Chemistry:Coumestan
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| IUPAC name
Pterocarp-6a(11a)-en-6-one
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| Systematic IUPAC name
6H-[1]Benzofuro[3,2-c][1]benzopyran-6-one | |
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3D model (JSmol)
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| Properties | |
| C15H8O3 | |
| Molar mass | 236.22 g/mol |
| Melting point | 187 to 188 °C (369 to 370 °F; 460 to 461 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| 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
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.
- ↑ "Phytoestrogens and Breast Cancer". Program on Breast Cancer and Environmental Risk Factors. Cornell University. July 2001. http://envirocancer.cornell.edu/FactSheet/Diet/fs1.phyto.cfm#1.
- ↑ "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta". Endocrinology 139 (10): 4252–4263. 1998. doi:10.1210/endo.139.10.6216. PMID 9751507. http://endo.endojournals.org/cgi/content/full/139/10/4252.
- ↑ 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.
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