Date published: 2026-4-28

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5-Hydroxycytosine (CAS 13484-95-2)

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Alternate Names:
6-Amino-5-hydroxy-2(1H)-pyrimidinone; 4-Amino-5-hydroxy-2(1H)-pyrimidinone
CAS Number:
13484-95-2
Molecular Weight:
127.1
Molecular Formula:
C4H5N3O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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5-Hydroxycytosine (5-HC) serves as a prominent epigenetic regulator that plays a role in gene expression control and the preservation of cellular identity. Derived from cytosine, a nucleoside found in DNA and RNA, 5-Hydroxycytosine undergoes hydroxylation within the cell through the action of the enzyme TET (Ten-Eleven Translocation), participating in diverse biochemical processes. Focused on unraveling the involvement of 5-Hydroxycytosine as a vital epigenetic regulator, particularly in gene expression and cell identity regulation. It has participated in a wide range of biological mechanisms, including transcriptional regulation, DNA repair, and chromatin remodeling. In laboratory experiments, 5-Hydroxycytosine finds utility in DNA sequencing and epigenetic investigations. Notably, 5-Hydroxycytosine, as a hydroxylated derivative of cytosine, is synthesized through TET-mediated conversion of 5-methylcytosine (5-mC). Through binding with the transcription factor CTCF, 5-Hydroxycytosine recruits other transcriptional regulators and chromatin remodeling complexes, thereby stimulating gene transcription and instigating alterations in gene expression and cell identity. 5-Hydroxycytosine plays a role in DNA repair, chromatin remodeling, and is believed to contribute to stem cell differentiation processes.


5-Hydroxycytosine (CAS 13484-95-2) References

  1. Excision of 5,6-dihydroxy-5,6-dihydrothymine, 5,6-dihydrothymine, and 5-hydroxycytosine from defined sequence oligonucleotides by Escherichia coli endonuclease III and Fpg proteins: kinetic and mechanistic aspects.  |  D'Ham, C., et al. 1999. Biochemistry. 38: 3335-44. PMID: 10079077
  2. Induction of reversible complexes between eukaryotic DNA topoisomerase I and DNA-containing oxidative base damages. 7, 8-dihydro-8-oxoguanine and 5-hydroxycytosine.  |  Pourquier, P., et al. 1999. J Biol Chem. 274: 8516-23. PMID: 10085084
  3. Biological consequences of free radical-damaged DNA bases.  |  Wallace, SS. 2002. Free Radic Biol Med. 33: 1-14. PMID: 12086677
  4. DNA oxidation in Alzheimer's disease.  |  Markesbery, WR. and Lovell, MA. 2006. Antioxid Redox Signal. 8: 2039-45. PMID: 17034348
  5. Dehydration, deamination and enzymatic repair of cytosine glycols from oxidized poly(dG-dC) and poly(dI-dC).  |  Tremblay, S. and Wagner, JR. 2008. Nucleic Acids Res. 36: 284-93. PMID: 18032437
  6. The miscoding potential of 5-hydroxycytosine arises due to template instability in the replicative polymerase active site.  |  Zahn, KE., et al. 2011. Biochemistry. 50: 10350-8. PMID: 22026756
  7. Toward the identification of peripheral epigenetic biomarkers of schizophrenia.  |  Guidotti, A., et al. 2014. J Neurogenet. 28: 41-52. PMID: 24702539
  8. Molecular Dynamics Simulations of 5-Hydroxycytosine Damaged DNA.  |  Karolak, A. and van der Vaart, A. 2016. J Phys Chem B. 120: 42-8. PMID: 26654566
  9. Ligation-Mediated Polymerase Chain Reaction Detection of 8-Oxo-7,8-Dihydro-2'-Deoxyguanosine and 5-Hydroxycytosine at the Codon 176 of the p53 Gene of Hepatitis C-Associated Hepatocellular Carcinoma Patients.  |  Galli, A., et al. 2020. Int J Mol Sci. 21: PMID: 32942546
  10. Synthesis and Properties of Nucleobase-Sugar Dual Modified Nucleic Acids: 2'-OMe-RNA and scpBNA Bearing a 5-Hydroxycytosine Nucleobase.  |  Sakurai, Y., et al. 2023. J Org Chem. 88: 154-162. PMID: 36520114
  11. Formation of cytosine glycol and 5,6-dihydroxycytosine in deoxyribonucleic acid on treatment with osmium tetroxide.  |  Dizdaroglu, M., et al. 1986. Biochem J. 235: 531-6. PMID: 3741404
  12. A new nitrogen base 5-hydroxycytosine in phage N-17 DNA.  |  Kchromov, IS., et al. 1980. FEBS Lett. 118: 51-4. PMID: 6997086
  13. The sequence context-dependent mispairing of 5-hydroxycytosine and 5-hydroxyuridine in vitro.  |  Purmal, AA., et al. 1994. Ann N Y Acad Sci. 726: 361-3. PMID: 8092705
  14. Major oxidative products of cytosine, 5-hydroxycytosine and 5-hydroxyuracil, exhibit sequence context-dependent mispairing in vitro.  |  Purmal, AA., et al. 1994. Nucleic Acids Res. 22: 72-8. PMID: 8127657
  15. Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100.  |  Arashidani, K., et al. 1998. Mutat Res. 403: 223-7. PMID: 9726022

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

5-Hydroxycytosine, 1 g

sc-490656
1 g
$401.00