CAS 591-28-6

4-Thiouracil

Description:

4-Thiouracil is a sulfur-containing derivative of uracil, classified as a pyrimidine base. Its chemical formula is C4H4N2O2S, and it features a thiol group (-SH) at the 4-position of the uracil ring, which distinguishes it from uracil itself. This compound is typically a white to off-white crystalline solid and is soluble in water and alcohol. 4-Thiouracil is known for its role as an antithyroid agent, as it inhibits the synthesis of thyroid hormones by blocking the incorporation of iodine into tyrosine residues in thyroglobulin. Additionally, it has applications in biochemistry and molecular biology, particularly in studies involving RNA and nucleic acid metabolism. The compound's mechanism of action and its ability to interfere with nucleic acid synthesis make it a valuable tool in research and therapeutic contexts. However, like many chemical substances, it should be handled with care due to potential toxicity and side effects associated with its use.

Formula: C₄H₄N₂OS

InChI: InChI=1S/C4H4N2OS/c7-4-5-2-1-3(8)6-4/h1-2H,(H2,5,6,7,8)

InChI key: InChIKey=OVONXEQGWXGFJD-UHFFFAOYSA-N

SMILES: S=C1NC(=O)NC=C1

Synonyms:

• Uracil, 4-thio-
• 4-Thiopyrimidin-2-one
• 2(1H)-Pyrimidinone, 3,4-dihydro-4-thioxo-
• 3,4-Dihydro-4-thioxo-2(1H)-pyrimidinone
• 4-Thiouracil

4-Thiouracil

CAS: 591-28-6

Formula: C₄H₄N₂OS

Purity: >97.0%(T)(HPLC)

Color and Shape: Light yellow to Yellow to Green powder to crystal

Molecular weight: 128.15

Ref: 3B-T2757

4-Thiouracil, 97%

CAS: 591-28-6

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₄H₄N₂OS

Purity: 97%

Molecular weight: 128.15

Ref: 02-H61919

4-Thiouracil

CAS: 591-28-6

Formula: C₄H₄N₂OS

Purity: 97%

Color and Shape: Solid

Molecular weight: 128.1524

Ref: IN-DA00345K

4-Thiouracil

CAS: 591-28-6

Formula: C₄H₄N₂OS

Purity: ≥ 97.0%

Color and Shape: Faint yellow to yellow powder

Molecular weight: 128.16

Ref: 7W-GN5189

4-Thioxo-3,4-dihydropyrimidin-2(1H)-one

CAS: 591-28-6

4-Thioxo-3,4-dihydropyrimidin-2(1H)-one

Purity: 97%

Molecular weight: 128.15g/mol

Ref: 54-OR90861

4-Thiouracil

CAS: 591-28-6

Applications 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.
References Miller, M., et al.: Nat. Methods, 6, 439 (2009); Seth, P., et al.: J. Med. Chem., 53, 8309 (2010); Cui, H., et al.: Eur. J. Med. Chem., 45, 5140 (2010);

Formula: C₄H₄N₂OS

Color and Shape: Neat

Molecular weight: 128.152

Ref: TR-T375405

4-Thiouracil

CAS: 591-28-6

Formula: C₄H₄N₂OS

Purity: 97%

Color and Shape: Slightly pale yellow – Yellow green powder

Molecular weight: 128.15

Ref: 10-F013726

4-Thiouracil

CAS: 591-28-6

4-Thiouracil is a uridine analog and has been shown to inhibit transcriptional regulation by hydrogen bonding with the dna template. 4-Thiouracil is a prodrug that is converted to its active form, thiouracil, which inhibits DNA synthesis and cell proliferation by inhibiting the enzyme topoisomerase II. This results in the formation of abnormal DNA molecules that are not replicated properly. Thiouracil also has photochemical properties due to its ability to absorb light at wavelengths below 400 nm. The photochemical properties of 4-thiouracil have been studied extensively as models for human tissue culture and the study of cancer cells.

Formula: C₄H₄N₂OS

Purity: Min. 97 Area-%

Color and Shape: Slightly Yellow Powder

Molecular weight: 128.15 g/mol

Ref: 3D-FT02605

4-Thiouracil

CAS: 591-28-6

4-Thiouracil is a photoactivatable probe designated for site-specific applications in detecting RNA structures and nucleic acid-nucleic acid contacts. Upon illumination with ultraviolet light exceeding 300 nm and in the presence of oxygen, it serves as an energy donor, facilitating the generation of singlet oxygen through triplet-triplet energy transfer. This process enables the highly reactive oxygen species to interact with 4-thiouracil, leading to the formation of uracil and uracil-6-sulfonate; the latter exhibits fluorescence around a wavelength of approximately 390 nm. Additionally, 4-Thiouracil functions as a substrate for T. gondii uracil phosphoribosyltransferase, allowing the synthesis of 4-thiouridine monophosphate for subsequent integration into RNA.

Formula: C₄H₄N₂OS

Color and Shape: Solid

Molecular weight: 128.15

Ref: TM-T84403