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M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

Sinonimo/i:

4-Amino-2-hydroxy-5-methylpyrimidine

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About This Item

Formula empirica (notazione di Hill):
C5H7N3O · HCl
Numero CAS:
58366-64-6
Peso molecolare:
161.59
Numero CE:
261-223-9
Numero MDL:
MFCD11053426
Codice UNSPSC:
41106305
ID PubChem:
24897110
NACRES:
NA.51

Origine biologica

synthetic (organic)

Livello qualitativo

200

Saggio

≥99%

Forma fisica

crystalline powder

Solubilità

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

Stringa SMILE

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
ANWMULVRPAUPJT-UHFFFAOYSA-N

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Applicazioni

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).

Azioni biochim/fisiol

5-Methylcytosine mediates gene expression, genomic imprinting and inhibition of transposable elements. It is closely associated with translational fidelity and tRNA recognition.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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)
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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