Coumestan

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Coumestan
Coumestan.png
Identifiers
CAS number 479-12-9 YesY
PubChem 638309
ChemSpider 553855 YesY
ChEBI CHEBI:72578 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C15H8O3
Molar mass 236.22 g mol−1
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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]

Coumestans[edit]

References[edit]

  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. 
  3. ^ Barbour S. Warren; Carol Devine (July 2001). "Phytoestrogens and Breast Cancer". Program on Breast Cancer and Environmental Risk Factors. Cornell University. Retrieved 2011-03-19. 
  4. ^ Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA; Lemmen; Carlsson; Corton; Safe; Van Der Saag; Van Der Burg; Gustafsson (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.