Rufigallol

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Rufigallol
Rufigallol.png
Rufigallol-3D-balls.png
Names
Preferred IUPAC name
1,2,3,5,6,7-Hexahydroxyanthracene-9,10-dione
Other names
Rufigallic acid; 1,2,3,5,6,7-Hexahydroxy-9,10-anthraquinone; 1,2,3,5,6,7-Hexahydroxyanthracene-9,10-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C14H8O8/c15-5-1-3-7(13(21)11(5)19)10(18)4-2-6(16)12(20)14(22)8(4)9(3)17/h1-2,15-16,19-22H X mark.svgN
    Key: NEIMTOOWBACOHT-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C14H8O8/c15-5-1-3-7(13(21)11(5)19)10(18)4-2-6(16)12(20)14(22)8(4)9(3)17/h1-2,15-16,19-22H
    Key: NEIMTOOWBACOHT-UHFFFAOYAS
  • C1=C2C(=C(C(=C1O)O)O)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
Properties
C14H8O8
Molar mass 304.210 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula C
14
O
8
H
8
. It one of several hydroxyanthraquinones. It occurs naturally being derived from gallic acid.

The compound is soluble in dioxane, from which it crystallizes as red needles that sublime without melting at 365 °C. [1] It can be obtained by treating gallic acid with concentrated sulfuric acid and then with sodium hydroxide. [1] It is prepared by acid-catalyzed condensation of a pair of gallic acid molecules. [2]

Rufigallol is particularly toxic to the malarial parasite Plasmodium falciparum and has a synergistic effect in combination with the antimalarial drug exifone, which has structural similarities to rufigallol. [3]

Rufigallol forms a crimson-colored complex with beryllium, aluminium, thorium, zirconium and hafnium, and this reaction has been used for the spot and spectrophotometric determination of beryllium in low concentrations. [1]

See also

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Beryllium is a chemical element; it has 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 other elements to form minerals. Gemstones high in beryllium include beryl and chrysoberyl. It is a relatively rare element in the universe, usually occurring as a product of the spallation of larger atomic nuclei that have collided with cosmic rays. Within the cores of stars, beryllium is depleted as it is fused into heavier elements. Beryllium constitutes about 0.0004 percent by mass of Earth's crust. The world's annual beryllium production of 220 tons is usually manufactured by extraction from the mineral beryl, a difficult process because beryllium bonds strongly to oxygen.

<span class="mw-page-title-main">Alkaline earth metal</span> Group of chemical elements

The alkaline earth metals are six chemical elements in group 2 of the periodic table. They are beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra). The elements have very similar properties: they are all shiny, silvery-white, somewhat reactive metals at standard temperature and pressure.

A period 2 element is one of the chemical elements in the second row of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of the elements as their atomic number increases; a new row is started when chemical behavior begins to repeat, creating columns of elements with similar properties.

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<span class="mw-page-title-main">Salicylaldoxime</span> Chemical compound

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<span class="mw-page-title-main">Cacodylic acid</span> Chemical compound

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Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

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<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the organic derivativess of any group 2 element. It is a subtheme to main group organometallic chemistry. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organometallic group 2 compounds are typically limited to academic interests.

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<span class="mw-page-title-main">Octahydroxyanthraquinone</span> Chemical compound

Octahydroxyanthraquinone is an organic compound with formula C
14
H
8
O
10
, formally derived from anthraquinone by replacement of 8 hydrogen atoms by hydroxyl groups.

A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

<span class="mw-page-title-main">Ellagitannin</span> Diverse class of hydrolyzable tannins, a type of polyphenol

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

<span class="mw-page-title-main">Hydroxyanthraquinone</span> Class of chemical compounds

In organic chemistry hydroxyanthraquinones refers to compounds with the formula C12H8-n(OH)n(CO)2 where n ≥ 1. Almost all hydroxyanthraquinones are derivative of 9,10-anthraquinone.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Bromopyrogallol red</span> Chemical compound

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<span class="mw-page-title-main">Violuric acid</span> Chemical compound

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References

  1. 1 2 3 M. A. Azim and A. A. Ayaz (1969), Spectrophotometric determination of beryllium. Microchimica Acta Volume 57, Number 1, pages 153-159 doi : 10.1007/BF01216677
  2. Bisoyi, Hari Krishna; Kumar, Sandeep (2007). "Microwave-assisted synthesis of rufigallol and its novel room-temperature liquid crystalline derivatives". Tetrahedron Letters. 48 (25): 4399–4402. doi:10.1016/j.tetlet.2007.04.094.
  3. 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 1408–1411Online version accessed on 2010-02-01.