1.0 2010-04-08 22:09:57 UTC 2019-11-26 03:06:01 UTC FDB012030 Taxifolin 3-rhamnoside Constituent of Vitis vinifera (wine grape) Astilbin is a flavanonol, a type of flavonoid. It can be found in St John's wort (Hypericum perforatum, Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in Dimorphandra mollis (Fava d'anta, Fabaceae), in the the leaves of Harungana madagascariensis (Hypericaceae), in the rhizome of Astilbe thunbergii, in the root of Astilbe odontophylla(Saxifragaceae) and in the rhizone of Smilax glabra (Chinaroot, Smilacaceae). (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one (2R,3R)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one (2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one (2R,3R)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one Astilbin Dihydroquercetin-3-O-a-lrhap Dihydroquercetin-3-O-alpha-lrhap Dihydroquercetin-3-O-α-lrhap Taxifolin 3-O-a-L-rhamnopyranoside Taxifolin 3-O-a-L-rhamnoside Taxifolin 3-rhamnoside C21H22O11 450.3928 450.116211546 (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one astilbin 29838-67-3 C[C@@H]1O[C@@H](O[C@@H]2[C@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 ZROGCCBNZBKLEL-MPRHSVQHSA-N belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Flavonoid-3-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Acetals Alkyl aryl ethers Aryl alkyl ketones Benzene and substituted derivatives Catechols Chromones Flavanonols Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Polyols Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Catechol Chromane Chromone Ether Flavan Flavanone Flavanonol Flavonoid-3-o-glycoside Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Ketone Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Polyol Secondary alcohol Vinylogous acid 3'-hydroxyflavanones alpha-L-rhamnoside flavanone glycoside monosaccharide derivative tetrahydroxyflavanone logp 0.79 ALOGPS logs -2.09 ALOGPS solubility 3.64e+00 g/l ALOGPS melting_point Mp 179-180° logp 1.09 ChemAxon pka_strongest_acidic 7.74 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 450.3928 ChemAxon mono_mass 450.116211546 ChemAxon smiles C[C@@H]1O[C@@H](O[C@@H]2[C@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C21H22O11 ChemAxon inchi InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 ChemAxon inchikey ZROGCCBNZBKLEL-MPRHSVQHSA-N ChemAxon polar_surface_area 186.37 ChemAxon refractivity 105.48 ChemAxon polarizability 42.86 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 317321 Specdb::NmrOneD 317322 Specdb::NmrOneD 317323 Specdb::NmrOneD 317324 Specdb::NmrOneD 317325 Specdb::NmrOneD 317326 Specdb::NmrOneD 317327 Specdb::NmrOneD 317328 Specdb::NmrOneD 317329 Specdb::NmrOneD 317330 Specdb::NmrOneD 317331 Specdb::NmrOneD 317332 Specdb::NmrOneD 317333 Specdb::NmrOneD 317334 Specdb::NmrOneD 317335 Specdb::NmrOneD 317336 Specdb::NmrOneD 317337 Specdb::NmrOneD 317338 Specdb::NmrOneD 317339 Specdb::NmrOneD 317340 Specdb::MsMs 84156 Specdb::MsMs 84157 Specdb::MsMs 84158 Specdb::MsMs 145929 Specdb::MsMs 145930 Specdb::MsMs 145931 Specdb::MsMs 440516 Specdb::MsMs 440517 Specdb::MsMs 452215 Specdb::MsMs 2320631 Specdb::MsMs 2320632 Specdb::MsMs 2320633 Specdb::MsMs 2614105 Specdb::MsMs 2614106 Specdb::MsMs 2614107 Specdb::CMs 17786 Specdb::CMs 43537 Specdb::CMs 146250 HMDB33850 38200 #<Reference:0x000055ce307418b0> Alcoholic beverages Unknown generic Common grape Type 1 specific Vitis vinifera 29760 Fruits Unknown generic Grape wine Type 2 specific 0.54173 0.970600001 0.270590907 mg/100 g Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).