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1,2,3,5-Tetrahydroxybenzene

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1,2,3,5-Tetrahydroxybenzene
Chemical structure of 1,2,3,5-tetrahydroxybenzene
Chemical structure of 1,2,3,5-tetrahydroxybenzene
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name Benzene-1,2,3,5-tetrol
Other names 1,2,3,5-Benzenetetrol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6O4/c7-3-1-4(8)6(10)5(9)2-3/h1-2,7-10HKey: RDJUHLUBPADHNP-UHFFFAOYSA-N
  • InChI=1/C6H6O4/c7-3-1-4(8)6(10)5(9)2-3/h1-2,7-10HKey: RDJUHLUBPADHNP-UHFFFAOYAO
SMILES
  • Oc1cc(O)cc(O)c1O
  • Oc1cc(O)c(O)c(O)c1
Properties
Chemical formula C6H6O4
Molar mass 142.110 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

1,2,3,5-Tetrahydroxybenzene is a benzenetetrol.

It is a metabolite in the degradation of 3,4,5-trihydroxybenzoate (gallic acid) by Eubacterium oxidoreducens.

The enzyme pyrogallol hydroxytransferase uses 1,2,3,5-tetrahydroxybenzene and 1,2,3-trihydroxybenzene (pyrogallol), whereas its two products are 1,3,5-trihydroxybenzene (phloroglucinol) and 1,2,3,5-tetrahydroxybenzene.

Uses

1,2,3,5-Tetrahydroxybenzene, also known as pyrogallol, has various uses. It is used in the production of certain dyes, photographic developers, and hair dyes. Additionally, pyrogallol has been employed in traditional medicine and some cosmetic formulations due to its antioxidant properties.

See also

References

  1. J D Haddock, and J G Ferry (1993). "Initial steps in the anaerobic degradation of 3,4,5-trihydroxybenzoate by Eubacterium oxidoreducens: characterization of mutants and role of 1,2,3,5-tetrahydroxybenzene". J. Bacteriol. 175 (3): 669–673. doi:10.1128/jb.175.3.669-673.1993. PMC 196204. PMID 8423143.
  2. Pyrogallol hydroxytransferase at www.uniprot.org


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