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D8375

Sigma-Aldrich

2-Deoxy-D-glucose

≥98% (GC), crystalline

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Synonym(s):
2-Deoxyglucose, 2-Deoxy-D-arabinohexose
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein/REAXYS Number:
1723331
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic

Quality Level

assay

≥98% (GC)

form

crystalline

technique(s)

gas chromatography (GC): suitable
inhibition assay: suitable

color

white to off-white

mp

146-147 °C (lit.)

solubility

H2O: 0.250 g/5mL

application(s)

clinical research
life science and biopharma
metabolomics

storage temp.

2-8°C

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)CC=O

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

InChI key

VRYALKFFQXWPIH-PBXRRBTRSA-N

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1 of 4

This Item
D6134D3179M0285
2-Deoxy-D-glucose ≥98% (GC), crystalline

D8375

2-Deoxy-D-glucose

-
2-Deoxy-D-glucose ≥99% (GC), crystalline

D6134

2-Deoxy-D-glucose

-
2-Deoxy-D-glucose ≥98% (GC), BioXtra

D3179

2-Deoxy-D-glucose

Premium Grade
Methyl-β-D-galactopyranoside

M0285

Methyl-β-D-galactopyranoside

-
technique(s)

gas chromatography (GC): suitable, inhibition assay: suitable

technique(s)

gas chromatography (GC): suitable

technique(s)

gas chromatography (GC): suitable

technique(s)

gas chromatography (GC): suitable

assay

≥98% (GC)

assay

≥99% (GC)

assay

≥98% (GC)

assay

≥98% (GC)

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

200

solubility

H2O: 0.250 g/5mL

solubility

H2O: soluble 330 mg/mL, clear, colorless

solubility

H2O: 1 M at 20 °C, clear, colorless

solubility

water: 50 mg/mL, clear, colorless

form

crystalline

form

crystalline

form

powder

form

powder

General description

2-Deoxy-D-glucose, a non-metabolizable glucose analogue, disrupts glycolysis by targeting hexokinase, the rate-limiting step in glycolysis. Phosphorylated to 2-DG-P by hexokinase, it accumulates in the cell, depleting cellular ATP. This approach, effective in starving and killing cancer cells, may also inhibit virus cells reliant on glycolysis for replication. This versatile molecule finds application in cancer, virology, metabolomics and biochemical research.

Application

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.

Features and Benefits

  • High-purity compound suitable for a wide variety of research applications

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

For additional information on our range of Biochemicals, please complete this form.
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

comparable product

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Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Proceedings of the National Academy of Sciences of the United States of America, 110(22), 8790-8794 (2013-05-15)
Single-cell level measurements are necessary to characterize the intrinsic biological variability in a population of cells. In this study, we demonstrate that, with the microarrays for mass spectrometry platform, we are able to observe this variability. We monitor environmentally (2-deoxy-D-glucose)
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Articles

We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.

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