xanthotoxol

2-propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, d-lactone

CAS: 2009-24-7 C11 H6 O4 MW: 202.16562000

Identification

Namexanthotoxol
IUPAC9-hydroxyfuro[3,2-g]chromen-7-one
CAS Number2009-24-7
EINECS217-923-1
FDA UNIISearch
Molecular FormulaC11 H6 O4
Molecular Weight202.16562000
MDL NumberMFCD00017408
Nikkaji NumberJ7.847F
Beilstein0189491
XlogP31.60 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 249.00 to 251.00 °C. @ 760.00 mm Hg
Boiling Point 428.00 to 429.00 °C. @ 760.00 mm Hg (est)
Flash Point 415.00 °F. TCC ( 212.70 °C. ) (est)
logP (o/w) 1.405 (est)
Soluble in water, 7279 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityoral-rat LD50 480 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for xanthotoxol usage levels up tonot for fragrance use.
Recommendation for xanthotoxol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

angelica angelica seed .02% apple wood apple fruit cnidium monnieri fig leaf parsley parsnip plant parsnip seed

Synonyms

6,7- dihydroxy-5-benzofuran acrylic acid gamma-lactone 7H- furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy- 7H- furo[3, 2-g][1]benzopyran-7-one, 9-hydroxy- 7H- furo[3,2-g][1]benzopyran-7-one, 9-hydroxy- 8- hydroxy-4':5',6:7-furocoumarin 9- hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one 9- hydroxy-7H-furo[3,2-g][1]benzopyran-7-one 9- hydroxy-7h-furo[3,2-g]chromen-7-one 8- hydroxyfuran-2,3,6,7-coumarin 9- hydroxyfurano[3,2-g]chromen-2-one 8- hydroxyfuranocoumarin 9- hydroxyfuro[3,2-g]chromen-7-one 8- hydroxypsoralen 8- hydroxypsoralene 2- propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, d-lactone psoralen, 8-hydroxy- PubMed: Simultaneous determination of imperatorin and its metabolites in vitro and in vivo by a GC-MS method: application to a bioavailability and protein binding ability study in rat plasma. PubMed: Simultaneous determination of imperatorin and its metabolite xanthotoxol in rat plasma by using HPLC-ESI-MS coupled with hollow fiber liquid phase microextraction. PubMed: A new phenolic glycoside from Cnidium monnieri fruits. PubMed: [Study on the coumarin glucosides of Angelica dahurica]. PubMed: Xanthotoxol exerts neuroprotective effects via suppression of the inflammatory response in a rat model of focal cerebral ischemia. PubMed: [A new natural product from root of Angelica dahurica cv. Qibaizhi]. PubMed: Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract. PubMed: New biological activities of Casimiroa edulis leaf extract and isolated compounds. PubMed: Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells. PubMed: An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae. PubMed: Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. PubMed: Biotransformation of bergapten and xanthotoxin by Glomerella cingulata. PubMed: Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA. PubMed: Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry. PubMed: Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity. PubMed: [A new coumarin glycoside from Glehnia littoralis]. PubMed: Aspergillus niger metabolism of citrus furanocoumarin inhibitors of human cytochrome P450 3A4. PubMed: [Studies on chemical constituents from fruits of Paliurus ramosissimus]. PubMed: High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. PubMed: Antimycobacterial activity of geranylated furocoumarins from Tetradium daniellii. PubMed: [Studies on chemical constituents in roots of Heracleum rapula]. PubMed: Separation and quantitative analysis of coumarin compounds from Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook. f by pressurized capillary electrochromatography. PubMed: [Calcium antagonistic effect of Xanthotoxol on isolated guinea pig atria]. PubMed: Biotransformation of imperatorin by Aspergillus flavus. PubMed: Preparative isolation of osthol and xanthotoxol from Common Cnidium Fruit (Chinese traditional herb) using stepwise elution by high-speed counter-current chromatography. PubMed: Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase. PubMed: [Effect of xanthnotoxol on contraction of rabbit thoracic aortic strips]. PubMed: Antioxidative activity of natural products from plants. PubMed: Protein orientation in the Tat-TAR complex determined by psoralen photocross-linking. PubMed: Coumarins and antiplatelet aggregation constituents from Formosan Peucedanum japonicum. PubMed: [Chemical composition of Pleurospermym rivulorum (Diels)]. PubMed: [Chemical constituents of Notopterygium incisum Ting]. PubMed: Photooxygenation of some potentially skin-photosensitizing hydroxyfurocoumarins. Part 2: Xanthotoxol and bergaptol. PubMed: Evaluation of xanthotoxol for central nervous system activity. PubMed: Fate of [(14)C]xanthotoxin (8-methoxypsoralen) in laying hens and a lactating goat. PubMed: Cytotoxic effect of xanthotoxol (8-hydroxypsoralen) on TCTC cells in vitro. PubMed: Induction of defense responses in cultured parsley cells by plant cell wall fragments. PubMed: Occurrence of phytoalexins and other putative defense-related substances in uninfected parsley plants. PubMed: Inactivation and mutagenesis by phototoxins usingEscherichia coli strains differing in sensitivity to near- and far-ultraviolet light. PubMed: Separation of the S-adenosylmethionine: 5- and 8-hydroxyfuranocoumarin O-methyltransferases of Ruta graveolens L. by general ligand affinity chromatography. PubMed: Xanthotoxol (XT) - a potent 5-HT antagonist. PubMed: Pharmacological activity of coumarins isolated from Afraegle paniculata; Part II. PubMed: New syntheses of xanthotoxol and xanthotoxin.