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

• ChemBase ID: 104315
• Molecular Formular: C12H8O4
• Molecular Mass: 216.18952
• Monoisotopic Mass: 216.04225874
• SMILES: COc1c2ccc(=O)oc2cc2c1cco2
• Canonical SMILES: COc1c2ccc(=O)oc2cc2c1cco2
• InChI: InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
• InChIKey: BGEBZHIAGXMEMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxy-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: 4-methoxy-7H-furo[3,2-g]chromen-7-one; bergapten
• Synonyms: 4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; Bergaptan; Bergaptene; Heraclin; Majudin; 5-MOP, Psoraderm-5; 5-METHOXYPSORALEN; Bergapten; 5-Methoxypsoralen; Bergapten; 4-Methoxyfuro[3,2-g]benzopyrane-7-one; Bergapten; 5-Methoxypsoralen; 4-Methoxy-7H-furo[3,2-g]chromen-7-one; 4-甲氧基-7H-呋喃并[3,2-g]苯并吡喃-7-酮; 佛手柑内酯; 5-甲氧基补骨脂素

Database IDs

• CAS Number: 484-20-8
• EC Number: 207-604-5
• MDL Number: MFCD00010272
• Beilstein Number: 19560
• PubChem SID: 24856667; 162093037; 24883936
• PubChem CID: 2355
• ATC CODE: D05BA03
• CHEMBL: 24171
• Chemspider ID: 2265
• KEGG ID: D07521
• Unique Ingredient Identifier: 4FVK84C92X
• Wikipedia Title: Bergapten

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7848117
• LogD (pH = 7.4): 1.7848117
• Log P: 1.7848117
• Molar Refractivity: 56.8529 cm^3
• Polarizability: 22.595345 Å^3
• Polar Surface Area: 48.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Powder; White to Off-White Solid
• Melting Point: 156-158°C; 189-193 °C; 190-193 °C; 190-193 °C(lit.)
• Fluorescence: λex 352 nm; λem 480 nm in methanol

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: LV1300000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 45-43; R:45
• Safety Statements: 53-36/37-45; S:28-36/37/39-45-53
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H334-H340-H350
• GHS Precautionary statements: P201-P261-P308 + P313
• 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; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Mechanism of Action: Radiosensitizer; Spasmolytic

Product Information

• Purity: ≥98.0% (HPLC); ≥99.0% (HPLC); 95+%; 97%; 99%
• Grade: analytical standard; for fluorescence
• Salt Data: Free Base
• Biological Source: Major constit. of bergamot oil (Citrus bergamia), also from Heracleum giganteum and Ammi majus. Widely distributed in the Rutaceae and Umbelliferae
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antihistamine agent; Antiinflammatory; Antipsoriatic; Show spasmolytic props; Used in the treatment of vitiligo
• Empirical Formula (Hill Notation): C12H8O4

DETAILS

Sigma Aldrich - 275727

Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 65320

Other Notes
Intercalating agent for DNA forming covalent cross-links upon UV-irradiation1,2,3

Toronto Research Chemicals - B318500

Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.

REFERENCES

• Honigsmann, H., et al.: Br. J. Dermatol., 101, 369 (1979)
• Kawaii, S. et al., J. Agric. Food Chem., 1999, 47, 4073, (activity)
• Oliva, A. et al., J. Chem. Ecol., 1999, 25, 519-526, (activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN275
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1321A, (nmr)
• Baetcke, E. et al., Ber., 1912, 45, 3705, (struct)
• Glatfelder, A. et al., Helv. Chim. Acta, 1920, 3, 541; 1921, 4, 718, (synth)
• Socias, L. et al., Ber., 1934, 67, 59, (isol)
• Kubiczek, G. et al., Ber., 1937, 70, 1253, (synth)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1369, (occur, deriv)
• Austin, D.J. et al., Phytochemistry, 1973, 12, 1657, (biosynth)
• Boyd, R.K. et al., Can. J. Chem., 1979, 57, 1995, (ms)
• Duddeck, H. et al., Phytochemistry, 1979, 18, 139, (cmr)
• IARC Monog., 1986, 40, 327, (tox, rev)
• Gu, Z. et al., Chem. Pharm. Bull., 1990, 38, 2498, (deriv)
• Ginderow, D., Acta Cryst. C, 1991, 47, 2144, (cryst struct)
• Diawara, M.M. et al., J. Agric. Food Chem., 1995, 43, 723-727, (occur)
• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (Bergapten, isol, pmr, cmr)