Bergapten

Title: Bergapten
CAS Registry Number: 484-20-8
CAS Name: 4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
Additional Names: 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. Späth 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. Hönigsmann 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.
Bergenin Bermoprofen Berninamycin Beryllium Acetate Beryllium Acetylacetonate

Bergapten
Bergapten.png
Systematic (IUPAC) name
5-methoxy-2H-furo[3,2-g]chromen-2-one
Clinical data
Legal status  ?
Routes Oral
Identifiers
CAS number 484-20-8 YesY
ATC code D05BA03
PubChem CID 2355
ChemSpider 2265 YesY
UNII 4FVK84C92X YesY
KEGG D07521 YesY
ChEBI CHEBI:18293 N
ChEMBL CHEMBL24171 YesY
Chemical data
Formula C12H8O4 
Mol. mass 216.19 g/mol
 N (what is this?)  (verify)

Bergapten (5-methoxypsoralen) is a psoralen (also known as furocoumarins) found in bergamot essential oil, in other citrus essential oils,[1] and in grapefruit juice.[2] It is the chemical in bergamot oil that causes phototoxicity.[3] Bergapten-free bergamot essential oil or synthetics are now used in perfumery.