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M6751

Sigma-Aldrich

5-Methylcytosine hydrochloride

≥99%

Synonym(s):

4-Amino-2-hydroxy-5-methylpyrimidine

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250 MG
$158.00
1 G
$475.00

$158.00

Available to ship onApril 22, 2025Details

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250 MG
$158.00
1 G
$475.00

About This Item

Empirical Formula (Hill Notation):
C5H7N3O · HCl
CAS Number:
58366-64-6
Molecular Weight:
161.59
EC Number:
261-223-9
MDL number:
MFCD11053426
UNSPSC Code:
41106305
PubChem Substance ID:
24897110
NACRES:
NA.51

$158.00

Available to ship onApril 22, 2025Details

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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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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7995
MKCX1968
MKCV3512
MKCT7085
MKCS5661

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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)
Absolute quantification of RNA or DNA using acid hydrolysis and mass spectrometry
Lowenthal MS, et al.
Analytical Chemistry, 6, 824-824 (2019)
Widespread occurrence of 5-methylcytosine in human coding and non-coding RNA
Squires JE, et al.
Nucleic Acids Research, 40(11), 5023-5033 (2012)
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
Rachel Deplus et al.
The EMBO journal, 32(5), 645-655 (2013-01-29)
TET proteins convert 5-methylcytosine to 5-hydroxymethylcytosine, an emerging dynamic epigenetic state of DNA that can influence transcription. Evidence has linked TET1 function to epigenetic repression complexes, yet mechanistic information, especially for the TET2 and TET3 proteins, remains limited. Here, we
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