Bergapten

Bergapten
Names
	Preferred IUPAC name 4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
	Other names 5-Methoxypsoralen; Bergaptene; Heraclin; Majudin;
Identifiers
CAS Number	484-20-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18293;
ChEMBL	ChEMBL24171;
ChemSpider	2265;
ECHA InfoCard	100.006.913
EC Number	207-604-5;
KEGG	D07521;
PubChem CID	2355;
UNII	4FVK84C92X;
UN number	1759
CompTox Dashboard (EPA)	DTXSID1025560 ;
	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;
	SMILES COC1=C2C=CC(=O)OC2=CC3=C1C=CO3;
Properties
Chemical formula	C12H8O4
Molar mass	216.192 g/mol
Pharmacology
ATC code	D05BA03 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae.^[1]^[2] In the family Rutaceae, various Citrus species contain significant amounts of bergapten,^[3] especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.

Bergapten belongs to a class of chemical compounds known as the furanocoumarins. In 1834, Kalbrunner isolated 5-methoxypsoralen from bergamot essential oil,^[4] hence the common name "bergapten". It was the first furanocoumarin to be isolated and identified.

^ Nielsen, B. E. (1970). Coumarins of Umbelliferous plants. Copenhagen: Royal Danish School of Pharmacy. Cited by Mitchell and Rook (1979).
^ Mitchell, John; Rook, Arthur (1979). Botanical Dermatology: Plants and Plant Products Injurious to the Skin. Vancouver: Greengrass. pp. 692–699.
^ Dugrand-Judek, Audray; Olry, Alexandre; Hehn, Alain; Costantino, Gilles; Ollitrault, Patrick; Froelicher, Yann; Bourgaud, Frédéric (November 2015). "The Distribution of Coumarins and Furanocoumarins in Citrus Species Closely Matches Citrus Phylogeny and Reflects the Organization of Biosynthetic Pathways". PLOS ONE. 10 (11): e0142757. Bibcode:2015PLoSO..1042757D. doi:10.1371/journal.pone.0142757. PMC 4641707. PMID 26558757.
^ Scott, B. R.; Pathak, M. A.; Mohn, G. R. (1976). "Molecular and genetic basis of furocoumarin reactions". Mutat Res. 39 (1): 29–74. doi:10.1016/0165-1110(76)90012-9. PMID 13299. Archived from the original on 2019-08-11. Retrieved 2019-01-02.

[Nielsen_1970-1] Nielsen, B. E. (1970). Coumarins of Umbelliferous plants. Copenhagen: Royal Danish School of Pharmacy. Cited by Mitchell and Rook (1979).

[Mitchell_and_Rook_1979-2] Mitchell, John; Rook, Arthur (1979). Botanical Dermatology: Plants and Plant Products Injurious to the Skin. Vancouver: Greengrass. pp. 692–699.

[Dugrand-Judek_et_al._2015-3] Dugrand-Judek, Audray; Olry, Alexandre; Hehn, Alain; Costantino, Gilles; Ollitrault, Patrick; Froelicher, Yann; Bourgaud, Frédéric (November 2015). "The Distribution of Coumarins and Furanocoumarins in Citrus Species Closely Matches Citrus Phylogeny and Reflects the Organization of Biosynthetic Pathways". PLOS ONE. 10 (11): e0142757. Bibcode:2015PLoSO..1042757D. doi:10.1371/journal.pone.0142757. PMC 4641707. PMID 26558757.

[Scott_et_al._1976-4] Scott, B. R.; Pathak, M. A.; Mohn, G. R. (1976). "Molecular and genetic basis of furocoumarin reactions". Mutat Res. 39 (1): 29–74. doi:10.1016/0165-1110(76)90012-9. PMID 13299. Archived from the original on 2019-08-11. Retrieved 2019-01-02.

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