Kaempferol

Kaempferol Basic information
Pharmacological effects Mechanism of action Bioactivity
Product Name:Kaempferol
Synonyms:3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-on;5,7,4’-trihydroxyflavonol;c.i.75640;campherol;indigoyellow;kaempherol;kampherol;kempferol
CAS:520-18-3
MF:C15H10O6
MW:286.24
EINECS:208-287-6
Product Categories:Flavanols;Tetra-substituted Flavones;Biochemistry;Natural Plant Extract;Tyrosine Kinase Inhibitors;Signalling;Flavonoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors
Mol File:520-18-3.mol
Kaempferol Structure
Kaempferol Chemical Properties
Melting point 276°C
Boiling point 348.61°C (rough estimate)
density 1.2981 (rough estimate)
refractive index 1.4413 (estimate)
storage temp. 2-8°C
solubility ethanol: 20 mg/mL
pka6.34±0.40(Predicted)
form powder
Colour Index 75640
color yellow
Merck 14,5274
BRN 304401
Stability:Unstable in Solution
InChIKeyIYRMWMYZSQPJKC-UHFFFAOYSA-N
LogP2.685 (est)
CAS DataBase Reference520-18-3(CAS DataBase Reference)
IARC3 (Vol. 31, Sup 7) 1987
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38-68-25
Safety Statements 26-36-45-36/37-36/37/38-22
RIDADR 2811
WGK Germany -
RTECS LK9275200
8-10-23
HS Code 29329990
Hazardous Substances Data520-18-3(Hazardous Substances Data)
MSDS Information
ProviderLanguage
3,4',5,7-Tetrahydroxyflavone English
SigmaAldrich English
Kaempferol Usage And Synthesis
Pharmacological effects

Kaempferol (3,5,7‐trihydroxy‐2‐[4‐hydroxyphenyl]‐4H‐1‐benzopyran‐4‐one) is a yellow bioactive flavonoid, which is present inmany edible plants such as tea, cabbage, broccoli, endive, kale, beans, tomato, strawberries, leek, and grapes. It has a significant role in reducing cancer and can act as a therapeutic agent in the treatment of diseases and ailments such as diabetes, obesity, cardiovascular diseases, oxidative stress, asthma, and microbial contamination disorders. Its efficacy, a broad range of activity, and low toxicity compared with other examined compounds, make it an attractive chemical in the fight against diseases (including cancer).

Mechanism of action

Kaempferol acts through different mechanisms: It induces apoptosis (HeLa cervical cancer cells), decreases cell viability (G2/M phase), downregulates phosphoinositide 3‐kinase (PI3K)/AKT (protein kinase B) and human T‐cell leukemia/lymphoma virus‐I (HTLV-I) signaling pathways, suppresses protein expression of epithelial‐mesenchymal transition (EMT)‐related markers including N‐cadherin, E‐cadherin, Slug, and Snail, and metastasis‐related markers such as matrix metallopeptidase 2 (MMP-2).

Bioactivity

As an anti‐oxidant, kaempferol counteracts production of superoxide ions and lowers the formation of reactive oxygen and nitrogen species. It also scavenges Fenton‐generated hydroxyl radical, peroxynitrite, and hydroxyl radicals. Furthermore, kaempferol suppresses the activity of xanthine oxidase and enhances the activities of catalase, heme oxygenase‐1, and superoxide dismutase.

Chemical PropertiesYellow Solid
Usesantidepressant, inhibits fatty acid amide hydrolase
UsesKaempferol, is used as an inhibitor of Fatty Acid Synthase, Cox-1 activity, and Topo I. It also Induces caspase-9-mediated apoptosis in a variety of cancer cell lines via downregulation of polo-like kinase 1 (PLK1) expression. Exhibits antioxidant activity and attenuates osteoclastic bone reabsorption in vitro. Also blocks EGF-induced histone H3Ser10 phosphorylation in mouse epidermal JB6 C141 cells.
UsesChromogenic reagent for antimony in the low ppm range and for gallium and indium in the sub-ppm range.
DefinitionChEBI: Kaempferol is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4'. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. It has a role as an antibacterial agent, a plant metabolite, a human xenobiotic metabolite, a human urinary metabolite, a human blood serum metabolite and a geroprotector. It is a member of flavonols, a 7-hydroxyflavonol and a tetrahydroxyflavone. It is a conjugate acid of a kaempferol oxoanion.
General DescriptionKaempferol 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.
Biological ActivityNaturally occurring flavonoid found in Gingko biloba and red wines that activates the mitochondrial Ca 2+ uniporter (EC 50 = 7 μ M). Induces caspase-9-mediated apoptosis in a variety of cancer cell lines via downregulation of polo-like kinase 1 (PLK1) expression. Exhibits antioxidant activity and attenuates osteoclastic bone reabsorption in vitro .
Biochem/physiol ActionsPotent inhibitor of osteoclastic bone resorption. The effect is believed to be attributable to both the antioxidant and estrogenic activities of kaempferol.
Anticancer ResearchKaempferol is one of the secondary metabolites found in some plants, plant-derivedfoods, and traditional medicines. It is a flavonoid compound obtained from someedible plants including grapes, tea, strawberries, broccoli, tomato, cabbage, leek,kale, endive, and beans. It inhibits growth and migration of pancreatic cancer cellsby acting on proto-oncogene tyrosine kinase (Src), ERK1/2, and AKT pathways(Singh et al. 2016a). It is being investigated in pancreatic and lung cancers toevaluate its antiangiogenic, anticancer, and radical scavenging activities. It showsmoderate cytostatic activity in PC3, HeLa, and K562 human cancer cells. It isidentified as aryl hydrocarbon receptor antagonist and acts against ABCG2 (ATP-bindingcassette subfamily G member 2)-mediated multidrug resistance bypreventing the ABCG2 upregulation in esophageal carcinoma. It induces theapoptosis of ovarian cancer cell by activating p53 in intrinsic pathway mechanism.It is an inhibitor of breast cancer resistance protein (BCRP), quinine reductase-2,and a substrate of BCRP (Calderon-Montano et al. 2011; Wang et al. 2012).
storageStore at +4°C
Kaempferol Preparation Products And Raw materials
Preparation ProductsIcariin-->Desmethylanhydroicaritin-->KAEMPFEROL-7-O-GLUCOSIDE-->Kaempferol 3-O-D-galactoside
ARTEMISININ Robinin MORIN Isorhamnetin 3,7,3',4'-TETRAMETHYLGOSSYPETIN AVICULARIN Quercetin 3,7-DIMETHOXY-3',4',5-TRIHYDROXYFLAVONE Isoflavone Myricitrin TAMARIXETIN-7-O-RUTINOSIDE Kaempferol FLAVONE Rutin QUERCETIN-3,7,3',4'-TETRAMETHYL ETHER 7-HYDROXYFLAVONE Hyperoside ISOFLAVONES

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