Optical Resolution and Absolute Configuration of Branched 4-Nonylphenol Isomers and Their Estrogenic Activities

This is the authors' abstract. We don't add key points for this paper.

To determine the effects of optical isomerism on the estrogenic activity of 4-nonylphenol (NP) isomers, four optically active NP isomers, (3R)-4-(3-ethyl-2-methylhexan-2-yl)phenol, (3S)-4-(3-ethyl-2-methylhexan-2-yl)phenol, (4R)-4-(2,4-dimethylheptan-4-yl)phenol and (4S)-4-(2,4-dimethylheptan-4-yl)phenol, were prepared and separated using chiral HPLC. Their absolute configurations were elucidated by X-ray crystallographic analysis of their bromobenzoylated derivatives. The estrogenic activities (recombinant yeast screen assay) of the optically active NPs were similar to those of the corresponding racemates.