CAS 1123-95-1

5-(Hydroxymethyl)cytosine

Description:

5-(Hydroxymethyl)cytosine is a modified nucleobase derived from cytosine, characterized by the presence of a hydroxymethyl group at the 5-position of the pyrimidine ring. This modification is significant in the context of epigenetics, as it plays a role in the regulation of gene expression and DNA methylation processes. The compound is typically found in DNA and is involved in various biological functions, including the modulation of chromatin structure and the influence on transcriptional activity. Its presence can affect the stability of DNA and the binding affinity of proteins involved in gene regulation. 5-(Hydroxymethyl)cytosine is also of interest in research related to cancer and developmental biology, as alterations in its levels can be indicative of certain pathological states. The substance is soluble in water and exhibits properties typical of nucleobases, such as the ability to form hydrogen bonds. Its study contributes to a deeper understanding of the molecular mechanisms underlying genetic regulation and cellular function.

Formula: C₅H₇N₃O₂

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: InChIKey=RYVNIFSIEDRLSJ-UHFFFAOYSA-N

SMILES: C(O)C1=C(N)NC(=O)N=C1

Synonyms:

• 2(1H)-Pyrimidinone, 4-amino-5-(hydroxymethyl)-
• 2(1H)-Pyrimidinone, 6-amino-5-(hydroxymethyl)-
• 2-Hydroxy-4-Amino-5-(Hydroxymethyl)Pyrimidine
• 4-Amino-2-hydroxy-5-pyrimidinemethanol
• 4-Amino-5-(hydroxymethyl)-2(1H)-pyrimidinone
• 4-Amino-5-(hydroxymethyl)pyrimidin-2-ol
• 4-amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
• 5-(Hydroxymethyl)cytosine
• 5-(Oxymethyl)cytosine
• 6-Amino-5-(hydroxymethyl)-2(1H)-pyrimidinone
• 6-amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
• Cytosine, 5-(hydroxymethyl)-
• Demethylbacimethrin

5-Hydroxymethylcytosine

CAS: 1123-95-1

Formula: C₅H₇N₃O₂

Purity: 95%

Color and Shape: Solid

Molecular weight: 141.1280

Ref: IN-DA0082O5

HM-cytosine

CAS: 1123-95-1

HM-cytosine

Purity: ≥98%

Molecular weight: 141.13g/mol

Ref: 54-BUP02445

5-Hydroxymethylcytosine

CAS: 1123-95-1

Purity: 90.0%

Color and Shape: Solid

Molecular weight: 141.1300048828125

Ref: 10-F208887

5-(Hydroxymethyl)cytosine-d2,13C (>90%)

Controlled Product

CAS: 1123-95-1

Formula: C₄CH₅D₂N₃O₂

Purity: >90%

Color and Shape: Neat

Molecular weight: 144.13

Ref: TR-H945872

5-(Hydroxymethyl)cytosine

Controlled Product

CAS: 1123-95-1

Applications 5-(Hydroxymethyl)cytosine is a DNA pyrimidine nitrogen base.It may regulate gene expression or prompt DNA demethylation. 5-Hydroxymethylcytosine may be especially important in the central nervous system, as it is found in very high levels there.
References Guo, J., et al.:Cell 145, 423 (2011); Globisch, D., et al.: PLoS ONE 5, e15367 (2010)

Formula: C₅H₇N₃O₂

Color and Shape: Neat

Molecular weight: 141.13

Ref: TR-H945870

5-Hydroxymethylcytosine

CAS: 1123-95-1

5-Hydroxymethylcytosine is a metabolite of the nucleic acid cytosine. It is an epigenetic modification that alters gene expression without changing the DNA sequence. 5-Hydroxymethylcytosine has been shown to be a potential biomarker of cellular transformation and is involved in axonal growth, transcriptional regulation, and leukemia inhibitory factor. 5-Hydroxymethylcytosine binds to nuclear dna, which inhibits replication by binding to the duplexes of dna (the double helix) and halting transcriptional elongation. 5-Hydroxymethylcytosine also binds cell factor, which is necessary for cell proliferation and differentiation.

Formula: C₅H₇N₃O₂

Purity: Min. 95 Area-%

Color and Shape: Off-White Powder

Molecular weight: 141.13 g/mol

Ref: 3D-FH35238

HM-cytosine

CAS: 1123-95-1

5-Hydroxymethylcytosine (5hmC), a modified cytosine, is a sixth base of DNA and aids in active DNA demethylation.

Formula: C₅H₇N₃O₂

Purity: 99.89%

Color and Shape: Solid

Molecular weight: 141.13

Ref: TM-T35363