Auraptene

Auraptene

Names
IUPAC name 7-((E)-3, 7-Dimethylocta-2, 6-dienyloxy)-2H-chromen-2-one
Other names Aurapten 7-Geranyloxycoumarin
Identifiers
CAS Registry Number	495-02-3 N
ChEMBL	ChEMBL307341 Y
ChemSpider	1267148 Y
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+ Y Key: RSDDHGSKLOSQFK-RVDMUPIBSA-N Y 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
Jmol-3D images	Image
PubChem	1550607
SMILES O=C/2Oc1cc(OC\C=C(/C)CC\C=C(/C)C)ccc1\C=C\2
Properties
Molecular formula	C19H22O3
Molar mass	298.38 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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

Auraptene has shown a remarkable effect in the prevention of degenerative diseases. Many studies have reported the effect of auraptene as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models.^[1] The effect in humans is not yet known.

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.