EN
0
Home > Products > Specialty & Industrial Chemicals > Specialty Chemicals > 2-Deoxy-D-glucose
2-Deoxy-D-glucose structure, CAS 154-17-6

2-Deoxy-D-glucose

CAS Number154-17-6

Synonyms2-DEOXY-D-ARABINOHEXOSE; 2-Deoxy-D-arabino-hexose; 2-Deoxy-D-glucose; 2-deoxy-d-arabino-hexos; MFCD00151328; D-Arabino-2-deoxyhexose; EINECS 205-823-0

Molecular FormulaC6H12O5

Molecular Weight164.16

Purity≥98 (GC)%

Density1.4±0.1 g/cm3

Boiling Point456.7±45.0 °C at 760 mmHg

Melting Point146-147 °C (lit.)

Flash Point

Appearancecrystalline

EINECS205-823-0

MSDSChineseEnglish

SymbolTransport

Signal WordWarning

Cat. No.: 2A-9003057 Purity: ≥98 (GC)%
Change View

Please Login or Create an Account to: See VlP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

Inquiry

Quality Control of [ 154-17-6 ] Purity: ≥98 (GC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number154-17-6
Catalog No.2A-9003057
Chinese Name2-脱氧-D-葡萄糖
Synonyms2-DEOXY-D-ARABINOHEXOSE; 2-Deoxy-D-arabino-hexose; 2-Deoxy-D-glucose; 2-deoxy-d-arabino-hexos; MFCD00151328; D-Arabino-2-deoxyhexose; EINECS 205-823-0
Molecular FormulaC6H12O5
Molecular Weight164.16
Purity≥98 (GC)
Density1.4±0.1 g/cm3
Boiling Point456.7±45.0 °C at 760 mmHg
Melting Point146-147 °C (lit.)
Appearancecrystalline
Storage Condition2~8℃
Application2-Deoxy-D-glucose is a glucose analog and a glucose metabolism inhibitor that inhibits glycolysis by acting on hexokinase.
EINECS205-823-0
HTC2912491000
PubChem ID24894205
MDL NumberMFCD00151328
SMILESOC[C@@H](O)[C@@H](O)[C@H](O)CC=O
InChI1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
InChI KeyVRYALKFFQXWPIH-PBXRRBTRSA-N
Beilstein/REAXYS1723331
NACRES CodeNA.25
UNSPSC12352201
Hazard SymbolsTransport
MSDSmsds/3057_1_154_17_6.pdf
Bioactivity2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Hexokinase Research Areas >> Cancer In Vitro 2-Deoxy-D-glucose (2-DG, 4, 8, or 16 mM) significantly reduces the level of ATP in MCF-7 cells in a dose- and time-dependent manner that paralleles the effects of 2-DG on cell growth. The levels of phosphorylated Akt are significantly decreased, whereas the levels of phosphorylated AMPK and Sirt-1 are significantly increased in MCF-7 cells exposed to 2-Deoxy-D-glucose at 4, 8, or 16 mM for 1, 3, or 5 days in a dose- and time-dependent manner[1]. 2-DG treatment increases the levels of pentose phosphate pathway (PPP) metabolites and augments the generation of NADPH by glucose-6-phosphate dehydrogenase. An increase in NADPH and upregulation of glutathione synthetase expression resultes in the increase in the reduced form of glutathione by 2-DG in NB4 cells[3]. In Vivo 2-Deoxy-D-glucose (0.03%, w/w) causes a 7% decrease in final weight that is statistically significant, and delayes the appearance of palpable mammary carcinomas[1]. 2-Deoxy-D-glucose (3 mmol/kg, i.v.) is decreased in a dose-dependent manner by insulin in rat muscle[2]. Cell Assay The effect of 2-DG on cell growth is determined by evaluating the number of adherent cells. Briefly, MCF-7 cells are plated at 3×104 cells per well in flat-bottomed 96-well plates in 100 μL of culture medium under the culture conditions. After 24 hours, cells are fed with fresh medium including 2-Deoxy-D-glucose at doses of 0, 4, 8, or 16 mM. At days 1, 3, and 5 after 2-Deoxy-D-glucose exposure, cells are fixed with 1% glutaraldehyde, replaced with PBS, and stored at 4°C. At the end of an experiment, all of the plates are stained with 0.02% aqueous crystal violet for 30 minutes and rinsed with deionized water. After redissolving the bound crystal violet in 70% ethanol, the absorbance is determined at 590 nm using a SPECTRA MAX PLUS Microplate Spectrophotometer System. Animal Admin At 21 days of age, rats are injected with 50 mg 1-methyl-1-nitrosourea per kilogram of body weight (i.p.). Rats are housed two per cage in solid-bottomed polycarbonate cages equipped with a food cup. Six days following carcinogen injection, all rats are randomized into one of three groups, 30 rats per group, and are fed ad libitum AIN-93G diet containing 0.0%, 0.02%, or 0.03% (w/w) 2-Deoxy-D-glucose (2-DG) for 5 weeks. Animal rooms are maintained at 22±1°C with 50% relative humidity and a 12-hour light/12-hour dark cycle. Rats are weighed thrice per week and are palpated for detection of mammary tumors twice per week starting from 19 days postcarcinogen. References [1]. Zhu Z, et al. 2-Deoxyglucose as an energy restriction mimetic agent: effects on mammary carcinogenesis and on mammary tumor cell growth in vitro. Cancer Res. 2005 Aug 1;65(15):7023-30. [2]. Ueyama A, et al. Nonradioisotope assay of glucose uptake activity in rat skeletal muscle using enzymatic measurement of 2-deoxyglucose 6-phosphate in vitro and in vivo. Biol Signals Recept. 2000 Sep-Oct;9(5):267-74. [3]. Miwa H, et al. Leukemia cells demonstrate a different metabolic perturbation provoked by 2-deoxyglucose. Oncol Rep. 2013 May;29(5):2053-7. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 456.7±45.0 °C at 760 mmHg Melting Point 146-147ºC Molecular Formula C6H12O5 Molecular Weight 164.156 Flash Point 244.1±25.2 °C Exact Mass 164.068466 PSA 97.99000 LogP -3.07 Vapour Pressure 0.0±2.5 mmHg at 25°C Index of Refraction 1.534 InChIKey VRYALKFFQXWPIH-PBXRRBTRSA-N SMILES O=CCC(O)C(O)C(O)CO Storage condition 2~8℃
Use of2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase. Properties Articles193 Name 2-Deoxy-D-Glucose Synonym More Synonyms 2-Deoxy-D-glucose Biological Activity Description 2-Deoxy-D-glucose is a glucose analog that acts as a competitive inhibitor of glucose metabolism, inhibiting glycolysis via its actions on hexokinase. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Hexokinase Research Areas >> Cancer References [1]. Zhu Z, et al. 2-Deoxyglucose as an energy restriction mimetic agent: effects on mammary carcinogenesis and on mammary tumor cell growth in vitro. Cancer Res. 2005 Aug 1;65(15):7023-30. [2]. Ueyama A, et al. Nonradioisotope assay of glucose uptake activity in rat skeletal muscle using enzymatic measurement of 2-deoxyglucose 6-phosphate in vitro and in vivo. Biol Signals Recept. 2000 Sep-Oct;9(5):267-74. [3]. Miwa H, et al. Leukemia cells demonstrate a different metabolic perturbation provoked by 2-deoxyglucose. Oncol Rep. 2013 May;29(5):2053-7. Chemical & Physical Properties Molecular Formula C6H12O5 Exact Mass 164.068466 PSA 97.99000 LogP -3.07 Index of Refraction 1.534 InChIKey VRYALKFFQXWPIH-PBXRRBTRSA-N SMILES O=CCC(O)C(O)C(O)CO Storage condition 2~8℃
Tax Rebate13.0%
SupervisionNone. MFN tariff: 5.5%. Ordinary tariff: 30.0%
Transport InfoProduct name: Purity: 98.0%
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available
Related Products in Specialty Chemicals
2-Cyanobenzoic acid3839-22-32A-9003040
2-Cyanobenzotrifluoride447-60-92A-9003041
2-Cyanomethyl benzoic acid ethyl ester2A-1030422A-9003042
2-Cyanophenol611-20-12A-9003043
2-Decyne2384-70-52A-9003048
2-Deoxy-D-ribose533-67-52A-9003058
2-Deoxy-L-ribose18546-37-72A-9003062
2-Diacetylamino-3,5-dibromobenzyl bromide2A-1030642A-9003064
2-Diethylaminoethanethiol100-38-92A-9003065
2-Ethoxy-4-nitrobenzoic acid2486-66-02A-9003069
Browse all Specialty Chemicals products »
Contact Us

Phone:

630-322-8886

630-322-8887

Email:

[email protected]

Office Locations:

Chicago, IL, USA

San Francisco, CA, USA