479-13-0 Usage
Description
Coumestrol is a naturally occurring phytoestrogen found in soybeans, spinach, and clover. It is a member of the coumestan class with hydroxy substituents at positions 3 and 9. Coumestrol competitively binds to estrogen receptors ERα and ERβ, inducing ER-dependent gene expression in isolated cells. It also acts as a weak antagonist of the pregnane X receptor and a potential inverse agonist of the constitutive androstane receptor. Additionally, coumestrol exhibits bright blue fluorescence in neutral or acidic solutions and greenish-yellow fluorescence in strong alkali solutions.
Uses
Used in Pharmaceutical Industry:
Coumestrol is used as a pharmaceutical agent for its estrogenic activity. It can be utilized in the development of treatments for conditions related to estrogen deficiency or as a component in hormone replacement therapies.
Used in Research Applications:
Coumestrol is used as a research tool for studying the effects of estrogen on various biological processes. Its ability to bind to estrogen receptors makes it a valuable compound for investigating the mechanisms of estrogen action and for identifying potential therapeutic targets.
Used in Analytical Chemistry:
Due to its fluorescent properties, coumestrol can be used as a marker or indicator in analytical chemistry. Its distinct fluorescence in different pH environments allows for its use in experiments involving pH measurements or monitoring changes in solution acidity or alkalinity.
Used in Environmental Science:
Coumestrol's fluorescent characteristics can also be applied in environmental science for detecting and monitoring the presence of this compound in natural ecosystems, such as soil and water samples, where it may have an impact on the local flora and fauna.
Synthesis Reference(s)
Tetrahedron Letters, 4, p. 1151, 1963 DOI: 10.1039/jr9630005127
Biochem/physiol Actions
Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.
Safety Profile
An experimental
teratogen. Other experimental reproductive
effects. Mutation data reported. When
heated to decomposition it emits acrid
smoke and irritating fumes.
references
[1]. chen hy, dykstra kd, birzin et, et al. estrogen receptor ligands. part 1: the discovery of flavanoids with subtype selectivity. bioorg med chem lett. 2004 mar 22;14(6):1417-21.[2]. hopert ac, beyer a, frank k, et al. characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. environ health perspect. 1998 sep;106(9):581-6.[3]. wang h, li h, moore lb, et al. the phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane x receptor. mol endocrinol. 2008 apr;22(4):838-57.
Check Digit Verification of cas no
The CAS Registry Mumber 479-13-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 9 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 479-13:
(5*4)+(4*7)+(3*9)+(2*1)+(1*3)=80
80 % 10 = 0
So 479-13-0 is a valid CAS Registry Number.
InChI:InChI=1/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
479-13-0Relevant articles and documents
Synthesis of coumestrol and aureol
Sheng, Jianfei,Xu, Tianlong,Zhang, Ensheng,Zhang, Xuejing,Wei, Wentao,Zou, Yong
, p. 2749 - 2753 (2016)
A total synthesis of coumestrol (1) and aureol (2) is described. The Perkin condensation of 2-bromo-4-hydroxylphenylacetic acid (6) and o-hydroxybenzaldehydes (7) gave the corresponding 2′-bromo-3-arylcoumarins (9). A copper-catalyzed consecutive hydroxylation and aerobic oxidative coupling of 9 under microwave conditions facilitated the total synthesis of 1 and 2, respectively, with spectroscopic data highly similar to those of natural products.
Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins
Song, Xianheng,Luo, Xiang,Sheng, Jianfei,Li, Jianheng,Zhu, Zefeng,Du, Zhibo,Miao, Hui,Yan, Meng,Li, Mingkang,Zou, Yong
, p. 17391 - 17398 (2019/06/24)
A copper-catalyzed intramolecular cross dehydrogenative C-O coupling reaction of 2′-hydroxyl-3-arylcoumarins was developed. This protocol provided a facile and efficient strategy for the construction of natural coumestans and derivatives in moderate to high yields. This transformation exhibited good functional group compatibility and was amenable to substrates with free phenolic hydroxyl groups.
Synthetic method of polyhydroxy substituted coumestrol natural product
-
, (2017/08/28)
The invention discloses a synthetic method of a polyhydroxy substituted coumestrol natural product. 2-bromine-4-hydroxyphenylacetic acid serves as a raw material to make a condensation reaction with a hydroxy substituted salicylaldehyde compound, and a hydroxy substituted 3-(2-bromine-4-hydroxycyclohexyl phenyl)-7-hydroxy coumarin compound is obtained; and then a hydroxylation/oxidative coupling reaction is made under the condition of a catalyst and microwave heating, and the polyhydroxy substituted coumestrol natural product is obtained. The synthetic method is simple in route, easy and convenient to operate, high in yield, soft in reaction condition, free of needs of precious metal catalyzing, high in atom economy and low in cost, and multiple steps of cascade reactions are made simultaneously.
