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

Acrylamide in Soybean Products, Roasted Nuts, and Dried Fruits

“…The latest developments in food processing have been aimed at substantial reduction of damages to nutrients and sensory components by applying the optimal heating conditions. In addition to N-glycosylasparagine (Schiff base), that is a direct precursor of acrylamide [5], 3-aminopropionamide (3-APA) [4,6], hydroxycarbonyls, dicarbonyls [4,7], alkadienals from lipid oxidation [8], and 5-hydroxymethyl-2-furfural (HMF) [9] can be involved in the acrylamide formation as important transient intermediates. These compounds can develop during baking, frying, and roasting due to various chemical reactions such as the Maillard reaction (MR), caramelization, and lipid oxidation.…”

Cysteine alone or in combination with glycine simultaneously reduced the contents of acrylamide and hydroxymethylfurfural

“…In contrast to rodents, which mainly express sulfotransferases in liver, humans express sulfotransferases in many tissues, including the intestine, implying that humans could be more susceptible to HMF than conventional rodent models (Svendsen et al, 2012). Moreover, HMF can be converted to acrylamide and furan during Maillard reaction, (Cai et al, 2014;G€ okmen, Kocadagli, G€ oncüoglu, & Mogol, 2012;Mesias-Garcia, Guerra-Hernandez, & GarciaVillanova, 2010) which are classified as "possibly carcinogenic to humans".…”

Relationship between Antioxidants and Acrylamide Formation

“…HRMS analysis confirmed its role as a potent carbonyl accelerating acrylamide formation [30]. The Asn-HMF model system generated more acrylamide than did the Asn-Glc model system, though the reaction rate was higher in the Asn-Glc system.…”

“…Asparagine was proven to provide the backbone chain of acrylamide formation by mass spectral studies demonstrating that all the three carbon atoms and the nitrogen atom are from asparagine [99]. Subsequent researches showed that the carbonyl can come from multiple sources, including sugar fragments such as glyoxal, hydroxyethanal, and glyceraldehydes [3], some Maillard reaction products like 5-hydroxymethylfurfural [30] as well as specific lipid oxidized products like alkadienals and their analogous ketodienes and hydroperoxides [40]. Classically, the carbonyl compound is an α-hydroxycarbonyl compound (e.g., reducing sugars like glucose or fructose).…”