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In general, the term may mean any benzoquinone derivative where any number n of hydrogens have been replaced by n hydroxyls, so that the formula is C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-1a,4a-dihydrobenzene-1,4-dione (= 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)
2,3-Dihydroxy-1,4-benzoquinone (C
₆H
₄O
₄)
2,5-Dihydroxy-1,4-benzoquinone (C
₆H
₄O
₄)
2,6-Dihydroxy-1,4-benzoquinone (C
₆H
₄O
₄)
2,3,5-Trihydroxy-1,4-benzoquinone (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:

3-Hydroxy-1,2-benzoquinone (C
₆H
₄O
₃)
4-Hydroxy-1,2-benzoquinone (C
₆H
₄O
₃)
3,4-Dihydroxy-1,2-benzoquinone (C
₆H
₄O
₄)
3,5-Dihydroxy-1,2-benzoquinone (C
₆H
₄O
₄)
3,6-Dihydroxy-1,2-benzoquinone (C
₆H
₄O
₄)
4,5-Dihydroxy-1,2-benzoquinone (C
₆H
₄O
₄)
3,4,5-Trihydroxy-1,2-benzoquinone (C
₆H
₄O
₅)
3,4,6-Trihydroxy-1,2-benzoquinone (C
₆H
₄O
₅)
3,4,5,6-Tetrahydroxy-1,2-benzoquinone (C
₆H
₄O
₆)

References

^ Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
^ Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.

[thomson71-1] Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.

[thomson87-2] Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.

[1]

[2]

List of compounds

From 1,4-benzoquinone

From 1,2-benzoquinone

See also

References