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T7750

Sigma-Aldrich

2-Thiouracil

≥99%

Synonym(e):

4-Hydroxy-2-mercapto-pyrimidin

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About This Item

Empirische Formel (Hill-System):
C4H4N2OS
CAS-Nummer:
141-90-2
Molekulargewicht:
128.15
Beilstein:
112227
EG-Nummer:
205-508-8
MDL-Nummer:
MFCD00006039
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24900470
NACRES:
NA.51
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Biologische Quelle

synthetic

Assay

≥99%

Form

powder

mp (Schmelzpunkt)

>300 °C (lit.)

Löslichkeit

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)

InChIKey

ZEMGGZBWXRYJHK-UHFFFAOYSA-N

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Allgemeine Beschreibung

2-Thiouracil is a thio-derivative of uracil, a pyrimidine nucleobase.[1]This antithyroid drug has less solubility in H2O & organic solvents.[2]

Anwendung

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)[1]
  • to study its electro-oxidation and determination at titanium dioxide (TiO2) nanoparticles-modified gold electrode[3]
  • to study the effect of methylation on the deactivation mechanism or the triplet-state dynamics of 2-thiouracil using time-resolved photoelectron spectroscopy[4]

Biochem./physiol. Wirkung

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.[5] It also forms complexes with transition metals such as gold (Au), chromium (Cr), zinc (Zn), and silver (Ag).[1]2-thiouracil can be incorporated into the tissue culture medium to inhibit virus replication or movement from infected to healthy tissues during chemotherapy.[6]

Piktogramme

Health hazard
GHS08

Signalwort

Warning

H-Sätze

H351

Gefahreneinstufungen

Carc. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Analysenzertifikate (COA)

Lot/Batch Number
0000333437
0000333437
SLCG4969
SLCF1454
SLCD2322

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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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