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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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
J Vanden Bussche et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 28(2), 166-172 (2011-01-26)
Thiouracil belongs to the xenobiotic thyreostats, which are growth-promoting agents illegally used in animal production. Recently it has been reported that thiouracil is suspected to have a natural origin. The European Union of Reference Laboratory guidance paper of 2007 acknowledged
Leslie Gay et al.
Genes & development, 27(1), 98-115 (2013-01-12)
Transcriptional profiling is a powerful approach for understanding development and disease. Current cell type-specific RNA purification methods have limitations, including cell dissociation trauma or inability to identify all RNA species. Here, we describe "mouse thiouracil (TU) tagging," a genetic and
Sarah E Munchel et al.
Molecular biology of the cell, 22(15), 2787-2795 (2011-06-18)
RNA levels are determined by the rates of both transcription and decay, and a mechanistic understanding of the complex networks regulating gene expression requires methods that allow dynamic measurements of transcription and decay in living cells with minimal perturbation. Here
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