| Identification | Back Directory | [Name]
QUERCETIN-3-O-GLUCURONIDE | [CAS]
22688-79-5 | [Synonyms]
CS-149
Mikwelianin
Miquelianin
Quercituron
Querciturone
Miquelianin?, >99%
Quercetin 3-O-ß
Quercetol glucuronide
Quercetol 3-glucuronide
Quercetol 3-O-glucuronide
Quercetin 3-D-glucuronide
Quercetin 3-O-β-D-glucuronide
QUERCETIN-3-O-GLUCURONIDE(RG)
Quercetin 3-glucuronide ,>=99%
Quercetin 3-O-β-D-Glucuronopyranoside
Miquelianin (Quercetin 3-O-glucuronide)
3,3′,4′,5,7-Pentahydroxyflavone 3-glucuronide
QUERCETIN 3-O-GLUCURONIDE; QUERCETIN 3-GLUCURONIDE
Quercetin 3-glucuronide, 98%, from Bupleurum chinense DC.
3',4',5,7-Tetrahydroxyflavon-3-yl β-D-glucopyranosiduronic acid
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(β-D-glucopyranuronosyloxy)-4H-1-benzopyran-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl β-D-Glucopyranosiduronic Acid
b-D-Glucopyranosiduronic acid,2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
β-D-Glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl-beta-D-glucopyranosiduronic acid | [Molecular Formula]
C21H18O13 | [MDL Number]
MFCD04039814 | [MOL File]
22688-79-5.mol | [Molecular Weight]
478.36 |
| Chemical Properties | Back Directory | [Melting point ]
193～195℃ | [Boiling point ]
927.8±65.0 °C(Predicted) | [density ]
1.96±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
2.76±0.70(Predicted) | [color ]
Yellow to Very Dark Yellow | [Stability:]
Very Hygroscopic | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChIKey]
DUBCCGAQYVUYEU-UVXHTARINA-N | [SMILES]
O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](C(=O)O)O1)O)C1C(C2=C(C=C(O)C=C2OC=1C1C=CC(O)=C(O)C=1)O)=O |&1:1,2,3,5,7,r| | [LogP]
2.100 (est) |
| Hazard Information | Back Directory | [Description]
Quercetin 3-O-glucuronide is a pharmacologically active flavonol glucuronide isolated from H. perforatum (St. John’s wort) that inhibits the α2c adrenergic receptor (Ki = 4,060 nM in hα2c preparations).1,2,3 Quercetin 3-O-glucuronide (0.6 mg/kg) reduced the time rats spent immobile in the forced swim test, suggesting antidepressant-like properties, when given either acutely or chronically.4 It also reduced open field stress-induced hyperthermia in mice (at 1.2 mg/kg).5 | [Chemical Properties]
Yellow Solid | [Uses]
Quercetin 3-O-β-D-Glucuronide is the major metabolite of Quercetin (Q509500). | [Definition]
ChEBI: Miquelianin is a quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities. It has a role as a metabolite, an antioxidant and an antidepressant. It is a beta-D-glucosiduronic acid and a quercetin O-glycoside. | [Synthesis]
Overnight cultures of E. coli containing specific genes were inoculated into 50 mL of fresh LB medium containing appropriate antibiotics. Isopropyl β-D-1-thiogalactopyranoside (IPTG) was added to the mixture to a final concentration of 1 mM. the transform | [in vivo]
Miquelianin treatment, compared to vehicle-control treatment, significantly improves AD-type deficits in hippocampal formation basal synaptic transmission and long-term potentiation[3]. | [References]
[1] A NAHRSTEDT V B. Biologically active and other chemical constituents of the herb of Hypericum perforatum L.[J]. Pharmacopsychiatry, 1997, 30 Suppl 2: 129-134. DOI: 10.1055/s-2007-979533
[2] ADOLF NAHRSTEDT* Veronika B. Lessons Learned from Herbal Medicinal Products: The Example of St. John’s Wort⊥[J]. Journal of Natural Products , 2010, 73 5: 1015-1021. DOI: 10.1021/np1000329
[3] V BUTTERWECK. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test.[J]. Planta medica, 2000, 66 1: 3-6. DOI: 10.1055/s-2000-11119
[4] OLIVER GRUNDMANN Veronika B Olaf Kelber. Effects of St. John’s wort extract and single constituents on stress-induced hyperthermia in mice.[J]. Planta medica, 2006, 72 15: 1366-1371. DOI: 10.1055/s-2006-951710 |
|
|