Bergapten

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Bergapten

Systematic (IUPAC) name
5-methoxy-2H-furo[3,2-g]chromen-2-one
Clinical data
Legal status	?
Routes	Oral
Identifiers
CAS number	484-20-8^Y
ATC code	D05BA03
PubChem	CID 2355
ChemSpider	2265^Y
UNII	4FVK84C92X^Y
KEGG	D07521^Y
ChEMBL	CHEMBL24171^Y
Chemical data
Formula	C₁₂H₈O₄
Mol. 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^Y Key:BGEBZHIAGXMEMV-UHFFFAOYSA-N^Y
Y (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.

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

Topical

Tars	Tar / Coal tar^#

Antracens	Dithranol^#

Psoralens	Trioxysalen Methoxsalen

Other	Fumaric acid vitamin D (Calcipotriol Calcipotriol/betamethasone Calcitriol Tacalcitol) Tazarotene

Systemic

Psoralens	Trioxysalen Methoxsalen Bergapten

Retinoids	Etretinate Acitretin

anat/phys/devp

noco (i/b/d/q/u/r/p/m/k/v/f)/cong/tumr (n/e/d), sysi/epon

proc, drug (D2/3/4/5/8/11)

Types of coumarins

O-Methylated	Fraxetin Herniarin (7-O-Methylumbelliferone) Osthol Scopoletin (6-Methoxyumbelliferone)

derivatives

Aglycones

O-Methylated	Bergapten (5-methoxypsoralen) Isopimpinellin (5,8-Dimethoxypsoralene) Methoxsalen (8-Methoxypsoralen) Trioxsalen (2,5,9-Trimethylpsoralen)

Furanocoumarin glycosides

Meroterpene furanocoumarin ether

Oligomers

Synthetic

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