Benzenetriol
Benzenetriols or trihydroxybenzenes are aromatic chemical compounds and polyphenols in which three hydroxyl groups are substituted onto a benzene ring.
These three molecules have the same molecular formula C6H6O3 (molar mass : 126.11 g/mol, exact mass : 126.031694).
The enzyme pyrogallol hydroxytransferase uses 1,2,3,5-tetrahydroxybenzene and 1,2,3-trihydroxybenzene (pyrogallol), whereas its two products are 1,3,5-trihydroxybenzene (phloroglucinol) and 1,2,3,5-tetrahydroxybenzene. This enzyme can be found in Pelobacter acidigallici..
References
See also
Hydroxyquinol
Hydroxyquinol is a benzenetriol.
Production
Hydroxyquinol is produced by various means of degradation. Historically hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone. Today the chemical is more conveniently synthesized by dehydrating D-fructose with supercritical water:
Natural Occurrence
Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants such as Bradyrhizobium japonicum. Hydroxyquinol is also a metabolite in some organisms. For instance, Hydroxyquinol 1,2-dioxygenase is an enzyme that uses hydroxyquinol as a substrate with oxygen to produce 3-hydroxy-cis,cis-muconate.
References
Phloroglucinol
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.
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.
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