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

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 ...

with formula . It one of several

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 ...

s. It occurs naturally being derived from

gallic acid Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plant ...

. The compound is soluble in

dioxane Dioxane may refer to the following chemical compounds: * 1,2-dioxane * 1,3-dioxane * 1,4-dioxane {{Authority control ...

, from which it crystallizes as red needles that sublime without melting at 365 °C. It can be obtained by treating

with concentrated

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

and then with

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

. It is prepared by acid-catalyzed condensation of a pair of

molecules. Rufigallol is particularly toxic to the

malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...

l parasite ''

Plasmodium falciparum ''Plasmodium falciparum'' is a Unicellular organism, unicellular protozoan parasite of humans and is the deadliest species of ''Plasmodium'' that causes malaria in humans. The parasite is transmitted through the bite of a female ''Anopheles'' mos ...

'' and has a

synergistic Synergy is an interaction or cooperation giving rise to a whole that is greater than the simple sum of its parts (i.e., a non-linear addition of force, energy, or effect). The term ''synergy'' comes from the Attic Greek word συνεργία ' f ...

effect in combination with the

antimalarial Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young ...

drug exifone, which has structural similarities to rufigallol.R. W. Winter, Kenneth A. Cornell, Linda L. Johnson, Marina Ignatushchenko, David J. Hinrichs, Michael K. Riscoe (1996), ''Potentiation of The Antimalarial Agent Rufigallol''. Antimicrobial Agents and Chemotherapy, Vol. 40, No. 6, Pages 1408–14
Online version
accessed on 2010-02-01. Rufigallol forms a crimson-colored complex with

beryllium Beryllium is a chemical element; it has Symbol (chemistry), symbol Be and atomic number 4. It is a steel-gray, hard, strong, lightweight and brittle alkaline earth metal. It is a divalent element that occurs naturally only in combination with ...

aluminium Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...

thorium Thorium is a chemical element; it has symbol Th and atomic number 90. Thorium is a weakly radioactive light silver metal which tarnishes olive grey when it is exposed to air, forming thorium dioxide; it is moderately soft, malleable, and ha ...

zirconium Zirconium is a chemical element; it has Symbol (chemistry), symbol Zr and atomic number 40. First identified in 1789, isolated in impure form in 1824, and manufactured at scale by 1925, pure zirconium is a lustrous transition metal with a greyis ...

and

hafnium Hafnium is a chemical element; it has symbol Hf and atomic number 72. A lustrous, silvery gray, tetravalent transition metal, hafnium chemically resembles zirconium and is found in many zirconium minerals. Its existence was predicted by Dm ...

, and this reaction has been used for the

spot Spot or SPOT may refer to: Places * Spot, North Carolina, a community in the United States * The Spot, New South Wales, a locality in Sydney, Australia * South Pole Traverse, sometimes called the South Pole Overland Traverse People * Spot Coll ...

and

spectrophotometric Spectrophotometry is a branch of electromagnetic spectroscopy concerned with the quantitative measurement of the reflection or transmission properties of a material as a function of wavelength. Spectrophotometry uses photometers, known as spe ...

determination of beryllium in low concentrations.M. A. Azim and A. A. Ayaz (1969), ''Spectrophotometric determination of beryllium''. Microchimica Acta Volume 57, Number 1, pages 153-159

References

{{reflist Pyrogallols Hydroxyanthraquinones 3-Hydroxypropenals

See also

References