View source for Chemistry:Hydroxyquinone

'''Hydroxyquinone''' often refers to a '''hydroxybenzoquinone''', any [[Chemistry:Organic compound|organic compound]] with formula {{chem|C|6|H|4|O|3}} which can be viewed as a derivative of a benzoquinone through replacement of one [[Chemistry:Hydrogen|hydrogen]] atom (H) by an hydroxyl group (-OH). When unqualified, the terms usually mean specifically the compound 2-hydroxy-1,4-benzoquinone, derived from 1,4-benzoquinone or ''para''-benzoquinone (which often called just "quinone").
{{multiple image|align=none
| image1 = 2-hydroxy-1,4-benzoquinone.svg| width1 = 130
| caption1 = 2-Hydroxy-<br/>1,4-benzoquinone<br/>(Hydroxyquinone)
<!-- UNCOMMENT WHEN PICS ARE AVAILABLE
| image2 = 3-Hydroxy-1,2-benzoquinone-2D.png| width2 = 150
| caption2 = 3-Hydroxy-<br/>1,2-benzoquinone
| image3 = 4-Hydroxy-1,2-benzoquinone-2D.png| width3 = 150
| caption3 = 4-Hydroxy-<br/>1,2-benzoquinone
-->
}}

More generally, the term may refer to any derivative of any [[Chemistry:Quinone|quinone]] (such as 1,2-benzoquinone, 1,4-naphthoquinone or 9,10-anthraquinone), where any number ''n'' of hydrogens have been replaced by ''n'' hydroxyls.  In this case the number ''n'' is indicated by a multiplier [[Social:Prefix|prefix]] ('''mono'''-, '''di'''-, '''tri'''-, etc.), and the parent quinone's name is used instead of just "quinone" — as in [[Chemistry:Tetrahydroxy-1,4-benzoquinone|tetrahydroxy-1,4-benzoquinone]].
{{multiple image|align=none
| image1 = Tetrahydroxy-1,4-benzoquinone-2D-skeletal.png| width1 = 185
| image2 = Juglone.png|width2 = 140
| image3 = Alizarin chemical structure.png| width3 = 252
| caption1 = Tetrahydroxy-<br/>1,4-benzoquinone
| caption2 = 5-Hydroxy-<br/>1,4-naphthoquinone<br/>(Juglone)
| caption3 = 1,2-Dihydroxy-<br/>9,10-anthraquinone<br/>(Alizarin)
}}
The hydroxyquinones (in the particular or the general sense) include many biologically and industrially important compounds, and are a building block of many medicinal drugs.

Hydroxyquinones with hydroxyls adjacent to the [[Chemistry:Ketone|ketone]] groups often exhibit intramolecular hydrogen bonding, which  affects their redox properties and their [[Biology:Biochemistry|biochemical]] properties.<ref name=khalafy>
  J. Khalafy and J.M. Bruce (2002), ''Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and [alpha]-hydroxyanthraquinones''. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.
</ref>

The term "hydroxyquinone" should not be confused with [[Chemistry:Hydroquinone|hydroquinone]], the common name of benzene-1,4-diol.

==Subfamilies==
*Hydroxybenzoquinones
*[[Chemistry:Hydroxynaphthoquinone|Hydroxynaphthoquinone]]s
*Hydroxyanthraquinones

==References==
{{reflist}}


{{Sourceattribution|Hydroxyquinone|1}}