519-32-4

Basic information

• Product Name: ISOCAFFEINE
• Synonyms: 2,6-DIHYDROXY-1,3,9-TRIMETHYLPURINE;1,3,9-TRIMETHYLXANTHINE;CAFFEINE IMP C;ISOCAFFEINE;3,9-dihydro-1,3,9-trimethyl-1H-purine-2,6-dione;1,3,9-TRIMETHYLXANTHINE (ISOCAFFEINE) 2, 6-DIHYDROXY-1,3,9-T;2,6-Dihydroxy-1,3,9-trimethylpurine, Isocaffeine;1,3,9- Trimethyllxanthine
• CAS NO: 519-32-4
• Molecular Formula: C₈H₁₀N₄O₂
• Molecular Weight: 194.19
• EINECS: 208-267-7
• Mol File: 519-32-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 288-290°C (dec.)
• Boiling Point: 416.8 °C at 760 mmHg
• Flash Point: 205.9 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 3.72E-07mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: Room temp
• Solubility: H2O: >20mg/mL
• PKA: 0.74±0.70(Predicted)
• BRN: 196140
• CAS DataBase Reference: ISOCAFFEINE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOCAFFEINE(519-32-4)
• EPA Substance Registry System: ISOCAFFEINE(519-32-4)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 519-32-4(Hazardous Substances Data)

Usage

Uses

Isocaffeine is an impurity of Caffeine (C080100), a xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Biochem/physiol Actions

1,3,9-Trimethylxanthine is an adenosine receptor antagonist.

InChI:InChI=1/C8H10N4O2/c1-10-4-9-5-6(10)11(2)8(14)12(3)7(5)13/h4H,1-3H3

Upstream product

• 84346-90-7 Toluene-4-sulfonate7-cyanomethyl-1,3,9-trimethyl-2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-7-ium; 
• 886-38-4 diphenylcyclopropenone 
• 84346-94-1 Toluene-4-sulfonate7-methoxycarbonylmethyl-1,3,9-trimethyl-2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-7-ium; 
• 84346-81-6 C₁₆H₁₆N₄O₃ 
• 64-18-6 formic acid 
• 61541-46-6 5-amino-1,3-dimethyl-6-methylaminopyrimidine-2,4(1H,3H)-dione 
• 1203-25-4 6-chloro-1,3-dimethyl-5-nitrouracil 
• 13992-53-5 1,3-dimethyl-6-methylamino-5-nitropyrimidine-2,4(1H,3H)-dione 
• 5770-10-5 1,3-dimethyl-6-(methylamino)-5-nitrosouracil 
• 5770-42-3 1,3-dimethyl-6-methylamino-1H-pyrimidine-2,4-dione 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 769-42-6 1,3-dimethylbarbituric acid 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 

Downstream Products

• 1073148-20-5 [(NH3)5RuTMX][ZnCl4]Cl 
• 7464-93-9 1,3,9-trimethyluric acid 

Relevant articles and documents

ETHYNYLXANTHINES, PREPARATION AND USE AS CALCIUM ION CHANNEL MODULATORS

The present invention relates to novel pharmaceutical compounds, which exhibit ability to act as calcium ion channel modulators, methods for their synthesis and the treatment and/or prevention of various diseases and disorders including deregulated calcium ion channel activity.

Generation and Properties of N7-Xanthinium Ylides: Reactions of N7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds

Xanthinium N7-ylides were generated in situ from 7-substituted 9-methylxanthinium tosylates (2) using n-BuLi in tetrahydrofuran or Et3N in MeCN.The xanthinium N7-ylides (3) generated using Et3N in MeCN reacted with diphenylcyclopropenone to give pyrone derivatives and isocaffeine in good yields.The reactions of 3a-b with dimethyl acetylenedicarboxylate or methyl propiolate (MP) afforded 5-pyrrol-1-yluracils in moderate yields.N7-Methoxycarbonylmethylide (3c) reacted with MP to give a pyrrolopteridine derivative together with a 5-pyrrol-1-yluracil derivative.Furthermore, the dihydropyrrolopurine derivative (7) , a primary 1,3-dipolar cycloaddition product, was detected by nuclear magnetic resonance measurement of the products.Keywords - xantinium N7-ylide; cycloaddition; dimethyl acetylenedicarboxylate; methyl propiolate; diphenylcyclopropenone; 5-pyrrol-1-yluracil; pyrrolopteridine; isocaffeine