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Genistein

description Pharmacological effects Physical and Chemical Properties Uses Mechanism of action Health Benefits
Genistein
Genistein
CAS No.
446-72-0
Chemical Name:
Genistein
Synonyms
GEN;prunetol;GLYCITEN;GeniVida;NPI 031L;c.i.75610;genisteol;GENISTEIN;GENESTEIN;Bonistein
CBNumber:
CB6163787
Molecular Formula:
C15H10O5
Formula Weight:
270.24
MOL File:
446-72-0.mol

Genistein Properties

Melting point:
297-298 °C
Boiling point:
333.35°C (rough estimate)
Density 
1.2319 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
−20°C
solubility 
DMSO: soluble
form 
powder
color 
off-white
Water Solubility 
insoluble
Merck 
14,4391
BRN 
263823
Stability:
Light Sensitive
CAS DataBase Reference
446-72-0(CAS DataBase Reference)
EPA Substance Registry System
4H-1-Benzopyran- 4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)- (446-72-0)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xi,Xn
Risk Statements  36/38-22
Safety Statements  26-24/25-22
WGK Germany  3
RTECS  NR2392000
TSCA  Yes
HazardClass  IRRITANT
Hazardous Substances Data 446-72-0(Hazardous Substances Data)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
Precautionary statements:

Genistein price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1288816 Genistein United States Pharmacopeia (USP) Reference Standard 446-72-0 15mg $303 2017-11-08 Buy
Sigma-Aldrich 05360590 Genistein primary pharmaceutical reference standard 446-72-0 50mg $309.5 2017-11-08 Buy
TCI Chemical G0272 Genistein >98.0%(HPLC) 446-72-0 100mg $59 2017-12-01 Buy
TCI Chemical G0272 Genistein >98.0%(HPLC) 446-72-0 1g $212 2017-12-01 Buy
Alfa Aesar J63241 4',5,7-Trihydroxyisoflavone, 99+% 446-72-0 10g $604 2017-11-08 Buy

Genistein Chemical Properties,Uses,Production

description

Genistein is one of the most abundant isoflavones in soy and is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Because of its similar structure to that of human estrogen it is also called a phytoestrogen. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses.
Genistein is a soy-derived isoflavone and phytoestrogen with antineoplastic activity. Genistein binds to and inhibits protein-tyrosine kinase, thereby disrupting signal transduction and inducing cell differentiation. This agent also inhibits topoisomerase-II, leading to DNA fragmentation and apoptosis, and induces G2/M cell cycle arrest. Genistein exhibits antioxidant, antiangiogenic, and immunosuppressive activities. In adult animals, dietary genistein has chemopreventive effects on breast, prostate, and other endocrine-dependent tumors.

Pharmacological effects

Genistein is a kind of polyphenols compound which can be found in soy and red clover and other plants with its molecular structure being similar to 17β-estradiol and having antioxidant activity and high affinity towards estrogen receptor. It can inhibit the activity of protein tyrosine kinase (PTK) and topoisomerase enzyme activity II with capability of inducing programmed cell death and improve the efficacy of anti-cancer drug as well as inhibit angiogenesis, and so on. It is one type of flavonoids (also called isoflavones) and is often found together with isoflavones called the isoflavones. They are all called soy isoflavones. Those benefits of these kinds of compounds on human health have been studied extensively and it is a promising cancer chemopreventive agent with significant impact on preventing cancer and other diseases. Genistein is the major phytoestrogens in the present study.
Plant Source: legume Genista (broom).
Clinical Applications: it can be used for female beauty care and prevention of blood diseases and cancer.
Genistein contains polyphenol structure with the hydrogen atoms in the phenolic hydroxyl group being prone to dissociate from external oxygen atom from the external interaction, leading to the formation of hydrogen ions to play reduction effect. This is the structure basis for the capability of the genistein of anti-oxidative and reductive. So those substances in food can fight against superoxide anion radicals, blocking the chain reaction of free radicals and play a role in anti-oxidation.
Genistein is not a hormone, but because it can bind to estrogen receptors and plays a weak estrogenic effect, it is called phytoestrogens. Because the activity of isoflavones is only 1/1000 of the estradiol which can competitively bind with estrogen receptors, exhibiting two-way adjustment with the resulting estrogenic effects of much lower harmful effects than estradiol and further with protective effect on then hormone related diseases such as menopause, osteoporosis, elevated blood lipids, etc; for patients of high levels of estrogen, it exhibits anti-estrogenic activity and can prevent breast cancer, endometriosis with two-way balance adjustment function.
Genistein, for the rat high cholesterol induced by TNT (trinitrotoluene) WR1339, has effect of lowering serum cholesterol and triglycerides with the effect on the later one being particularly significant.
This information is edited by Xiongfeng Dai from Chemicalbook.

Physical and Chemical Properties

It appears as pale yellow dendritic needle-like powder with the melting point being 297 ℃-298 ℃; It is soluble in common organic solvents but almost insoluble in water. When being dissolved in dilute alkali, it will become yellow color.

Uses

It has anti-tumor, anti-fungal, blood lipid-lowering and can fight against estrogen activity.

Mechanism of action

Genistein may inhibit cancer cell growth by blocking enzymes required for cell growth. Genistein may decrease cardiovascular risk in postmenopausal women by interacting with the nuclear estrogen receptors to alter the transcription of cell specific genes. In randomized clinical trials, genistein was seen to increase the ratio of nitric oxide to endothelin and improved flow-mediated endothelium dependent vasodilation in healthy postmenopausal women. In addition, genistein may have beneficial effects on glucose metabolism by inhibiting islet tyrosine kinase activity as well as insulin release dependent on glucose and sulfonylurea.
References
https://www.drugbank.ca/drugs/DB01645

Health Benefits

Estrogenic effect
The estrogenic activity of genistein has been confirmed in many studies. Of all the isoflavones, genistein has the strongest estrogenic activity. The estrogenic effect of genistein may explain its protective action against osteoporosis and its possible effect on body weight reductions. Genistein is also used to ease menopause symptoms, such as hot flushes.
Antioxidant
Genistein is a strong antioxidant. Genistein removes damaging free radicals and reduces lipid peroxidation. Genistein increases the activity of other antioxidant enzymes such as glutathione peroxidase, superoxide dismutase and glutathione reductase. Studies have shown that genistein can also influence the growth of cells which are not hormone-dependent.
Anticancer
Genistein seems to reduce the risk for some hormone related cancers, principally breast cancer and prostate cancer. Epidemiological studies show that consumption of isoflavones may protect against breast and prostate cancer. High dietary intake of soy products China and Japan are linked with low incidence of these cancers. There are lots of theories to explain the anti-cancer action of genistein: inhibition of angiogenesis, inhibition of tyrosine kinases, antioxidant property, and anti-estrogen action (it is known that estrogen increases risk for certain cancers). Genistein binds with estrogen receptors, preventing the estrogen from binding and initiating cancer growth.

Heart health

Many in-vitro tests have demonstrated that genistein inhibits cellular cholesterol synthesis and cholesterol esterification. Genistein also reduces fatty acid oxidation and exerts lipid lowering effect. Only oxidized LDL cholesterol is absorbed by the arterial cells and prevention of this oxidation will reduce the risk for arteriosclerosis. Gensistein prevents the formation of hearth attacks and strokes by acting as anticlotting agent.
References
http://www.phytochemicals.info/phytochemicals/genistein.php

Chemical Properties

Yellow Crystalline Solid

Uses

Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol

Uses

Genistein, a phytoestrogen found in soy products, is a highly specific inhibitor of protein tyrosine kinase (PTK) which blocks the mitogenic effect mediated by EGF on NIH-3T3 cells with IC50 of 12μM or by insulin with IC50 of 19 μM.

Uses

cytotoxic inhibitor of tyrosine kinase and topoisomerase II kinase

Definition

ChEBI: 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.

Biological Activity

Phytoestrogen with a wide range of biological actions. Inhibits protein tyrosine kinases including epidermal growth factor receptor kinase. Also binds to PPAR γ and estrogen receptors and acts as an agonist at GPR30. Also available as part of the MAPK Cascade Inhibitor Tocriset™ .

Purification Methods

Crystallise it from EtOH or aqueous EtOH. It has UV: max at 290nm (EtOH). The S(-)-enantiomer (natural form) has m 255-256o (from EtOH) and [] D 20 -28.0o (c 2, EtOH), [ ] D 20 -35.2o (c 1, pyridine).[Beilstein 18 H 503, 18 II 164, 18 III/IV 2630.] Genistein (4',5,7-trihydroxyisoflavone) [446-72-0]M 270.2 crystallises from 60% aqueous EtOH or water with m 297-298o and [] D 20 -28o (c 0.6, 20mM NaOH). [Beilstein 18/4 V 594.]For Naringin (naringenin 7-rhamnoglucoside) See “Carbohydrates” in Chapter 6.

Genistein Preparation Products And Raw materials

Raw materials

Preparation Products


Genistein Suppliers

Global( 394)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19954 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3218 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
inquiry@dakenchem.com CHINA 22144 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20803 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32765 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070;product@chemlin.com.cn
product@chemlin.com.cn CHINA 3015 60
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales1@fine-chemtech.com CHINA 893 55
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 300 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3625 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 10012 58

View Lastest Price from Genistein manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-10 Genistein
446-72-0
US $2.00 / KG 1KG 98% 10000kg

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