2-Deoxy-D-glucose
- Iupac Name:(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
- CAS No.: 154-17-6
- Molecular Weight:164.16
- Modify Date.: 2022-10-31 16:22
- Introduction: 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]
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1. Names and Identifiers
- 1.1 Name
- 2-Deoxy-D-glucose
- 1.2 Synonyms
2 DG 2-Deoxy-D-arabino-hexose 2-Deoxy-D-mannose 2-Deoxyglucose 2-Desoxy-D-glucose 2-DG Ba 2758 D-arabino-Hexose, 2-deoxy- Deoxyglucose D-Glucose, 2-deoxy- NSC 15193
- 1.3 CAS No.
- 154-17-6
- 1.4 CID
- 108223
- 1.5 EINECS(EC#)
- 205-823-0
- 1.6 Molecular Formula
- C6H12O5 (isomer)
- 1.7 Inchi
- 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
- 1.8 InChkey
- VRYALKFFQXWPIH-PBXRRBTRSA-N
- 1.9 Canonical Smiles
- C(C=O)C(C(C(CO)O)O)O
- 1.10 Isomers Smiles
- C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
2. Properties
- 2.1 Density
- 1.1738 (rough estimate)
- 2.1 Melting point
- 146-147 °C(lit.)
- 2.1 Boiling point
- 211.61°C (rough estimate)
- 2.1 Refractive index
- 46.5 ° (C=1, H2O)
- 2.1 Flash Point
- 202.3 °C
- 2.1 Precise Quality
- 164.06800
- 2.1 PSA
- 97.99000
- 2.1 logP
- -2.34960
- 2.1 Solubility
- H2O: 50?mg/mL, clear, colorless to faintly yellow
- 2.2 Appearance
- white powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- white to light yellow crystal powde
- 2.5 Color/Form
- crystalline
- 2.6 pKa
- pK1:12.52 (25°C)
- 2.7 Water Solubility
- Soluble in water.
- 2.8 Spectral Properties
- IR: 2:108B (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 10:91C (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
- 2.9 Stability
- Stable under normal temperatures and pressures.
- 2.10 StorageTemp
- 0-6°C
3. Use and Manufacturing
- 3.1 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.] 2-Deoxy-D-glucoseSupplier
- 3.2 Usage
- 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]
4. Safety and Handling
- 4.1 Hazard Codes
- Xi,Xn
- 4.1 Risk Statements
- 20/21/22-36/37/38
- 4.1 Safety Statements
- 24/25-37/39-36-26
- 4.1 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.
- 4.2 WGK Germany
- 3
- 4.2 RTECS
- MQ3325000
- 4.2 Report
-
Reported in EPA TSCA Inventory.
- 4.3 Safety
-
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.
Hazard Codes:?
Xn,Xi
Risk Statements: 20/21/22-36/37/38?
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: 24/25-37/39-36-26?
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
- 4.4 Specification
-
?2-Deoxy-D-glucose , its cas register number is . It also can be called Deoxyglucose ; 2-DG ; 2-Deoxy-D-arabino-hexose ; 2-Deoxy-D-glucose ; 2-Deoxy-D-mannose ; 2-Desoxy-D-glucose ; D-2-Deoxyglucose ; D-Arabino-hexose, 2-deoxy- ; D-Glucose, 2-deoxy- .It is a white to light yellow crystal powder.It?is uptaken by the glucose transporters of the cell.
- 4.5 Toxicity
-
Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
rat |
LD50 |
intraperitoneal |
2gm/kg (2000mg/kg) |
? |
Journal of Pharmacy and Pharmacology. Vol. 17, Pg. 814, 1965. |
rat |
LD50 |
subcutaneous |
250mg/kg (250mg/kg) |
? |
Annales Pharmaceutiques Francaises. Vol. 39, Pg. 327, 1981. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
Pictogram(s) | No symbol. |
Signal word | No signal word. |
Hazard statement(s) | none |
Precautionary statement(s) | |
Prevention | none |
Response | none |
Storage | none |
Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Other Information
- 7.0 Usage
- 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.
8. Computational chemical data
- Molecular Weight: 164.16g/mol
- Molecular Formula: C6H12O5
- Compound Is Canonicalized: True
- XLogP3-AA: -2.9
- Exact Mass: 164.06847348
- Monoisotopic Mass: 164.06847348
- Complexity: 116
- Rotatable Bond Count: 5
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 5
- Topological Polar Surface Area: 98
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 3
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAIAAAAAAgAIAAgQgAAAAAAAAAAAAAEAAAABEBYAAAAAQAAFIAABAAHKTABAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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