A hydroxybenzoquinone (formula: ) is any of several
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 ...
s that can be viewed as derivatives 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).
In general, the term may mean any benzoquinone derivative where any number ''n'' of hydrogens have been replaced by ''n'' hydroxyls, so that the formula is . In this case the number ''n'' (which is between 1 and 4) 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-, tetra-, penta-, or hexa-).
The unqualified term "hydroxybenzoquinone" usually means a derivative of
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, ...
. Other hydroxy- compounds can be derived from the other isomer, namely
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 ...
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 drug
Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...
s.
[
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.
]
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 ()
*
2,3-Dihydroxy-1,4-benzoquinone ()
*
2,5-Dihydroxy-1,4-benzoquinone ()
*
2,6-Dihydroxy-1,4-benzoquinone ()
*
2,3,5-Trihydroxy-1,4-benzoquinone ()
*
2,3,5,6-Tetrahydroxy-1,4-benzoquinone ()
From 1,2-benzoquinone
From the less symmetrical
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 ...
(''ortho''-benzoquinone) there are 9 possible isomers:
*
3-Hydroxy-1,2-benzoquinone ()
*
4-Hydroxy-1,2-benzoquinone ()
*
3,4-Dihydroxy-1,2-benzoquinone ()
*
3,5-Dihydroxy-1,2-benzoquinone ()
*
3,6-Dihydroxy-1,2-benzoquinone ()
*
4,5-Dihydroxy-1,2-benzoquinone ()
*
3,4,5-Trihydroxy-1,2-benzoquinone ()
*
3,4,6-Trihydroxy-1,2-benzoquinone ()
*
3,4,5,6-Tetrahydroxy-1,2-benzoquinone ()
See also
*
Chloranilic acid
Chloranilic acid is an organic compound with the chemical formula . It is a red-orange solid. The compound is obtained by hydrolysis of chloranil:
:
It is centrosymmetric, planar molecule. It also crystallizes as a dihydrate.
Chloranilic aci ...
(2,5-dichloro-3,6,-dihydroxy-1,4-benzoquinone)
*
Hydroxynaphthoquinone A hydroxynaphthoquinone (formula: ) is any of several organic compounds that can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH).
In general, the term may mean any naphthoquinone d ...
*
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 ...
*
Hydroxyquinone
Hydroxyquinone often refers to a hydroxybenzoquinone, any organic compound with formula which can be viewed as a derivative of a benzoquinone through replacement of one hydrogen atom (H) by a hydroxyl group (-OH). When unqualified, the terms usu ...
*
C6H4O3
*
C6H4O4
*
C6H4O5
*
C6H4O6
References
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