Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures

Russ, Alexander; Vinken, Ralph; Schuphan, Ingolf; Schmidt, Burkhard

doi:10.1016/j.chemosphere.2005.02.046

Cited by 59 publications

(17 citation statements)

References 33 publications

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“…The mixtures of (ortho-, para-)hexyl-and heptylphenols were synthesised to determine xenoestrogenic paraisomers of long-chained alkylphenols in produced water and compare their relative amount to that of their less potent ortho-and meta-isomers. It has been observed for technical nonylphenol, representing a mixture of known nonylphenol isomers (Ruß et al, 2005), when derivatised with PFBC and analysed together with other standards, that the majority of para-isomers have APRI values in the range of 7.1-7.7, eluting in a narrow chromatographic ''window'' as a cluster of peaks. These are strongly branched alkylphenols, while para-nnonylphenol has APRI = 9.…”

Section: Alkylphenolsmentioning

confidence: 98%

Identification of estrogen-like alkylphenols in produced water from offshore oil installations

Boitsov

Mjøs

Meier

2007

Marine Environmental Research

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Section: Alkylphenolsmentioning

confidence: 98%

Identification of estrogen-like alkylphenols in produced water from offshore oil installations

Boitsov

Mjøs

Meier

2007

Marine Environmental Research

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“…The presence of these isomers were good agreement with previous reports. 17,18,25,26) These NP isomers showed lower estrogenic activities than the commercial NP. The other NP isomers in the commercial NP were suggested to possess much higher estrogenic activities compared with the NP isomers synthesized in this study.…”

Section: Estrogenic Activity Of Synthesized Np Isomers In Commercial Npmentioning

confidence: 99%

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

Shioji

Tsunoi

Kobayashi

et al. 2006

JOURNAL OF HEALTH SCIENCE

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Various branched isomers of 4-nonylphenol (NP) and, in addition, the other 4-alkylphenols (APs) were synthesized and their estrogenic activities were assessed using the yeast two-hybrid system. We investigated the relationships between the structure of the nonyl group of NP isomers and their estrogenic activities based on the following five factors: the length of the main alkyl chain, the degree of branching on the α-carbon, the degree of bulkiness, the position of the branch, and the cyclic structure in the nonyl group. An appropriate length of the main alkyl chain was essential for the estrogenic activity. A small effect of the branching on the α-carbon was observed. The importance of the bulkiness and position of the branch in the nonyl group was suggested from the results of the synthesized NP isomers possessing the high estrogenic activities. The bulkiness on the β-carbon was the most important factor for the high estrogenic activity. The investigation of the cyclic structure also indicated the significance of the bulkiness around the β-carbon. The bulkiness on the γ-carbon was also suggested to be an important factor. The metabolic effect of the synthesized APs on the estrogenic activity was also examined using a liver S9. The estrogenic activities of the selected APs were either reduced or lost. In addition, GC-MS analyses of the commercial NP and synthesized NP isomers revealed that the nine synthesized NP isomers were included in the commercial NP.

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“…1a-c, respectively) were chosen as substrates for first studies [21][22][23]. p353NP was shown to have one of the highest estrogenic potencies in assays with MVLN cell lines [24] and to constitute approximately 20% of several commercial technical mixtures [25].…”

Section: Microbial Degradation Of Nonylphenolmentioning

confidence: 99%

The degradation of alkylphenols by Sphingomonas sp. strain TTNP3 – a review on seven years of research

Kolvenbach

Corvini

2012

New Biotechnology

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Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures

Cited by 59 publications

References 33 publications

Identification of estrogen-like alkylphenols in produced water from offshore oil installations

Identification of estrogen-like alkylphenols in produced water from offshore oil installations

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

The degradation of alkylphenols by Sphingomonas sp. strain TTNP3 – a review on seven years of research

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