ChemicalBook > CAS DataBase List > 2-Deoxy-D-glucose

2-Deoxy-D-glucose

Product Name
2-Deoxy-D-glucose
CAS No.
154-17-6
Chemical Name
2-Deoxy-D-glucose
Synonyms
2-dg;2-DEOXYGLUCOSE;deoxyglucose;2-Dexoy-D-Glucose;2-desoxy-d-glucose;D-Arabino-2-deoxyhexose;ba2758;D-2dGlc;Deoxy D;nsc15193
CBNumber
CB0251338
Molecular Formula
C6H12O5
Formula Weight
164.16
MOL File
154-17-6.mol
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2-Deoxy-D-glucose Property

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. 
2-8°C
solubility 
H2O: 50 mg/mL, clear, colorless to faintly yellow
form 
crystalline
pka
pK1:12.52 (25°C)
color 
white
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
D-arabino-Hexose, 2-deoxy- (154-17-6)
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Safety

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
F 
3-10
TSCA 
Yes
HS Code 
29400090
Hazardous Substances Data
154-17-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR9231
Product name
2-Deoxy-D-glucose
Purity
certified reference material, TraceCERT?
Packaging
100MG
Price
$458
Updated
2024/03/01
Sigma-Aldrich
Product number
D3179
Product name
2-Deoxy-D-glucose
Purity
BioXtra, ≥98%
Packaging
1g
Price
$253
Updated
2024/03/01
TCI Chemical
Product number
D0051
Product name
2-Deoxy-D-glucose
Purity
>97.0%(GC)
Packaging
1g
Price
$47
Updated
2024/03/01
TCI Chemical
Product number
D0051
Product name
2-Deoxy-D-glucose
Purity
>97.0%(GC)
Packaging
5g
Price
$140
Updated
2024/03/01
Alfa Aesar
Product number
L07338
Product name
2-Deoxy-D-glucose, 98%
Packaging
1g
Price
$66.4
Updated
2024/03/01
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2-Deoxy-D-glucose Chemical Properties,Usage,Production

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]

Uses

2-Deoxy-D-glucose is act as a culture media part in molecular genetics and as a targeted optical imaging agent for fluorescent in vivo imaging. It finds an application in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). It is utilized in the development of anti-cancer approaches like oxidative stress, radio and chemosensitization.

Uses

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.

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.

storage

Store at +4°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

2-Deoxy-D-glucose Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-Deoxy-D-glucose manufacturers

Hebei Kangcang new material Technology Co., LTD
Product
2-Deoxy-D-glucose 154-17-6
Price
US $100.00/g
Min. Order
1g
Purity
98%
Supply Ability
20ton
Release date
2024-03-27
Hebei Saisier Technology Co., LTD
Product
2-Deoxy-D-glucose 154-17-6
Price
US $6.00/KG
Min. Order
25KG
Purity
MORE THAN 99%
Supply Ability
20TONS
Release date
2024-03-27
Hebei Jingbo New Material Technology Co., Ltd
Product
2-Deoxy-D-glucose 154-17-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000000
Release date
2023-11-24

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