CAS 66-97-7|<i>7H</i>-furo[3,2-g][1]benzopyran-7-one|psoralen|7H-furo[3,2-g]chromen-7-one|Psoralen|Furo[3,2-g]coumarin|7H-Furo[3,2-g]benzopyran-7-one|Psoralen|Psoralene|Ficusin|Furo[4',5':6,7]coumar...

General Information

Structure

Molecular Formula

C₁₁H₆O₃

Molecular Mass

186.16354

Exact Mass

186.03169405

Charge

InChI

InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H

InChIKey

ZCCUUQDIBDJBTK-UHFFFAOYSA-N

Canonic Smiles

O=c1ccc2c(o1)cc1c(c2)cco1

Isomeric Smiles

O=c1oc2cc3occc3cc2cc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.9424831

LogD (pH = 7.4)

1.9424831

Log P

1.9424831

Molar Refractivity

50.3897

Polarizability

20.07057

Polar Surface Area

39.44

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

7H-furo[3,2-g][1]benzopyran-7-onePsoralenFuro[3,2-g]coumarin7H-Furo[3,2-g]benzopyran-7-onePsoralenPsoraleneFicusinFuro[4',5':6,7]coumarinFurocoumarinFuro[2',3':7,6]coumarinNSC 4045623-(6-Hydroxy-5-benzofuranyl)-2-propenoic Acid δ-Lactone6,7-Furanocoumarin7H-Furo[3,2-g][1]benzopyran-7-one

IUPAC Traditional name

psoralen 7H-furo[3,2-g]chromen-7-one

IUPAC name

7H-furo[3,2-g]chromen-7-one

Names and Identifiers

Registration numbers

CHEMBL

CHEBI ID

Chemspider ID

Wikipedia Title

CAS Number

Beilstein Number

EC Number

MDL Number

PubChem SID

PubChem CID

Registration numbers

Properties

Product Information

Purity

≥99%

≥99.0% (HPLC)

99.0

Empirical Formula (Hill Notation)

C11H6O3

Grade

for fluorescence

Certificate of Analysis

Download link

This takes advantage of the high UV absorbance of psoralen

An important use of psoralen is in PUVA treatment for skin problems such as psoriasis and (to a lesser extent) eczema and vitiligo.

From Psoralea corylifolia, Ficus salicifolia, Heracleum leskovii, Ruta chalepensis, Dictamnus hispanicus, etc. Found in common vegetables, e.g. parsnip, celery esp. if diseased or `spoiled'

Pharmacology Properties

Mechanism of Action

Radiosensitizer

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

P8399

Application
Photochemical reagent for the investigation of nucleic acid structure and function.1,2,3,4
Biochem/physiol Actions
Phototoxic phytoalexin; when activated by UV light, psoralen induces interstrand cross-links in DNA.

82548

Application
Photochemical reagent for the investigation of nucleic acid structure and function.1,2,3,4

Wikipedia

Psoralen

TRC

P839800

Psoralens are phytoalexins; they are used by plants in a defensive response to attacks by fungi and insects. They have also shown photosensitizing and phototoxic effects in animals and humans and have been used in photochemotherapy for management of vitil

Molecule Details

References

PubChem Literature

From Data Sources

• Parsons, B.J., et al.: Photochem. Photobiol., 32, 813 (1980)

• Ceska, O. et al., Experientia, 1986, 42, 1302, (occur, tox)

• Zubia, E. et al., Tetrahedron, 1992, 48, 4239, (synth)

• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (rev)

• Hayakawa, K. et al., J.A.C.S., 1984, 106, 6735, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FQD000

• Chatterjee, A. et al., Indian J. Chem., Sect. B, 1977, 15, 212, (synth, uv, pmr)

• Worden, L.R. et al., J.O.C., 1969, 34, 2311, (synth)

• Matsumoto, H. et al., Chem. Pharm. Bull., 1978, 26, 3433, (uv)

• Reisch, J. et al., Chem. Ber., 1979, 112, 1491, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 173A, (nmr)

• Bergenthal, D. et al., Arch. Pharm. (Weinheim, Ger.), 1978, 311, 1026, (cmr)

• Pardanani, N.H. et al., Aust. J. Chem., 1972, 25, 1537, (synth)

• Austin, D.H. et al., Phytochemistry, 1973, 12, 1657, (biosynth)

• Beier, R.C. et al., Xenobiotics in Foods and Feeds, Amer. Chem. Soc., 1983, 295, (occur)

• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (isol, uv, pmr, cmr)

• Chimichi, S. et al., Tetrahedron, 2002, 58, 4859-4863, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

psoralen 7H-furo[3,2-g]chromen-7-one

IUPAC name

7H-furo[3,2-g]chromen-7-one

Registration numbers

CHEMBL

CHEBI ID

Chemspider ID

Wikipedia Title

CAS Number

Beilstein Number

EC Number

MDL Number

PubChem SID

PubChem CID

Molecule Details

P8399

82548

Application
Photochemical reagent for the investigation of nucleic acid structure and function.1,2,3,4

Wikipedia

Psoralen

TRC

P839800

References

PubChem Literature

From Data Sources

• Parsons, B.J., et al.: Photochem. Photobiol., 32, 813 (1980)

• Ceska, O. et al., Experientia, 1986, 42, 1302, (occur, tox)

• Zubia, E. et al., Tetrahedron, 1992, 48, 4239, (synth)

• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (rev)

• Hayakawa, K. et al., J.A.C.S., 1984, 106, 6735, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FQD000

• Chatterjee, A. et al., Indian J. Chem., Sect. B, 1977, 15, 212, (synth, uv, pmr)

• Worden, L.R. et al., J.O.C., 1969, 34, 2311, (synth)

• Matsumoto, H. et al., Chem. Pharm. Bull., 1978, 26, 3433, (uv)

• Reisch, J. et al., Chem. Ber., 1979, 112, 1491, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 173A, (nmr)

• Bergenthal, D. et al., Arch. Pharm. (Weinheim, Ger.), 1978, 311, 1026, (cmr)

• Pardanani, N.H. et al., Aust. J. Chem., 1972, 25, 1537, (synth)

• Austin, D.H. et al., Phytochemistry, 1973, 12, 1657, (biosynth)

• Beier, R.C. et al., Xenobiotics in Foods and Feeds, Amer. Chem. Soc., 1983, 295, (occur)

• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (isol, uv, pmr, cmr)

• Chimichi, S. et al., Tetrahedron, 2002, 58, 4859-4863, (synth)

Bioactivity

PubChem BioAssay

Properties

Product Information

Purity

≥99%

≥99.0% (HPLC)

99.0

Empirical Formula (Hill Notation)

C11H6O3

Grade

for fluorescence

Certificate of Analysis

Download link

This takes advantage of the high UV absorbance of psoralen

An important use of psoralen is in PUVA treatment for skin problems such as psoriasis and (to a lesser extent) eczema and vitiligo.

From Psoralea corylifolia, Ficus salicifolia, Heracleum leskovii, Ruta chalepensis, Dictamnus hispanicus, etc. Found in common vegetables, e.g. parsnip, celery esp. if diseased or `spoiled'

Pharmacology Properties

Mechanism of Action

Radiosensitizer

Molecule

ID:129171