1,3,7,9-Tetramethyluric acid

Base Information

• Chemical Name: 1,3,7,9-Tetramethyluric acid
• CAS No.: 2309-49-1
• Molecular Formula: C9H12N4O3
• Molecular Weight: 224.219
• Hs Code.: 2933990090
• European Community (EC) Number: 218-994-1
• NSC Number: 8809
• UNII: EJ939L81MY
• DSSTox Substance ID: DTXSID90177659
• Nikkaji Number: J3.707I
• Wikipedia: Theacrine
• Wikidata: Q12646548
• Metabolomics Workbench ID: 38515
• ChEMBL ID: CHEMBL143715
• Mol file: 2309-49-1.mol

Synonyms:1,3,7,9-tetramethyluric acid;tetramethyluric acid;theacrine

Chemical Property of 1,3,7,9-Tetramethyluric acid

Chemical Property:

• Vapor Pressure: 0.00156mmHg at 25°C
• Melting Point: 226℃
• Refractive Index: 1.65
• Boiling Point: 295.033 °C at 760 mmHg
• PKA: -1.93±0.20(Predicted)
• Flash Point: 121.575 °C
• PSA: 70.93000
• Density: 1.488 g/cm³
• LogP: -1.72560
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 33mg/L(room temperature)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 224.09094026
• Heavy Atom Count: 16
• Complexity: 442

Purity/Quality:

99%, ^*data from raw suppliers

TetramethyluricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(N(C1=O)C)N(C(=O)N(C2=O)C)C
• Recent ClinicalTrials: Evaluate the Effectiveness and Safety of the Alpinia Galanga Formulation, Theacrine Formulation, and Caffeine Formulation on Fatigue, Mental Acuity, and Cognitive Health
• Uses: Tetramethyluric acid is an impurity of caffeine. Caffeine is 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 1,3,7,9-Tetramethyluric acid

There total 61 articles about 1,3,7,9-Tetramethyluric 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: 90.0%

1,3,7-trimethyluric acid (5415-44-1) + methyl iodide (74-88-4) → theacrine (2309-49-1)

Guidance literature:

With potassium tert-butylate; In acetonitrile; at 20 - 90 ℃; for 12h;

Reference yield: 89.3%

1,3-dimethyl-5,6-dimethylaminopyrimidine-2,4-dione (31595-87-6) + 1,1'-carbonyldiimidazole (530-62-1) → theacrine (2309-49-1)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 12h; Large scale;

Reference yield: 87.6%

1,3-dimethyluric acid (944-73-0) + carbonic acid dimethyl ester (616-38-6) → theacrine (2309-49-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 140 ℃; Large scale;

upstream raw materials:

diazomethane

uric Acid

O-methylcaprolactim

methyl iodide

Downstream raw materials:

4,5-dimethoxy-1,3,7,9-tetramethyl-tetrahydro-purine-2,6,8-trione

8-chlorocaffeine

methylamine

Refernces

• 1、 Hazra, Somjit,Mondal, Biplab,Roy, Brindaban,Rahaman, Habibur. "Cu-Catalyzed C-H Activation Reaction: One-Pot Direct Synthesis of Xanthine and Uric Acid Derivatives from 5-Bromouracil". supporting information. p. 1757 - 1761. Retrieved 2021/08/06.
• 2、 -. "Preparation methods of three kinds of methyl uric acid compounds, intermediate and preparation method of the intermediate". Paragraph 0163; 0164; 0168. . Retrieved 2019/01/07.