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60010

Sigma-Aldrich

Kaempferol

≥97.0% (HPLC)

Synonym(s):

3,4′,5,7-Tetrahydroxyflavone, 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Robigenin

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About This Item

Empirical Formula (Hill Notation):
C15H10O6
CAS Number:
520-18-3
Molecular Weight:
286.24
Beilstein:
304401
MDL number:
MFCD00016938
UNSPSC Code:
12352205
PubChem Substance ID:
57651711
NACRES:
NA.47

Assay

≥97.0% (HPLC)

impurities

≤12% water

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

Oc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(O)cc3O2

InChI

1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H

InChI key

IYRMWMYZSQPJKC-UHFFFAOYSA-N

Gene Information

human ... CDC2(983) , CDK5(1020) , CDK6(1021) , CYP1A2(1544) , CYP2C9(1559) , GSK3A(2931)
mouse ... Hexa(15211)

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General description

Kaempferol is a polyphenolic antioxidant abundantly present in vegetables and fruits. It has a diphenylpropane structure. In many plants, it is present as a glycosidic form namely, kaempferol-3-O-glucoside.

Application

Kaempferol has been used:
  • to test its effect on osteoblast proliferation, migration, and differentiation in mouse pre-osteoblast cell line (MC3T3-E1 cells)
  • as an antioxidant and a hepatoprotective agent against zearalenone (ZEA)-induced oxidative stress and apoptosis in HEPG2 cells
  • as a neuroprotective agent against cadmium chloride (CdCl2) induced hippocampal damage and memory deficits in rats
  • as an anti-inflammatory agent, together with apigenin, for stem-cell therapy on knee osteoarthritic male rats

Chromogenic reagent for antimony in the low ppm range and for gallium and indium in the sub-ppm range.

Biochem/physiol Actions

Kaempferol is hydrophobic in nature due to its diphenylpropane group. It exerts anti-inflammatory actions along with their antioxidant properties and modulates pro-inflammatory enzyme activities. Kaempferol acts as a chemopreventive agent by exerting protective effects on cell viability. It modulates several key elements of cellular signal transduction pathways linked to apoptosis, angiogenesis, metastasis, and inflammation.
Potent inhibitor of osteoclastic bone resorption. The effect is believed to be attributable to both the antioxidant and estrogenic activities of kaempferol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kaempferol protects against cadmium chloride-induced hippocampal damage and memory deficits by activation of silent information regulator 1 and inhibition of poly (ADP-Ribose) polymerase-1
El-kott A F, et al.,
The Science of the Total Environment, 138832-138832 (2020)
Kasi Pandima Devi et al.
Pharmacological research, 99, 1-10 (2015-05-20)
Inflammation is an important process of human healing response, wherein the tissues respond to injuries induced by many agents including pathogens. It is characterized by pain, redness and heat in the injured tissues. Chronic inflammation seems to be associated with
Firoozeh Estakhri et al.
The Knee, 27(3), 817-832 (2020-04-28)
Based on the anti-inflammatory and anti-oxidant properties of kaempferol and apigenin, we hypothesized that co-injection of these phytochemicals would increase the effectiveness of cell therapy in knee osteoarthritic rats. Anterior cruciate ligament transection (ACLT) was used to induce osteoarthritis (OA).
Jean-Baptiste Daskiewicz et al.
Journal of medicinal chemistry, 48(8), 2790-2804 (2005-04-15)
A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation
Gil Fraqueza et al.
Dalton transactions (Cambridge, England : 2003), 41(41), 12749-12758 (2012-09-13)
Recently we demonstrated that the decavanadate (V(10)) ion is a stronger Ca(2+)-ATPase inhibitor than other oxometalates, such as the isoelectronic and isostructural decaniobate ion, and the tungstate and molybdate monomer ions, and that it binds to this protein with a
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