An isoflavone
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Daidzein

Item No. 10005166

Technical Information
Formal Name
7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
486-66-8
Molecular Formula
C15H10O4
Formula Weight
Purity
≥95%
Formulation
A crystalline solid
DMF: 10 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.15 mg/mlEthanol: 0.1 mg/ml
λmax
249, 301 nm
SMILES
Oc1ccc(cc1)c1coc2cc(O)ccc2c1=O
InChi Code
InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
InChi Key
ZQSIJRDFPHDXIC-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Daidzein is an isoflavone phytoestrogenic compound that has been found in soybeans and other legumes.1 It binds to estrogen receptor β (ERβ; Ki = 2.8 µM) but not ERα at concentrations up to 1 mM.2 It is estrogenic in vitro, increasing gene transcription mediated by the estrogen response element (ERE) in a reporter assay in an ERβ-dependent manner (EC50 = 2.8 µM for MCF-7 cells expressing ERβ).1 Daidzein is an inhibitor of carbonic anhydrase (CA) that is selective for carbonic CAVII and CAXII (Kis = 4.2 and 56 nM, respectively) over CAI, II, and IV (Kis = >10,000, >10,000, and 718.7 nM, respectively).3 It reduces tumor growth in a PC3 prostate cancer mouse orthotopic model when administered at a dose of 50 mg/kg per day and potentiates the effects of radiation therapy.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Harris, D.M., Besselink, E., Henning, S.M., et alPhytoestrogens induce differential estrogen receptor alpha- or beta-mediated responses in transfected breast cancer cells. Exp. Biol. Med. (Maywood) 230(8), 558-568 (2005).

    2. Zhao, L., and Brinton, R.D. Structure-based virtual screening for plant-based ERβ-selective ligands as potential preventative therapy against age-related neurodegenerative diseases. J. Med. Chem. 48(10), 3463-3466 (2005).

    3. Karioti, A., Ceruso, M., Carta, F., et alNew natural product carbonic anhydrase inhibitors incorporating phenol moieties. Bioorg. Med. Chem. 23(22), 7219-7225 (2015).

    4. Singh-Gupta, V., Zhang, H., Yunker, C.K., et alDaidzein effect on hormone refractory prostate cancer in vitro and in vivo compared to genistein and soy extract: Potentiation of radiotherapy. Pharm. Res. 27(6), 1115-1127 (2010).