Sodium salicylate


Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenoxide and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized by refluxing methyl salicylate with an excess of sodium hydroxide.

Properties

Sodium salicylate is of the salicylate family. It is a shiny white powder with an aromatic flavor. It has a molecular weight of 160.10 g/mol, and produces mildly alkaline solutions because it can donate 1 hydrogen-bond and accept 3.

Synthesis

Sodium salicylate is industrially prepared via the Kolbe-Schmitt process, by reacting sodium phenoxide with carbon dioxide at around 120 °C and 5 atm in a mixed alcohol solvent containing excess phenol.
C6H5O- Na+ + CO2 -> HOC6H4COO- Na+
This reaction proceeds via a nucleophilic addition-elimination mechanism.
Sodium salicylate can be prepared by neutralizing salicylic acid with a sodium base such as sodium hydroxide or sodium carbonate or by refluxing methyl salicylate with sodium hydroxide.

Uses

It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug, and induces apoptosis in cancer cells and also necrosis. It is also a potential replacement for aspirin for people sensitive to it. It may also be used as a phosphor for the detection of vacuum ultraviolet radiation and beta radiation.
Sodium salicylate, alongside other salicylates, has historically been used to treat rheumatological disorders.
Sodium salicylate can be found in cosmetics, personal care products, perfumes, and fragrances, often as a preservative. Among 16 other salicylate salts in these products, it has been concluded to be safe.

Mode of action

Sodium salicylate lends its analgesic effects to the inhibition of cyclooxygenase. This enzyme converts arachidonic acid to cyclic endoperoxides, which are precursors to prostaglandins, thus preventing the sensitization of pain receptors.