1.0 2010-04-08 22:14:55 UTC 2025-11-19 02:29:16 UTC FDB020276 Trachelogenin Trachelogenin is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Trachelogenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Trachelogenin can be found in burdock and grape wine, which makes trachelogenin a potential biomarker for the consumption of these food products. (-)-Trachelogenin 2(3H)-Furanone, dihydro-3-hydroxy-3-vanillyl-4-veratryl- Trachelogenin C21H24O7 388.4111 388.152203122 4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one 4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one 34209-69-3 COC1=CC(CC2(O)C(CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC=C1O InChI=1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3 YFVZKLQNMNKWSB-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Dibenzylbutyrolactone lignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acid esters Dimethoxybenzenes Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Phenoxy compounds Tertiary alcohols Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Dimethoxybenzene Ether Gamma butyrolactone Hydrocarbon derivative Lactone Lignan lactone Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety O-dimethoxybenzene Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Tertiary alcohol Tetrahydrofuran logp 2.60 ALOGPS logs -4.05 ALOGPS solubility 3.47e-02 g/l ALOGPS melting_point Mp 139-141° logp 2.58 ChemAxon pka_strongest_acidic 9.94 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac 4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one ChemAxon average_mass 388.4111 ChemAxon mono_mass 388.152203122 ChemAxon smiles COC1=CC(CC2(O)C(CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC=C1O ChemAxon formula C21H24O7 ChemAxon inchi InChI=1S/C21H24O7/c1-25-17-7-5-13(9-19(17)27-3)8-15-12-28-20(23)21(15,24)11-14-4-6-16(22)18(10-14)26-2/h4-7,9-10,15,22,24H,8,11-12H2,1-3H3 ChemAxon inchikey YFVZKLQNMNKWSB-UHFFFAOYSA-N ChemAxon polar_surface_area 94.45 ChemAxon refractivity 101.57 ChemAxon polarizability 39.65 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1286815 Specdb::MsMs 1286816 Specdb::MsMs 1286817 Specdb::MsMs 1401613 Specdb::MsMs 1401614 Specdb::MsMs 1401615 Specdb::MsMs 3606538 Specdb::MsMs 3606539 Specdb::MsMs 3606540 Specdb::MsMs 3607591 Specdb::MsMs 3607592 Specdb::MsMs 3607593 Burdock Type 1 specific Arctium lappa 4217 Grape wine Type 2 specific 0.0 0.0 0.0 mg/100 g Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti hypertensive 352 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti topoisomerase-II 661 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. Anti-integrase 374 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Anti-lymphomic 414 Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Cardiac 764 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Cytostatic 858 HIV-reverse-transcriptase inhibitor 994 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. 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. Topoisomerase inhibitor 1370 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.