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 D05BA03 (WHO)
Identifiers
CAS Number 484-20-8 YesY
PubChem (CID) 2355
ChemSpider 2265 YesY
UNII 4FVK84C92X YesY
KEGG D07521 YesY
ChEBI CHEBI:18293 N
ChEMBL CHEMBL24171 YesY
Chemical and physical data
Formula C12H8O4
Molar mass 216.19 g/mol
3D model (Jmol) Interactive image
 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. doi:10.3358/shokueishi.49.326. PMID 18787320. 
  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. doi:10.1021/ja01625a055. ISSN 0002-7863.