Basic information
- CAS
2009-24-7- Standard SMILES
O=c1ccc2cc3ccoc3c(O)c2o1- InChIKey
JWVYQQGERKEAHW-UHFFFAOYSA-N- Molecular formula
- C11H6O4
- Average molar mass
- 202.16 g/mol
- Monoisotopic mass
- 202.02660867
Overview
Xanthotoxol is an 8-hydroxyfurocoumarin.
Names & identifiers
- Preferred name
- Xanthotoxol
- IUPAC
- 9-hydroxyfuro[3,2-g]chromen-7-one
- English name
- XANTHOTOXOL
- Molecular formula
- C11H6O4
- Molecular weight
- 202.16
Names & synonyms
Show more names
Database identifiers
- CAS
2009-24-7- PubChem CID
- 65090
- DTXSID
DTXSID50173910- ChEMBL
CHEMBL1192- ChEBI
CHEBI:15709- UNII
- 8RL486L8A5
- EC Number
- 217-923-1
- Nikkaji
- J7.847F
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 59.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 312
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 250 °C · 250°C
- Boiling point
- 428.1 · 428.1±45.0 °C(Predicted)
- Density
- 1.526 · 1.526±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 5.74 · 5.74±0.20(Predicted)
- color
- 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)
- FDA UNII
- 8 RL486L8A5 · 8RL486L8A5
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
- Risk Statements
- 25 · 25
- Safety Statements
- 20 · 20-45-24/25
- RIDADR
- 2810 · 2810
- WGK Germany
- 3 · WGK 3
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralSkin · Acute Tox. 4 OralSkin Sens. 1
Safety & regulation
GHS classification
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.
Hazard information
Safety data
- wgk
- WGK 3
- ridadr
- 2810
- hs_code
- 29329990
- risk_code
- 25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 20-45-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Hazard Classifications
- Acute Tox. 4 OralSkin Sens. 1
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
Applications
DescriptionXanthotoxol 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.
UsesXanthotoxol 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.
UsesA 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 shown 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 studies show that it may also have antioxidant and anticancer activities.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: Xanthotoxol is an 8-hydroxyfurocoumarin.
Related reactions
Compound notes
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