An oxidized form of thymine and a marker of DNA oxidative damage
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5-Formyluracil

Item No. 36523

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinecarboxaldehyde
CAS Number
1195-08-0
Synonyms
  • NSC 197200
  • NSC 241524
  • Uracil-5-carboxaldehyde
Molecular Formula
C5H4N2O3
Formula Weight
140.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly SolubleDMSO: 1 mg/ml
λmax
227, 288 nm
SMILES
O=CC1=CNC(NC1=O)=O
InChi Code
InChI=1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10)
InChi Key
OHAMXGZMZZWRCA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $63

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    500 mg

    $106

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    1 g

    $174

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    5 g

    $618

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    Product Description

    5-Formyluracil is an oxidized form of thymine and a marker of DNA oxidative damage.1 Incorporation of 5-formyluracil into DNA forms mispairings with thymine, cytosine, and guanine and induces mutations in E. coli.2 5-Formyluracil (1 mM) decreases the viability of V9-4 lung fibroblasts and increases their mutation frequency in a concentration-dependent manner.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Douki, T., Delatour, T., Paganon, F., et al. Measurement of oxidative damage at pyrimidine bases in γ-irradiated DNA. Chem. Res. Toxicol. 9(7), 1145-1151 (1996).

    2. Anensen, H., Provan, F., Lian, A.T., et al. Mutations induced by 5-formyl-2'-deoxyuridine in Escherichia coli include base substitutions that can arise from mispairs of 5-formyluracil with guanine, cytosine and thymine. Mutat. Res. 476(1-2), 99-107 (2001).

    3. Klungland, A., Paulsen, R., Rolseth, V., et al. 5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism. Toxicol. Lett. 119(1), 71-78 (2001).