1.0 2010-04-08 22:04:31 UTC 2019-11-26 02:54:38 UTC FDB000325 7-Hydroxymatairesinol 7-hydroxymatairesinol 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. 7-hydroxymatairesinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-hydroxymatairesinol can be found in sesame, which makes 7-hydroxymatairesinol a potential biomarker for the consumption of this food product. Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro . (-)-7-Hydroxymatairesinol C20H22O7 374.3845 374.136553058 (4R)-3-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one (4R)-3-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one COC1=CC(C[C@H]2COC(=O)C2[C@H](O)C2=CC=C(O)C(OC)=C2)=CC=C1O InChI=1S/C20H22O7/c1-25-16-8-11(3-5-14(16)21)7-13-10-27-20(24)18(13)19(23)12-4-6-15(22)17(9-12)26-2/h3-6,8-9,13,18-19,21-23H,7,10H2,1-2H3/t13-,18?,19+/m0/s1 ZZSOKNNVDKKSDE-LPHKOSDUSA-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 Aromatic alcohols Carbonyl compounds Carboxylic acid esters Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Phenoxy compounds Secondary alcohols Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid Alcohol Alkyl aryl ether Anisole Aromatic alcohol Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Ether 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 Secondary alcohol Tetrahydrofuran logp 2.00 ALOGPS logs -4.01 ALOGPS solubility 3.67e-02 g/l ALOGPS logp 2.22 ChemAxon pka_strongest_acidic 9.63 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (4R)-3-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one ChemAxon average_mass 374.3845 ChemAxon mono_mass 374.136553058 ChemAxon smiles COC1=CC(C[C@H]2COC(=O)C2[C@H](O)C2=CC=C(O)C(OC)=C2)=CC=C1O ChemAxon formula C20H22O7 ChemAxon inchi InChI=1S/C20H22O7/c1-25-16-8-11(3-5-14(16)21)7-13-10-27-20(24)18(13)19(23)12-4-6-15(22)17(9-12)26-2/h3-6,8-9,13,18-19,21-23H,7,10H2,1-2H3/t13-,18?,19+/m0/s1 ChemAxon inchikey ZZSOKNNVDKKSDE-LPHKOSDUSA-N ChemAxon polar_surface_area 105.45 ChemAxon refractivity 97 ChemAxon polarizability 38.32 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 97656 Specdb::MsMs 97657 Specdb::MsMs 97658 Specdb::MsMs 162414 Specdb::MsMs 162415 Specdb::MsMs 162416 Specdb::MsMs 3597022 Specdb::MsMs 3597023 Specdb::MsMs 3597024 Specdb::MsMs 3597025 Specdb::MsMs 3597026 Specdb::MsMs 3597027 Amaranth Type 1 specific Amaranthus 3564 Annual wild rice Type 1 specific Zizania aquatica 75727 Barley Type 1 specific Hordeum vulgare 4513 Breakfast cereal Type 2 specific Bulgur Type 2 specific Cereals and cereal products Unknown generic Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 Flour Type 2 specific Hard wheat Type 1 specific Triticum durum 4567 Millet Type 1 specific Panicum miliaceum 4540 Oat Type 1 specific Avena sativa 4498 Oriental wheat Type 1 specific Triticum turanicum 376534 Quinoa Type 1 specific Chenopodium quinoa 63459 Red rice Type 1 specific Oryza rufipogon 4529 Rice Type 1 specific Oryza sativa 4530 Rye Type 1 specific Secale cereale 4550 Sesame Type 1 specific Sesamum orientale 4182 7.209 7.209000111 7.209000111 mg/100 g Sorghum Type 1 specific Sorghum bicolor 4558 Soy bean Type 1 specific Glycine max 3847 Spelt Type 1 specific Triticum spelta 58933 Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Teff Type 1 specific Eragrostis tef 110835 Triticale Type 1 specific X Triticosecale rimpaui Wheat Type 1 specific Triticum 4564 Wild rice Type 1 specific Zizania 15949