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Acrylamide formation mechanism in heated foods.
J Agric Food Chem. 2003 Jul 30; 51(16):4782-7.JA

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.

Authors+Show Affiliations

The Procter & Gamble Company, Winton Hill Business Center, 6210 Center Hill Avenue, Cincinnati, Ohio 45224, USA. Zyzak.dv@pg.comNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

14705913

Citation

Zyzak, David V., et al. "Acrylamide Formation Mechanism in Heated Foods." Journal of Agricultural and Food Chemistry, vol. 51, no. 16, 2003, pp. 4782-7.
Zyzak DV, Sanders RA, Stojanovic M, et al. Acrylamide formation mechanism in heated foods. J Agric Food Chem. 2003;51(16):4782-7.
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, 51(16), 4782-7.
Zyzak DV, et al. Acrylamide Formation Mechanism in Heated Foods. J Agric Food Chem. 2003 Jul 30;51(16):4782-7. PubMed PMID: 14705913.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Acrylamide formation mechanism in heated foods. AU - Zyzak,David V, AU - Sanders,Robert A, AU - Stojanovic,Marko, AU - Tallmadge,Daniel H, AU - Eberhart,B Loye, AU - Ewald,Deborah K, AU - Gruber,David C, AU - Morsch,Thomas R, AU - Strothers,Melissa A, AU - Rizzi,George P, AU - Villagran,Maria D, PY - 2004/1/7/pubmed PY - 2005/2/3/medline PY - 2004/1/7/entrez SP - 4782 EP - 7 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 51 IS - 16 N2 - 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. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/14705913/Acrylamide_formation_mechanism_in_heated_foods_ DB - PRIME DP - Unbound Medicine ER -