Hydroxyquinol

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.^[1]

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 Y=
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16971 Y
ChemSpider	10331 Y
ECHA InfoCard	100.007.797
KEGG	C02814 Y
PubChem CID	10787
UNII	173O8B04RD Y
CompTox Dashboard (EPA)	DTXSID3040930
InChI InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H Y Key: GGNQRNBDZQJCCN-UHFFFAOYSA-N Y 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Production

It is prepared industrially by acetylation of paraquinone with acetic anhydride followed by hydrolysis of the triacetate.^[1]

Historically, hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone.^[2] It can also be prepared by dehydrating fructose.^[3][4]

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.^[5] Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants (e.g. by soil bacteria Bradyrhizobium japonicum).^[6] 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.