28119-61-1

Usage

InChI:InChI=1/C4H6O3/c5-2-1-4(7)3-6/h3,5H,1-2H2

Upstream product

• 95-43-2 D-threose 
• 50-99-7 D-glucose 
• 657-27-2 L-Lysine hydrochloride 
• 78-98-8 2-oxopropanal 
• 2280-44-6 D-Glucose 
• 57-48-7 D-Fructose 

Relevant academic research and scientific papers

Reactivity of thermally treated α-dicarbonyl compounds

The degradation reaction of thermally treated 3-deoxy-d-erythro-hexos-2- ulose and methylglyoxal, both key intermediates in Maillard chemistry, was investigated. Different analytical strategies were accomplished to cover the broad range of formed products and their different chemical behavior. These involved HPLC-DAD and accordingly LC/MS analysis of the quinoxaline derivates, GC/MS analysis of the acetylated quinoxalines, and GC-FID analysis of the decyl ester of acetic acid. As a main degradation product of 3-deoxy-d-erythro-hexos- 2-ulose, 5-(hydroxymethyl)furfural could be identified. At alkaline pH values, 3-deoxy-d-erythro-hexos-2-ulose generated various acids but no colored products. In contrast, thermal treatment of methylglyoxal yielded high molecular weight, brownish products. A dimer of methylglyoxal, first precursor for aldol-based polymerization of methylglyoxal, could be clearly identified by GC/MS.

Reactivity of 1-deoxy-D-erythro-hexo-2,3-diulose; A key intermediate in the maillard chemistry of hexoses

Degradation of 1-deoxyhexo-2,3-diulose, a key intermediate in Maillard chemistry, in the presence of L-alanine under moderate conditions (37 and 50 °C) was investigated. Different analytical strategies were accomplished to cover the broad range of product

Degradation of glucose: reinvestigation of reactive α-dicarbonyl compounds

Maillard reactions influence the formation of flavor and color in processed foods in an important way. Reducing sugars and amino acids ultimately react to stable end products. To elucidate the complex formation pathways a vast number of experiments have b

Identification and determination of α-dicarbonyl compounds formed in the degradation of sugars

The α-dicarbonyl compounds formed in the degradation of glucose and fructose were analyzed by HPLC using 2,3-diaminonaphthalene as derivatizing reagent, and identified as glucosone (GLUCO), 3-deoxyglucosone (3DG), 3-deoxyxylosone (3DX), tetrosone (TSO), triosone (TRIO), 3-deoxytetrosone (3DT), glyoxal (GO), and methylglyoxal (MGO). The results suggest that α-dicarbonyl compounds were formed from glucose via non-oxidative 3-deoxyglucosone formation and oxidative glucosone formation in glucose degradation. In addition, TRIO, GO, and MGO were also formed from glyceraldehyde as intermediate. The α-dicarbonyl compounds might be formed from glucose via these pathways in diabetes.

TREATMENT OF SUGAR SOLUTIONS

A process for treating a solution containing sugar and α-oxoaldehydes, comprising the step of adding a catalyst which comprises an optionally substituted histidine amino acid, such that the α-oxoaldehydes are catalytically converted to aldonic acids.

The degradation of L-threose at Maillard reaction conditions

L-Threose, a comparatively unstable aldose, is produced from L-ascorbic acid in the presence of oxygen and participates vigorously in Maillard reactions, even at comparatively mild conditions.In the present study, the degradation of L-threose at pH 7.0 alone, in the presence of N-α-acetyl-L-lysine, and at pH 2.0 alone at 37 deg C was investigated by identification of some of the products produced in the reactions by means of GLC and GLC-MS.Among the compounds identified were 3-deoxy-tetros-2-ulose (1), the predicted alkaline rearrangement product derived from 1 (2,4-dihydroxybutyrate, the 4-carbon metasaccharinic acid), as well as glyceraldehyde.Isotopic tracer studies clearly show that the glyceraldehyde is produced by loss of C-1 from the starting L-threose molecule.The presence of N-acetyl lysine in incubation solutions appears to accelerate the production of 1, but the formation of glyceraldehyde appears to be independent of the lysine derivative.