1.0 2010-04-08 22:12:35 UTC 2025-11-19 01:49:12 UTC FDB016700 Cirsiliol Cirsiliol, also known as 3',4',5-trihydroxy-6,7-dimethoxyflavone or 6,7-dimethoxy-5,3',4'-trihydroxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsiliol is considered to be a flavonoid lipid molecule. Cirsiliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsiliol can be found in common sage and lemon verbena, which makes cirsiliol a potential biomarker for the consumption of these food products. 3',4',5-Trihydroxy-6,7-dimethoxyflavone 6,7-Dimethoxy-5,3',4'-trihydroxyflavone Cirsiliol C17H14O7 330.2889 330.073952802 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one cirsiliol 34334-69-5 COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3 IMEYGBIXGJLUIS-UHFFFAOYSA-N belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. 7-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 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 6-O-methylated flavonoids Alkyl aryl ethers Anisoles Benzene and substituted derivatives Catechols Chromones Flavones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 6-methoxyflavonoid-skeleton 7-methoxyflavonoid-skeleton Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Ether Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Vinylogous acid Flavones and Flavonols Flavones and Flavonols dimethoxyflavone flavones trihydroxyflavone logp 3.05 ALOGPS logs -3.73 ALOGPS solubility 6.15e-02 g/l ALOGPS melting_point Mp 285-287° (280°) logp 2.39 ChemAxon pka_strongest_acidic 8.57 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one ChemAxon average_mass 330.2889 ChemAxon mono_mass 330.073952802 ChemAxon smiles COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1OC ChemAxon formula C17H14O7 ChemAxon inchi InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3 ChemAxon inchikey IMEYGBIXGJLUIS-UHFFFAOYSA-N ChemAxon polar_surface_area 105.45 ChemAxon refractivity 85.84 ChemAxon polarizability 32.84 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 115663 Specdb::CMs 130107 Specdb::CMs 863406 Specdb::CMs 863407 Specdb::CMs 863408 Specdb::CMs 863409 Specdb::CMs 863410 Specdb::CMs 863411 Specdb::CMs 863412 Specdb::CMs 863413 Specdb::CMs 863414 Specdb::CMs 863415 Specdb::CMs 863416 Specdb::CMs 863417 Specdb::CMs 863418 Specdb::CMs 863419 Specdb::MsMs 108978 Specdb::MsMs 108979 Specdb::MsMs 108980 Specdb::MsMs 176316 Specdb::MsMs 176317 Specdb::MsMs 176318 Specdb::MsMs 3424409 Specdb::MsMs 3424410 Specdb::MsMs 3424411 Specdb::MsMs 3424412 Specdb::MsMs 3424413 Common sage Type 1 specific Salvia officinalis 38868 Lemon verbena Type 1 specific Aloysia triphylla 542672 Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). Anti leukotriene 399 A substance that diminishes the rate of a chemical reaction. Lipoxygenase inhibitor 1077 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.