Bergapten

Bergapten

Systematic (IUPAC) name
4-methoxy-7H-furo[3,2-g]chromen-7-one
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	484-20-8
ATC code	D05BA03 (WHO)
PubChem	CID 2355
ChemSpider	2265
UNII	4FVK84C92X
KEGG	D07521
ChEBI	CHEBI:18293
ChEMBL	CHEMBL24171
Chemical data
Formula	C12H8O4
Molar mass	216.19 g/mol
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.

References

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 and Giuseppe Calabrò (2004). "Elimination of Furocoumarins in Bergamot Peel Oil". Perfumer & Flavorist 29.