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The studies presented demonstrate the potential to take advantage of naturally occurring chemical moieties for the synthesis of new silver carbene complexes. In particular, theobromine serves as an excellent chemical building block for such products, in part due to its ease of functionalization at the N nitrogen atom upon deprotonation. The addition of alcohols such as a hydroxyethyl group at this position appears to greatly enhance the water solubility of the resulting silver carbene complex. In fact SCC8 demonstrated a ten fold enhancement in water solubility over an analogous caffeine derivative. Like previously reported SCCs, SCC8 showed single digit μg/mL concentration MICs in vitro on all relevant CF pathogens tested including MDR strains. In vivo efficacy studies conducted have demonstrated that nebulized silver carbene complexes such as SCC1 and SCC8 have great potential in aiding in the future treatment of virulent and MDR pulmonary infections associated with CF.
Caffeine -- History, Chemical and Physical Properties …
The synthesis of specific enzymes is the underlying cause of many allergic reactions; our ingredient Quercetin supports the inhibition of this synthesis. Guarana produces a stimulating effect due to the presence of purines (caffeine, theobromine, and theophylline). It supports relaxation of the vascular muscles and bronchial tubes.
Caffeine has been an important focus in many undergraduate experimental laboratory protocols, e.g., in analytical chemistry experiments (; ; ; ; ; ; ; ; ;; ; ; ; ) and isolation from natural (; ; ; ; ; ) or commercial products (; ; ; ). Surprisingly, however, laboratory experimental procedures for the synthesis of caffeine are quite limited. In 1973, Pavia reported the synthesis of caffeine by methylation of theobromine with dimethyl sulphate (), a procedure not suitable for the undergraduate laboratory given the toxicity (carcinogenicity and mutagenicity), volatility (inhalation hazard), and environmentally hazardous nature [It has even been considered as a potential chemical weapon of war! ()] of this substance. Since then, no other undergraduate laboratory experiment about synthesis of caffeine has been reported.
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The increasing incidence of multidrug-resistant (MDR) pulmonary infections in the cystic fibrosis (CF) population has prompted the investigation of innovative silver based therapeutics. The functionalization of the naturally occurring xanthine theobromine at the N1 nitrogen atom with an ethanol substituent followed by the methylation of the N9 nitrogen atom gives the N-heterocyclic carbene precursor 1-(2-hydroxyethyl)-3,7,9-trimethylxanthinium iodide. The reaction of this xanthinium salt with silver acetate produces the highly hydrophilic silver carbene complex SCC8. The in vitro antimicrobial efficacy of this newly synthesized complex was evaluated with excellent results on a variety of virulent and MDR pathogens isolated from CF patients. A comparative in vivo study between the known caffeine derived silver carbene SCC1 and SCC8 demonstrated the ability of both complexes to improve the survival rates of mice in a pneumonia model utilizing the clinically isolated infectious strain of Pseudomonas aeruginosa PA M57-15.
Theobromine,Cocoa Extract,CAS 83-67-0 | Herb Nutritionals
Synthesis of caffeine was carried out in a microscale apparatus. Students were divided into two groups. Group 1 performed the synthesis at room temperature (Method 1) while group 2 effected the reaction at 50-60°C (Method 2). Reaction was followed by TLC and compared with standards of caffeine and theobromine. Group 1 followed the course of the reaction every 30 minutes while group 2 monitored the progress of the reaction at 40 min (total heating time).
derivatives as bronchodilators and antibacterial ..
Caffeine is one of the most widely consumed, naturally occurring, mild, and central nervous system stimulants. Its synthesis, by the N-methylation (S2 substitution) of theobromine is described as an experiment for the undergraduate organic chemistry laboratory. The N-methylation of theobromine is rapid and efficient and its progress is monitored by TLC using authentic standards. The undergraduate student also is able to observe the effect of temperature on the rate of the N-methylation reaction.