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 18??C. 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 25??C 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 30??C 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