Chemical Reactivity of Aspirin with Water

The aspirin is not very soluble in water, when water is added, the aspirin product will precipitate. Some of the other compounds, such as acetic anhydride and acetic acid, are water soluble, but salicylic acid is only slightly soluble in cold water. Except for any salicylic acid that did not react, vacuum filtration will separate the crystalline aspirin from the rest of the reaction mixture.Any contaminating salicylic acid in the aspirin should be tested for. In the final section of today’s lab, you will test a small amount of aspirin with Iron(III) chloride (FeCl₃).

Colored complexes are formed when FeCl₃ reacts with phenols (alcohol groups attached to aromatic rings). It is worth noting that salicylic acid contains the phenol functional group, whereas aspirin does not. As a result, the more salicylic acid in your aspirin, the darker the colour with FeCl₃.

Aspirin’s molecular targets and cancer prevention

Plant-derived salicylates have been used for centuries by various cultures to treat a variety of ailments such as inflammation, fever, and pain. Aspirin, a chemical derivative of salicylic acid, was synthesised and mass produced by the end of the nineteenth century and is now one of the world’s most widely used drugs. Its cardioprotective properties are well known; however, new evidence suggests that it can also act as a chemopreventive agent. Its antithrombotic and anti-inflammatory effects are mediated by the inhibition of cyclooxygenases. 

Although multiple mechanisms affecting enzyme activity, transcription factors, cellular signalling, and mitochondrial functions have been proposed, the precise mechanisms underlying its anticancer effects remain unknown.This review provides a brief overview of the major COX-dependent and independent pathways associated with aspirin’s anticancer effects. The unique ability of aspirin to acetylate biomolecules other than COX has not been thoroughly investigated, nor have all of the targets of its primary metabolite, salicylic acid, been identified. Recent reports on aspirin’s ability to acetylate multiple cellular proteins call for a thorough investigation into the role of this posttranslational modification in its anticancer effects. 

Chemical Properties of Aspirin

The most important reaction associated with the use of salicylic acid in the pharmaceutical industry is the formation of aspirin, acetylsalicylic acid. It is one of the most widely used analgesics and blood thinners. 

Salicylic acid is reacting with acetic anhydride in this reaction. It causes the hydroxyl group in salicylic acid to be acetylated, resulting in the production of acetylsalicylic acid, or aspirin. As a byproduct of this reaction, acetic acid is produced. This is also present as an impurity in large-scale aspirin production. Several refining processes are required to remove these impurities from the resulting product mixture.

Characteristics of Aspirin

An experiment that incorporates organic examples is described that is appropriate for the early portion of the laboratory in a general chemistry course. It is a two-step synthesis of aspirin that begins with wintergreen oil. 

This synthesis’s mechanism includes examples of three major types of chemical reactions: hydrolysis, condensation, and proton transfer. To comprehend the chemistry, the student must be able to identify the common molecular framework shared by wintergreen oil, salicylic acid, and aspirin, as well as the -OH and -CO₂ sites where chemical changes occur.

The experiment differs from traditional aspirin synthesis experiments for general chemistry in three ways. It is intended to be performed early rather than late; it begins with a naturally occurring material and requires two steps rather than one; and it employs FTIR spectroscopy to differentiate between the oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. The application of FTIR spectroscopy introduces students to a modern analytical technique that is currently used in aspirin research.

Chemical Reactivity of Aspirin with Water

Temporary water deprivation causes significant physiological, hormonal, and enzymatic changes in the body, which can affect drug disposition kinetics, toxicity, and activity. Using aspirin, this study attempts to identify the effect of water deprivation on drug disposition kinetics. 

There were no significant effects on aspirin metabolism after a 36-hour water deprivation in rats, nor was there any effect of heparinization on aspirin disposition kinetics. The disposition of salicylic acid, on the other hand, was significantly altered, with the half-life increasing by approximately 72 percent while total body clearance decreased.

The effect of two dose levels, 5 and 10 mg/kg, was also investigated in order to understand nonlinearity in the disposition kinetic model. Aspirin was recovered almost completely in the urine, either intact or as metabolites. The fraction of salicyluric acid excreted at the 10-mg/kg dose was significantly lower than at the 5-mg/kg dose. However, the effect of water deprivation was uniform at both dose levels and had no effect on salicyluric acid excretion. 

Given the significant changes in the disposition characteristics of salicylates with water deprivation, it is suggested that due care be taken in adjusting doses while keeping body hydration levels in mind.

Conclusion

The aspirin is not very soluble in water, when water is added, the aspirin product will precipitate. Except for any salicylic acid that did not react, vacuum filtration will separate the crystalline aspirin from the rest of the reaction mixture. As a result, the more salicylic acid in your aspirin, the darker the colour with FeCl₃. Aspirin, a chemical derivative of salicylic acid, was synthesised and mass produced by the end of the nineteenth century and is now one of the world’s most widely used drugs. The most important reaction associated with the use of salicylic acid in the pharmaceutical industry is the formation of aspirin, acetylsalicylic acid. It causes the hydroxyl group in salicylic acid to be acetylated, resulting in the production of acetylsalicylic acid, or aspirin. The application of FTIR spectroscopy introduces students to a modern analytical technique that is currently used in aspirin research.