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2-Deoxy-D-glucose

2-Deoxy-D-glucose Structure
2-Deoxy-D-glucose structure
CAS No.
154-17-6
Chemical Name:
2-Deoxy-D-glucose
Synonyms
2-dg;2-DEOXYGLUCOSE;deoxyglucose;2-Dexoy-D-Glucose;2-desoxy-d-glucose;D-Arabino-2-deoxyhexose;ba2758;D-2dGlc;Deoxy D;nsc15193
CBNumber:
CB0251338
Molecular Formula:
C6H12O5
Molecular Weight:
164.16
MDL Number:
MFCD00151328
MOL File:
154-17-6.mol
MSDS File:
SDS
Last updated:2024-12-18 13:37:16
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2-Deoxy-D-glucose Properties

Melting point 146-147 °C(lit.)
alpha 45.5 º (c=2, H2O)
Boiling point 211.61°C (rough estimate)
Density 1.1738 (rough estimate)
refractive index 46.5 ° (C=1, H2O)
storage temp. 2-8°C
solubility H2O: 50 mg/mL, clear, colorless to faintly yellow
pka pK1:12.52 (25°C)
form crystalline
color white
optical activity +38.5 → +45.9
Water Solubility Soluble in water.
Merck 14,2904
BRN 1723331
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day.
InChIKey PMMURAAUARKVCB-CEZCPVKQSA-N
LogP -1.460 (est)
CAS DataBase Reference 154-17-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 9G2MP84A8W
EPA Substance Registry System D-arabino-Hexose, 2-deoxy- (154-17-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazard Codes  Xn,Xi
Risk Statements  20/21/22-36/37/38
Safety Statements  24/25-37/39-36-26
WGK Germany  3
RTECS  MQ3325000
F  3-10
TSCA  Yes
HS Code  29400090
Hazardous Substances Data 154-17-6(Hazardous Substances Data)
NFPA 704
1
0 0

2-Deoxy-D-glucose price More Price(75)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR9231 2-Deoxy-D-glucose certified reference material, TraceCERT? 154-17-6 100MG $458 2024-03-01 Buy
Sigma-Aldrich D3179 2-Deoxy-D-glucose BioXtra, ≥98% 154-17-6 1g $253 2024-03-01 Buy
TCI Chemical D0051 2-Deoxy-D-glucose >97.0%(GC) 154-17-6 1g $47 2024-03-01 Buy
TCI Chemical D0051 2-Deoxy-D-glucose >97.0%(GC) 154-17-6 5g $140 2024-03-01 Buy
Alfa Aesar L07338 2-Deoxy-D-glucose, 98% 154-17-6 1g $66.4 2024-03-01 Buy
Product number Packaging Price Buy
PHR9231 100MG $458 Buy
D3179 1g $253 Buy
D0051 1g $47 Buy
D0051 5g $140 Buy
L07338 1g $66.4 Buy

2-Deoxy-D-glucose Chemical Properties,Uses,Production

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

Chemical Properties

white to light yellow crystal powde

Uses

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.

Uses

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.

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]

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.

Safety Profile

Poison by subcutaneous route. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.

storage

Store at +4°C

Purification Methods

Crystallise 2-deoxy--D-glucose from MeOH/Me2CO, Me2CO or butanone to give a mixture of  and  anomers, m 142-144o, [] 18 +38o (35minutes) to +46o (c 0.5, H2O). Recrystallisation from isoPrOH gives mainly the -anomer m 134-136o , [ ] D +156o to +103o (c 0.9, pyridine). 1H NMR studies showed that at 44o in D2O the solution contained 36% of -pyranose and 64% of -pyranose sugar, but furanose structures were undetectable. [Snowden & Fischer J Am Chem Soc 69 1048 1947, derivatives: Bollinger & Schmidt Helv Chim Acta 34 989 1951; see Angyal & Pickles Aust J Chem 25 1711 1972 for ratio of isomers in solution, Beilstein 1 IV 4282.]

References

1) Ralser et al., (2008), A catabolic blockade does not sufficiently explain how 2-deoxy-D-glucose inhibits cell growth; Proc. Natl. Acad. Sci. USA 105 17807 2) Giammarioli et al. (2012), Differential effects of the glycolysis inhibitor 2-deoxy-D-glucose on the activity of pro-apoptotic agents in metastatic melanoma cells; Int. J. Cancer, 131 e337

2-Deoxy-D-glucose synthesis

124266-48-4
154-17-6
Synthesis of 2-Deoxy-D-glucose from D-threo-Hexos-5-ulose, cyclic 1-(1,3-propanediyl acetal) (9CI)

2-Deoxy-D-glucose Preparation Products And Raw materials

Raw materials

D-threo-Hexos-5-ulose, cyclic 1-(1,3-propanediyl acetal) (9CI) D-arabino-Hexose, 2-deoxy-, cyclic 1,3-propanediyl acetal (9CI) D-arabino-Heptose, 2,3-dideoxy-4,5:6,7-bis-O-(1-methylethylidene)-

Preparation Products

2-Deoxy-D-glucose Suppliers

Global( 616)Suppliers
Supplier Tel Email Country ProdList Advantage
Hangzhou Hyper Chemicals Limited 		+86-0086-57187702781 +8613675893055 info@hyper-chem.com China 295 58
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29880 58
Beijing Ribio Biotech Co.,Ltd
010-62664360 +8613328773880 wucy@ribio.com.cn China 117 58
Shanghai Yongzeng Technology Co.,Ltd
+86-021-65281118 +86-13818947575 sales@yongzchem.com China 138 58
Hebei Weibang Biotechnology Co., Ltd 		+8615531157085 abby@weibangbio.com China 8810 58
Hebei Chuanghai Biotechnology Co,.LTD 		+86-13131129325 sales1@chuanghaibio.com China 5889 58
Henan Bao Enluo International TradeCo.，LTD 		+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2472 58
Hebei Kangcang new material Technology Co., LTD 		+8615713292910 Nancy@kangcang.com.cn China 341 58
Hebei Saisier Technology Co., LTD 		+86-18400010335 +86-18034520335 admin@hbsaisier.cn China 1015 58
Hebei Zhuanglai Chemical Trading Co.,Ltd 		+8613343047651 admin@zlchemi.com China 3002 58
Supplier Advantage
Hangzhou Hyper Chemicals Limited 		58
career henan chemical co
58
Beijing Ribio Biotech Co.,Ltd
58
Shanghai Yongzeng Technology Co.,Ltd
58
Hebei Weibang Biotechnology Co., Ltd 		58
Hebei Chuanghai Biotechnology Co,.LTD 		58
Henan Bao Enluo International TradeCo.，LTD 		58
Hebei Kangcang new material Technology Co., LTD 		58
Hebei Saisier Technology Co., LTD 		58
Hebei Zhuanglai Chemical Trading Co.,Ltd 		58

Related articles

View Lastest Price from 2-Deoxy-D-glucose manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Deoxy-D-Glucose pictures 2024-12-23 2-Deoxy-D-Glucose
154-17-6
 US $85.00-35.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
2-Deoxy-D-glucose pictures 2024-12-20 2-Deoxy-D-glucose
154-17-6
 US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
2-Deoxy-D-glucose pictures 2024-12-19 2-Deoxy-D-glucose
154-17-6
 US $6.00 / kg 1kg More than 99% 2000KG/Month Hebei Longbang Technology Co., Ltd
  • 2-Deoxy-D-Glucose pictures
  • 2-Deoxy-D-Glucose
    154-17-6
  • US $85.00-35.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd

2-Deoxy-D-glucose Spectrum

2-Deoxy-D-glucose(154-17-6)MS2-Deoxy-D-glucose(154-17-6)1HNMR2-Deoxy-D-glucose(154-17-6)IR12-Deoxy-D-glucose(154-17-6)IR22-Deoxy-D-glucose(154-17-6)Raman

154-17-6(2-Deoxy-D-glucose)Related Search:

Chenodeoxycholic acid D(+)-Glucose Desogestrel CORN SYRUP D-Glucose monohydrate
Ursodeoxycholic acid Glucose oxidase L-GLUCOSE METHYL BETA-D-GLUCOPYRANOSIDE Phlorizin
D-METHAMPHETAMINE DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* (-)-2-[METHYLAMINO]-1-PHENYLPROPANE HELICIN 2'-NITROPHENYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
LIQUID GLUCOSE ALPHA-D-GALACTOSE-1-PHOSPHATE DIPOTASSIUM SALT DIHYDRATE Maltitol

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2-deoxy-d-arabino-hexos 2-deoxy-d-glucos 2-deoxy-d-mannose 2-deoxy-glucos D-2-GLUCODESOSE 2-DEOXY-D-GLUCOSE GRADE III F&D VERSION 2-DEOXY-D-GLUCOSE, 99%, MIXTURE OF ANOMERS 6-HYDROXYMETHYL-5-METHYL-TETRAHYDRO-PYRAN-2,4,5-TRIOL 2-Deoxy-D-Glucose,2-Dg 2-Deoxy-D-Glucose98.0-100.0% D-arabino-Hexose, 2-deoxy- 2-DEOXY-D-GLUCOSE,REAGENT DEOXY-D-GLUCOSE, 2-(P) 2-DEOXY-D-ARABINOHEXOSE 2-DEOXY-D-GLUCOSE 2-Deoxy-D-Arabino 2-deoxy-D-glucose grade ii 2-deoxy-D-glucose grade iii 2-deoxy-D-glucose sigmaultra 2-deoxy-D-glucose, mixture of anomers 2-DEOXY-D-GLUCOSE extrapure (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal 2-Deoxy-D-glucose,99% ba2758 d-2-deoxyglucose DEOXY-D-GLUCOSE, 2-(RG) nsc15193 DEOXY-D-GLUCOSE,2- 2-Deoxy-D-glucose,2-Deoxy-D-arabinohexose D-Arabino-2-desoxyhexose (4R,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol 2-Deoxy-D-Glucose (100 mg) (AS) 2-deoxy-d-[UL-13C6]glucose D-2dGlc D-arabino-Hexopyranose, 2-deoxy- D-arabino-Hexose, 2-deoxy- (6CI,8CI,9CI) 2-Deoxy-D-glucose, >=98% (4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol 2-DEOXY-D-GLUCOSE >= 98% (GC), CRYST 2-Deoxy-D-Glucose (100 mg) 2-Deoxy-D-glucose, Min. 98% 2-DG, 2-Deoxy-D-glucose 2-Dexoy-D-Glucose 98% (2-DG) 2-Deoxy-D-glucose > Deoxy D 2-Deoxy- D -g 2-Deoxy- D -gL 2-Deoxy-D-glucose USP/EP/BP 2-deoxy-dextro-glucose Hot Sell 2-Deoxyglucose 2-Deoxy-D-Glucose CAS 154-17-6 2-Dg 2-Deoxyglucose Powder 2-Deoxy-D-GlucoseQ: What is 2-Deoxy-D-Glucose Q: What is the CAS Number of 2-Deoxy-D-Glucose Q: What is the storage condition of 2-Deoxy-D-Glucose 2-Deoxy-D-Glucose (2-DG) extrapure AR, 99.9% 2-desoxy-d-glucose 2-DEOXYGLUCOSE 2-dg deoxyglucose D-Arabino-2-deoxyhexose 2-Dexoy-D-Glucose