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    ?????

    ?????
    ????? ??? ???
    ?? ??:
    446-72-0
    ???:
    ?????
    ???(??):
    ?????
    ???:
    Genistein
    ???(??):
    GEN;G2535;BIO-00;prunetol;GLYCITEN;GeniVida;NPI 031L;enistein;GENISTEIN;Bonistein
    CBNumber:
    CB6163787
    ???:
    C15H10O5
    ??? ??:
    270.24
    MOL ??:
    446-72-0.mol

    ????? ??

    ???
    297-298 °C
    ?? ?
    333.35°C (rough estimate)
    ??
    1.2319 (rough estimate)
    ???
    1.6000 (estimate)
    ?? ??
    -20°C
    ???
    DMSO: soluble
    ?? ?? (pKa)
    6.51±0.20(Predicted)
    ??? ??
    powder
    ??
    off-white
    ???
    insoluble
    Merck
    14,4391
    BRN
    263823
    ???
    Light Sensitive
    InChIKey
    TZBJGXHYKVUXJN-UHFFFAOYSA-N
    CAS ??????
    446-72-0(CAS DataBase Reference)
    EPA
    4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)- (446-72-0)
    ??
    • ?? ? ?? ??
    • ?? ? ???? ?? (GHS)
    ??? ?? Xi,Xn
    ?? ???? ?? 36/38-22
    ????? 26-24/25-22
    WGK ?? 3
    RTECS ?? NR2392000
    TSCA Yes
    ?? ?? IRRITANT
    HS ?? 29329990
    ?? ?? ??? 446-72-0(Hazardous Substances Data)
    ????(GHS):
    ?? ?: Warning
    ??·?? ??:
    ?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
    H302 ??? ??? ?? ?? ?? - ?? ?? 4 ?? P264, P270, P301+P312, P330, P501
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    ????? MSDS


    Genistein

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    Yellow Crystalline Solid

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    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.

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    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

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    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.

    ??

    cytotoxic inhibitor of tyrosine kinase and topoisomerase II kinase

    ??

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

    ?? ??

    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

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    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.

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