Coumestan

Coumestan
Names
	IUPAC name Pterocarp-6a(11a)-en-6-one
	Systematic IUPAC name 6H-[1]Benzofuro[3,2-c][1]benzopyran-6-one
Identifiers
CAS Number	479-12-9;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:72578;
ChemSpider	553855;
PubChemCID	638309;
UNII	MT103Z562V;
CompTox Dashboard(EPA)	DTXSID30197316;
	InChI InChI=1S/C15H8O3/c16-15-13-9-5-1-3-7-11(9)17-14(13)10-6-2-4-8-12(10)18-15/h1-8H Key: JBIZUYWOIKFETJ-UHFFFAOYSA-N; InChI=1/C15H8O3/c16-15-13-9-5-1-3-7-11(9)17-14(13)10-6-2-4-8-12(10)18-15/h1-8H Key: JBIZUYWOIKFETJ-UHFFFAOYAF;
	SMILES C1=CC=C2C(=C1)C3=C(O2)C4=CC=CC=C4OC3=O; O=C3Oc4ccccc4c2oc1c(cccc1)c23;
Properties
Chemical formula	C15H8O3
Molar mass	236.22 g/mol
Melting point	187 to 188 °C (369 to 370 °F; 460 to 461 K)
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

Coumestanis aheterocyclic organic compound.Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products ofpterocarpan^[2]that are similar tocoumarin.Coumestans, includingcoumestrol,aphytoestrogen,are found in a variety of plants. Food sources high in coumestans includesplit peas,pinto beans,lima beans,and especiallyalfalfaandclover sprouts.^[3]

Coumestrolhas about the same binding affinity for theER-β estrogen receptoras17β-estradiol,but much less affinity than17α-estradiol,although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.^[4]

Because of the estrogenic activity of some coumestans, a variety ofsyntheseshave been developed that allow the preparation of coumestans so that their pharmacological effects can be explored.^[5]^[6]

Coumestans

References

^Singh, Rishi Pal; Singh, Daljeet (1985)."An elegant synthesis of 6H-benzofuro[3,2-c][1]benzopyran-6-ones".Heterocycles.23(4): 903.doi:10.3987/R-1985-04-0903.
^V. A. Tuskaev (April 2013). "Synthesis and biological activity of coumestan derivatives (Review)".Pharmaceutical Chemistry Journal.47(1): 1–11.doi:10.1007/s11094-013-0886-5.S2CID 32550281.
^Barbour S. Warren; Carol Devine (July 2001)."Phytoestrogens and Breast Cancer".Program on Breast Cancer and Environmental Risk Factors.Cornell University.Retrieved2011-03-19.
^Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998)."Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta".Endocrinology.139(10): 4252–4263.doi:10.1210/endo.139.10.6216.PMID 9751507.
^Yao, Tuanli; Yue, Dawei; Larock, Richard C (2005). "An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization".Journal of Organic Chemistry.70(24): 9985–9989.doi:10.1021/jo0517038.PMID 16292831.
^Takeda, Norihiko; Miyata, Okiko; Naito, Takeaki (2007). "Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans".European Journal of Organic Chemistry.2007(9): 1491–1509.doi:10.1002/ejoc.200601001.

[1] Singh, Rishi Pal; Singh, Daljeet (1985)."An elegant synthesis of 6H-benzofuro[3,2-c][1]benzopyran-6-ones".Heterocycles.23(4): 903.doi:10.3987/R-1985-04-0903.

[2] V. A. Tuskaev (April 2013). "Synthesis and biological activity of coumestan derivatives (Review)".Pharmaceutical Chemistry Journal.47(1): 1–11.doi:10.1007/s11094-013-0886-5.S2CID 32550281.

[3] Barbour S. Warren; Carol Devine (July 2001)."Phytoestrogens and Breast Cancer".Program on Breast Cancer and Environmental Risk Factors.Cornell University.Retrieved2011-03-19.

[4] Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998)."Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta".Endocrinology.139(10): 4252–4263.doi:10.1210/endo.139.10.6216.PMID 9751507.

[5] Yao, Tuanli; Yue, Dawei; Larock, Richard C (2005). "An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization".Journal of Organic Chemistry.70(24): 9985–9989.doi:10.1021/jo0517038.PMID 16292831.

[6] Takeda, Norihiko; Miyata, Okiko; Naito, Takeaki (2007). "Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans".European Journal of Organic Chemistry.2007(9): 1491–1509.doi:10.1002/ejoc.200601001.

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