Synthesis and Characterization of Aspirin - Odinity
While consumers are happy that aspirin works so well in so many areas, scientists are excited in understanding how it works and finding ways to make it work better. They have come a long way since the 1970s and realize that many more secrets await discovery. Aspirin itself is a small chemical molecule, the properties of which have been known for more than a century. However, the living body with which it must interact as a medicinal agent is most complex and not well understood despite scientific advancement. Aspirin research involves many approaches that will be discussed in more details later in the book: cut and try, educated guess, breakthroughs and setbacks, laboratory experiments, theories and controversies, synthesis of knowledge from many disciplines, clinical trials with definitive or inconclusive results, and judgments based on incomplete knowledge.
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Blood clotting is a complex process. The blood contains, besides red and white blood cells, partial cells called platelets. The disc-like platelets are produced in the bone marrow and cannot reproduce themselves because they contain no nucleus. They usually lie dormant in the blood, awakened only by chemicals released by injured tissues or a tear in the artery’s plaque. These stimulants activate the COX1 enzyme in the platelets to produce a prostaglandin, which causes the platelets to stick together, triggering the cascade of reactions that result in clotting of blood. By inhibiting COX1 from synthesizing the prostaglandin, aspirin reduces the stickiness of platelets, hence the chance of forming blood clots. For this antiplatelet purpose aspirin is uniquely effective. All other aspirin-like drugs inhibit COX temporarily, aspirin alone inhibits it permanently. One dose of aspirin has antiplatelet effects that last through the platelet’s lifetime, about ten days.
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer. To understand the chemistry, the student must be able to recognize the common molecular framework shared by oil of wintergreen, salicylic acid, and aspirin and to identify the -OH and -CO2 sites where chemical changes occur. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. It is designed to be performed early rather than late; it starts from a naturally occurring material and requires two steps rather than one; and it utilizes FTIR spectroscopy to distinguish among oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. The use of FTIR spectroscopy introduces students to a modern analytical technique that is currently used in research involving aspirin.