2H-furo[2,3-h]chromen-2-one

• ChemBase ID: 125864
• Molecular Formular: C11H6O3
• Molecular Mass: 186.16354
• Monoisotopic Mass: 186.03169405
• SMILES: O=c1oc2c3ccoc3ccc2cc1
• Canonical SMILES: O=c1ccc2c(o1)c1ccoc1cc2
• InChI: InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
• InChIKey: XDROKJSWHURZGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2H-furo[2,3-h]chromen-2-one
• IUPAC Traditional name: 2H-furo[2,3-h]chromen-2-one; angelicin
• Synonyms: Furo[2,3-h]chromen-2-one; Sopsoralen; Furo[5',4':7,8]coumarin; Bakuchicin; 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran; Angelicin; Isopsoralen; Angelicin

Database IDs

• CAS Number: 523-50-2
• MDL Number: MFCD00064930
• PubChem SID: 24890472; 162220209
• PubChem CID: 10658
• CHEBI ID: 28928
• CHEMBL: 53569
• Chemspider ID: 10208
• KEGG ID: C09060
• Wikipedia Title: Angelicin

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: 20.074858 Å^3
• Polar Surface Area: 39.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Powder; White Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: LV0940000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Radiosensitizer

Product Information

• Biological Source: Constit. of roots and leaves of angelica (Angelica archangelica). Found in roots and on surface of parsnips and diseased celery. Also in other Angelica spp, Heracleum spp. and others
• Application(s): Possesses sedative props.

DETAILS

Sigma Aldrich - A0956

Biochem/physiol Actions
Angular furocoumarin with diverse photobiological effects. Upon long-wavelength UV irradiation, forms monoadduct with double-stranded DNA and reacts with unsaturated fatty acids. Inhibits DNA and RNA synthesis and cell replication in Ehrlich ascites tumor cells.

Toronto Research Chemicals - A637575

Antifungal.

REFERENCES

• Sardari, S., et al.: Pharm. Pharmacol. Commun., 6, 455 (2000)
• Barnes, C.S. et al., Aust. J. Chem., 1964, 17, 975, (ms)
• Steck, W. et al., Can. J. Chem., 1969, 47, 2425, (isol)
• Steck, W. et al., Can. J. Biochem., 1970, 48, 872, (biosynth)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1388, (occur)
• Gonzlez, A.G. et al., An. Quim., 1973, 69, 1013, (pmr)
• Reisch, J. et al., Chem. Ber., 1979, 112, 1491, (synth)
• Desai, S.M. et al., Indian J. Chem., Sect. B, 1985, 24, 47, (synth)
• Ceska, O. et al., Experientia, 1986, 42, 1302, (occur, tox)
• Wulff, W.D. et al., J.A.C.S., 1988, 110, 7419, (synth)
• Zubia, E. et al., Tetrahedron, 1992, 48, 4239, (synth)
• McNab, H., J. Chem. Res., Synop., 1995, 116, (Bakuchicin)
• Lee, Y.R., Tetrahedron, 1995, 51, 3087, (synth, pmr)
• Amin, A.S. et al., Pharm. Pharmacol. Commun., 2000, 6, 455-458, (activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FQC000