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Chemical Compound Review

n-Octylphenol     2-octylphenol

Synonyms: o-Octylphenol, SureCN18808, AG-C-95575, CTK2F8065, LS-105014, ...
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Disease relevance of o-Octylphenol


High impact information on o-Octylphenol


Biological context of o-Octylphenol

  • Like 17 beta-estradiol, OP is capable of stimulating the activity of both transcriptional activation functions, TAF-1 and TAF-2, in the receptor, as judged by analyzing the activity of the wild-type and mutant receptors in transiently transfected cells [1].
  • Embryonic exposure of monosex male trout, monosex female trout, and mixed sex salmon to o, o, p'-DDE, p,o, p'-DDE, mixtures of DDE isomers, and octylphenol failed to alter sexual development [7].
  • We exposed tadpoles to the industrial pollutant octylphenol (OP) for 24 hr before and during the critical stages of sexual differentiation to determine whether this known endocrine disruptor affects sex differentiation and SF-1 expression [8].
  • The expression of CaBP-9k mRNA was also induced following treatment with a high dose (600 mg/kg BW) of OP, transferred from the mother, exposed to fetuses during late pregnancy, and persisted through Day 5 of lactation [9].
  • Histology showed increased testis anomalies and decreased spermatozoa with increasing OP exposure [10].

Anatomical context of o-Octylphenol


Associations of o-Octylphenol with other chemical compounds

  • Nonyl- and octylphenols, nonyl- and octylphenol mono-, di-, and triethoxylates, halogenated nonylphenols, and nonylphenol ethoxycarboxylates were concentrated from water samples using a C18 solid-phase extraction procedure [15].
  • However, in the case of the important octylphenol ethoxylates [p-C8H17-C6H4-O-(CH2CH2O)n-H], HPLC cannot resolve individual oligomers of high molecular weight Triton surfactants (e.g., greater than 2000 u or so; u = unified atomic mass unit) [16].
  • Exposure of male mouse fetuses to either dose of bisphenol A, but to neither dose of octylphenol, significantly increased their adult prostate weight relative to control males, which is consistent with the higher predicted bioactivity of bisphenol A than octylphenol in the RBA-SMA assay [17].
  • Quantitative analysis allowed us to compare in vitro and in vivo actions of different estrogenic compounds (estradiol, estrone) and endocrine disruptors (ethynylestradiol, genistein, octylphenol, and 2,4'-dichlorodiphenyldichloroethylene) in the same cell lines and to follow hormone action on a living animal as a function of time [18].
  • In both DES- and OP-exposed fetuses immunoexpression of SF-1 was reduced in Sertoli and interstitial cells when compared with controls [19].

Gene context of o-Octylphenol


Analytical, diagnostic and therapeutic context of o-Octylphenol

  • Temperature was investigated as active parameter in the liquid chromatography (LC) analysis of octylphenol ethoxylates [25].
  • To assess the performance of this immunoassay in complex real samples, a cross reactivity study was carried out, and the possible interference of other surfactants commonly detected in wastewater, including nonylphenol ethoxylates (NPEOs), nonylphenol (NP), octylphenol (OP), and coconut fatty acid diethanol amides (CDEA), have been evaluated [26].
  • Instrumentally determined estrogenic activity (E2-EQ(C)), which is the concentrations of NP and OP multiplied by their corresponding relative potency, was below the detection limit of the MVLN cell bioassay [27].
  • This paper reports the characterization of the biodegradation intermediates of octylphenol octaethoxylate (OP(8)EO) by means of matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) [28].


  1. Environmentally persistent alkylphenolic compounds are estrogenic. White, R., Jobling, S., Hoare, S.A., Sumpter, J.P., Parker, M.G. Endocrinology (1994) [Pubmed]
  2. 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]
  3. Reproductive effects in male and female rats from neonatal exposure to p-octylphenol. Nagao, T., Yoshimura, S., Saito, Y., Nakagomi, M., Usumi, K., Ono, H. Reprod. Toxicol. (2001) [Pubmed]
  4. Amphibians as a model to study endocrine disruptors: II. Estrogenic activity of environmental chemicals in vitro and in vivo. Kloas, W., Lutz, I., Einspanier, R. Sci. Total Environ. (1999) [Pubmed]
  5. Growth factors, kinetics and biodegradation mechanism associated with Pseudomonas nitroreducens TX1 grown on octylphenol polyethoxylates. Chen, H.J., Guo, G.L., Tseng, D.H., Cheng, C.L., Huang, S.L. J. Environ. Manage. (2006) [Pubmed]
  6. Maternal exposure to octylphenol suppresses ovine fetal follicle-stimulating hormone secretion, testis size, and sertoli cell number. Sweeney, T., Nicol, L., Roche, J.F., Brooks, A.N. Endocrinology (2000) [Pubmed]
  7. Salmonid sexual development is not consistently altered by embryonic exposure to endocrine-active chemicals. Carlson, D.B., Curtis, L.R., Williams, D.E. Environ. Health Perspect. (2000) [Pubmed]
  8. Exposure to 4-tert-octylphenol accelerates sexual differentiation and disrupts expression of steroidogenic factor 1 in developing bullfrogs. Mayer, L.P., Dyer, C.A., Propper, C.R. Environ. Health Perspect. (2003) [Pubmed]
  9. 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]
  10. Reproductive effects of estrogenic and antiestrogenic chemicals on sheepshead minnows (Cyprinodon variegatus). Karels, A.A., Manning, S., Brouwer, T.H., Brouwer, M. Environ. Toxicol. Chem. (2003) [Pubmed]
  11. Exposure of newborn male and female rats to environmental estrogens: delayed and sustained hyperprolactinemia and alterations in estrogen receptor expression. Khurana, S., Ranmal, S., Ben-Jonathan, N. Endocrinology (2000) [Pubmed]
  12. Developmental increases in rat hepatic microsomal UDP-glucuronosyltransferase activities toward xenoestrogens and decreases during pregnancy. Matsumoto, J., Yokota, H., Yuasa, A. Environ. Health Perspect. (2002) [Pubmed]
  13. Octylphenol (OP) alters the expression of members of the amyloid protein family in the hypothalamus of the snapping turtle, Chelydra serpentina serpentina. Trudeau, V.L., Chiu, S., Kennedy, S.W., Brooks, R.J. Environ. Health Perspect. (2002) [Pubmed]
  14. Toxic effects of octylphenol on cultured rat spermatogenic cells and Sertoli cells. Raychoudhury, S.S., Blake, C.A., Millette, C.F. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  15. Analysis of alkylphenol ethoxylate metabolites in the aquatic environment using liquid chromatography-electrospray mass spectrometry. Ferguson, P.L., Iden, C.R., Brownawell, B.J. Anal. Chem. (2000) [Pubmed]
  16. Determination of molecular weight distributions of tert-octylphenol ethoxylate surfactant polymers by laser desorption Fourier transform ion cyclotron resonance mass spectrometry and high-performance liquid chromatography. Liang, Z.M., Marshall, A.G., Westmoreland, D.G. Anal. Chem. (1991) [Pubmed]
  17. Relative binding affinity-serum modified access (RBA-SMA) assay predicts the relative in vivo bioactivity of the xenoestrogens bisphenol A and octylphenol. Nagel, S.C., vom Saal, F.S., Thayer, K.A., Dhar, M.G., Boechler, M., Welshons, W.V. Environ. Health Perspect. (1997) [Pubmed]
  18. In vivo bioluminescence imaging to evaluate estrogenic activities of endocrine disrupters. Pillon, A., Servant, N., Vignon, F., Balaguer, P., Nicolas, J.C. Anal. Biochem. (2005) [Pubmed]
  19. Maternal oestrogen/xenoestrogen exposure alters expression of steroidogenic factor-1 (SF-1/Ad4BP) in the fetal rat testis. Majdic, G., Sharpe, R.M., Saunders, P.T. Mol. Cell. Endocrinol. (1997) [Pubmed]
  20. The endocrine disruptors nonylphenol and octylphenol exert direct effects on T cells to suppress Th1 development and enhance Th2 development. Iwata, M., Eshima, Y., Kagechika, H., Miyaura, H. Immunol. Lett. (2004) [Pubmed]
  21. Natural variability and the influence of concurrent control values on the detection and interpretation of low-dose or weak endocrine toxicities. Ashby, J., Tinwell, H., Odum, J., Lefevre, P. Environ. Health Perspect. (2004) [Pubmed]
  22. Octylphenol (OP), an environmental estrogen, stimulates prolactin (PRL) gene expression. Abraham, E.J., Frawley, L.S. Life Sci. (1997) [Pubmed]
  23. Isolation and Characterization of an Alcohol Dehydrogenase Gene from the Octylphenol Polyethoxylate Degrader Pseudomonas putida S-5. Tasaki, Y., Yoshikawa, H., Tamura, H. Biosci. Biotechnol. Biochem. (2006) [Pubmed]
  24. Female infertility--effect of perinatal xenoestrogen exposure on reproductive functions in animals and humans. Götz, F., Thieme, S., Dörner, G. Folia Histochem. Cytobiol. (2001) [Pubmed]
  25. High temperature liquid chromatography and liquid chromatography-mass spectroscopy analysis of octylphenol ethoxylates on different stationary phases. Vanhoenacker, G., Sandra, P. Journal of chromatography. A. (2005) [Pubmed]
  26. Evaluation of a newly developed enzyme-linked immunosorbent assay for determination of linear alkyl benzenesulfonates in wastewater treatment plants. Farré, M., Ramón, J., Galve, R., Marco, M.P., Barceló, D. Environ. Sci. Technol. (2006) [Pubmed]
  27. Contribution of known endocrine disrupting substances to the estrogenic activity in Tama River water samples from Japan using instrumental analysis and in vitro reporter gene assay. Furuichi, T., Kannan, K., Giesy, J.P., Masunaga, S. Water Res. (2004) [Pubmed]
  28. Characterization of biodegradation intermediates of nonionic surfactants by MALDI-MS. 2. Oxidative biodegradation profiles of uniform octylphenol polyethoxylate in 18O-labeled water. Sato, H., Shibata, A., Wang, Y., Yoshikawa, H., Tamura, H. Biomacromolecules (2003) [Pubmed]
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