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D6134

Sigma-Aldrich

2-Deoxy-D-glucose

≥99% (GC), crystalline

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
25972-M25972-MD3179
2-Deoxy-D-glucose ≥99% (GC), crystalline

Sigma-Aldrich

D6134

2-Deoxy-D-glucose

2-Deoxy-D-glucose Non-metabolizable derivative of glucose that can be carried by the glucose carrier in human erythrocytes. An indirect inhibitor of hexokinase. Reported to reduce the incidence of doxorubicin-induced apoptosis.

Millipore

25972-M

2-Deoxy-D-glucose

2-Deoxy-D-glucose Non-metabolizable derivative of glucose that can be carried by the glucose carrier in human erythrocytes. An indirect inhibitor of hexokinase. Reported to reduce the incidence of doxorubicin-induced apoptosis.

Millipore

25972-M

2-Deoxy-D-glucose

2-Deoxy-D-glucose BioXtra, ≥98%

Sigma-Aldrich

D3179

2-Deoxy-D-glucose

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

synthetic (organic)

assay

≥99% (GC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98%

form

crystalline

form

powder

form

powder

form

powder

technique(s)

gas chromatography (GC): suitable

technique(s)

-

technique(s)

-

technique(s)

gas chromatography (GC): suitable

color

white

color

off-white to white

color

off-white to white

color

-

mp

146-147 °C (lit.)

mp

-

mp

-

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.

Storage Class Code

13 - Non 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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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