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D6134

Sigma-Aldrich

2-Deoxy-D-glucose

≥99% (GC), crystalline

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

biological source

synthetic (organic)

Quality Level

Assay

≥99% (GC)

form

crystalline

technique(s)

gas chromatography (GC): suitable

color

white

mp

146-147 °C (lit.)

solubility

H2O: soluble 330 mg/mL, clear, colorless

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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This Item
D8375D3179PHR9231
2-Deoxy-D-glucose ≥99% (GC), crystalline

Sigma-Aldrich

D6134

2-Deoxy-D-glucose

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

Sigma-Aldrich

D8375

2-Deoxy-D-glucose

-
2-Deoxy-D-glucose BioXtra, ≥98%

Sigma-Aldrich

D3179

2-Deoxy-D-glucose

Premium Grade
2-Deoxy-D-glucose certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

PHR9231

2-Deoxy-D-glucose

-
assay

≥99% (GC)

assay

≥98% (GC)

assay

≥98%

assay

-

form

crystalline

form

crystalline

form

powder

form

-

technique(s)

gas chromatography (GC): suitable

technique(s)

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

technique(s)

gas chromatography (GC): suitable

technique(s)

-

color

white

color

white to off-white

color

white

color

-

mp

146-147 °C (lit.)

mp

146-147 °C (lit.)

mp

146-147 °C (lit.)

mp

146-147 °C (lit.)

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.

Preparation Note

A further purification of the Grade II material by recrystallization.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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