A methylated derivative of cytosine
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5-Methylcytosine

Item No. 38741

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-amino-5-methyl-2(1H)-pyrimidinone
CAS Number
554-01-8
Synonyms
  • m5C
  • NSC 137776
Molecular Formula
C5H7N3O
Formula Weight
125.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
276 nm
SMILES
O=C1N=CC(C)=C(N1)N
InChi Code
InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)
InChi Key
LRSASMSXMSNRBT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 g

    $39

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    5 g

    $174

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    10 g

    $308

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    Product Description

    5-Methycytosine is a methylated derivative of the pyrimidine base cytosine (Item No. 36219) and its presence in DNA is generally associated with reduced gene transcription.1,2 Increased levels of 5-methylcytosine have been found in non-expressed and untranslated DNA sequences, and levels of 5-methylcytosine are increased on developmental genes to reduce aberrant expression in adults.2 5-Methylcytosine is also found in the tRNA, mRNA, and rRNA from bacteria, archaea, and eukaryotes.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Berg, J.M., Tymoczko, J.L., and Stryer, L. Nucleotide biosynthesis. Biochemistry (2002).

    2. Breiling, A., and Lyko, F. Epigenetic regulatory functions of DNA modifications: 5-Methylcytosine and beyond. Epigenetics Chromatin 8, 24 (2015).

    3. Edelheit, S., Schwartz, S., Mumbach, M.R., et al. Transcriptome-wide mapping of 5-methylcytidine RNA modifications in bacteria, archaea, and yeast reveals m5C within archaeal mRNAs. PLoS Genetics 9(6), e1003602 (2013).