4084-27-9

Basic information

• Product Name: 3-DEOXYGLUCOSONE
• Synonyms: 3-deoxy-d-erythro-hexos-2-ulose;3-deoxy-d-erythro-hexosulos;d-3-deoxyglucosone;3DG;3-DEOXY-D-ERYTHRO-HEXULOSE2-KETO-3-DEOXYGLUCOSE;3-DEOXYGLUCOSONE;3-Deoxy-D-erythro-Hexulose 2-Keto-3-Deoxyglucose 3DG;3-Deoxy-D-glucosone
• CAS NO: 4084-27-9
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• Product Categories: 13C & 2H Sugars;aldehydes;Carbohydrates & Derivatives;Intermediates
• Mol File: 4084-27-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 73-75°C
• Boiling Point: 208.81°C (rough estimate)
• Flash Point: 209.9°C
• Appearance: Yellow/Solid
• Density: 1.2132 (rough estimate)
• Vapor Pressure: 4.59E-08mmHg at 25°C
• Refractive Index: 1.4230 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 13.17±0.20(Predicted)
• Water Solubility: Soluble in water, methanol or hot ethanol.
• Stability: Hygroscopic
• CAS DataBase Reference: 3-DEOXYGLUCOSONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DEOXYGLUCOSONE(4084-27-9)
• EPA Substance Registry System: 3-DEOXYGLUCOSONE(4084-27-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: MQ3390000
• Hazardous Substances Data: 4084-27-9(Hazardous Substances Data)

Usage

Description

3-deoxy Glucosone is a highly reactive 2-oxoaldehyde intermediate of the Maillard reaction produced during oxidative stress in response to excess sugar consumption and in association with diabetes. It is a precursor for the formation of advanced glycation endproducts and because it readily reacts with protein amino groups is also used for crosslinking studies. 3-deoxy Glucosone can be used as a reference for the analysis and detection of glucose degradation products and glycating agents.

Chemical Properties

Amorphous Yellow Solid

Uses

Different sources of media describe the Uses of 4084-27-9 differently. You can refer to the following data:
1. An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carcinogenesis
2. Frequently used as a reference for the analysis and detection of glucose degradation products and glycating agents. Also used for cross-linking studies as it readily reacts with protein amino groups.

Definition

ChEBI: A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.

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

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

Downstream Products

• 1192-79-6 formyl-2 methyl-5 pyrrole 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 1121-25-1 2-methyl-3-pyridinol 
• 7284-15-3 2-deoxy-D-ribonic acid 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 
• 127-17-3 2-oxo-propionic acid 
• 64-18-6 formic acid 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 431-03-8 dimethylglyoxal 
• 78-98-8 2-oxopropanal 
• 39131-44-7 5-bromomethyl-furan-2-carbaldehyde 
• 1623-88-7 5-chloromethylfurfural 
• 110-00-9 furan 
• 534-22-5 2-methylfuran 

Relevant articles and documents

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.

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.