1.0 2010-04-08 22:10:06 UTC 2019-11-26 03:06:32 UTC FDB012300 Auraptene Isolated from Citrus aurantium (Seville orange) and bael fruit (Aegle marmelos) 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. The effect in humans is not yet known. Auraptene is found in many foods, some of which are citrus, fruits, sweet orange, and lemon. 7-([(2E)-3,7-Dimethyl-2,6-octadienyl]oxy)-2H-chromen-2-one 7-(3,7-Dimethyl-2,6-octadienyl)oxy-2H-1-benzopyran-2-one, 9CI 7-[(3,7-Dimethyl-2,6-octadienyl)oxy]-(e)-coumarin 7-Geranyloxycoumarin Aurapten Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)- Feronialactone O-Geranylumbelliferone C19H22O3 298.3762 298.15689457 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one auraptene 495-02-3 CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1 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+ RSDDHGSKLOSQFK-RVDMUPIBSA-N belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Terpene lactones Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aromatic heteropolycyclic compounds 1-benzopyrans Alkyl aryl ethers Aromatic monoterpenoids Benzenoids Bicyclic monoterpenoids Coumarins and derivatives Heteroaromatic compounds Hydrocarbon derivatives Lactones Organic oxides Oxacyclic compounds Pyranones and derivatives 1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Aromatic monoterpenoid Benzenoid Benzopyran Bicyclic monoterpenoid Coumarin Ether Heteroaromatic compound Hydrocarbon derivative Lactone Monoterpenoid Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Pyran Pyranone Terpene lactone logp 5.85 ALOGPS logs -5.14 ALOGPS solubility 2.18e-03 g/l ALOGPS melting_point Mp 68° logp 4.65 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one ChemAxon average_mass 298.3762 ChemAxon mono_mass 298.15689457 ChemAxon smiles CC(C)=CCC\C(C)=C\COC1=CC2=C(C=CC(=O)O2)C=C1 ChemAxon formula C19H22O3 ChemAxon 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+ ChemAxon inchikey RSDDHGSKLOSQFK-RVDMUPIBSA-N ChemAxon polar_surface_area 35.53 ChemAxon refractivity 90.93 ChemAxon polarizability 34.45 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13062 Specdb::CMs 160120 Specdb::MsMs 109110 Specdb::MsMs 109111 Specdb::MsMs 109112 Specdb::MsMs 176499 Specdb::MsMs 176500 Specdb::MsMs 176501 Specdb::MsMs 374638 Specdb::MsMs 451264 Specdb::MsMs 452264 Specdb::MsMs 2391814 Specdb::MsMs 2391815 Specdb::MsMs 2391816 Specdb::MsMs 2570717 Specdb::MsMs 2570718 Specdb::MsMs 2570719 HMDB34054 #<Reference:0x000055ce323ab0c8> #<Reference:0x000055ce323aaf10> Citrus Unknown generic Fruits Unknown generic Lemon Type 1 specific Citrus limon 2708 Sweet orange Type 1 specific Citrus sinensis 2711 Anti peroxidant 519 Anti superoxidogenic 636 Anti-aggregant 94 Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Chemopreventive inhibitor 797 A substance that diminishes the rate of a chemical reaction. Quinone-reductase inducer 1277