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Syntheses and Estrogenic Activity of 4-nonylphenol Isomers

Syntheses and Estrogenic Activity of 4-nonylphenol Isomers

Taketo Uchiyama, Mitsuko Makino, Hiroaki Saito, Takao Katase, Yasuo Fujimoto

Chemosphere. 2008 Aug;73(1 Suppl):S60-5.

PMID: 18439648

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS26418	4-(1-Methyl-1-propylpentyl)phenol			Price

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