5-Ethynyl-2'-deoxycytidine

Product Name: 5-Ethynyl-2'-deoxycytidine
CAS No.: 69075-47-4
Chemical Name: 5-Ethynyl-2'-deoxycytidine
Synonyms: 5-Ethynyl-2'-dC;-Ethynyl-2’2'-Deoxy-5-ethynylcytidine;5-Ethynyl-2'-deoxycytidine;5'-Ethynyl-2'-deoxycytidine;Cytidine, 2'-deoxy-5-ethynyl-;5-Ethynyl-2'-deoxycytidine>5-Ethynyl-2′-deoxycytidine, (EdC);5-Ethynyl-2'-deoxycytidine 69075-47-4;5-Ethynyl-2'-deoxycytidine, (EdC) AldrichCPR
CBNumber: CB62682226
Molecular Formula: C11H13N3O4
Formula Weight: 251.24
MOL File: 69075-47-4.mol

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5-Ethynyl-2'-deoxycytidine Property

Melting point:: 191 °C (decomp)(Solv: dichloromethane (75-09-2); methanol (67-56-1))
Boiling point:: 475.7±55.0 °C(Predicted)
Density: 1.54±0.1 g/cm3(Predicted)
storage temp.: Store at 2-8°C, protect from light, stored under nitrogen
solubility: DMF: 5 mg/ml; DMSO: 20 mg/ml; PBS (pH 7.2): 10 mg/ml
pka: 14.03±0.60(Predicted)
form: powder to crystal
color: White to Light yellow to Light orange
λmax: 292nm(H2O)(lit.)
InChI: 1S/C11H13N3O4/c1-2-6-4-14(11(17)13-10(6)12)9-3-7(16)8(5-15)18-9/h1,4,7-9,15-16H,3,5H2,(H2,12,13,17)/t7-,8+,9+/m0/s1
InChIKey: HMJSYXIPNSASJY-DJLDLDEBSA-N
SMILES: NC1=NC(=O)N(C=C1C#C)[C@H]2C[C@H](O)[C@@H](CO)O2

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Safety

WGK Germany: 3
HS Code: 2934.99.4400
Storage Class: 11 - Combustible Solids

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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: T511307
Product name: 5-Ethynyl-2′-deoxycytidine, (EdC)
Purity: AldrichCPR
Packaging: 5mg
Price: $198
Updated: 2026/03/19

TCI Chemical

Product number: E1093
Product name: 5-Ethynyl-2'-deoxycytidine
Purity: >98.0%(N)
Packaging: 50mg
Price: $203
Updated: 2021/12/16

TCI Chemical

Product number: E1093
Product name: 5-Ethynyl-2'-deoxycytidine
Purity: >98.0%(N)
Packaging: 200mg
Price: $605
Updated: 2026/03/19

Cayman Chemical

Product number: 11581
Product name: 5'-Ethynyl-2'-deoxycytidine
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 11581
Product name: 5'-Ethynyl-2'-deoxycytidine
Purity: ≥98%
Packaging: 5mg
Price: $116
Updated: 2024/03/01

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5-Ethynyl-2'-deoxycytidine Chemical Properties,Usage,Production

Description

5''-Ethynyl-2''-deoxycytidine (EdC) is a nucleoside analog that inhibits replication of the herpes simplex virus-1 (HSV-1) KOS strain (ID₅₀ = 0.2 μg/mL). It also reduces virus-induced cytopathogenicity of HSV-1, HSV-2, and vaccinia virus strains in PRK cells (MICs = 0.2-0.4, 1-2, and 5 μg/ml, respectively). EdC is an inhibitor of thymidylate synthetase, selectively reducing DNA incorporation of [1'',2''-³H]deoxyuridine over [CH₃-³H]deoxythymidine in PRK cells (ID₅₀s = 3 and 120 μg/ml, respectively). It inhibits thymidine synthetase in and reduces proliferation of L1210 cells, an effect which is reversed by addition of deoxythymidine (ID₅₀s = 4.4 and 1,000 μg/ml, respectively). EdC has been used to monitor DNA synthesis and cellular replication via click chemistry conjugation of the ethynyl group to an azido group of various fluorochromes.

Uses

5-Ethynyl-2’-deoxycytidine is an lower toxicity analog of 2’-deoxycytidine, a metabolic labeling probe for DNA synthesis. 5-Ethynyl-2’-deoxycytidine is most commonly used when thymidine analogs is undesirable.

Uses

A relatively nontoxic 2′-deoxycytidine analog for metabolic labeling of newly synthesized DNA in vivo. Especially suitable if the use of thymidine analogs is undesirable.

reaction suitability

reaction type: click chemistry

Synthesis

1) 5-Iodo-2’3’5’-oxo-triacetyluridine (15 g, 30.23 mmol, 1eq) was dissolved in 200 ml of CH2Cl2:(C2H5)3N1:1 mixed solution, to which was added under the protection of N2 (PPh3)2PdCl2 (1.59 g, 2.27 mmol. 0.075eq), CuI (0.86g, 4.52mmol, 0.15eq), trimethylsilylacetylene (6.24g, 8.8ml, 63.53mmol, 2.1eq), stirred at room temperature under the protection of N2 for 20h, evaporated to remove the solvent, and the residue was dissolved with 300ml of CH2Cl2, and the organic layer was dissolved with 2×200ml of 10 The organic layer was washed with 2×200ml of 10% EDTA disodium aqueous solution, 200ml of saturated saline solution, the aqueous layer was re-extracted with 200ml of CH2Cl2, the organic layer was combined, the solvent was spun dry, and separated on a column, and the ratio of the eluent, PE:EA, was 31~11, yielding a light-yellow foam, 5-[(trimethylsilyl)acetylidene]-2’3’5’-oxytriacetyl uridine 11.4g, yielding a light yellow foam, 5-[(trimethylsilyl)ethynyl]-2’3’5’-oxytriacetyl uridine 11.4g. Glycoside 11.4 g, yield 81%.

References

[1] R. WALKER. The synthesis and properties of some antiviral nucleosides[J]. Nucleic Acids Research, 1978, 1 1. DOI: 10.1093/nar/1.suppl_1.s103
[2] E DE CLERCQ. Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 2’-deoxycytidines.[J]. Molecular Pharmacology, 1982, 21 1: 217-223.
[3] FRANK SEELA. 5-Ethynyl-2’-deoxycytidine: a DNA building block with a “clickable” side chain.[J]. Acta crystallographica. Section C, Crystal structure communications, 2012, 68 Pt 10: o395-8. DOI: 10.1107/s0108270112038267

5-Ethynyl-2'-deoxycytidine Preparation Products And Raw materials

Raw materials

Preparation Products

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5-Ethynyl-2'-deoxycytidine Suppliers

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View Lastest Price from 5-Ethynyl-2'-deoxycytidine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: 5-Ethynyl-2'-deoxycytidine 69075-47-4
Price: US $0.00-0.00/g
Min. Order: 10g
Purity: 98%min
Supply Ability: 1000g
Release date: 2021-09-03

Henan Aochuang Chemical Co.,Ltd.

Product: 5-Ethynyl-2'-deoxycytidine 69075-47-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-26

Career Henan Chemical Co

Product: 5-Ethynyl-2'-deoxycytidine 69075-47-4
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98% HPLC
Supply Ability: 10 tons
Release date: 2020-03-04

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