Bergapten

Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.

Bergapten
Names
Preferred IUPAC name
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
Other names
  • 5-Methoxypsoralen
  • Bergaptene
  • Heraclin
  • Majudin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.913
EC Number
  • 207-604-5
KEGG
PubChem CID
UNII
UN number 1759
  • 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
    Key: BGEBZHIAGXMEMV-UHFFFAOYSA-N
SMILES
  • COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
Properties
C12H8O4
Molar mass 216.192 g/mol
Pharmacology
D05BA03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bergapten belongs to a class of chemical compounds known as the furanocoumarins. In 1834, Kalbrunner isolated 5-methoxypsoralen from bergamot essential oil, hence the common name "bergapten". It was the first furanocoumarin to be isolated and identified.

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