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60010

Sigma-Aldrich

Kaempferol

≥97.0% (HPLC)

Synonym(s):
Robigenin, 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 3,4′,5,7-Tetrahydroxyflavone
Empirical Formula (Hill Notation):
C15H10O6
CAS Number:
Molecular Weight:
286.24
Beilstein:
304401
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

assay

≥97.0% (HPLC)

impurities

≤12% water

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

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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

Potent inhibitor of osteoclastic bone resorption. The effect is believed to be attributable to both the antioxidant and estrogenic activities of kaempferol.
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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 60010.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

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

Certificate of Analysis

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Certificate of Origin

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Teresa Tarragó et al.
Bioorganic & medicinal chemistry, 16(15), 7516-7524 (2008-07-25)
Prolyl oligopeptidase is a cytosolic serine peptidase that hydrolyzes proline-containing peptides at the carboxy terminus of proline residues. It has been associated with schizophrenia, bipolar affective disorder, and related neuropsychiatric disorders and therefore may have important clinical implications. In a
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
Allen Y Chen et al.
Food chemistry, 138(4), 2099-2107 (2013-03-19)
Kaempferol is a polyphenol antioxidant found in fruits and vegetables. Many studies have described the beneficial effects of dietary kaempferol in reducing the risk of chronic diseases, especially cancer. Epidemiological studies have shown an inverse relationship between kaempferol intake and
Radka Václavíková et al.
Bioorganic & medicinal chemistry, 16(4), 2034-2042 (2007-11-21)
This study investigated the effect of naturally occurring flavonoids and synthetic aurone derivatives on the formation of cardiotoxic doxorubicinol and transport of doxorubicin in breast cancer cells. Quercetin significantly inhibited the formation of doxorubicinol. Quercetin and aurones did not significantly

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