Compound: quercitrin
SMILES: O=c1c(O[C@@H]2O[C@H]([C@H](O)[C@H]([C@H]2O)O)C)c(oc3c1c(O)cc(c3)O)-c4cc(O)c(O)cc4
InChIKey: OXGUCUVFOIWWQJ-HQBVPOQASA-N
Synonyms: quercitrin, 522-12-3, Quercitroside, Quercetin 3-rhamnoside, Quercetrin, Quercimelin, Thujin, Quercetin-3-L-rhamnoside, Quercetin 3-L-rhamnoside, Usaf cf-2, Rhamnoside, quercetin-3, QUERCETIN 3-RHAMNOPYRANOSIDE, C.I. 75720, Quercetin 3-O-alpha-rhamnopyranoside, 3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnoside, CHEBI:17558, DTXSID50200230, 2Y8906LC5P, NCI-C60102, Quercetin, 3-(6-deoxy-alpha-L-mannopyranoside), Mannopyranoside, quercetin-3 6-deoxy-, alpha-L-, CI 75720, NSC-9221, Flavone, 3,3',4',5,7-pentahydroxy-, 3-rhamnoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one, WA 17779, Flavone, 3,3',4',5,7-pentahydroxy-, 3-(6-deoxy-alpha-L-mannopyranoside), 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one, 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, quercetin-3-O-alpha-rhamnosid, quercetin-3-O-alpha-rhamnoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)-4H-chromen-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one, RefChem:6191, DTXCID50122721, 208-322-5, Quercetin 3-O-rhamnoside, Quercetin-3-rhamnoside, Quercitronic acid, Quercetin 3-O-alpha-L-rhamnoside, Quercetin 3-O-L-rhamnoside, Quercetin 3-O-rhamnopyranoside, Quercetin 3-O-alpha-L-rhamnopyranoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one, MFCD00016932, Quercetin-3-O-rhamnoside, NSC9221, Rhamnosyl-3-quercitin, Quercitin-3-rhamnoside, luteolin 6-deoxy-alpha-L-mannopyranoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one, 4H-1-Benzopyran-4-one, 3-((6-deoxy-.alpha.-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, Quercetrin-3-O-rham, CHEMBL82242, quericitrin, UNII-2Y8906LC5P, Quercetin 3-O-.alpha.-L-rhamnoside, Quercitrin CRS, HSDB 4339, 4gue, OXGUCUVFOIWWQJ-HQBVPOQASA-N, quercetin rhamnoside, 4H-1-Benzopyran-4-one, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, EINECS 208-322-5, Quercitrin (Standard), BRN 0068135, quercetin-3-O-rhamnose, QUERCITRIN [MI], AI3-36095, QUERCITRIN [HSDB], quercetin-3-o-l-rhamnoside, BIDD:PXR0076, Quercetin 3-?-L-rhamnoside, 5-18-05-00514 (Beilstein Handbook Reference), MLS002472998, 3-O-RHAMNOSYLQUERCETIN, SCHEMBL147092, MEGxp0_000185, orb1304907, orb3139992, quercetin-3-o-beta-d-rhamnoside, SCHEMBL29381705, SCHEMBL29454400, ACon1_000189, BDBM84978, cid_5280459, HY-N0418R, quercetin-3-o-alpha-l-rhamnoside, WLZ4720, quercetin-3-O-alpha-L-rahmnoside, 3-O-(alpha-L-rhamnosyl)quercetin, HMS2219D24, HMS6018H12, HY-N0418, MSK40260, quercetin-3-O-a-L-rhamnopyranoside, quercetin-3-alpha-l-rhamnopyranoside, BDBM50056315, quercetin 3-O-alpha-L-rhampyranoside, s3824, AKOS000278033, CCG-269215, CS-5408, EBC-427042, MQ08116, SMP1_000253, 3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydr oxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, AC-20295, AC-34266, BS-16996, QUERCETIN-3-O-.ALPHA.-RHAMNOSIDE, SMR001397103, NS00006156, 3-O-.ALPHA.-L-RHAMNOPYRANOSYLQUERCETIN, C01750, QUERCETIN 3-O-.ALPHA.-RHAMNOPYRANOSIDE, QUERCETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE, Q1649777, Quercitrin, primary pharmaceutical reference standard, BRD-K98601533-001-01-7, Flavone, 3,3',4',5, 7-pentahydroxy-, 3-rhamnoside, 5,7,3',4'-TETRAHYDROXYFLAVONOL 3-O-RHAMNOSIDE, 3,3',4',5,7-PENTAHYDROXYFLAVONE 3-L-RHAMNOSIDE, 3-O-a-L-Rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavone, QUERCITRIN (QUERCETIN-3-O- RHAMNOSIDE) (CONSTITUENT OF GINKGO) [DSC], 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxy-alpha-L-mannopyranoside, 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-deoxy-.alpha.-L-mannopyranoside, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-1-BENZOPYRAN-4-ONE, 3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one, 3-[(6-Deoxy-?-L-mannopyranosyl)-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Theoretical properties:
molecular_formula: C21H20O11
molecular_weight: 448.4 g/mol
exact_mass: 448.10056145 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 3
heavy_atom_count: 32
topological_polar_surface_area: 186 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: YELLOW CRYSTALS FROM DIL METHANOL OR ETHANOL
color: YELLOW CRYSTALS FROM DIL METHANOL OR ETHANOL
melting_point: 176-179 °C; FROM WATER, MP 167 °C
solubility: PRACTICALLY INSOL IN COLD WATER, ETHER; SOL IN ALCOHOL; MODERATELY SOL IN HOT WATER; SOL IN AQ ALKALINE SOLN
Descriptions:
pubchem: Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor and a plant metabolite. It is an alpha-L-rhamnoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate.
chebi: A quercetin <em>O</em>-glycoside that is quercetin substituted by a α-<small>L</small>-rhamnosyl moiety at position 3 via a glycosidic linkage.
chembl: QUERCITRIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.
Austrian chemist Heinrich Hlasiwetz (1825-1875) is remembered for his chemical analysis of quercitrin.
It has also been investigated as a potential dietary supplement.