Alkylphenolic compounds

Those man-made chemicals which have been identified as being oestrogenic belong to several major groups of chemicals including organochlorine pesticides, polychlorinated biphenyls, alkylphenolic compounds, ... 

Petrovic M, Lacorte S, Viana P, Barcelo D (2002) Pressurized liquid extraction followed by liquid chromatography-mass spectrometry for the determination of alkylphenolic compounds in river sediment. J Chromatogr A 959 15-23... 

Fig. 2.6.18. LC-MS-MS analysis of halogenated alkylphenolic compounds in chlorinated river water (the Llobregat river, Spain). MRM mode (a) 253 —> 167 for detection of 35C1 nonylphenolic compounds (b) 297 — 79 for 79BrNP (c) 355 —> 297 for 79BrNPE C (d) 399 — 297 for 79BrNPE2C. Reprinted with permission from Ref. [39] 2002 American...

Wastewater-derived alkylphenolic compounds have been studied extensively. The concentrations of nonylphenol ethoxylates (NPEOs), as the strongly prevalent sub-group of APEOs, determined in the influents of WWTPs (Table 6.1.4), varied widely among various WWTPs from <30 to 1035 pg L 1. However, values can go up to 22 500 pg L-1 in industrial wastewaters (especially from tannery, textile, pulp and paper industry). Levels of octylphenol ethoxylates (OPEOs) are significantly lower, comprising approximately 5-15% of total APEOs in WWTP influents, which is congruent with their lower commercial use. 

The occurrence of APEO or their metabolites (AP and carboxylated derivatives) was also studied in two tributaries of the Llobregat river (northeastern Spain). The Llobregat river is one of the most important sources of drinking water for the Barcelona area with a population of 3.2 million people. Since 1960, the effluents from tannery, textile, pulp and paper industries, situated along the river basin, have discharged into the river and several comprehensive studies [15—17] have been performed in order to determine the levels of estrogenic alkylphenolic compounds (and steroid sex hormones) and to study the effects of WWTP effluents on the reproductive physiology of fish. 

Fig. 6.2.3. Seasonal variation of alkylphenolic compounds in water (A) and sediment (B) samples from the Anoia river. Sampling points A1 (1.5 km upstream of WWTP, Igualada) A2 (23 km downstream of WWTP) A3 (27 km downstream of WWTP).

However, an issue of concern is the relatively high level of alkylphenolic compounds in both water and sediment upstream of known sources of pollution (WWTPs). The concentrations of total alkylphenolic compounds (APEO, AP and APEC) ranged from 5 to 15 jxg L-1 in water and from 0.075 to 0.55 xg g-1 in sediments, and may be attributed mainly to two origins. One is the use of sewage sludge in agriculture and the other is the uncontrolled discharge of industrial wastewaters in the upper course of the river. 

White, R., Jobling, S., Hoarse, S.A., Sumpter, J.P., Parker, M.G., 1994. Environmentally persistent alkylphenolic compounds are estrognic. Endocrinology 135, 175-182. 

M. Petrovic, S. Tavazzi, D. Barceld, Column-switching system with restricted access pre-column packing for an integrated sample cleanup and LCHdS analysis of alkylphenolic compounds and steroid sex hormones in sediment, J. Chromatogr. A, 971... 

Propofol is an alkylphenol compound that is highly lipid soluble but water insoluble. Its lipid solubility allows rapid penetration of the blood-brain barrier after i.v. administration, with rapid onset of CNS effects. This physicochemical property also means that rapid redistribution of propofol from the brain to other body tissues plays a significant role in the termination of the anesthetic effect. 

Hoare SA, Jobling S, Parker MG, Sumpter JP, White R. Environmental persistent alkylphenolic compounds are estrogenic. Endocrinology 1994 135 175-82. 

Bennett, E.R. and C.R. Metcalfe. Distribution of alkylphenol compounds in Great Lakes sediments, United States and Canada. Environ. Toxicol. Chem. 17 1230-1235, 1998. 

Ginkgo leaf contains ginkgolic acids (urushiol type alkylphenols), compounds that are related to those found in poison ivy Toxicodendron radicans) and associated with contact allergies, especially dermatitis. Ginkgolic acids are found in relatively high concentrations in ginkgo seed coats and in low concentrations in the leaf (Blumenthal 1997). 

Among different nonionic surfactant classes, alkyl-phenol ethoxylates (APEOs) comprise the class meriting special attention with respect to environmental issues. The analysis of underivatized alkylphenolic compounds by GC-MS is restricted to the most volatile degradation products, such as alkylphenols and APEOs with less then 4-ethoxy groups. To overcome the problem of volatility, different offline and online derivatization protocols have been developed. Two complementary MS techniques, one using El and another using the less commonly used positive (P)CI, have been evaluated for the analysis of APEOs, their acidic (APECs) and neutral metabolites (APs), and halogenated derivatives. 

List of Ions Monitored in SIM and MRM Modes for the Analysis of Alkylphenolic Compounds and Their Halogenated Derivatives... 

Wang JL, Liu CS, Lin KL et al (2005) Nonylphenol-induced Ca " elevation and Ca -independent cell death in human osteosarcoma cells. Toxicol Lett 160(l) 76-83 White R, Jobling S, Hoare SA et al (1994) Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135(1) 175-182... 

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