title: Model studies on the role of 5-hydroxymethyl-2-furfural in acrylamide formation from asparagine.
abstract: 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 5min at 180°C. The amount of 3-APA decreased after 5min 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.
authors.affiliation: Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey; Food Research Center, Hacettepe University, 06800 Beytepe, Ankara, Turkey. Electronic address: vgokmen@hacettepe.edu.tr.
authors.forename: Vural
authors.initials: V
authors.lastname: Gökmen
authors.affiliation: Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
authors.forename: Tolgahan
authors.initials: T
authors.lastname: Kocadağlı
authors.affiliation: Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
authors.forename: Neslihan
authors.initials: N
authors.lastname: Göncüoğlu
authors.affiliation: Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
authors.forename: Burçe Ataç
authors.initials: BA
authors.lastname: Mogol
mesh_terms: D020106:Acrylamide / Q000737:chemistry*; D001216:Asparagine / Q000737:chemistry*; D005511:Food Handling / Q000379:methods*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D020106:Acrylamide; D001216:Asparagine; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde
keywords: 3-Aminopropionamide; 5-Hydroxymethyl-2-furfural; Acrylamide; Maillard reaction; Sugar dehydration