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Xanthotoxol

$185

  • Brand : BIOFRON

  • Catalogue Number : BF-X1001

  • Specification : 98%

  • CAS number : 2009-24-7

  • Formula : C11H6O4

  • Molecular Weight : 202.16

  • PUBCHEM ID : 65090

  • Volume : 20mg

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Catalogue Number

BF-X1001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

202.16

Appearance

White crystal

Botanical Source

Changium smyrnioides,Glehnia littoralis,Angelica dahurica,Citrus aurantium,Paliurus ramosissimus

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O

Synonyms

9-hydroxyfuro[3,2-g]chromen-7-one/8-Hydroxypsoralen/T C566 DO LVOJ BQ/8-Hydroxy-4':5',6:7-furocoumarin/7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-/9-Hydroxy-7H-furo[3,2-g]chromen-7-one/Xanthotoxol

IUPAC Name

9-hydroxyfuro[3,2-g]chromen-7-one

Applications

Xanthotoxol is a biologically active linear furocoumarin, shows strong pharmacological activities as anti-inflammatory, antioxidant, 5-HT antagonistic, and neuroprotective effects.

Density

1.5±0.1 g/cm3

Solubility

Methanol; DMF

Flash Point

212.7±28.7 °C

Boiling Point

428.1±45.0 °C at 760 mmHg

Melting Point

250ºC

InChl

InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

InChl Key

JWVYQQGERKEAHW-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:2009-24-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27034690

Abstract

Cytochrome p450 (CYP450) enzymes are predominantly involved in Phase I metabolism of xenobiotics. In this study, the CYP450 isoforms involved in xanthotoxol metabolism were identified using recombinant CYP450s. In addition, the inhibitory effects of xanthotoxol on eight CYP450 isoforms and its pharmacokinetic parameters were determined using human liver microsomes. CYP1A2, one of CYP450s, played a key role in the metabolism of xanthotoxol compared to other CYP450s. Xanthotoxol showed stronger inhibition on CYP3A4 and CYP1A2 compared to other isoenzymes with the IC50 of 7.43 μM for CYP3A4 and 27.82 μM for CYP1A2. The values of inhibition kinetic parameters (Ki) were 21.15 μM and 2.22 μM for CYP1A2 and CYP3A4, respectively. The metabolism of xanthotoxol obeyed the typical monophasic Michaelis-Menten kinetics and V max, K m , and CLint values were calculated as 0.55 nmol·min(-1)·mg(-1), 8.46 μM, and 0.06 mL·min(-1)·mg(-1). In addition, the results of molecular docking showed that xanthotoxol was bound to CYP1A2 with hydrophobic and π-π bond and CYP3A4 with hydrogen and hydrophobic bond. We predicted the hepatic clearance (CL H ) and the CL H value was 15.91 mL·min(-1)·kg(-1) body weight. These data were significant for the application of xanthotoxol and xanthotoxol-containing herbs.

Title

Metabolism and Metabolic Inhibition of Xanthotoxol in Human Liver Microsomes

Author

Zhongnv Ma 1 , Xianbao Shi 2 , Gang Zhang 3 , Feng Guo 1 , Lina Shan 2 , Jiqun Cai 1

Publish date

2016

PMID

23619720

Abstract

We previously found that xanthotoxol, one of the major active ingredients in Cnidium monnieri (L.) Cusson, exerts protective effects in a rat model of focal cerebral ischemia/reperfusion injury by alleviating brain edema, inhibiting the neutrophil infiltration, and decreasing the expression of intercellular adhesion molecule-1 (ICAM-1) and E-selectin. The present study was designed to further determine the possible mechanisms of action of neuroprotective properties of xanthotoxol after cerebral ischemia. Transient focal cerebral ischemia/reperfusion model in male Sprague-Dawley rats was induced by 2-h middle cerebral artery occlusion followed by 24-h reperfusion. Xanthotoxol (5 and 10 mg/kg) or vehicle were administered intraperitoneally at 1 and 12 h after the onset of ischemia. At 24 h after reperfusion, we assessed the effect of xanthotoxol on the blood-brain barrier (BBB) permeability, the production of pro-inflammatory mediators such as interleukin (IL)-1β, tumor necrosis factor (TNF)-α, IL-8, nitric oxide (NO), inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and the p65 subunit of the transcription factor, nuclear factor-κB (NF-κB) in the cortex after ischemic insult. The results showed that xanthotoxol treatment significantly attenuated BBB disruption, reduced the IL-1β, TNF-α, IL-8 and NO level, and attenuated the iNOS activity compared with vehicle-treated animals. Further, xanthotoxol treatment also significantly prevented the ischemia/reperfusion-induced increase in the protein expression of iNOS, COX-2, and the nuclear NF-κB p65. These results, taken together with those of our previous study, suggest that the neuroprotection may be attributed to the ability of xanthotoxol to attenuate the expression of pro-inflammatory mediators and thereby inhibit the inflammatory response after cerebral ischemia.

Title

Xanthotoxol Exerts Neuroprotective Effects via Suppression of the Inflammatory Response in a Rat Model of Focal Cerebral Ischemia

Author

Wei He 1 , Weiwei Chen, Yumei Zhou, Yuantong Tian, Fang Liao

Publish date

2013 Jul

PMID

24342512

Abstract

The objective of the present study was to develop a new method for the simultaneous quantitation of imperatorin and its metabolite xanthotoxol in rat plasma. The samples were prepared with hollow fiber liquid phase microextraction (HF-LPME). The optimized extraction procedure was acquired by assessing extraction solvent, length of the fiber, agitation rate, extraction temperature and time. A comparison of sample pretreatment ways between HF-LPME and deproteinization with methanol was performed, which demonstrated less ion suppression and better sensitivity of HF-LPME. Analytes were separated on a C18 column with a gradient elution consisted of methanol and water containing 1mmol/L ammonium acetate. The detection was accomplished by electrospray ionization (ESI) source operating in the positive ionization mode. Selected-multiple-reaction monitoring (SMRM) scanning was employed, which guaranteed a higher sensitivity compared with MRM mode. Calibration curves were linear over investigated ranges with correlation coefficients greater than 0.9979. Precision varied from 0.26% to 14%, and the accuracy varied within ±5.5%. The developed method was successfully applied to the pharmacokinetic research of imperatorin and its metabolite xanthotoxol after oral administration of imperatorin to rats.

KEYWORDS

HPLC-ESI-MS; Hollow fiber liquid phase microextraction; Imperatorin; Pharmacokinetics; Xanthotoxol.

Title

Simultaneous Determination of Imperatorin and Its Metabolite Xanthotoxol in Rat Plasma by Using HPLC-ESI-MS Coupled With Hollow Fiber Liquid Phase Microextraction

Author

Juan Zhang 1 , Min Zhang 2 , Shan Fu 1 , Tao Li 1 , Shuang Wang 1 , Minmin Zhao 1 , Weijing Ding 1 , Chunying Wang 1 , Qiao Wang 3

Publish date

2014 Jan 1