2009-24-7

Basic information

• Product Name: XANTHOTOXOL
• Synonyms: 2-g)(1)benzopyran-7-one,9-hydroxy-7h-furo(;6,7-dihydroxy-5-benzofuranacrylicacigamma-lactone;8-hydroxypsoralene;9-hydroxy-7h-furo(3,2-g)(1)benzopyran-7-one;8-HYDROXYPSORALEN;AKOS 210-08;XANTHOTOXOL;7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-
• CAS NO: 2009-24-7
• Molecular Formula: C₁₁H₆O₄
• Molecular Weight: 202.16
• EINECS: 217-923-1
• Product Categories: Coumarins;API intermediates;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 2009-24-7.mol
• Article Data: 40

Chemical Properties

• Melting Point: 250°C
• Boiling Point: 428.1 °C at 760 mmHg
• Flash Point: 212.7 °C
• Appearance: /
• Density: 1.526 g/cm³
• Vapor Pressure: 6.22E-08mmHg at 25°C
• Refractive Index: 1.71
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.74±0.20(Predicted)
• CAS DataBase Reference: XANTHOTOXOL(CAS DataBase Reference)
• NIST Chemistry Reference: XANTHOTOXOL(2009-24-7)
• EPA Substance Registry System: XANTHOTOXOL(2009-24-7)

Safety Data

• Statements: 25
• Safety Statements: 20-45-24/25
• RIDADR: 2810
• Hazardous Substances Data: 2009-24-7(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 2009-24-7 differently. You can refer to the following data:
1. 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.
2. 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.

Synthesis Reference(s)

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

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

Upstream product

• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 86290-70-2 9-acetyl-7H-furo[3,2-g]chromen-7-one 
• 72939-36-7 8-Acetyl-7-(allyloxy)coumarin 
• 86290-56-4 8-acetyl-6-allyl-7-hydroxycoumarin 
• 71612-25-4 8-geranyloxypsoralen 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 143390-87-8 6',7'-Epoxy-8-geranyloxypsoralen 
• 87838-97-9 indicolactone 
• 87838-97-9 wampetin 
• 99663-29-3 xanthotoxol 8-O-β-D-glucopyranoside 
• 482-44-0 imperatorin 
• 10387-49-2 7-acetyloxycoumarin 

Downstream Products

• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 482-44-0 imperatorin 
• 10386-19-3 O-acetylxanthotoxol 
• 42207-40-9 9-(phenylmethoxy)-7H-furo[3,2-g][1]benzopyran-7-one 
• 83934-65-0 8-ethoxypsoralen 
• 85213-86-1 8-(6'-bromohexyloxy)psoralen 
• 14348-23-3 5,8-dihydroxypsoralen 
• 1158849-73-0 8-(4-phenoxybutoxy)psoralen 
• 1253203-57-4 9-(2-(benzyl(methyl)amino)ethoxy)-7H-furo[3,2-g]chromen-7-one 
• 1451067-59-6 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-((2-((2-oxo-2H-furo[3,2-g]chromen-9-yl)oxy)ethyl)amino)pentanenitrile 
• 80386-99-8 9-(methoxy-d₃)-7H-furo[3,2-g]chromen-7-one 

Relevant articles and documents

Synthesis and properties of peptide nucleic acids containing a psoralen unit.

We prepared the psoralen PNA unit from 8-methoxypsoralen and synthesized various PNAs containing psoralen by a typical (t)()Boc method. PNAs containing psoralen (P-PNA) at strand end formed a stable duplex with complementary DNA. The hybridization of P-PNA with complementary DNA resulted in a considerable decrease of the psoralen fluorescence.

Efficient cleavage of DNA by iron(III) triazacyclononane derivatives

Compounds based on (1,4,7-trimethyl-1,4,7-triazacyclononane)iron(III) chloride have been synthesized. Exceedingly low concentrations (approximately 0.5 μM) of these reagents are required to effect single-stranded oxidative cleavage of plasmid DNA at physiological pH and temperature. Approximately 3 breaks per plasmid per micromolar of reagent occur in 1 h at 37°C. The addition of dithiothreitol dramatically increased the effectiveness of these compounds; only 0.05 μM of reagent was required for DNA cleavage. When psoralen (a DNA photocross-linking agent) was attached to the iron complex, irradiation further increased the cleavage efficiency. The DNA cleaving abilities rival those of the cytotoxic antitumor drug bleomycin. Unlike bleomycin, the synthetic agents cut DNA with little sequence specificity. The lability of the chloride ligands, the hard acid character of iron(III), and the absence of base specificity in the DNA cleaving reaction suggest that a cationic iron species binds to the phosphate backbone of DNA. The reaction's dependence on reductants and dissolved oxygen suggests that it proceeds by a redox mechanism. Crystals of (1,4,7-trimethyl-1,4,7-triazacyclononane)FeCl3 (L'FeCl3) belong to the monoclinic space group P21/c, with a = 12.321(2) A?, b = 7.3220(10) A?, c = 15.903(3) A?, V = 1434.7(5) A?3, and Z = 4 at 293 K. Refinement of 145 least squares parameters for 2613 independent reflections with F > 4.0σ(F) converged to R = 3.43% and R(w) = 6.45%. The coordination geometry around iron(III) approximates a trigonally distorted octahedron. The N-Fe-N bond angles (77.8°-78.8°) are compressed, while the Cl-Fe-Cl angles (96.7°-97.0°) are expanded from the octahedral value.

A clickable psoralen to directly quantify DNA interstrand crosslinking and repair

DNA interstrand crosslinks (ICLs) represent physical obstacles to advancing replication forks and transcription complexes. A range of ICL-inducing agents have successfully been incorporated into cancer therapeutics. While studies have adopted UVA-activated psoralens as model ICL-inducing agents for investigating ICL repair, direct detection of the lesion has often been tempered by tagging the psoralen scaffold with a relatively large reporter group that may perturb the biological activity of the parent psoralen. Here a minimally-modified psoralen probe was prepared featuring a small alkyne handle suitable for click chemistry. The psoralen probe, designated 8-propargyloxypsoralen (8-POP), can be activated by UVA in vitro to generate ICLs that are susceptible to post-labeling with an azide-tagged fluorescent reporter via a copper-catalyzed reaction. A modified alkaline comet assay demonstrated that UVA-activated 8-POP proficiently generated ICLs in cells. Cellular 8-POP-DNA lesions were amenable to click-mediated ligation to fluorescent reporters in situ, which permitted their detection and quantitation by fluorescence microscopy and flow cytometry. Small molecule DNA repair inhibitors to 8-POP-treated cells attenuated the removal of 8-POP-DNA lesions, validating 8-POP as an appropriate probe for investigating cellular ICL repair. The post-labeling strategy applied in this study is inexpensive, rapid and highly modular in nature with the potential for multiple applications in DNA repair studies.

-

-

WAMPETIN, A FUROCOUMARIN FROM CLAUSENA WAMPI

A new furocoumarin wampetin has been isolated from Clausena wampi (syn.Clausena lansium).The structure was established from 1H NMR, 13C NMR, MS and chemical data. - Key Word Index: Clausena wampi (Syn.Clausena lansium); Rutaceae; wampetin; furocoumarin; 13C NMR data.

-

-

-

-

Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

A conceptually novel sulfoxonium metathesis reaction between TMSOI and cost-effective DMSO-d6 is developed for the efficient generation of a new trideuteromethylation reagent TDMSOI. The new reagent TDMSOI is produced highly efficiently by simply heating a mixture of TMSOI and DMSO-d6 and directly used for subsequent trideuteromethylation in a "one-pot" operation. The preparative power of the new versatile reagent and the "one-pot" protocol is demonstrated by its use to install the ?CD3 moiety into broad functionalities including phenols, thiophenols, acidic amines, and enolizable methylene units in high yield and at a useful level of deuteration (>87% D).

A biphenyl type furocoumarin compounds and its preparation method and application

The invention discloses a biphenyl furocoumarin compound and a preparation method and an application thereof; the provided biphenyl furocoumarin compound is a new compound with vasodilating activity, which is obtained by modifying and optimizing the structure based on a natural product imperatorin, reserving the pharmacological activity, improving the physicochemical property and enhancing the druggability. The preparation method of the biphenyl furocoumarin compound provided by the invention has the advantages of easily-obtained material source, mild reaction conditions, simple operation in reaction process, and cheap and easily-obtained reagents. The prepared biphenyl furocoumarin compound is a ramification of the imperatorin and has the effect similar to the imperatorin; an in vitro vascular ring tension research shows that the biphenyl furocoumarin compound has a relaxant effect on the mesenteric microvessels of rats, so that the biphenyl furocoumarin compound can be applied to preparing antihypertensive drugs.