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^Y
PubChem (CID)	2355
ChemSpider	2265^Y
UNII	4FVK84C92X^Y
KEGG	D07521^Y
ChEBI	CHEBI:18293^N
ChEMBL	CHEMBL24171^Y
Chemical and physical data
Formula	C₁₂H₈O₄
Molar mass	216.19 g/mol
3D model (Jmol)	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^Y Key:BGEBZHIAGXMEMV-UHFFFAOYSA-N^Y
^NY (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

↑ 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.
↑ 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.

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

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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