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Hydroxy-1,4-benzoquinone

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Hydroxy-1,4-benzoquinone
Names
Preferred IUPAC name 2-Hydroxycyclohexa-2,5-diene-1,4-dione
Other names 2-Hydroxy-p-benzoquinone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9HKey: GPLIMIJPIZGPIF-UHFFFAOYSA-N
  • InChI=1/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9HKey: GPLIMIJPIZGPIF-UHFFFAOYAA
SMILES
  • C1=CC(=O)C(=CC1=O)O
Properties
Chemical formula C6H4O3
Molar mass 124.1 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hydroxy-1,4-benzoquinone, also called hydroxy-para-benzoquinone, is an organic compound with formula C
6H
4O
3, formally derived from 1,4-Benzoquinone by replacing one hydrogen atom with a hydroxyl (OH) group. It is one of three hydroxybenzoquinone isomers and one of the simplest hydroxyquinones.

The compound is often called 2-hydroxy-1,4-benzoquinone, but the "2-" prefix is superfluous since there is no other hydroxy derivative of 1,4-benzoquinone. The IUPAC name is 2-hydroxycyclohexa-2,5-diene-1,4-dione.

It is formed by the reaction of 1,4-benzoquinone with hydrogen peroxide and is a byproduct of the metabolism of phenols, such as 1,2,4-benzenetriol. The enzyme 1,2,4-benzenetriol dehydrogenase catalyzes the conversion of 1,2,4-benzenetriol to 2-hydroxy-1,4-benzoquinone, and the enzyme hydroxybenzoquinone reductase catalyzes the reverse reaction. The enzyme 2-hydroxy-1,4-benzoquinone-2-reductase converts it to 1,4-benzoquinone.

It tends to dimerize spontaneously by peroxo bridges.

See also

References

  1. ^ Philipp, B; Schink, B (1998). "Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius". Journal of Bacteriology. 180 (14): 3644–9. PMC 107334. PMID 9658009.
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