Hydroxyquinol: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 443865001

| PIN = Benzene-1,2,4-triol

| OtherNames = Hydroxyhydroquinone<br>1,2,4-Benzenetriol<br>1,2,4-Trihydroxybenzene<br>Benzene-1,2,4-triol<br>4-Hydroxycatechol<br>2,4-Dihydroxyphenol<br>1,3,4-Benzenetriol<br>1,3,4-Trihydroxybenzene

|Section1={{Chembox Identifiers

| CASNoOther =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 173O8B04RD

|Section2={{Chembox Properties

| Appearance = white solid

| MeltingPt =

| BoilingPt =

'''Hydroxyquinol''' is an [[organic compound]] with the formula C₆H₃(OH)₃. It is one of three isomeric [[benzenetriol]]s. The compound is a colorless solid that is soluble in water. It reacts with air to give a black insoluble solid.<ref name="Ullmann">{{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}}</ref>

==Production==

It is prepared industrially by acetylation of [[paraquinone]] with [[acetic anhydride]] followed by hydrolysis of the triacetate.<ref name="Ullmann"/>

Historically, hydroxyquinol was produced by the action of [[potassium hydroxide]] on [[hydroquinone]].<ref>{{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}}</ref> It can also be prepared by [[Dehydration reaction|dehydrating]] [[fructose]].<ref>{{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}}</ref><ref>{{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}}</ref>

:C₆H₁₂O₆ → 3 H₂O + C₆H₆O₃

==Natural occurrence==

Hydroxyquinol is a common intermediate in the biodegradation of many aromatic compounds. These substrates include mono[[chlorophenol]]s, [[dichlorophenol]]s, and more complex species such as the pesticide [[2,4,5-Trichlorophenoxyacetic acid|2,4,5-T]].<ref>{{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}}</ref> Hydroxyquinol commonly occurs in nature as a [[biodegradation]] product of [[catechin]], a [[phenol|natural phenol]] found in plants (e.g. by soil bacteria ''[[Bradyrhizobium japonicum]]'').<ref>{{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}}</ref> Hydroxyquinol is also a [[metabolite]] in some organisms. For instance, [[Hydroxyquinol 1,2-dioxygenase]] is an [[enzyme]] that uses hydroxyquinol as a [[Enzyme substrate (biology)|substrate]] with [[oxygen]] to produce [[3-hydroxy-cis,cis-muconate]].