Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model systems

被引：60

作者：

Amrein, Thomas M. ^{[1
]}

Andres, Luca ^{[1
]}

Manzardo, Giuseppe G. G. ^{[1
]}

Amado, Renato ^{[1
]}

机构：

[1] ETH, Swiss Fed Inst Technol, Inst Food Sci & Nutr, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2006年 / 54卷 / 26期

关键词：

acrylamide; ammonium hydrogencarbonate; Maillard reaction; retro-aldol; retro-aldol type; reactive sugar fragments; glyoxal; alpha-dicarbonyls; alpha-hydroxycarbonyls;

D O I：

10.1021/jf0625860

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

NH4HCO3 is known to promote acrylamide formation in sweet bakery products. This effect was investigated with respect to sugar fragmentation and formation of acrylamide from asparagine and sugar fragments in model systems under mild conditions. The presence of NH4HCO 3 led to increases in acrylamide and α-dicarbonyls from glucose and fructose, respectively. As compared to glucose or fructose, sugar fragments such as glyoxal, hydroxyethanal, and glyceraldehyde formed much higher amounts of acrylamide in reaction with asparagine. The enhancing effect of NH 4HCO3 is explained by (1) the action of NH3 as base in the retro-aldol reactions leading to sugar fragments, (2) facilitated retro-aldol-type reactions of imines in their protonated forms leading to sugar fragments, and (3) oxidation of the enaminols whereby glyoxal and other reactive sugar fragments are formed. These α-dicarbonyl and α-hydroxy carbonyl compounds may play a key role in acrylamide formation, especially under mild conditions. © 2006 American Chemical Society.

引用

页码：10253 / 10261

页数：9

共 48 条

[21]

Mottram D.S., Wedzicha B.L., Dodson A.T., Acrylamide is formed in the Maillard reaction, Nature, 419, pp. 448-449, (2002)

[22]

Biedermann M., Noti A., Biedermann-Brem S., Mozetti V., Grob K., Experiments on acrylamide formation and possibilities to decrease the potential of acrylamide formation in potatoes, Mitt. Lebensm. Hyg, 93, pp. 668-687, (2002)

[23]

De Vleeschouwer K., Van der Plancken I., Van Loey A., Hendrickx M.E., Impact of pH on the kinetics of acrylamide formation/elimination reactions in model systems, J. Agric. Food Chem, 54, pp. 7847-7855, (2006)

[24]

Amrein T.M., Schonbachler B., Escher F., Amado R., Factors influencing acrylamide formation in gingerbread, Chemistry and safety of acrylamide in food, pp. 431-446, (2005)

[25]

Hollnagel A., Kroh L.W., Formation of alpha-dicarbonyl fragments from mono- and disaccharides under caramelization and Maillard reaction conditions, Eur. Food Res. Technol, 207, pp. 50-54, (1998)

[26]

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, 47, pp. 379-390, (1999)

[27]

Rydberg P., Eriksson S., Tareke E., Karlsson P., Ehrenberg L., Tornqvist M., Investigations of factors that influence the acrylamide content of heated foodstuffs, J. Agric. Food Chem, 51, pp. 7012-7018, (2003)

[28]

Hayashi T., Namiki M., Role of sugar fragmentation in an early stage browning of amino-carbonyl reaction of sugar with amino acid, Agric. Biol. Chem, 50, pp. 1965-1970, (1986)

[29]

Stadler R.H., Robert F., Riediker S., Varga N., Davidek T., Devaud S., Goldmann T., Hau J., Blank I., In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the Maillard reaction, J. Agric. Food Chem, 52, pp. 5550-5558, (2004)

[30]

Bell L.N., Maillard reaction as influenced by buffer type and concentration, Food Chem, 59, pp. 143-147, (1997)

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