Quinalizarin

Quinalizarin or 1,2,5,8-tetrahydroxyanthraquinone is an organic compound with formula C
₁₄H
₈O
₆. It is one of many tetrahydroxyanthraquinone isomers, formally derived from anthraquinone by replacement of four hydrogen atoms by hydroxyl (OH) groups.

Quinalizarin

Names
IUPAC name 1,2,5,8-Tetrahydroxyanthracene-9,10-dione
Identifiers
CAS Number	81-61-8
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL29898
ChemSpider	4829
ECHA InfoCard	100.001.243
PubChem CID	5004
UNII	6D43C3LYSG
CompTox Dashboard (EPA)	DTXSID4052558
InChI InChI=1S/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H Key: VBHKTXLEJZIDJF-UHFFFAOYSA-N InChI=1/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H Key: VBHKTXLEJZIDJF-UHFFFAOYAM
SMILES C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O
Properties
Chemical formula	C14H8O6
Molar mass	272.212 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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Infobox references

Quinalizarin is an inhibitor of the enzyme protein kinase CK2. It is more potent and selective than emodin.[1] It is also a potent catechol O-methyltransferase (COMT) inhibitor.[2][3]

See also

• 1,4-Dihydroxyanthraquinone (quinizarin)
• Alizarin, a related simpler dye

References

1. Cozza, G.; Mazzorana, M.; Papinutto, E.; Bain, J.; Elliott, M.; di Maira, G.; Gianoncelli, A.; Pagano, M. A.; Sarno, S.; Ruzzene, M.; Battistutta, R.; Meggio, F.; Moro, S.; Zagotto, G.; Pinna, L. A. (2009). "Quinalizarin as a Potent, Selective and Cell-Permeable Inhibitor of Protein Kinase CK2" (PDF). The Biochemical Journal. 421 (3): 387–395. doi:10.1042/BJ20090069. PMID 19432557.
2. Schneider J, Huh MM, Bradlow HL, Fishman J (April 1984). "Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells". J. Biol. Chem. 259 (8): 4840–5. PMID 6325410.
3. Schütze N, Vollmer G, Knuppen R (April 1994). "Catecholestrogens are agonists of estrogen receptor dependent gene expression in MCF-7 cells". J. Steroid Biochem. Mol. Biol. 48 (5–6): 453–61. doi:10.1016/0960-0760(94)90193-7. PMID 8180106.