1036738-38-1Relevant academic research and scientific papers
Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking
Zago, Erika,Dubreucq, Eric,Lecomte, Jér?me,Villeneuve, Pierre,Fine, Frédéric,Fulcrand, Hélène,Aouf, Chahinez
, p. 7701 - 7710 (2016)
Diepoxydized diphenyls from eugenol, 4-vinyl guaiacol and 4-vinyl syringol (canolol) were synthesized as sustainable alternatives to the diglycidyl ether of bisphenol A (DGEBA). In the first step, glycidylated derivatives were produced by reaction with epichlorohydrin. Then, the dimerization of these derivatives was performed by cross metathesis (CM) reaction in the presence of the Grubbs II catalyst. From the CM reaction, a set of epoxy phenolic dimers was obtained in good yields with a high diastereoselectivity. Estimation by molecular docking calculations of the affinity of the synthesized products and their hydrolysed structures to the intranuclear estrogen receptor ERα showed that the epoxy forms presented a moderate affinity to the antagonistic conformation of the receptor (six to forty times lower than bisphenol A and in the same order of magnitude as DGEBA) and mostly no binding in the agonist conformation. The hydrolysed forms of the epoxy products, which are expected to be predominant in the human body cells, exhibited a relatively weak affinity to the ERα LBD in its both agonistic and antagonistic conformations.
METHOD FOR PREPARING GLYCIDYLOXYSTYRENE MONOMERS AND POLYMERS THEREOF
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, (2008/12/06)
It was found that glycidyloxystyrenes, including glycidyloxystyrene and substituted glycidyloxystyrene, can be synthesized from hydroxycinnamic acid or substituted hydroxycinnamic acids in a one-pot, two-step process. The substrate can be thermally decarboxylated and then without purification, reacted in the presence of a halomethyl-oxirane and a base. The resulting product can be polymerized or coppolymerized to a fully substituted product.
