Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:32 UTC
Primary IDFDB001510
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4,8,5'-Trimethylpsoralen
DescriptionTrioxsalen, 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).
CAS Number3902-71-4
Structure
Thumb
Synonyms
SynonymSource
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
2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-onebiospider
2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-onebiospider
2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-onebiospider
2,5,9-Trimethylfuro[3,2-g]benzopyran-7-onebiospider
2,5,9-Trimethylpsoralenbiospider
7-Oxo-2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyronbiospider
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
Antipsoriaticbiospider
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
Chemical FormulaC14H12O3
IUPAC name2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
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
Isomeric SMILESCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
Average Molecular Weight228.2433
Monoisotopic Molecular Weight228.07864425
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point234.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4,8,5'-Trimethylpsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h10-0960000000-966d52d94de4b47d3acdSpectrum
Predicted GC-MS4,8,5'-Trimethylpsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dcfc8fb3d1851500be83Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0090000000-9cf76c0cd3483f70877eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ik9-1930000000-364eb5a4711246301410Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-c823a179ff02e7127dc9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-e4873a737dacdeebcb1aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003f-2920000000-c752e5912988325469f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-c89325e1a7192ec227f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-971e5b85c60e64223aa5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvk-1930000000-c960ea7d61bacac4f3dfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f0e0fc28215258fdeb31Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-11b09e07d8088345c5cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0690000000-74d27c4f6ef3bff95576Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09314
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID28329
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDTRIMETHYL-PSORALEN
BIGG IDNot Available
KNApSAcK IDC00002502
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.