Rufigallol

Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula C
₁₄O
₈H
₈. It one of several hydroxyanthraquinones. It occurs naturally being derived from gallic acid.

Quick facts Names, Identifiers ...

Rufigallol

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
CAS Number	82-12-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:37500 N
ChemSpider	59160 N
PubChem CID	65737
UNII	S977046N6I Y
CompTox Dashboard (EPA)	DTXSID1075359
InChI 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 N Key: NEIMTOOWBACOHT-UHFFFAOYSA-N N 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
SMILES C1=C2C(=C(C(=C1O)O)O)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
Properties
Chemical formula	C14H8O8
Molar mass	304.210 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa). N verify (what is YN ?) Infobox references

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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]