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Merck

M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

Sinónimos:

4-Amino-2-hydroxy-5-methylpyrimidine

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About This Item

Fórmula empírica (notación de Hill):
C5H7N3O · HCl
Número de CAS:
Peso molecular:
161.59
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

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biological source

synthetic (organic)

Quality Level

200
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

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manufacturer/tradename

BRAND 91241

manufacturer/tradename

BRAND 91253

manufacturer/tradename

BRAND 91248

manufacturer/tradename

BRAND 91236

volume

400 mL

volume

800 mL

volume

600 mL

volume

250 mL

Application

5-Methylcytosine hydrochloride has been used as standard in high performance liquid chromatography (HPLC) for the estimation of global methylation rates.[1] It has also been used in high-resolution mass spectroscopic analysis.[2]
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.[3] It is closely associated with translational fidelity and tRNA recognition.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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    Visite la Librería de documentos

    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)
    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)
    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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