On the significant influence of water on the formation mechanisms of 5-acetyl-3,4-dihydro-2H-1,4-thiazine
W. Engel | P. Schieberle
The formation of 5-acetyl-3,4-dihydro-2H-1,4-thiazine in Maillard-type reactions of fructose with cysteamine under dry heating and cooking conditions was studied. Labelling experiments with 2-13C-fructose revealed, that the formation pathways are completely different, depending on the water content of the mixture. Under dry heating conditions, 5-(1-13C-acetyl)-3,4-dihydro-2H-1,4-thiazine is formed almost exclusively with the 2-13C of fructose found at the carbonyl carbon of the acetyl group. Under cooking conditions, ADHT is mostly unlabelled and most probably formed from erythrulose. Erythrulose might be generated from 2-13C-fructose by loss of 1-13C-acetic acid, indicated by the high amount of the latter found in the mixture. A possible mechanism leading from fructose to erythrulose is postulated.
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