A naturally-occurring phytoestrogen
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Isomer(s)
33080Sparstolonin B
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Coumestrol

Item No. 11730

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,9-dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one
CAS Number
479-13-0
Synonyms
  • NSC 22842
Molecular Formula
C15H8O5
Formula Weight
268.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mg/ml
λmax
244, 305, 344 nm
SMILES
O=C1OC2=C(C=CC(O)=C2)C3=C1C4=CC=C(O)C=C4O3
InChi Code
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
InChi Key
ZZIALNLLNHEQPJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $49

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    5 mg

    $103

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    10 mg

    $169

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    Product Description

    Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol, Item No. 10006315) binds the estrogen receptors ERα (IC50 = 11 nM) and ERβ (IC50 = 2 nM) and can induce ER-dependent gene expression in isolated cells.1,2 Coumestrol is also a weak antagonist of pregnane X receptor (IC50 = 12 μM) as well as a potential inverse agonist of the constitutive androstane receptor (EC50 = 30 μM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, H.Y., Dykstra, K.D., Birzin, E.T., et al. Estrogen receptor ligands. Part 1: The discovery of flavanoids with subtype selectivity. Bioorg. Med. Chem. Lett. 14(6), 1417-1421 (2004).

    2. Hopert, A.C., Beyer, A., Frank, K., et al. Characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. Environ. Health Perspect. 106(9), 581-586 (1998).

    3. Wang, H., Li, H., Moore, L.B., et al. The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor. Mol. Endocrinol. 22(4), 838-857 (2008).