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M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

Synonym(s):

4-Amino-2-hydroxy-5-methylpyrimidine

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About This Item

Empirical Formula (Hill Notation):
C5H7N3O · HCl
CAS Number:
58366-64-6
Molecular Weight:
161.59
EC Number:
261-223-9
MDL number:
MFCD11053426
UNSPSC Code:
41106305
PubChem Substance ID:
24897110
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥99%

form

crystalline powder

solubility

water: 50 mg/mL, clear to slightly hazy, colorless

SMILES string

O=C1NC(N)=C(C)C=N1.[H]Cl

InChI

1S/C5H7N3O.ClH/c1-3-2-7-5(9)8-4(3)6;/h2H,1H3,(H3,6,7,8,9);1H

InChI key

ANWMULVRPAUPJT-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Widespread occurrence of 5-methylcytosine in human coding and non-coding RNA
Squires JE, et al.
Nucleic Acids Research, 40(11), 5023-5033 (2012)
Absolute quantification of RNA or DNA using acid hydrolysis and mass spectrometry
Lowenthal MS, et al.
Analytical Chemistry, 6, 824-824 (2019)
Daniel Renciuk et al.
Nucleic acids research, 41(21), 9891-9900 (2013-08-22)
5-Hydroxymethylcytosine (5-hmC) was recently identified as a relatively frequent base in eukaryotic genomes. Its physiological function is still unclear, but it is supposed to serve as an intermediate in DNA de novo demethylation. Using X-ray diffraction, we solved five structures
Shinpei Yamaguchi et al.
Cell research, 23(3), 329-339 (2013-02-13)
Previous studies have revealed that mouse primordial germ cells (PGCs) undergo genome-wide DNA methylation reprogramming to reset the epigenome for totipotency. However, the precise 5-methylcytosine (5mC) dynamics and its relationship with the generation of 5-hydroxymethylcytosine (5hmC) are not clear. Here
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