Abstract
The formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated using a kinetic study approach as described by first-order, Arrhenius, and Eyring equations. Chemical model systems with different amino acid precursors (proline, phenylalanine, and glycine) were examined at different times (4, 8, 12, and 16 min) and temperatures (150, 180, 210, 240, and 270 °C). PhIP was detected using high-performance liquid chromatography equipped with fluorescence detector (HPLC-FLD). The good fit in first-order suggested that PhIP formation was influenced by the types of amino acids and PhIP concentration significantly increased with time and temperature (up to 240 °C). PhIP was detected in proline and phenylalanine model systems but not in the glycine model system. The phenylalanine model system demonstrated low activation energy (Ea) of 95.36 kJ/mol that resulted in a high rate of PhIP formation (great amount of PhIP formed). Based on the ∆S‡ values both proline and phenylalanine demonstrated bimolecular rate-limiting steps for PhIP formation. Altogether these kinetic results could provide valuable information in predicting the PhIP formation pathway.
Highlights
Heterocyclic amines (HCAs) are known as food mutagens/carcinogens that are formed when heat is introduced to muscle food such as meat, poultry, and fish during food preparation [1,2,3]
A PhIP peak was detected in proline and phenylalanine model systems at 28.24–28.52
At higher temperatures of 240 and 270 ◦ C, PhIP formation was reduced in proline and phenylalanine model systems due to degradation
Summary
Heterocyclic amines (HCAs) are known as food mutagens/carcinogens that are formed when heat is introduced to muscle food such as meat, poultry, and fish during food preparation [1,2,3]. The. HCAs are formed in cooked food when the cooking temperature reaches greater than 150 ◦ C [2,4]. HCAs can be divided into two classes based on their formation and chemical conformation, namely the aminoimidazo-azaarenes (IQ-types) and the amino-carboline (non-IQ-types) [4,5]. The aminoimidazo-azaarenes, commonly known as AIA-type, are the major subclass of HCAs found in human diet [6]. The AIA-type HCAs include: i. ii. iii. iv. v.
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