Thymidine Chemical Properties

Melting point:

186-188 °C(lit.)

alpha 

18.6 º (c=3, H2O)

Boiling point:

385.05°C (rough estimate)

Density 

1.3129 (rough estimate)

refractive index 

33 ° (C=1, 1mol/L NaOH)

storage temp. 

2-8°C

solubility 

Acetone, DMSO (Slightly), Ethanol, Ethyl Acetate, Methanol (Slightly, Heated), P

pka

pK1:9.79;pK2:12.85 (25°C)

form 

Crystalline Powder

color 

White to almost white

PH

9.8

optical activity

[α]20/D +19±1°, c = 1% in H2O

Water Solubility 

SOLUBLE

λmax

267 (pH 7)；267 (pH 13)

Merck 

14,9397

BRN 

89285

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

IQFYYKKMVGJFEH-XLPZGREQSA-N

LogP

-0.930

CAS DataBase Reference

50-89-5(CAS DataBase Reference)

NIST Chemistry Reference

Thymidine(50-89-5)

EPA Substance Registry System

Thymidine (50-89-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-40-36/37/38-68

Safety Statements 

22-24/25-37/39-26-36/37/39

WGK Germany 

3

RTECS 

XP2071000

F 

10

TSCA 

Yes

HS Code 

29335990

MSDS

• Language:English Provider:Thymine deoxyriboside
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Thymidine Usage And Synthesis

Description

Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. In cell biology it is used to synchronize the cells in G₁/early S phase.

Chemical Properties

White needle crystal, soluble in methanol, ethanol, DMSO and other organic solvents.

Physical properties

Thymidine can exist in vitro conditions as a solid (as white crystals or as white crystalline powder). Under standard temperature and pressure, the stability of this compound is very high. As a part of DNA structure, thymidine occurs in living organisms (also in DNA viruses). Therefore, it is a non-toxic compound. In RNA, there is uridine instead of thymidine. Uridine is formed from the combination of uracil with ribose sugar. The key difference between thymine and thymidine is that thymine is a nucleobase, whereas thymidine is a nucleoside.

Uses

Constituent of deoxyribonucleic acid. The nucleoside (deoxyriboside) of thymine. Occurs in DNA. It is a nucleoside consisting of one thymine molecule linked to ad-doxyribose sugar molecule.

Uses

Thymidine is used in the syntheses of active pharmaceutical ingredient such as zidovudine. It also pairs with deoxyadenosine in double-stranded deoxyribonucleic acid. It is used to synchronize the cells in G1/early S phase in cell biology.

Definition

The NUCLEOSIDE formed when thymine is linked to D-ribose by a β-glycosidic bond.

Definition

ChEBI: Thymidine is a pyrimidine 2'-deoxyribonucleoside having thymine as the nucleobase. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a thymine. It is an enantiomer of a telbivudine.

General Description

Thymidine is also referred to as pyrimidine deoxynucleoside. Deoxythymidine is a nucleoside present in DNA. In a DNA double stranded structure, thymidine pairs with deoxyadeninosine.

Biochem/physiol Actions

Thymidine is useful in cell synchronization during S-phase. In the salvage pathway of pyrimidines, pyrimidine phosphorylase reversibly converts thymine to thymidine.

Mechanism of action

High concentrations of thymidine interrupt the deoxynucleotide metabolism pathway through competitive inhibition, thus blocking DNA replication. A single treatment with thymidine arrests cells throughout S phase, so a double treatment acts to induce a more uniform block in early S phase.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise -thymidine from ethyl acetate, MeOH/Et2O (m 188o) or H2O (as 2H2O m 189o). It is soluble in water and hot organic solvents. The picrate has m 230o (from EtOH).

Thymidine(50-89-5)Related Product Information

• Starch soluble
• Thymine
• 5-HYDROXYMETHYL-2'-DEOXYURIDINE
• T-SUCCINATE5'-O-DMTR-THYMIDINE-SUCCINATE
• 5’-o-[bis(4-methoxyphenyl)phenylmethyl]-thymidi
• THYMIDINE 5'-TRIPHOSPHATE SODIUM SALT,THYMIDINE-5'-TRIPHOSPHATE TETRASODIUM SALT,THYMIDINE-5'-TRIPHOSPHATE TRISODIUM SALT
• 3’-azido-3’-deoxy-thymidi
• Trifluridine
• DMT-dT Phosphoramidite
• 5-Methyluridine
• 5’-o-(triphenylmethyl)-thymidi
• Thymidine-5'-monophosphate disodium salt
• 3’-deoxy-thymidi
• Deoxythymidine triphosphate
• 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
• 3’-deoxy-3’-fluoro-thymidi
• 2’,3’-didehydro-3’-deoxy-thymidi
• THYMIDINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT