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Study on Maillard reaction mechanism by quantum chemistry calculation

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Abstract

Context

The Maillard reaction is a high-temperature reaction of amino acids and carbohydrates to produce macromolecular substances such as melanoidins and intermediate reducing ketones, aldehydes, and volatile compounds. At present, only very limited researches involved the reaction mechanisms of Maillard reaction, which causes a lot of confusion in understanding numerous food processes. The detailed calculations of Maillard reaction are urgently needed.

Methods

The density functional theory (DFT) method (M06-2X/6-311G*) was used to deeply explore the specific mechanism of the primary and intermediate stages of Maillard reaction for a selected model system.

Results

The results show that the basic reaction processes in primary stage are the formation of Schiff-base by the condensation of amino and carbonyl groups, and then, Schiff-base tautomerization twice through proton transfer to generate Amadori rearrangement products. In the intermediate stage, two main reaction paths, 1-2 and 2-3 enolization, were comprehensively investigated. The first route finally generates 5-hydroxymethylfurfural through isomerization, dehydration, hydrolysis, elimination, and condensation, and the second route products dicarbonyl compounds through isomerization and elimination and then Strecker degradation forms aldehydes through condensation, decarboxylation, hydrolysis, and elimination. The results show that both paths are involved in complex reactions, some are lower barrier reactions, and some higher barrier reactions. An important aspect is that water catalysis is critical in all of these reactions; it is present in most processes. Our study deepens the understanding of the Maillard reaction from molecular level and facilitate the regulation of some harmful products.

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Funding

This work was supported by the National Natural Science Foundation of China (no. 21603261).

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Authors and Affiliations

  1. College of Food Science and Technology, Shanghai Ocean University, No. 999 Hucheng Huan Road, LinGang New City, Shanghai, 201306, China

    Yubi Gao, Junjian Miao & Keqiang Lai

  2. Engineering Research Center of Food Thermal-Processing Technology, Shanghai Ocean University, Shanghai, 201306, China

    Junjian Miao & Keqiang Lai

Authors
  1. Yubi Gao
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  2. Junjian Miao
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Contributions

Yubi Gao: original draft, software; Junjian Miao: revise draft; Keqiang Lai: revise draft. All authors reviewed the manuscript.

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Correspondence to Junjian Miao.

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Gao, Y., Miao, J. & Lai, K. Study on Maillard reaction mechanism by quantum chemistry calculation. J Mol Model 29, 81 (2023). https://doi.org/10.1007/s00894-023-05484-w

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