A flavonol glycoside and an active metabolite of kaempferol with diverse biological activities
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Parent Compound(s)
11852Kaempferol
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Kaempferol 3-glucuronide

Item No. 34645

Technical Information
Formal Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosiduronic acid
CAS Number
22688-78-4
Synonyms
  • Kaempferol 3-O-β-glucuronide
Molecular Formula
C21H18O12
Formula Weight
Purity
≥95%
A solid
λmax
268, 354 nm
SMILES
O=C(C(O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)C(O)=O)=C(C2=CC=C(C=C2)O)OC3=CC(O)=C4)C3=C4O
InChi Code
InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14-,15-,16+,19-,21+/m0/s1
InChi Key
FNTJVYCFNVUBOL-ZUGPOPFOSA-N
Origin
Plant/Styphnolobium japonicum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Kaempferol 3-glucuronide is a flavonol glycoside that has been found in Fragaria and an active metabolite of kaempferol (Item No. 11852) that has diverse biological activities.1,2,3,4 It is formed from kaempferol primarily in the small intestine.2 Kaempferol 3-glucuronide (0.1, 1, and 10 µM) induces Akt activity in mouse liver homogenates and increases glucose consumption in HepG2 cells.3 It inhibits the production of reactive oxygen species (ROS) induced by fMLP (Item No. 21495) in isolated human neutrophils when used at concentrations of 1 and 10 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ryan, J.J. Flavonol glycosides of the cultivated strawberry. J. Food Sci. 36(6), 867-870 (1971).

    2. Zheng, L., Zhu, L., Zhao, M., et alIn vivo exposure of kaempferol is driven by phase II metabolic enzymes and efflux transporters. AAPS J. 18(5), 1289-1299 (2016).

    3. Fang, G., Cheng, C., Zhang, M., et alThe glucuronide metabolites of kaempferol and quercetin, targeting to the AKT PH domain, activate AKT/GSK3β signaling pathway and improve glucose metabolism. J. Funct. Foods 82, 104501 (2021).

    4. Granica, S., Czerwińska, M.E., Żyżyńska-Granica, B., et alAntioxidant and anti-inflammatory flavonol glucuronides from Polygonum aviculare L. Fioterapia 91, 180-188 (2013).