title: Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model systems.
abstract: NH4HCO3 is known to promote acrylamide formation in sweet bakery products. This effect was investigated with respect to sugar fragmentation and formation of acrylamide from asparagine and sugar fragments in model systems under mild conditions. The presence of NH4HCO3 led to increases in acrylamide and alpha-dicarbonyls from glucose and fructose, respectively. As compared to glucose or fructose, sugar fragments such as glyoxal, hydroxyethanal, and glyceraldehyde formed much higher amounts of acrylamide in reaction with asparagine. The enhancing effect of NH4HCO3 is explained by (1) the action of NH3 as base in the retro-aldol reactions leading to sugar fragments, (2) facilitated retro-aldol-type reactions of imines in their protonated forms leading to sugar fragments, and (3) oxidation of the enaminols whereby glyoxal and other reactive sugar fragments are formed. These alpha-dicarbonyl and alpha-hydroxy carbonyl compounds may play a key role in acrylamide formation, especially under mild conditions.
authors.affiliation: Institute of Food Science and Nutrition, Swiss Federal Institute of Technology (ETH), ETH Zurich, CH-8092 Zurich, Switzerland. thomas.amrein@ilw.agrl.ethz.ch
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Amrein
authors.forename: Luca
authors.initials: L
authors.lastname: Andres
authors.forename: Giuseppe G G
authors.initials: GG
authors.lastname: Manzardo
authors.forename: Renato
authors.initials: R
authors.lastname: Amado
mesh_terms: D020106:Acrylamide / Q000138:chemical synthesis*; D001216:Asparagine / Q000737:chemistry; D001639:Bicarbonates / Q000494:pharmacology*; D005632:Fructose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D015416:Maillard Reaction; D011765:Pyruvaldehyde / Q000032:analysis; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology*
chemical_list: D001639:Bicarbonates; D000644:Quaternary Ammonium Compounds; D020106:Acrylamide; D005632:Fructose; D001216:Asparagine; D011765:Pyruvaldehyde; D005947:Glucose