1.02010-04-08 22:08:07 UTC2019-11-26 03:02:42 UTCFDB008525RhapontinRhapontin is a member of the class of compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Rhapontin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rhapontin can be found in garden rhubarb, which makes rhapontin a potential biomarker for the consumption of this food product. Rhapontin has beneficial effects on diabetic mice, and in vitro results suggest it may be relevant to Alzheimer's disease with an action on beta amyloid .3,3',5-Trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside4'-Methoxy-3,3',5-trihydroxystilbene 3-O-beta-D-glucopyranosideGlucopyranoside, rhapontigenin-3, β-D-Glucopyranoside, rhapontigenin-3, beta-D-PonticinRhaponthinRhaponticinRhaponticineRhapontigenin 3-O-beta-D-glucopyranosideRhapontigenin, 3-β-D-glucopyranosideRhapontigenin, 3-beta-D-glucopyranosideRhapontinRhapontin (8CI)C21H24O9420.4099420.1420323662-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol155-58-8COC1=CC=C(\C=C/C2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2)C=C1OInChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2-GKAJCVFOJGXVIA-IHWYPQMZSA-N belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.Stilbene glycosidesOrganic compoundsPhenylpropanoids and polyketidesStilbenesStilbene glycosidesAromatic heteromonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAcetalsAlkyl aryl ethersAnisolesHexosesHydrocarbon derivativesMethoxybenzenesMethoxyphenolsO-glycosyl compoundsOxacyclic compoundsOxanesPhenolic glycosidesPhenoxy compoundsPolyolsPrimary alcoholsSecondary alcoholsStyrenes1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAcetalAlcoholAlkyl aryl etherAnisoleAromatic heteromonocyclic compoundBenzenoidEtherGlycosyl compoundHexose monosaccharideHydrocarbon derivativeMethoxybenzeneMethoxyphenolMonocyclic benzene moietyMonosaccharideO-glycosyl compoundOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenolPhenol etherPhenolic glycosidePhenoxy compoundPolyolPrimary alcoholSecondary alcoholStilbene glycosideStyrenelogp0.70logs-2.86solubility5.85e-01 g/lmelting_pointMp 236-237° dec.logp0.98pka_strongest_acidic9.21pka_strongest_basic-3iupac2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triolaverage_mass420.4099mono_mass420.142032366smilesCOC1=CC=C(\C=C/C2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2)C=C1OformulaC21H24O9inchiInChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2-inchikeyGKAJCVFOJGXVIA-IHWYPQMZSA-Npolar_surface_area149.07refractivity106.06polarizability42.33rotatable_bond_count6acceptor_count9donor_count6physiological_charge0formal_charge0Specdb::MsMs90633Specdb::MsMs90634Specdb::MsMs90635Specdb::MsMs153822Specdb::MsMs153823Specdb::MsMs153824Garden rhubarbType 1specificRheum rhabarbarum36211420.01420.01420.0mg/100 gestrogenic922