| Identification | Back Directory | [Name]
XANTHOTOXOL | [CAS]
2009-24-7 | [Synonyms]
9-hydroxy-
NSC 401269
AKOS 210-08
XANTHOTOXOL
8-HYDROXYPSORALEN
8-hydroxypsoralene
XANTHOTOXOL(RG)(CALL)
9-hydroxyfuro[3,2-g]chromen-7-one
Xanthotoxol, froM CnidiuM Monnieri
2-g)(1)benzopyran-7-one,9-hydroxy-7h-furo(
9-hydroxy-7h-furo(3,2-g)(1)benzopyran-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-
6,7-Dihydroxy-5-benzofuranacrylic Acid δ-Lactone
6,7-dihydroxy-5-benzofuranacrylicacigamma-lactone
3-(6,7-Dihydroxy-5-benzofuranyl)-2-propenoic Acid δ-Lactone | [EINECS(EC#)]
217-923-1 | [Molecular Formula]
C11H6O4 | [MDL Number]
MFCD00017408 | [MOL File]
2009-24-7.mol | [Molecular Weight]
202.16 |
| Chemical Properties | Back Directory | [Melting point ]
250°C | [Boiling point ]
428.1±45.0 °C(Predicted) | [density ]
1.526±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
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 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
Dark Brown Solid | [Usage]
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. | [Description]
Xanthotoxol is a coumarin and a major component in C. monnieri that has diverse biological activities.1,2,3,4,5 It inhibits proliferation of HeLa and HepG2 cells in vitro (IC50s = 23.59 and 15.57 μM, respectively).1 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).2 It is nematocidal against M. incognita (IC50 = 68 mg/L).3 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.4 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.5 | [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.
| [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 |
| Safety Data | Back Directory | [Risk Statements ]
25 | [Safety Statements ]
20-45 | [RIDADR ]
2810 | [WGK Germany ]
WGK 3 | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Sens. 1 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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