2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one

• ChemBase ID: 119066
• Molecular Formular: C11H8O5
• Molecular Mass: 220.17822
• Monoisotopic Mass: 220.03717336
• SMILES: c12c(c(c(cc2cccc(c1=O)O)O)O)O
• Canonical SMILES: Oc1cc2cccc(c(=O)c2c(c1O)O)O
• InChI: InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)
• InChIKey: WDGFFVCWBZVLCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one
• IUPAC Traditional name: purpurogallin
• Synonyms: 2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one; Purpurogallin

Database IDs

• CAS Number: 569-77-7
• EC Number: 209-324-9
• MDL Number: MFCD00004145
• PubChem SID: 162107277
• PubChem CID: 5281571

CALCULATED PROPERTIES

• Acid pKa: 6.7944193
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.914114
• LogD (pH = 7.4): 1.2369165
• Log P: 1.9367748
• Molar Refractivity: 59.0477 cm^3
• Polarizability: 20.957212 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 275 °C (dec.)(lit.)

Safety Information

• RTECS: DE8380000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Grade: Sigma Grade
• Empirical Formula (Hill Notation): C11H8O5
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - P7380

Application
Calibration standard for peroxidase assays using pyrogallol as substrate.
Biochem/physiol Actions
Polyphenol antibiotic originally isolated from Quercus nutgall that has antioxidant activity. Competitive inhibitor of epidermal growth factor receptor protein tyrosine kinase activity; inhibitor of xanthine oxidase.