5415-44-1

Basic information

• Product Name: 1,3,7-TRIMETHYLURIC ACID
• Synonyms: 1,3,7-Trimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione;1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-1,3,7-trimethyl-;7,9-dihydro-1,3,7-trimethyl-1h-purine-2,6,8(3h)-trione;8(3h)-trione,7,9-dihydro-1,3,7-trimethyl-1h-purine-6;Ba 2753;ba2753;Uric acid, 1,3,7-trimethyl-;2,6,8-TRIHYDROXY-1,3,7-TRIMETHYLPURINE
• CAS NO: 5415-44-1
• Molecular Formula: C₈H₁₀N₄O₃
• Molecular Weight: 210.19
• EINECS: 226-507-9
• Mol File: 5415-44-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: 349.7°C (rough estimate)
• Flash Point: 242.1°C
• Appearance: /
• Density: 1.3649 (rough estimate)
• Refractive Index: 1.6590 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 5.85±0.70(Predicted)
• Water Solubility: 24mg/L(room temperature)
• CAS DataBase Reference: 1,3,7-TRIMETHYLURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,7-TRIMETHYLURIC ACID(5415-44-1)
• EPA Substance Registry System: 1,3,7-TRIMETHYLURIC ACID(5415-44-1)

Safety Data

• WGK Germany: 2
• RTECS: UP0783750
• Hazardous Substances Data: 5415-44-1(Hazardous Substances Data)

Usage

Description

1,3,7-Trimethyluric Acid is an oxopurine derivative, which is a methyl derivative of uric acid and a metabolite of caffeine. It is characterized by the presence of oxo groups at positions 2, 6, and 8 on the purine ring, and the nitrogens at positions 1, 3, and 7 are substituted by methyl groups.

Uses

Used in Pharmaceutical Industry:
1,3,7-Trimethyluric Acid is used as a urine marker for caffeine consumption, helping to monitor and assess an individual's caffeine intake. This can be particularly useful in research studies and clinical settings where caffeine consumption needs to be tracked or controlled.
Used in Research and Diagnostics:
1,3,7-Trimethyluric Acid serves as a valuable biomarker in the field of research and diagnostics, particularly in the study of caffeine metabolism and its effects on the human body. It can be used to investigate the metabolic pathways of caffeine and its potential interactions with other substances or conditions.
Used in Toxicology:
In toxicology, 1,3,7-Trimethyluric Acid can be employed as a tool to assess the potential toxic effects of caffeine and its metabolites. By monitoring the levels of this compound in biological samples, researchers can gain insights into the safety and potential risks associated with caffeine consumption.
Used in Sports Medicine:
1,3,7-Trimethyluric Acid can be utilized in sports medicine to monitor caffeine use among athletes, as caffeine is a known performance-enhancing substance. By tracking the levels of this metabolite, anti-doping agencies can ensure fair competition and adherence to regulations regarding caffeine use in sports.

Purification Methods

Crystallise it from water and dry it at 100o in a vacuum. It has UV: 289nm (pH 2.5). [Beilstein 26 III/IV 2623.]

InChI:InChI=1/C8H10N4O3/c1-10-5-4(9-7(10)14)6(13)12(3)8(15)11(5)2/h1-3H3,(H,9,14)

Upstream product

• 69-93-2 uric Acid 
• 74-88-4 methyl iodide 
• 108876-77-3 8-(2-dimethylamino-ethoxy)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione; hydrochloride 
• 7647-01-0 hydrogenchloride 
• 6279-37-4 8-phenoxycaffeine 
• 54729-62-3 6-amino-1,3-dimethyl-5-(methylamino)pyrimidin-2,4-dione 
• 616-38-6 carbonic acid dimethyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 54107-71-0 6-amino-5-chloro-1,3-dimethylpyrimidin-2,4-dione 
• 7150-04-1 6-amino-5-bromo-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 94-36-0 dibenzoyl peroxide 
• 58-55-9 theophylline 

Downstream Products

• 569-34-6 8-methoxycaffeine 
• 5426-50-6 8-Ethylcoffein 
• 2309-49-1 theacrine 
• 615-35-0 N,N'-dimethyloxamide 
• 598-50-5 N-Methylurea 
• 2757-85-9 1,3-dimethylalloxan 
• 4921-49-7 8-chlorocaffeine 
• 74-89-5 methylamine 
• 7664-41-7 ammonia 
• 57-13-6 urea 
• 5176-82-9 1,3-dimethylparabanic acid 
• 1022129-88-9 3,8-dimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone 

Relevant articles and documents

Relative contribution of rat cytochrome P450 isoforms to the metabolism of caffeine: The pathway and concentration dependence

The aim of the present study was to estimate the relative contribution of rat P450 isoforms to the metabolism of caffeine and to assess the usefulness of caffeine as a marker substance for estimating the activity of P450 in rat liver and its potential for

The relative contribution of human cytochrome P450 isoforms to the four caffeine oxidation pathways: An in vitro comparative study with cDNA-expressed P450s including CYP2C isoforms

The aim of the present study was to estimate the relative contribution of cytochrome P450 isoforms (P450s), including P450s of the CYP2C subfamily, to the metabolism of caffeine in human liver. The experiments were carried out in vitro using cDNA-expresse

Br?nsted acid catalysis in the oxidation of purine based alkaloids by Mn(VII) in aqueous acetonitrile and sodium fluoride medium: A kinetic approach

Br?nsted acid (HClO4, H2SO4) catalyzed Mn(VII) oxidation of purine alkaloids such as caffeine, theophylline and theobromine in aqueous acetonitrile and sodium fluoride medium revealed first order kinetics in both [(Mn(VII)] and [Alkaloid] at constant acidity and temperature. Sodium fluoride was added to the reaction mixture in order to avoid/suppress auto catalytic reaction due to the generation of Mn(III) and Mn(IV) species during the course of Mn(VII) oxidations in acidic solutions. An increase in the Br?nsted acids (HClO4, H2SO4) concentration accelerated the rate of oxidation. Rate enhancements observed here in are analyzed by Zucker-Hammett, Bunnett and Bunnett-Olsen criteria of acidity functions. On the basis of observed Bunnett-Olsen criteria of acidity functions, the most plausible mechanism has been proposed with the involvement of water molecule in the slow step (as proton transferring agent).

Preparation methods of three kinds of methyl uric acid compounds, intermediate and preparation method of the intermediate

The invention provides preparation methods of three types of compounds which can be extracted from plants such as tea trees and have the effects of resisting depression, tranquilizing and hypnosis, resisting inflammation and easing pain, reducing stress damage of the liver cells and improving the exercise ability, an intermediate and a preparation method of the intermediate. The method is simple and convenient to operate, high in safety, high in atom economy and less in three wastes, and the raw and auxiliary materials are cheap and easy to obtain, low in toxicity, safe and stable; the reaction conditions are mild, the impurities are few, and the yield is high. The product is purified by crystallization, column chromatography is avoided, the operation is simple and feasible, and the process is stable, easy to control and convenient in reaction after-treatment, and can be economically and conveniently used for industrial production.