Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an 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...

 with formula , which can be viewed as a derivative of 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...

 through the replacement of six 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 (H) 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 (OH).

The compound is soluble in dioxane, from which it crystallizes as red needles that sublime without melting at 365 °C. It can be obtained by treating gallic acid

Gallic acid

Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H23COOH. Gallic acid is found both free and as part of...

 with concentrated 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...

 and then with sodium hydroxide.

Rufigallol is particularly toxic to the malaria

Malaria

Malaria is a mosquito-borne infectious disease of humans and other animals caused by eukaryotic protists of the genus Plasmodium. The disease results from the multiplication of Plasmodium parasites within red blood cells, causing symptoms that typically include fever and headache, in severe cases...

l parasite Plasmodium falciparum

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...

and has a synergistic

Synergy

Synergy may be defined as two or more things functioning together to produce a result not independently obtainable.The term synergy comes from the Greek word from , , meaning "working together".-Definitions and usages:...

 effect in combination with the antimalarial drug exifone, which has structural sumilarities to rufigallol.

Rufigallol forms a crimson-colored complex with beryllium

Beryllium

Beryllium is the chemical element with the symbol Be and atomic number 4. It is a divalent element which occurs naturally only in combination with other elements in minerals. Notable gemstones which contain beryllium include beryl and chrysoberyl...

, aluminum, thorium

Thorium

Thorium is a natural radioactive chemical element with the symbol Th and atomic number 90. It was discovered in 1828 and named after Thor, the Norse god of thunder....

, zirconium

Zirconium

Zirconium is a chemical element with the symbol Zr and atomic number 40. The name of zirconium is taken from the mineral zircon. Its atomic mass is 91.224. It is a lustrous, grey-white, strong transition metal that resembles titanium...

 and hafnium

Hafnium

Hafnium is a chemical element with the symbol Hf and atomic number 72. A lustrous, silvery gray, tetravalent transition metal, hafnium chemically resembles zirconium and is found in zirconium minerals. Its existence was predicted by Dmitri Mendeleev in 1869. Hafnium was the penultimate stable...

, and this reaction has been used for the spot and spectrophotometric

Spectrophotometry

In chemistry, spectrophotometry is the quantitative measurement of the reflection or transmission properties of a material as a function of wavelength...

 determination of beryllium in low concentrations.

See also

• Quinone
  Quinone
  A quinone is a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C– groups with any necessary rearrangement of double bonds," resulting in "a fully conjugated cyclic dione structure."...
  
  
• Hydroxyanthraquinone
  Hydroxyanthraquinone
  A 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 ....
  
  
• Hexahydroxyanthraquinone
• Octahydroxyanthraquinone
  Octahydroxyanthraquinone
  Octahydroxyanthraquinone is an organic compound with formula , formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups....