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T7750

Sigma-Aldrich

2-Thiouracil

≥99%

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:
141-90-2
Molecular Weight:
128.15
Beilstein:
112227
EC Number:
205-508-8
MDL number:
MFCD00006039
UNSPSC Code:
41106305
PubChem Substance ID:
24900470
NACRES:
NA.51

biological source

synthetic

Quality Level

200

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

SMILES string

O=C1NC(=S)NC=C1

InChI

1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

InChI key

ZEMGGZBWXRYJHK-UHFFFAOYSA-N

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General description

2-Thiouracil is a thio-derivative of uracil, a pyrimidine nucleobase.This antithyroid drug has less solubility in H2O & organic solvents.

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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

Hazard Classifications

Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
K P Prasanthkumar et al.
The journal of physical chemistry. A, 116(44), 10712-10720 (2012-10-16)
The reaction of hydroxyl radical ((•)OH) with the nucleic acid base analogue 2-thiouracil (1) has been studied by pulse radiolysis experiments and DFT. The generic intermediate radicals feasible for the (•)OH reactions with 1, namely, one electron oxidation product (1(•+))
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