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:

98%,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:

bacimethrin

5-hydroxymethyl uracil

cytosine 5-methylenesulfonate

5-(1-β-D-glucopyranosyl)thiomethylcytosine

Refernces

• 1、 Privat, Eric,Sowers, Lawrence C.. "Photochemical deamination and demethylation of 5-methylcytosine". . p. 745 - 750. Retrieved 1996.
• 2、 Shao, Jie,Huang, Chun-Hua,Kalyanaraman, Balaraman,Zhu, Ben-Zhan. "Potent methyl oxidation of 5-methyl-2′-deoxycytidine by halogenated quinoid carcinogens and hydrogen peroxide via a metal-independent mechanism". . p. 177 - 182. Retrieved 2013.
• 3、 Pidugu, Lakshmi S.,Dai, Qing,Malik, Shuja S.,Pozharski, Edwin,Drohat, Alexander C.. "Excision of 5-Carboxylcytosine by Thymine DNA Glycosylase". . p. 18851 - 18861. Retrieved 2019.
• 4、 Schmidl, David,Jonasson, Niko S. W.,Korytiaková, Eva,Carell, Thomas,Daumann, Lena J.. "Biomimetic Iron Complex Achieves TET Enzyme Reactivity**". . p. 21457 - 21463. Retrieved 2021.
• 5、 Jonasson, Niko S. W.,Jan?en, Rachel,Menke, Annika,Zott, Fabian L.,Zipse, Hendrik,Daumann, Lena J.. "TET-Like Oxidation in 5-Methylcytosine and Derivatives: A Computational and Experimental Study". . p. 3333 - 3340. Retrieved 2021/09/25.
• 6、 Jonasson, Niko S. W.,Daumann, Lena J.. "5-Methylcytosine is Oxidized to the Natural Metabolites of TET Enzymes by a Biomimetic Iron(IV)-Oxo Complex". . p. 12091 - 12097. Retrieved 2019/08/07.