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Merck
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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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Categorie correlate

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)

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Coenzyme A hydrate ≥85% (UV, HPLC)

Sigma-Aldrich

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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)
Lan Jiang et al.
Cell, 153(4), 773-784 (2013-05-15)
5-methylcytosine is a major epigenetic modification that is sometimes called "the fifth nucleotide." However, our knowledge of how offspring inherit the DNA methylome from parents is limited. We generated nine single-base resolution DNA methylomes, including zebrafish gametes and early embryos.
Meelad M Dawlaty et al.
Developmental cell, 24(3), 310-323 (2013-01-29)
Tet enzymes (Tet1/2/3) convert 5-methylcytosine (5mC) to 5-hydroxymethylcytosine (5hmC) in various embryonic and adult tissues. Mice mutant for either Tet1 or Tet2 are viable, raising the question of whether these enzymes have overlapping roles in development. Here we have generated
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