Octahydroxyanthraquinone
Encyclopedia
Octahydroxyanthraquinone is an organic compound
with formula , formally derived from anthraquinone
by replacement of 8 hydrogen
atoms by hydroxyl
groups.
The compound was obtained in 1911 by Georg von Georgievics
and can be obtained through oxidation of rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) with boric acid
and mercuric oxide in sulfuric acid
at 250 °C.
Ester
s of octahydroxyanthraquinone, where all eight hydroxyls are replaced by straight-chain 1-alkanecarboxylate groups -n-COO-, with n between 6 and 14, are liquid crystal
s and have been studied for possible LCD application
s.
Octahydroxyanthraquinone is active against the malaria parasite
, but rufigallol
(1,2,3,5,6,7-hexahydroxyanthraquinone) is 22 times more potent.
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...
with formula , formally derived from 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 replacement of 8 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.
The compound was obtained in 1911 by Georg von Georgievics
Georg von Georgievics
Georg Cornelius Theodor von Georgievics was an Austria-Hungary chemist.- Biography :...
and can be obtained through oxidation of rufigallol (1,2,3,5,6,7-hexahydroxyanthraquinone) with boric acid
Boric acid
Boric acid, also called hydrogen borate or boracic acid or orthoboric acid or acidum boricum, is a weak acid of boron often used as an antiseptic, insecticide, flame retardant, as a neutron absorber, and as a precursor of other chemical compounds. It exists in the form of colorless crystals or a...
and mercuric oxide in sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
at 250 °C.
Ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
s of octahydroxyanthraquinone, where all eight hydroxyls are replaced by straight-chain 1-alkanecarboxylate groups -n-COO-, with n between 6 and 14, are liquid crystal
Liquid crystal
Liquid crystals are a state of matter that have properties between those of a conventional liquid and those of a solid crystal. For instance, an LC may flow like a liquid, but its molecules may be oriented in a crystal-like way. There are many different types of LC phases, which can be...
s and have been studied for possible LCD application
Liquid crystal display
A liquid crystal display is a flat panel display, electronic visual display, or video display that uses the light modulating properties of liquid crystals . LCs do not emit light directly....
s.
Octahydroxyanthraquinone is active against the malaria parasite
Plasmodium falciparum
Plasmodium falciparum is a protozoan parasite, one of the species of Plasmodium that cause malaria in humans. It is transmitted by the female Anopheles mosquito. Malaria caused by this species is the most dangerous form of malaria, with the highest rates of complications and mortality...
, but rufigallol
Rufigallol
Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula , which can be viewed as a derivative of anthraquinone through the replacement of six hydrogen atoms by hydroxyl groups ....
(1,2,3,5,6,7-hexahydroxyanthraquinone) is 22 times more potent.