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

• ChemBase ID: 129171
• Molecular Formular: C11H6O3
• Molecular Mass: 186.16354
• Monoisotopic Mass: 186.03169405
• SMILES: O=c1oc2cc3occc3cc2cc1
• Canonical SMILES: O=c1ccc2c(o1)cc1c(c2)cco1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: psoralen; 7H-furo[3,2-g]chromen-7-one
• Synonyms: 7H-furo[3,2-g][1]benzopyran-7-one; Psoralen; 7H-Furo[3,2-g][1]benzopyran-7-one; Furocoumarin; 3-(6-Hydroxy-5-benzofuranyl)-2-propenoic Acid δ-Lactone; 6,7-Furanocoumarin; Ficusin; Furo[2',3':7,6]coumarin; Furo[4',5':6,7]coumarin; NSC 404562; Psoralene; 7H-Furo[3,2-g]benzopyran-7-one; Furo[3,2-g]coumarin; Psoralen

Database IDs

• CAS Number: 66-97-7
• EC Number: 200-639-7
• MDL Number: MFCD00010520
• Beilstein Number: 152784
• PubChem SID: 24898918; 162223468
• PubChem CID: 6199
• CHEBI ID: 27616
• CHEMBL: 164660
• Chemspider ID: 5964
• Wikipedia Title: Psoralen

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9424831
• LogD (pH = 7.4): 1.9424831
• Log P: 1.9424831
• Molar Refractivity: 50.3897 cm^3
• Polarizability: 20.07057 Å^3
• Polar Surface Area: 39.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid; Powder
• Melting Point: 158–161 °C; 160-162 °C; 163-164°C
• Fluorescence: λex 335 nm; λem 460 nm (pH 7.0)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: LV0944000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Radiosensitizer

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 99.0
• Grade: for fluorescence
• Biological Source: 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'
• Application(s): An important use of psoralen is in PUVA treatment for skin problems such as psoriasis and (to a lesser extent) eczema and vitiligo.; This takes advantage of the high UV absorbance of psoralen
• Empirical Formula (Hill Notation): C11H6O3

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.

Sigma Aldrich - 82548

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

Toronto Research Chemicals - 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

REFERENCES

• Parsons, B.J., et al.: Photochem. Photobiol., 32, 813 (1980)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 173A, (nmr)
• Worden, L.R. et al., J.O.C., 1969, 34, 2311, (synth)
• Pardanani, N.H. et al., Aust. J. Chem., 1972, 25, 1537, (synth)
• Austin, D.H. et al., Phytochemistry, 1973, 12, 1657, (biosynth)
• Chatterjee, A. et al., Indian J. Chem., Sect. B, 1977, 15, 212, (synth, uv, pmr)
• Bergenthal, D. et al., Arch. Pharm. (Weinheim, Ger.), 1978, 311, 1026, (cmr)
• Matsumoto, H. et al., Chem. Pharm. Bull., 1978, 26, 3433, (uv)
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• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (rev)
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• Ceska, O. et al., Experientia, 1986, 42, 1302, (occur, tox)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FQD000