1,2,5,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 6263
• Molecular Formular: C14H8O6
• Molecular Mass: 272.20972
• Monoisotopic Mass: 272.03208798
• SMILES: O=C1c2c(O)ccc(O)c2C(=O)c2c1ccc(O)c2O
• Canonical SMILES: Oc1c(O)ccc2c1C(=O)c1c(C2=O)c(O)ccc1O
• 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
• InChIKey: VBHKTXLEJZIDJF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,5,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: quinalizarin
• Synonyms: 1,2,5,8-tetrahydroxyanthracene-9,10-dione; 1,2,5,8-Tetrahydroxy-9,10-anthraquinone; 1,2,5,8-Tetrahydroxyanthraquinone; Alizarin Bordeaux BD; Alizarinbordeaux; Alizarine Bordeaux B; Alizarine Bordeaux; C.I. 58500; C.I. Mordant Violet 26; Khinalizarin; NSC 144046; NSC 4896; PHF 016; Quinalizarin

Database IDs

• CAS Number: 81-61-8
• EC Number: 201-366-6
• MDL Number: MFCD00001205
• Beilstein Number: 1889617
• PubChem SID: 99445131; 160969688
• PubChem CID: 5004
• Color Index Number: 58500

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.495825
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 3.6501162
• LogD (pH = 7.4): 3.400362
• Log P: 3.6544447
• Molar Refractivity: 69.0746 cm^3
• Polarizability: 25.811943 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -2.7
• Solubility (Water): 5.49e-01 g/l

PROPERTIES

Physical Property

• Apperance: red powder
• Melting Point: ≥300 °C

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50
• Safety Statements: 61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Storage Temperature: room temp

Product Information

• Purity: ≥95% (HPLC)
• Description: Tautomers
• Empirical Formula (Hill Notation): C14H8O6
• Classification: Rare Derivatives of Natural Compounds

DETAILS

DrugBank - DB08660

Drug information: experimental

Sigma Aldrich - Q2763

Biochem/physiol Actions
Quinalizarin is a potent (IC50 = 110 nM), ATP-competitive, and highly selective (IC50 >1μM against CK1 and 72 other kinases) casein Kinase II (CK2) inhibitor.