Grundinformationen
- CAS
2009-24-7- Standard-SMILES
O=c1ccc2cc3ccoc3c(O)c2o1- InChIKey
JWVYQQGERKEAHW-UHFFFAOYSA-N- Summenformel
- C11H6O4
- Durchschnittliche Molmasse
- 202,16 g/mol
- Monoisotopische Masse
- 202,02660867
Überblick
Xanthotoxol is an 8-hydroxyfurocoumarin.
Namen und Bezeichner
- Bevorzugter Name
- Xanthotoxol
- IUPAC
- 9-hydroxyfuro[3,2-g]chromen-7-one
- Lokaler Name
- 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-on
- Englischer Name
- XANTHOTOXOL
- Summenformel
- C11H6O4
- Molmasse
- 202.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
2009-24-7- PubChem CID
- 65090
- DTXSID
DTXSID50173910- ChEMBL
CHEMBL1192- ChEBI
CHEBI:15709- UNII
- 8RL486L8A5
- EC Number
- 217-923-1
- Nikkaji
- J7.847F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 59,7 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 312
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 250 °C · 250°C
- Siedepunkt
- 428.1 · 428.1±45.0 °C(Predicted)
- Dichte
- 1.526 · 1.526±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 5.74 · 5.74±0.20(Predicted)
- Farbe
- Light Beige to Dark Brown
- Major Application
- food and beverages
- InChI
- InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
- InChIKey
- JWVYQQGERKEAHW-UHFFFAOYSA-N
- SMILES
- C1(=O)OC2=C(O)C3OC=CC=3C=C2C=C1
- LogP
- 1.405 · 1.405 (est)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- WGK 3
- ridadr
- 2810
- hs_code
- 29329990
- risk_code
- 25
- safety_code
- 20-45-24/25
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralSkin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
Anwendungen
BeschreibungXanthotoxol is a coumarin and a major component in C. monnieri that has diverse biological activities. It inhibits proliferation of HeLa and HepG2 cells in vitro (IC50s = 23.59 and 15.57 μM, respectively). Xanthotoxol increases histamine release from mast cells and decreases secretion of TNF-α, IL-4, and IL-1β from RBL-2H3 cells induced by DNP-human serum albumin (DNP-HSA). It is nematocidal against M. incognita (IC50 = 68 mg/L). In vivo, xanthotoxol inhibits predatory mouse and rat killing behavior in dogs and cats when administered at doses ranging from 3 to 100 mg/kg and 5 to 20 mg/kg, respectively. It reduces amphetamine-induced hypermobility in mice and hamsters. Xanthotoxol (5 and 10 mg/kg) reduces brain edema, neutrophil infiltration, blood-brain barrier disruption, production of IL-1β, TNF-α, IL-8, and nitric oxide (NO), and levels of intercellular adhesion molecule-1 (ICAM-1) and E-selectin in a rat model of focal cerebral ischemia.
VerwendenXanthotoxol is a hydroxylated psoralen that inhibits neutrophil infiltration and brain edema induced by focal cerebral ischemia-reperfusion injury in rats. A potentially useful antiarrhythmic agent. It has been show n to be effective in the prevention of ventricular fibrillation of mice induced by chloroform, of rats induced by calcium chloride, and in treatment of rat arrhythmia induced by aconitine. Recent stud ies show that it may also have antioxidant and anticancer activities.
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