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| ImageName = Chemical structure of hydroxyquinol
| ImageName = Chemical structure of hydroxyquinol
| ImageAlt = Chemical structure of hydroxyquinol
| ImageAlt = Chemical structure of hydroxyquinol
| IUPACName = benzene-1,2,4-triol
| PIN = Benzene-1,2,4-triol
| OtherNames = Hydroxyhydroquinone<br>Oxyhydroquinone<br>1,2,4-Benzenetriol<br>1,2,4-Trihydroxybenzene<br>Benzene-1,2,4-triol<br>4-Hydroxycatechol<br>2,5-Dihydroxyphenol<br>1,3,4-Benzenetriol<br>1,3,4-Trihydroxybenzene
| 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
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| CASNo_Ref = {{cascite|correct|CAS}}=
| CASNo_Ref = {{cascite|correct|CAS}}=
| CASNoOther =
| CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 173O8B04RD
| PubChem = 10787
| PubChem = 10787
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
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| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>
| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>
| MolarMass = 126.11 g/mol
| MolarMass = 126.11 g/mol
| Appearance =
| Appearance = white solid
| Density =
| Density =
| MeltingPt =
| MeltingPt =
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}}
}}
}}
}}
'''Hydroxyquinol''' is an [[organic compound]] with the formula C<sub>6</sub>H<sub>3</sub>(OH)<sub>3</sub>. 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>
'''Hydroxyquinol''' is a [[benzenetriol]].


==Production==
==Production==
It is prepared industrially by acetylation of [[paraquinone]] with [[acetic anhydride]] followed by hydrolysis of the triacetate.<ref name="Ullmann"/>
⚫
Hydroxyquinol is produced by various means of [[Chemical decomposition|degradation]]. 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=http://books.google.com/books?id=HEY9AAAAYAAJ&pg=PA199&lpg=PA199&dq=Hydroxyquinol&source=bl&ots=JQGFvahcU6&sig=blzxbXICY2I2yXZOvaDOQPjEhQU&hl=en&sa=X&ei=CqvxUMjyAor9iQLaiIG4DA&ved=0CFsQ6AEwCDhu#v=onepage&q=hydroxyquinol&f=false}}</ref> Today the chemical is more conveniently synthesized by [[Dehydration reaction|dehydrating]] [[fructose]] with [[Supercritical fluid|supercritical water]]:<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}}</ref>


⚫
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>
⚫
:C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> → 3 H<sub>2</sub>O + C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>


⚫
:C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> → 3 H<sub>2</sub>O + C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>
⚫
==Natural Occurrence==

⚫
Hydroxyquinol commonly occurs in nature as a [[biodegradation]] product of [[catechin]], a [[phenol|natural phenol]] found in plants such as ''[[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}}</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]].
⚫
==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]].


==References==
==References==
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[[Category:Hydroxyquinols| ]]
[[Category:Hydroxyquinols| ]]
{{Aromatic-stub}}

Latest revision as of 13:51, 28 April 2023

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.797 Edit this at Wikidata
KEGG
UNII
  • 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
  • Oc1cc(O)c(O)cc1
Properties
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).
checkY verify (what is checkY☒N ?)

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]

Production

[edit]

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

[edit]

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.

References

[edit]
  1. ^ a b Fiege, Helmut; Heinz-Werner, Voges; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2005). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.
  2. ^ Roscoe, Henry (1891). A treatise on chemistry, Volume 3, Part 3. London: Macmillan & Co. p. 199.
  3. ^ Luijkx, Gerard; Rantwijk, Fred; Bekkum, Herman (1993). "Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose". Carbohydrate Research. 242 (1): 131–139. doi:10.1016/0008-6215(93)80027-C.
  4. ^ Srokol, Zbigniew; Anne-Gaëlle, Bouche; Estrik, Anton; Strik, Rob; Maschmeyer, Thomas; Peters, Joop (2004). "Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds". Carbohydrate Research. 339 (10): 1717–1726. doi:10.1016/j.carres.2004.04.018. PMID 15220081.
  5. ^ Travkin, Vasili M.; Solyanikova, Inna P.; Golovleva, Ludmila A. (2006). "Hydroxyquinol pathway for microbial degradation of halogenated aromatic compounds". Journal of Environmental Science and Health, Part B. 41 (8): 1361–1382. doi:10.1080/03601230600964159. PMID 17090498. S2CID 36347319.
  6. ^ Mahadevan, A.; Waheeta, Hopper (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074. S2CID 41221044.
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