Date published: 2025-12-17

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5-Methylcytosine HCl (CAS 58366-64-6)

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Alternate Names:
4-Amino-2-hydroxy-5-methylpyrimidine
Application:
5-Methylcytosine HCl is Useful in studying DNA methylation
CAS Number:
58366-64-6
Purity:
≥98%
Molecular Weight:
161.59
Molecular Formula:
C5H7N3O•HCl
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-Methylcytosine HCl (5-mC) is a naturally occurring modified form of cytosine, one of the DNA bases. It plays a significant role as an epigenetic modification, exerting an impact on gene expression. Researchers have utilized 5-Methylcytosine HCl in a wide array of scientific research applications. It has proven instrumental in studying the underlying mechanisms of gene regulation, exploring the influence of DNA methylation on gene expression, and investigating the association between DNA methylation. The effects of 5-Methylcytosine HCl on gene expression stem from its ability to modify the chromatin structure of cells. This modification is believed to alter the accessibility of DNA to regulatory proteins and transcription factors, thereby influencing gene expression.


5-Methylcytosine HCl (CAS 58366-64-6) References

  1. Theoretical and experimental investigations on the chemical reactions of positively charged phenyl radicals with cytosine and 1-methylcytosine.  |  Huang, Y. and Kenttämaa, H. 2003. J Am Chem Soc. 125: 9878-89. PMID: 12904056
  2. EPR and ENDOR study of crystalline cytosine x HCl doped with 5-methylcytosine. Radiation-induced radical formation and hole transfer.  |  Krivokapić, A., et al. 2003. Radiat Res. 160: 340-54. PMID: 12926993
  3. Characterization of free radicals in gamma-irradiated polycrystalline uridine 5'-monophosphate: a study combining ESR, spin-trapping and HPLC.  |  Hiraoka, W., et al. 1991. Int J Radiat Biol. 59: 875-83. PMID: 1674273
  4. Primary oxidation products of 5-methylcytosine: methyl dynamics and environmental influences.  |  Krivokapić, A., et al. 2009. J Phys Chem A. 113: 9633-40. PMID: 19663491
  5. Radicals in 5-methylcytosine induced by ionizing radiation. Electron magnetic resonance for structural and mechanistic analyses.  |  Krivokapić, A., et al. 2010. Radiat Res. 173: 689-702. PMID: 20426669
  6. Near-IR-induced, UV-induced, and spontaneous isomerizations in 5-methylcytosine and 5-fluorocytosine.  |  Lapinski, L., et al. 2014. J Phys Chem B. 118: 2831-41. PMID: 24559084
  7. Electrospray ionization mass spectrometry of non-covalent complexes formed between N-alkylimidazolium-containing zwitterionic sulfonates and protonated bases.  |  Podjava, A., et al. 2014. Eur J Mass Spectrom (Chichester). 20: 467-75. PMID: 25905871
  8. DNA methylation as a potential diagnosis indicator for rapid discrimination of rare cancer cells and normal cells.  |  Si, X., et al. 2015. Sci Rep. 5: 11882. PMID: 26139010
  9. Ring-opening photoreactions of cytosine and 5-methylcytosine with aliphatic alcohols.  |  Shaw, AA. and Shetlar, MD. 1989. Photochem Photobiol. 49: 267-71. PMID: 2734363
  10. The photochemistry of 2-alkoxycytosines in phosphate buffer and its link to cytosine photochemistry in alcoholic solution.  |  Shaw, AA. and Shetlar, MD. 1989. Photochem Photobiol. 49: 273-7. PMID: 2734364
  11. Utilizing online-dual-SPE-LC with HRMS for the simultaneous quantification of amphotericin B, fluconazole, and fluorocytosine in human plasma and cerebrospinal fluid.  |  Qu, L., et al. 2017. Talanta. 165: 449-457. PMID: 28153282
  12. Genome-wide identification of mRNA 5-methylcytosine in mammals.  |  Huang, T., et al. 2019. Nat Struct Mol Biol. 26: 380-388. PMID: 31061524
  13. Absolute Quantification of RNA or DNA Using Acid Hydrolysis and Mass Spectrometry.  |  Lowenthal, MS., et al. 2019. Anal Chem. 91: 14569-14576. PMID: 31638773
  14. RNA methyltransferase NSUN2 promotes gastric cancer cell proliferation by repressing p57Kip2 by an m5C-dependent manner.  |  Mei, L., et al. 2020. Cell Death Dis. 11: 270. PMID: 32332707
  15. NSUN2-mediated RNA m5C modification modulates uveal melanoma cell proliferation and migration.  |  Luo, G., et al. 2022. Epigenetics. 17: 922-933. PMID: 35757999

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

5-Methylcytosine HCl, 250 mg

sc-217223
250 mg
$103.00

5-Methylcytosine HCl, 1 g

sc-217223A
1 g
$326.00