xanthotoxol
2-propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, d-lactone
Identification
| Name | xanthotoxol |
| IUPAC | 9-hydroxyfuro[3,2-g]chromen-7-one |
| CAS Number | 2009-24-7 |
| EINECS | 217-923-1 |
| FDA UNII | Search |
| Molecular Formula | C11 H6 O4 |
| Molecular Weight | 202.16562000 |
| MDL Number | MFCD00017408 |
| Nikkaji Number | J7.847F |
| Beilstein | 0189491 |
| XlogP3 | 1.60 (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 Toxicity | oral-rat LD50 480 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for xanthotoxol usage levels up to | not for fragrance use. |
| Recommendation for xanthotoxol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.