A chlorinated derivative of uracil
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5-Chlorouracil

Item No. 27790

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-chloro-2,4(1H,3H)-pyrimidinedione
CAS Number
1820-81-1
Molecular Formula
C4H3ClN2O2
Formula Weight
146.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 8 mg/mlDMSO: 0.8 mg/mlEthanol: 53 mg/mlPBS (pH 7.2): 60 mg/ml
λmax
210, 272 nm
SMILES
O=C1NC(NC=C1Cl)=O
InChi Code
InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChi Key
ZFTBZKVVGZNMJR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $41

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    10 g

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    25 g

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    50 g

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    Cayman Chemical
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    Product Description

    5-Chlorouracil is a chlorinated derivative of the pyrimidine nucleoside base uracil (Item No. 26088). In vivo, it is converted into chlorodeoxyuridine, which is mutagenic and genotoxic.1 Uracil is chlorinated at the 5 position in a cell-free myeloperoxidase, peroxide, and chloride system in which hypochlorous acid is formed.2 5-Chlorouracil has been found in human neutrophils stimulated with phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in vitro and in inflammatory human exudate isolated from sites of superficial infection. Levels of 5-chlorouracil are increased in exudate isolated from the site of inflammation in a rat model of carrageenan-induced inflammation and in patient-derived human atherosclerotic aortic tissue.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Morris, S.M. The genetic toxicology of 5-fluoropyrimidines and 5-chlorouracil. Mutat. Res. 297(1), 39-51 (1993).

    2. Henderson, J.P., Byun, J., Takeshita, J., et al. Phagocytes produce 5-chlorouracil and 5-bromouracil, two mutagenic products of myeloperoxidase, in human inflammatory tissue. The Journal of Biological Chemisty 278(26), 23522-23528 (2003).

    3. Jiang, Q., Blount, B.C., and Ames, B.N. 5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. A gas chromatography-mass spectrometry assay. The Journal of Biological Chemisty 278(35), 32834-32840 (2003).

    4. Takeshita, J., Byun, J., Nhan, T.Q., et al. Myeloperoxidase generates 5-chlorouracil in human atherosclerotic tissue: A potential pathway for somatic mutagenesis by macrophages. The Journal of Biological Chemisty 281(6), 3096-3104 (2006).