5-Hydroxymethylcytosine

Base Information

• Chemical Name: 5-Hydroxymethylcytosine
• CAS No.: 1123-95-1
• Molecular Formula: C5H7N3O2
• Molecular Weight: 141.129
• Hs Code.: 29335990
• NSC Number: 27368
• UNII: 6CD2RLN1NK
• DSSTox Substance ID: DTXSID70149990
• Nikkaji Number: J80.173I
• Wikipedia: 5-Hydroxymethylcytosine
• Wikidata: Q238535
• Mol file: 1123-95-1.mol

Synonyms:5-hydroxylmethylcytosine;5-hydroxymethylcytosine

Chemical Property of 5-Hydroxymethylcytosine

Chemical Property:

• Melting Point: >299.85°C
• Refractive Index: 1.696
• Boiling Point: 258.15°C (rough estimate)
• PKA: 8.61±0.10(Predicted)
• PSA: 92.26000
• Density: 1.658 g/cm³
• LogP: -0.16210
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 141.053826475
• Heavy Atom Count: 10
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxymethylcytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=O)NC(=C1CO)N
• Uses: 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.

Technology Process of 5-Hydroxymethylcytosine

There total 28 articles about 5-Hydroxymethylcytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Cytosine (71-30-7) → 5-hydroxymethylcytosine (1123-95-1)

Guidance literature:

With potassium hydroxide; for 0.05h; microwave irradiation;

DOI:10.1055/s-2002-35592

Reference yield: 71.0%

5-carboxyethylcytosine → 5-hydroxymethylcytosine (1123-95-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 40 ℃; for 2.25h;

DOI:10.1002/chem.201902340

Reference yield: 27.0%

5-methylcytidine (2140-61-6) → 5-methylcytosin (554-01-8) + 5-hydroxymethylcytosine (1123-95-1) + 5-hydroxymethyl-1-(β-D-ribofuranosyl)cytosine (19235-17-7)

Guidance literature:

With sodium persulfate; In water; at 75 ℃; for 4h; sodium phosphate buffer pH 7.0;

DOI:10.1246/cl.1991.1591

upstream raw materials:

(4-amino-2-(methylthio)pyrimidin-5-yl)methanol

(2-ethylmercapto-4-amino-pyrimidin-5-yl)-methanol

ethyl cytosine-5-carboxylate

5-methyldeoxycytidine

Downstream raw materials:

4-Amino-1-(1-ethoxy-ethyl)-5-hydroxymethyl-1H-pyrimidin-2-one

5-hydroxymethyl-1-(β-D-ribofuranosyl)cytosine

Cytosine

ethyl 4-N-(2-ethoxy-2-oxoethyl)-5-(hydroxymethylcytosin-1-yl)acetate

Refernces

Design, synthesis and biological evaluation of novel dual inhibitors of acetylcholinesterase and β-secretase

10.1016/j.bmc.2008.12.067

The research focuses on the design, synthesis, and biological evaluation of novel dual inhibitors targeting acetylcholinesterase (AChE) and b-secretase (BACE-1) for the treatment of Alzheimer's disease (AD). The study is grounded in the multi-target-directed ligands strategy, aiming to develop compounds that can simultaneously inhibit both AChE and BACE-1, which are implicated in the pathogenesis of AD. A series of dual inhibitors designed and synthesized in the study, with compounds 9–14, 16–24, 26–38 being the focus. These compounds incorporate various pharmacophores and isosteres such as HE, HMC, and HEA, combined with isophthalamide moieties and N-benzylpiperidine groups. The research involves the synthesis of a series of compounds, among which inhibitor 28 demonstrated potent dual inhibitory effects with IC50 values of 0.567 μM for BACE-1 and 1.83 μM for AChE. This compound also showed significant reduction in Ab production in APP transfected HEK293 cells and provided protection against H2O2-induced PC12 cell injury. The in vivo efficacy of compound 28 was further validated in APP transgenic mice, where it led to a 29% reduction in Ab1–40 production. The experiments utilized various assays, including enzyme-based assays for AChE and BACE-1, cellular Ab lowering assays in HEK293 cells, cell protective tests in PC12 cells, and animal-based experiments involving APP transgenic mice. The study employed techniques such as NMR spectroscopy, LC-MS, and HRMS for compound characterization and Autodock for molecular docking studies to elucidate the binding modes of the inhibitors with their targets.