title: Chlorination of bisphenol F and the estrogenic and peroxisome proliferator-activated receptor gamma effects of its disinfection byproducts.
abstract: The reaction kinetics and transformation pathways between bisphenol F (BPF) and sodium hypochlorite were investigated at pH values ranging from 6.5 to 8.5 and with different initial concentration ratios. The reaction rate was pH- and free available chlorine (FAC)-dependent: the reaction rate at pH 8.5 was almost 10 times than that at pH 6.5. A total of 40 compounds were tentatively identified as chloro-substituted BPF and polyphenolic compounds by liquid chromatography quadrupole time-of-flight mass spectrometry operating in electrospray ionization mode (LC-ESI-Q-ToF), and 4 main byproducts were confirmed by1H and13C nuclear magnetic resonance (NMR). Toxicity tests indicated that the estrogenic effects of chloro-substituted BPF decrease as the chlorine substitution increase. On the contrary, increasing numbers of chlorines on the phenolic rings of BPF enhanced the nuclear receptor peroxisome proliferator-activated receptor gamma (PPARγ) activity. Tetra-chlorinated BPF had an approximately 6.9-fold higher activity than BPF.
authors: Beijing Advanced Innovation Center for Food Nutrition and Human Health, China Agricultural University, Beijing 100193, China; College of Public Health, Capital Medical University, Beijing 100069, China.
authors: Sai
authors: S
authors: Zheng
authors: Beijing Key Laboratory of Diagnostic and Traceability Technologies for Food Poisoning, Beijing Center for Disease Prevention and Control, 100013, China.
authors: Jia-Chen
authors: JC
authors: Shi
authors: College of Urban and Environment Sciences, Peking University, Beijing 1000871, China.
authors: Jian-Ying
authors: JY
authors: Hu
authors: College of Urban and Environment Sciences, Peking University, Beijing 1000871, China.
authors: Wen-Xin
authors: WX
authors: Hu
authors: Beijing Key Laboratory of Diagnostic and Traceability Technologies for Food Poisoning, Beijing Center for Disease Prevention and Control, 100013, China.
authors: Jing
authors: J
authors: Zhang
authors: Beijing Advanced Innovation Center for Food Nutrition and Human Health, China Agricultural University, Beijing 100193, China; College of Public Health, Capital Medical University, Beijing 100069, China; Beijing Key Laboratory of Diagnostic and Traceability Technologies for Food Poisoning, Beijing Center for Disease Prevention and Control, 100013, China. Electronic address: shaobingch@sina.com.
authors: Bing
authors: B
authors: Shao
mesh_terms: D002713:Chlorine / Q000737:chemistry; D004203:Disinfection; D054879:Halogenation; D013058:Mass Spectrometry; D047495:PPAR gamma
chemical_list: D047495:PPAR gamma; D002713:Chlorine
keywords: Bisphenol F; Chlorination; Estrogenic effect; Peroxisome proliferator-activated receptor gamma (PPAR-γ) effect; Transformation byproducts