| Identification | More | [Name]
2-Deoxy-D-glucose | [CAS]
154-17-6 | [Synonyms]
2-DEOXY-D-ARABINOHEXOSE
2-DEOXY-D-GLUCOSE
2-DEOXYGLUCOSE
D-2-GLUCODESOSE
D-Arabino-2-deoxyhexose
DEOXY-D-GLUCOSE,2-
2-deoxy-d-arabino-hexos
2-deoxy-d-glucos
2-deoxy-d-mannose
2-deoxy-glucos
2-desoxy-d-glucose
2-dg
ba2758
d-2-deoxyglucose
deoxyglucose
nsc15193
2-Deoxy-D-Arabino
2-deoxy-D-glucose grade ii
2-deoxy-D-glucose grade iii
2-deoxy-D-glucose sigmaultra | [EINECS(EC#)]
205-823-0 | [Molecular Formula]
C6H12O5 | [MDL Number]
MFCD00151328 | [Molecular Weight]
164.16 | [MOL File]
154-17-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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
| [form ]
crystalline
| [pka]
pK1:12.52 (25°C) | [color ]
white
| [optical activity]
+38.5 → +45.9 | [Water Solubility ]
Soluble in water. | [Merck ]
14,2904 | [BRN ]
1723331 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day. | [InChIKey]
PMMURAAUARKVCB-CEZCPVKQSA-N | [LogP]
-1.460 (est) | [CAS DataBase Reference]
154-17-6(CAS DataBase Reference) | [EPA Substance Registry System]
154-17-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
MQ3325000
| [F ]
3-10 | [TSCA ]
Yes | [HS Code ]
29400000 | [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. | [Hazardous Substances Data]
154-17-6(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Description]
2-Deoxy-D-glucose (154-17-6) is a synthetic glucose analog with extensive biological effects. It is commonly thought of as an inhibitor of glycolysis, but its metabolic effects are wide-ranging. 2-Deoxy-D-glucose competitively inhibits glucose uptake via its metabolite 2-Deoxy-D-glucose-6-phosphate, which inhibits hexokinase and phosphoglucose-isomerase leading to decreased ATP production, cell cycle blockage, decreased cell growth and ultimately cell death.1,2 | [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] | [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. | [storage]
Store at -20°C | [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.] | [References]
1) Ralser et al., (2008), A catabolic blockade does not sufficiently explain how 2-deoxy-D-glucose inhibits cell growth; Proc. Natl. Acad. Sci. USA 105 17807
2) Giammarioli et al. (2012), Differential effects of the glycolysis inhibitor 2-deoxy-D-glucose on the activity of pro-apoptotic agents in metastatic melanoma cells; Int. J. Cancer, 131 e337 |
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