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Insight into the mechanochemistry of the Maillard reaction: degradation of Schiff bases via 5-oxazolidinone intermediate

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Abstract

With the emergence of mechanochemistry as a fast and efficient synthetic methodology, we reported earlier that ball milling of glucose with histidine leads to the formation of reaction mixtures rich in Schiff bases. Upon subsequent thermal treatments, these mixtures exhibited enhanced reactivity generating more browning and pyrazine-rich volatiles, compared to non-milled samples. To rationalize these observations, we further investigated the mechanochemistry of the Maillard reaction using glycolaldehyde and histidine or phenylalanine as model systems. The conversion of Schiff bases into reactive 5-oxazolidinone in these model systems was proposed as the basis of the observed enhanced reactivity. Furthermore, the formation of 5-oxazolidinone in the ball-milled samples was verified through direct spectroscopic observation of its characteristic FTIR absorption band between 1780 cm−1 and 1810 cm−1 and through the identification of its specific degradation products. The important role of the carboxylic acid moiety in enabling the formation of reactive 5-oxazolidinone intermediate that facilitates its subsequent decarboxylation and formation of downstream degradation products such as dihydropyrazines and Strecker aldehydes were elucidated.

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Acknowledgements

The authors acknowledge funding for this research from Natural Sciences and Engineering Research Council of Canada (NSERC), Le Fonds de Recherche du Québec—Nature et Technologie (FRQNT), and the China Scholarship Council (CSC).

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Natural Sciences and Engineering Research Council of Canada (NSERC), Le Fonds de Recherche du Québec—Nature et Technologie (FRQNT), and China Scholarship Council (CSC).

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  1. Department of Food Science and Agricultural Chemistry, McGill University, 21111 Lakeshore, Sainte-Anne-de-Bellevue, QC, H9X 3V9, Canada

    Haoran Xing & Varoujan Yaylayan

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  1. Haoran Xing
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  2. Varoujan Yaylayan
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Correspondence to Varoujan Yaylayan.

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Xing, H., Yaylayan, V. Insight into the mechanochemistry of the Maillard reaction: degradation of Schiff bases via 5-oxazolidinone intermediate. Eur Food Res Technol 247, 1095–1106 (2021). https://doi.org/10.1007/s00217-021-03690-5

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