5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one

• ChemBase ID: 128748
• Molecular Formular: C16H12O5
• Molecular Mass: 284.26348
• Monoisotopic Mass: 284.06847348
• SMILES: COc1c(cc2c(c1O)c(=O)cc(o2)c1ccccc1)O
• Canonical SMILES: COc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccccc1
• InChI: InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3
• InChIKey: LKOJGSWUMISDOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one
• IUPAC Traditional name: oroxylin A
• Synonyms: Oroxylin A; 5,7-Dihydroxy-6-methoxy-2-phenyl-4H-1-benzopyran-4-one; 5,7-Dihydroxy-6-methoxyflavone;; 6-Methoxybaicalein;; Oroxylin A

Database IDs

• CAS Number: 480-11-5
• MDL Number: MFCD02259441
• PubChem SID: 162223054
• PubChem CID: 5320315
• Wikipedia Title: Oroxylin_A

CALCULATED PROPERTIES

• Acid pKa: 7.1012836
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.8419216
• LogD (pH = 7.4): 2.3691308
• Log P: 2.8525832
• Molar Refractivity: 77.3962 cm^3
• Polarizability: 29.01575 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: yellow powder; Yellow powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 98.5
• Empirical Formula (Hill Notation): C16H12O5

DETAILS

Sigma Aldrich - O0641

Biochem/physiol Actions
Oroxylin A is a flavonoid isolated from Scutellaria baicalensis, which is one of the most important medicinal herbs in traditional Korean/Chinese/Japanese medicine. The amelioration of Abeta(25-35) peptide-induced memory impairment by oroxylin A is believed to be mediated via the GABAergic neurotransmitter system after a single administration, or by reductions in Abeta(25-35) peptide-induced astrocyte and microglia activations, iNOS expression, lipid peroxidation, and increased cholinergic neurotransmission after subchronic administration.