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K0133

Sigma-Aldrich

Kaempferol

≥90% (HPLC), powder

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.25

Quality Level

biological source

synthetic

assay

≥90% (HPLC)

form

powder

storage condition

protect from light

color

yellow

mp

277 °C

solubility

ethanol: 20 mg/mL
DMSO: 50 mg/mL

storage temp.

room temp

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 natural dietary flavonoid and a polyphenol antioxidant found in various fruits and vegetables. Kaempferol is present in plants in a different glycosidic form such as astragalin by binding with different sugars.

Application

Kaempferol (KAE) has been used:
  • to check its potential effect as an antioxidant and neuroprotective agent against rotenone-induced Parkinson′s disease (PD) model in SH-S5Y5 cells
  • to test its anti-inflammatory effect on lipopolysaccharide (LPS)-induced inflammatory injury in human aortic endothelial cells (HAECs)
  • to study its apoptosis sensitizing effect on non-small cell lung cancer (NSCLC) cells by inhibiting nuclear factor erythroid 2-related factor 2 (Nrf2)

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

Biochem/physiol Actions

The diphenylpropane component of Kaempferol contributes to its hydrophobic properties. It has shown to revert the transformed phenotype of phorbol ester-treated mouse fibroblasts or v-H-ras-transformed NIH 3T3 cells. Kaempferol induces significant nuclear DNA degradation concurrent with lipid peroxidation. It also inhibits topoisomerase I catalyzed DNA religation. Kaempferol may also inhibit the activity of fatty acid synthase.
Potent inhibitor of osteoclastic bone resorption. The effect is believed to be attributable to both the antioxidant and estrogenic activities of kaempferol.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. K0133.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

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

M L Kuo et al.
Cancer letters, 87(1), 91-97 (1994-11-25)
Fifteen flavonoids were employed to examine their effects on the morphological changes, foci formation in soft agar and cellular growth in v-H-ras-transformed NIH3T3 cells. The data presented here demonstrated that only three specific flavonoids--apigenin, kaempferol, and genistein--exhibited the reverting effect
F Boege et al.
The Journal of biological chemistry, 271(4), 2262-2270 (1996-01-26)
Topoisomerases are involved in many aspects of DNA metabolism such as replication and transcription reactions. Camptothecins, which stabilize the covalent intermediate of topoisomerase I and DNA are effective, though toxic, drugs for cancer therapy. In this study, a new class
S C Sahu et al.
Cancer letters, 85(2), 159-164 (1994-10-14)
The extent of DNA damage and lipid peroxidation induced by kaempferol, a polyphenolic flavonoid with a molecular structure similar to quercetin, was studied under aerobic conditions in isolated rat-liver nuclei. Kaempferol induced significant (P < 0.05) concentration-dependent nuclear DNA degradation
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

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