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J.Health Sci., 53(2), 177-184, 2007
Optical Resolution and Absolute Configuration of Branched 4-Nonylphenol Isomers and Their Estrogenic Activities
Hiroaki Saito,a Taketo Uchiyama,*, a
Mitsuko Makino,b Takao Katase,c
Yasuo Fujimoto,b and Daisuke Hashizumed
aCollege of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan,
bCollege of Humanities and Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan,
cCollege of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa 252-8510, Japan, and
dRIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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.
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