| Identification | More | [Name]
4-THIOURACIL | [CAS]
591-28-6 | [Synonyms]
2-HYDROXY-4-MERCAPTOPYRIMIDINE
4-THIOURACIL
2(1H)-Pyrimidinone, 3,4-dihydro-4-thioxo-
KC 135
Uracil, 4-thio-
4-Thiouracil97%
4-Thiouracil 97%
2(1H)-Pyrimidinone, 3,4-dihydro-4-thioxo-(9CI)
2-HYDROXY-4-MERCAPTOPYRIMIDINE/4-THIOURACIL
4-Thiouracil ,98%
4-Thioxo-1H-pyrimidin-2-one | [Molecular Formula]
C4H4N2OS | [MDL Number]
MFCD00090842 | [Molecular Weight]
128.15 | [MOL File]
591-28-6.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [Melting point ]
295 °C (dec.) (lit.) | [density ]
1.368 (estimate) | [refractive index ]
1.7000 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
1 M NaOH: soluble50mg/mL | [form ]
Powder | [pka]
5.38±0.20(Predicted) | [color ]
Yellow | [Detection Methods]
HPLC | [InChI]
InChI=1S/C4H4N2OS/c7-4-5-2-1-3(8)6-4/h1-2H,(H2,5,6,7,8) | [InChIKey]
OVONXEQGWXGFJD-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=CC(=S)N1 | [CAS DataBase Reference]
591-28-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
4-Thiouracil is a site-specific, photoactivatable probe used to detect RNA structures and nucleic acid-nucleic acid contacts.1 It absorbs ultraviolet light >300 nm and, in the presence of oxygen, acts as an energy donor to produce singlet oxygen by triplet-triplet energy transfer. The highly reactive oxygen species then reacts readily with 4-thiouracil, leading to the production of uracil and uracil-6-sulfonate, which is fluorescent at a wavelength of ~390 nm.2 4-Thiouracil is used as a T. gondii uracil phosphoribosyltransferase substrate to produce 4-thiouridine monophosphate, which can ultimately be incorporated into RNA.3 | [Chemical Properties]
yellow powder | [Uses]
4-Thiouracil is a derivative of Uracil (U801000), which is a nitrogenous base in RNA nucleic acid. 4-Thiouracil is used for tagging in cell type-specific RNA isolation from intact complex tissues. | [Synthesis Reference(s)]
Synthesis, p. 256, 1987 DOI: 10.1055/s-1987-27906 | [References]
[1] MICHAEL R MILLER. TU-tagging: cell type–specific RNA isolation from intact complex tissues[J]. Nature Methods, 2009, 6 6: 439-441. DOI: 10.1038/nmeth.1329
[2] XIAORAN ZOU. Photophysical and Photochemical Properties of 4-Thiouracil: Time-Resolved IR Spectroscopy and DFT Studies[J]. The Journal of Physical Chemistry B, 2014, 118 22: 5864-5872. DOI: 10.1021/jp501658a
[3] GUSTI M ZEINER. RNA analysis by biosynthetic tagging using 4-thiouracil and uracil phosphoribosyltransferase.[J]. Methods in molecular biology, 2008, 419: 135-146. DOI: 10.1007/978-1-59745-033-1_9 |
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