Description Physical properties synthesis
ChemicalBook > CAS DataBase List > 2'-Deoxyuridine

2'-Deoxyuridine

Description Physical properties synthesis
Product Name
2'-Deoxyuridine
CAS No.
951-78-0
Chemical Name
2'-Deoxyuridine
Synonyms
DU;deoxyuridine;1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione;durd;2'-dU;NSC 23615;Uracildeoxyr;Deoxy-uridin;DEOXYURIDINE-2';2'-deoxy-uridin
CBNumber
CB3472057
Molecular Formula
C9H12N2O5
Formula Weight
228.2
MOL File
951-78-0.mol
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2'-Deoxyuridine Property

Melting point:
167-169 °C(lit.)
alpha 
D22 +50° (c = 1.1 in N NaOH)
Boiling point:
370.01°C (rough estimate)
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)
form 
Powder
pka
pKa 9.3(H2O t = 25) (Uncertain)
color 
White to off-white
biological source
synthetic (organic)
Water Solubility 
300 g/L (20 ºC)
Sensitive 
Air Sensitive
Merck 
14,2910
BRN 
24433
InChIKey
MXHRCPNRJAMMIM-ATRFCDNQSA-N
CAS DataBase Reference
951-78-0(CAS DataBase Reference)
EPA Substance Registry System
Uridine, 2'-deoxy- (951-78-0)
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Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38
Safety Statements 
22-24/25-37/39-36/37/39-26
WGK Germany 
3
RTECS 
YU7490000
F 
10-23
Hazard Note 
Air Sensitive
TSCA 
Yes
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D5412
Product name
2′-Deoxyuridine
Purity
≥98.5%
Packaging
1g
Price
$155
Updated
2024/03/01
Sigma-Aldrich
Product number
D5412
Product name
2′-Deoxyuridine
Purity
≥98.5%
Packaging
5g
Price
$521
Updated
2024/03/01
TCI Chemical
Product number
D0060
Product name
2'-Deoxyuridine
Purity
>99.0%(HPLC)
Packaging
1g
Price
$84
Updated
2024/03/01
TCI Chemical
Product number
D0060
Product name
2'-Deoxyuridine
Purity
>99.0%(HPLC)
Packaging
5g
Price
$212
Updated
2024/03/01
Alfa Aesar
Product number
A16026
Product name
2'-Deoxyuridine, 99%
Packaging
1g
Price
$22.65
Updated
2024/03/01
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2'-Deoxyuridine Chemical Properties,Usage,Production

Description

2'-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 properties

2'-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.

synthesis

The 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%).

Description

2'-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 Properties

White crystalline powder

Uses

2'-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.

Uses

An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease

Definition

ChEBI: 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 Activity

2'-deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of dna synthesis and degradation mechanisms.

2'-Deoxyuridine Preparation Products And Raw materials

Raw materials

Preparation Products

5-CHLORO-2'-DEOXYURIDINE
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View Lastest Price from 2'-Deoxyuridine manufacturers

HangZhou RunYan Pharma Technology Co.,LTD.
Product
2'-Desoxyuridine 951-78-0
Price
US $0.00-0.00/g
Min. Order
10g
Purity
99% HPLC
Supply Ability
10000
Release date
2024-09-20
WUHAN FORTUNA CHEMICAL CO., LTD
Product
2'-Deoxyuridine 951-78-0
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
99%min
Supply Ability
100KG
Release date
2021-06-01
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
2'-Deoxyuridine 951-78-0
Price
US $999.00-800.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-21

951-78-0, 2'-DeoxyuridineRelated Search:

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

  • 1-(2'-DEOXY-BETA-D-RIBOFURANOSYL)URACIL
  • 1-(2-DEOXY-BETA-D-RIBOFURANOSYL)URACIL
  • (+)-2'-DEOXYURIDINE
  • DEOXYURIDINE-2'
  • DU
  • (+)-2'-DEOXYURIDINE, 99+%
  • Uracildeoxyr
  • 1-(2-Deoxy-b-D-erythro-pentofuranosyl)uracil
  • NSC 23615
  • 1-(2-deoxy-á-d-ribofuranosyl)uracil
  • 2'-Deoxy-D-uridine
  • 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  • 2'-deoxy-uridin
  • 1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
  • 1-(2-Deoxy--D-erythro-pentofuranosyl)uracil
  • 1-((2R,4R,5R)-4-HYDROXY-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2-YL)PYRIMIDINE-2,4(1H,3H)-DIONE
  • 2-DEOXYURIDINE extrapure
  • 1-(2-Deoxy-β-D-ribofuranosyl)uracil, Uracil deoxyriboside
  • 1-(2-Deoxy-β-D-ribofuranosyl)uracil, 2μ-Deoxyuridine, Uracil deoxyriboside
  • Uridine, 2'-deoxy
  • 2'-dU
  • 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxyMethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyriMidine-2,4-dione
  • 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
  • 2'-Deowyuridine
  • -deoxyuridine N-Hydroxysuccinimide Ester
  • Cytarabine Impurity 19（2'-Deoxyuridine）
  • (E)-5-(2-Carboxyvinyl)-2&rsquo
  • (E)-5-(2-Carbomethoxyvinyl)-2&rsquo
  • S4-(2-Cyanoethyl)-4-thio-2&rsquo
  • -deoxyuridine-d1
  • 5-Ethynyl-2&rsquo
  • 5-Hydroxymethyl-2&rsquo
  • 2'-Deoxyuridine(2'-dU)
  • 5-(2-Furanyl)-2&rsquo
  • 5-[N(6-(Trifluoroacetamido)hexyl)-3-(E)-acrylamido]-2&rsquo
  • 2'-DEOXYURIDINE 99-100%
  • 1-(2-Deoxy-β-D-ribofuranosyl)uracil
  • Deoxy-uridin
  • 1-(2-Deoxy-beta-D-ribofuranosyl)uracil, Uracil deoxyriboside
  • URACIL DEOXYRIBOSIDE
  • 2’-desoxyuridine
  • deoxyriboseuracil
  • deoxyuridine
  • durd
  • uracildesoxyuridine
  • 2'-Deoxyuridine &gt
  • 2-Deoxyuridine, 1-(beta-D-ribofuranosyl)-4-pyrimidinone
  • 2'-Deoxyuridine USP/EP/BP
  • (+)-2`-Deoxyuridine
  • 2‘-dU/ 2'-Deoxyuridine
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4(1H,3H)-dione (2’-deoxyuridine)
  • 2'-Deoxyuridine, ≥ 98.0%
  • 2'-Deoxyuridine
  • 2''-Deoxyuridine
  • （2‘-dU） 2'-DeoxyUridine
  • 2'-Deoxyuridine-d
  • 2'-Desoxyuridine
  • Brovudine impurity 4