Thermally Generated 3-Aminopropionamide as a Transient Intermediate in the Formation of Acrylamide

• Published in: Journal of agricultural and food chemistry Vol. 54; no. 16; pp. 5933 - 5938
• Main Authors: Granvogl, Michael, Schieberle, Peter
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 09.08.2006
• Subjects: 3-aminopropionamide; Acrylamide - chemistry; acrylamides; amides; asparagine; Asparagine - chemistry; beta-Alanine - analogs & derivatives; beta-Alanine - chemistry; biogenic amines; Biological and medical sciences; Cheese - analysis; chemical reactions; Food industries; food processing; Food toxicology; Fundamental and applied biological sciences. Psychology; Glucose - chemistry; Gouda cheese; heat treatment; Hot Temperature; Milk and cheese industries. Ice creams; model food systems; Acrylamide; Gouda cheese; Strecker reaction; Aminoacid; Gouda; Dairy product; Asparagine; Cheese; 3-aminopropionamide; Labeling experiments
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf061150h

On the basis of the recent findings that “biogenic amines” can also be formed during thermal food processing from their parent amino acids in a Strecker-type reaction, the formation of 3-aminopropionamide, the biogenic amine of asparagine, was investigated in model systems as well as in thermally processed Gouda cheese. The results of model studies revealed that, besides acrylamide, 3-aminopropionamide was also formed in amounts of 0.1−0.4 mol % when asparagine was reacted in the presence of either glucose or 2-oxopropionic acid. Results of a second series of model experiments in which [13C4 15N2]-asparagine ([13C4 15N2]-Asn) and unlabeled 3-aminopropionamide were reacted together in the presence of glucose revealed a >12-fold higher efficacy of 3-aminopropionamide in acrylamide generation as compared to asparagine. Both [13C3 15N2]-3-aminopropionamide and [13C3 15N1]-acrylamide were formed during [13C4 15N2]-Asn degradation in a ratio of about 1:4, supporting the idea that 3-aminopropionamide is a transient intermediate in acrylamide formation. In this study, 3-aminopropionamide was identified and quantified for the first time in foods, namely, in Gouda cheese. Although the fresh cheese contained low amounts of 3-aminopropionamide, its concentrations were much increased to ≈1300 μg/kg after thermal processing. In isotope labeling studies, performed by administering to the cheese [13C4 15N2]-Asn in a ratio of 1:2 as compared to the “natural” concentrations of asparagine, similar ratios of unlabeled/labeled 3-aminopropionamide and unlabeled/labeled acrylamide were determined. Thus, 3-aminopropionamide could be verified as a transient intermediate of acrylamide formation during food processing. Keywords: Labeling experiments; 3-aminopropionamide; acrylamide; asparagine; Strecker reaction; Gouda cheese