Showing Compound Xanthotoxin (FDB012474)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2019-11-26 03:06:52 UTC

Primary ID

FDB012474

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthotoxin

Description

Present in celery, especies the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Isolated 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. Xanthotoxin is found in many foods, some of which are parsley, wild celery, dill, and angelica.

CAS Number

298-81-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone	ChEBI
8-Methoxy-2',3',6,7-furocoumarin	ChEBI
8-Methoxy-4',5':6,7-furocoumarin	ChEBI
8-Methoxy-[furano-3'.2':6.7-coumarin]	ChEBI
8-Methoxyfuranocoumarin	ChEBI
8-Methoxypsoralen	ChEBI
8-MOP	ChEBI
8-MP	ChEBI
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one	ChEBI
Meladinine	ChEBI
Meloxine	ChEBI
O-Methylxanthotoxol	ChEBI
Oxsoralen	ChEBI
Ultra mop	ChEBI
Uvadex	ChEBI
Xanthotoxin	ChEBI
6-Hydroxy-7-methoxy-5-benzofuranacrylate delta-lactone	Generator
6-Hydroxy-7-methoxy-5-benzofuranacrylate δ-lactone	Generator
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid δ-lactone	Generator
Methoxalen	HMDB
Xanthotoxine	HMDB
Xanthoxin	HMDB
Zanthotoxin	HMDB
8 MOP	HMDB
Chinoin brand OF methoxsalen	HMDB
Dermox	HMDB
Geroxalen	HMDB
ICN brand 2 OF methoxsalen	HMDB
Methoxsalen mex-america brand	HMDB
Oxsoralen ultra	HMDB
Oxsoralen-ultra	HMDB
8 Methoxypsoralen	HMDB
Ammoidin	HMDB
DB Brand OF methoxsalen	HMDB
Deltasoralen	HMDB
Meladinina	HMDB
Methoxsalen Delta brand	HMDB
Mex-america brand OF methoxsalen	HMDB
Méladinine	HMDB
Sanofi-synthelabo brand OF methoxsalen	HMDB
8MOP	HMDB
Boehringer ingelheim brand OF methoxsalen	HMDB
Galderma brand OF methoxsalen	HMDB
Methoxa-dome	HMDB
Methoxsalen canderm brand	HMDB
Methoxsalen chinoin brand	HMDB
Methoxsalen dermatech brand	HMDB
Methoxsalen sanofi-synthelabo brand	HMDB
Puvalen	HMDB
Sanofi synthelabo brand OF methoxsalen	HMDB
Ultramop	HMDB
Canderm brand OF methoxsalen	HMDB
Delta Brand OF methoxsalen	HMDB
Dermatech brand OF methoxsalen	HMDB
ICN brand 1 OF methoxsalen	HMDB
ICN brand 3 OF methoxsalen	HMDB
Methoxa dome	HMDB
Mex america brand OF methoxsalen	HMDB
6-hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone	biospider
7-Furocoumarin	biospider
7H-Furo(3,2-g)(1)benzopyran-7-one, 9-methoxy-	biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-	biospider
8-Methoxy	biospider
8-Methoxy-(furano-3'.2':6.7-coumarin)	biospider
8-Methoxy-2',3',6, 7-furocoumarin	biospider
8-Methoxy-4',5',6,7-furocoumarin	biospider
8-Methoxy-6,7-furanocoumarin	biospider
8-Methoxy(furano-3'.2':6.7-coumarin)	biospider
8-Methoxypsoralen with ultraviolet A therapy	biospider
8-Methoxypsoralene	biospider
9-(methyloxy)-7H-furo[3,2-g]chromen-7-one	biospider
9-metho xy-7H-furo(3,2-g)benzopyran-7-one	biospider
9-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one	biospider
9-Methoxy-7H-furo(3,2-g)benzopyran-7-one	biospider
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI, 8CI	db_source
9-Methoxy-7H-furo[3,2-g]chromen-7-one	biospider
9-Methoxyfuro(3,2-g)chromen-7-one	biospider
9-Methoxyfuro[3,2-g][1]benzopyran-7-one	biospider
9-Methoxyfuro[3,2-g]chromen-7-one	db_source
9-Methoxypsoralen	db_source
Ammodin	biospider
Boehringer ingelheim brand of methoxsalen	biospider
Canderm brand of methoxsalen	biospider
Chinoin brand of methoxsalen	biospider
DB brand of methoxsalen	biospider
Delta brand of methoxsalen	biospider
Dermatech brand of methoxsalen	biospider
Galderma brand of methoxsalen	biospider
ICN Brand 1 of Methoxsalen	biospider
ICN Brand 2 of Methoxsalen	biospider
ICN Brand 3 of Methoxsalen	biospider
Meladinin	biospider
Meladinin (van)	biospider
Meladoxen	biospider
Methoxa-Dome	db_source
Methoxaten	biospider
Methoxsalen	ChEBI
Methoxsalen (JP15/USP)	biospider
Methoxsalen [ban:jan]	biospider
Methoxsalen delta brand	biospider
Methoxsalen plus ultraviolet radiation	biospider
Methoxsalen with ultra-violet a theraphy	biospider
Methoxsalen, 8-	biospider
Methoxsalen, BAN	db_source
Methoxy-8-psoralen	biospider
Mex america brand of methoxsalen	biospider
Mex-america brand of methoxsalen	biospider
New-meladinin	biospider
O-methylxanthotoxol	biospider
Oxoralen	biospider
Oxsoralen (TN)	biospider
Oxsoralen lotion	biospider
Oxsoralen ul tra	biospider
Oxypsoralen	biospider
Proralone-mop	biospider
Psoralen-mop	biospider
Psoralon-mop	biospider
Puvamet	biospider
Sanofi synthelabo brand of methoxsalen	biospider
Sanofi-synthelabo brand of methoxsalen	biospider

Predicted Properties

Not Available

Chemical Formula

C12H8O4

IUPAC name

InChI Identifier

InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3

InChI Key

QXKHYNVANLEOEG-UHFFFAOYSA-N

Isomeric SMILES

COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

Average Molecular Weight

216.192

Monoisotopic Molecular Weight

216.042258738

Classification

Description

Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-methoxypsoralens

Alternative Parents

Substituents

8-methoxypsoralen
Benzopyran
1-benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:18358 )
psoralens (CHEBI:18358 )
Polyketides (C01864 )
Furanocoumarins (C01864 )
an 8-methoxyfurocoumarin (CPD-13042 )

Ontology

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Biofluid and excreta:

Role

Indirect biological role:

Carcinogen

Industrial application:

Drug

Pharmaceutical industry:

Antineoplastic agent:

Antitumor

Biological role:

Pigment

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 66.67%; H 3.73%; O 29.60%	DFC
Melting Point	Mp 148°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.0476 mg/mL at 30 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	301 (e 14400) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Not Available

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

719

DrugBank ID

DB00553

HMDB ID

HMDB14693

CRC / DFC (Dictionary of Food Compounds) ID

HHG12-C:HHG12-C

EAFUS ID

Not Available

Dr. Duke ID

8-METHOXY-PSORALEN|XANTHOTOXIN

BIGG ID

Not Available

KNApSAcK ID

C00000576

HET ID

8MO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Xanthotoxin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dermatitic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti feedant			DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti keratotic			DUKE
anti leucodermic			DUKE
anti lymphomic			DUKE
anti mitotic			DUKE
anti mutagenic			DUKE
anti mycotic			DUKE
anti pityriasic			DUKE
anti pruritic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti scleromyxoedemic	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti vitiligic			DUKE
artemicide			DUKE
bufocide			DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
dermatitigenic			DUKE
emetic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
fungistat			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
hypertrichotic			DUKE
immunosuppressant	35705	An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
lipolytic			DUKE
lymphocytogenic			DUKE
melaninogenic			DUKE
mitogenic			DUKE
molluscicide	33904	A substance used to destroy pests of the phylum Mollusca.	DUKE
mutagenic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
photodermatitigenic			DUKE
phototoxic			DUKE
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE
piscicide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.