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    Genistein

    description Pharmacological effects Physical and Chemical Properties Uses Mechanism of action Health Benefits
    Genistein
    Genistein structure
    CAS No.
    446-72-0
    Chemical Name:
    Genistein
    Synonyms
    GEN;G2535;BIO-00;prunetol;GLYCITEN;GeniVida;NPI 031L;enistein;GENISTEIN;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
    pka
    6.51±0.20(Predicted)
    form 
    powder
    color 
    off-white
    Water Solubility 
    insoluble
    Merck 
    14,4391
    BRN 
    263823
    Stability:
    Light Sensitive
    InChIKey
    TZBJGXHYKVUXJN-UHFFFAOYSA-N
    CAS DataBase Reference
    446-72-0(CAS DataBase Reference)
    EWG's Food Scores
    1
    FDA UNII
    DH2M523P0H
    NCI Dictionary of Cancer Terms
    genistein
    NCI Drug Dictionary
    genistein
    EPA Substance Registry System
    4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)- (446-72-0)
    SAFETY
    • Risk and Safety Statements
    Symbol(GHS) 
    GHS07
    Signal word  Warning
    Hazard statements  H302
    Precautionary statements  P301+P312+P330
    Hazard Codes  Xi,Xn
    Risk Statements  36/38-22
    Safety Statements  26-24/25-22
    WGK Germany  3
    RTECS  NR2392000
    TSCA  Yes
    HazardClass  IRRITANT
    HS Code  29329990

    Genistein price More Price(70)

    Manufacturer Product number Product description CAS number Packaging Price Updated Buy
    Sigma-Aldrich 345834 Genistein, Soybean - CAS 446-72-0 - Calbiochem A cell-permeable, reversible, substrate competitive inhibitor of protein tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC?? = 2.6 μM). 446-72-0 50 mg $205.35 2021-12-16 Buy
    Sigma-Aldrich 1288816 Genistein United States Pharmacopeia (USP) Reference Standard 446-72-0 15mg $325 2021-12-16 Buy
    Sigma-Aldrich 05360590 Genistein primary reference standard 446-72-0 50mg $359 2021-12-16 Buy
    TCI Chemical G0272 Genistein >98.0%(HPLC) 446-72-0 100mg $72 2021-12-16 Buy
    TCI Chemical G0272 Genistein >98.0%(HPLC) 446-72-0 1g $258 2021-12-16 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

    genistein is an isoflavone commonly found in soy. It has demonstrated uV-protection properties through anti-oxidant activity. Studies indicate genistein can promote collagen synthesis, making it applicable in anti-aging cosmetics.

    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.

    General Description

    Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

    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™ .

    Biochem/physiol Actions

    Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.

    Anticancer Research

    It is an isoflavone and is obtained from a variety of plants like psoralea (Psoraleacorylifolia), kudzu (Pueraria lobata), faba beans (Vicia faba), and soybeans(Glycine max). It exhibits anticancer effect by inhibiting NF-κB and protein kinaseB (Akt) signaling pathways (Singh et al. 2016b). It blocks the proliferation of cancercells via the inhibition of cell growth enzymes and survival like tyrosine kinase andtopoisomerase II; hence it is used to treat leukemia. Genistein increases the growthrate of some estrogen receptors in breast cancer cells and the rate of proliferation of estrogen-dependent breast cancer by competitive binding to the estrogen-β receptors.It may be involved in JNK pathway in inducing activator protein-1(AP-1) activity(Wang et al. 2012; Dixon and Ferreira 2002).

    Safety Profile

    Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

    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( 606)Suppliers
    Supplier Tel Fax Email Country ProdList Advantage
    Aktin Chemicals, Inc.
    028-85159085
    86-28-85159085 Ex:604 info@aktinchem.com CHINA 1026 58
    Capot Chemical Co.,Ltd.
    +86(0)13336195806 +86-571-85586718
    +86-571-85864795 sales@capotchem.com China 20012 60
    Henan DaKen Chemical CO.,LTD.
    +86-371-66670886
    info@dakenchem.com China 15426 58
    Henan Tianfu Chemical Co.,Ltd.
    0371-55170693
    0371-55170693 info@tianfuchem.com China 22607 55
    Hangzhou FandaChem Co.,Ltd.
    008615858145714
    +86-571-56059825 fandachem@gmail.com CHINA 9143 55
    Nanjing ChemLin Chemical Industry Co., Ltd.
    025-83697070
    product@chemlin.com.cn CHINA 3013 60
    Nanjing Finetech Chemical Co., Ltd.
    025-85710122 17714198479
    025-85710122 sales@fine-chemtech.com CHINA 890 55
    Shanxi Naipu Import and Export Co.,Ltd
    +8613734021967
    kaia@neputrading.com CHINA 1011 58
    Shanghai Zheyan Biotech Co., Ltd.
    18017610038
    zheyansh@163.com CHINA 3623 58
    career henan chemical co
    +86-0371-55982848
    sales@coreychem.com China 29953 58

    View Lastest Price from Genistein manufacturers

    Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
    2022-01-24 Genlstein
    446-72-0
    US $1.00 / g 10g 98% HPLC 1000kg Guangzhou Biocar Biotechnology Co.,Ltd.
    2022-01-24 Genistein
    446-72-0
    US $20.00-100.00 / KG 0.5KG >99% 20tons Anhui Rencheng Technology Co., Ltd
    2022-01-20 Genistein
    446-72-0
    US $10.00 / KG 1KG 99% 500tons/month Shanxi Naipu Import and Export Co.,Ltd

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