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]
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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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ChEBI |
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CompTox Dashboard (EPA)
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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).
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Infobox references
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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]
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: CS1 maint: DOI inactive as of March 2024 (link)