D6134

2-Deoxy-D-glucose

≥99% (GC), crystalline

• Synonym(s): 2-Deoxy-D-arabinohexose
• Empirical Formula (Hill Notation): C₆H₁₂O₅
• CAS Number: 154-17-6
• Molecular Weight: 164.16
• Beilstein: 1723331
• EC Number: 205-823-0
• MDL number: MFCD00151328
• PubChem Substance ID: 24894000
• NACRES: NA.25

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• Assay: ≥99% (GC)
• form: crystalline
• technique(s): gas chromatography (GC): suitable
• color: white
• mp: 146-147 °C (lit.)
• solubility: H₂O: soluble 330 mg/mL, clear, colorless
• storage temp.: 2-8°C
• SMILES string: OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
• InChI: 1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
• InChI key: VRYALKFFQXWPIH-PBXRRBTRSA-N

Description

Application

2-Deoxy-D-glucose (2-DG) is used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). 2-Deoxy-D-glucose is used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress.

Biochem/physiol Actions

2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which can not be further metabolized by phosphoglucose isomerase. This leads to the accumulation of 2-DG-P in the cell and the depletion in cellular ATP. In vitro, 2-Deoxyglucose has been shown to induce autophagy, increase ROS production, and activate AMPK.

Preparation Note

A further purification of the Grade II material by recrystallization.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves