Phloroglucinol is a benzenetriol. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional.
Phloroglucinols occur naturally in certain plant species. For example, they (and sometimes their acyl dervatives) are present in the fronds of the coastal woodfern, Dryopteris arguta. Brown algae also produce phloroglucinol derivatives known as phlorotannins.
Applications
Phloroglucinol is mainly used as a coupling agent in printing. It links diazo dyes to give a fast black.
It is useful for the industrial synthesis of pharmaceuticals and explosives. It is also used as a treatment for gallstones, spasmodic pain and other related gastrointestinal disorders. It has a non-specific spasmolytic action on the vessels, bronchi, intestine, ureters and gall bladder, and is used for treating disorders of these organs.
Phloroglucinolysis is an analytical technique to study condensed tannins by mean of depolymerisation. The reaction makes use of phloroglucinol as nucleophile.
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