Bergamottin

Not to be confused with bergamotene.
Bergamottin
Skeletal formula of bergamottin
Ball-and-stick model of the bergamottin molecule
Names
Preferred IUPAC name
4-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g][1]benzopyran-7-one
Other names
Bergamotine
5-Geranoxypsoralen
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.166.792 Edit this at Wikidata
UNII
  • InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+ checkY
    Key: DBMJZOMNXBSRED-OQLLNIDSSA-N checkY
  • InChI=1/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
    Key: DBMJZOMNXBSRED-OQLLNIDSBR
  • CC(=CCC/C(=C/COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/C)C
Properties
C21H22O4
Molar mass 338.403 g·mol−1
Melting point 55 to 56 °C (131 to 133 °F; 328 to 329 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bergamottin (5-geranoxypsoralen) is a natural furanocoumarin found in the pulp of pomelos and grapefruits.[1] It is also found in the peel and pulp of the bergamot orange, from which it was first isolated and from which its name is derived.

  1. ^ 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.