Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:00 UTC |
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Update date | 2019-11-26 02:56:32 UTC |
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Primary ID | FDB001510 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4,8,5'-Trimethylpsoralen |
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Description | Trioxsalen, also known as trimethylpsoralen or trisoralen, is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Trioxsalen is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Trioxsalen can be found in wild celery, which makes trioxsalen a potential biomarker for the consumption of this food product. Trioxsalen can be found primarily in blood and urine. Trioxsalen (trimethylpsoralen, Trioxysalen or Trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema. After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage. The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair . Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue (DrugBank). |
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CAS Number | 3902-71-4 |
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Structure | |
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Synonyms | Synonym | Source |
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2',4,8-Trimethylpsoralen | ChEBI | 4,5',8-Trimethylpsoralen | ChEBI | 4,8,5'-Trimethylpsoralen | ChEBI | 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone | ChEBI | Trimethylpsoralen | ChEBI | Trioxisaleno | ChEBI | Trioxysalen | ChEBI | Trioxysalene | ChEBI | Trioxysalenum | ChEBI | Trisoralen | Kegg | 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactone | Generator | 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone | Generator | 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactone | Generator | 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactone | Generator | 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone | Generator | 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactone | Generator, HMDB | 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone | Generator, HMDB | Trioxisalenum | MeSH, HMDB | 2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one | MeSH, HMDB | ICN brand OF trioxsalen | MeSH, HMDB | 2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one | biospider | 2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one | biospider | 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one | biospider | 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one | biospider | 2,5,9-Trimethylpsoralen | biospider | 7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyron | biospider | 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl- | biospider | 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl- | biospider | Antipsoriatic | biospider |
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Predicted Properties | |
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Chemical Formula | C14H12O3 |
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IUPAC name | 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one |
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InChI Identifier | InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3 |
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InChI Key | FMHHVULEAZTJMA-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1 |
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Average Molecular Weight | 228.2433 |
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Monoisotopic Molecular Weight | 228.07864425 |
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Classification |
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Description | Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. |
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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 | Psoralens |
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Alternative Parents | |
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Substituents | - Psoralen
- Benzopyran
- 1-benzopyran
- Benzofuran
- Pyranone
- Benzenoid
- Pyran
- Furan
- Heteroaromatic compound
- Lactone
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- 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 | Source: Biological location: |
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Role | Industrial application: |
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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 | Not Available | |
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Melting Point | 234.5 oC | |
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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 | 4,8,5'-Trimethylpsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0h10-0960000000-966d52d94de4b47d3acd | Spectrum | Predicted GC-MS | 4,8,5'-Trimethylpsoralen, 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 | splash10-004i-0090000000-dcfc8fb3d1851500be83 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fb9-0090000000-9cf76c0cd3483f70877e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ik9-1930000000-364eb5a4711246301410 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-c823a179ff02e7127dc9 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0090000000-e4873a737dacdeebcb1a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003f-2920000000-c752e5912988325469f0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0090000000-c89325e1a7192ec227f4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0090000000-971e5b85c60e64223aa5 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gvk-1930000000-c960ea7d61bacac4f3df | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-f0e0fc28215258fdeb31 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0190000000-11b09e07d8088345c5cb | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0690000000-74d27c4f6ef3bff95576 | Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09314 |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28329 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | TRIMETHYL-PSORALEN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002502 |
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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 | Not Available |
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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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