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).
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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

  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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