Perfum. Flavor. 2007, 32, 56-58.
4. Salter, L. J.; Mottram, D. S.; Whitfield, F. B. Volatile compounds produced in Maillard reactions involving glycine, ribose and phospholipid. J. sci. food. Agric. 46, 227-242.
5. Whitfield, F. B.; Mottram, D. S. Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)-furanone and cysteine or hydrogen sulfide at pH 4.5. J. Agric. Food. Chem. 1999, 47, 1626-1634.
6. Zheng, Y .; Brown, S.; Ledig, W. O.; Mussinan, C.; Ho, C. T. Formation of sulfur-containing flavor compounds from reactions of furaneol and cysteine, glutathione, hydrogen sulfide, and alanine/ hydrogen sulfide. J. Agric. Food. Chem. 97, 45, 894-897.
7. Ames, J. M.; Guy, R. C. E.; Kipping, G. J. Effect of pH, temperature, and moisture on the formation of volatile compounds in glycine/ glucose model systems. J. Aeric. Food Chem. 2001, 49, 4315-4323.
8. Chiavaro, E.; Vittadini, E.; Musci, M.; Bianchi, F.; Curti, E. Shelflife stability of artisanally and industrially produced durum wheat sourdough bread ("Altamura bread"). LWT-Food Sci.Technol. 2007, 41, 58-70.
9. Rizzi, G. P. Mechanistic study of alkylpyrazine formation in model systems. J. Agric. Food. Chem. 1972, 20, 1081-1085.
10. (a) Hofmann, T; Schieberle, P. Flavor contribution and formation of the intense roast-smelling odorants 2-propionyl-l-pyrroline and 2- propionyltetrahydropyridien in Maillard-type reactions. J. Agric. Food. Chem. 98, 46, 2721-2726.
11. (b) Shu, Ch.-K. Pyrazine formation from serine and threonine. J. Aeric. Food Chem. 1999, 47, 4332-4335.
12. (11) Yaylayan, V. A.; Haftenden, L.; Chu, F. L.; Wnorowski, A. Oxidative pyrolysis and postpyrolytic derivatization techniques for the total analysis of Maillard model systems: investigation of control parameters of Maillard reaction pathways. Ann. N. Y. Acad. Sci. 2005, 1043, 41-54. (Pubitemid 41123887)
13. Amrani-Hemaimi, M.; Cerny, C.; Fay, L. B. Mechanisms of fonnation of alkylpyrazines in the Maillard reaction. J. Agric. Food. chem. 1995, 43, 2818-2822.
14. Adams, A. N.; Polizzi, V.; van Boekel, M.; De Kimpe, N. Formation of pyrazines and a novel pyrrole in Maillard model systems of 1,3dihydroxyacetone and 2-oxopropanal. J. Agric. Food. Chem. 2008, 56, 2147-2153.
15. Adams, A.; De Kimpe, N. Formation of pyrazines from ascorbic acid and amino acids under dry-roasting conditions. Food Chem. 2009, 115, 1417-1423.
16. Barton, D. H., Ollis, W. D., Eds. Comprehensive. Organic Chemistry; Pergamon Press: Oxford, 1979; Vol. 2, p 825.
17. Kaneko, T., Izumi, Y., Chibata I., Itoh, T., Eds. Synthetic Production and Utilization of Amino Acids; Wiley: New York, 1974; pp 196-198.
18. Kinlin, T. E.; Muralidhara, R.; Pittet, A. O.; Sanderson, A.; Walradt, J. P. Volatile components of roasted filberts. J. Aeric, Food. Chem. 1972, 20, 1021-1028.
19. Fadel, H. H. M.; Hegazy, N. A. Improvement and stabilization of bread flavor. Nahrung. 1993, 37, 386-394.
20. Baltes, W.; Bochmann, G. Model reactions on roast aroma fonnation. IV. Mass spectrometry identification of pyrazines from the reaction of serine and threonine with sucrose under the conditions of coffee roasting. Z. Lebensm. - Unters. - Forsch. 1987, 184, 485-493.
21. Vitzthum, O. G.; Werkhoff, P.; Hubert, P. Volatile components of roasted cocoa. Basic fraction. J. Food. Sci 1975, 40, 911-916.
22. (21 ) Mottram, D.S. The effect of cooking conditions on the fonnation of volatile heterocyclic compounds in pork. J. Food. Sci.1985, 36, 377-382.