Octylphenols estrogenicity

Tanghe T, W Dhooge, W Verstraete (2000) Formation of the metabolic intermediate 2,4,5-trimethyl-2-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation 11 11-19. 

This phenomenon may be also important for all natural estrogens and endocrine-disrupting chemicals (EDCs) which are weak acids, such as 17 -estra-diol, estriol, ethynylestradiol, diethylstilbestrol, nonylphenol, octylphenol, bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), hydroxy polychlorinated biphenyls, and other compounds with hydroxylated aromatic rings. 

Environmental chemicals such as p-nonylphenol (NP), 4-ferf.-octylphenol (OP), 4-ferf.-pentylphenol (TPP), bisphenol-A (BPA), tetrabromobisphenol-A (TBBA), butylbenzylphthalate (BBP), di- -butylphthalate (DBP), butylated hydroxyanisole (BHA), p-chloro-ra-cresol, p-chloro-o-cresol, ds-nonachlor, frans-nonachlor, and the herbicide alachlor [2-chloro-iV-(2,6-diethylphenyl)-N-(methoxymethyl) acetamide] have been discovered to be weakly estrogenic [128,129,137,138]. 

Moffat, G.J., A. Bums, J. Van Miller, R. Joiner and J. Ashby. Glucuronidation of nonylphenol and octylphenol eliminates their ability to activate transcription via the estrogen receptor. Regul. Toxicol. Pharmacol. 34 182-187, 2001. 

Lee Ml, Lin H, Liu CW et al (2008) Octylphenol stimulates resistin gene expression in 3T3-L1 adipocytes via the estrogen receptm and extracellular signal-regulated kinase pathways. Am J Physiol CeU Physiol 294(6) C1542-C1551... 

---