Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:38 UTC |
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Update date | 2020-02-24 19:10:09 UTC |
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Primary ID | FDB000578 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Xanthotoxol |
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Description | Xanthotoxol, also known as 8-hydroxypsoralen, belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group. Xanthotoxol exists in all living organisms, ranging from bacteria to humans. Xanthotoxol has been detected, but not quantified in, several different foods, such as figs (Ficus carica), parsleys (Petroselinum crispum), herbs and spices, green vegetables, and fats and oils. This could make xanthotoxol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Xanthotoxol. |
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CAS Number | 2009-24-7 |
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Structure | |
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Synonyms | Synonym | Source |
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8-Hydroxyfuranocoumarin | ChEBI | 8-Hydroxypsoralen | ChEBI | 5-Benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactone | biospider | 6,7-Dihydroxy-5-benzofuranacrylic acid gamma-lactone | biospider | 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy- | biospider | 7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy- | biospider | 8-Hydroxy-psoralen | HMDB | 8-Hydroxyanthotoxol | biospider | 8-hydroxyfuranocoumarins | biospider | 8-hydroxyfurocoumarin | biospider | 8-hydroxyfurocoumarins | biospider | 8-Hydroxypsoralene | biospider | 9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one | biospider | 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one | HMDB | 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI | db_source | 9-hydroxy-7H-furo[3,2-g]chromen-7-one | biospider | an 8-hydroxyfurocoumarin | biospider | Psoralen, 8-hydroxy- | biospider | Xanthotoxol (6CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C11H6O4 |
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IUPAC name | 9-hydroxy-7H-furo[3,2-g]chromen-7-one |
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InChI Identifier | InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H |
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InChI Key | JWVYQQGERKEAHW-UHFFFAOYSA-N |
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Isomeric SMILES | [H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H] |
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Average Molecular Weight | 202.165 |
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Monoisotopic Molecular Weight | 202.026608673 |
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Classification |
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Description | Belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl 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-hydroxypsoralens |
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Alternative Parents | |
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Substituents | - 8-hydroxypsoralen
- Benzopyran
- 1-benzopyran
- Benzofuran
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Pyran
- Benzenoid
- Furan
- Heteroaromatic compound
- Lactone
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organic oxygen 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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Disposition | Route of exposure: Source: Biological location: |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 65.35%; H 2.99%; O 31.66% | DFC |
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Melting Point | Mp 251-252° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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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 | Not Available | |
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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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Predicted GC-MS | Xanthotoxol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fk9-0920000000-f2a166594cf283c47f5c | Spectrum | Predicted GC-MS | Xanthotoxol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00e9-4090000000-dca534ef96e39d848c13 | Spectrum | Predicted GC-MS | Xanthotoxol, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0090000000-c09589cc1f633fd56111 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0190000000-3ab98291b26fe8eeb4e8 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-2930000000-4691abe312d6e6ecb939 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0290000000-c887179a30886be5e421 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0390000000-4c461f4a9306d3586bfd | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0aor-0900000000-b332ff7a37ce35057295 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0090000000-2e5a86e101fa40f235c9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0290000000-f0e15e059d45f78f5b76 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0560-0900000000-5f24b0525848ab617753 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-6f70ceb2368baddf4f40 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-6f70ceb2368baddf4f40 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0090000000-1553b0f99d6356baaebd | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 58600 |
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ChEMBL ID | CHEMBL1192 |
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KEGG Compound ID | C00841 |
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Pubchem Compound ID | 65090 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15709 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB29457 |
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CRC / DFC (Dictionary of Food Compounds) ID | BDW00-J:BDW00-J |
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EAFUS ID | Not Available |
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Dr. Duke ID | XANTHOTOXOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000582 |
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HET ID | Not Available |
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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 | Not Available |
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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 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 mitotic | | | DUKE | anti nicotinic | 38323 | Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | 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 | Not Available |
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Files |
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MSDS | Not Available |
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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 | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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