1.02010-04-08 22:10:15 UTC2019-11-26 03:07:08 UTCFDB012578Lariciresinol(-)-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'-epoxylignanArbo 4LariciresinolC20H24O6360.401360.15728854-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenollariciresinol27003-73-2COC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1OInChI=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,7,10-11H2,1-2H3MHXCIKYXNYCMHY-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'-epoxylignansOrganic compoundsLignans, neolignans and related compoundsFuranoid lignansTetrahydrofuran lignansAromatic heteromonocyclic compounds1-hydroxy-2-unsubstituted benzenoidsAlkyl aryl ethersAnisolesDialkyl ethersHydrocarbon derivativesMethoxybenzenesMethoxyphenolsOxacyclic compoundsPhenoxy compoundsPrimary alcoholsTetrahydrofurans1-hydroxy-2-unsubstituted benzenoid7,9p-epoxylignanAlcoholAlkyl aryl etherAnisoleAromatic heteromonocyclic compoundBenzenoidDialkyl etherEtherHydrocarbon derivativeMethoxybenzeneMethoxyphenolMonocyclic benzene moietyOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacyclePhenolPhenol etherPhenoxy compoundPrimary alcoholTetrahydrofuranlogp2.16logs-4.24solubility2.05e-02 g/lmelting_pointMp 167-168° (162-164°)logp2.31pka_strongest_acidic9.75pka_strongest_basic-2.6iupac4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenolaverage_mass360.401mono_mass360.1572885smilesCOC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1OformulaC20H24O6inchiInChI=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,7,10-11H2,1-2H3inchikeyMHXCIKYXNYCMHY-UHFFFAOYSA-Npolar_surface_area88.38refractivity97.19polarizability38.57rotatable_bond_count6acceptor_count6donor_count3physiological_charge0formal_charge0Specdb::CMs107956Specdb::CMs120427Specdb::CMs925123Specdb::CMs925124Specdb::CMs925125Specdb::CMs925126Specdb::CMs925127Specdb::CMs925128Specdb::CMs925129Specdb::CMs925130Specdb::CMs925131Specdb::CMs925132Specdb::CMs925133Specdb::CMs925134Specdb::CMs925135Specdb::CMs925136Specdb::MsMs20789Specdb::MsMs20790Specdb::MsMs20791Specdb::MsMs21014Specdb::MsMs21015Specdb::MsMs21016Specdb::MsMs22340Specdb::MsMs22341Specdb::MsMs22342Specdb::MsMs22565Specdb::MsMs22566Specdb::MsMs22567Specdb::MsMs2236058Specdb::MsMs2237317Specdb::MsMs2238206Specdb::MsMs2239380Specdb::MsMs2240086Specdb::MsMs2241372Specdb::MsMs2241602Specdb::MsMs2242216Specdb::MsMs2242378Specdb::MsMs2243487Specdb::MsMs2243671Specdb::MsMs2244499Specdb::MsMs2245625AmaranthType 1specificAmaranthus3564Annual wild riceType 1specificZizania aquatica75727AsparagusType 1specificAsparagus officinalis46860.0470.0469999980.046999998mg/100 gBarleyType 1specificHordeum vulgare45130.0850.0850000010.085000001mg/100 gBlack elderberryType 1specificSambucus nigra4202Breakfast cerealType 2specific0.1443330.1443333330.144333333mg/100 gBulgurType 2specificCereals and cereal productsUnknowngenericCommon buckwheatType 1specificFagopyrum esculentum36170.3620.3619999890.361999989mg/100 gCommon wheatType 1specificTriticum aestivum45650.14050.1800000070.101mg/100 gCornType 1specificZea mays4577CucumberType 1specificCucumis sativus36590.0010.0010.001mg/100 gEggplantType 1specificSolanum melongena41110.0680.0680000040.068000004mg/100 gFlaxseedType 1specificLinum usitatissimum400611.4557511.45574998911.455749989mg/100 gFlourType 2specificGarden tomato (var.)Type 1specificSolanum lycopersicum var. lycopersicum3977550.0110.0110.011mg/100 gGrape wineType 2specific0.0045440.00533750.00375mg/100 gGreen bell pepperType 1specificCapsicum annuum4072Hard wheatType 1specificTriticum durum4567Italian sweet red pepperType 1specificCapsicum annuum4072KiwiType 1specificActinidia chinensis36250.010.010.01mg/100 gMilletType 1specificPanicum miliaceum4540MisoType 2specific0.02440.02440.0244mg/100 gOatType 1specificAvena sativa44980.1830.1829999980.182999998mg/100 gOliveType 1specificOlea europaea41460.01250.0359999980.004mg/100 gOrange bell pepperType 1specificCapsicum annuum4072Oriental wheatType 1specificTriticum turanicum376534Other soy productType 2specific0.0045330.01130.0mg/100 gPepperType 1specificCapsicum annuum4072PineappleType 1specificAnanas comosus46150.0670.0670000020.067000002mg/100 gPoppyType 1specificPapaver34680.010.010.01mg/100 gQuinoaType 1specificChenopodium quinoa63459Radish (var.)Type 1specificRaphanus sativus var. sativus2402280.0140.0140.014mg/100 gRed bell pepperType 1specificCapsicum annuum4072Red riceType 1specificOryza rufipogon4529RiceType 1specificOryza sativa4530RyeType 1specificSecale cereale45500.3240.3240000010.324000001mg/100 gSesameType 1specificSesamum orientale418210.367510.36750006710.367500067mg/100 gSorghumType 1specificSorghum bicolor4558Soy beanType 1specificGlycine max38470.02050.0608000010.0mg/100 gSoy milkType 2specific0.0061750.0061750.006175mg/100 gSoy sauceType 2specific0.00.00.0mg/100 gSoy yogurtType 2specific0.01760.01760.0176mg/100 gSpeltType 1specificTriticum spelta58933SunflowerType 1specificHelianthus annuus42320.33550.6710000040.0mg/100 gTartary buckwheatType 1specificFagopyrum tataricum62330TeffType 1specificEragrostis tef110835TofuType 2specific0.04150.04150.0415mg/100 gTriticaleType 1specificX Triticosecale rimpauiWheatType 1specificTriticum4564Wheat breadType 2specific0.048750.0729999990.024499999mg/100 gWild riceType 1specificZizania15949Yellow bell pepperType 1specificCapsicum annuum4072YogurtType 2specific0.01760.01760.0176mg/100 g