Title: Bergapten
CAS Registry Number: 484-20-8
CAS Name: 4-Methoxy-7
H-furo[3,2-
g][1]benzopyran-7-one
Synonyms: 5-methoxypsoralen; bergaptan; bergaptene; heraclin; majudin; 5-MOP
Trademarks: Psoraderm-5 (Sunlife)
Molecular Formula: C12H8O4
Molecular Weight: 216.19
Percent Composition: C 66.67%, H 3.73%, O 29.60%
Literature References: Naturally occurring analog of psoralen and isomer of methoxsalen,
q.q.v., found in a wide variety of plants. It was first isolated from oil of bergamot from
Citrus bergamia Risso,
Aurantiodiae: Pomeranz,
Monatsh. Chem. 12, 379 (1891),
14, 28 (1893). Isoln from
Fagara xanthoxyloides Lam.,
Rutaceae: H. Thoms, E. Baetcke,
Ber. 44, 3326 (1911);
45, 3705 (1912). Synthesis: E. Sp?th
et al., Ber. 70, 478 (1937); W. N. Howell, R. Robertson,
J. Chem. Soc. 1937, 293; G. Caporale,
Farmaco Ed. Sci. 13, 784 (1958); V. K. Ahluwalia
et al., Indian J. Chem. 7, 831 (1969). Use in photochemotherapy of psoriasis: H. H?nigsmann
et al., Br. J. Dermatol. 101, 369 (1979). Mutagenicity studies: B. R. Scott
et al., Mutat. Res. 39, 29 (1976); M. J. Ashwood-Smith
et al., Nature 285, 407 (1980). Phototoxicity study: A. Kornhauser
et al., Science 217, 733 (1982).
Properties: Needles from alcohol, mp 188° (sublimes). Practically insol in boiling water. Slightly sol in glacial acetic acid, chloroform, benzene, warm phenol. Sol in abs alcohol: 1 part in 60. Its soln in sulfuric acid is yellow-gold.
Melting point: mp 188° (sublimes)
Use: Has been used to promote tanning in suntan preparations.
Therap-Cat: Antipsoriatic.
Keywords: Antipsoriatic.