3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 1622
• Molecular Formular: C15H10O6
• Molecular Mass: 286.2363
• Monoisotopic Mass: 286.04773804
• SMILES: c1c(c2c(cc1O)oc(c(c2=O)O)c1ccc(cc1)O)O
• Canonical SMILES: Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O)O
• InChI: 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
• InChIKey: IYRMWMYZSQPJKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: kaempherol; kaempferol
• Synonyms: Kaempferol; Kaempherol; 3,4′,5,7-Tetrahydroxyflavone; 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Kaempferol; Kaempherol; Robigenin; Pelargidenolon; Rhamnolutein; Rhamnolutin; Populnetin; Trifolitin; Kempferol; Swartziol; 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 3,5,7-Trihydroxy-2-[4-hydroxy-phenyl]-4H-1-benzopyran-4-one; 3,4',5,7-Tetrahydroxyflavone; 3,4’,5,7-Tetrahydroxyflavone; NSC 407289; NSC 656277; Nimbecetin; Pelargidenon; Indigo Yellow

Database IDs

• CAS Number: 520-18-3; 520-18-3
• EC Number: 208-287-6
• MDL Number: MFCD00016938
• Beilstein Number: 304401
• PubChem SID: 24881773; 46507811; 160965079; 24896195
• PubChem CID: 5280863
• CHEMBL: 150
• Chemspider ID: 4444395
• KEGG ID: C05903
• Wikipedia Title: Kaempferol

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.3798757
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.4062753
• LogD (pH = 7.4): 1.3064047
• Log P: 2.4598649
• Molar Refractivity: 74.8813 cm^3
• Polarizability: 27.760374 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.99
• LOG S: -3.21
• Solubility (Water): 1.78e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble50 mg/mL; ethanol: soluble20 mg/mL; Methanol
• Apperance: yellow powder; Yellow powder; Yellow Solid
• Melting Point: 266-274°C; 276–278 °C; 283-286°C
• Density: 1.688 g/mL

Safety Information

• Storage Condition: 0°C; -20°C; -20°C Freezer; protect from light
• Storage Warning: Unstable in Solution
• RTECS: LK9275200
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 25-68; R:22
• Safety Statements: 36/37-45; S:36/37/39
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H341
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

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

Product Information

• Purity: ≥90% (HPLC); ≥97.0% (HPLC); ≥99.0% (HPLC); 98.5
• Grade: analytical standard
• Salt Data: Free Base
• Impurities: ≤12% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H10O6

DETAILS

MP Biomedicals - 02155143

(3,5,7-Trihydroxy-2-[4-hydroxy- phenyl]-4H-1-benzopyran-4-one; 3,4',5,7-Tetrahydroxyflavone) Yellow crystals.

MP Biomedicals - 05201074

MP Biomedicals Rare Chemical collection

DrugBank - DB01852

Drug information: experimental

Selleck Chemicals - S2314

Research Area: Neurological Disease
Biological Activity:
Kaempferol is a natural flavonol, a type of flavonoid, that has been isolated from plant sources. It is what gives the flowers of Acacia decurrens and Acacia longifolia their color. The compound has antidepressant properties. The enzyme kaempferol 4’-O-methyltransferase uses S-adenosyl methionine and kaempferol to produce S-adenosylhomocysteine and kaempferide. [1]

Sigma Aldrich - K0133

Application
Chromogenic reagent for antimony in the low ppm range2 and for gallium and indium in the sub-ppm range.3
Biochem/physiol Actions
A flavonol shown to revert the transformed phenotype of phorbol ester-treated mouse fibroblasts or v-H-ras-transformed NIH 3T3 cells. Induces significant nuclear DNA degradation concurrent with lipid peroxidation.4 Inhibits topoisomerase I catalyzed DNA religation.5 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.1

Sigma Aldrich - 60010

Application
Chromogenic reagent for antimony in the low ppm range2 and for gallium and indium in the sub-ppm range.3
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.1
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.

Sigma Aldrich - 96353

Application
Chromogenic reagent for antimony in the low ppm range2 and for gallium and indium in the sub-ppm range.3
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.1

Toronto Research Chemicals - K100000

Kaempferol is a plant flavonoid which play a beneficial role in human health promotion.

REFERENCES

• http://en.wikipedia.org/wiki/Kaempferol
• Hertog, M., et al.: Nutr. Cancer, 20, 21 (1993)
• Peluso, M., et al.: Carcinogenesis, 21, 183 (1993)
• Briggs, W., et al.: Plant Physiol., 125, 85 (1993)