The pain reliving power of salicylic acid has been known for hundreds of years. Hippocrates recommended willow bark to relieve the pain of childbirth. (1) The active ingredient was later isolated by Leroux. Sodium salicylate was used as a treatment for rheumatiod arthritis in the late 1800s, but chronic patients suffered from severe stomach irritation. The father of a Baeyer chemist asked his son to search for a less irritating drug than sodium salicylate. Many derivatives were made, and the acetylated version found to be the best. Before the end of the century Baeyer had acetylsalicylic acid, or asprin, on the market.
The mechanism of action for asprin was determined much later. Asprin inhibits prostaglandin biosynthesis. Prostaglandins are released when cells are damaged and result in inflammation and fever. Asprin inhibits palatlet cyclooxygenase for the life of the platelet. Asprin acetylates a serine hydroxyl group in the active site of cyclooxygenase buy what can be thought of as a transesterification reaction. (2)
(1) Gross, M. and Greenberg, L. A. "The Salicylates: A Critical Bibliographical Review." Hillman: New Haven, CT.
(2) Van der Ouderaa, F. J., Buytenhek, M., Nugteren, D. H., and Van Dorp, D. A. 1980, Eur. J. Biochem. 109, 1.
1 comment:
Interesting one. Hope i could get the same for Acetate. Thanks for sharing this. Quite easy for me :)
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