28588-74-1Relevant articles and documents
Novel Taste-Enhancing 4-Amino-2-methyl-5-heteroalkypyrimidines Formed from Thiamine by Maillard-Type Reactions
Brehm, Laura,Frank, Oliver,Jünger, Manon,Wimmer, Miriam,Ranner, Josef,Hofmann, Thomas
, p. 13986 - 13997 (2019/12/27)
Increasing the thiamine concentration in a respective process flavor yields a product with a significant higher kokumi activity. S-plot analysis of the mass spectrometric data revealed beside thiamine itself, 4-methyl-5-thiazoleethanol, (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteine, N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamide, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one, and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine as marker molecules for a process flavor with higher thiamine concentration. Sensory-based targeted isolation revealed that (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteine, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one, and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine showed an influence on the kokumi taste activity with taste threshold concentrations between 35 and 120 μmol/L. An adapted mass spectrometric-based carbon module labeling experiment as well as quantitative studies clearly demonstrated thiamine as the only precursor and an intermolecular formation pathway for the compounds (S)-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. On the basis of the knowledge that several thiamine derivatives showed taste-modulating activity, selected thiamine-based binary model reactions and synthesis were carried out. This resulted in the isolation of further thiamine-derived taste modulators like (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteinylglycine, (S)-3-((((4-amino-2-methylpyrimidin-5-yl)methyl)thio)methyl)piperazine-2,5-dione, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)pentan-2-one, 5-(((furan-2-ylmethyl)thio)methyl)-2-methylpyrimidin-4-amine, and (4-amino-2-methylpyrimidin-5-yl)methanethiol, 2-methyl-5-((methylthio)methyl)pyrimidin-4-amine with taste thresholds ranging from 35 to 880 μmol/L.
Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars
Lee, Sang Mi,Jo, Ye-Jin,Kim, Young-Suk
experimental part, p. 3116 - 3124 (2011/08/05)
Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.
Effect of pH on the maillard reaction of [C]xylose, cystein, and thiamin
Cerny, Christoph,Briffod, Matthieu
scheme or table, p. 1552 - 1556 (2009/10/01)
The influence of different pH values, ranging from 4.0 to 7.0, on the formation of sulfur volatiles in the Maillard reaction was studied using a model system with [13C5]xylose, cysteine, and thiamin. The use of 13C-labeled xylose allowed, by analysis of the mass spectra, volatiles that incorporated xylose carbons in the molecule from other carbon sources to be discerned. For 2-furaldehyde and 2-furfurylthiol, which were favored at low pH, the labeling experiments clearly indicated that xylose was the exclusive carbon source. On the other hand, xylose was virtually not involved in the formation of 3-mercapto-2-butanone, 4,5-dihydro-2-methyl-3- furanthiol, and 5-(2-hydroxyethyl)-4-methylthiazole, which apparently stemmed from thiamin degradation. Both xylose and thiamin seemed to significantly contribute to the formation of 2-methyl-3-furanthiol, 3-mercapto-2-pentanone, and 2-mercapto-3-pentanone, and therefore different formation pathways must exist for each of these molecules. In general, the pH determined strongly which volatiles were formed, and to what extent. However, the relative contribution of xylose to the C-skeleton of a particular compound changed only slightly within the investigated pH range, when both xylose and thiamin were involved in the formation.
