5-Hydroxymethyluracil

Base Information

• Chemical Name: 5-Hydroxymethyluracil
• CAS No.: 4433-40-3
• Molecular Formula: C5H6N2O3
• Molecular Weight: 142.114
• Hs Code.: 29335990
• European Community (EC) Number: 224-636-5
• NSC Number: 20901
• UNII: 590TQ3GL34
• DSSTox Substance ID: DTXSID9063455
• Nikkaji Number: J58.058I
• Wikidata: Q27102155
• Metabolomics Workbench ID: 37265
• ChEMBL ID: CHEMBL1233360
• Mol file: 4433-40-3.mol

Synonyms:5-hydroxymethyluracil;hydroxymethyluracil

Chemical Property of 5-Hydroxymethyluracil

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 4.44E-12mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.528
• Boiling Point: 530.4 °C at 760 mmHg
• PKA: 8.46±0.10(Predicted)
• Flash Point: 274.6 °C
• PSA: 86.47000
• Density: 1.401 g/cm³
• LogP: -0.61990
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)
• Water Solubility.: Soluble in water. (50 g/L ) at 20°C, DMSO, dimethyl formamide or 100% ethanol.
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 142.03784206
• Heavy Atom Count: 10
• Complexity: 209

Purity/Quality:

5-Hydroxymethyluracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)CO
• Description: 5-Hydroxymethyluracil is a product of oxidative damage to DNA, predominantly by hydroxyl radical via the Fenton reaction. It can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.
• Uses: 5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.

Technology Process of 5-Hydroxymethyluracil

There total 55 articles about 5-Hydroxymethyluracil 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-hydroxymethyl uracil (4433-40-3)

Guidance literature:

With potassium hydroxide; In water; at 50 - 52 ℃; for 68h;

Reference yield: 46.0%

5-chloromethyluracil (3590-48-5) + ethylene glycol (107-21-1) → 5-hydroxymethyl uracil (4433-40-3) + 5-<(2-hydroxyethoxy)methyl>uracil (88459-62-5)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; for 24h; Title compound not separated from byproducts;

DOI:10.1002/jhet.5570210103

Reference yield: 41.0%

thymin (65-71-4,28806-14-6,691841-57-3) → 5-hydroxymethyl uracil (4433-40-3) + 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (1195-08-0)

Guidance literature:

With sodium persulfate; In water; at 85 - 90 ℃; for 7h;

DOI:10.1246/cl.1986.1319

upstream raw materials:

5-(aminomethyl)-2,4(1H,3H)-pyrimidinedione

formaldehyd

uracil

5-chloromethyluracil

Downstream raw materials:

5-methoxymethyluracil

2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

thymin

5,6-dihydrothymine

Refernces

• 1、 Kleinsmann, Alexander J.,Weckenmann, Nicole M.,Nachtsheim, Boris J.. "Phosphate-triggered self-assembly of N-[(uracil-5-yl)methyl]urea: A minimalistic urea-derived hydrogelator". . p. 9753 - 9761. Retrieved 2014.
• 2、 -. "BICYCLIC KINASE INHIBITORS AND USES THEREOF". Paragraph 613; 618. . Retrieved 2021/11/06.
• 3、 Fugger, Kasper,Bajrami, Ilirjana,Dos Santos, Mariana Silva,Young, Sarah Jane,Kunzelmann, Simone,Kelly, Geoff,Hewitt, Graeme,Patel, Harshil,Goldstone, Robert,Carell, Thomas,Boulton, Simon J.,MacRae, James,Taylor, Ian A.,West, Stephen C.. "Targeting the nucleotide salvage factor DNPH1 sensitizes BRCA-deficient cells to PARP inhibitors". . p. 156 - 165. Retrieved 2021/05/03.