Xanthotoxol

HCID 65090

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

Xanthotoxol2009-24-78-HydroxypsoralenPsoralen, 8-hydroxy-7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-9-hydroxyfuro[3,2-g]chromen-7-one8-Hydroxyfuranocoumarin9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one8RL486L8A5NSC-401269
Show more names
9-hydroxy-NSC 401269AKOS 210-08Xanthotoxol-RMXanthotoxol(AS)Xanthotoxol?, BRXanthotoxol (6CI)8-hydroxypsoralene
CHEBI:15709DTXSID501739109-hydroxy-2H-furo[3,2-g]chromen-2-one9-hydroxyfuro(3,2-g)chromen-7-one9-hydroxy-2H-furo(3,2-g)chromen-2-oneRefChem:195184DTXCID8096401217-923-1

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

Experimental & physicochemical properties

Melting Point251 - 252 °C
Physical DescriptionSolid

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk
WGK 3
ridadr
2810
hs_code
29329990
risk_code
25
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 3 items

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.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

Additional notes

DefinitionChEBI: Xanthotoxol is an 8-hydroxyfurocoumarin.

Related reactions

1 records

Compound notes

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