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Hydroxymethyl Uracil

Catalog No.
C5686
A derivative of oxidative DNA damage and a marker for bacterial transcriptional regulation.
Grouped product items
SizePriceStock Qty
10g
$50.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

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Background

Hydroxymethyl Uracil (CAS No.: 4433-40-3) is an oxidatively modified pyrimidine base derived from cytosine damage in DNA and is widely recognized as a biomarker of oxidative stress and genomic insult in biological systems. Formed predominantly through hydroxyl radical-mediated reactions, including those associated with Fenton chemistry, this lesion reflects cellular redox imbalance and contributes to altered DNA structure and function. Hydroxymethyl uracil has been shown to influence DNA–protein interactions, thereby modulating transcriptional processes, particularly in bacterial systems where it can enhance or inhibit RNA polymerase activity depending on sequence context and local chromatin environment. As such, it is increasingly utilized in studies of DNA damage response, base excision repair pathways, and epigenetic-like regulation of gene expression. Although it does not act through a classical receptor target, its biological effects are mediated through perturbation of DNA recognition, binding affinity of transcriptional machinery, and recruitment of repair enzymes. In vitro investigations typically employ concentrations in the low micromolar to millimolar range depending on assay design, particularly in studies examining polymerase fidelity, DNA repair enzyme kinetics, or oxidative stress modeling. Hydroxymethyl uracil is therefore a valuable tool in cell-based and biochemical assays for elucidating mechanisms of oxidative DNA damage, transcriptional regulation, and the interplay between genome integrity and epigenetic signaling, with experimental conditions tailored to specific research objectives.

Chemical Properties

Physical AppearanceA solid
Storage-20°C
M.Wt142.11
Cas No.4433-40-3
FormulaC5H6N2O3
Solubilityinsoluble in H2O; insoluble in EtOH; ≥10.3 mg/mL in DMSO
Chemical Name5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
Canonical SMILESO=C1NC(C(O)=O)=C(C(N1)=O)F.O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

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