Thymidine

Base Information

• Chemical Name: Thymidine
• CAS No.: 50-89-5
• Deprecated CAS: 35902-13-7
• Molecular Formula: C10H14N2O5
• Molecular Weight: 242.232
• Hs Code.: PRICE
• European Community (EC) Number: 200-070-4
• UNII: VC2W18DGKR
• DSSTox Substance ID: DTXSID5023661
• Nikkaji Number: J4.548I
• Wikipedia: Thymidine
• Wikidata: Q422464
• NCI Thesaurus Code: C880
• Pharos Ligand ID: ZPLW32L1R1P3
• Metabolomics Workbench ID: 37175
• ChEMBL ID: CHEMBL52609
• Mol file: 50-89-5.mol

Synonyms:2' Deoxythymidine;2'-Deoxythymidine;Deoxythymidine;Thymidine

Chemical Property of Thymidine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 186-188 °C(lit.)
• Refractive Index: 33 ° (C=1, 1mol/L NaOH)
• Boiling Point: 385.05°C (rough estimate)
• PKA: pK1:9.79;pK2:12.85 (25°C)
• PSA: 104.55000
• Density: 1.452 g/cm³
• LogP: -1.51430
• Storage Temp.: 0-6°C
• Solubility.: Acetone, DMSO (Slightly), Ethanol, Ethyl Acetate, Methanol (Slightly, Heated), P
• Water Solubility.: SOLUBLE
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09027155
• Heavy Atom Count: 17
• Complexity: 381

Purity/Quality:

98%, ^*data from raw suppliers

Thymidine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-40-36/37/38-68
• Safety Statements: 22-24/25-37/39-26-36/37/39

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
• Recent ClinicalTrials: Treatment of TK2 Deficiency With Thymidine and Deoxycytidine
• Recent EU Clinical Trials: A phase III, open-label, randomised multicentre study to evaluate the immunogenicity and safety of a booster dose of GlaxoSmithKline Biologicals’ dTpa-IPV vaccine (Boostrix Polio) compared with Sanofi Pasteur MSD’s dTpa-IPV vaccine (Repevax), when co-administered with GSK Biologicals’ MMR vaccine (Priorix) in 3 and 4-year-old healthy children.
• Description: Thymidine is a pyrimidine nucleoside composed of a pyrimidine base (thymine) linked to a deoxyribose sugar molecule. Thymidine's structure consists of a thymine base attached to the 2'-deoxyribose sugar.
• Uses and Mechanism of Action: Neuroprotective Effects:; Thymidine has been shown to exert neuroprotective effects in Alzheimer's disease (AD) models by reducing microglial activation, improving oxidative stress damage, and modulating glycolytic metabolism.; ; Antiviral Drug Transformation:; Thymidine can undergo ozonation, a water treatment process, which leads to the formation of transformation products. Understanding these products is essential for water treatment and environmental protection.
• Production Methods: Thymidine can be synthesized chemically or obtained from natural sources. Chemical synthesis involves the combination of thymine and deoxyribose or modification of related compounds.
• References: [1] Ozonation products of zidovudine and thymidine in oxidative water treatment; DOI 10.1016/j.wroa.2021.100090; [2] Thymidine and 2′-deoxyuridine reduce microglial activation and improve oxidative stress damage by modulating glycolytic metabolism on the Aβ25-35-induced brain injury; DOI 10.1016/j.abb.2022.109377; [3] Unraveling Water Solvation Effects with Quantum Mechanics/Molecular Mechanics Semiclassical Vibrational Spectroscopy: The Case of Thymidine; DOI 10.1021/jacs.3c12700

Technology Process of Thymidine

There total 350 articles about Thymidine 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:

thymidine 3'(4-nitrophenylphosphate) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With sodium acetate buffer; PDMase; at 37 ℃; for 0.166667h; Rate constant;

DOI:10.1246/bcsj.56.549

Reference yield:

5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' → 2'-deoxycytidine (959326-89-7) + 2'-Deoxyguanosine (961-07-9) + 2'-deoxy-5-ethynyluridine (61135-33-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With tris hydrochloride; alkaline phosphatase; snake venom phosphodiesterase; at 37 ℃; pH=8.3; Enzymatic reaction;

DOI:10.1002/chem.201001572

Reference yield:

C23H39N4O7P → C19H25N3O12P(1-) + thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrazole / acetonitrile / 4 h / 20 °C / Inert atmosphere

2: water; iodine / tetrahydrofuran; acetonitrile / 20 °C

3: hydrazinium monoacetate / methanol; dichloromethane / 2.5 h

4: water; sodium chloride / 72 h / 37 °C / pH 7.5 / Sealed tube; HEPES buffer; Enzymatic reaction

With tetrazole; water; iodine; hydrazinium monoacetate; sodium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.3390/molecules16010552

upstream raw materials:

3',5'-di-O-toluoylthymidine

5-methyldeoxycytidine

5-bromo-2'-deoxyuridine

2'-deoxy-5-(hydroxymethyl)uridine

Downstream raw materials:

5'-O-(phenylcarbamoyl)thymidine

choline

Octadecanoic acid (S)-2-{hydroxy-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester

5'-O-<9-<3-(Trifluoromethyl)phenyl>xanthen-9-yl>thymidine

Refernces

• 1、 -. "SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG". Page/Page column 7; 13. . Retrieved 2021/05/29.
• 2、 Bizzarri, Bruno Mattia,Fanelli, Angelica,Kapralov, Michail,Krasavin, Eugene,Saladino, Raffaele. "Meteorite-catalyzed intermoleculartrans-glycosylation produces nucleosides under proton beam irradiation". . p. 19258 - 19264. Retrieved 2021/06/03.