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

• ChemBase编号: 1622
• 分子式: C15H10O6
• 平均质量: 286.2363
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC传统名: kaempherol; kaempferol
• 别名: 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

登记号

• CAS号: 520-18-3; 520-18-3
• EC号: 208-287-6
• MDL号: MFCD00016938
• Beilstein号: 304401
• PubChem SID: 24881773; 46507811; 160965079; 24896195
• PubChem CID: 5280863
• CHEMBL: 150
• Chemspider ID: 4444395
• KEGG ID: C05903
• 维基百科标题: Kaempferol

理论计算性质

JChem

• Acid pKa: 6.3798757
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): 2.4062753
• LogD (pH = 7.4): 1.3064047
• Log P: 2.4598649
• 摩尔折射率: 74.8813 cm^3
• 极化性: 27.760374 Å^3
• 极化表面积: 107.22 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.99
• LOG S: -3.21
• 溶解度: 1.78e-01 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble50 mg/mL; ethanol: soluble20 mg/mL; Methanol
• 外观: yellow powder; Yellow powder; Yellow Solid
• 熔点: 266-274°C; 276–278 °C; 283-286°C
• 密度: 1.688 g/mL

安全信息

• 保存条件: 0°C; -20°C; -20°C Freezer; protect from light
• 保存注意事项: Unstable in Solution
• RTECS编号: LK9275200
• 欧盟危险性物质标志: 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 25-68; R:22
• 安全公开号: 36/37-45; S:36/37/39
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H341
• GHS警示性声明: P281-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C; room temp

药理学性质

• 相关基因信息: human ... CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), CYP2C9(1559), GSK3A(2931)mouse ... Hexa(15211)

产品相关信息

• 纯度: ≥90% (HPLC); ≥97.0% (HPLC); ≥99.0% (HPLC); 98.5
• 级别: analytical standard
• 成盐信息: Free Base
• 杂质: ≤12% water
• 有效期: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H10O6

详细说明

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.

参考文献

• 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)