Dihydroxyanthraquinone
Encyclopedia
A dihydroxyanthraquinone is any of several isomer
ic organic compound
s with formula , formally derived from an anthraquinone
by replacing two hydrogen
atoms by hydroxyl
groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl
oxygen
s (=O) of the underlying anthraquinone.
occurs widely in natural products, and is an important feature of the anthracycline antitumour antibiotics. In particular, 1,8-Dihydroxy-9,10-anthraquinone is the precursor for the important topical antipsoriatic drug anthralin, 1,8-dihydroxy-9-anthrone,
There are 28 ways of choosing two of the 8 possible hydrogens, but because of the four-fold symmetry of the 9,10-anthraquinone core there are only 10 distinct isomers.
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
ic organic compound
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 , formally derived from an anthraquinone
Anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene is an aromatic organic compound with formula . Several isomers are possible, each of which can be viewed as a quinone derivative...
by replacing two 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...
atoms by 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...
groups. Dihyroxyantraquinones have been studied since the early 1900s, and include some compounds of historical and current importance. The isomers differ in the position of the hydroxyl groups, and of the carbonyl
Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....
oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
s (=O) of the underlying anthraquinone.
From 9,10-anthraquinone
The unqualified term "dihydroxyanthraquinone" usually means a hydroxy derivative of 9,10-anthraquinone. The dihydroxy-9,10-anthraquinone functional groupFunctional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
occurs widely in natural products, and is an important feature of the anthracycline antitumour antibiotics. In particular, 1,8-Dihydroxy-9,10-anthraquinone is the precursor for the important topical antipsoriatic drug anthralin, 1,8-dihydroxy-9-anthrone,
There are 28 ways of choosing two of the 8 possible hydrogens, but because of the four-fold symmetry of the 9,10-anthraquinone core there are only 10 distinct isomers.
- 1,2-Dihydroxyanthraquinone (alizarin)
- 1,3-Dihydroxyanthraquinone1,3-Dihydroxyanthraquinone1,3-Dihydroxyanthraquinone, also called purpuroxanthin or xanthopurpurin is an organic compound with formula that occurs in the plant Rubia cordifolia . It is one of ten dihydroxyanthraquinone isomers...
(purpuroxanthin, xantopurpurin) - 1,4-Dihydroxyanthraquinone1,4-Dihydroxyanthraquinone1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl groups...
(quinizarin) - 1,5-Dihydroxyanthraquinone (anthrarufin)
- 1,6-Dihydroxyanthraquinone
- 1,7-Dihydroxyanthraquinone
- 1,8-Dihydroxyanthraquinone (dantron, chrysazin)
- 2,3-Dihydroxyanthraquinone
- 2,6-Dihydroxyanthraquinone
- 2,7-Dihydroxyanthraquinone
From other anthraquinones
There are also many dihydroxy derivatives of other anthraquinones, such as 1,2-anthraquinone, 1,4-anthraquinone, and 2,6-anthraquinone.See also
- 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...
- HydroxybenzoquinoneHydroxybenzoquinoneA hydroxybenzoquinone is any of several organic compounds with formula , which can be viewed as derivatives of a benzoquinone through replacement of one hydrogen atom by an hydroxyl group ....
- 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 ....
- TrihydroxyanthraquinoneTrihydroxyanthraquinoneA trihydroxyanthraquinone or trihydroxyanthracenedione is any of several isomeric organic compounds with formula , formally derived from anthraquinone by replacing three hydrogen atoms by hydroxyl groups. They include several historically important dyes...
- TetrahydroxyanthraquinoneTetrahydroxyanthraquinoneA tetrahydroxyanthraquinone, also called tetrahydroxyanthradione, is any of several isomeric organic compounds with formula , almost invariably derived from 9,10-anthraquinone by replacing four hydrogen atoms by hydroxyl groups. Only a few of these isomers are commercially significant...
- Pentahydroxyanthraquinone
- Hexahydroxyanthraquinone
- Heptahydroxyanthraquinone
- OctahydroxyanthraquinoneOctahydroxyanthraquinoneOctahydroxyanthraquinone is an organic compound with formula , formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups....