| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:11 UTC |
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| Update date | 2019-11-26 03:06:52 UTC |
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| Primary ID | FDB012474 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Xanthotoxin |
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| 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. |
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| CAS Number | 298-81-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 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 |
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| Predicted Properties | |
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| Chemical Formula | C12H8O4 |
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| IUPAC name | 9-methoxy-7H-furo[3,2-g]chromen-7-one |
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| 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 |
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| InChI Key | QXKHYNVANLEOEG-UHFFFAOYSA-N |
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| Isomeric SMILES | COC1=C2OC(=O)C=CC2=CC2=C1OC=C2 |
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| Average Molecular Weight | 216.192 |
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| Monoisotopic Molecular Weight | 216.042258738 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Coumarins and derivatives |
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| Sub Class | Furanocoumarins |
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| Direct Parent | 8-methoxypsoralens |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Indirect biological role: Industrial application: Biological role: |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 66.67%; H 3.73%; O 29.60% | DFC |
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| Melting Point | Mp 148° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 0.0476 mg/mL at 30 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | 301 (e 14400) (EtOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| EI-MS | Mass Spectrum (Electron Ionization) | splash10-014i-9670000000-3e0fa2e9c81c3bc1d936 | Spectrum | | GC-MS | Xanthotoxin, non-derivatized, GC-MS Spectrum | splash10-00ri-6940000000-921a3e8adbbde5f7a0c3 | Spectrum | | GC-MS | Xanthotoxin, non-derivatized, GC-MS Spectrum | splash10-003b-4950000000-4e2c001531825f6dddca | Spectrum | | GC-MS | Xanthotoxin, non-derivatized, GC-MS Spectrum | splash10-00ri-6940000000-921a3e8adbbde5f7a0c3 | Spectrum | | GC-MS | Xanthotoxin, non-derivatized, GC-MS Spectrum | splash10-003b-4950000000-4e2c001531825f6dddca | Spectrum | | Predicted GC-MS | Xanthotoxin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-1920000000-98f6cfda190045d0762a | Spectrum | | Predicted GC-MS | Xanthotoxin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-014i-1590000000-f70cf2b0756e8c80c17b | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-014i-0890000000-f76d6fb28854a5d7b6cd | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0fk9-0920000000-c2bd0b76c5aed757e904 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014i-0090000000-cecd035cc60695427f78 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0gb9-0290000000-2e17076c991ea61ced1a | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0uk9-0970000000-59c3b8004baa44f8d3a5 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014i-0190000000-cc04ec8c7265ba3a7297 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0970000000-82c4c7eefd54ad509f69 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00xs-0900000000-991b5b7dc028219e593b | Spectrum | | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0970000000-dc6cd01d5d2e5eeaae30 | Spectrum | | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0970000000-ee8aa480dca6e72a74fb | Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-014i-0890000000-f76d6fb28854a5d7b6cd | Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-014i-1590000000-f70cf2b0756e8c80c17b | Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0fk9-0920000000-c2bd0b76c5aed757e904 | Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0gi0-1960000000-82bc07f73bc5b2044642 | Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-014i-0690000000-770dc5d0db7e86d8ba07 | Spectrum | | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-00dj-0900000000-b06196cd7070da3a2e98 | Spectrum | | MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-014i-0090000000-ed4db851d39c50628cea | Spectrum | | MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-0uxr-0490000000-6e7169196da6a70b89d6 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0090000000-4767833559e7bd183ce0 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0090000000-c471bf567e8a63e00e51 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01bi-0930000000-72a72a3eb013e045bdb0 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0290000000-c9557f276875a3bf1d2b | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0390000000-ff927b8db6ef70ef822d | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-0910000000-d2e511be224be1b3530e | Spectrum |
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| NMR | | Type | Description | | View |
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| 1D NMR | 1H NMR Spectrum | | Spectrum |
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| External Links |
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| ChemSpider ID | 3971 |
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| ChEMBL ID | CHEMBL416 |
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| KEGG Compound ID | C01864 |
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| Pubchem Compound ID | 4114 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 719 |
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| DrugBank ID | DB00553 |
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| HMDB ID | HMDB14693 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HHG12-C:HHG12-C |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | 8-METHOXY-PSORALEN|XANTHOTOXIN |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00000576 |
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| HET ID | 8MO |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Xanthotoxin |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| 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 |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| 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
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| 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.
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