20041-90-1

Basic information

• Product Name: caffeidine
• Synonyms: caffeidine
• CAS NO: 20041-90-1
• Molecular Formula: C₇H₁₂N₄O
• Molecular Weight: 168.19638
• Product Categories: Amines, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 20041-90-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 452°Cat760mmHg
• Flash Point: 227.2°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 2.32E-08mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: caffeidine(CAS DataBase Reference)
• NIST Chemistry Reference: caffeidine(20041-90-1)
• EPA Substance Registry System: caffeidine(20041-90-1)

Safety Data

• Hazardous Substances Data: 20041-90-1(Hazardous Substances Data)

Usage

Uses

Caffeidine is an impurity of Caffeine (C080100), a xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeidine have also shown inhibitory activity towards cyclic nucleotide phosphodiesterases.

InChI:InChI=1/C7H12N4O/c1-8-6-5(7(12)9-2)11(3)4-10-6/h4,8H,1-3H3,(H,9,12)

Upstream product

• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 50-00-0 formaldehyd 
• 74-89-5 methylamine 

Downstream Products

• 107605-86-7 4--1-methyl-5-methylaminocarbonylimidazole 
• 107605-68-5 1-methyl-5-methylaminocarbonyl-4-imidazole 
• 107605-64-1 1-methyl-5-methylaminocarbonyl-4--N-methylamino>imidazole 
• 106260-48-4 1,3,7-Trimethyl-2-(3-nitro-phenyl)-1,2,3,7-tetrahydro-purin-6-one 
• 107605-65-2 1-methyl-5-methylaminocarbonyl-4--N-methylamino>imidazole 
• 106260-41-7 1,3,7-Trimethyl-2-((E)-styryl)-1,2,3,7-tetrahydro-purin-6-one 
• 106260-57-5 1,2,3,7-Tetramethyl-2-phenyl-1,2,3,7-tetrahydro-purin-6-one; hydrochloride 
• 107605-70-9 1-methyl-5-methylaminocarbonyl-4-(N-cinnamoyl-N-methylamino)imidazole 
• 106260-47-3 1,2,3,7-tetrahydeo-1,3,7-trimethyl-2-(2-nitrophenyl)-6H-purin-6-one 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 5176-82-9 1,3-dimethylparabanic acid 
• 7664-41-7 ammonia 
• 74-89-5 methylamine 
• 64-18-6 formic acid 

Relevant articles and documents

Screening for small molecule modulators of Hsp70 chaperone activity using protein aggregation suppression assays: Inhibition of the plasmodial chaperone PfHsp70-1

Plasmodium falciparum heat shock protein 70 (PfHsp70-1) is thought to play an essential role in parasite survival and virulence in the human host, making it a potential antimalarial drug target. A malate dehydrogenase based aggregation suppression assay was adapted for the screening of small molecule modulators of Hsp70. A number of small molecules of natural (marine prenylated alkaloids and terrestrial plant naphthoquinones) and related synthetic origin were screened for their effects on the protein aggregation suppression activity of purified recombinant PfHsp70-1. Five compounds (malonganenone A-C, lapachol and bromo-β-lapachona) were found to inhibit the chaperone activity of PfHsp70-1 in a concentration dependent manner, with lapachol preferentially inhibiting PfHsp70-1 compared to another control Hsp70. Using growth inhibition assays on P. falciparum infected erythrocytes, all of the compounds, except for malonganenone B, were found to inhibit parasite growth with IC50 values in the low micromolar range. Overall, this study has identified two novel classes of small molecule inhibitors of PfHsp70-1, one representing a new class of antiplasmodial compounds (malonganenones). In addition to demonstrating the validity of PfHsp70-1 as a possible drug target, the compounds reported in this study will be potentially useful as molecular probes for fundamental studies on Hsp70 chaperone function.

In Silico Anticipation of Metabolic Pathways Extended to Organic Chemistry Reactions: A Case Study with Caffeine Alkaline Hydrolysis and The Origin of Camellimidazoles

Camellimidazoles A–C were recently reported as natural substances in Keemun black tea. Although a “biosynthetic” route to these intriguing imidazole dimers was proposed from caffeine by the authors in this seminal report, we envisioned that a artefactual scenario, consisting of alkaline hydrolysis of caffeine and spontaneous cascade reactions with a methylene donor such as formaldehyde or methylene chloride, could also have led to their formation. To capture the diversity of molecules obtained under these conditions (i.e. alkaline treatment of caffeine/formaldehyde), an in silico MetWork-based pipeline was implemented, highlighting the sought-after camellimidazoles B and C. A wealth of further compounds were also tagged, notably comprising the herein newly described and unnatural camellimidazoles D–F that were subsequently confirmed as anticipated in silico upon extensive spectroscopic analyses. Likewise, camellimidazoles B and C could also be obtained using methylene chloride as an alternative methylene donor which may also have occurred in the initial phytochemical pipeline that implied this solvent. The current investigation emphasizes the fitness of MetWork tagging to extend the logic of in silico anticipation of metabolic pathways to organic chemistry reactions.

Alkaline hydrolysis process of caffeine and determination of hydrolysis products, using Foli-Ciocalteu-phenol reagent

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