Synthesis of Antioxidant Isoflavone Fatty Acid Esters

Synthesis of Selectively Protected Genistein Derivatives

“…Previous attempts at selective functionalization of 1 by action of electrophilic reagents exploited differences in acidity of 7-OH and 4 0 -OH and reversed nucleophilicity of the corresponding anions. [6,7] Although acidity constants for particular phenol groups in 1 seem to be a way apart in solution, (at least two orders of magnitude as calculated for 7-OH and 4 0 -OH) lack of solubility of genistein and some of its salts can complicate an issue of selective reactivity for example in the case of phase transfer reactions. In fact, it has been demonstrated with the help of X-ray crystallography and molecular modeling, that basic nitrogen interactions with less acidic phenolic groups also contribute significantly to the structure of molecular complexes between genistein and amines.…”

Crystal structure of di(potassium 2-(2-ethoxy-2-oxoethoxy)-5-(7-(2-ethoxy- 2-oxoethoxy)-4-oxo-4H-chromen-3-yl)benzenesulfonate), C23H21KO11S

“…In the last decade, much attention has been focused on daidzein and its derivatives. Somes tudies have shown that somed aizein derivatives possessed awiderange of biological activities such as estrogenic activity, anti-esrogenic activity [2], antioxidation [3], and antialcohol-addiction [4].Itwas reported thatthe biological activities of isoflavonesulfonates areb etter as those of the parent flavonoids,because adifferentsolubility effectsits biological utilization rate [5].The titlestructure consistsofdouble-chains. The results indicated that thereare twoindependent K + centersshowingthe same coordination environments.…”

Synthesis of Lipophilic Genistein Derivatives and Their Regulation of IL‐12 and TNF‐α in Activated J774A.1 Cells

“…The 5-OH group is the less nucleophilic of genistein. Because of this difference in reactivity, it is easy to make substitutions at 4¢-OH or ⁄ and 7-OH positions (16,17).…”

“…All the compounds were characterized by infrared and NMR experiments. The assignments of the NMR spectra of 1 H and 13 C of compounds 2-5 were based on the work of Lewis et al (16), who synthesized mono-and diesters of genistein and with the help of the X-ray analysis assigned the signs of the 1 H and 13 C NMR spectra. When substituted in the 7-OH position of the genistein, the signs corresponding to H 6 and H 8 appear near d 6.59 and 6.77, respectively.…”