2acetoxybenzoic

2-Acetoxybenzoic acid, commonly called aspirin or acetylsalicylic acid, is an organic compound used as a medication and chemical reagent. Its IUPAC name is 2-acetoxybenzoic acid, and its chemical formula is C9H8O4. The substance appears as a white, crystalline powder with a characteristic odor and sparing water solubility.

The compound is the acetyl ester of salicylic acid (2-hydroxybenzoic acid). In its structure, a benzene ring bears a carboxylic acid group at position 1 and an acetoxy group (−OCOCH3) at position 2, giving an ortho-ester relationship to the phenolic hydroxyl that is acetylated.

Industrial preparation typically involves acetylation of salicylic acid using acetic anhydride or acetyl chloride, producing aspirin and acetic acid as a byproduct. The process yields a relatively pure white crystalline solid that can be purified by recrystallization. In the body, aspirin is hydrolyzed to salicylic acid and acetic acid; the acetyl group is responsible for many of its pharmacological properties.

Pharmacologically, 2-acetoxybenzoic acid is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic, and anti-inflammatory effects. Its primary action is the inhibition of cyclooxygenase enzymes (COX-1 and COX-2), leading to reduced prostaglandin synthesis. Low-dose use is common for cardiovascular risk prevention in select patients, while higher doses address pain and inflammation. Adverse effects can include gastrointestinal irritation, ulcers, and an increased risk of bleeding; it is contraindicated in certain conditions and populations, such as during some viral infections in children. Storage is best in a cool, dry place in a tightly closed container.