Endocrine disrupting chemicals, bisphenol

Rosenfeldt EJ, Linden KG (2004) Degradation of endocrine disrupting chemicals bisphenol A, ethinyl estradiol, and estradiol during UV photolysis and advanced oxidation processes. Environ Sci Technol 38 5476-5483... 

Lang lA, Galloway TS, Scarlett A et al (2008) Association of urinary bisphenol A concentration with medical disorders and laboratory abnormalities in adults. JAMA 300(11) 1303-1310 Li DK, Zhou Z, Miao M et al (2010) Relationship between urine bisphenol-A (BPA) level and declining male sexual function. J Androl l(13) 5(X)-506 Li Y, Bums KA, Arao Y et al (2012) Differential estrogenic actions of endocrine-disrupting chemicals bisphenol A, bisphenol AF, and zearalenone through estrogen receptor in vitro. Environ Health Perspect 120(7) 1029-1035... 

Fernandez, M.F., Rivas, A., and Pulgar, R. et al. (2001). Human exposure to endocrine disrupting chemicals The case of bisphenols. Endocrine Disrupters 18, 149-169. 

From the wide variety of emerging pollutants of industrial origin that could be considered here, bisphenol A (BPA) and phthalate esters (PE) are of especial relevance not only because of the high volumes produced and their widespread use, but also because of their demonstrated toxicity, particularly as endocrine disrupters. Both of them have been included in the final report of the European Commission toward the establishment of a priority list of endocrine disrupter chemicals, EDCs [3], and have been rated as of high risk of exposure for human and wildlife populations. Because of their structural characteristics these compounds cannot be included in any of the groups described above, so they will be described in this section (see Fig. 10). 

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. 

Manganese-oxide materials have been reported as efficient oxidants for the degradation of endocrine disruptive chemicals such as estrone, 17jS-estradiol, bisphenol A and bisphenol F, among others. Xu et al. studied the oxidative removal of several endocrine disruptors from water using synthetic 5-Mn02 (surface area = 128 m g ) as well as the factors that influenced its... 

McLachlan JA (2001) Environmental signaling what embryos and evolution teach us about endocrine disrupting chemicals. Endocr Rev 22(3) 319-341 Meeker JD, Calafat AM, Hauser R (2010a) Urinary bisphenol A concentrations in relation to serum thyroid and reproductive hormone levels in men from an infertility clinic. Environ Sd Technol 44(4) 1458-1463... 

Results for endocrine disrupting phenols in house dust as reported by Rudel et al. (2003) and Butte et al. (2001) are compiled in Table 11.1. Rudel et al. (2003) sampled indoor air in 120 homes as well. They analyzed both house dust and air for 89 organic chemicals identified as EDCs. The most abundant compounds in air included 4-nonylphenol and 4-t-butylphenol with typical concentrations in the range of 0.050-1.500ggm 3. Saito, Onuki and Seto (2004) collected air samples from houses, offices, and outdoor points. 4-t-butylphenol, 4-t-octylphenol and 4-nonylphenol were detected in both indoor and outdoor air. Concentrations and detection frequencies were higher in indoor air than outdoor air. The maximum levels of 4-t-butylphenol, 4-t-octylphenol and 4-nonylphenol in indoor air were 0.387, 0.0457 and 0.680 ggm 3, respectively. 4-t-butylphenol and 4-nonylphenol were detected with high frequencies (more than 97%) in the indoor air samples. Wilson, Chuang and Lyu (2001) reported a mean of 0.0007 gg m"3 Bisphenol A in the air of 10 child care centers and a mean of 0.203 gg m 3 for the sum of nonylphenol and its ethoxylates. 

Among the emerging pollutants of industrial origin, Bisphenol A [2,2 bis(4-hydroxydiphenyl)pro-pane] (BPA) has special relevance since it was one of the first chemicals discovered to mimic estrogens as endocrine disrupters.147 This compound was first reported by Dianin in 1891.1411 BPA is produced in large quantities worldwide, mainly for the preparation of polycarbonates, epoxy resins, and unsaturated polyester-styrene resins.149 The final products are used in many ways, such as coatings on cans, powder paints, additives in thermal paper, in dental composite fillings, and even as antioxidants in plasticizers or polymerization inhibitors in polyvinyl chloride (PVC). To a minor extent, BPA is also used as precursor for flame retardants such as tetrabromobisphenol A or tetrabromobisphenol-S-bis(2,3-dibromopropyl) ether.150 This substance can enter the environment... 

Fig. 9. Relationship between the steady-state bioconcentration factors on a lipid basis (BCFl) of chemicals in different fish species and the n-octanol/water partition coefficient (Kqw) (log/log scale). ( ) Solid circles are chemicals with known endocrine-disrupting properties. Abbreviations of the chemicals p,p -DDT 2,2-bis-(p-chlorophenyl)-l,l,l-trichloroethane. OCDD octachlorodibenzo-p-dioxin. TCDD tetrachlorodibenzo-p-dioxin. HCB hexachloro-benzene. PCA pentachloroanisole. PeCB pentachlorobenzene. MX musk xylene. TeCB tetrachlorobenzene. NP nonylphenol. TCB tetrachlorobenzene. y-HCH y-hexachlorocyclo-hexane (Lindane). PCP pentachlorophenol. DCB dichlorobenzene. BPA bisphenol-A. PCBs polychlorinated biphenyls...

Both decaBDE and BPADP stopped at Benchmark 1 because of their breakdown products. DecaBDE s breakdown products include pentaBDE as a PBT (Benchmark 1 (a)) and octaBDE as very persistent and toxic. BPADP degrades into bisphenol A (and contains the chemical as a contaminant in formulations), which is of high concern for endocrine disruption (and potentially high for its reproductive and developmental effects). 

BPADP/BAPP and its breakdown products 181028-79-5 Breakdown product and formulation contaminant, bisphenol A, is of high concern for endocrine disruption—stopping BPADP at Benchmark 1(d) Benchmark 1 Avoid—Chemical of Eligh Concern... 

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