Hydroxyquinol

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title: "Hydroxyquinol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydroxyquinols"] topic_path: "general/hydroxyquinols" source: "https://en.wikipedia.org/wiki/Hydroxyquinol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | ChemSpiderID = 10331 | KEGG_Ref = | KEGG = C02814 | InChIKey = GGNQRNBDZQJCCN-UHFFFAOYAX | StdInChI_Ref = | StdInChI = 1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H | StdInChIKey_Ref = | StdInChIKey = GGNQRNBDZQJCCN-UHFFFAOYSA-N | CASNo = 533-73-3 | CASNo_Ref = = | CASNoOther = | UNII_Ref = | UNII = 173O8B04RD | PubChem = 10787 | ChEBI_Ref = | 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 = | MeltingPtC = 140.5 | BoilingPt = | Solubility = 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.

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. It can also be prepared by dehydrating fructose.

: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). 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

References

  1. (2005). "Phenol Derivatives". Wiley-VCH.
  2. Roscoe, Henry. (1891). "A treatise on chemistry, Volume 3, Part 3". Macmillan & Co..
  3. (1993). "Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose". Carbohydrate Research.
  4. (2004). "Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds". Carbohydrate Research.
  5. (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation.

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hydroxyquinols