Hydroxyquinol

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
CAS Number	533-73-3=
ChEBI	CHEBI:16971
ChemSpider	10331
Jmol 3D model	Interactive image
KEGG	C02814
PubChem	10787
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
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.