Hydroxyquinone often refers to a hydroxybenzoquinone, any

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with formula which can be viewed as a derivative of a

benzoquinone Benzoquinone (C6H4O2) is a quinone with a single benzene ring. There are 2 (out of 3 hypothetical) benzoquinones: * 1,4-Benzoquinone, most commonly, right image (also ''para''-benzoquinone, ''p''-benzoquinone, ''para''-quinone, or just quinone) * ...

through replacement of one

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atom (H) by a

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

group (-OH). When unqualified, the terms usually mean specifically the compound 2-hydroxy-1,4-benzoquinone, derived from

1,4-benzoquinone 1,4-Benzoquinone, commonly known as ''para''-quinone, is a chemical compound with the chemical formula, formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, ...

. That parent is sometimes simply called ''quinone'', and this is the only hydroxy derivative of it. More generally, the term may refer to any derivative of any

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds benzene.html" ;"title="uch as benzene">uch as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with ...

(such as

1,2-benzoquinone 1,2-Benzoquinone, also called ''ortho''-benzoquinone, is an organic compound with formula . It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is r ...

1,4-naphthoquinone 1,4-Naphthoquinone or para-naphthoquinone is a quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ethe ...

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

prefix A prefix is an affix which is placed before the stem of a word. Particularly in the study of languages, a prefix is also called a preformative, because it alters the form of the word to which it is affixed. Prefixes, like other affixes, can b ...

(mono-, di-, tri-, etc.), and the parent quinone's name is used instead of just "quinone" — as in

tetrahydroxy-1,4-benzoquinone Tetrahydroxy-1,4-benzoquinone, also called tetrahydroxy-''p''-benzoquinone, tetrahydroxybenzoquinone, or tetrahydroxyquinone (THBQ, THQ), is an organic compound with formula . Its molecular structure consists of a cyclohexadiene ring with four hyd ...

. File:Tetrahydroxy-1,4-benzoquinone-2D-skeletal.png, Tetrahydroxy-
1,4-benzoquinone File:Juglone.png, 5-Hydroxy-
1,4-naphthoquinone
(Juglone) File:Alizaryna.svg, 1,2-Dihydroxy-
9,10-anthraquinone
(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

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

groups often exhibit intramolecular

hydrogen bonding In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...

, which affects their redox properties and their

biochemical Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, ...

properties. J. Khalafy and J.M. Bruce (2002), ''Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and lphahydroxyanthraquinones''. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139. The term "hydroxyquinone" should not be confused with

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...

, the common name of benzene-1,4-diol.

Subfamilies

* Hydroxybenzoquinones * Hydroxynaphthoquinones *

Hydroxyanthraquinone In organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its var ...

References

{{reflist Hydroxyquinones