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Volatile components from the non-enzymic browning reaction of the cysteine/cystine-ribose system

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Summary

Volatile components from the Maillard reaction of the Cysteine/Cystine-ribose system of low water content were investigated. The reaction conditions were as follows: 0.01 mol ofl-cysteine andl-cystine each, 0.025 mol ofd-ribose and 35 ml of a phosphate buffer solution of pH 5.6 in 200 ml diethylene glycol. This mixture was heated for 24 h under reflux at 125° C. Analysis of the reaction mixture was performed by gas and thin-layer chromatography. Some 45 components, comprising thiophenes, thiazoles, a trithiane, pyrazines, pyrroles, pyridines, amines and furans, were identified. In the vapour above the reaction mixture 3 alkyl thiols, hydrogen sulphide and carbon disulphide were detected by flame photometric analysis. Possible pathways for the formation of 2-acylthiazoles, and of 3-methyl, and 5-methyl substituted 2-formylthiophenes are proposed.

Zusammenfassung

Die flüchtigen Verbindungen der Maillard-Reaktion des Cystein/Cystin-Ribose-Systems von niederigem Wassergehalt wurden untersucht. Die folgenden Reaktionsbedingungen wurden angewandt: 0,01 mol sowohl vonl-Cystein als vonl-Cystin, 0,025 mol vond-Ribose und 35 ml eines Phosphatpuffergemisches von pH 5,6 in 200 ml Diäthylenglycol. Dieses Gemisch wurde 24 Std unter Rückfluß bei 125° C erhitzt. Die Analyse des Reaktionsgemisches wurde mittels Gas- und Dünnschichtchromatographie durchgeführt. Etwa 45 Verbindungen, worunter Thiophene, Thiazole, ein Trithian, Pyrazine, Pyrrole, Pyridine, Amine und Furane, wurden identifiziert. In dem Dampf über dem Reaktionsgemisch wurden 3 Alkylthiole, Schwefelwasserstoff und Schwefelkohlenstoff mittels flammenphotometrischer Analyse vorgefunden. Mögliche Bildungswege für 2-Acylthiazole und für 3-Methyl, und 5-Methyl substituierten 2-Formylthiophene werden vorgeschlagen.

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Authors and Affiliations

  1. Central Institute for Nutrition and Food Research TNO, Utrechtseweg 48, Zeist, The Netherlands

    E. J. Mulders

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Acknowledgement. The author is grateful to J. W. Marsman of the Institute of Organic Chemistry TNO, Utrecht, Netherlands, for the determination of the nmr spectra.

The author is also indebted to R. Belz, J. Bouwman, J. Th. Heins, C. van Ingen, R. J. C. Kleipool and M. C. ten Noever de Brauw for assistance in obtaining and interpreting mass and infrared spectra, and to R. J. C. Kleipool and A. Tas for synthesizing components, without which it would not have been possible to arrive in all instances at positive identifications.

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Mulders, E.J. Volatile components from the non-enzymic browning reaction of the cysteine/cystine-ribose system. Z Lebensm Unters Forch 152, 193–201 (1973). https://doi.org/10.1007/BF01106493

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