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Merck

27885

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
UNSPSC Code:
41116107
NACRES:
NA.77
PubChem Substance ID:
57648279
EC Number:
207-525-6
Beilstein/REAXYS Number:
266702
MDL number:
MFCD00016885
Assay:
≥95.0% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

Coumestrol, ≥95.0% (HPLC)

InChI key

ZZIALNLLNHEQPJ-UHFFFAOYSA-N

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

SMILES string

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

assay

≥95.0% (HPLC)

form

powder

impurities

≤10.0% water

mp

≥350 °C (lit.)

Quality Level

100

Gene Information

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

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK5963
BCCJ3922
BCCC5005
BCCB2857
BCCB2018

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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
Larry M Mallis et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 796(1), 71-86 (2003-10-14)
In recent years, consumption of herbal supplements as an alternative to pharmaceutical drug therapy has increased. For example, with the health claims labeling which describes the link between soy-protein and a reduced risk of coronary heart disease (CHD), the consumption
J Młynarczuk et al.
Environmental toxicology, 28(7), 411-418 (2011-06-10)
Coumestrol is one of a few biologically active substances present in leguminous plants, which are widely used as fodder for ruminants. Depending on the doses, coumestrol acts on the reproductive processes as an estrogen-like factor or antiestrogen to evoke a
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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