4-(acetyloxy)-5-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

• ChemBase ID: 159431
• Molecular Formular: C17H10O7
• Molecular Mass: 326.2571
• Monoisotopic Mass: 326.04265266
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(cc(c1)C(=O)O)OC(=O)C)O
• Canonical SMILES: CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1O)C(=O)O
• InChI: InChI=1S/C17H10O7/c1-7(18)24-12-6-8(17(22)23)5-10-14(12)16(21)13-9(15(10)20)3-2-4-11(13)19/h2-6,19H,1H3,(H,22,23)
• InChIKey: FRIXMWPJYKVOCV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(acetyloxy)-5-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• IUPAC Traditional name: 4-(acetyloxy)-5-hydroxy-9,10-dioxoanthracene-2-carboxylic acid
• Synonyms: 4-(Acetyloxy)-9,10-dihydro-5-hydroxy-9,10-dioxo-2-anthracenecarboxylic Acid; 4-Acetyl Rhein

Database IDs

• CAS Number: 875535-36-7
• PubChem SID: 162253566
• PubChem CID: 10268224

CALCULATED PROPERTIES

• Acid pKa: 3.3734825
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.41702038
• LogD (pH = 7.4): -0.88386345
• Log P: 2.5299847
• Molar Refractivity: 81.5205 cm^3
• Polarizability: 30.776972 Å^3
• Polar Surface Area: 117.97 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A187700

An impurity in the Diacerein (D303000) bulk drug.

REFERENCES

• Pelletier, J., et al.: Arthritis Rheum., 43, 2339 (2000)
• Pelletier, J; J Rheumatol 2001, 28, 814,,,Tamura, T., et al.: Eur. J. Pharmacol., 448, 81 (2000)