1.0 2010-04-08 22:10:15 UTC 2025-11-18 23:38:02 UTC FDB012578 Lariciresinol (-)-lariciresinol is a member of the class of compounds known as 7,9'-epoxylignans. 7,9'-epoxylignans are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as ostrich fern, pepper (c. frutescens), ohelo berry, and guava, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products. 4,4',9-Trihydroxy-3,3'-dimethoxy-7,9'-epoxylignan Arbo 4 Lariciresinol C20H24O6 360.401 360.1572885 4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenol lariciresinol 27003-73-2 COC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1O InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3 MHXCIKYXNYCMHY-UHFFFAOYSA-N belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. 7,9'-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 Primary alcohols Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 7,9p-epoxylignan Alcohol 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 Primary alcohol Tetrahydrofuran logp 2.16 ALOGPS logs -4.24 ALOGPS solubility 2.05e-02 g/l ALOGPS melting_point Mp 167-168° (162-164°) logp 2.31 ChemAxon pka_strongest_acidic 9.75 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenol ChemAxon average_mass 360.401 ChemAxon mono_mass 360.1572885 ChemAxon smiles COC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1O ChemAxon formula C20H24O6 ChemAxon inchi InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3 ChemAxon inchikey MHXCIKYXNYCMHY-UHFFFAOYSA-N ChemAxon polar_surface_area 88.38 ChemAxon refractivity 97.19 ChemAxon polarizability 38.57 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 107956 Specdb::CMs 120427 Specdb::CMs 925123 Specdb::CMs 925124 Specdb::CMs 925125 Specdb::CMs 925126 Specdb::CMs 925127 Specdb::CMs 925128 Specdb::CMs 925129 Specdb::CMs 925130 Specdb::CMs 925131 Specdb::CMs 925132 Specdb::CMs 925133 Specdb::CMs 925134 Specdb::CMs 925135 Specdb::CMs 925136 Specdb::MsMs 20789 Specdb::MsMs 20790 Specdb::MsMs 20791 Specdb::MsMs 21014 Specdb::MsMs 21015 Specdb::MsMs 21016 Specdb::MsMs 22340 Specdb::MsMs 22341 Specdb::MsMs 22342 Specdb::MsMs 22565 Specdb::MsMs 22566 Specdb::MsMs 22567 Specdb::MsMs 2236058 Specdb::MsMs 2237317 Specdb::MsMs 2238206 Specdb::MsMs 2239380 Specdb::MsMs 2240086 Specdb::MsMs 2241372 Specdb::MsMs 2241602 Specdb::MsMs 2242216 Specdb::MsMs 2242378 Specdb::MsMs 2243487 Specdb::MsMs 2243671 Specdb::MsMs 2244499 Specdb::MsMs 2245625 Amaranth Type 1 specific Amaranthus 3564 Annual wild rice Type 1 specific Zizania aquatica 75727 Asparagus Type 1 specific Asparagus officinalis 4686 0.047 0.046999998 0.046999998 mg/100 g Barley Type 1 specific Hordeum vulgare 4513 0.085 0.085000001 0.085000001 mg/100 g Black elderberry Type 1 specific Sambucus nigra 4202 Breakfast cereal Type 2 specific 0.144333 0.144333333 0.144333333 mg/100 g Bulgur Type 2 specific Cereals and cereal products Unknown generic Common buckwheat Type 1 specific Fagopyrum esculentum 3617 0.362 0.361999989 0.361999989 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 0.1405 0.180000007 0.101 mg/100 g Corn Type 1 specific Zea mays 4577 Cucumber Type 1 specific Cucumis sativus 3659 0.001 0.001 0.001 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.068 0.068000004 0.068000004 mg/100 g Flaxseed Type 1 specific Linum usitatissimum 4006 11.45575 11.455749989 11.455749989 mg/100 g Flour Type 2 specific Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.011 0.011 0.011 mg/100 g Grape wine Type 2 specific 0.004544 0.0053375 0.00375 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 Hard wheat Type 1 specific Triticum durum 4567 Italian sweet red pepper Type 1 specific Capsicum annuum 4072 Kiwi Type 1 specific Actinidia chinensis 3625 0.01 0.01 0.01 mg/100 g Millet Type 1 specific Panicum miliaceum 4540 Miso Type 2 specific 0.0244 0.0244 0.0244 mg/100 g Oat Type 1 specific Avena sativa 4498 0.183 0.182999998 0.182999998 mg/100 g Olive Type 1 specific Olea europaea 4146 0.0125 0.035999998 0.004 mg/100 g Orange bell pepper Type 1 specific Capsicum annuum 4072 Oriental wheat Type 1 specific Triticum turanicum 376534 Other soy product Type 2 specific 0.004533 0.0113 0.0 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 Pineapple Type 1 specific Ananas comosus 4615 0.067 0.067000002 0.067000002 mg/100 g Poppy Type 1 specific Papaver 3468 0.01 0.01 0.01 mg/100 g Quinoa Type 1 specific Chenopodium quinoa 63459 Radish (var.) Type 1 specific Raphanus sativus var. sativus 240228 0.014 0.014 0.014 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 Red rice Type 1 specific Oryza rufipogon 4529 Rice Type 1 specific Oryza sativa 4530 Rye Type 1 specific Secale cereale 4550 0.324 0.324000001 0.324000001 mg/100 g Sesame Type 1 specific Sesamum orientale 4182 10.3675 10.367500067 10.367500067 mg/100 g Sorghum Type 1 specific Sorghum bicolor 4558 Soy bean Type 1 specific Glycine max 3847 0.0205 0.060800001 0.0 mg/100 g Soy milk Type 2 specific 0.006175 0.006175 0.006175 mg/100 g Soy sauce Type 2 specific 0.0 0.0 0.0 mg/100 g Soy yogurt Type 2 specific 0.0176 0.0176 0.0176 mg/100 g Spelt Type 1 specific Triticum spelta 58933 Sunflower Type 1 specific Helianthus annuus 4232 0.3355 0.671000004 0.0 mg/100 g Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Teff Type 1 specific Eragrostis tef 110835 Tofu Type 2 specific 0.0415 0.0415 0.0415 mg/100 g Triticale Type 1 specific X Triticosecale rimpaui Wheat Type 1 specific Triticum 4564 Wheat bread Type 2 specific 0.04875 0.072999999 0.024499999 mg/100 g Wild rice Type 1 specific Zizania 15949 Yellow bell pepper Type 1 specific Capsicum annuum 4072 Yogurt Type 2 specific 0.0176 0.0176 0.0176 mg/100 g