4,5',8-Trimethylpsoralen (CED0009029)

Record Information
Version1.0
Creation Date2016-05-20 16:15:30 UTC
Update Date2026-08-19 04:52:16 UTC
Accession NumberCHEM016120
Identification
Common Name4,5',8-Trimethylpsoralen
ClassSmall Molecule
Description
4,5',8-Trimethylpsoralen is an organic compound with the chemical formula C14H12O3 and an average molecular weight of 228.24 g/mol. 4,5',8-Trimethylpsoralen belongs to the furanocoumarins, a subclass of coumarins and derivatives within the organic compounds. It is further classified within the superclass of phenylpropanoids and polyketides. The compound is associated with 29 recorded sources across diverse sectors. In the realm of healthcare, pharmaceuticals, and veterinary products, it is utilized as an antipsoriatic. It is found in building and construction materials, specifically tents or canopies. Within the food, food processing, and cookware sector, it is linked to food preservation, the preparation of vinegar, the preparation of wort, the preparation of wine or sparkling wine, and fermentation processes for beer. Its presence is also recorded in household cleaning and consumer products, including bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and three additional sources. Furthermore, it is found in electrical and electronic equipment, including amplifiers, antennas, electric switches, cores yokes or armatures, conductors or conductive bodies characterised by the conductive materials, and eight other sources. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2',4,8-TrimethylpsoralenChEBI
4,5',8-TrimethylpsoralenChEBI
4,8,5'-TrimethylpsoralenChEBI
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneChEBI
TrimethylpsoralenChEBI
TrioxisalenoChEBI
TrioxysalenChEBI
TrioxysaleneChEBI
TrioxysalenumChEBI
TrisoralenKegg
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneGenerator
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator, HMDB
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator, HMDB
TrioxisalenumMeSH, HMDB
2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-oneMeSH, HMDB
ICN brand OF trioxsalenMeSH, HMDB
Chemical FormulaC14H12O3
Average Molecular Mass228.243 g/mol
Monoisotopic Mass228.079 g/mol
CAS Registry Number3902-71-4
IUPAC Name2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
Traditional Nametrioxsalen
SMILESCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
InChI IdentifierInChI=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
InChI KeyFMHHVULEAZTJMA-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP3.26ALOGPS
logP2.95ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.86 m³·mol⁻¹ChemAxon
Polarizability24.77 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0h10-0960000000-966d52d94de4b47d3acdNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-dcfc8fb3d1851500be83Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fb9-0090000000-9cf76c0cd3483f70877eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-1930000000-364eb5a4711246301410Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-c823a179ff02e7127dc9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-e4873a737dacdeebcb1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003f-2920000000-c752e5912988325469f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-c89325e1a7192ec227f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-971e5b85c60e64223aa5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gvk-1930000000-c960ea7d61bacac4f3dfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-f0e0fc28215258fdeb31Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0190000000-11b09e07d8088345c5cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0690000000-74d27c4f6ef3bff95576Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
847.0Log mg/kg[480:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
305AntipsoriaticsHealthcare, pharmaceuticals & veterinary productsNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)621.159
Immunoglobulin lambda variable 6-57 structureClick to view 3D structureImmunoglobulin lambda variable 6-57P01721HumansPredicted (SEA)9.10836
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)3633.69
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)4212.81
Aldehyde dehydrogenase, mitochondrial structureClick to view 3D structureAldehyde dehydrogenase, mitochondrialP05091HumansPredicted (SEA)54.3388
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)3392.36
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)19.2288
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)239.386
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)133.667
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)248.65
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)304.079
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)343.004
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)546.891
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)650.508
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)465.305
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)1035.63
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)507.733
Retinal dehydrogenase 2 structureClick to view 3D structureRetinal dehydrogenase 2O94788HumansPredicted (SEA)6.69503
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)312.253
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)164.262
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)294.114
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)697.218
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)362.933
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)696.05
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)1995.04
Concentrations
Not Available
External Links
DrugBank IDDB04571
HMDB IDHMDB0015575
FooDB IDFDB001510
Phenol Explorer IDNot Available
KNApSAcK IDC00002502
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrioxsalen
Chemspider ID5383
ChEBI ID28329
PubChem Compound ID5585
Kegg Compound IDC09314
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6.
2. Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2.
3. Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7.
4. Goldenberg M, Welsh J, Haas R, Rideout DC, Cantor CR: Synthesis and properties of novel psoralen derivatives. Biochemistry. 1988 Sep 6;27(18):6971-6. doi: 10.1021/bi00418a045.
5. Kaidbey KH, Kligman AM: Photopigmentation with trioxsalen. Arch Dermatol. 1974 May;109(5):674-7.
6. Sehgal VN: Editorial: Effectiveness of trioxsalen therapy for vitiligo. Arch Dermatol. 1974 Dec;110(6):957-8. doi: 10.1001/archderm.1974.01630120089029.