5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one hydrate

• ChemBase ID: 154114
• Molecular Formular: C16H14O6
• Molecular Mass: 302.27876
• Monoisotopic Mass: 302.07903817
• SMILES: COc1c(cc(c2c1oc(cc2=O)c1ccccc1)O)O.O
• Canonical SMILES: COc1c(O)cc(c2c1oc(cc2=O)c1ccccc1)O.O
• InChI: InChI=1S/C16H12O5.H2O/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9;/h2-8,17,19H,1H3;1H2
• InChIKey: XLCSETHCROERAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one hydrate
• IUPAC Traditional name: wogonin hydrate
• Synonyms: 5,7-Dihydroxy-8-methoxyflavone; Wogonin hydrate

Database IDs

• CAS Number: 632-85-9(anhydrous)
• MDL Number: MFCD12828871
• PubChem SID: 162248253
• PubChem CID: 71311794

CALCULATED PROPERTIES

• Acid pKa: 7.159617
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.8432517
• LogD (pH = 7.4): 2.419946
• Log P: 2.8525832
• Molar Refractivity: 77.3962 cm^3
• Polarizability: 29.0158 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: solid

Safety Information

• RTECS: LK8331000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H12O5 · xH2O

DETAILS

Sigma Aldrich - W0769

Biochem/physiol Actions
Wogonin is an anti-inflammatory agent and COX-2 inhibitor, which inhibits the induction of both iNOS and COX-2. Wogonin inhibits COX-2 (IC50 = 46 μM) without affecting COX-1. Wogonin inhibits iNOS induction and thus inhibts activation-induced C6 glial cell death. Specifically, Wogonin inhibits NF-kappaB-mediated iNOS induction.