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

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)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

Storage Class

11 - Combustible Solids

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.

Synthesis

Overnight cultures of E. coli containing specific genes were inoculated into 50 mL of fresh LB medium containing appropriate antibiotics. Isopropyl -D-1-thiogalactopyranoside (IPTG) was added to the mixture to a final concentration of 1 mM. the transformants were incubated for an additional 20 h at 18C. The cells were then incubated with the antibiotic for a further 20 h. The transformants were then incubated with the antibiotic. Cells were harvested by centrifugation and resuspended in fresh M9 medium containing 2% glucose and antibiotics and 1 mM isopropyl -D-1-thiogalactopyranoside. The cell density was adjusted to an OD600 value of 2. A total reaction volume of 2 mL was maintained in a test tube (14 mm x 145 mm). one hundred micromoles of lignocaine was added to the reaction mixture. The mixture was incubated at 25C for 1.5 hrs. An additional 100 M lignocaine was added to the reaction mixture. The mixture was incubated for another 1.5 hours. 200 M lignocaine was added to the mixture to determine the optimal cell concentration. 2 hours later, another 200 M lignocaine was added to the mixture. The reaction mixture was incubated for 2 hours. The cell density was adjusted to an OD600 value of 3. 200 M quercetin was added to the reaction for 2 hours. One hundred micromoles of quercetin was added to the mixture. The mixture was shaken at 30C for 1.5 h to obtain 2-(3,4dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl-BETA-D-glucopyranosiduronic acid

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

• quercetin 3-sambubioside
• 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one
• MEDICAGOL
• Isofraxidin
• Quercetin-7-O-β-D-glucopyranoside
• 4',5-DIHYDROXY-7-METHOXYFLAVONE
• MOSLOFLAVONE
• hydroxygenkwanin
• Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
• Naringenin
• GARDENIN B
• PONCIRIN
• Quercetin 3-O-neohesperidoside
• Resorcinol
• 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic acid
• Dihydrocaffeic acid
• Diphenylphosphine oxide
• Quercetagetin-7-O-glucoside