Coumestrol

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Coumestrol
Systematic (IUPAC) name
3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
Identifiers
CAS number	479-13-0
ATC code	?
PubChem	5281707
Chemical data
Formula	C15H8O5
Mol. mass	268.22
SMILES	eMolecules & PubChem
Synonyms	Chrysanthin
Physical data
Melt. point	385(EXP) °C
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica.

Coumestrol was first identified by E. M. Bickoff in alfalfa in 1957.<ref>E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, and F. Deeds (1957). "Coumestrol, a New Estrogen Isolated from Forage Crops". Science 126: 969–970. doi:10.1126/science.126.3280.969-a. </ref> It has since be found in a variety of legumes, soybeans, brussels sprouts, and spinach. Clover and soybeans have the highest concentrations.<ref name="Amin">Amr Amin and Michael Buratovich (2007). ""The Anti-Cancer Charm of Flavonoids: A Cup-of-Tea Will Do!". Recent Patents on Anti-Cancer Drug Discovery 2 (2): 109–117. doi:10.2174/157489207780832414. </ref>

Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. The chemical shape of coumestrol orients its two hydroxy groups in the same position as the two hydroxy groups in estradiol, allowing it to inhibit the activity of aromatase and hydroxysteroid dehydrogenase.<ref>Blomquist CH, Lima PH, Hotchkiss JR (2005). "Inhibition of 3a-hydroxysteoid dehydogenase (3a-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids". Steroids 70 (8): 507–514. doi:10.1016/j.steroids.2005.01.004. </ref> These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.<ref name="Amin"/>

Pueraria mirifica or White Kawo Krua has been found to contain concentration of Coumestrol where Cu²⁺ at 1000 ppm the highest concentration was to be found where CuCl₂, MnCl₂ and FeCl₂ at 1,000 ppm can in fact stimulate coumestrol accumulation.

General Properties

*Molecular Weight

268.22

*Molecular Formula

C₁₅H₈O₅

*IUPAC NAME

3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one

*Canonical Smiles

C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O

*Isomeric Smiles

PhysioChemical Properties

*Melting Point

385(EXP)

*LogP

1.57(EST)

*Water Solubility

External Links

• [1]Pubchem
• [2]]KEGG Compound
• [3]Human Metabolome DataBase

Categories:Hormones