Bergapten

Bergapten
Clinical data
Routes of; administration	Oral
ATC code	D05BA03 (WHO) ;
Identifiers
	IUPAC name 4-methoxy-7H-furo[3,2-g]chromen-7-one;
CAS Number	484-20-8 ;
PubChem CID	2355;
ChemSpider	2265 ;
UNII	4FVK84C92X;
KEGG	D07521 ;
ChEBI	CHEBI:18293 ;
ChEMBL	ChEMBL24171 ;
CompTox Dashboard (EPA)	DTXSID1025560 ;
ECHA InfoCard	100.006.913
Chemical and physical data
Formula	C12H8O4
Molar mass	216.19 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\1Oc3c(/C=C/1)c(OC)c2ccoc2c3;
	InChI 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 ;
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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

^ 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.
^ 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.
^ Francesco Gionfriddo; Enrico Postorino; Giuseppe Calabrò (2004). "Elimination of Furocoumarins in Bergamot Peel Oil". Perfumer & Flavorist. 29. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
^ 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.

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