Hydroxybenzoquinone
Encyclopedia
A hydroxybenzoquinone is any of several organic compound
s with formula , which can be viewed as derivatives of a benzoquinone through replacement of one hydrogen
atom (H) by an hydroxyl
group (-OH).
More generally, the term may mean any benzoquinone derivative where any number n of hydrogens have been replaced by n hydroxyls, so that the formula is .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
(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.
(ortho-benzoquinone) there are 9 possible isomers:
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s with formula , which can be viewed as derivatives of a benzoquinone through replacement of one hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
atom (H) by an hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
group (-OH).
More generally, the term may mean any benzoquinone derivative where any number n of hydrogens have been replaced by n hydroxyls, so that the formula is .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
Prefix
A prefix is an affix which is placed before the root of a word. Particularly in the study of languages,a prefix is also called a preformative, because it alters the form of the words to which it is affixed.Examples of prefixes:...
(mono-, di-, tri-, tetra-, penta-, or hexa-).
The unqualified term "hydroxybenzoquinone" usually means a derivative of 1,4-benzoquinone
1,4-Benzoquinone
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic. Impure samples are often dark-colored due to the presence...
. Other hydroxy- compounds can be derived from the other isomer, namely 1,2-benzoquinone
1,2-Benzoquinone
1,2-Benzoquinone, also called ortho-benzoquinone or cyclohexa-3,5-diene-1,2-dione, is a ketone, with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-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.
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-benzoquinone2,5-Dihydroxy-1,4-benzoquinone2,5-Dihydroxy-1,4-benzoquinone or 2,5-Dihydroxy-para-benzoquinone is an organic compound with formula , formally derived from 1,4-Benzoquinone by replacing two hydrogen atoms with hydroxyl groups...
- 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-benzoquinone1,2-Benzoquinone
1,2-Benzoquinone, also called ortho-benzoquinone or cyclohexa-3,5-diene-1,2-dione, is a ketone, with formula C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone....
(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 acidChloranilic acidChloranilic acid is an organic compound with the chemical formula C6H2Cl2O4....
(2,5-dichloro-3,6,-dihydroxy-1,4-benzoquinone) - HydroxynaphthoquinoneHydroxynaphthoquinoneA hydroxynaphthoquinone is any of several organic compounds with formula , which can be viewed as derivatives of a naphthoquinone through replacement of one hydrogen atom by an hydroxyl group ....
- HydroxyanthraquinoneHydroxyanthraquinoneA hydroxyanthraquinone is any of several organic compounds with formula C14H9O2, which can be viewed as derivatives of an anthraquinone through replacement of one hydrogen atom by an hydroxyl group ....
- HydroxyquinoneHydroxyquinoneHydroxyquinone 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 by an hydroxyl group...