4084-27-9

Usage

Uses

Used in Chemical Research:
3-Deoxyglucosone is used as an intermediate in the Maillard reaction for the study of protein-glucose interactions and the formation of advanced glycation end products. This application is crucial for understanding the role of 3-DG in various pathological effects, such as carcinogenesis.
Used in Analytical Chemistry:
3-Deoxyglucosone is used as a reference compound for the analysis and detection of glucose degradation products and glycating agents. This application is essential for monitoring and controlling the quality of products in the food and pharmaceutical industries.
Used in Crosslinking Studies:
3-Deoxyglucosone is used as a crosslinking agent in the study of protein-protein interactions, as it readily reacts with protein amino groups. This application is valuable for understanding the structural and functional aspects of proteins and their interactions in biological systems.
Used in Medical Research:
3-Deoxyglucosone is used as a model compound to study the effects of diabetes and oxidative stress on the human body. This application is important for developing therapeutic strategies to combat the complications associated with diabetes and other related conditions.
Used in Pharmaceutical Industry:
3-Deoxyglucosone is used as a starting material for the synthesis of various pharmaceutical compounds. This application is significant for the development of new drugs targeting diabetes and its associated complications.

InChI:InChI=1/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1

Upstream product

• 69-79-4 D-maltose 
• 50-99-7 D-glucose 
• 4429-05-4 N-(1-deoxy-D-fructos-1-yl)-L-glycine 
• 657-27-2 L-Lysine hydrochloride 

Downstream Products

• 99814-06-9 (3-Desoxy-D-threo-hexosulose)-2,4-dinitrophenyl-osazon 
• 119248-49-6 3-Desoxy-D-galactoson-bis-(2,5-dichlor-phenylhydrazon) 
• 107281-04-9 D-erythro-3-deoxy-[2]hexosulose-bis-(4-nitro-phenylhydrazone) 
• 2595-22-4 D-erythro-3-deoxy-[2]hexosulose-bis-(2,4-dinitro-phenylhydrazone) 
• 120928-34-9 3-Desoxy-D-glucoson-bis-(2,5-dichlor-phenylhydrazon) 
• 108-28-1 protoanemonin 
• 6196-57-2 3-deoxy-D-erythro-hexos-2-ulose 
• 1192-79-6 formyl-2 methyl-5 pyrrole 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 1121-25-1 2-methyl-3-pyridinol 
• 110-00-9 furan 
• 534-22-5 2-methylfuran 
• 1623-88-7 5-chloromethylfurfural 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 

Relevant academic research and scientific papers

Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to d -Glucose

In this study, the Maillard reaction of maltose and d-glucose in the presence of l-alanine was investigated in aqueous solution at 130 °C and pH 5. The reactivity of both carbohydrates was compared in regards of their degradation, browning, and antioxidant activity. In order to identify relevant differences in the reaction pathways, the concentrations of selected intermediates such as 1,2-dicarbonyl compounds, furans, furanones, and pyranones were determined. It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone represent the only relevant C6-1,2-dicarbonyls in maltose incubations and are produced in nearly equimolar amounts during the first 60 min of heating as byproducts of the HMF formation.

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.

Kinetic modelling of Amadori N-(1-deoxy-D-fructos-1-yl)-glycine degradation pathways. Part I - Reaction mechanism

The fate of the Amadori compound N-(1-deoxy-D-fructos-1-yl)-glycine (DFG) was studied in aqueous model systems as a function of pH and temperature. The samples were heated at 100 and 120°C with initial reaction pH of 5.5 and 6.8. Special attention was paid to the formation of the free amino acid, glycine; parent sugars, glucose and mannose; organic acids, formic and acetic acid and α-dicarbonyls, 1- and 3-deoxyosone together with methylglyoxal. For the studied conditions decreasing the initial reaction pH with 1.3 units or increasing the temperature with 20°C has the same effect on the DFG degradation as well as on glycine formation. An increase in pH seems to favour the formation of 1-deoxyosone. The lower amount found comparatively to 3-deoxyosone, in all studied systems, seems to be related with the higher reactivity of 1-deoxyosone. Independently of the taken pathway, enolization or retro-aldolization, DFG degradation is accompanied by amino acid release. Together with glycine, acetic acid was the main end product formed. Values of 83 and 55 mol% were obtained, respectively. The rate of parent sugars formation increased with pH, but the type of sugar formed also changed with pH. Mannose was preferably formed at pH 5.5 whereas at pH 6.8 the opposite was observed, that is, glucose was formed in higher amounts than mannose. Also, independently of the temperature, at higher pH fructose was also detected. pH, more than temperature, had an influence on the reaction products formed. The initial steps for a complete multiresponse kinetic analysis have been discussed. Based on the established reaction network a kinetic model will be proposed and evaluated by multiresponse kinetic modelling in a subsequent paper.