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Merck

60010

Kaempferol

≥97.0% (HPLC)

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C15H10O6
Número CAS:
520-18-3
Peso molecular:
286.24
UNSPSC Code:
12352205
NACRES:
NA.47
PubChem Substance ID:
57651711
MDL number:
MFCD00016938
Beilstein/REAXYS Number:
304401

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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

SMILES string

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

InChI key

IYRMWMYZSQPJKC-UHFFFAOYSA-N

assay

≥97.0% (HPLC)

impurities

≤12% water

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

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

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

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.

signalword

Warning

Clase de almacenamiento

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

pictograms

Health hazardExclamation mark
GHS08,GHS07

Hazard Classifications

Eye Irrit. 2 - Muta. 2 - Skin Irrit. 2

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Certificados de análisis (COA)

Lot/Batch Number
BCCN6952
BCCN4449
BCCN0036
BCCL7217
BCCK3585

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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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