Dihydrodaidzein Chemical Properties

Melting point:

250-251°C

Boiling point:

529.5±50.0 °C(Predicted)

Density 

1.386±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer, Under Inert Atmosphere

solubility 

≤0.1mg/ml in ethanol;30mg/ml in DMSO;10mg/ml in dimethyl formamide

pka

7.71±0.40(Predicted)

form 

powder to crystal

color 

Light orange to Yellow to Green

λmax

313nm(EtOH aq.)(lit.)

CAS DataBase Reference

17238-05-0

Safety Information

HS Code 

2932990090

Dihydrodaidzein Usage And Synthesis

Chemical Properties

Light Beige Needles

Uses

A metabolite of Daidzein.

Uses

Daidzein is an isoflavonoid phytoestrogenic compound found in soybeans, pea pods, clover, kudzu, and other legumes. Dihydrodaidzein is an active, estrogenic metabolite of daidzein. It has vasodilatory action on rat isolated aortic rings at 1 μg/ml. It stimulates the estrogen receptor-dependent growth of breast cancer MCF-7 cells at micromolar concentrations. Dihydrodaidzein is produced by the metabolism of daidzein in colonic bacteria and may be further metabolized to various bioactive compounds, including equol .

Definition

ChEBI: A hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4' and 7.

Biological Activity

dihydrodaidzein, an active, estrogenic metabolite of daidzein in colonic bacteria, probably is further metabolized to various bioactive compounds including equol. as an estrogen receptor agonist, dihydrodaidzein, at micromolar concentrations, activates the estrogen receptor-dependent growth of breast cancer cells. daidzein, an isoflavonoid phytoestrogenic compound, is found in soybeans, clover, kudzu, and other legumes.

in vitro

prostatic fluid and plasma concentrations of dihydrodaidzein were sufficient to block the growth of benign human prostatic epithelial cells (prec). dihydrodaidzein showed a significant inhibitory effect on the growth of prostate cancer cell line lncap. additionally, dihydrodaidzein slightly triggered the apoptosis of prec. in addition to affecting apoptosis, dihydrodaidzein decreased proliferation, which was associated with the changes in cell cycle distribution and caspase 3 activation [1].

in vivo

male c57b1/6 wild type mice were administered orally with dihydrodaidzein at a dose of 25 mg/kg/day for 4 weeks. compared to the control groups, the neointima of mice treated with dihydrodaidzein was thickened. in dihydrodaidzein-treated mice, the intimal thickness in the non-injured right iliac artery was not altered. moreover, neointimal proliferation was selectively blocked by dihydrodaidzein via suppressing the migration and proliferation of vascular smooth muscle cell and dampening the endothelial apoptosis [2].

References

[1]. hedlund, t., bokhoven, a., johannes, w., nordeen, s., & ogden, l. prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. the prostate. 2006; 66(5): 557-566.
[2]. shen, j., white, m., husband, a., hambly, b., & bao, s. phytoestrogen derivatives differentially inhibit arterial neointimal proliferation in a mouse model. european journal of pharmacology. 2006; 548(1-3): 123-128.

Dihydrodaidzein(17238-05-0)Related Product Information

• morelloflavone
• Rotenone
• AMORPHIGENIN
• amorphin
• 4',7-DIMETHOXYISOFLAVANONE
• Dihydrodaidzein
• (-)-TEPHROSIN
• 11-HYDROXYROTENONE
• MILLETTONE
• DIHYDROPRUNETIN
• DIHYDROFORMONONETIN
• AKOS NCG1-0077
• 6-HYDROXYSUMATROL
• DIHYDROGENISTEIN
• DIHYDROBIOCHANIN A
• 12ALPHA-HYDROXYROTENONE
• DALBERGIOIDINE
• DIHYDROISOFORMONONETIN