Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 48, Issue 8, Pages 3549-3554Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf9913099
Keywords
Maillard reaction mechanism; D-[C-13]glucoses; [C-13-2]glycine; cyclotene; furans; pyrroles; trimethylpyrazine; 2,3-butanedione; 3-hydroxy-2-butanone; 2-methyl-4,5-dihydro-3(2H)-furanone
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The influence of the reaction phase on the mechanism of formation of Maillard products was studied by comparison of C-13-label incorporation patterns of the common products formed in model systems consisting of labeled glycine and D-glucoses subjected to both pyrolysis and heating in aqueous solutions. Pyrolysis experiments were performed at 250 degrees C for 20 s, and aqueous model systems were heated in sealed vials for 3 h at 120 degrees C followed by GC/MS analysis. Label incorporation patterns of the following compounds were analyzed: cyclotene, furanmethanol, acetylpyrrole, 5-methyl-pyrrole, trimethylpyrazine, acetic acid, 3-hydroxy-2-butanone, 2,3-butanedione, and 2-methyl-4,5-dihydro-3(2H)-furanone. Although pyrolysis reaction produced higher number of products, however, the major pathways of formation of variety of important Maillard products followed the same mechanism under both pyrolytic and aqueous systems. Furthermore, contrary to literature speculations, 2-methyl-4,5-dihydro-3(2H)-furanone was shown to be formed by ring contraction of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one, through benzilic acid rearrangement, followed by decarboxylation.
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