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Merck
CN

SMB01402

Sigma-Aldrich

5-Hydroxymethylcytosine

≥95%

Synonym(s):

4-Amino-2-hydroxy-5-pyrimidinemethanol, 5-(Hydroxymethyl)cytosine, 5-(Oxymethyl)cytosine, Demethylbacimethrin

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About This Item

Empirical Formula (Hill Notation):
C5H7N3O2
CAS Number:
1123-95-1
Molecular Weight:
141.13
MDL number:
MFCD18432304
UNSPSC Code:
12352200

Key Documents

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biological source

synthetic

Quality Level

100

Assay

≥95%

form

powder or crystals

color

white to off-white

mp

300 °C

solubility

acetonitrile: soluble
chloroform: soluble
methanol: soluble

application(s)

cell analysis
clinical research
general analytical
life science and biopharma
metabolomics

storage temp.

2-8°C

SMILES string

OCC1=CNC(N=C1N)=O

InChI

InChI=1S/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10)

InChI key

RYVNIFSIEDRLSJ-UHFFFAOYSA-N

General description

5-Hydroxymethylcytosine is a DNA pyrimidine nitrogen base and a nucleobase analogue of cytosine, where the hydrogen at position 5 is replaced by a hydroxymethyl group. Chemically, 5-hydroxymethylcytosine is an aminopyrimidine and an intermediate metabolite in active DNA demethylation. It plays a key role in gene expression, DNA methylation, and various critical cellular functions. 5-Hydroxymethylcytosine has been shown to be a potential biomarker of cellular transformation and is involved in axonal growth, transcriptional regulation, and the action of leukemia inhibitory factor.

Application

5-Hydroxymethylcytosine finds application in metabolomics, biochemical, phytochemical, cell signaling and drug discovery research.

Features and Benefits

Versatile and adaptable for wide variety of research and metabolomics applications.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000420017
0000420017
0000381119
0000381119

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