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Bisphenol analogues (BPs) including bisphenol a (BPA) have been broadly utilized as industrial feedstocks and unavoidably discharged into water bodies. However, there is little published data on the occurrence, distribution, and environmental risks of other BPs in surface water. In this study, ten BPs besides BPA were analyzed in surface water from the Pearl River, South China. Among these detected BPs, BPA, bisphenol F (BPF), bisphenol AF (BPAF), and bisphenol S (BPS) were the most frequently detected compounds. The median concentrations of the measured BPs were ranked in the order of BPA (34.9 ng/L) > BPS (24.8 ng/L) > BPAF (10.1 ng/L) > bisphenol F (BPF) (9.0 ng/L) > bisphenol B (BPB) (7.6 ng/L) > bisphenol C (BPC) (1.2 ng/L). Among them, BPA and BPS were predominant BPs, contributing 68% of the total ten BPs in surface water of the Pearl River. These results demonstrated that BPA and BPS were the most extensively utilized and manufactured BPs in this region. The source analysis of BPs suggested that the BPs may be originated from domestic wastewater, wastewater treatment plant (WWTP) effluent, and the leaching of microplastic in surface water of the Pearl River. The calculated BP-derived estrogenic activity exhibited low to medium risks in surface water, but their combined estrogenic effects with other endocrine disrupting compounds should not be ignored.

This study investigated concentration levels of ten bisphenols (BPs) in 13 Chinese commercial fresh low temperature dairy milk samples (fresh milk) of main local and national brands with or without enzyme hydrolysis. The results showed that at least two BPs were detected in each fresh milk sample without enzyme hydrolysis and the respective mean concentrations of bisphenol AF (BPAF), bisphenol B (BPB), bisphenol C (BPC), bisphenol F (BPF), bisphenol A (BPA), bisphenol S (BPS), bisphenol AP (BPAP), bisphenol PP (BPP), bisphenol Z (BPZ), and bisphenol E (BPE) were 0.73, 0.61, 1.86, 0.87, 0.42, 0.11, 1.06, 1.42, 1.5, and 0.04 ng/mL, while their respective detection frequencies ranged from 23.1–92.3%. These results indicated the frequent detection of BPs in fresh milk samples. With enzyme hydrolysis, the respective mean concentrations of BPAF, BPA, BPB, BPC, BPF, BPS, and BPAP were increased 7.1–107.1%, indicating the long-ignored importance of enzyme hydrolysis. The respective average estimated daily intakes (EDIs) of BPA by adult and children in China via fresh milk were 32.5 and 37.5 ng/kg bw/d, indicating that BPA in fresh milk was a crucial source to human. Six out of nine other BPs had higher average EDIs than that of BPA, among which the EDI of BPAP was almost three times that of BPA, suggesting the widespread contamination of other BPs in Chinese fresh milk.

Bisphenols as an important industrial raw material has endocrine disruption, reproductive toxicity, and neurotoxicity. Laccase (Lac) has demonstrated excellent catalytic oxidation performance for phenolic compounds. Micro-nano bubbles (MNB) have been extensively used in wastewater treatment, and the high efficiency of MNB-assisted laccase (MNB-Lac) as a hybrid technique for removing bisphenols from water has been established. In this study, MNB-Lac system was used to degrade bisphenols including bisphenol A (BPA), bisphenol B (BPB), bisphenol C (BPC), bisphenol E (BPE), and bisphenol F (BPF). A comparative analysis was conducted to evaluate the degradation of individual and mixed bisphenols by MNB-Lac. The results indicated that the degradation effect on all individual bisphenols was superior. Notably, BPC consistently demonstrated higher selectivity in the mixed degradation process. In the mixed bisphenol degradation process, a distinct degradation sequence between BPE and BPF was observed. The affinity order of BPA and BPE was found to be inconsistent with their individual degradation order, and the degradation reaction was found to conform to second-order kinetics. By gas chromatography mass spectrometry detection, it was found that the degraded products of BPA, BPB, BPC, BPE, and BPF were ring and chain compounds, and the degradation pathways of the five substances were also maintenance ring structure and direct ring opening. The possible transformation relationship of mixed bisphenols during degradation by MNB-Lac was proposed. Moreover, the industrial application of MNB-Lac was evaluated by increasing the wastewater volume of BPA. Graphical Abstract

The aim of this research was to study the combined effects of bisphenols and iodine exposure on the thyroid gland during pregnancy. We included 162 pregnant women from a cohort established in Shanghai. Urinary concentrations of bisphenol A, bisphenol B(BPB), bisphenol C(BPC), bisphenol F, bisphenol S, and bisphenol AF(BPAF) were examined. Bayesian kernel machine regression (BKMR) and quantile g-computation models were used. The geometric means of BPA, BPB, BPC, BPF, BPS, BPAF, and ΣBPs levels in urine were 3.03, 0.24, 2.66, 0.36, 0.26, 0.72, and 7.55 μg/g creatinine, respectively. We observed a positive trend in the cumulative effects of BPs and iodine on serum triiodothyronine (FT3) and free thyroxine (FT4), as well as a U-shaped dose–response relationship between BPs and the probability of occurrence of thyroperoxidase autoantibody positivity in women with low urinary iodine concentration. In addition, a synergistic effect on the probability of occurrence of thyroid autoantibody positivity was observed between BPF and BPB, as well as between BPC and BPAF in this study. There were adverse health effects on the thyroid after co-exposure to BPs and iodine. Even if pregnant women were exposed to lower levels of BPs, women with iodine deficiency remained vulnerable to thyroid autoimmune disease.

Bisphenol A (BPA) is an emerging organic compound used in the production of epoxy resin, polycarbonate plastics and thermal paper. Following the restrictions on the use of bisphenol A, many substitutes have been produced as its replacement in several consumer products. The main task of this research was to examine the toxic effects of single bisphenol analogues and their mixtures against freshwater microalgae Chlorella vulgaris and Desmodesmus armatus . The findings suggest that bisphenol B, bisphenol C, bisphenol PH (EC 50 (14 day): 33.32-43.32 mg L -1 ) and bisphenol B, bisphenol C, bisphenol FL, bisphenol PH (EC 50 (14 day): 30.49-64.54 mg L -1 ) show strong toxic effects towards C. vulgaris and D. armatus , respectively. In turn, the research results indicate that the toxicity of a mixture of examined bisphenol analogs on both species of green algae is much higher (EC 50 (14 day): 24.55-32.68 mg L -1 ) than the individual toxicity of each component of the mixture. Therefore, it can be concluded that mixtures lead to the occurrence of synergistic effects. The toxicity of the individual bisphenol analogues and their mixture by EC 50 (14 day) values in descending order, was as follows: mixture>bisphenol PH> bisphenol B> bisphenol C> bisphenol FL> bisphenol F> bisphenol E for C. vulgaris and bisphenol B> mixture> bisphenol FL> bisphenol C> bisphenol PH> bisphenol E> bisphenol F for D. armatus , respectively. Moreover, the present research expands current knowledge of the ecotoxicological risks of bisphenol analogues to aquatic organisms.

Bisphenol A (BPA)-based epoxy resins have wide applications as food-contact materials such as metal can coatings. However, negative consumer perceptions toward BPA have driven the food packaging industry to develop other alternatives. In this study, four different metal cans and their lids manufactured with different BPA-replacement food-contact coatings are subjected to migration testing in order to identify migratory chemical species from the coatings. Migration tests are conducted using food simulants and conditions of use corresponding to the intended applications and regulatory guidance from the U.S. Food and Drug Administration. Extracts are analyzed by gas chromatography mass spectrometry (GC-MS) and high resolution GC-MS. The migratory compounds identified include short chain cyclic polyester migrants from polyester-based coatings and bisphenol-type migrants including tetramethyl bisphenol F (TMBPF), tetramethyl bisphenol F diglycidyl ether (TMBPF DGE), bisphenol F (BPF), bisphenol C (BPC), and other related monomers or oligomers. The concentration of the migrants is estimated using an internal standard, and validated trimethylsilyl (TMS) derivatization GC-MS methods are developed to specifically quantify TMBPF, BPF, BPC, and BPA in the coatings. The results will aid the safety evaluation of new food-contact material coating technology based on TMBPF chemistry and will provide an important reference for the industry in identifying and quantifying non-BPA coating-borne migrants.

Huge numbers of chemicals are released uncontrolled into the environment and some of these chemicals induce unwanted biological effects, both on wildlife and humans. One class of these chemicals are endocrine-disrupting chemicals (EDCs), which are released even though EDCs can affect not only the functions of steroid hormones but also of various signaling molecules, including any ligand-mediated signal transduction pathways. Dichlorodiphenyltrichloroethane (DDT), a pesticide that is already banned, is one of the best-publicized EDCs and its metabolites have been considered to cause adverse effects on wildlife, even though the exact molecular mechanisms of the abnormalities it causes still remain obscure. Recently, an industrial raw material, bisphenol A (BPA), has attracted worldwide attention as an EDC because it induces developmental abnormalities even at low-dose exposures. DDT and BPA derivatives have structural similarities in their chemical features. In this short review, unclear points on the molecular mechanisms of adverse effects of DDT found on alligators are summarized from data in the literature, and recent experimental and molecular research on BPA derivatives is investigated to introduce novel perspectives on BPA derivatives. Especially, a recently developed BPA derivative, bisphenol C (BPC), is structurally similar to a DDT derivative called dichlorodiphenyldichloroethylene (DDE).

Rèsumè Contexte Le bisphénol A (BPA) est l’un des produits chimiques synthétiques les plus utilisés dans le monde. Le BPA en tant que perturbateur endocrinien affecte le système reproducteur par le biais de ses propriétés œstrogéniques et anti-androgènes. Le resvératrol (RES), en tant que polyphénol naturel et puissant antioxydant, présente des effets protecteurs contre la toxicité sur la reproduction en inhibant le stress oxydatif. Quarante-huit rats mâles ont été divisés en huit groupes (n = 6), comprenant les groupes TÉMOIN, HUILE D’OLIVE (0,5 ml/jour), méthylcellulose Carboxyle (MCC) (1 ml de 10 g/L), RES (100 mg/kg/ jour), faible dose de 25 de BPA (25 mg/kg/jour), dose élevée de BPA (50 mg/kg/jour), faible dose de BPA + RES et dose élevée de BPA + RES. Tous les traitements ont été effectués quotidiennement par voie orale pendant 56 jours. À la fin de la 8ème semaine, des échantillons de sang ont été prélevés pour dosages hormonaux. Ensuite, les paramètres du sperme ont été analysés et le testicule gauche a été retiré pour une étude stéréologique. Résultats Nous avons montré une diminution significative des paramètres spermatiques dans les groupes traités par doses faibles et doses élevées de BPA par rapport aux groupe témoin (P<0,05). Le volume des composants testiculaires ainsi que le diamètre et la longueur des tubules séminifères ont été considérablement réduits (11-64 %) ; le nombre total des types de cellules testiculaires a diminué (34-67 %) en moyenne dans les groupes traités par doses faibles et doses élevées de BPA. De plus, la concentration sérique d’hormone folliculostimulante (FSH), lutéinisante (LH) et de testostérone a montré une réduction significative dans les groupes traités quelle que soit la dose de BPA (P<0,01). Néanmoins, le traitement par RES pourrait améliorer tous les changements mentionnés ci-dessus dans les groupes traités par doses faibles et élevées de BPA (P<0,05). Conclusions Le RES pourrait avoir un effet positif sur les changements structurels testiculaires induits par le BPA, ainsi que la qualité du sperme, en améliorant les taux sériques d’hormones gonadotrophines et de testostérone. Mots-clés Bisphénol A Resvératrol Toxicité testiculaire Paramètres du Sperme Stéréologie

Bisphenol-C epoxy cinnamate (ECC) resin was synthesized by reacting 8.09 g epoxy resin of bisphenol-C, and 3.70 g cinnamic acid using 25 ml 1,4-dioxane as a solvent, and 1 ml triethylamine as a catalyst at reflux temperature for 1–6 h. Solid epoxy cinnamate is found to have excellent solubility in common organic solvents, 10.4–4.1 mg KOHg −1 acid values, and 303.0–426.0 mg KOH g −1 hydroxyl values. FTIR and 1 HNMR spectral data supported the structure of ECC. Thermal polymerization of ECC followed by decomposition is supported by DSC exothermic (142.9 ° °C) and broad endothermic (300 ° °C) transitions. ECC followed three steps of degradation kinetics. The first step followed first-order (1.13) degradation kinetics, while the second (2.40) and the third (0.58) steps followed fractional-order degradation kinetics. The energy of activation for the second and third steps is more than 3 times that of the first step. The entropy change (Δ S *) for the first (− 176.3JK −1  mol −1 ) and third (− 84 JK −1  mol −1 ) steps are found large and negative, while it is positive for the second step (9.4 JK −1  mol −1 ). Jute-, Glass- and Jute-biomass-ECCS composites showed moderate to fairly good tensile strength, flexural strength, electric strength, and fairly good volume resistivity. J-ECCS and G-ECCS composites showed high water absorption tendency and excellent hydrolytic stability against water, 10% aq. HCl and 10% aq. NaCl and even in boiling water. The composites may be useful during natural calamities and under diverse environmental conditions.