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Mechanism of Carbon Skeleton Formation of 2,3,5-Trimethylpyrazine via a Conversion Reaction between Methylglyoxal and Glyoxal

Wei Jiang, Xiaoyuan Wang, Yunjiao Ma, Ming Du, Chao Wu, Xianbing Xu

2023Journal of Agricultural and Food Chemistry18 citationsDOI

Abstract

Maillard flavor compounds, such as 2,3,5-trimethylpyrazine, have been frequently identified in thermally processed food products, such as popcorn and peanuts. However, the origin of the carbon atoms in 2,3,5-trimethylpyrazine has not been clearly elucidated. Herein, a model reaction showed that precursor methylglyoxal and intermediates glyoxal and formaldehyde contributed to the formation of 2,3,5-trimethylpyrazine via a conversion reaction between methylglyoxal and glyoxal. In addition, carbon module labeling technology and model response validation experiments indicated that this transformation reaction between methylglyoxal and glyoxal brought formaldehyde into the methyl group carbon atoms of the 2,3,5-trimethylpyrazine ring. The proposed novel route provides a new perspective for approaches to control the formation of flavor compounds, such as 2,3,5-trimethylpyrazine.

Topics & Concepts

MethylglyoxalGlyoxalMaillard reactionChemistryFormaldehydeReaction mechanismFlavorAldehydeOrganic chemistryCarbon fibersPhotochemistryBiochemistryCatalysisMaterials scienceComposite numberEnzymeComposite materialAdvanced Glycation End Products researchGABA and Rice ResearchBiochemical effects in animals