1.0 2010-04-08 22:07:33 UTC 2025-11-18 23:04:36 UTC FDB007325 8-Methoxycirsilineol 8-methoxycirsilineol, also known as 4',5-dihydroxy-3',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 8-methoxycirsilineol is considered to be a flavonoid lipid molecule. 8-methoxycirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 8-methoxycirsilineol can be found in common thyme and mandarin orange (clementine, tangerine), which makes 8-methoxycirsilineol a potential biomarker for the consumption of these food products. C19H18O8 374.3414 374.100167552 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one 8-methoxycirsilineol COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1 InChI=1S/C19H18O8/c1-23-13-7-9(5-6-10(13)20)12-8-11(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3 UBZBPKARIHPOEC-UHFFFAOYSA-N belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. 8-O-methylated flavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids O-methylated flavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 3'-O-methylated flavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 6-O-methylated flavonoids 7-O-methylated flavonoids Alkyl aryl ethers Anisoles Chromones Flavones Heteroaromatic compounds Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Organic oxides Oxacyclic compounds Phenoxy compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 3p-methoxyflavonoid-skeleton 4'-hydroxyflavonoid 5-hydroxyflavonoid 6-methoxyflavonoid-skeleton 7-methoxyflavonoid-skeleton 8-methoxyflavonoid-skeleton Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Ether Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Pyran Pyranone Vinylogous acid Flavones and Flavonols logp 2.50 ALOGPS logs -3.89 ALOGPS solubility 4.86e-02 g/l ALOGPS logp 2.38 ChemAxon pka_strongest_acidic 8.39 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one ChemAxon average_mass 374.3414 ChemAxon mono_mass 374.100167552 ChemAxon smiles COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1 ChemAxon formula C19H18O8 ChemAxon inchi InChI=1S/C19H18O8/c1-23-13-7-9(5-6-10(13)20)12-8-11(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3 ChemAxon inchikey UBZBPKARIHPOEC-UHFFFAOYSA-N ChemAxon polar_surface_area 103.68 ChemAxon refractivity 96.79 ChemAxon polarizability 37.65 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 66861 Specdb::MsMs 66862 Specdb::MsMs 66863 Specdb::MsMs 124542 Specdb::MsMs 124543 Specdb::MsMs 124544 Specdb::CMs 77561 Common thyme Type 1 specific Thymus vulgaris 49992 0.74 0.74 0.74 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 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-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose.