A flavonol glucuronide inhibitor of the α2c adrenergic receptor
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Quercetin 3-O-glucuronide

Item No. 21289

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-ylβ-D-glucopyranosiduronic acid
CAS Number
22688-79-5
Synonyms
  • Miquelianin
  • Quercetin 3-O-β-D-glucuronide
Molecular Formula
C21H18O13
Formula Weight
478.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
258, 363 nm
SMILES
OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O2)=C(C3=CC=C(O)C(O)=C3)O4)=O)C4=C1
InChi Code
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChi Key
DUBCCGAQYVUYEU-ZUGPOPFOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nahrstedt, A., and Butterweck, V. Biologically active and other chemical constituents of the herb of Hypericum perforatum L. Pharmacopsychiatry 30(Suppl 2), 129-134 (1997).

    2. Nahrstedt, A., and Butterweck, V. Lessons learned from herbal medicinal products: The example of St. John’s Wort. J. Nat. Prod. 73(5), 1015-1021 (2010).

    3. Butterweck, V., Jürgenliemk, G., Narstedt, A., et al. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 66(1), 3-6 (2000).

    4. Grundmann, O., Kelber, O., and Butterweck, V. Effects of St. John’s wort extract and single constituents on stress-induced hyperthermia in mice. Planta Med. 72(15), 1366-1371 (2006).