title: Syntheses and estrogenic activity of 4-nonylphenol isomers.
abstract: Eight branched 4-nonylphenol (NP) isomers, which were identified from commercially available NP reagent, 4-(1-ethyl-1,4-dimethylpentyl)phenol (NP-C), 4-(1,1-dimethyl-3-ethylpentyl)phenol (NP-D), 4-(1,3-dimethyl-1-ethylpentyl)phenol (NP-E(G)), diastereomeric mixture), 4-(1,1,4-trimethylhexyl)phenol (NP-F), 4-(1-methyl-1-n-propylpentyl)phenol (NP-H), 4-(1,1-dimethyl-2-ethylpentyl)phenol (NP-I), 4-(1,1,2-trimethylhexyl)phenol (NP-M), and 4-(1-ethyl-1-methylhexyl)phenol (NP-N), were synthesized by two different synthetic methods starting from 4-benzyloxyacetophenone or phenol. The chemical structures of the synthesized compounds were confirmed by MS and NMR spectroscopy. The estrogenic activities of these synthetic NP isomers were tested and exhibited different activities on the recombinant yeast screen system. NP-I was found to exhibit three times greater estrogenic activity than the commercial NP mixture.
authors.affiliation: College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba 274-8555, Japan. uctaketo @pha.nihon-u.ac.jp
authors.forename: Taketo
authors.initials: T
authors.lastname: Uchiyama
authors.forename: Mitsuko
authors.initials: M
authors.lastname: Makino
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Saito
authors.forename: Takao
authors.initials: T
authors.lastname: Katase
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: D001681:Biological Assay; D052244:Endocrine Disruptors / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D004967:Estrogens; D006801:Humans; D007536:Isomerism; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D015003:Yeasts / Q000187:drug effects / Q000378:metabolism
chemical_list: D052244:Endocrine Disruptors; D004967:Estrogens; D010636:Phenols; C041594:4-nonylphenol