Auraptene

Auraptene
Names
Preferred IUPAC name
7-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-2H-1-benzopyran-2-one
Other names
Aurapten
7-Geranyloxycoumarin
Identifiers
CAS Number
  • 495-02-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:134355 ☒N
ChEMBL
  • ChEMBL307341 checkY
ChemSpider
  • 1267148 checkY
PubChem CID
  • 1550607
UNII
  • F79I1ZEL2E checkY
CompTox Dashboard (EPA)
  • DTXSID80897576 Edit this at Wikidata
InChI
  • InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+ checkY
    Key: RSDDHGSKLOSQFK-RVDMUPIBSA-N checkY
  • InChI=1/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
    Key: RSDDHGSKLOSQFK-RVDMUPIBBL
  • O=C/2Oc1cc(OC\C=C(/C)CC\C=C(/C)C)ccc1\C=C\2
Properties
Chemical formula
 C19H22O3
Molar mass 298.376 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Auraptene is a natural bioactive monoterpene coumarin ether. It was first isolated from members of the genus Citrus.

Auraptene has shown some effect as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models.[1]

See also

  • C19H22O3

References

  1. ^ Curini, M., Carvotto, G., Epifano, F. and Giannone, G. "Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins"(2006). Current Medicinal Chemistry, 13, 199-222.