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8-Hydroxyquinoline

8-Hydroxyquinoline is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.

History
8-hydroxyquinoline was first obtained by Hugo Weidel and his student Albert Cobenzl in 1880. They decarboxylated so-called oxycinchoninic acid (from cinchonine) and characterized the resulting compound as melting at about 70°C. They identified that the hydroxy group is on the benzene ring (but not its particular place) and called the compound oxyquinoline and α-quinophenol. In the following year more chemists found other ways to make the compound. Zdenko Hans Skraup discovered a way to synthesize substituted quinolines from substituted phenols and described three isomers of oxyquinoline, identifying the structure of 8-hydroxyquinoline. and his student Karl Bedall made the compound from a sulphonic acid independently at about the same time, but misidentified its structure. By 1888 azo dyes were made from the compound. In the 1920s insoluble chelates of 8-hydroxyquinoline were discovered. ==Bioactivity==
Bioactivity
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties, functioning as a transcription inhibitor. Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug. A thiol analogue, 8-mercaptoquinoline is also known. The roots of the invasive plant Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it. ==See also==
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