Hydroxyquinol

Hydroxyquinol

Chemical structure of hydroxyquinol
Names
Preferred IUPAC name Benzene-1,2,4-triol
Other names Hydroxyhydroquinone 1,2,4-Benzenetriol 1,2,4-Trihydroxybenzene Benzene-1,2,4-triol 4-Hydroxycatechol 2,4-Dihydroxyphenol 1,3,4-Benzenetriol 1,3,4-Trihydroxybenzene
Identifiers
CAS Number	533-73-3 checkY=
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16971 checkY
ChemSpider	10331 checkY
ECHA InfoCard
E number
KEGG	C02814 checkY
PubChem CID	10787
UNII	173O8B04RD checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H checkY Key: GGNQRNBDZQJCCN-UHFFFAOYSA-N checkY InChI=1/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H Key: GGNQRNBDZQJCCN-UHFFFAOYAX
SMILES Oc1cc(O)c(O)cc1
Properties
Chemical formula	C6H6O3
Molar mass	126.11 g/mol
Appearance	white solid
Melting point	140.5 °C (284.9 °F; 413.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Hydroxyquinol is an organic compound with the formula C₆H₃(OH)₃. It is one of three isomeric benzenetriols. The compound is a colorless solid that is soluble in water. It reacts with air to give a black insoluble solid.

Production

It is prepared industrially by acetylation of paraquinone with acetic anhydride followed by hydrolysis of the triacetate.

Historically, hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone. It can also be prepared by dehydrating fructose.

C₆H₁₂O₆ → 3 H₂O + C₆H₆O₃

Natural occurrence

Hydroxyquinol is a common intermediate in the biodegradation of many aromatic compounds. These substrates include monochlorophenols, dichlorophenols, and more complex species such as the pesticide 2,4,5-T. Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants (e.g. by soil bacteria 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.