Флорглоцинол: қасиеттері, синтезі және қолданылуы

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4 benzenetriol) and pyrogallol (1,2,3 benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.

In 1855, phloroglucinol was first prepared from phloretin by the Austrian chemist Heinrich Hlasiwetz (1825–1875). A modern synthesis of phloroglucinol involves hydrolysis of benzene 1,3,5 triamine and its derivatives. Representative is the following route from trinitrobenzene. The synthesis is noteworthy because ordinary aniline derivatives are unreactive toward hydroxide. Because the triaminobenzene also exists as its imine tautomer, it is susceptible to hydrolysis.

From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116–117 °C, but the anhydrous form melts at a much higher temperature, at 218–220 °C. It does not boil intact, but it does sublime. The Hoesch reaction allows the synthesis of 1 (2,4,6 Trihydroxyphenyl)ethanone from phloroglucinol. Leptospermone can be synthesized from phloroglucinol by a reaction with isovaleroylnitrile in the presence of a zinc chloride catalyst. Pentacarbon dioxide, described in 1988 by Günter Maier and others, can be obtained by pyrolysis of 1,3,5 cyclohexanetrione (phloroglucin). Phloroglucinol readily forms 5 aminoresorcinol (aka Phloramine) in aqueous ammonia at low temperatures. Additionally, the compound can be similarly prepared from glucosides, plant extracts and resins such as quercetin, catechin and phlobaphenes. Phloroglucinols are secondary metabolites that occur naturally in certain plant species. It is also produced by brown algae and bacteria. Acyl derivatives are present in the fronds of the coastal woodfern, Dryopteris arguta or in Dryopteris crassirhizoma. The anthelmintic activity of the root of Dryopteris filix mas has been claimed to be due to flavaspidic acid, a phloroglucinol derivative. Formylated phloroglucinol compounds (euglobals, macrocarpals and sideroxylonals) can be found in Eucalyptus species. Hyperforin and adhyperforin are two phloroglucinols found in St John's wort. Humulone is a phloroglucinol derivative with three isoprenoid side chains. Two side chains are prenyl groups and one is an isovaleryl group. Humulone is a bitter tasting chemical compound found in the resin of mature hops (Humulus lupulus). Brown algae, such as Ecklonia stolonifera, Eisenia bicyclis or species in the genus Zonaria, produce phloroglucinol and phloroglucinol derivatives. Brown algae also produce a type of tannins known as phlorotannins. The bacterium Pseudomonas fluorescens produces phloroglucinol, phloroglucinol carboxylic acid and diacetylphloroglucinol.

Phloroglucinol is a reagent of the Tollens' test for pentoses. This test relies on reaction of the furfural with phloroglucinol to produce a colored compound with high molar absorptivity. A solution of hydrochloric acid and phloroglucinol is also used for the detection of lignin (Wiesner test). A brilliant red color develops, owing to the presence of coniferaldehyde groups in the lignin. A similar test can be performed with tolonium chloride. It is also part of Gunzburg reagent, an alcoholic solution of phloroglucinol and vanillin, for the qualitative detection of free hydrochloric acid in gastric juice.