QUERCETIN-3-O-GLUCURONIDE Chemical Properties

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 

Solid

pka

2.76±0.70(Predicted)

color 

Yellow to Very Dark Yellow

Stability:

Very Hygroscopic

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)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

QUERCETIN-3-O-GLUCURONIDE Usage And Synthesis

Description

Quercetin 3-O-glucuronide is a pharmacologically active flavonol glucuronide isolated from H. perforatum (St. John’s wort) that inhibits the α_2c adrenergic receptor (K_i = 4,060 nM in hα_2c preparations). 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. It also reduced open field stress-induced hyperthermia in mice (at 1.2 mg/kg).

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.

in vivo

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

QUERCETIN-3-O-GLUCURONIDE(22688-79-5)Related Product Information

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