Formation of α-dicarbonyl compounds in beer during storage of pilsner

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 11, 2008, Pages 4134-4144

  Bravo, Adriana ^a   Herrera, Julio C ^b   Scherer, Erika ^a   Ju Nam, Yon ^a   Rübsam, Heinrich ^a   Madrid, Jorge ^b   Zufall, Carsten ^a   Rangel Aldao, Rafael ^a,b  

^a Unidad de Investigación e Innovación   (Venezuela)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Dicarbonyl quantification; 1,4 dideoxydiuloses; 1 deoxydiuloses; Beer aging; GC olfactometry

Indexed keywords

2 NONENAL; 2-NONENAL; 3 DEOXYGLUCOSONE; 3-DEOXYGLUCOSONE; ACETALDEHYDE; ALDEHYDE; DEOXYGLUCOSE; DRUG DERIVATIVE; FURAN DERIVATIVE; FURANEOL; PHENYLACETALDEHYDE;

ARTICLE; BEER; FOOD HANDLING; FOOD PRESERVATION; GAS CHROMATOGRAPHY; HUMAN; ODOR; TIME;

ACETALDEHYDE; ALDEHYDES; BEER; CHROMATOGRAPHY, GAS; DEOXYGLUCOSE; FOOD HANDLING; FOOD PRESERVATION; FURANS; HUMANS; SMELL; TIME FACTORS;

EID: 47049086523     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf703696p     Document Type: Article

References (37)

1. Narziss, L.; Miedaner, H.; Graf, H.; Eichhorn, P.; Lustig, S. Technological approach to improve flavor stability. Tech. Q. Master Brew. Assoc. Am. 1993, 30, 48-53.
2. Hashimoto, N. In Brewing Science, Vol. II; Pollock, J. R., Ed.; Academic Press: San Diego, 1981; pp 347-405.
3. Huige, N. J. Progress in Beer Oxidation Control. In Beer and Wine Production: Analysis, Characterization, and Technological Advances, ACS Symposium Series 536; Gump, B. H., Pruett, D. J., Eds.; American Chemical Society: Washington, DC, 1993; pp 64-97.
4. Bravo, A.; Sánchez, B.; Scherer, E.; Herrera, J.; Rangel-Aldao, R. α-Dicarbonylic compounds as indicators and precursors of flavor deterioration during beer aging. Tech. Q. Master Brew. Assoc. Am. 2002, 39, 13-23.
5. Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2- methyl-3(2H)-furanone and of α-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines. Z. Lebensm.-Unters.-Forsch. 1992, 194, 222-228.
6. Hollnagel, A.; Kroh, L. W. Degradation of oligosaccharides in nonenzymatic browning by formation of α-dicarbonyl compounds via a "peeling off" mechanism. J. Agric. Food Chem. 2000, 48, 6219-6226.
7. Morita, N.; Inoue, K.; Tagaki, N. Quinoxalines derived from D-glucose and o-phenylendiamine in a weakly acidic medium. Agric. Biol. Chem. 1981, 45, 2665-2668.
8. Morita, N.; Inoue, K.; Tagaki, N. Quinoxalines derived from disaccharides with o-phenylendiamine under weakly acidic refluxed conditions. Agric. Biol. Chem. 1985, 49, 3279-3289.
9. (a) Wittmann, R.; Eichner, K. Detection of Maillard products in malts, beers, and brewing couleurs. Z. Lebensm.-Unters.-Forsch. 1989, 188, 212-220.
10. (b) Glomb, M. A.; Tschirnich, R. Detection of α-dicarbonyl compounds in Maillard reaction systems and in vivo. J. Agric. Food Chem. 2001, 49, 5543-5550.
11. Madson, M. A.; Feather, M. S. An improved preparation of 3-deoxy-D-erythro-hexos-2-ulose via the bis(benzoylhydrazone) and some related constitutional studies. Carbohydr. Res. 1981, 94, 183-191.
12. Hofmann, T.; Bors, W.; Stettmaier, K. Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids. J. Agric. Food Chem. 1999, 47, 379-390.
13. 13C-labeling experiments. Carbohydr. Res. 1998, 313, 215-224.
14. IUPAC Compendium of Chemical Terminology (1997). http://goldbook.iupac. org/L03540.html.
15. Vesely, P.; Lusk, L.; Basarova, G.; Seabrooks, J.; Ryder, D. Analysis of aldehydes in beer using solid-phase microextraction with on-fiber derivatization and gas chromatography-mass spectrometry. J. Agric. Food Chem. 2003, 51, 6941-6944.
16. Van den Dool, H.; Kratz, P. D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. 1963, 11, 463-471.
17. Kramhöller, B.; Ledl, F.; Lerche, H.; Severin, T. HPLC separation of some characteristic components in reaction mixtures of disaccharides with amines - Model systems for milk and cereal products. Z. Lebensm.-Unters.- Forsch. 1992, 194, 431-433.
18. Kramhöller, B.; Pischetsrieder, M.; Severin, T. Maillard reactions of lactose and maltose. J. Agric. Food Chem. 1993, 41, 347-351.
19. Anet, E. F. L. J. 3-Deoxyglycosuloses (3-deoxyglucosones) and the degradation of carbohydrates. Adv. Carbohydr. Chem. 1964, 19, 181-218.
20. Wedzicha, B. L.; Vakalis, N. Kinetics of the sulfite inhibited Maillard reaction: The effect of sulfite ion. Food Chem. 1988, 27, 259-271.
21. Weenen, H.; Tjan, S. B. Analysis, Structure, and Reactivity of 3-Deoxyglucosone. In Flavor Precursors. Thermal and Enzymatic Conversions, ACS Symposium Series 490; Teranishi, R., Takeoka, G. R., Güntert, M., Eds.; American Chemical Society: Washington, DC, 1992; pp 217-231.
22. Fickert, B.; Schieberle, P. Comparative Study on the Flavour of Caramalt and Caramalt Beer. In Proceedings of the European Brewing Convention, 27th Congress, Cannes, 1999; pp 71-78.
23. Cutzach, I.; Chatonnet, P.; Dubourdieu, D. Study of the formation mechanism of some volatile compounds during the aging of sweet fortified wines. J. Agric. Food Chem. 1999, 47, 2837-2846.
24. Kim, M. O.; Baltes, W. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4(H)-pyran-4-one in the Maillard reaction. J. Agric. Food Chem. 1996, 44, 282-289.
25. Morita, N.; Mizutani, M.; Hayashi, K.; Kirihata, M.; Ichimono, I.; Ueda, H.; Takagi, M. Quinoxalines derived from D-glucose and maltose with o-phenylenediamine under refluxed conditions in alkaline media. Bull. Univ. Osaka Prefect., Ser. B 1983, 35, 59-70.
26. da Fonseca, S. I. Unravelling the Maillard reaction by multiresponse kinetic modelling. Ph.D. Thesis, Wageningen University, Wageningen, The Netherlands, 2003.
27. Glomb, M. A.; Tschirnich, R. Detection of α-dicarbonyl compounds in Maillard reaction systems and in vivo. J. Agric. Food Chem. 2001, 49, 5543-5550.
28. Bravo, A. Los compuestos α-dicarbonílicas y el envejecimiento de la cerveza. Ph.D. Thesis, Universidad Simón Bolívar, Caracas, Venezuela, 2003.
29. Tan, Y.; Siebert, K. J. Quantitative structure-activity relationship modeling of alcohol, ester, aldehyde, and ketone flavor thresholds in beer from molecular features. J. Agric. Food Chem. 2004, 52, 3057-3064.
30. Lermusieau, G.; Bulens, M.; Collin, S. Use of GC-olfactometry to identify the hop aromatic compounds in beer. J. Agric. Food Chem. 2001, 49, 3867-3874.
31. Shaw, P. E.; Berry, R. E. Hexose-amino acid degradation studies involving formation of pyrrols, furans, and other low molecular weight products. J. Agric. Food Chem. 1977, 25, 641-645.
32. Schieberle, P. Formation of Furaneol in Heat-Processed Foods. In Flavor Precursors. Thermal and Enzymatic Conversions, ACS Symposium Series 490; Teranishi, R., Takeoka, G. R., Güntert, M., Eds.; American Chemical Society: Washington, DC, 1992; pp 164-174.
33. Lermusieau, G.; Noël, S.; Liegéois, C.; Collin, S. Nonoxidative mechanism for development of trans-2-nonenal in beer. J. Am. Soc. Brew. Chem. 1999, 57, 29-33.
34. Schieberle P.; Komarek, D. Changes in Key Aroma Compounds during Natural Beer Aging. In Freshness and Shelf Life of Foods, ACS Symposium Series 836; Cadwallader, K. R., Weenen, H., Eds.; American Chemical Society: Washington, DC, 2002; pp 70-79.
35. Soares da Costa, M.; Gonçalves, C.; Ferreira, A.; Ibsen, C.; Guedes de Pinho Silva Ferreira, A. C. Further insights into the role of methional and phenylacetaldehyde in lager beer flavor stability. J. Agric. Food Chem. 2004, 52, 7911-7917.
36. Wedzicha, B. L. Chemistry of Sulphur Dioxide in Foods; Elsevier Applied Science Publishers: Amsterdam, 1984; pp 214-216.
37. Kaneda, H.; Osawa, T.; Kawakishi, S.; Munekata, M.; Koshino, S. Contribution of carbonyl-bisulfite adducts to beer stability. J. Agric. Food Chem. 1994, 42, 2428-2432.