Auraptene

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

Auraptene

Names
IUPAC name 7-((E)-3, 7-Dimethylocta-2, 6-dienyloxy)-2H-chromen-2-one
Other names Aurapten 7-Geranyloxycoumarin
Identifiers
CAS Number	495-02-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:134355
ChEMBL	ChEMBL307341
ChemSpider	1267148
PubChem CID	1550607
UNII	F79I1ZEL2E
CompTox Dashboard (EPA)	DTXSID80897576
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+ Key: RSDDHGSKLOSQFK-RVDMUPIBSA-N 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
SMILES 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

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.

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.