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Phloroglucinol : ウィキペディア英語版
Phloroglucinol

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Phloroglucinol is an organic compound that is used in the synthesis of pharmaceuticals and explosives. It is a phenol derivative with antispasmodic properties that is used primarily as a laboratory reagent.〔(Phloroglucinol entry at the National Library of Medicine - Medical Subject Headings )〕
Austrian chemist Heinrich Hlasiwetz (1825-1875) is remembered for his chemical analysis of phloroglucinol.
Phloroglucinol is also generally found in the flavonoid ring A substitution pattern.
== Chemistry ==
Phloroglucinol (1,3,5-benzenetriol) is a benzenetriol, found along with two isomers, 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” by the cosmetic and parapharmaceutical industries, but they cannot be by any scientifically-accepted definition.
This molecule has a unique symmetric arene substitution pattern of a trisubstituted benzene. It is a type of enol and exists in two forms, or tautomers; 1,3,5-trihydroxybenzene, which has phenol-like character, 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. Furthermore, the deprotonated intermediate in the interconversion of the two forms, referred to as an enolate anion, is important in carbonyl chemistry, in large part because it is a strong nucleophile.
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.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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