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M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

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Synonym(s):
4-Amino-2-hydroxy-5-methylpyrimidine
Empirical Formula (Hill Notation):
C5H7N3O · HCl
CAS Number:
Molecular Weight:
161.59
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

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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This Item
C3506I6875A4660
Cytosine ≥99%

Sigma-Aldrich

C3506

Cytosine

5-Iodocytosine

Sigma-Aldrich

I6875

5-Iodocytosine

6-Thioguanine Hybri-Max™, 50 ×, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma

Sigma-Aldrich

A4660

6-Thioguanine

assay

≥99%

assay

≥99%

assay

≥99% (TLC)

assay

~98%

form

crystalline powder

form

powder

form

powder

form

lyophilized powder

solubility

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

solubility

0.5 M HCl: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

solubility

formic acid: 50 mg/mL

solubility

1 M NaOH: 50 mg/mL, clear to slightly hazy

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

200

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

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Customers Also Viewed

Slide 1 of 4

1 of 4

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)
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
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.

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