Bergapten

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Bergapten
Bergapten.png
Bergapten (5-methoxypsoralen) - 3D - Ball-and-stick Model.png
Clinical data
Routes of
administration
Oral
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.006.913
Chemical and physical data
Formula C12H8O4
Molar mass 216.19 g/mol
3D model (JSmol)
 NYesY (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.

A known use of bergapten is in the synthesis of Fraxinol.[4]

References[edit]

  1. ^ Calvarano I.; Calvarano M.; Gionfriddo F.; Bovalo F.; Postorino E. (1995). "HPLC profile of citrus essential oils from different species and geographic origin". Essenze Derivati agrumari. 65: 488–502. 
  2. ^ Sakamaki N.; Nakazato M.; Matsumoto H.; Hagino K.; Hirata K.; Ushiyama H. (2008). "Contents of furanocoumarins in grapefruit juice and health foods". Journal of the Food Hygienic Society of Japan. 49 (4): 326–331. PMID 18787320. doi:10.3358/shokueishi.49.326. 
  3. ^ Francesco Gionfriddo; Enrico Postorino & Giuseppe Calabrò (2004). "Elimination of Furocoumarins in Bergamot Peel Oil". Perfumer & Flavorist. 29. 
  4. ^ Schönberg, Alexander; Badran, Nasry; Starkowsky, Nicolas A. (1955). "Furo-chromones and -Coumarins. XII. Synthesis of Fraxinol from Bergapten and of Baicalein from Visnagin". Journal of the American Chemical Society. 77 (20): 5390–5392. ISSN 0002-7863. doi:10.1021/ja01625a055.