Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography

Chemosphere. 2004 Feb;54(8):1127-34. doi: 10.1016/j.chemosphere.2003.09.024.

Abstract

Estrogenic activity by recombinant yeast screen assay of the commercial NP was considerably higher when compared with that of n-nonylphenol (n-NP). Fractionation of the commercial NP by high performance liquid chromatography (HPLC) afforded seven isomers: 4-(1,3-dimethyl-1-propyl-butyl)-phenol, 4-(1,1,3-trimethyl-hexyl)-phenol, 4-(1,1-dimethyl-3-ethyl-pentyl)-phenol, 4-(1,1,4-trimethyl-hexyl)-phenol, 4-(1-methyl-1-propyl-pentyl)-phenol, 4-(1,1,2-trimethyl-hexyl)-phenol and 4-(1-ethyl-1-methyl-hexyl)-phenol. The structures of these isomers were determined by GC-MS and nuclear magnetic resonance spectroscopy (NMR). All of these isomers possessed tertiary alpha-carbon in their chemical structures. Another tertiary NP, 4-(1,1-dimethyl-heptyl)-phenol was synthesized in the present study and this synthetic NP also exhibited the estrogenic activity. One fractionated compound was identified as one of decylphenol, 4-(1-ethyl-1,4,4-trimethyl-pentyl)-phenol. The isomer, 4-(1,1,4-trimethyl-hexyl)-phenol exhibited the highest estrogenic activity corresponding to 1/10000 that of 17beta-estradiol (E2). The activity of n-NP was the least. This suggests that it may be possible to develop a technical NP mixture with relatively low estrogenic activity.

MeSH terms

  • Biological Assay / methods
  • Chromatography, High Pressure Liquid
  • Estrogens, Non-Steroidal / chemistry
  • Estrogens, Non-Steroidal / isolation & purification
  • Estrogens, Non-Steroidal / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Phenols / chemistry
  • Phenols / isolation & purification
  • Phenols / pharmacology*
  • Receptors, Estrogen / drug effects
  • Yeasts / drug effects
  • Yeasts / growth & development

Substances

  • Estrogens, Non-Steroidal
  • Phenols
  • Receptors, Estrogen
  • nonylphenol