Hydroxyquinol

Hydroxyquinol
Chemical structure of hydroxyquinol
Names
IUPAC name
benzene-1,2,4-triol
Other names
Hydroxyhydroquinone
Oxyhydroquinone
1,2,4-Benzenetriol
1,2,4-Trihydroxybenzene
Benzene-1,2,4-triol
4-Hydroxycatechol
2,5-Dihydroxyphenol
1,3,4-Benzenetriol
1,3,4-Trihydroxybenzene
Identifiers
533-73-3 YesY=
3D model (Jmol) Interactive image
ChEBI CHEBI:16971 YesY
ChemSpider 10331 YesY
ECHA InfoCard 100.007.797
KEGG C02814 YesY
PubChem 10787
Properties
C6H6O3
Molar mass 126.11 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hydroxyquinol is a benzenetriol.

Production

Hydroxyquinol is produced by various means of degradation. Historically hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone.[1] Today the chemical is more conveniently synthesized by dehydrating fructose with supercritical water:[2][3]

C6H12O6 → 3 H2O + C6H6O3

Natural Occurrence

Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants such as Bradyrhizobium japonicum.[4] 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. Roscoe, Henry (1891). A treatise on chemistry, Volume 3, Part 3. London: Macmillan & Co. p. 199.
  2. 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.
  3. 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.
  4. Mahadevan, A.; Waheeta, Hopper (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074.
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