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Identification of Precursors and Formation Pathway for the Heterocyclic Aromatic Amine 2-Amino-3-methylimidazo(4,5-f)quinoline (IQ).

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Food processing is responsible for the destruction of some health hazards, but it is responsible for the formation of new ones. Among them, the formation of heterocyclic aromatic amines (HAAs)… Click to show full abstract

Food processing is responsible for the destruction of some health hazards, but it is responsible for the formation of new ones. Among them, the formation of heterocyclic aromatic amines (HAAs) has received a considerable attention because of their carcinogenicity. In spite of that, HAAs formation is still poorly understood. This study was undertaken to identify precursors and formation pathways for 2-amino-3-methylimidazo(4,5-f)quinoline (IQ). IQ resulted to be produced by reaction of acrolein, crotonaldehyde, creatinine, and ammonia. Reaction conditions were studied and its activation energy (Ea) determined (77.0  1.3 kJ/mol). IQ formation was always accompanied by the formation of the HAA 2-amino-3,4-dimethylimidazo(4,5-f)quinoline (MeIQ), which was produced with an Ea of 72.2  0.4 kJ/mol. A reaction pathway for the competitive formation of IQ and MeIQ is proposed. Obtained results demonstrate the significant role of reactive carbonyls (the food carbonylome) on HAA formation, and provide evidences for designing HAA mitigation strategies.

Keywords: amino methylimidazo; methylimidazo quinoline; precursors formation; formation; heterocyclic aromatic

Journal Title: Journal of agricultural and food chemistry
Year Published: 2020

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