1.0 2010-04-08 22:05:28 UTC 2019-11-26 02:57:48 UTC FDB002677 Hesperetin Isolated 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)-Hesperetin 3',5,7-Trihydroxy-4'-methoxyflavanone 5,7, 3'-Trihydroxy-4'-methoxyflavanone 5,7,3'-Trihydroxy-4'-methoxyflavanone Cyanidanon 4'-methyl ether 1626 Hesperin Hesperitin Prestwick_908 S-3',5,7-Trihydroxy-4'-methoxyflavanone S-5,7,3'-Trihydroxy-4'-methoxyflavanone YSO2 C16H14O6 302.2788 302.07903818 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one hesperetin 520-33-2 COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1 InChI=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/s1 AIONOLUJZLIMTK-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 flavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids O-methylated flavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Anisoles Aryl alkyl ketones Chromones Flavanones Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Organic oxides Oxacyclic compounds Phenoxy compounds Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4p-methoxyflavonoid-skeleton 5-hydroxyflavonoid 7-hydroxyflavonoid Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Flavan Flavanone Hydrocarbon derivative Hydroxyflavonoid Ketone Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Vinylogous acid 3'-hydroxyflavanones Flavanones flavanones monomethoxyflavanone trihydroxyflavanone Solid logp 2.52 ALOGPS logs -3.34 ALOGPS solubility 1.38e-01 g/l ALOGPS melting_point Mp 228-230° logp 2.68 ChemAxon pka_strongest_acidic 7.86 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 302.2788 ChemAxon mono_mass 302.07903818 ChemAxon smiles COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C16H14O6 ChemAxon inchi InChI=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/s1 ChemAxon inchikey AIONOLUJZLIMTK-AWEZNQCLSA-N ChemAxon polar_surface_area 96.22 ChemAxon refractivity 77.75 ChemAxon polarizability 29.3 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18069 Specdb::CMs 38883 Specdb::CMs 173806 Specdb::NmrOneD 3891 Specdb::NmrOneD 4165 Specdb::NmrOneD 270718 Specdb::NmrOneD 270719 Specdb::NmrOneD 270720 Specdb::NmrOneD 270721 Specdb::NmrOneD 270722 Specdb::NmrOneD 270723 Specdb::NmrOneD 270724 Specdb::NmrOneD 270725 Specdb::NmrOneD 270726 Specdb::NmrOneD 270727 Specdb::NmrOneD 270728 Specdb::NmrOneD 270729 Specdb::NmrOneD 270730 Specdb::NmrOneD 270731 Specdb::NmrOneD 270732 Specdb::NmrOneD 270733 Specdb::NmrOneD 270734 Specdb::NmrOneD 270735 Specdb::NmrOneD 270736 Specdb::NmrOneD 270737 Specdb::MsMs 253713 Specdb::MsMs 253714 Specdb::MsMs 253715 Specdb::MsMs 273654 Specdb::MsMs 273655 Specdb::MsMs 273656 Specdb::MsMs 373837 Specdb::MsMs 373838 Specdb::MsMs 373839 Specdb::MsMs 373840 Specdb::MsMs 373841 Specdb::MsMs 373842 Specdb::MsMs 374783 Specdb::MsMs 436960 Specdb::MsMs 436961 Specdb::MsMs 436962 Specdb::MsMs 436963 Specdb::MsMs 436964 Specdb::MsMs 439207 Specdb::MsMs 439861 Specdb::MsMs 439862 Specdb::MsMs 444969 Specdb::MsMs 444970 Specdb::MsMs 444971 Specdb::MsMs 444972 HMDB05782 Allium Type 1 specific Allium 4678 0.0 0.0 0.0 mg/100 g Almond Type 1 specific Prunus dulcis 3755 0.0 0.0 0.0 mg/100 g American cranberry Type 1 specific Vaccinium macrocarpon 13750 0.0 0.0 0.0 mg/100 g Apple Type 1 specific Malus pumila 283210 0.0 0.0 0.0 mg/100 g Apricot Type 1 specific Prunus armeniaca 36596 0.0 0.0 0.0 mg/100 g Avocado Type 1 specific Persea americana 3435 0.0 0.0 0.0 mg/100 g Banana Type 1 specific Musa acuminata 4641 0.0 0.0 0.0 mg/100 g Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Black tea Type 1 0.0 0.0 0.0 mg/100 g Blackcurrant Type 1 specific Ribes nigrum 78511 0.0 0.0 0.0 mg/100 g Brazil nut Type 1 specific Bertholletia excelsa 3645 0.0 0.0 0.0 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 0.0 0.0 0.0 mg/100 g Brussel sprouts Type 1 specific Brassica oleracea var. gemmifera 178616 0.0 0.0 0.0 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Cashew nut Type 1 specific Anacardium occidentale 171929 0.0 0.0 0.0 mg/100 g Celery leaves Type 1 specific Apium graveolens var. secalinum 941588 0.0 0.0 0.0 mg/100 g Celery stalks Type 1 specific Apium graveolens var. dulce 117781 0.0 0.0 0.0 mg/100 g Chives Type 1 specific Allium schoenoprasum 74900 0.0 0.0 0.0 mg/100 g Citrus Unknown generic Colorado pinyon Type 1 specific Pinus edulis 3340 0.0 0.0 0.0 mg/100 g Common bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Common cabbage Type 1 specific Brassica oleracea 3712 0.0 0.0 0.0 mg/100 g Common grape Type 1 specific Vitis vinifera 29760 0.0 0.0 0.0 mg/100 g Common oregano Type 1 specific Origanum vulgare 39352 0.0 0.0 0.0 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 0.0 0.0 0.0 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 0.0 0.0 0.0 mg/100 g Common walnut Type 1 specific Juglans regia 51240 0.0 0.0 0.0 mg/100 g Coriander Type 1 specific Coriandrum sativum 4047 0.0 0.0 0.0 mg/100 g Date Type 1 specific Phoenix dactylifera 42345 0.0 0.0 0.0 mg/100 g Dill Type 1 specific Anethum graveolens 40922 0.0 0.0 0.0 mg/100 g European plum Type 1 specific Prunus domestica 3758 0.0 0.0 0.0 mg/100 g Fig Type 1 specific Ficus carica 3494 0.0 0.0 0.0 mg/100 g Fruit juice Type 2 specific Garden cress Type 1 specific Lepidium sativum 33125 0.0 0.0 0.0 mg/100 g Garden onion (var.) Type 1 specific Allium cepa var. cepa 4679 0.0 0.0 0.0 mg/100 g Garden tomato Type 1 specific Solanum lycopersicum 4081 0.0 0.0 0.0 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.0 0.0 0.0 mg/100 g Globe artichoke Type 1 specific Cynara scolymus 59895 0.0 0.0 0.0 mg/100 g Grape wine Type 2 specific 0.2186 0.63 0.0 mg/100 g Grapefruit Type 1 specific Citrus X paradisi 37656 1.132857 2.35 0.35 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Green tea Type 1 0.0 0.0 0.0 mg/100 g Green vegetables Unknown generic Hazelnut Type 1 specific Corylus 13450 0.0 0.0 0.0 mg/100 g Herbs and Spices Unknown generic Italian oregano Type 1 specific Origanum X majoricum 1384207 0.0 0.0 0.0 mg/100 g Italian sweet red pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 0.0 0.0 0.0 mg/100 g Lemon Type 1 specific Citrus limon 2708 18.225 27.9 13.43 mg/100 g Lemon balm Type 1 specific Melissa officinalis 39338 0.0 0.0 0.0 mg/100 g Lettuce Type 1 specific Lactuca sativa 4236 0.0 0.0 0.0 mg/100 g Lime Type 1 specific Citrus aurantiifolia 159033 43.0 43.0 43.0 mg/100 g Lingonberry Type 1 specific Vaccinium vitis-idaea 180772 0.0 0.0 0.0 mg/100 g Lovage Type 1 specific Levisticum officinale 48042 0.0 0.0 0.0 mg/100 g Macadamia nut Type 1 specific Macadamia 4329 0.0 0.0 0.0 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 15.686667 22.01 7.94 mg/100 g Mentha Type 1 specific Mentha 21819 Muskmelon Type 1 specific Cucumis melo 3656 0.0 0.0 0.0 mg/100 g Nectarine Type 1 specific Prunus persica var. nucipersica 323851 0.0 0.0 0.0 mg/100 g Orange mint Type 1 specific Mentha aquatica 190902 Oxheart cabbage Type 1 specific Brassica oleracea var. conica 0.0 0.0 0.0 mg/100 g Parsley Type 1 specific Petroselinum crispum 4043 0.0 0.0 0.0 mg/100 g Peach Type 1 specific Prunus persica 3760 0.0 0.0 0.0 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 0.0 0.0 0.0 mg/100 g Pear Type 1 specific Pyrus communis 23211 0.0 0.0 0.0 mg/100 g Pecan nut Type 1 specific Carya illinoinensis 32201 0.0 0.0 0.0 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Peppermint Type 1 specific Mentha X piperita 34256 10.16 10.16 10.16 mg/100 g Persian lime Type 1 specific Citrus latifolia 200541 25.985 43.0 8.97 mg/100 g Pineapple Type 1 specific Ananas comosus 4615 0.0 0.0 0.0 mg/100 g Pistachio Type 1 specific Pistacia vera 55513 0.0 0.0 0.0 mg/100 g Potato Type 1 specific Solanum tuberosum 4113 0.0 0.0 0.0 mg/100 g Prunus (Cherry, Plum) Type 1 specific Prunus 3754 0.0 0.0 0.0 mg/100 g Pummelo Type 1 specific Citrus maxima 37334 5.095 8.4 1.79 mg/100 g Radish Type 1 specific Raphanus sativus 3726 0.0 0.0 0.0 mg/100 g Rapini Type 1 specific Brassica ruvo 1204434 0.0 0.0 0.0 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 0.0 0.0 0.0 mg/100 g Redcurrant Type 1 specific Ribes rubrum 175228 0.0 0.0 0.0 mg/100 g Rosemary Type 1 specific Rosmarinus officinalis 39367 0.0 0.0 0.0 mg/100 g Rubus (Blackberry, Raspberry) Type 1 specific Rubus 23216 0.0 0.0 0.0 mg/100 g Sausage Type 2 specific 0.0 0.0 0.0 mg/100 g Savoy cabbage Type 1 specific Brassica oleracea var. sabauda 1216010 0.0 0.0 0.0 mg/100 g Strawberry Type 1 specific Fragaria X ananassa 3747 0.0 0.0 0.0 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 0.0 0.0 0.0 mg/100 g Sweet cherry Type 1 specific Prunus avium 42229 0.0 0.0 0.0 mg/100 g Sweet orange Type 1 specific Citrus sinensis 2711 18.857778 33.600000381 9.0 mg/100 g Tarragon Type 1 specific Artemisia dracunculus 72341 0.0 0.0 0.0 mg/100 g Tea Type 1 specific Camellia sinensis 4442 0.0 0.0 0.0 mg/100 g Vaccinium (Blueberry, Cranberry, Huckleberry) Type 1 specific Vaccinium 13749 0.0 0.0 0.0 mg/100 g Watercress Type 1 specific Rorippa nasturtium-aquaticum 135518 0.0 0.0 0.0 mg/100 g Watermelon Type 1 specific Citrullus lanatus 3654 0.0 0.0 0.0 mg/100 g Welsh onion Type 1 specific Allium fistulosum 35875 0.007 0.007 0.007 mg/100 g Wild celery Type 1 specific Apium graveolens 4045 0.0 0.0 0.0 mg/100 g Yellow bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g bitter Sterol O-acyltransferase 1 P35610 SOAT1 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti feedant 275 Anti lipolytic 406 Anti-oxidant 502 A 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. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Fungistat 942 Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.