7,8-Dihydroxy-2-phenyl-4-benzopyron
7,8-DHF · 7,8-Dihydroxyflavone hydrate · 7,8-dihydroxyflavone (7,8-DHF) · 7,8-dihydroxy-2-phenyl-4-benzopyrone · 7,8-DIHYDROXY · 7,8-Di-OH flavone · 8-Dihydroxyflavone · TIMTEC-BB SBB000930
Identifikatoren & physikalische Daten
| CAS No. | 38183-03-8 |
|---|---|
| Summenformel | C15H10O4 |
| Durchschnittliche Molmasse | 254,24 g/mol |
| Monoisotopische Masse | 254,0579088 g/mol |
| SMILES | O=c1cc(-c2ccccc2)oc2c(O)c(O)ccc12 |
| InChIKey | COCYGNDCWFKTMF-UHFFFAOYSA-N |
| PubChem CID | 1880 |
| ChEMBL | CHEMBL75267 |
| ChEBI | CHEBI:140464 |
| EC No. | 253-812-4 |
| DTXSID | DTXSID00191568 |
| Lokaler Name | 7,8-Dihydroxy-2-phenyl-4-benzopyron |
Chemische & physikalische Eigenschaften
| XLogP | 3,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 384 |
| Lipide | Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211] |
| Löslichkeit | Very slightly solubleVery slightly soluble (in ethanol)DMSO: soluble24mg/mL |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Physical Description | Pale yellow powderBland aroma |
| Collision Cross Section | 173.79 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]152 Ų [M+H]+ [CCS Type: TW |
| Schmelzpunkt | 243-246°C |
| Siedepunkt | 494.4±45.0 °C(Predicted) |
| Dichte | 1.443±0.06 g/cm3(Predicted) |
| FEMA | 4830 | 7,8-DIHYDROXYFLAVONE |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 6.86±0.40(Predicted) |
| Farbe | Yellow or tan |
| JECFA Number | 2259 |
| Stabilität | Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 week. |
| 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 |
| SMILES | C1(C2=CC=CC=C2)OC2=C(O)C(O)=CC=C2C(=O)C=1 |
| LogP (Verteilungskoeffizient) | 2.760 (est) |
| CAS Datenbank | 38183-03-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2932990090 |
| RTECS-Nr. | DJ3004000 |
| R-Sätze (R) | 22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
7,8-Dihydroxyflavone(7,8-DHF) is a naturally occurring flavone found in the tree Godmania aesculifolia. It is a selective tyrosine kinase receptor B(TrkB) agonist that has neurotrophic effects in various neurological diseases such as stroke and Parkinson's disease. 7,8-Dihydroxyflavone binds to the TrkB receptors in a similar way to BDNF, or brain derived neurotrophic factor. When the TrkB receptor is activated, neuroprotective and neurogenetive effects occur in neurons, which tend to affect the dendrites. Dendrites are what reach out from the neurons into the synapse to participate in signaling with other neurons. 7,8-DHF has been shown to promote the growth of these dendrites, and to help restore communication between neurons in animal models.
Verwenden
7,8-Dihydroxyflavone is disubstituted flavone that acts as a small-molecule TrkB agonist. 7,8-Dihydroxyflavone has been shown to reverse memory deficits and BACE1 elevation in a mouse model of Alzheimer''s disease. 7,8-Dihydroxyflavone may also provide a therapeutic option in the treatment of other neorological disorders such as Rett syndrome and PTSD. It has recently been shown to counteract the inhibition of NMDA receptor caused by lead poisoning and confer protective effects in live rats.