Skip to Content
Merck
All Photos(5)

Key Documents

View All Documentation

T7750

Sigma-Aldrich

2-Thiouracil

≥99%

Synonym(s):

(2-thioxo -2, 3-dihydropyrimidin-4(1H)-one), 2TU, 4-Hydroxy-2-mercaptopyrimidine

Sign Into View Organizational & Contract Pricing
All Photos(5)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Methimazole VETRANAL®, analytical standard

Supelco

46429

Methimazole

Carbimazole ≥98% (HPLC)

Sigma-Aldrich

SML0931

Carbimazole

2-Mercaptobenzimidazole 98%

Sigma-Aldrich

M3205

2-Mercaptobenzimidazole

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
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(•+))
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service