An isoflavonoid phytoestrogen
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Genistein

Item No. 10005167

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
446-72-0
Synonyms
  • CI-75610
  • NSC 36586
Molecular Formula
C15H10O5
Formula Weight
270.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2)(1:6): 1 mg/ml
λmax
261 nm
SMILES
Oc1ccc(cc1)c1coc2cc(O)cc(O)c2c1=O
InChi Code
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
InChi Key
TZBJGXHYKVUXJN-UHFFFAOYSA-N
Origin
Plant/Styphnolobium japonicum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $39

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    250 mg

    $87

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    500 mg

    $136

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    1 g

    $231

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Genistein is an isoflavonoid phytoestrogen that has been found in soybeans (G. max/S. hispida) and has kinase inhibitory, anticancer, pro-cancer, hepatoprotective, and antiviral properties.1 It inhibits the tyrosine kinases EGFR, pp50v-Src, and pp110gag-fes (IC50s = 6, 7-8, and 6.5 µg/ml, respectively) and decreases EGF-induced serine, threonine, and tyrosine phosphorylation of EGFR in A431 cells when used at a concentration of 20 µg/ml.2 Genistein inhibits proliferation and induces apoptosis in a variety of cancer cells, including Bel 7402 hepatocellular carcinoma cells when used at a concentration of 10 µg/ml.1,3 It reduces tumor invasion and angiogenesis in a Bel 7402 mouse subrenal capsule xenograft model when administered at a dose of 50 mg/kg per day.3 However, when administered at the same dose on postnatal days 1-5, genistein increases the incidence of uterine adenocarcinoma in a mouse model of cancer induced by the estrogen receptor agonist diethylstilbestrol (DES; Item No. 10006876).4 It reduces lipid accumulation and inflammation in the liver of ovariectomized (OVX) and non-OVX female rats in a model of high-fat high-fructose diet-induced nonalcoholic hepatosteatosis (NASH) when administered at a dose of 16 mg/kg per day.5 Genistein (10 µM) also inhibits HIV-1 DNA synthesis in resting CD4+ T cells.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Spagnuolo, C., Russo, G.L., Orhan, I.E., et al. Genistein and cancer: Current status, challenges, and future directions. Adv. Nutr. 6(4), 408-419 (2015).

    2. Akiyama, T., Ishida, J., Nakagawa, S., et al. Genistein, a specific inhibitor of tyrosine-specific protein kinases. The Journal of Biological Chemisty 262(1), 5592-5595 (1987).

    3. Gu, Y., Zhu, C.-F., Iwamoto, H., et al. Genistein inhibits invasive potential of human hepatocellular carcinoma by altering cell cycle, apoptosis, and angiogenesis. World J. Gastroenterol. 11(41), 6512-6517 (2005).

    4. Newbold, R.R., Banks, E.P., Bullock, B., et al. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res. 61(11), 4325-4328 (2001).

    5. Pummoung, S., Werawatganon, D., Klaikeaw, N., et al. Genistein-attenuated hepatic steatosis and inflammation in nonalcoholic steatohepatitis with bilateral ovariectomized rats. Pharmacogn. Mag. 14(55), 20-24 (2018).

    6. Guo, J., Xu, X., Rasheed, T.K., et al. Genistein interferes with SDF-1- and HIV-mediated actin dynamics and inhibits HIV infection of resting CD4 T cells. Retrovirology 10, 62 (2013).