Document Detail

Acrylamide formation mechanism in heated foods.
MedLine Citation:
PMID:  14705913     Owner:  NLM     Status:  MEDLINE    
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.
David V Zyzak; Robert A Sanders; Marko Stojanovic; Daniel H Tallmadge; B Loye Eberhart; Deborah K Ewald; David C Gruber; Thomas R Morsch; Melissa A Strothers; George P Rizzi; Maria D Villagran
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  51     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2003 Jul 
Date Detail:
Created Date:  2004-01-06     Completed Date:  2005-01-31     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4782-7     Citation Subset:  IM    
The Procter & Gamble Company, Winton Hill Business Center, 6210 Center Hill Avenue, Cincinnati, Ohio 45224, USA.
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MeSH Terms
Acrylamide / analysis,  chemical synthesis*,  chemistry
Asparagine / chemistry
Carcinogens / analysis,  chemical synthesis*
Food Analysis*
Hot Temperature*
Schiff Bases / chemistry
Solanum tuberosum / chemistry
Reg. No./Substance:
0/Carcinogens; 0/Schiff Bases; 7006-34-0/Asparagine; 79-06-1/Acrylamide

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