XANTHOTOXOL Chemical Properties

Melting point:

250°C

Boiling point:

428.1±45.0 °C(Predicted)

Density 

1.526±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

5.74±0.20(Predicted)

color 

Light Beige to Dark Brown

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 (est)

Safety Information

Risk Statements 

25

Safety Statements 

20-45-24/25

RIDADR 

2810

HS Code 

29329990

XANTHOTOXOL Usage And Synthesis

Description

Xanthotoxol 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.

Chemical Properties

Dark Brown Solid

Uses

Xanthotoxol 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.

Uses

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 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.

Definition

ChEBI: Xanthotoxol is an 8-hydroxyfurocoumarin.

Synthesis Reference(s)

Synthetic Communications, 37, p. 361, 2007 DOI: 10.1080/00397910601038616

References

[1] YAN BAI . Coumarins from the roots of Angelica dahurica with antioxidant and antiproliferative activities[J]. Journal of Functional Foods, 2016, 20: Pages 453-462. DOI: 10.1016/j.jff.2015.11.018
[2] DONG LI  Li W. Coumarins from the roots of Angelica dahurica cause anti-allergic inflammation.[J]. Experimental and therapeutic medicine, 2017, 14 1: 874-880. DOI: 10.3892/etm.2017.4569
[3] PIERLUIGI CABONI. Nematicidal activity of furanocoumarins from parsley against Meloidogyne spp.[J]. Pest Management Science, 2014, 71 8: 1099-1105. DOI: 10.1002/ps.3890
[4] O.P. SETHI  O. D G  K K Anand. Evaluation of xanthotoxol for central nervous system activity[J]. Journal of ethnopharmacology, 1992, 36 3: Pages 239-247. DOI: 10.1016/0378-8741(92)90050-2
[5] WEI HE. Xanthotoxol exerts neuroprotective effects via suppression of the inflammatory response in a rat model of focal cerebral ischemia.[J]. Cellular and Molecular Neurobiology, 2013, 33 5: 715-722. DOI: 10.1007/s10571-013-9939-2

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