The DOI matches its Crossref record; 6 of the 6 references it cites were found in a registry or an index.
Acrylamide Formation Mechanism in Heated Foods
Abstract
Recent findings of a potential human carcinogen, acrylamide, in foods have focused research on the possible mechanisms of formation. We present a mechanism for the formation of acrylamide from the reaction of the amino acid asparagine and a carbonyl-containing compound at typical cooking temperatures. The mechanism involves formation of a Schiff base followed by decarboxylation and elimination of either ammonia or a substituted imine under heat to yield acrylamide. Isotope substitution studies and mass spectrometric analysis of heated model systems confirm the presence of key reaction intermediates. Further confirmation of this mechanism is accomplished through selective removal of asparagine with asparaginase that results in a reduced level of acrylamide in a selected heated food. Keywords: Acrylamide; asparagine; Maillard reaction; LC-MS; foods; asparaginase; potato; reducing sugars; mechanism; isotopes; β-alanine amide; 3-aminopropionamide
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Cites
Acrylamide is formed in the Maillard reaction
Mottram, D. S., Wedzicha, B. L., & Dodson, A. T. (2002) · Nature · doi:10.1038/419448a · Cited by 2,267
Analysis of Acrylamide, a Carcinogen Formed in Heated Foodstuffs
Tareke, E., Rydberg, P., Karlsson, P., Eriksson, S., & Törnqvist, M. (2002) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf020302f · Cited by 2,215
Acrylamide from Maillard Reaction Products
Stadler, R. H., Blank, I., Varga, N., Robert, F., Hau, J., Guy, P. A., Robert, M.-C., & Riediker, S. (2002) · Nature · doi:10.1038/419449a · Cited by 1,678
Acrylamide in Foods: Occurrence, Sources, and Modeling
Becalski, A., Lau, B. P.-Y., Lewis, D., & Seaman, S. W. (2003) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf020889y · Cited by 660
Sethi, A., & Bajaj, B. (2004) · Anil Aggrawal's Internet Journal of Forensic Medicine and Toxicology · Cited by 170
Health Implications of Acrylamide in Food
Skovgaard, N. (2003) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2003.08.001 · Cited by 107
Cited by
Farah, A. (2012) · Coffee · doi:10.1002/9781119949893.ch2 · Cited by 330
Review of Methods for the Reduction of Dietary Content and Toxicity of Acrylamide
Friedman, M., & Levin, C. E. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0730486 · Cited by 271
Han, J.-W., Boo, H., & Chung, M.-S. (2020) · Food Science and Biotechnology · doi:10.1007/s10068-020-00747-1 · Cited by 24
Dietary determinants for Hb-acrylamide and Hb-glycidamide adducts in Danish non-smoking women
Outzen, M., Egeberg, R., Dragsted, L., Christensen, J., Olesen, P. T., Frandsen, H., Overvad, K., Tjønneland, A., & Olsen, A. (2011) · British Journal Of Nutrition · doi:10.1017/s0007114510005003 · Cited by 11
Metadata
- Authors
- Zyzak, D. V., Sanders, R. A., Stojanovic, M., Tallmadge, D. H., Eberhart, B. L., Ewald, D. K., Gruber, D. C., Morsch, T. R., Strothers, M. A., Rizzi, G. P., & Villagran, M. D.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-06-28
- Volume
- 51
- Issue
- 16
- Pages
- 4782-4787
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2006291398
- Cited by
- 869
- References
- 6
- FWCI
- 61.06
- Type
- journal article
- Language
- en
- Open access
- closed
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- Zyzak, D. V., Sanders, R. A., Stojanovic, M., Tallmadge, D. H., Eberhart, B. L., Ewald, D. K., Gruber, D. C., Morsch, T. R., Strothers, M. A., Rizzi, G. P., & Villagran, M. D. (2003). Acrylamide Formation Mechanism in Heated Foods. Journal of Agricultural and Food Chemistry. https://doi.org/10.1021/jf034180i
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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