2-deoxy-D-glucose

Base Information

• Chemical Name: 2-deoxy-D-glucose
• CAS No.: 154-17-6
• Deprecated CAS: 2092-72-0,3724-71-8,4825-30-3,7640-18-8,3724-71-8,4825-30-3,7640-18-8
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 29400090
• European Community (EC) Number: 205-823-0
• UNII: 9G2MP84A8W
• DSSTox Substance ID: DTXSID1037648
• Nikkaji Number: J59.831C
• Wikipedia: 2-Deoxy-D-glucose
• Wikidata: Q3266534
• NCI Thesaurus Code: C116618
• Metabolomics Workbench ID: 151939
• ChEMBL ID: CHEMBL2074932
• Mol file: 154-17-6.mol

Synonyms:2 Deoxy D glucose;2 Deoxyglucose;2 Desoxy D glucose;2-Deoxy-D-glucose;2-Deoxyglucose;2-Desoxy-D-glucose;Deoxyglucose

Chemical Property of 2-deoxy-D-glucose

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.8E-08mmHg at 25°C
• Melting Point: 146-147 °C(lit.)
• Refractive Index: 46.5 ° (C=1, H2O)
• Boiling Point: 411 °C at 760 mmHg
• PKA: pK1:12.52 (25°C)
• Flash Point: 202.3 °C
• PSA: 97.99000
• Density: 1.533 g/cm³
• LogP: -2.34960
• Storage Temp.: 0-6°C
• Solubility.: H2O: 50 mg/mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in water.
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

2-Deoxy-D-glucose 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C=O)C(C(C(CO)O)O)O
• Isomeric SMILES: C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Recent ClinicalTrials: Pharmacokinetics Study of Oral 2-Deoxy-D-Glucose (2DG) in Subjects With a Confirmed Diagnosis of Epilepsy
• Description: 2-Deoxy-D-glucose (154-17-6) is a synthetic glucose analog with extensive biological effects. It is commonly thought of as an inhibitor of glycolysis, but its metabolic effects are wide-ranging. 2-Deoxy-D-glucose competitively inhibits glucose uptake via its metabolite 2-Deoxy-D-glucose-6-phosphate, which inhibits hexokinase and phosphoglucose-isomerase leading to decreased ATP production, cell cycle blockage, decreased cell growth and ultimately cell death.1,2
• Uses: 2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical] 2-Deoxy-D-glucose is act as a culture media part in molecular genetics and as a targeted optical imaging agent for fluorescent in vivo imaging. It finds an application in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). It is utilized in the development of anti-cancer approaches like oxidative stress, radio and chemosensitization. 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.

Technology Process of 2-deoxy-D-glucose

There total 37 articles about 2-deoxy-D-glucose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2R,3S,4R)-5-[1,3]Dioxan-2-yl-pentane-1,2,3,4-tetraol (124266-10-0) → D-2-deoxyglucose (154-17-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1021/ja00208a046

Reference yield: 73.0%

2-deoxy-4,5-O-isopropylidene-D-arabino-hexose dimethyl acetal (73982-69-1) → D-2-deoxyglucose (154-17-6)

Guidance literature:

With trifluoroacetic acid; at 4 ℃; for 24h;

DOI:10.1016/S0008-6215(00)85317-3

Reference yield: 65.0%

2,3-Dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-heptose (149180-91-6) → D-2-deoxyglucose (154-17-6)

Guidance literature:

With formic acid; In ethanol; at 90 ℃; for 0.166667h;

DOI:10.1016/S0008-6215(00)90096-X

upstream raw materials:

O³,O⁴,O⁶-triacetyl-O¹-benzoyl-2-bromo-2-deoxy-α-D-glucopyranose

O³,O⁴,O⁶-triacetyl-O¹-benzoyl-2-iodo-2-deoxy-α-D-glucopyranose

2-deoxy-D-arabino-hexopyranose

2-deoxy-4,5-O-isopropylidene-D-arabino-hexose dimethyl acetal

Downstream raw materials:

N-phenyl-β-D-arabino-2-deoxy-hexopyranosylamine

methyl 2-deoxy-α-D-arabino-hexofuranoside

(2R,3S,4R)-6,6-Bis-(4-methoxy-phenyl)-hexane-1,2,3,4-tetraol

2,3,4,6-tetra-O-benzyl-5-deoxy-aldehydo-D-lyxo-hexose

Refernces

• 1、 Borysenko,Spaltenstein,Straub,Whitesides. "Synthesis of aldose sugars from half-protected dialdehydes using rabbit muscle aldolase". . p. 9275 - 9276. Retrieved 1989.
• 2、 Pieri, Valerio,Schwaiger, Stefan,Ellmerer, Ernst P.,Stuppner, Hermann. "Iridoid glycosides from the leaves of Sambucus ebulus". experimental part. p. 1798 - 1803. Retrieved 2010/03/26.
• 3、 Sauvage, Jean-Paul,Chapelle, Stella,Dona, Anne-Marie,Verchere, Jean-Francois. "Acyclic molybdate complexes of aldoses in the arabino and xylo series and their application to the determination of the proportion of acyclic forms in aqueous solution". . p. 293 - 306. Retrieved 2007/10/02.