1.0 2010-04-08 22:04:38 UTC 2025-11-18 22:20:19 UTC FDB000610 Isosakuranetin 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is a member of the class of compounds known as 4'-o-methylated flavonoids. 4'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one can be found in sweet orange, which makes 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one a potential biomarker for the consumption of this food product. 2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CI Citrifoliol Isosakuranetin Kikokunetin Ponciretin C16H14O5 286.283 286.084123551 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one isosakuranetin 480-43-3 COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3 HMUJXQRRKBLVOO-UHFFFAOYSA-N belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. 4'-O-methylated flavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids O-methylated flavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Anisoles Aryl alkyl ketones Chromones Flavanones Hydrocarbon derivatives Methoxybenzenes Organic oxides Oxacyclic compounds Phenoxy compounds Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4p-methoxyflavonoid-skeleton 5-hydroxyflavonoid 7-hydroxyflavonoid Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Flavan Flavanone Hydrocarbon derivative Hydroxyflavonoid Ketone Methoxybenzene Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol ether Phenoxy compound Vinylogous acid logp 2.95 ALOGPS logs -3.51 ALOGPS solubility 8.79e-02 g/l ALOGPS logp 2.98 ChemAxon pka_strongest_acidic 7.87 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 286.283 ChemAxon mono_mass 286.084123551 ChemAxon smiles COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C16H14O5 ChemAxon inchi InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3 ChemAxon inchikey HMUJXQRRKBLVOO-UHFFFAOYSA-N ChemAxon polar_surface_area 75.99 ChemAxon refractivity 75.77 ChemAxon polarizability 29.42 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5928 Specdb::CMs 54460 Specdb::CMs 129794 Specdb::CMs 167678 Specdb::CMs 917889 Specdb::CMs 917890 Specdb::CMs 917891 Specdb::CMs 917892 Specdb::CMs 917893 Specdb::MsMs 84882 Specdb::MsMs 84883 Specdb::MsMs 84884 Specdb::MsMs 146847 Specdb::MsMs 146848 Specdb::MsMs 146849 Specdb::MsMs 2235687 Specdb::MsMs 2237667 Specdb::MsMs 2237855 Specdb::MsMs 2239731 Specdb::MsMs 2239852 Specdb::MsMs 2241844 Specdb::MsMs 2241906 Specdb::MsMs 2243971 Specdb::MsMs 2248431 Specdb::MsMs 2249933 Specdb::MsMs 2250291 Specdb::MsMs 2252085 Specdb::MsMs 2693624 Specdb::MsMs 2693625 Specdb::MsMs 2693626 Specdb::MsMs 2985029 Specdb::MsMs 2985030 Specdb::MsMs 2985031 Sweet orange Type 1 specific Citrus sinensis 2711