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2-Deoxy-D-glucose

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2-Deoxy-D-glucose Basic information

Product Name:
2-Deoxy-D-glucose
CAS:
154-17-6
MF:
C6H12O5
MW:
164.16
EINECS:
205-823-0
Mol File:
154-17-6.mol
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2-Deoxy-D-glucose Chemical Properties

Melting point:
146-147 °C(lit.)
alpha 
45.5 º (c=2, H2O)
Boiling point:
211.61°C (rough estimate)
Density 
1.1738 (rough estimate)
refractive index 
46.5 ° (C=1, H2O)
storage temp. 
0-6°C
solubility 
H2O: 50 mg/mL, clear, colorless to faintly yellow
pka
pK1:12.52 (25°C)
form 
crystalline
color 
white
Water Solubility 
Soluble in water.
Merck 
14,2904
BRN 
1723331
InChIKey
PMMURAAUARKVCB-CEZCPVKQSA-N
CAS DataBase Reference
154-17-6(CAS DataBase Reference)
EPA Substance Registry System
D-arabino-Hexose, 2-deoxy- (154-17-6)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25-37/39-36-26
WGK Germany 
3
RTECS 
MQ3325000
3-10
TSCA 
Yes
HS Code 
29400090
Hazardous Substances Data
154-17-6(Hazardous Substances Data)

MSDS

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2-Deoxy-D-glucose Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical]

Safety Profile

Poison by subcutaneous route. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

Purification Methods

Crystallise 2-deoxy--D-glucose from MeOH/Me2CO, Me2CO or butanone to give a mixture of  and  anomers, m 142-144o, [] 18 +38o (35minutes) to +46o (c 0.5, H2O). Recrystallisation from isoPrOH gives mainly the -anomer m 134-136o , [ ] D +156o to +103o (c 0.9, pyridine). 1H NMR studies showed that at 44o in D2O the solution contained 36% of -pyranose and 64% of -pyranose sugar, but furanose structures were undetectable. [Snowden & Fischer J Am Chem Soc 69 1048 1947, derivatives: Bollinger & Schmidt Helv Chim Acta 34 989 1951; see Angyal & Pickles Aust J Chem 25 1711 1972 for ratio of isomers in solution, Beilstein 1 IV 4282.]

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