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2'-Deoxyuridine

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CAS:951-78-0
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2'-Deoxyuridine manufacturers

  • 2′-deoxyuridine
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  • 2024-04-08
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  • 2'-Deoxyuridine
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  • 2023-09-06
  • CAS:951-78-0
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  • 2'-Deoxyuridine
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  • 2023-09-05
  • CAS:951-78-0
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2'-Deoxyuridine Basic information
Description Physical properties synthesis
Product Name:2'-Deoxyuridine
Synonyms:1-(2'-DEOXY-BETA-D-RIBOFURANOSYL)URACIL;1-(2-DEOXY-BETA-D-RIBOFURANOSYL)URACIL;(+)-2'-DEOXYURIDINE;2'-DEOXYURIDINE;DEOXYURIDINE-2';(+)-2'-DEOXYURIDINE, 99+%;Uracildeoxyr;1-(2-Deoxy-b-D-erythro-pentofuranosyl)uracil
CAS:951-78-0
MF:C9H12N2O5
MW:228.2
EINECS:213-455-7
Product Categories:API intermediates;Bases & Related Reagents;Carbohydrates & Derivatives;Heterocycles;Nucleotides;Pyridines, Pyrimidines, Purines and Pteredines;FINE Chemical & INTERMEDIATES;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Pharmaceutical Raw Materials;Heterocycle-Pyrimidine series;Pyrimidine purine;Pharmaceutical;951-78-0;Nucleosides;Modified(deoxy)nucleoside
Mol File:951-78-0.mol
2'-Deoxyuridine Structure
2'-Deoxyuridine Chemical Properties
Melting point 167-169 °C(lit.)
Boiling point 370.01°C (rough estimate)
alpha D22 +50° (c = 1.1 in N NaOH)
density 1.3705 (rough estimate)
refractive index 52 ° (C=1, 1mol/L NaOH)
storage temp. Inert atmosphere,2-8°C
solubility DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
pkapKa 9.3(H2O t = 25) (Uncertain)
form Powder
color White to off-white
Water Solubility 300 g/L (20 ºC)
Sensitive Air Sensitive
Merck 14,2910
BRN 24433
InChIKeyMXHRCPNRJAMMIM-ATRFCDNQSA-N
CAS DataBase Reference951-78-0(CAS DataBase Reference)
EPA Substance Registry SystemUridine, 2'-deoxy- (951-78-0)
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38
Safety Statements 22-24/25-37/39-36/37/39-26
WGK Germany 3
RTECS YU7490000
10-23
Hazard Note Air Sensitive
TSCA Yes
HS Code 29349990
MSDS Information
ProviderLanguage
2'-Deoxyuridine English
SigmaAldrich English
ACROS English
ALFA English
2'-Deoxyuridine Usage And Synthesis
Description2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used to prepare combined deoxynucleoside drugs or used as chemical reagents for biochemical research. At the same time, it can be used as an intermediate to synthesize some antiviral nucleoside drugs and molecular markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine.
Physical properties2'-Deoxyuridine is a white or off-white powdered solid with a melting point of 167 to 169 °C. Its boiling point is roughly estimated to be 370.01°C. It is slightly soluble in water, DMSO, and slightly soluble in methanol when heated.
synthesisThe precursor 3,5-(toluoyl)-2-deoxy-(N1,N3-15N)-uridine (1) was synthesized according to Schiesser et al.4 In a round bottom flask 1 (76 mg, 0.16 mmol, 1.0 eq.) was dissolved in dry MeOH (2.1 mL) and K2CO3 (49 mg, 0.35 mmol, 2.2 eq.) was added. The suspension was stirred at 40 °C for 6 h. The solvent was removed by rotary evaporation. The residue was then suspended in H2O (5 mL) and extracted with DCM (5 mL). The aqueous layer was then concentrated to dryness, redissolved in H2O and subjected to RP-HPLC (0% to 20% MeCN in water in 45 min, 5 mL/min). [15N2]-dU as a white solid (31 mg, 0.13 mmol, 84%).
synthesis of 2'-Deoxyuridine
Description2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
Chemical PropertiesWhite crystalline powder
Uses2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.
UsesAn uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease
DefinitionChEBI: 2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil.
Biological Activity2'-deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of dna synthesis and degradation mechanisms.
Tag:2'-Deoxyuridine(951-78-0) Related Product Information
6-Methyluracil Uridine Cytidine 1-beta-D-Arabinofuranosyluracil Uracil Deoxycholic acid Disodium 5'-dGMP Thymidine-5'-monophosphate disodium salt 2'-Deoxyuridine 5'-monophosphate disodium salt DNA polymeraseⅠfrom E.coli BROMO-2'-DEOXYURIDINE,5-,BROMO-2'-DEOXYURIDINE,5- PROTOVERATRINE B Doxifluridine DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* BrdU (Bromodeoxyuridine) beta-5-fluoro-2’-deoxyuridin 5-Methyluridine Trifluridine