1.0 2010-04-08 22:10:17 UTC 2025-11-18 23:38:37 UTC FDB012660 Secoisolariciresinol Secoisolariciresinol is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as barley, wheat bread, broad bean, and poppy, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 % . 2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol, 9CI 4,4',9,9'-Tetrahydroxy-3,3'-dimethoxylignan seco-Isolariciresinol C20H26O6 362.4168 362.172938564 2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol secoisolariciresinol COC1=CC(CC(CO)C(CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3 PUETUDUXMCLALY-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Dibenzylbutanediol lignans Organic compounds Lignans, neolignans and related compounds Dibenzylbutane lignans Dibenzylbutanediol lignans Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds Primary alcohols 1-hydroxy-2-unsubstituted benzenoid Alcohol Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Dibenzylbutanediol Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Primary alcohol a lignan logp 2.05 ALOGPS logs -4.48 ALOGPS solubility 1.20e-02 g/l ALOGPS logp 2.33 ChemAxon pka_strongest_acidic 9.96 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol ChemAxon average_mass 362.4168 ChemAxon mono_mass 362.172938564 ChemAxon smiles COC1=CC(CC(CO)C(CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O ChemAxon formula C20H26O6 ChemAxon inchi InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3 ChemAxon inchikey PUETUDUXMCLALY-UHFFFAOYSA-N ChemAxon polar_surface_area 99.38 ChemAxon refractivity 99.29 ChemAxon polarizability 38.77 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 107919 Specdb::CMs 120385 Specdb::CMs 881715 Specdb::CMs 881716 Specdb::CMs 881717 Specdb::CMs 881718 Specdb::CMs 881719 Specdb::CMs 881720 Specdb::CMs 881721 Specdb::CMs 881722 Specdb::CMs 881723 Specdb::CMs 881724 Specdb::CMs 881725 Specdb::CMs 881726 Specdb::CMs 881727 Specdb::CMs 881728 Specdb::CMs 881729 Specdb::CMs 881730 Specdb::CMs 881731 Specdb::CMs 881732 Specdb::MsMs 20756 Specdb::MsMs 20757 Specdb::MsMs 20758 Specdb::MsMs 21293 Specdb::MsMs 21294 Specdb::MsMs 21295 Specdb::MsMs 22307 Specdb::MsMs 22308 Specdb::MsMs 22309 Specdb::MsMs 22844 Specdb::MsMs 22845 Specdb::MsMs 22846 Specdb::MsMs 2226797 Specdb::MsMs 2252813 Specdb::MsMs 2253509 Specdb::MsMs 2253685 Specdb::MsMs 2254893 Specdb::MsMs 2255592 Specdb::MsMs 2255665 Specdb::MsMs 2256846 Specdb::MsMs 2256913 Specdb::MsMs 2257658 Specdb::MsMs 2257762 Specdb::MsMs 2258785 Specdb::MsMs 2258954 Apricot Type 1 specific Prunus armeniaca 36596 Asparagus Type 1 specific Asparagus officinalis 4686 0.183 0.182999998 0.182999998 mg/100 g Barley Type 1 specific Hordeum vulgare 4513 0.03 0.029999999 0.029999999 mg/100 g Black tea Type 1 0.030677 0.035150001 0.027899999 mg/100 g Black-eyed pea Type 1 specific Vigna unguiculata ssp. unguiculata 3920 Breakfast cereal Type 2 specific 0.015667 0.015666667 0.015666667 mg/100 g Broad bean Type 1 specific Vicia faba 3906 Broccoli Type 1 specific Brassica oleracea var. italica 36774 Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 Capers Type 1 specific Capparis spinosa 65558 Carrot Type 1 specific Daucus carota ssp. sativus 79200 Cocoa powder Type 2 specific Common buckwheat Type 1 specific Fagopyrum esculentum 3617 0.131 0.130999997 0.130999997 mg/100 g Common oregano Type 1 specific Origanum vulgare 39352 Common wheat Type 1 specific Triticum aestivum 4565 0.0165 0.033 0.0 mg/100 g Cucumber Type 1 specific Cucumis sativus 3659 0.002 0.002 0.002 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.005 0.005 0.005 mg/100 g Flaxseed Type 1 specific Linum usitatissimum 4006 257.600003 257.600003052 257.600003052 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.001 0.001 0.001 mg/100 g Garlic Type 1 specific Allium sativum 4682 Ginger Type 1 specific Zingiber officinale 94328 Grape wine Type 2 specific 0.017906 0.0290625 0.00675 mg/100 g Grapefruit Type 1 specific Citrus X paradisi 37656 Green tea Type 1 0.030677 0.035150001 0.027899999 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 0.116 0.115999997 0.115999997 mg/100 g Miso Type 2 specific 0.0188 0.0188 0.0188 mg/100 g Multigrain bread Type 2 specific Mung bean Type 1 specific Vigna radiata 157791 Oat Type 1 specific Avena sativa 4498 0.019 0.018999999 0.018999999 mg/100 g Olive Type 1 specific Olea europaea 4146 0.00825 0.026000001 0.0 mg/100 g Other soy product Type 2 specific 0.020567 0.035 0.0106 mg/100 g Pineapple Type 1 specific Ananas comosus 4615 0.007 0.007 0.007 mg/100 g Poppy Type 1 specific Papaver 3468 0.0 0.0 0.0 mg/100 g Radish (var.) Type 1 specific Raphanus sativus var. sativus 240228 0.001 0.001 0.001 mg/100 g Rose hip Type 1 specific Rosa 3764 Rye Type 1 specific Secale cereale 4550 0.0311 0.0311 0.0311 mg/100 g Rye bread Type 2 specific 1.152 1.15199995 1.15199995 mg/100 g Sesame Type 1 specific Sesamum orientale 4182 0.1095 0.109499998 0.109499998 mg/100 g Soy bean Type 1 specific Glycine max 3847 0.085417 0.302566677 0.0 mg/100 g Soy milk Type 2 specific 0.00225 0.00225 0.00225 mg/100 g Soy sauce Type 2 specific 0.0103 0.0103 0.0103 mg/100 g Soy yogurt Type 2 specific 0.0253 0.0253 0.0253 mg/100 g Sunflower Type 1 specific Helianthus annuus 4232 0.092375 0.184749994 0.0 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 Sweet orange Type 1 specific Citrus sinensis 2711 Tea Type 1 specific Camellia sinensis 4442 0.030677 0.035150001 0.027899999 mg/100 g Tofu Type 2 specific 0.01585 0.01585 0.01585 mg/100 g Wheat bread Type 2 specific 0.01175 0.014999999 0.0085 mg/100 g Yogurt Type 2 specific 0.0253 0.0253 0.0253 mg/100 g Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Aromatase inhibitor 705 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms.