Coumestan

Coumestan
IUPAC name [1]Benzoxolo[3,2-c]chromen-6-one
Identifiers
CAS number	479-12-9
PubChem	638309
ChemSpider	553855 Y
Jmol-3D images	Image 1 Image 2
SMILES C1=CC=C2C(=C1)C3=C(O2)C4=CC=CC=C4OC3=O O=C3Oc4ccccc4c2oc1c(cccc1)c23
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 Y Key: JBIZUYWOIKFETJ-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C15H8O3
Molar mass	236.22 g mol−1
Melting point	187-188 °C[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Coumestan is an organic compound that is a derivative of coumarin. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. 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.^[2]

Coumestol has about the same binding affinity for the ER-β estrogen receptor as 17β-estradiol, but much less affinity for 17α-estradiol, although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.^[3]

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.^[4][5]

Coumestans

• 

  Coumestrol

• 

  Wedelolactone

• 

  Plicadin

References

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. ^ Barbour S. Warren, Research Associate, BCERF & Carol Devine, Ph.D., R.D., Educational Project Leader, BCERF (revised July 2001). "Cornell University". Program on Breast Cancer and Environmental Risk Factors. Cornell University. http://envirocancer.cornell.edu/FactSheet/Diet/fs1.phyto.cfm#1. Retrieved 2011-03-19. 
3. ^ 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/en.139.10.4252. PMID 9751507. http://endo.endojournals.org/cgi/content/full/139/10/4252. 
4. ^ 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. 
5. ^ 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.