1.0 2010-04-08 22:12:35 UTC 2025-11-19 01:49:13 UTC FDB016702 Cirsilineol Cirsilineol, also known as 4',5-dihydroxy-3',6,7-trimethoxy-flavone or anisomelin, 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, cirsilineol is considered to be a flavonoid lipid molecule. Cirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsilineol can be found in a number of food items such as common thyme, tarragon, common sage, and hyssop, which makes cirsilineol a potential biomarker for the consumption of these food products. Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes . 4',5-Dihydroxy-3',6,7-trimethoxyflavone Anisomelin Cirsilineol Cirsilineol (5,4'-dihydroxy-6,7,3'-trimethoxyflavone) Eupatrin Fastigenin C18H16O7 344.3154 344.089602866 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one cirsilineol 41365-32-6 COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 VKOSQMWSWLZQPA-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'-O-methylated flavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 6-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 1-hydroxy-4-unsubstituted benzenoid 3p-methoxyflavonoid-skeleton 4'-hydroxyflavonoid 5-hydroxyflavonoid 6-methoxyflavonoid-skeleton 7-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 Flavones and Flavonols dihydroxyflavone flavones trimethoxyflavone logp 2.93 ALOGPS logs -3.86 ALOGPS solubility 4.75e-02 g/l ALOGPS melting_point Mp 208-210° (203°) logp 2.54 ChemAxon pka_strongest_acidic 8.87 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one ChemAxon average_mass 344.3154 ChemAxon mono_mass 344.089602866 ChemAxon smiles COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC ChemAxon formula C18H16O7 ChemAxon inchi InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 ChemAxon inchikey VKOSQMWSWLZQPA-UHFFFAOYSA-N ChemAxon polar_surface_area 94.45 ChemAxon refractivity 90.32 ChemAxon polarizability 34.94 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 52050 Specdb::MsMs 52051 Specdb::MsMs 52052 Specdb::MsMs 152268 Specdb::MsMs 152269 Specdb::MsMs 152270 Specdb::MsMs 3606054 Specdb::MsMs 3606055 Specdb::MsMs 3606056 Specdb::MsMs 3606057 Specdb::MsMs 3606058 Common sage Type 1 specific Salvia officinalis 38868 Common thyme Type 1 specific Thymus vulgaris 49992 Hyssop Type 1 specific Hyssopus officinalis 39324 Lemon verbena Type 1 specific Aloysia triphylla 542672 19.100714 19.100714224 19.100714224 mg/100 g Tarragon Type 1 specific Artemisia dracunculus 72341 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-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Cyclooxygenase-1 inhibitor 840 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1. Cyclooxygenase-2 inhibitor 841 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. Parasiticide 1198 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Plasmodicide 1233