D6134
2-Deoxy-D-glucose
≥99% (GC), crystalline
Synonym(s):
2-Deoxy-D-arabinohexose
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About This Item
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
205-823-0
Beilstein/REAXYS Number:
1723331
MDL number:
InChI key
VRYALKFFQXWPIH-PBXRRBTRSA-N
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
SMILES string
OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
biological source
synthetic (organic)
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
Quality Level
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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.
Other Notes
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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