Hydroxybenzoquinone
A hydroxybenzoquinone (formula: C
6H
4O
3) is any of several organic compounds that can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).
In general, the term may mean any benzoquinone derivative where any number n of hydrogens have been replaced by n hydroxyls, so that the formula is C
6H
4O
2+n. In this case the number n (which is between 1 and 4) is indicated by a multiplier prefix (mono-, di-, tri-, tetra-, penta-, or hexa-).
The unqualified term "hydroxybenzoquinone" usually means a derivative of 1,4-benzoquinone. Other hydroxy- compounds can be derived from the other isomer, namely 1,2-benzoquinone or ortho-benzoquinone. The IUPAC nomenclature uses dihydrobenzenedione instead of "benzoquinone", with the necessary prefixes to indicate the positions of the carbonyl oxygens (=O) — as in (= 2,3-dihydroxy-1,4-benzoquinone).
The hydroxybenzoquinones (in the particular or the general sense) include many biologically and industrially important compounds, and are a building block of many medicinal drugs.[1][2]
List of compounds[]
From 1,4-benzoquinone[]
Due to the symmetry of the 1,4-benzoquinone (para-benzoquinone) core, there is only one distinct isomer with 1, 3, or 4 substituted hydroxyls, and three isomers with 2 hydroxyls:
- 2-Hydroxy-1,4-benzoquinone (C
6H
4O
3) - (C
6H
4O
4) - 2,5-Dihydroxy-1,4-benzoquinone (C
6H
4O
4) - (C
6H
4O
4) - (C
6H
4O
5) - 2,3,5,6-Tetrahydroxy-1,4-benzoquinone (C
6H
4O
6)
From 1,2-benzoquinone[]
From the less symmetrical 1,2-benzoquinone (ortho-benzoquinone) there are 9 possible isomers:
- (C
6H
4O
3) - (C
6H
4O
3) - (C
6H
4O
4) - (C
6H
4O
4) - (C
6H
4O
4) - (C
6H
4O
4) - (C
6H
4O
5) - (C
6H
4O
5) - (C
6H
4O
6)
See also[]
- Chloranilic acid (2,5-dichloro-3,6,-dihydroxy-1,4-benzoquinone)
- Hydroxynaphthoquinone
- Hydroxyanthraquinone
- Hydroxyquinone
- C6H4O3
- C6H4O4
- C6H4O5
- C6H4O6
References[]
- Hydroxybenzoquinones