1,3,9-Trimethyluric acid

Base Information

• Chemical Name: 1,3,9-Trimethyluric acid
• CAS No.: 7464-93-9
• Molecular Formula: C8H10 N4 O3
• Molecular Weight: 210.192
• Hs Code.: 2933990090
• European Community (EC) Number: 231-258-4
• NSC Number: 400135
• DSSTox Substance ID: DTXSID10225621
• Nikkaji Number: J278.871C
• Wikidata: Q83104668
• Metabolomics Workbench ID: 47349
• Mol file: 7464-93-9.mol

Synonyms:1,3,9-TRIMETHYLURIC ACID;7464-93-9;1,3,9-trimethyl-7H-purine-2,6,8-trione;1,3,9-trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione;7,9-Dihydro-1,3,9-trimethyl-1H-purine-2,6,8(3H)-trione;EINECS 231-258-4;NSC400135;starbld0037896;1?3?9-Trimethyluric acid;SCHEMBL2449943;DTXSID10225621;CHEBI:174053;STK292817;AKOS005428251;NSC 400135;NSC-400135;1,3,9-Trimethyl-7H-purine-2,6,8(1H,3H,9H)-trione;1,3,9-trimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

Chemical Property of 1,3,9-Trimethyluric acid

Chemical Property:

• PSA: 81.79000
• LogP: -1.73600
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 210.07529019
• Heavy Atom Count: 15
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

1,3,9-TrimethyluricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C(=O)N(C(=O)N2C)C)NC1=O
• Uses: 1,3,9-Trimethyluric Acid has been found in rat urine as a metabolite of Caffeine (C080100), a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants. In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Caffeine is a cardiac and respiratory stimulant; diuretic. Caffeine is toxic at sufficiently high doses.

Technology Process of 1,3,9-Trimethyluric acid

There total 19 articles about 1,3,9-Trimethyluric acid 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: 10.0%

1,3,9-trimethyl-8-nitroxanthine → 1,3,9-trimethyluric acid (7464-93-9)

Guidance literature:

With sodium hydroxide; at 90 ℃; for 1h;

DOI:10.1002/jhet.5570300509

Reference yield:

5-amino-1,3-dimethyl-6-methylaminopyrimidine-2,4(1H,3H)-dione (61541-46-6) + 1,1'-carbonyldiimidazole (530-62-1) → 1,3,9-trimethyluric acid (7464-93-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere; Reflux;

Reference yield:

6-chloro-1,3-dimethyl-5-nitrouracil (1203-25-4) → 1,3,9-trimethyluric acid (7464-93-9)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloromethane; chloroform; water / 1 h / 20 °C / Inert atmosphere

2: hydrogen / palladium 10% on activated carbon / methanol / 20 °C

3: tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Reflux

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;

upstream raw materials:

diethyl ether

1,3-dimethyluric acid

methyl iodide

7-acetyl-1,3,9-trimethyl-uric acid

Downstream raw materials:

N-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-2-(1,3,9-trimethyl-2,6,8-trioxo-1,2,3,6,8,9-hexahydro-7H-purin-7-yl)acetamide

theacrine

7-benzyl-1,3,9-trimethyl-7,9-dihydro-3H-purine-2,6,8-trione

Refernces

• 1、 Vieira,Steenken. "Radical oxidation of xanthines: A reaction pathway to uric acid?". . p. 235 - 243. Retrieved 2007/10/03.