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Chemical Compound Review

SureCN11668767     4-(2,6-dimethylheptyl)phenol

Synonyms: CTK1I8283, KB-237369, AC1NR4TE, 63085-63-2, Phenol, 4-(2,6-dimethylheptyl)-
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Disease relevance of Nonylphenol

  • Several nonylphenol isomers with alpha-quaternary carbon atoms serve as growth substrates for Sphingomonas xenophaga Bayram, whereas isomers containing hydrogen atoms at the alpha-carbon do not [1].
  • Average recoveries ranging from 72 to 95% were obtained using the SSPE methodology for ubiquitous analytes such as poly(ethylene glycol)s, nonylphenol and alcohol polyethoxylates, phenols, linear alkylbenzenesulfonates, and benzene- and naphthalenesulfonates [2].
  • Mechanism for biotransformation of nonylphenol polyethoxylates to Xenoestrogens in Pseudomonas putida [3].
  • Maternal and offspring toxicity but few sexually dimorphic behavioral alterations result from nonylphenol exposure [4].
  • Nonylphenol exposure increased mortality rates, elicited stress behaviors, decreased body weight and significantly hampered gonadal development and reproductive function [5].

Psychiatry related information on Nonylphenol

  • Two potential endocrine-disrupting chemicals, bisphenol A (BPA) and nonylphenol (NP), were assessed for their long-lasting effects on endocrine/reproductive systems following transplacental and lactational exposure to rat offspring during a time-window that included the critical period for brain sexual differentiation [6].

High impact information on Nonylphenol


Chemical compound and disease context of Nonylphenol


Biological context of Nonylphenol


Anatomical context of Nonylphenol


Associations of Nonylphenol with other chemical compounds

  • An immunoassay for E2 did not detect the NP in treated monkeys [23].
  • The phytoestrogen levels were compared with both baseline uterine weights of the control groups and with the relative uterine weight increase of groups administered two weak estrogen agonists: bisphenol A (BPA) and nonylphenol (NP) [24].
  • This Environmental Health Perspectives mini-monograph is devoted to the phase 2 work using five weak estrogen agonists, bisphenol A, genistein, methoxychlor, nonylphenol, and o,p -DDT, as well as the negative substance dibutylphthalate [25].
  • Immunochemical analysis of plasma from Atlantic salmon (Salmo salar) exposed to 4-nonylphenol (NP) or to effluent from oil refinery treatment plant (ORTP), shows that NP and ORTP effluent induces Vtg and zona radiata proteins (Zrp) in a dose-dependent manner [26].
  • Co-incubation of embryos with the pure antiestrogen ICI 182,780 blocked the ability of nonylphenol to induce abnormalities in body shape and in melanocyte differentiation but did not block the effects of methoxychlor [27].

Gene context of Nonylphenol


Analytical, diagnostic and therapeutic context of Nonylphenol

  • Simultaneous determination of linear alkylbenzenesulfonates, alkylphenol polyethoxylates, and nonylphenol by high-performance liquid chromatography [31].
  • The cell-based bioassay also did not detect the estrogenic activity of NP because of its saturation by the endogenous serum steroidal estrogens [23].
  • 5. We suggest a dual role for the nonylphenol ethoxylate surfactant in the coculture: (i) to improve hydrocarbon uptake by strain JA5-B45 through emulsification and (ii) to prevent strain F9-D79 from adhering to the oil-water interface, indirectly increasing hydrocarbon availability [32].
  • However, when steroidal estrogens were removed by immunoprecipitation, we detected the estrogenic activity of NP in the bioassay [23].
  • Fate of a 14C-labeled nonylphenol isomer in a laboratory-scale membrane bioreactor [33].


  1. A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram: ipso-hydroxylation and intramolecular rearrangement. Gabriel, F.L., Heidlberger, A., Rentsch, D., Giger, W., Guenther, K., Kohler, H.P. J. Biol. Chem. (2005) [Pubmed]
  2. Identification of polar toxicants in industrial wastewaters using toxicity-based fractionation with liquid chromatography/mass spectrometry. Castillo, M., Barceló, D. Anal. Chem. (1999) [Pubmed]
  3. Mechanism for biotransformation of nonylphenol polyethoxylates to Xenoestrogens in Pseudomonas putida. John, D.M., White, G.F. J. Bacteriol. (1998) [Pubmed]
  4. Maternal and offspring toxicity but few sexually dimorphic behavioral alterations result from nonylphenol exposure. Ferguson, S.A., Flynn, K.M., Delclos, K.B., Newbold, R.R. Neurotoxicology and teratology. (2000) [Pubmed]
  5. Endocrine disruption caused by two common pollutants at "acceptable" concentrations. Magliulo, L., Schreibman, M.P., Cepriano, J., Ling, J. Neurotoxicology and teratology. (2002) [Pubmed]
  6. Lack of maternal dietary exposure effects of bisphenol A and nonylphenol during the critical period for brain sexual differentiation on the reproductive/endocrine systems in later life. Takagi, H., Shibutani, M., Masutomi, N., Uneyama, C., Takahashi, N., Mitsumori, K., Hirose, M. Arch. Toxicol. (2004) [Pubmed]
  7. Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription. Masuyama, H., Hiramatsu, Y., Kunitomi, M., Kudo, T., MacDonald, P.N. Mol. Endocrinol. (2000) [Pubmed]
  8. The endocrine-disrupting compound, nonylphenol, inhibits neurotrophin-dependent neurite outgrowth. Bevan, C.L., Porter, D.M., Schumann, C.R., Bryleva, E.Y., Hendershot, T.J., Liu, H., Howard, M.J., Henderson, L.P. Endocrinology (2006) [Pubmed]
  9. Nonylphenol induces the death of neural stem cells due to activation of the caspase cascade and regulation of the cell cycle. Kudo, C., Wada, K., Masuda, T., Yonemura, T., Shibuya, A., Fujimoto, Y., Nakajima, A., Niwa, H., Kamisaki, Y. J. Neurochem. (2004) [Pubmed]
  10. Mechanism of inhibition of the calcium pump of sarcoplasmic reticulum by thapsigargin. Wictome, M., Henderson, I., Lee, A.G., East, J.M. Biochem. J. (1992) [Pubmed]
  11. Aquatic toxicity of nine aircraft deicer and anti-icer formulations and relative toxicity of additive package ingredients alkylphenol ethoxylates and 4,5-methyl-1H-henzotriazoles. Corsi, S.R., Geis, S.W., Loyo-Rosales, J.E., Rice, C.P. Environ. Sci. Technol. (2006) [Pubmed]
  12. Interspecies correlation estimates predict protective environmental concentrations. Dyer, S.D., Versteeg, D.J., Belanger, S.E., Chaney, J.G., Mayer, F.L. Environ. Sci. Technol. (2006) [Pubmed]
  13. Alterations in phospholipid bilayers caused by oxyethylenated nonylphenol surfactants. de la Maza, A., Parra, J.L. Arch. Biochem. Biophys. (1996) [Pubmed]
  14. The contribution of hepatic steroid metabolism to serum estradiol and estriol concentrations in nonylphenol treated MMTVneu mice and its potential effects on breast cancer incidence and latency. Acevedo, R., Parnell, P.G., Villanueva, H., Chapman, L.M., Gimenez, T., Gray, S.L., Baldwin, W.S. Journal of applied toxicology : JAT. (2005) [Pubmed]
  15. Assessment of pubertal development in juvenile male rats after sub-acute exposure to bisphenol A and nonylphenol. Tan, B.L., Kassim, N.M., Mohd, M.A. Toxicol. Lett. (2003) [Pubmed]
  16. Mechanism of inhibition of the (Ca2(+)-Mg2+)-ATPase by nonylphenol. Michelangeli, F., Orlowski, S., Champeil, P., East, J.M., Lee, A.G. Biochemistry (1990) [Pubmed]
  17. Tissue-specific estrogenic and non-estrogenic effects of a xenoestrogen, nonylphenol. Watanabe, H., Suzuki, A., Goto, M., Lubahn, D.B., Handa, H., Iguchi, T. J. Mol. Endocrinol. (2004) [Pubmed]
  18. Influence of xenobiotics on rainbow trout liver estrogen receptor and vitellogenin gene expression. Flouriot, G., Pakdel, F., Ducouret, B., Valotaire, Y. J. Mol. Endocrinol. (1995) [Pubmed]
  19. Nonylphenol alters connexin 43 levels and connexin 43 phosphorylation via an inhibition of the p38-mitogen-activated protein kinase pathway. Aravindakshan, J., Cyr, D.G. Biol. Reprod. (2005) [Pubmed]
  20. p-Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene. Soto, A.M., Justicia, H., Wray, J.W., Sonnenschein, C. Environ. Health Perspect. (1991) [Pubmed]
  21. Induction of calbindin-D9k messenger RNA and protein by maternal exposure to alkylphenols during late pregnancy in maternal and neonatal uteri of rats. Hong, E.J., Choi, K.C., Jeung, E.B. Biol. Reprod. (2004) [Pubmed]
  22. Targeted Salmon Gene Array (SalArray): A Toxicogenomic Tool for Gene Expression Profiling of Interactions Between Estrogen and Aryl Hydrocarbon Receptor Signalling Pathways. Mortensen, A.S., Arukwe, A. Chem. Res. Toxicol. (2007) [Pubmed]
  23. Detection of xenoestrogens in serum after immunoprecipitation of endogenous steroidal estrogens. Natarajan, K., Overstreet, J.W., Rogers, J.M., Denison, M.S., Chen, J., Lohstroh, P.N., McConnell, D.S., Lasley, B.L. Environ. Health Perspect. (2002) [Pubmed]
  24. The OECD program to validate the rat uterotrophic bioassay. Phase 2: dietary phytoestrogen analyses. Owens, W., Ashby, J., Odum, J., Onyon, L. Environ. Health Perspect. (2003) [Pubmed]
  25. The OECD program to validate the rat uterotrophic bioassay: an overview. Owens, W., Koëter, H.B. Environ. Health Perspect. (2003) [Pubmed]
  26. Fish zona radiata (eggshell) protein: a sensitive biomarker for environmental estrogens. Arukwe, A., Knudsen, F.R., Goksøyr, A. Environ. Health Perspect. (1997) [Pubmed]
  27. Environmental estrogens alter early development in Xenopus laevis. Bevan, C.L., Porter, D.M., Prasad, A., Howard, M.J., Henderson, L.P. Environ. Health Perspect. (2003) [Pubmed]
  28. Estrogenic effects of nonylphenol on pS2, ER and MUC1 gene expression in human breast cancer cells-MCF-7. Ren, L., Marquardt, M.A., Lech, J.J. Chem. Biol. Interact. (1997) [Pubmed]
  29. Inhibition of human hepatic cytochrome P450s and steroidogenic CYP17 by nonylphenol. Niwa, T., Maekawa, Y., Fujimoto, M., Kishimoto, K., Yabusaki, Y., Ishibashi, F., Katagiri, M. Biol. Pharm. Bull. (2002) [Pubmed]
  30. Metabolism of 4-n-nonylphenol by non-modified and CYP1A1- and CYP1A2-transgenic cell cultures of tobacco. Berger, A., S Russ, A., Schuphan, I., Schmidt, B. Z. Naturforsch., C, J. Biosci. (2005) [Pubmed]
  31. Simultaneous determination of linear alkylbenzenesulfonates, alkylphenol polyethoxylates, and nonylphenol by high-performance liquid chromatography. Marcomini, A., Giger, W. Anal. Chem. (1987) [Pubmed]
  32. Physical and metabolic interactions of Pseudomonas sp. strain JA5-B45 and Rhodococcus sp. strain F9-D79 during growth on crude oil and effect of a chemical surfactant on them. Van Hamme, J.D., Ward, O.P. Appl. Environ. Microbiol. (2001) [Pubmed]
  33. Fate of a 14C-labeled nonylphenol isomer in a laboratory-scale membrane bioreactor. Cirja, M., Z??hlke, S., Ivashechkin, P., Sch??ffer, A., Corvini, P.F. Environ. Sci. Technol. (2006) [Pubmed]
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