Hydroxyquinol Explained

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.

Notes and References

1. Fiege. Helmut. Heinz-Werner. Voges. Hamamoto. Toshikazu. Umemura. Sumio. Iwata. Tadao. Miki. Hisaya. Fujita. Yasuhiro. Buysch. Hans-Josef. Garbe. Dorothea. Paulus. Wilfried. Phenol Derivatives. Ullmann's Encyclopedia of Industrial Chemistry. 2005. Wiley-VCH. Weinheim, Germany. 10.1002/14356007.a19_313. 978-3527306732.
2. Book: Roscoe, Henry. A treatise on chemistry, Volume 3, Part 3. 1891. Macmillan & Co.. London. 199.
3. Luijkx. Gerard. Rantwijk. Fred. Bekkum. Herman. Herman van Bekkum. Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose. Carbohydrate Research. 1993. 242. 1. 131–139. 10.1016/0008-6215(93)80027-C.
4. Srokol. Zbigniew. Anne-Gaëlle. Bouche. Estrik. Anton. Strik. Rob. Maschmeyer. Thomas. Peters. Joop. Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds. Carbohydrate Research. 2004. 339. 10. 1717–1726. 10.1016/j.carres.2004.04.018. 15220081.
5. Hydroxyquinol pathway for microbial degradation of halogenated aromatic compounds. Travkin, Vasili M. . Solyanikova, Inna P. . Golovleva, Ludmila A. . Journal of Environmental Science and Health, Part B . 2006. 41. 8. 1361–1382. 10.1080/03601230600964159. 17090498. 36347319.
6. Mahadevan. A.. Waheeta. Hopper. Degradation of catechin by Bradyrhizobium japonicum. Biodegradation. 1997. 8. 3. 159–165. 10.1023/A:1008254812074. 41221044.