4-THIOURACIL Chemical Properties

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

pka

5.38±0.20(Predicted)

form 

Powder

color 

Yellow

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 Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-THIOURACIL Usage And Synthesis

Description

4-Thiouracil is a site-specific, photoactivatable probe used to detect RNA structures and nucleic acid-nucleic acid contacts. 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. 4-Thiouracil is used as a T. gondii uracil phosphoribosyltransferase substrate to produce 4-thiouridine monophosphate, which can ultimately be incorporated into RNA.

Chemical Properties

yellow powder

Uses

4-Thiouracil is suitable reagent employed in Schneider′s media for the embryos during RNA extraction. It may be employed as reagent for the Northwestern blotting technique.

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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