1.0 2010-04-08 22:05:00 UTC 2025-11-18 22:31:44 UTC FDB001510 4,8,5'-Trimethylpsoralen 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). 2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one 2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one 2,5,9-Trimethylpsoralen 2',4,8-Trimethylpsoralen 4,5',8-Trimethylpsoralen 7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyron 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl- 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl- Antipsoriatic Trimethylpsoralen Trioxysalen Trisoralen C14H12O3 228.2433 228.07864425 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one trioxsalen 3902-71-4 CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1 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 FMHHVULEAZTJMA-UHFFFAOYSA-N 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. Psoralens Organic compounds Phenylpropanoids and polyketides Coumarins and derivatives Furanocoumarins Aromatic heteropolycyclic compounds 1-benzopyrans Benzenoids Benzofurans Furans Heteroaromatic compounds Hydrocarbon derivatives Lactones Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives 1-benzopyran Aromatic heteropolycyclic compound Benzenoid Benzofuran Benzopyran Furan Heteroaromatic compound Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Psoralen Pyran Pyranone Furanocoumarins psoralens logp 3.26 ALOGPS logs -3.56 ALOGPS solubility 6.27e-02 g/l ALOGPS melting_point 234.5 oC logp 2.95 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one ChemAxon average_mass 228.2433 ChemAxon mono_mass 228.07864425 ChemAxon smiles CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1 ChemAxon formula C14H12O3 ChemAxon inchi 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 ChemAxon inchikey FMHHVULEAZTJMA-UHFFFAOYSA-N ChemAxon polar_surface_area 39.44 ChemAxon refractivity 64.86 ChemAxon polarizability 24.77 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 65202 Specdb::MsMs 65203 Specdb::MsMs 65204 Specdb::MsMs 122559 Specdb::MsMs 122560 Specdb::MsMs 122561 Specdb::MsMs 3222136 Specdb::MsMs 3222137 Specdb::MsMs 3222138 Specdb::MsMs 3222139 Specdb::MsMs 3222140 Specdb::MsMs 3222141 Specdb::CMs 23200 Specdb::CMs 150193 HMDB0015575 28329 Wild celery Type 1 specific Apium graveolens 4045