xanthotoxin
8-methoxy-2',3',6,7-furocoumarin
Identification
| Name | xanthotoxin |
| IUPAC | 9-methoxyfuro[3,2-g]chromen-7-one |
| CAS Number | 298-81-7 |
| EINECS | 206-066-9 |
| FDA UNII | U4VJ29L7BQ |
| Molecular Formula | C12 H8 O4 |
| Molecular Weight | 216.19256000 |
| MDL Number | MFCD00005009 |
| Nikkaji Number | J2.983A |
| Beilstein | 0196453 |
| XlogP3 | 1.90 (est) |
Regulatory
Physical Properties
| Appearance | white to yellow powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 146.00 to 148.00 °C. @ 760.00 mm Hg |
| Boiling Point | 414.00 to 415.00 °C. @ 760.00 mm Hg |
| Flash Point | 400.00 °F. TCC ( 204.44 °C. ) |
| logP (o/w) | 1.523 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 791 mg/kg |
| Dermal Toxicity | subcutaneous-rat LD50 1880 mg/kg |
| 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 xanthotoxin usage levels up to | not for fragrance use. |
| Recommendation for xanthotoxin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
ammodin
ammoidin
5-
benzofuranacrylic acid, 6-hydroxy-7-methoxy-, d-lactone
deltasoralen
dermox
7H-
furo(3,2-g)(1)benzopyran-7-one, 9-methoxy-
7H-
furo[3,2-g][1]benzopyran-7-one, 9-methoxy-
7-
furocoumarin
geroxalen
6-
hydroxy-7-methoxy-5-benzofuranacrylic acid d-lactone
meladinin
meladoxen
meloxine
9-
metho xy-7H-furo(3,2-g)benzopyran-7-one
methoxa-dome
methoxalen
methoxaten
methoxsalen
methoxsalen (xanthotoxin) BP/USP
8-
methoxy (furano-3'.2':6.7-coumarin)
8-
methoxy-(furano-3'.2':6.7-coumarin)
8-
methoxy-[furano-3'.2':6.7-coumarin]
8-
methoxy-2',3',6,7-furocoumarin
9-
methoxy-2H-furo[3,2-g]chromen-2-one
9-
methoxy-7H-furo(3,2-g)(1)benzopyran-7-one
9-
methoxy-7H-furo[3,2-g][1]benzopyran-7-one
9-
methoxy-7H-furo[3,2-g]chromen-7-one
methoxy-8-psoralen
8-
methoxy[furano-3',2':6,7-coumarin]
8-
methoxyfurano-2,3,6,7-coumarin
9-
methoxyfurano[3,2-g]chromen-2-one
8-
methoxyfuranocoumarin
9-
methoxyfuro(3,2-g)chromen-7-one
9-
methoxyfuro[3,2-g][1]benzopyran-7-one
9-
methoxyfuro[3,2-g]chromen-7-one
8-
methoxypsoralen
9-
methoxypsoralen
9-(
methyloxy)-7H-furo[3,2-g]chromen-7-one
O-
methylxanthotoxol
8-
MOP
oxoralen
oxsoralen
proralone-MOP
psoralen-MOP
psoralon-MOP
puvalen
puvamet
ultra MOP
ultramop
ultramop lotion
uvadex
zanthotoxin
PubMed:
Furanocoumarins in celeriac from different farming systems: a 3-year study.
J-Stage:
Effects of Methoxsalen from Poncirus trifoliata on Acetylcholinesterase and Trimethyltin-Induced Learning and Memory Impairment
PubMed:
Furocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice.
PubMed:
Effects of methoxsalen from Poncirus trifoliata on acetylcholinesterase and trimethyltin-induced learning and memory impairment.
PubMed:
Percutaneous penetration of 5-methoxypsoralen in rhesus monkeys.
PubMed:
[High-performance liquid chromatography for determination of psoralene, bergapten and apigenin in Ficus hirta Vahl].
PubMed:
Dishabituating long-term memory for gustatory habituation in the cabbage looper, Trichoplusia ni.
PubMed:
Biotransformation of bergapten and xanthotoxin by Glomerella cingulata.
PubMed:
Botanicals in dermatology: an evidence-based review.
PubMed:
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.
PubMed:
Inhibitory effect of Poncirus trifoliate on acetylcholinesterase and attenuating activity against trimethyltin-induced learning and memory impairment.
PubMed:
[Contents of furanocoumarins in grapefruit juice and health foods].
PubMed:
Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract.
PubMed:
Bioassay directed identification of natural aryl hydrocarbon-receptor agonists in marmalade.
PubMed:
Different modes of inhibition of mouse Cyp2a5 and rat CYP2A3 by the food-derived 8-methoxypsoralen.
PubMed:
Inhibition on human liver cytochrome P450 3A4 by constituents of fennel (Foeniculum vulgare): identification and characterization of a mechanism-based inactivator.
PubMed:
In vivo photochemical skin micronucleus test using a sunlight simulator: detection of 8-methoxypsoralen and benzo[a]pyrene in hairless mice.
PubMed:
Can dietary furanocoumarin ingestion enhance the erythemal response during high-dose UVA1 therapy?
PubMed:
Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus.
PubMed:
Antioxidant activity of citrus limonoids, flavonoids, and coumarins.
PubMed:
Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.
PubMed:
Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster.
PubMed:
Phytotoxins from the leaves of Ruta graveolens.
PubMed:
LC determination of impurities in methoxsalen drug substance: isolation and identification of isopimpinellin as a major impurity by atmospheric pressure chemical ionization LC/MS and NMR.
PubMed:
Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips.
PubMed:
Simultaneous determination of furanocoumarins in infusions and decoctions from "Carapiá" (dorstenia species) by high-performance liquid chromatography.
PubMed:
Furanocoumarins in celery and parsnips: method and multiyear Canadian survey.
PubMed:
Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins.
PubMed:
Metabolism-dependent hepatotoxicity of methimazole in mice depleted of glutathione.
PubMed:
The North American experience with photopheresis.
PubMed:
Photoactivated 8-methoxypsoralen treatment causes a peptide-dependent increase in antigen display by transformed lymphocytes.
PubMed:
Carbaryl induces CYP1A1 gene expression in HepG2 and HaCaT cells but is not a ligand of the human hepatic Ah receptor.
PubMed:
Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds.
PubMed:
Photosensitized decontamination of blood with the silicon phthalocyanine Pc 4: no activation of the human immunodeficiency virus promoter.
PubMed:
Isolation and identification of antimicrobial furocoumarins from parsley.
PubMed:
Adult specific expression and induction of cytochrome P450lpr in house flies.
PubMed:
Styrene-induced hepatotoxicity in mice depleted of glutathione.
PubMed:
Treatment of psoriasis with psoralens and ultraviolet A. A double-blind comparison of 8-methoxypsoralen and 5-methoxypsoralen.
PubMed:
Food-induced increase in bioavailability of 5-methoxypsoralen.
PubMed:
Phototoxic coumarins in limes.
PubMed:
Psoralen photosensitization and plasma and cutaneous beta-carotene concentrations in hairless mice.
PubMed:
The influence of food on 8-methoxypsoralen serum concentration and minimal phototoxic dose.
PubMed:
Spectral effects in activation of the human immunodeficiency virus promoter by psoralens plus ultraviolet A treatment.
PubMed:
Fate of [(14)C]xanthotoxin (8-methoxypsoralen) in laying hens and a lactating goat.
PubMed:
Phototoxicity testing in guinea-pigs.
PubMed:
Nephrotoxicity of thiazoles structurally related to thiabendazole in mice depleted of glutathione by treatment with buthionine sulfoximine.
PubMed:
Dietary intake and risk assessment of phototoxic furocoumarins in humans.
PubMed:
Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine.
PubMed:
[Influence of retinoids on the bioavailability of methoxy-8-psoralen].
PubMed:
Defense of parsnip webworm against phototoxic furanocoumarins: Role of antioxidant enzymes.
PubMed:
Excretion and tissue distribution of 14C-labelled 8-methoxypsoralen in beagle dogs and miniature pigs.
PubMed:
Inhibition of herpes virus plaquing capacity in human diploid fibroblasts treated with gilvocarcin V plus near UV radiation.
PubMed:
Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine.
PubMed:
Natural pesticides and bioactive components in foods.
PubMed:
Antioxidant enzyme level response to prooxidant allelochemicals in larvae of the southern armyworm moth, Spodoptera eridania.
PubMed:
A predictive mouse ear-swelling model for investigating topical phototoxicity.
PubMed:
Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species.
PubMed:
Kinetics of 8-methoxypsoralen and 5-methoxypsoralen distribution in guinea pig serum, epidermis and ocular lens.
PubMed:
Clinical pharmacokinetics of methoxsalen and other psoralens.
PubMed:
5-Methoxypsoralen.
PubMed:
The bergapten content of garden parsley and its significance in causing cutaneous photosensitization.
PubMed:
Use of the occlusive patch to evaluate the photosensitive properties of chemicals in guinea-pigs.
PubMed:
A device for irradiating guinea-pig skin with ultraviolet light.
PubMed:
Quantitative assessment of phototoxicity in the skin of hairless mice.
PubMed:
Phototoxic dermatitis caused by celery infected by Sclerotinia sclerotiorum.
PubMed:
Long-term risks of psoralen and UV-A therapy for psoriasis.
PubMed:
HPLC analysis of linear furocoumarins (psoralens) in healthy celery (Apium graveolens).
PubMed:
Genotoxicity of 5-methoxypsoralen and near ultraviolet light in repair-deficient strains of Escherichia coli WP2.
PubMed:
Influenced of food on the kinetics of 8-methoxypsoralen in serum and suction blister fluid in psoriatic patients.
PubMed:
Institutional pharmacists' guide to complying with PPI regulations.
PubMed:
Effect of food on kinetics of 8-methoxsalen.
PubMed:
Phototoxicity and photocarcinogenesis: comparative effects of anthracene and 8-methoxypsoralen in the skin of mice.
PubMed:
Experimental modification of photocarcinogenesis. II. Fluorescent whitening agents and simulated solar UVR.
PubMed:
Experimental modification of photocarcinogenesis. III. Simulation of exposure to sunlight and fluorescent whitening agents.
PubMed:
Isolation and identification of xanthotoxin (8-methoxypsoralen) and bergapten (5-methoxypsoralen) from celery infected with Sclerotinia sclerotiorum.