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Reactive carbonyl-scavenging ability of 2-aminoimidazoles: 2-amino-1-methylbenzimidazole and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).

Journal of agricultural and food chemistry (2014-11-25)
Francisco J Hidalgo, Esmeralda Alcón, Rosario Zamora
ABSTRACT

The carbonyl-scavenging ability of 2-amino-1-methylbenzimidazole (AMBI) and the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in an attempt to identify new routes that can modify the carbonyl content of foods. The reaction of both AMBI and PhIP with 2-alkenals, 2,4-alkadienals, 4-oxo-2-alkenals, 4,5-epoxy-2-alkenals, and 4-hydroxy-2-nonenal produced fluorescent adducts, whose structure was determined for the adduct produced between AMBI and 2-pentenal. This adduct was isolated and identified by one- and two-dimensional nuclear magnetic resonance and high-resolution mass spectrometry as 2,10-dihydro-2-ethyl-10-methylpyrimido[1,2-a]benzimidazole. The formation of these adducts was parallel to the elimination of AMBI and PhIP. The Ea of the reaction between PhIP and 4-oxo-2-nonenal was 27.4 kJ/mol. All these results suggest that 2-aminoimidazoles can be employed to modify the carbonyl content of foods. At the same time and because the reaction produces the disappearance of the amino compound, lipid-derived carbonyl compounds can be employed to eliminate 2-aminoimidazoles, which suggests a new strategy for the elimination of heterocyclic aromatic amines in foods.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2-Pentylfuran, ≥98%, FG
Sigma-Aldrich
2,4-Heptadienal, technical grade, 90%
Sigma-Aldrich
2-Amino-1-methylbenzimidazole, 95%
Sigma-Aldrich
2-Ethylfuran, ≥99%
Sigma-Aldrich
2-Pentylfuran, natural (US), ≥97%, FG
Supelco
2-Ethylfuran, analytical standard
Sigma-Aldrich
2-Ethylfuran, 97%