T7750
2-Thiouracil
≥99%, synthetic, powder
Synonym(s):
(2-thioxo -2, 3-dihydropyrimidin-4(1H)-one), 2TU, 4-Hydroxy-2-mercaptopyrimidine
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About This Item
Empirical Formula (Hill Notation):
C4H4N2OS
CAS Number:
Molecular Weight:
128.15
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
205-508-8
MDL number:
Beilstein/REAXYS Number:
112227
Assay:
≥99%
Biological source:
synthetic
Form:
powder
Solubility:
1 M NaOH: 5 mg/mL, clear to very slightly hazy
1 M NaOH: 50 mg/mL, colorless to faintly yellow
1 M NaOH: 50 mg/mL, colorless to faintly yellow
Product Name
2-Thiouracil, ≥99%
InChI
1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI key
ZEMGGZBWXRYJHK-UHFFFAOYSA-N
SMILES string
O=C1NC(=S)NC=C1
biological source
synthetic
assay
≥99%
form
powder
mp
>300 °C (lit.)
solubility
1 M NaOH: 5 mg/mL, clear to very slightly hazy
1 M NaOH: 50 mg/mL, colorless to faintly yellow
Quality Level
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Application
2-Thiouracil may be used:
- in the synthesis and characterization of silver colloid and film substrates and their applications in surface-enhanced Raman scattering (SERS)
- to study its electro-oxidation and determination at titanium dioxide (TiO2) nanoparticles-modified gold electrode
- to study the effect of methylation on the deactivation mechanism or the triplet-state dynamics of 2-thiouracil using time-resolved photoelectron spectroscopy
Biochem/physiol Actions
2-Thiouracil acts as an anticancer, antithyroid, and antiviral agent. 2-Thiouracil is a selective melanoma-seeker and competitive inhibitor of neuronal nitric oxide synthase. It also forms complexes with transition metals such as gold (Au), chromium (Cr), zinc (Zn), and silver (Ag).2-thiouracil can be incorporated into the tissue culture medium to inhibit virus replication or movement from infected to healthy tissues during chemotherapy.
General description
2-Thiouracil is a thio-derivative of uracil, a pyrimidine nucleobase.This antithyroid drug has less solubility in H2O & organic solvents.
signalword
Warning
hcodes
Hazard Classifications
Carc. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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Silver colloid and film substrates in surface-enhanced Raman scattering for 2-thiouracil detection
Al-Shalalfeh MM, et al.
Royal Society of Chemistry Advances, 6, 75282-75292 (2016)
A Palumbo et al.
FEBS letters, 485(2-3), 109-112 (2000-11-30)
2-thiouracil (TU), an established antithyroid drug and melanoma-seeker, was found to selectively inhibit neuronal nitric oxide synthase (nNOS) in a competitive manner (K(i)=20 microM), being inactive on the other NOS isoforms. The drug apparently interfered with the substrate- and tetrahydrobiopterin
Julie A L Kiebooms et al.
Journal of agricultural and food chemistry, 60(32), 7769-7776 (2012-07-28)
In recent years, the frequent detection of the banned substance thiouracil (TU) in livestock urine has been related to its endogenous formation following consumption of glucosinolate-rich Brassicaceae crops. Besides, TU residues have been recovered in these crops upon plant-derived myrosinase
Raj Kumar Bera et al.
Chemical communications (Cambridge, England), 47(41), 11498-11500 (2011-09-22)
A nonenzymatic method for the selective detection and quantification of serum uric acid (UA) using 2-thiouracil (2-TU) tailored Au nanoparticles is developed. The H-bonding interaction of UA with functionalized Au nanoparticles brings instantaneous visible color change and paves the way
Karina Kraszewska et al.
Bioorganic & medicinal chemistry, 19(7), 2443-2449 (2011-03-15)
4-Pyrimidinone ribofuranoside (H(2)o(4)U) and 4-pyrimidinone 2'-deoxyribofuranoside (dH(2)o(4)U) were synthesized by the oxidative desulfurization of parent 2-thiouracil nucleosides with m-chloroperbenzoic acid. The crystal structures of H(2)o(4)U and dH(2)o(4)U and their conformations in solution were determined and compared with corresponding 2-thiouracil and
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