{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 434749533 | ImageFile = Coumestan.png | ImageSize = | IUPACName = Pterocarp-6a(11a)-en-6-one | SystematicName = 6''H''-[1]Benzofuro[3,2-''c''][1]benzopyran-6-one | OtherNames = |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 553855 | 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 | InChIKey = JBIZUYWOIKFETJ-UHFFFAOYAF | SMILES1 = O=C3Oc4ccccc4c2oc1c(cccc1)c23 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JBIZUYWOIKFETJ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 479-12-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = MT103Z562V | PubChem = 638309 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 72578 | SMILES = C1=CC=C2C(=C1)C3=C(O2)C4=CC=CC=C4OC3=O }} |Section2={{Chembox Properties | C=15 | H=8 | O=3 | MolarMass = 236.22 g/mol | Appearance = | Density = | MeltingPtC = 187 to 188 | MeltingPt_ref = <ref>{{cite journal|title=An elegant synthesis of 6H-benzofuro[3,2-c][1]benzopyran-6-ones|author1=Singh, Rishi Pal |author2=Singh, Daljeet |journal=Heterocycles|year=1985|volume=23|issue=4|pages=903|doi=10.3987/R-1985-04-0903|doi-access=free}}</ref> | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Coumestan''' is a heterocyclic organic compound. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of pterocarpan<ref>{{cite journal | journal = Pharmaceutical Chemistry Journal | date = April 2013 | volume =47 | issue = 1 | pages = 1–11 | title = Synthesis and biological activity of coumestan derivatives (Review) | author = V. A. Tuskaev | doi = 10.1007/s11094-013-0886-5 | s2cid = 32550281 }}</ref> that are similar to coumarin. Coumestans, including coumestrol, a phytoestrogen, are found in a variety of plants. Food sources high in coumestans include split peas, pinto beans, lima beans, and especially alfalfa and clover sprouts.<ref>{{cite web |author1=Barbour S. Warren |author2=Carol Devine | title = Phytoestrogens and Breast Cancer | work = Program on Breast Cancer and Environmental Risk Factors | publisher = Cornell University | date = July 2001 | url = https://envirocancer.cornell.edu/FactSheet/Diet/fs1.phyto.cfm#1 | access-date = 2011-03-19 }}</ref>
Coumestrol has a similar binding affinity for the ER-β estrogen receptor as 17β-estradiol, but much less affinity than 17α-estradiol, although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.<ref>{{cite journal |vauthors=Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA| title=Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta | journal=Endocrinology | volume=139 | issue=10 | year=1998 | pages=4252–4263 | url = http://endo.endojournals.org/cgi/content/full/139/10/4252 | pmid=9751507 | doi=10.1210/endo.139.10.6216| doi-access= | url-access=subscription }}</ref>
Because of the estrogenic activity of some coumestans, a variety of syntheses have been developed that allow the preparation of coumestans so that their pharmacological effects can be explored.<ref>{{cite journal|author1=Yao, Tuanli |author2=Yue, Dawei |author3=Larock, Richard C |title=An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization|journal=Journal of Organic Chemistry|year=2005|volume=70|issue=24|pages=9985–9989|doi=10.1021/jo0517038|pmid=16292831}}</ref><ref>{{cite journal|author1=Takeda, Norihiko |author2=Miyata, Okiko |author3=Naito, Takeaki |title=Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: short synthesis of natural 2-arylbenzofurans|journal=European Journal of Organic Chemistry|year=2007|issue=9|pages=1491–1509|doi=10.1002/ejoc.200601001|volume=2007}}</ref>
==Coumestans== <gallery> Image:coumestrol.png|Coumestrol Image:wedelolactone.png|Wedelolactone Image:plicadin.png|Plicadin </gallery>
==References== {{Reflist}}
{{Xenoestrogens}}
Category:Coumestans