Hydroxyquinol: Difference between revisions

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 =;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16971 ;
ChemSpider	10331 ;
ECHA InfoCard	100.007.797
KEGG	C02814 ;
PubChem CID	10787;
UNII	173O8B04RD ;
CompTox Dashboard (EPA)	DTXSID3040930 ;
	InChI InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H Key: GGNQRNBDZQJCCN-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

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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.^[1]

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.

References

^ ^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.
^ Roscoe, Henry (1891). A treatise on chemistry, Volume 3, Part 3. London: Macmillan & Co. p. 199.
^ 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.
^ 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.
^ 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.
^ Mahadevan, A.; Waheeta, Hopper (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074. S2CID 41221044.

[Ullmann-1] 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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 ==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
-|authors=Travkin, Vasili M.; Solyanikova, Inna P.; 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]].
+|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==