Formononetin

Names

[ CAS No. ]:
485-72-3

[ Name ]:
Formononetin

[Synonym ]:
4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-methoxyphenyl)-
7-hydroxy-4'-methoxy-Isoflavone (8CI)
7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Formononetol
4'-O-methyl-daidzein
4H-1-Benzopyran-4-one, 7-hydroxy-3- (4-methoxyphenyl)-
BIOCHANIN B
ForMonentin
BIOCHANIN A
Flavosil
7-Hydroxy-4'-methoxyisoflavone
Neochanin
Myconate
MFCD00016948
BiocaninB
FORMONETIN
7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
EINECS 207-623-9
Formononetin
7-Hydroxy-3-(4-methoxyphenyl)chromone
forMonoetin

Biological Activity

[Description]:

Formononetin (Formononetol; Flavosil) is a bioactive component extracted from the red clover; inhibits the proliferation of DU-145/PC-3 cells in a dose-dependent manner.IC50 value:Target: anti-cancer in vitro: formononetin inhibited the proliferation of DU-145 cells in a dose-dependent manner. DU-145 cells treated with different concentrations of formononetin displayed obvious morphological changes of apoptosis under fluorescence microscopy. In addition, formononetin increased the proportion of early apoptotic DU-145 cells, down-regulated the protein levels of Bcl-2 and up-regulated those of RASD1 and Bax [1]. Formononetin significantly inhibited the cell growth of PC-3 in a dose-dependent manner, but no such effect was observed in RWPE1 cells. Formononetin treatment contributed to the reduced Bcl-2 protein level and the elevated Bax expression in PC-3 cells, thereby resulting in the increasing Bax/Bcl-2 ratios. Furthermore, the phosphorylated level of p38 in PC-3 cells was activated through the FN treatment, whereas the endogenous Akt phosphorylation was blocked [2]. Compared with the control, formononetin inhibited the proliferation of MCF-7 cells and effectively induced cell cycle arrest. The levels of p-IGF-1?R, p-Akt, cyclin D1 protein expression, and cyclin D1 mRNA expression were also downregulated [3].in vivo: formononetin also prevented the tumor growth of human breast cancer cells in nude mouse xenografts [3].

[Related Catalog]:

Natural Products >> Flavonoids

Research Areas >> Cancer

[References]

[1]. Liu XJ, et al. Up-regulating of RASD1 and apoptosis of DU-145 human prostate cancer cells induced by formononetin in vitro. Asian Pac J Cancer Prev. 2014;15(6):2835-9.

[2]. Zhang X, et al. Formononetin induces apoptosis in PC-3 prostate cancer cells through enhancing the Bax/Bcl-2 ratios and regulating the p38/Akt pathway. Nutr Cancer. 2014;66(4):656-61.

[3]. Chen J, et al. Formononetin induces cell cycle arrest of human breast cancer cells via IGF1/PI3K/Akt pathways in vitro and in vivo. Horm Metab Res. 2011 Sep;43(10):681-6.

[Related Small Molecules]

Nintedanib (BIBF 1120) | Infigratinib (BGJ398) | AZD4547 | PD173074 | Erdafitinib(JNJ-42756493) | FGF-401 | SU 5402 | Heparan Sulfate | Lucitanib | LY2784544 | BLU554 | Dovitinib (TKI-258, CHIR-258) | Rogaratinib | LY2874455 | BLU-9931

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
479.4±45.0 °C at 760 mmHg

[ Melting Point ]:
256-260 °C

[ Molecular Formula ]:
C₁₆H₁₂O₄

[ Molecular Weight ]:
268.264

[ Flash Point ]:
183.4±22.2 °C

[ Exact Mass ]:
268.073547

[ PSA ]:
59.67000

[ LogP ]:
2.96

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.641

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P337 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S37/39-S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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J. Agric. Food Chem. 63 , 9471-9, (2015)

Little information exists on the effects of ensiling on condensed tannins or proanthocyanidins. The acetone-butanol-HCl assay is suitable for measuring proanthocyanidin contents in a wide range of sam...