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Acrylamide and pyrazine formation in model systems containing asparagine

Koutsidis, G., De la Fuente, A., Dimitriou, C., Kakoulli, A., Wedzicha, B.L. and Mottram, D.S. (2008) Acrylamide and pyrazine formation in model systems containing asparagine. Journal of Agricultural and Food Chemistry, 56 (15). pp. 6105-6112. ISSN 0021-8561

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To link to this item DOI: 10.1021/jf703744k


The effect of different sugars and glyoxal on the formation of acrylamide in low-moisture starch-based model systems was studied, and kinetic data were obtained. Glucose was more effective than fructose, tagatose, or maltose in acrylamide formation, whereas the importance of glyoxal as a key sugar fragmentation intermediate was confirmed. Glyoxal formation was greater in model systems containing asparagine and glucose rather than fructose. A solid phase microextraction GC-MS method was employed to determine quantitatively the formation of pyrazines in model reaction systems. Substituted pyrazine formation was more evident in model systems containing fructose; however, the unsubstituted homologue, which was the only pyrazine identified in the headspace of glyoxal-asparagine systems, was formed at higher yields when aldoses were used as the reducing sugar. Highly significant correlations were obtained for the relationship between pyrazine and acrylamide formation. The importance of the tautomerization of the asparagine-carbonyl decarboxylated Schiff base in the relative yields of pyrazines and acrylamide is discussed.

Item Type:Article
Divisions:Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences
ID Code:13240
Uncontrolled Keywords:acrylamide, Maillard reaction, pyrazines, solid phase microextraction, glyoxal , MAILLARD REACTION, AMINO-ACIDS, POTATO, GENERATION, TEMPERATURE, DEGRADATION, ALDEHYDES, MECHANISM, PATHWAYS, MOISTURE

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