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M6751

5-Methylcytosine hydrochloride

Name: 5-Methylcytosine hydrochloride
Brand: SIGMA

≥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:

58366-64-6

Molecular Weight:

161.59

NACRES:

NA.51

PubChem Substance ID:

24897110

UNSPSC Code:

41106305

EC Number:

261-223-9

MDL number:

MFCD11053426

Assay:

≥99%

Biological source:

synthetic (organic)

Form:

crystalline powder

Solubility:

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

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Properties

Product Name

5-Methylcytosine hydrochloride, ≥99%

biological source

synthetic (organic)

Quality Level

300

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

Description

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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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)

Crystal structures of B-DNA dodecamer containing the epigenetic modifications 5-hydroxymethylcytosine or 5-methylcytosine.

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

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Global Trade Item Number

SKU	GTIN
M6751-1G	04061826739037
M6751-250MG	04061834061229