1157. Bergapten

Nomenclature

CAS number: 484-20-8
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; 5-methoxypsoralen; bergaptan; bergaptene; heraclin; majudin; 5-MOP; Psoraderm-5 (Sunlife).
C12H8O4; mol wt 216.19.
C 66.67%, H 3.73%, O 29.60%.

Description and 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"ath 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"onigsmann 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).

Chemical structure

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.

Use

Has been used to promote tanning in suntan preparations.

Therapeutic Category

Antipsoriatic.

Keywords

Antipsoriatic