(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal

• ChemBase ID: 105767
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: O=CC[C@@H](O)[C@H](O)[C@H](O)CO
• Canonical SMILES: O=CC[C@H]([C@@H]([C@@H](CO)O)O)O
• 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
• InChIKey: VRYALKFFQXWPIH-PBXRRBTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
• IUPAC Traditional name: deoxyglucose
• Synonyms: 2-Deoxy-D-glucose; 2-Deoxyglucose; 2-Deoxy-D-arabinohexose; 2-Deoxy-d-Arabino-hexose; 2-Deoxy-3-Arabino-hexose; 2-DEOXY-D-GLUCOSE; 2-脱氧-D-葡糖; D-2-脱氧葡萄糖

Database IDs

• CAS Number: 154-17-6
• EC Number: 205-823-0
• MDL Number: MFCD00151328
• Beilstein Number: 1723331
• PubChem SID: 24893732; 24894205; 24894000; 162088980
• PubChem CID: 108223

CALCULATED PROPERTIES

• Acid pKa: 12.838305
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.853202
• LogD (pH = 7.4): -2.8532038
• Log P: -2.853202
• Molar Refractivity: 36.0074 cm^3
• Polarizability: 14.534815 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Do you have solubility information on this product that you would like to share?; H2O: soluble1 M at 20 °C, clear, colorless; H2O: soluble50 mg/mL, clear, colorless to faintly yellow
• Apperance: white crystalline; white to off-white crystalline
• Melting Point: 146-147 °C(lit.); 146-147°C; 148-153 °C
• Optical Rotation: [α]20/D +46.5±2°, 45 hr, c = 0.5% in H2O; [α]21/D +46.5°, c = 1 in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: MQ3325000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%; ≥98% (GC); ≥98.0% (HPLC); ≥99% (GC); 97%; 99%
• Ignition Residue: <0.1%
• Impurities: <0.1% Insoluble matter; ≤0.001% Phosphorus (P)
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.003%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Empirical Formula (Hill Notation): C6H12O5

DETAILS

MP Biomedicals - 02194028

White crystals
Purity: 99%
For use as a culture media component for molecular genetics.

Sigma Aldrich - D8375

Application
Do you have application information on this product that you would like to share?
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.?
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.1
包装
10 mg in autosmp vl

Sigma Aldrich - D3179

Application
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.1

Sigma Aldrich - D6134

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
包装
1, 5, 25 g in poly bottle
250 mg in poly bottle
Preparation Note
A further purification of the Grade II material by recrystallization.
Application
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.1

Sigma Aldrich - D4601

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.1

Sigma Aldrich - 31060

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.1