:Hydroxyquinol
{{chembox
| Watchedfields = changed
| verifiedrevid = 443865001
| Name = Hydroxyquinol
| ImageFile = Hydroxyhydrochinon.svg
| ImageSize = 120px
| ImageName = Chemical structure of hydroxyquinol
| ImageAlt = Chemical structure of hydroxyquinol
| PIN = Benzene-1,2,4-triol
| OtherNames = 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
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10331
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02814
| InChIKey = GGNQRNBDZQJCCN-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GGNQRNBDZQJCCN-UHFFFAOYSA-N
| CASNo = 533-73-3
| CASNo_Ref = {{cascite|correct|CAS}}=
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 173O8B04RD
| PubChem = 10787
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16971
| SMILES = Oc1cc(O)c(O)cc1
| InChI = 1/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
| MeSHName =
}}
|Section2={{Chembox Properties
| Formula = C6H6O3
| MolarMass = 126.11 g/mol
| Appearance = white solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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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.{{cite journal|last1=Fiege|first1=Helmut|last2=Heinz-Werner|first2=Voges|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|title=Phenol Derivatives|journal=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|location=Weinheim, Germany|doi=10.1002/14356007.a19_313|isbn=978-3527306732}}
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.{{cite book|last=Roscoe|first=Henry|title=A treatise on chemistry, Volume 3, Part 3|year=1891|publisher=Macmillan & Co.|location=London|pages=199|url=https://books.google.com/books?id=HEY9AAAAYAAJ&q=hydroxyquinol&pg=PA199}} It can also be prepared by dehydrating fructose.{{cite journal|last1=Luijkx|first1=Gerard|last2=Rantwijk|first2=Fred|last3=Bekkum|first3=Herman|author-link3=Herman van Bekkum|title=Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose|journal=Carbohydrate Research|date=1993|volume=242|issue=1|pages=131–139|doi=10.1016/0008-6215(93)80027-C}}{{cite journal|last1=Srokol|first1=Zbigniew|last2=Anne-Gaëlle|first2=Bouche|last3=Estrik|first3=Anton|last4=Strik|first4=Rob|last5=Maschmeyer|first5=Thomas|last6=Peters|first6=Joop|title=Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds|journal=Carbohydrate Research|date=2004|volume=339|issue=10|pages=1717–1726|doi=10.1016/j.carres.2004.04.018|pmid=15220081}}
: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.{{cite journal|title=Hydroxyquinol pathway for microbial degradation of halogenated aromatic compounds
|author1=Travkin, Vasili M. |author2=Solyanikova, Inna P. |author3=Golovleva, Ludmila A. |journal=Journal of Environmental Science and Health, Part B |year=2006|volume=41|issue=8|pages=1361–1382|doi=10.1080/03601230600964159|pmid=17090498|s2cid=36347319}} Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants (e.g. by soil bacteria Bradyrhizobium japonicum).{{cite journal|last1=Mahadevan|first1=A.|last2=Waheeta|first2=Hopper|title=Degradation of catechin by Bradyrhizobium japonicum|journal=Biodegradation|date=1997|volume=8|issue=3|pages=159–165|doi=10.1023/A:1008254812074|s2cid=41221044}} 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.