1.02010-04-08 22:11:23 UTC2019-11-26 03:10:32 UTCFDB014653OleuropeinBitter principle of olives. Nutriceutical with antioxidant props.
Oleuropein is a chemical compound found in olive leaf from the olive tree (and leaves of privet) together with other closely related compounds such as 10-hydroxyoleuropein, ligstroside, and 10-hydroxyligstroside. All these compounds are tyrosol esters of elenolic acid that are further hydroxylated and glycosylated. Oleuropein and its metabolite hydroxytyrosol have powerful antioxidant activity both in vivo and in vitro and give extra-virgin olive oil its bitter, pungent taste. Oleuropein preparations have been claimed to strengthen the immune system.C25H32O13540.5138540.18429111methyl (2S,3Z,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylatemethyl (4S,5Z,6S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate32619-42-4[H][C@]1(CC(=O)OCCC2=CC(O)=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OCInChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3-/t14-,18+,20+,21-,22+,24-,25-/m0/s1RFWGABANNQMHMZ-WLFYAOHHSA-N belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.Terpene glycosidesOrganic compoundsLipids and lipid-like moleculesPrenol lipidsTerpene glycosidesAromatic heteromonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAcetalsAromatic monoterpenoidsBenzene and substituted derivativesCarbonyl compoundsCatecholsDicarboxylic acids and derivativesEnoate estersHydrocarbon derivativesIridoids and derivativesMethyl estersMonocyclic monoterpenoidsMonosaccharidesO-glycosyl compoundsOrganic oxidesOxacyclic compoundsOxanesPolyolsPrimary alcoholsSecondary alcoholsSugar acids and derivativesTyrosols and derivativesVinylogous esters1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAcetalAlcoholAlpha,beta-unsaturated carboxylic esterAromatic heteromonocyclic compoundAromatic monoterpenoidBenzenoidCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCatecholDicarboxylic acid or derivativesEnoate esterGlycosyl compoundHydrocarbon derivativeMethyl esterMonocyclic benzene moietyMonocyclic monoterpenoidMonosaccharideMonoterpenoidO-glycosyl compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenolPolyolPrimary alcoholSecoiridoid-skeletonSecondary alcoholSugar acidTerpene glycosideTyrosol derivativeVinylogous esterlogp0.63logs-2.87solubility7.33e-01 g/lmelting_pointMp 89-91°logp0.11pka_strongest_acidic4.94pka_strongest_basic-3iupacmethyl (2S,3Z,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylateaverage_mass540.5138mono_mass540.18429111smiles[H][C@]1(CC(=O)OCCC2=CC(O)=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OCformulaC25H32O13inchiInChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3-/t14-,18+,20+,21-,22+,24-,25-/m0/s1inchikeyRFWGABANNQMHMZ-WLFYAOHHSA-Npolar_surface_area201.67refractivity128.22polarizability53.4rotatable_bond_count11acceptor_count11donor_count6physiological_charge0formal_charge0Specdb::MsMs49893Specdb::MsMs49894Specdb::MsMs49895Specdb::MsMs115869Specdb::MsMs115870Specdb::MsMs115871Specdb::CMs19415Specdb::CMs44613HMDB35872#<Reference:0x0000555675b90e80>#<Reference:0x0000555675b90cc8>#<Reference:0x0000555675b90ae8>#<Reference:0x0000555675b90930>#<Reference:0x0000555675b90778>FruitsUnknowngenericOliveType 1specificOlea europaea414631.93961672.016299820.000055mg/100 gRapeType 1specificBrassica napus var. napus1380110.00.00.0mg/100 gbitterangiotensin converting enzyme inhibitor18An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).anti arrhythmic129A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.anti hypertensive352Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti spasmodic619Any substance introduced into a living organism with therapeutic or diagnostic purpose.antioxidant502A 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.bacteristat725A substance that kills or slows the growth of bacteria.coronarydilator835hypotensive1021vasodilator1413A drug used to cause dilation of the blood vessels.