xanthotoxin

8-methoxy-2',3',6,7-furocoumarin

CAS: 298-81-7 C12 H8 O4 MW: 216.19256000

Identification

Namexanthotoxin
IUPAC9-methoxyfuro[3,2-g]chromen-7-one
CAS Number298-81-7
EINECS206-066-9
FDA UNIIU4VJ29L7BQ
Molecular FormulaC12 H8 O4
Molecular Weight216.19256000
MDL NumberMFCD00005009
Nikkaji NumberJ2.983A
Beilstein0196453
XlogP31.90 (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 SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 791 mg/kg
Dermal Toxicitysubcutaneous-rat LD50 1880 mg/kg
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 xanthotoxin usage levels up tonot for fragrance use.
Recommendation for xanthotoxin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

angelica seed anise seed ashitaba bergamot peel caraway plant caraway seed carrot root carrot shoot celery leaf celery plant celery root celery seed celery shoot celery stem coriander fruit coriander seed corn root dill seed fagara xanthoxyloides lam. fennel seed fig leaf goosefoot plant lovage fruit lovage root parsley fruit parsley leaf parsley leaf oil @ 0.24% Data parsley plant parsley root parsley seed parsley shoot parsley tissue culture parsnip parsnip leaf parsnip root psoralea corylifolia rue plant

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.