1,2,3,5-Tetrahydroxybenzene

Names

Preferred IUPAC name

Benzene-1,2,3,5-tetrol

Other names

1,2,3,5-Benzenetetrol

Identifiers

CAS Number

634-94-6^N=

3D model (JSmol)

Interactive image
Interactive image

ChEBI

CHEBI:16746^Y

ChemSpider

11^Y

KEGG

C03743^Y

PubChem CID

UNII

6KQM6GV7J9^Y

CompTox Dashboard (EPA)

DTXSID90212812

InChI

InChI=1S/C6H6O4/c7-3-1-4(8)6(10)5(9)2-3/h1-2,7-10H^Y
Key: RDJUHLUBPADHNP-UHFFFAOYSA-N^Y
InChI=1/C6H6O4/c7-3-1-4(8)6(10)5(9)2-3/h1-2,7-10H
Key: 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⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is ^YN ?)

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.^[1]

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.^[2]

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.

References

^ 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.
^ Pyrogallol hydroxytransferase at www.uniprot.org