Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography.
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.
Kim
Yun-Seok
YS
College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa 252-8510, Japan.
Katase
Takao
T
Sekine
Sayaka
S
Inoue
Tadashi
T
Makino
Mitsuko
M
Uchiyama
Taketo
T
Fujimoto
Yasuo
Y
Yamashita
Nobuyoshi
N
D001681:Biological Assay / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D004968:Estrogens, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011960:Receptors, Estrogen / Q000187:drug effects; D015003:Yeasts / Q000187:drug effects / Q000254:growth & development
D004968:Estrogens, Non-Steroidal; D010636:Phenols; D011960:Receptors, Estrogen; C025256:nonylphenol