EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

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Name:9-methoxyfuro[3,2-g]chromen-7-one
CAS Number: 298-81-7Picture of molecule3D/inchi
Other:12692-94-3
ECHA EINECS - REACH Pre-Reg:206-066-9
FDA UNII:U4VJ29L7BQ
Nikkaji Web:J2.983A
Beilstein Number:0196453
MDL:MFCD00005009
XlogP3:1.90 (est)
Molecular Weight:216.19256000
Formula:C12 H8 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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
 water, 706.2 mg/L @ 25 °C (est)
 acetic acid
 water, 47.6 mg/L @ 30 °C (exp)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Methoxsalen >98%
Odor: characteristic
Use: Methoxsalen also called xanthotoxin, marketed under the trade names Oxsoralen, Deltasoralen, Meladinine is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas
Coompo
For experimental / research use only.
Xanthotoxin from Plants ≥96%
Odor: characteristic
Use: Synergism between myristicin and xanthotoxin, a naturally cooccurring plant toxicant. When added to the diet of final instar larvae, xanthotoxin can induce the cytochrome P450 monooxygenase (P450) activity in midgut microsomes by which it is detoxified. Induction is dose-dependent, increasing sevenfold when larvae feed on parsley treated topically with xanthotoxin at 0.5 or 1.0% fresh weight. Although xanthotoxin exerts much of its toxic effects when photoactivated by ultraviolet light, induction of P450 activity did not differ in the presence or absence of ultraviolet light. Despite a 4.7-fold induction of xanthotoxin-metabolizing P450 activity, total P450 content measured in the same microsomal samples did not increase significantly. These data indicate that multiple forms of P450 exist in the black swallowtail midgut and that they are differentially induced by xanthotoxin. Imperatorin and xanthotoxin protected the animals against maximal electroshock-induced seizures, whereas bergapten and oxypeucedanin, despite their chemical and structural similarities to xanthotoxin and imperatorin, exerted no anticonvulsant activity in this seizure test.
ExtraSynthese
For experimental / research use only.
Xanthotoxin (HPLC) ≥90%
Indo World Trading
Methoxsalen (Xanthotoxin) BP/USP
Santa Cruz Biotechnology
For experimental / research use only.
Methoxsalen ≥99%
Sigma-Aldrich
For experimental / research use only.
Xanthotoxin
analytical standard
TCI AMERICA
For experimental / research use only.
Xanthotoxin >98.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 43 - May cause sensitisation by skin contact.
S 01/02 - Keep locked up and out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 791 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 2, Pg. 309, 1979.

intraperitoneal-rat LD50 158 mg/kg
Drug and Chemical Toxicology. Vol. 2, Pg. 309, 1979.

oral-mouse LD50 423 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 2, Pg. 309, 1979.

intraperitoneal-mouse LD50 250 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 2, Pg. 309, 1979.

oral-guinea pig LD50 505 mg/kg
"Psoralens in Cosmetics and Dermatology, Proceedings of the International Symposium, Paris, 1981," Cahn, J., et al., eds., Paris, Pergamon Press France, 1981Vol. -, Pg. 303, 1981.

Dermal Toxicity:
subcutaneous-rat LD50 1880 mg/kg
Drugs in Japan Vol. -, Pg. 1372, 1995.

subcutaneous-mouse LD50 860 mg/kg
Drugs in Japan Vol. 6, Pg. 837, 1982.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
NLM Hazardous Substances Data Bank:Search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):298-81-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :4114
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
9-methoxyfuro[3,2-g]chromen-7-one
Chemidplus:0000298817
EPA/NOAA CAMEO:hazardous materials
RTECS:LV1400000 for cas# 298-81-7
 
References:
 9-methoxyfuro[3,2-g]chromen-7-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:298-81-7
Pubchem (cid):4114
Pubchem (sid):134974950
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C01864
HMDB (The Human Metabolome Database):HMDB14693
FooDB:FDB012474
Export Tariff Code:2932.20.4500
Haz-Map:View
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
Formulations/Preparations:
•methoxsalen is in 10 mg capsules (oxoralen-ultra). a topical 1% lotion of methoxsalen (oxsoralen) is also available. •capsules, 10 mg. lotion (to be applied by a physician and not to be dispensed to patients), 1%. •topical lotion 1%, oxsoralen (with acetone, alcohol 71%, and propylene glycol), icn •oral capsules 10 mg, 8-mop capsules (with tartrazine), icn; capsules, liquid-filled, oxsoralen-ultra, icn
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 angelica seed
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 anise seed
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 ashitaba
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 bergamot peel
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 caraway plant
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 caraway seed
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 carrot root
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 carrot shoot
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 celery leaf
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 celery plant
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 celery root
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 celery seed
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 celery shoot
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 celery stem
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 coriander fruit
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 coriander seed
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 corn root
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 dill seed
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 fagara xanthoxyloides lam.
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 fennel seed
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 fig leaf
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 goosefoot plant
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 lovage fruit
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 lovage root
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 parsley fruit
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 parsley leaf
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 parsley leaf oil @ 0.24%
Data GC Search Trop Picture
 parsley plant
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 parsley root
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 parsley seed
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 parsley shoot
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 parsley tissue culture
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 parsnip
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 parsnip leaf
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 parsnip root
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 psoralea corylifolia
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 rue plant
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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
 

Articles:

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 "CarapiĆ”" (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.
 
Notes:
a naturally occurring furocoumarin compound found in several species of plants, including psoralea corylifolia. it is a photoactive substance that forms dna adducts in the presence of ultraviolet a irradiation. Present in celery, esp. the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Isol. from Aegle marmelos (bael) Methoxsalen (marketed under the trade name Oxsoralen) is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10mg tablets, which are taken in the amount of 30mg 75 minutes before a PUVA light treatment. The substance is also present in bergamot oil which is used in many perfumes and aromatherapy oils.; Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Methoxsalen-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.; Patients with high blood pressure or a history of liver problems are at risk for inflammation and irreparable damage to both liver and skin. The eyes must be protected from UVA radiation. Side effects include nausea, headaches, dizziness, and in rare cases insomnia. When Eau de Cologne was made, it became a popular perfume. It contained bergamot oil as one of its components. Ladies wearing the perfume on places where the skin was radiated by the sun, noticed that their skin turned brownish at those spots. This is due to the phototoxic effects of methoxsalen present in the bergamot oil. The methoxsalen was removed, and most modern formulations of perfumes containing bergamot are de-methoxsalenised.
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