| 词条 | Coumestan |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 434749533 | ImageFile = Coumestan.png | ImageSize = | IUPACName = [1]Benzoxolo[3,2-c]chromen-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 | 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 = [1] | 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[2] 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.[3]Coumestrol has about the same 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.[4] 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.[5][6] CoumestansReferences1. ^{{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}} {{Xenoestrogens}}2. ^{{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 }} 3. ^{{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 = http://envirocancer.cornell.edu/FactSheet/Diet/fs1.phyto.cfm#1 | accessdate = 2011-03-19 }} 4. ^{{cite journal | author=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 | id= | pmid=9751507 | doi=10.1210/endo.139.10.6216| last2=Lemmen | last3=Carlsson | last4=Corton | last5=Safe | last6=Van Der Saag | last7=Van Der Burg | last8=Gustafsson }} 5. ^{{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}} 6. ^{{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}} 1 : Coumestans |
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