1.0 2010-04-08 22:04:31 UTC 2025-11-18 22:16:58 UTC FDB000326 Isohydroxymatairesinol Isohydroxymatairesinol is a member of the class of compounds known as lignan lactones. Lignan lactones are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Isohydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Isohydroxymatairesinol can be found in sesame, which makes isohydroxymatairesinol a potential biomarker for the consumption of this food product. (+)-Isohydroxymatairesinol C20H22O7 374.3845 374.136553058 (3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-2-one (3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-2-one [H][C@@]1(CO)[C@H](OC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1)C1=CC=C(O)C(OC)=C1 InChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)22)7-13-14(10-21)19(27-20(13)24)12-4-6-16(23)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1 BTXZSJTULWTSJG-BIENJYKASA-N belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Lignan lactones Organic compounds Lignans, neolignans and related compounds Lignan lactones Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 7,9'-epoxylignans Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acid esters Gamma butyrolactones Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Phenoxy compounds Primary alcohols Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 7,9p-epoxylignan Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Ether Furanoid lignan Gamma butyrolactone Hydrocarbon derivative Lactone Lignan lactone Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Primary alcohol Tetrahydrofuran Tetrahydrofuran lignan logp 2.06 ALOGPS logs -4.07 ALOGPS solubility 3.17e-02 g/l ALOGPS logp 2.1 ChemAxon pka_strongest_acidic 9.63 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-2-one ChemAxon average_mass 374.3845 ChemAxon mono_mass 374.136553058 ChemAxon smiles [H][C@@]1(CO)[C@H](OC(=O)[C@]1([H])CC1=CC(OC)=C(O)C=C1)C1=CC=C(O)C(OC)=C1 ChemAxon formula C20H22O7 ChemAxon inchi InChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)22)7-13-14(10-21)19(27-20(13)24)12-4-6-16(23)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1 ChemAxon inchikey BTXZSJTULWTSJG-BIENJYKASA-N ChemAxon polar_surface_area 105.45 ChemAxon refractivity 97.05 ChemAxon polarizability 38.6 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 105879 Specdb::MsMs 105880 Specdb::MsMs 105881 Specdb::MsMs 172494 Specdb::MsMs 172495 Specdb::MsMs 172496 Specdb::MsMs 3597028 Specdb::MsMs 3597029 Specdb::MsMs 3597030 Specdb::MsMs 3597031 Specdb::MsMs 3597032 Specdb::MsMs 3597033 Sesame Type 1 specific Sesamum orientale 4182 1.611 1.610999942 1.610999942 mg/100 g