Formation of Pyrazines and a Novel Pyrrole in Maillard Model Systems of 1,3-Dihydroxyacetone and 2-Oxopropanal

A. Adams, V. Polizzi, T. van Boekel, N. de Kimpe

Research output: Contribution to journalArticleAcademicpeer-review

47 Citations (Scopus)

Abstract

Alkylpyrazines are a very important class of Maillard flavor compounds, but their mechanism of formation is complex and consists of different pathways. The model reaction of 20 different amino acids with 1,3-dihydroxyacetone, as a precursor of 2-oxopropanal, was studied by means of SPME-GC-MS to investigate the involvement of the amino acid side chain in the substitution pattern of the resulting pyrazines. 2,5-Dimethylpyrazine was quantitatively the most important pyrazine formed from all of the amino acids. The amino acid side chain is not involved in its formation. The substituents of other less abundant pyrazines resulted mainly from the incorporation of the Strecker aldehyde or aldol condensation products in the intermediate dihydropyrazine. The importance of different reaction mechanisms was evaluated, taking into account the pattern of pyrazines identified. In the solvent extracts of aqueous model reactions of 2-oxopropanal with amino acids, the main reaction product was not a pyrazine but a novel pyrrole. This pyrrole was identified as 2,5-diacetyl-3-methyl-1H-pyrrole by means of spectral analysis, secured by chemical synthesis. A reaction mechanism for its formation was proposed and evaluated. The influence of various reaction conditions on the formation of 2,5-diacetyl-3-methyl-1H-pyrrole and 2,5-dimethylpyrazine in the model reaction of alanine with 2-oxopropanal was studied. These results underscore the importance of the ratio of the different reagents and the presence of water in the resulting flavor formation in the Maillard reaction.
Original languageEnglish
Pages (from-to)2147-2153
JournalJournal of Agricultural and Food Chemistry
Volume56
Issue number6
DOIs
Publication statusPublished - 2008

Keywords

  • sugar-amine reactions
  • 6-acetyl-1,2,3,4-tetrahydropyridine
  • alkylpyrazines
  • chemistry
  • acids

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