1.0 2010-04-08 22:11:48 UTC 2025-11-19 00:54:26 UTC FDB015354 4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan, also known as 34-divanillyltetrahydrofuran or dv-tetrahydrofuran, is a member of the class of compounds known as 9,9'-epoxylignans. 9,9'-epoxylignans are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan can be found in sesame, which makes 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan a potential biomarker for the consumption of this food product. 4,4'-[(Tetrahydro-3,4-furandiyl)bis(methylene)]bis[2-methoxyphenol], 9CI a,a'-[Tetrahydro-3,4-furandiyl]bis[2-methoxy-p-cresol], 8CI Anhydrosecoisolariciresinol Divanillyltetrahydrofuran Shonanin C20H24O5 344.4016 344.162373878 4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol 3,4-divanillyltetrahydrofuran 34730-78-4 COC1=CC(CC2COCC2CC2=CC(OC)=C(O)C=C2)=CC=C1O InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3 ROGUIJKVZZROIQ-UHFFFAOYSA-N belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). 9,9'-epoxylignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Dialkyl ethers Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Oxacyclic compounds Phenoxy compounds Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 9,9p-epoxylignan Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Dialkyl ether Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Tetrahydrofuran logp 3.13 ALOGPS logs -4.41 ALOGPS solubility 1.35e-02 g/l ALOGPS logp 3.49 ChemAxon pka_strongest_acidic 9.96 ChemAxon pka_strongest_basic -4 ChemAxon iupac 4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol ChemAxon average_mass 344.4016 ChemAxon mono_mass 344.162373878 ChemAxon smiles COC1=CC(CC2COCC2CC2=CC(OC)=C(O)C=C2)=CC=C1O ChemAxon formula C20H24O5 ChemAxon inchi InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3 ChemAxon inchikey ROGUIJKVZZROIQ-UHFFFAOYSA-N ChemAxon polar_surface_area 68.15 ChemAxon refractivity 95.78 ChemAxon polarizability 36.55 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 77859 Specdb::MsMs 77860 Specdb::MsMs 77861 Specdb::MsMs 138087 Specdb::MsMs 138088 Specdb::MsMs 138089 Specdb::MsMs 3605782 Specdb::MsMs 3605783 Specdb::MsMs 3605784 Specdb::MsMs 3606871 Specdb::MsMs 3606872 Specdb::MsMs 3606873 Sesame Type 1 specific Sesamum orientale 4182 0.0 0.0 0.0 mg/100 g