A photoreactive nucleobase analog
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Isomer(s)
347472-Thiouracil
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4-Thiouracil

Item No. 16952

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4-dihydro-4-thioxo-2(1H)-pyrimidinone
CAS Number
591-28-6
Synonyms
  • 2-hydroxy-4-Mercaptopyrimidine
  • NSC 43288
  • 4-Thiopyrimidin-2-one
  • 4-TU
Molecular Formula
C4H4N2OS
Formula Weight
128.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:5): 0.5 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
246, 326 nm
SMILES
O=C(NC=C1)NC1=S
InChi Code
InChI=1S/C4H4N2OS/c7-4-5-2-1-3(8)6-4/h1-2H,(H2,5,6,7,8)
InChi Key
OVONXEQGWXGFJD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $60

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    1 g

    $97

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    5 g

    $423

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miller, M.R., Robinson, K.J., Cleary, M.D., et al. TU-tagging: Cell type-specific RNA isolation from intact complex tissues. Nat. Methods 6(6), 439-441 (2009).

    2. Zou, X., Dai, X., Liu, K., et al. Photophysical and photochemical properties of 4-thiouracil: Time-resolved IR spectroscopy and DFT studies. J. Phys. Chem. B. 118(22), 5864-5872 (2014).

    3. Zeiner, G.M., Cleary, M.D., Fouts, A.E., et al. RNA analysis by biosynthetic tagging using 4-thiouracil and uracil phosphoribosyltransferase. Methods Mol. Biol. 418, 135-146 (2008).