M6751
5-Methylcytosine hydrochloride
≥99%, synthetic (organic), crystalline powder
Synonym(s):
4-Amino-2-hydroxy-5-methylpyrimidine
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About This Item
Empirical Formula (Hill Notation):
C5H7N3O · HCl
CAS Number:
Molecular Weight:
161.59
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
261-223-9
MDL number:
Product Name
5-Methylcytosine hydrochloride, ≥99%
InChI key
ANWMULVRPAUPJT-UHFFFAOYSA-N
InChI
1S/C5H7N3O.ClH/c1-3-2-7-5(9)8-4(3)6;/h2H,1H3,(H3,6,7,8,9);1H
SMILES string
O=C1NC(N)=C(C)C=N1.[H]Cl
biological source
synthetic (organic)
assay
≥99%
form
crystalline powder
solubility
water: 50 mg/mL, clear to slightly hazy, colorless
Quality Level
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Application
5-Methylcytosine hydrochloride has been used as standard in high performance liquid chromatography (HPLC) for the estimation of global methylation rates. It has also been used in high-resolution mass spectroscopic analysis.
5-Methylcytosine is used in studies of DNA methylation processes (epigenetics).
Biochem/physiol Actions
5-Methylcytosine mediates gene expression, genomic imprinting and inhibition of transposable elements. It is closely associated with translational fidelity and tRNA recognition.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine
Ito S, et al.
Science (New York, N.Y.), 333(6047), 1300-1303 (2011)
Absolute quantification of RNA or DNA using acid hydrolysis and mass spectrometry
Lowenthal MS, et al.
Analytical Chemistry, 6, 824-824 (2019)
Widespread occurrence of 5-methylcytosine in human coding and non-coding RNA
Squires JE, et al.
Nucleic Acids Research, 40(11), 5023-5033 (2012)
Rachel Deplus et al.
The EMBO journal, 32(5), 645-655 (2013-01-29)
TET proteins convert 5-methylcytosine to 5-hydroxymethylcytosine, an emerging dynamic epigenetic state of DNA that can influence transcription. Evidence has linked TET1 function to epigenetic repression complexes, yet mechanistic information, especially for the TET2 and TET3 proteins, remains limited. Here, we
Lan Jiang et al.
Cell, 153(4), 773-784 (2013-05-15)
5-methylcytosine is a major epigenetic modification that is sometimes called "the fifth nucleotide." However, our knowledge of how offspring inherit the DNA methylome from parents is limited. We generated nine single-base resolution DNA methylomes, including zebrafish gametes and early embryos.
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