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27885

Sigma-Aldrich

Coumestrol

≥95.0% (HPLC)

Synonym(s):

7,12-Dihydroxycoumestan

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About This Item

Empirical Formula (Hill Notation):
C15H8O5
CAS Number:
479-13-0
Molecular Weight:
268.22
Beilstein:
266702
EC Number:
207-525-6
MDL number:
MFCD00016885
UNSPSC Code:
41116107
PubChem Substance ID:
57648279
NACRES:
NA.77

Quality Level

100

Assay

≥95.0% (HPLC)

form

powder

impurities

≤10.0% water

mp

≥350 °C (lit.)

SMILES string

Oc1ccc-2c(OC(=O)c3c-2oc4cc(O)ccc34)c1

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

Gene Information

human ... ESR1(2099) , ESR2(2100)
mouse ... Esr1(13982)
rat ... Ar(24208)

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Related Categories

Application


  • Phytoestrogens in Fish Feed Production:Coumestrolis is used as a biomarkers in fish feed production, facilitating the assessment of plant raw materials used in these feeds (Pavlopoulos et al., 2023).

  • Coumestrol and Soybean Leaf Senescence: Coumestrol′s role in soybean leaf senescence is explored, particularly its interactions with phytohormones, suggesting potential agronomic benefits and applications in crop science, it acts as a phytoalexin (Mun et al., 2021).

  • Systemic Defense in Soybeans: Investigating the effects of priming with coumestrol on soybean defense against the root-lesion nematode, this research highlights its potential as a natural plant defense enhancer (Adss et al., 2021).

Biochem/physiol Actions

Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bickoff, E.M., et al.
Journal of the American Chemical Society, 80, 3969-3969 (1958)
Camila Franco et al.
International journal of pharmaceutics, 369(1-2), 5-11 (2008-11-26)
Coumestrol is an estrogenic and antioxidant agent, characterized by its low solubility in aqueous and lipophilic media, once in the aglicone form. In order to improve its solubility in water, coumestrol was associated with beta-cyclodextrin in aqueous media followed by
D F Argenta et al.
Die Pharmazie, 66(12), 929-932 (2012-02-09)
A simple, rapid, and sensitive LC method to determine coumestrol incorporated in the lipid nanoemulsions was validated. The analyses were performed at room temperature on a reversed-phase C18 column using a mobile phase composed of methanol/water with 0.1% trifluoracetic acid
Suzan L Carmichael et al.
Nutrition journal, 10, 105-105 (2011-10-08)
Phytoestrogens may be associated with a variety of different health outcomes, including outcomes related to reproductive health. Recently published data on phytoestrogen content of a wide range of foods provide an opportunity to improve estimation of dietary phytoestrogen intake. Using
Yun-hyeok Choi et al.
Archives of pharmacal research, 33(10), 1651-1654 (2010-11-06)
Bioassay-guided fractionation of the EtOAc-soluble extract of Pueraria lobata based on the inhibition of Aβ-induced toxicity in PC12 cells resulted in the isolation of four known active compounds, genistein (8), biochanin A (9), sissotrin (10), and puerol B (11). Of
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