Syntheses and estrogenic activity of 4-nonylphenol isomers.
Syntheses and estrogenic activity of 4-nonylphenol isomers.
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DOI：
10.1016/j.chemosphere.2006.12.103
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发表时间：
2008-08
期刊：
影响因子：
8.8
通讯作者：
T. Uchiyama;M. Makino;Hiroaki Saito;T. Katase;Y. Fujimoto
中科院分区：
文献类型：
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作者：
T. Uchiyama;M. Makino;Hiroaki Saito;T. Katase;Y. Fujimoto
八种支链4-壬基苯酚(NP)异构体，从市售NP试剂中鉴定出，4-(1-乙基-1,4-二甲基戊基)苯酚(NP-C)、4-(1,1-二甲基-3-乙基戊基)苯酚(NP-D)、4-(1,3-二甲基-1-乙基戊基)苯酚(NP-E(G))，非对映异构体混合物)， 4-(1,1,4-三甲基己基)苯酚(NP-F)、4-(1-甲基-1-正丙基戊基)苯酚(NP-H)、4-(1,1-二甲基-2-乙基戊基)苯酚(NP-I)、4-(1,1,2-三甲基己基)苯酚(NP-M)和4-(1-乙基-1-甲基己基)苯酚(NP-N)通过以下方法合成以 4-苄氧基苯乙酮或苯酚为原料的两种不同的合成方法。合成化合物的化学结构通过MS和NMR波谱证实。对这些合成的NP异构体的雌激素活性进行了测试，并在重组酵母筛选系统上表现出不同的活性。发现 NP-I 的雌激素活性是商业 NP 混合物的三倍。
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.