7,8-dihydroxy-2-phenyl-4H-chromen-4-one

• ChemBase ID: 154718
• Molecular Formular: C15H10O4
• Molecular Mass: 254.2375
• Monoisotopic Mass: 254.0579088
• SMILES: c1ccc(cc1)c1cc(=O)c2ccc(c(c2o1)O)O
• Canonical SMILES: Oc1ccc2c(c1O)oc(cc2=O)c1ccccc1
• InChI: InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
• InChIKey: COCYGNDCWFKTMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,8-dihydroxy-2-phenyl-4H-chromen-4-one
• IUPAC Traditional name: 7,8-dihydroxy-2-phenylchromen-4-one
• Synonyms: 7,8-Dihydroxyflavone hydrate; 7,8-二羟基黄酮水合物

Database IDs

• CAS Number: 38183-03-8; 38183-03-8(anhydrous)
• EC Number: 253-812-4
• MDL Number: MFCD00006836
• PubChem SID: 162248856
• PubChem CID: 1880

CALCULATED PROPERTIES

• Acid pKa: 6.730162
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.335609
• LogD (pH = 7.4): 1.6213844
• Log P: 2.3602545
• Molar Refractivity: 70.933 cm^3
• Polarizability: 26.481133 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble24 mg/mL
• Apperance: solid
• Melting Point: 250-252°C

Safety Information

• Storage Condition: desiccated
• RTECS: DJ3004000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 97%
• Empirical Formula (Hill Notation): C15H10O4 · xH2O

DETAILS

Sigma Aldrich - D5446

Biochem/physiol Actions
7,8-Dihydroxyflavone is a selective tyrosine kinase receptor B (TrkB) receptor agonist. It manifests all the therapeutic effects of brain-derived neurotrophic factor (BDNF)-such as protecting neurons from apoptosis, inhibiting kainic acid-induced toxicity, decreasing infarct volumes in stroke, and neuroprotecting in an animal model of Parkinson′s disease-without the poor pharmacokinetic profile of BDNF limiting its therapeutic potential.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D5446.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.