Hydroxyquinol

Hydroxyquinol
Chemical structure of 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
Melting point 140.5 °C (284.9 °F; 413.6 K)
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.

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. 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

  1. 1 2 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.{{cite journal}}: CS1 maint: periodical has ISBN (link)
  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.