Coumestan

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]

Coumestan
Names
IUPAC name
Pterocarp-6a(11a)-en-6-one
Systematic IUPAC name
6H-[1]Benzofuro[3,2-c][1]benzopyran-6-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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 checkY
    Key: JBIZUYWOIKFETJ-UHFFFAOYSA-N checkY
  • 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
  • C1=CC=C2C(=C1)C3=C(O2)C4=CC=CC=C4OC3=O
  • O=C3Oc4ccccc4c2oc1c(cccc1)c23
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).
☒N verify (what is checkY☒N ?)
Infobox references

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
  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. S2CID 32550281.
  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 (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.
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