Model studies on the role of 5-hydroxymethyl-2-furfural in acrylamide formation from asparagine

GÖKMEN V., KOCADAĞLI T., Göncüoǧlu N., Mogol B. A.

Food Chemistry, vol.132, no.1, pp.168-174, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 132 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.1016/j.foodchem.2011.10.048
  • Journal Name: Food Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.168-174
  • Keywords: Acrylamide, 5-Hydroxymethyl-2-furfural, Sugar dehydration, Maillard reaction, 3-Aminopropionamide, MAILLARD REACTION, PRODUCTS, 3-AMINOPROPIONAMIDE, FOODS
  • Hacettepe University Affiliated: Yes


This study aimed to investigate the mechanism of acrylamide formation during heating asparagine (ASN) at elevated temperatures with glucose (GLC), and 5-hydroxymethyl-2-furfural (HMF). The results revealed that HMF rapidly reacted with ASN, leading to acrylamide formation. The ASN-HMF model system generated acrylamide more efficiently than the ASN-GLC model system during heating at 180 °C. A significantly higher amount of 3-aminopropionamide (3-APA) was formed in the ASN-HMF model system than in the ASN-GLC model system within 5 min at 180 °C. The amount of 3-APA decreased after 5 min of heating in both model systems while the amount of acrylamide continued to increase in the ASN-HMF model system. In-depth high resolution mass spectrometry analyses of reaction products formed in the model systems together with the kinetic data suggested that HMF is a potent carbonyl accelerating acrylamide formation during heating. 3-APA was found as one of the key intermediates leading to acrylamide formation. © 2011 Elsevier Ltd. All rights reserved.