Xanthotoxol

Base Information

• Chemical Name: Xanthotoxol
• CAS No.: 2009-24-7
• Molecular Formula: C11H6O4
• Molecular Weight: 202.166
• Hs Code.: 29329990
• European Community (EC) Number: 217-923-1
• NSC Number: 401269
• UNII: 8RL486L8A5
• DSSTox Substance ID: DTXSID50173910
• Nikkaji Number: J7.847F
• Wikipedia: Xanthotoxol
• Wikidata: Q4021722
• Metabolomics Workbench ID: 43855
• ChEMBL ID: CHEMBL1192
• Mol file: 2009-24-7.mol

Synonyms:8-hydroxypsoralen;xanthotoxol

Chemical Property of Xanthotoxol

Chemical Property:

• Vapor Pressure: 6.22E-08mmHg at 25°C
• Melting Point: 250 °C
• Refractive Index: 1.71
• Boiling Point: 428.1 °C at 760 mmHg
• PKA: 5.74±0.20(Predicted)
• Flash Point: 212.7 °C
• PSA: 63.58000
• Density: 1.526 g/cm³
• LogP: 2.24480
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 202.02660867
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

95%-98% ^*data from raw suppliers

Xanthotoxol ^*data from reagent suppliers

Safty Information:

• Statements: 25
• Safety Statements: 20-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O
• 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.
• 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. 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.

Technology Process of Xanthotoxol

There total 22 articles about Xanthotoxol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

imperatorin (482-44-0) → 8-hydroxypsoralen (2009-24-7)

Guidance literature:

With hydrogenchloride; In methanol; water;

DOI:10.1007/s00044-014-1312-6

Reference yield: 98.0%

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (298-81-7) → 8-hydroxypsoralen (2009-24-7)

Guidance literature:

With boron tribromide; In dichloromethane;

DOI:10.1111/php.13138

Reference yield: 82.0%

9-acetyl-7H-furo[3,2-g]chromen-7-one (86290-70-2) → 8-hydroxypsoralen (2009-24-7)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In 1,4-dioxane; for 2h;

DOI:10.1080/00397910601038616

upstream raw materials:

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one

imperatorin

xanthotoxol 8-O-β-D-glucopyranoside

wampetin

Downstream raw materials:

9-(methoxy-d₃)-7H-furo[3,2-g]chromen-7-one

Refernces

• 1、 Row,Brown,Stachulski,Lennard. "Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4". . p. 3865 - 3871. Retrieved 2006.
• 2、 El-Gogary, Tarek M,El-Gendy, Eman M. "Noncovalent attachment of psoralen derivatives with DNA: Hartree-Fock and density functional studies on the probes.". . p. 2635 - 2644. Retrieved 2003.
• 3、 Lakshmi, Vijai,Prakash, Dhan,Raj, Kanwal,Kapil, Randhir S.,Popli, Satya P.. "MONOTERPENOID FURANOCOUMARIN LACTONES FROM CLAUSENA ANISATA". . p. 2629 - 2632. Retrieved 1984.
• 4、 Hashimoto, Akiko,Takamura-Enya, Takeji,Oda, Yoshimitsu. "Synthesis and In Vitro Biological Evaluation of Psoralen-Linked Fullerenes". . p. 1403 - 1411. Retrieved 2019.
• 5、 Dukhovlinova et al.. "-". . . Retrieved 1974.
• 6、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and β-secretase inhibitory activity". . p. 455 - 459. Retrieved 2010.
• 7、 Hou, Ya-Jing,Wang, Cheng,Wang, Tao,Huang, Li-Min,Lin, Yuan-Yuan,He, Huai-Zhen. "Design, synthesis, and evaluation of new series of Imperatorin analogs with potential vasodilatory activity". . p. 43 - 50. Retrieved 2019.
• 8、 -. "Structural modifier of 8-methoxypsoralen as well as preparation method and application of structural modifier". Paragraph 0076; 0084; 0086-0087. . Retrieved 2019/04/04.