Acetylsalicylic acid(more commonly known as Aspirin)By Viktor Polites

HistorySalicin, derived from Willow Bark, had been used since the time of the ancient Greek philosopher, Hippocrates, to relieve dull aches and pains.Salicin is metabolized by the body to produce salicylic acid, which has similar anti-inflammatory properties to that of aspirin, but causes extreme stomach discomfort, even stomach bleeding.In 1897, Felix Hoffman, a researcher from Bayer AG synthesized acetylsalicylic acid from salicin derived from meadowsweet.In 1919, Bayer AG lost Aspirin as a registered trademark in the US, the UK, France, and Russia due to war reparations imposed by the Allies.

Chemical StructureFormula: C9H8O4Systematic name: 2-acetoxybenzoic acid Has a benzene ring backboneCarboxylic acidEster group on the 2nd carbon in benzene ring.

Physical PropertiesDensity: 1.40 g/cm3Melting Point: 135 CBoiling Point: 140 CSolubility in Water: 3 mg/mL at 20 C

Chemical PropertiesAcetylsalicylic acid slowly decomposes by hydrolysis into acetic and salicylic acids in the aqueous medium.Hydrolysis of acetylsalicylic acid is accelerated in solutions of ammonium acetate, or acetatates, carbonates, citrates, or hydroxides of the alkali metals. Acetylsalicylic acid is a weak acid with an acid dissociation constant, Ka, of 3.2 x 10^-4.

SynthesisAcetylsalicylic acid is synthesized by producing an esterification reaction of salicylic acid with acetic anyhydride. The products of this reaction are acetylsalicylic acid, and acetic acid.Dilute sulfuric acid and sometimes phosphoric acid are used as catalysts.Overall Reaction:

Salicylic acidacetic anhydride acetylsalicylic acidacetic acid

SynthesisReaction Mechanism:

UsesAspirin is a non-steroidal anti-inflammatory drug (NSAID).Aspirin is used primarily to reduce inflamation, to alleviate fevers, and to alleviate mild aches and pains.For treatment of post-surgery pain, Ibuprofen has been shown to be more effective than aspirin.Aspirin is the primary drug used to treat migraines.Aspirin, taken over a long period of time and in low doses, significantly reduces the risk of heart attack and stroke.Additionally, low doses of aspiring taken over a long period of time have recently been shown to dramatically reduce the mortality rate in cancer patients.

How Aspirin WorksAspirins anti-inflamatory, pain relieving, fever relieving, and anti-coagulant properties arise from its ability to decrease the bodys production of prostoglandins and thromboxanes.Aspirin inhibits the production of prostoglandins and thromboxanes by inactivating cyclooxygenase enzymes by acetylation of their serine residues.Unlike other NSAIDs such as ibuprofen, aspirins inactivation of cyclooxygenase is irreversible.Prostoglandins are responsible for delivering pain responses, causing fever, and causing inflamation.Thromboxanes are primarily responsible for causing blood to coagulate. Inhibition of thromboxanes by low doses of aspirin reduces the risk of heart attack or stroke.

Cyclooxygenase-2 inactivated by Aspirin

Biosynthesis of Prostacyclin and Thromboxane

Adverse Side EffectsAspirin increases the risk of gastrointestinal bleeding.Aspirin increases the risk of bleeding in hemophilic patients.In high doses over a long period of time, aspirin causes iron-deficiency anemia.Aspirin administered to children with viral infections can cause Reyes syndrome, which is characterized by brain injury and by fat buildup in the liver.Those who have an intolerance to salicylate experience hives when they take aspirin.

Works Citedhttp://en.wikipedia.org/wiki/Aspirinhttp://en.wikipedia.org/wiki/Mechanism_of_action_of_aspirinhttp://en.wikipedia.org/wiki/Cyclooxygenasehttp://en.wikipedia.org/wiki/Prostaglandinshttp://en.wikipedia.org/wiki/Thromboxanes