1.02010-04-08 22:05:28 UTC2019-11-26 02:57:48 UTCFDB002677HesperetinIsolated from Mentha (peppermint) and numerous Citrussubspecies, with lemons, tangerines and oranges being especially good sources. Nutriceutical with anti-cancer props. Glycosides also widely distributed
Hesperetin is a bioflavonoid and, to be more specific, a flavanone. Hesperidin (a flavonone glycoside) is water soluble due to the presence of the sugar part in its structure, so on ingestion it releases its aglycone i.e: hesperetin. Hesperidin is found in Citrus fruits.; Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. Hesperetin is also a biomarker for the consumption of citrus fruits.(-)-(S)-Hesperetin(-)-Hesperetin(S)-2,3-dihydro-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one(S)-Hesperetin3',5,7-Trihydroxy-4'-methoxyflavanone5,7, 3'-Trihydroxy-4'-methoxyflavanone5,7,3'-Trihydroxy-4'-methoxyflavanoneCyanidanon 4'-methyl ether 1626HesperinHesperitinPrestwick_908S-3',5,7-Trihydroxy-4'-methoxyflavanoneS-5,7,3'-Trihydroxy-4'-methoxyflavanoneYSO2C16H14O6302.2788302.07903818(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-onehesperetin520-33-2COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1AIONOLUJZLIMTK-AWEZNQCLSA-N belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.4'-O-methylated flavonoidsOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsO-methylated flavonoidsAromatic heteropolycyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids3'-hydroxyflavonoids5-hydroxyflavonoids7-hydroxyflavonoidsAlkyl aryl ethersAnisolesAryl alkyl ketonesChromonesFlavanonesHydrocarbon derivativesMethoxybenzenesMethoxyphenolsOrganic oxidesOxacyclic compoundsPhenoxy compoundsVinylogous acids1-benzopyran1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid3'-hydroxyflavonoid4p-methoxyflavonoid-skeleton5-hydroxyflavonoid7-hydroxyflavonoidAlkyl aryl etherAnisoleAromatic heteropolycyclic compoundAryl alkyl ketoneAryl ketoneBenzenoidBenzopyranChromaneChromoneEtherFlavanFlavanoneHydrocarbon derivativeHydroxyflavonoidKetoneMethoxybenzeneMethoxyphenolMonocyclic benzene moietyOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacyclePhenolPhenol etherPhenoxy compoundVinylogous acid3'-hydroxyflavanonesFlavanonesflavanonesmonomethoxyflavanonetrihydroxyflavanoneSolidlogp2.52logs-3.34solubility1.38e-01 g/lmelting_pointMp 228-230°logp2.68pka_strongest_acidic7.86pka_strongest_basic-4.6iupac(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-oneaverage_mass302.2788mono_mass302.07903818smilesCOC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1formulaC16H14O6inchiInChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1inchikeyAIONOLUJZLIMTK-AWEZNQCLSA-Npolar_surface_area96.22refractivity77.75polarizability29.3rotatable_bond_count2acceptor_count6donor_count3physiological_charge0formal_charge0Specdb::CMs18069Specdb::CMs38883Specdb::CMs173806Specdb::NmrOneD3891Specdb::NmrOneD4165Specdb::NmrOneD270718Specdb::NmrOneD270719Specdb::NmrOneD270720Specdb::NmrOneD270721Specdb::NmrOneD270722Specdb::NmrOneD270723Specdb::NmrOneD270724Specdb::NmrOneD270725Specdb::NmrOneD270726Specdb::NmrOneD270727Specdb::NmrOneD270728Specdb::NmrOneD270729Specdb::NmrOneD270730Specdb::NmrOneD270731Specdb::NmrOneD270732Specdb::NmrOneD270733Specdb::NmrOneD270734Specdb::NmrOneD270735Specdb::NmrOneD270736Specdb::NmrOneD270737Specdb::MsMs253713Specdb::MsMs253714Specdb::MsMs253715Specdb::MsMs273654Specdb::MsMs273655Specdb::MsMs273656Specdb::MsMs373837Specdb::MsMs373838Specdb::MsMs373839Specdb::MsMs373840Specdb::MsMs373841Specdb::MsMs373842Specdb::MsMs374783Specdb::MsMs436960Specdb::MsMs436961Specdb::MsMs436962Specdb::MsMs436963Specdb::MsMs436964Specdb::MsMs439207Specdb::MsMs439861Specdb::MsMs439862Specdb::MsMs444969Specdb::MsMs444970Specdb::MsMs444971Specdb::MsMs444972HMDB05782AlliumType 1specificAllium46780.00.00.0mg/100 gAlmondType 1specificPrunus dulcis37550.00.00.0mg/100 gAmerican cranberryType 1specificVaccinium macrocarpon137500.00.00.0mg/100 gAppleType 1specificMalus pumila2832100.00.00.0mg/100 gApricotType 1specificPrunus armeniaca365960.00.00.0mg/100 gAvocadoType 1specificPersea americana34350.00.00.0mg/100 gBananaType 1specificMusa acuminata46410.00.00.0mg/100 gBeerType 2specific0.00.00.0mg/100 gBlack teaType 10.00.00.0mg/100 gBlackcurrantType 1specificRibes nigrum785110.00.00.0mg/100 gBrazil nutType 1specificBertholletia excelsa36450.00.00.0mg/100 gBroccoliType 1specificBrassica oleracea var. italica367740.00.00.0mg/100 gBrussel sproutsType 1specificBrassica oleracea var. gemmifera1786160.00.00.0mg/100 gCarrotType 1specificDaucus carota ssp. sativus792000.00.00.0mg/100 gCashew nutType 1specificAnacardium occidentale1719290.00.00.0mg/100 gCelery leavesType 1specificApium graveolens var. secalinum9415880.00.00.0mg/100 gCelery stalksType 1specificApium graveolens var. dulce1177810.00.00.0mg/100 gChivesType 1specificAllium schoenoprasum749000.00.00.0mg/100 gCitrusUnknowngenericColorado pinyonType 1specificPinus edulis33400.00.00.0mg/100 gCommon beanType 1specificPhaseolus vulgaris38850.00.00.0mg/100 gCommon cabbageType 1specificBrassica oleracea37120.00.00.0mg/100 gCommon grapeType 1specificVitis vinifera297600.00.00.0mg/100 gCommon oreganoType 1specificOriganum vulgare393520.00.00.0mg/100 gCommon sageType 1specificSalvia officinalis388680.00.00.0mg/100 gCommon thymeType 1specificThymus vulgaris499920.00.00.0mg/100 gCommon walnutType 1specificJuglans regia512400.00.00.0mg/100 gCorianderType 1specificCoriandrum sativum40470.00.00.0mg/100 gDateType 1specificPhoenix dactylifera423450.00.00.0mg/100 gDillType 1specificAnethum graveolens409220.00.00.0mg/100 gEuropean plumType 1specificPrunus domestica37580.00.00.0mg/100 gFigType 1specificFicus carica34940.00.00.0mg/100 gFruit juiceType 2specificGarden cressType 1specificLepidium sativum331250.00.00.0mg/100 gGarden onion (var.)Type 1specificAllium cepa var. cepa46790.00.00.0mg/100 gGarden tomatoType 1specificSolanum lycopersicum40810.00.00.0mg/100 gGarden tomato (var.)Type 1specificSolanum lycopersicum var. lycopersicum3977550.00.00.0mg/100 gGlobe artichokeType 1specificCynara scolymus598950.00.00.0mg/100 gGrape wineType 2specific0.21860.630.0mg/100 gGrapefruitType 1specificCitrus X paradisi376561.1328572.350.35mg/100 gGreen beanType 1specificPhaseolus vulgaris38850.00.00.0mg/100 gGreen bell pepperType 1specificCapsicum annuum40720.00.00.0mg/100 gGreen teaType 10.00.00.0mg/100 gGreen vegetablesUnknowngenericHazelnutType 1specificCorylus134500.00.00.0mg/100 gHerbs and SpicesUnknowngenericItalian oreganoType 1specificOriganum X majoricum13842070.00.00.0mg/100 gItalian sweet red pepperType 1specificCapsicum annuum40720.00.00.0mg/100 gKiwiType 1specificActinidia chinensis36250.00.00.0mg/100 gLemonType 1specificCitrus limon270818.22527.913.43mg/100 gLemon balmType 1specificMelissa officinalis393380.00.00.0mg/100 gLettuceType 1specificLactuca sativa42360.00.00.0mg/100 gLimeType 1specificCitrus aurantiifolia15903343.043.043.0mg/100 gLingonberryType 1specificVaccinium vitis-idaea1807720.00.00.0mg/100 gLovageType 1specificLevisticum officinale480420.00.00.0mg/100 gMacadamia nutType 1specificMacadamia43290.00.00.0mg/100 gMandarin orange (Clementine, Tangerine)Type 1specificCitrus reticulata8557115.68666722.017.94mg/100 gMenthaType 1specificMentha21819MuskmelonType 1specificCucumis melo36560.00.00.0mg/100 gNectarineType 1specificPrunus persica var. nucipersica3238510.00.00.0mg/100 gOrange mintType 1specificMentha aquatica190902Oxheart cabbageType 1specificBrassica oleracea var. conica0.00.00.0mg/100 gParsleyType 1specificPetroselinum crispum40430.00.00.0mg/100 gPeachType 1specificPrunus persica37600.00.00.0mg/100 gPeanutType 1specificArachis hypogaea38180.00.00.0mg/100 gPearType 1specificPyrus communis232110.00.00.0mg/100 gPecan nutType 1specificCarya illinoinensis322010.00.00.0mg/100 gPepperType 1specificCapsicum annuum40720.00.00.0mg/100 gPeppermintType 1specificMentha X piperita3425610.1610.1610.16mg/100 gPersian limeType 1specificCitrus latifolia20054125.98543.08.97mg/100 gPineappleType 1specificAnanas comosus46150.00.00.0mg/100 gPistachioType 1specificPistacia vera555130.00.00.0mg/100 gPotatoType 1specificSolanum tuberosum41130.00.00.0mg/100 gPrunus (Cherry, Plum)Type 1specificPrunus37540.00.00.0mg/100 gPummeloType 1specificCitrus maxima373345.0958.41.79mg/100 gRadishType 1specificRaphanus sativus37260.00.00.0mg/100 gRapiniType 1specificBrassica ruvo12044340.00.00.0mg/100 gRed bell pepperType 1specificCapsicum annuum40720.00.00.0mg/100 gRed raspberryType 1specificRubus idaeus322470.00.00.0mg/100 gRedcurrantType 1specificRibes rubrum1752280.00.00.0mg/100 gRosemaryType 1specificRosmarinus officinalis393670.00.00.0mg/100 gRubus (Blackberry, Raspberry)Type 1specificRubus232160.00.00.0mg/100 gSausageType 2specific0.00.00.0mg/100 gSavoy cabbageType 1specificBrassica oleracea var. sabauda12160100.00.00.0mg/100 gStrawberryType 1specificFragaria X ananassa37470.00.00.0mg/100 gSweet basilType 1specificOcimum basilicum393500.00.00.0mg/100 gSweet cherryType 1specificPrunus avium422290.00.00.0mg/100 gSweet orangeType 1specificCitrus sinensis271118.85777833.6000003819.0mg/100 gTarragonType 1specificArtemisia dracunculus723410.00.00.0mg/100 gTeaType 1specificCamellia sinensis44420.00.00.0mg/100 gVaccinium (Blueberry, Cranberry, Huckleberry)Type 1specificVaccinium137490.00.00.0mg/100 gWatercressType 1specificRorippa nasturtium-aquaticum1355180.00.00.0mg/100 gWatermelonType 1specificCitrullus lanatus36540.00.00.0mg/100 gWelsh onionType 1specificAllium fistulosum358750.0070.0070.007mg/100 gWild celeryType 1specificApium graveolens40450.00.00.0mg/100 gYellow bell pepperType 1specificCapsicum annuum40720.00.00.0mg/100 gbitterSterol O-acyltransferase 1P35610SOAT1anti bacterial145A substance that kills or slows the growth of bacteria.anti feedant275anti lipolytic406anti viral689A substance that destroys or inhibits replication of viruses.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.cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.fungistat942hepatoprotective981Any compound that is able to prevent damage to the liver.pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.