Skip to Content
Merck
All Photos(3)

Documents

M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

Synonym(s):

4-Amino-2-hydroxy-5-methylpyrimidine

Sign Into View Organizational & Contract Pricing
All Photos(3)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service