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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.

The possibility of removing bisphenol A and its five potential substitutes (bisphenols S, F, AF, E, and B) was tested using microorganism consortia from river water and activated sludge from municipal and rural wastewater treatment plants. For most bisphenols, biodegradation with activated sludge was faster than with river water and a greater extent of biodegradation was also achieved. However, only bisphenol A and bisphenol F underwent 100% primary biodegradation while other bisphenols degraded no more than about 50% which has some important implications in case of their increased usage. Metabolic activity in biodegradation liquors was also tested and it showed higher activity in the tests with activated sludge than with river water. However, there was no clear connection between the decline of metabolic activity and the extent of biodegradation as decreased activity was observed for two easily degrading bisphenols and two others with little biodegradability. It can be assumed that two different phenomena are involved in this process including depletion of nutrients for easily degradable bisphenol A and absence of nutrients for bacteria incapable of primary degradation of bisphenol AF and bisphenol S.

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

Given the widespread use of bisphenols and parabens in consumer products, the assessment of their intake is crucial and represents the first step towards the assessment of the potential risks that these compounds may pose to human health. In the present study, a total of 98 samples of food items commonly consumed by the Spanish population were collected from different national supermarkets and grocery stores for the determination of parabens and bisphenols. Our analysis demonstrated that 56 of the 98 food samples contained detectable levels of parabens with limits of quantification (LOQ) between 0.4 and 0.9 ng g−1. The total concentration of parabens (sum of four parabens: ∑parabens) ranged from below the LOQ to 281.7 ng g−1, with a mean value of 73.86 ng g−1. A total of 52% of the samples showed detectable concentrations of bisphenols. Bisphenol A (BPA) was the most frequently detected bisphenol in the food samples analysed, followed by bisphenol S (BPS) and bisphenol E (BPE). Bisphenol AF (BPAF), bisphenol B (BPB) and bisphenol P (BPP) were not found in any of the analysed samples. LOQ for these bisphenols were between 0.4 and 4.0 ng g−1.

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.

An epoxy-functionalized beta type nanozeolite (BEA)/graphene oxide nanocomposite modified glassy carbon electrode (GCE/BEA/APTMS/GA/GO/NF) has been created for the differential pulse voltammetric determination of bisphenol E (BPE). The modified electrode presented an enhanced current response in comparison with bare GCE. A linear dependence of anodic peak current ( I p ) and scan rate (ν) was observed, which showed that the electrochemical process was adsorption-controlled. Differential pulse voltammetry (DPV) was employed and optimized for the sensitive determination of BPE. Under the optimized conditions, the anodic peak current was linearly proportional to BPE concentration in the range between 0.07 and 4.81 µM, with a correlation coefficient of 0.995 and limit of detection 0.056 μM (S/N = 3). The electrode showed good repeatability and storage stability, and a low response to interfering compounds. Comparison was made to the determination of bisphenol A. To confirm the electrode analytical performance, recovery tests were performed, and deviations lower than 10% were found. The BEA zeolite-GO nanocomposite proved to be a promising sensing platform for bisphenol determination. Graphical abstract

As a class of thermosetting resins with exceptional overall performance, cyanate esters have not received sufficient attention for their potential applications in 3D printing. In this paper, polytetrafluoroethylene micropowder is used for the first time as a thixotropic agent to regulate the rheological properties of liquid bisphenol E cyanate monomer for direct ink writing of cyanate ester resins in 3D printing. Due to their appropriate compatibility, the mixed inks exhibit high storage modulus and shear-thinning behavior, enabling the printed structures to maintain their shape well during printing and subsequent curing processes. The printed samples have good mechanical strength and excellent thermal stability. At the same time, the presence of polytetrafluoroethylene endows the composite materials with low dielectric constant and hydrophobicity. The latter property leads to high hygrothermal stability of the composites. The cyanate ester-polytetrafluoroethylene composite developed here offers a reliable method for 3D printing high performance cyanate ester, efficiently enhances the processibility of the cyanate ester based materials. Graphical abstract

Bisphenol compounds (BPs) are a severe threat to humans and creatures; hence it is critical to develop a quick and simple approach for removing trace BPs from water. This research synthesized a novel template–monomer complex, phenolphthalein-(3-isocyanatopropyl)triethoxysilane (PP-ICPTES), as a dummy template, and a molecularly imprinted polymer for bisphenol was made via a semi-covalent approach. By successfully coating the imprinted layer on the Fe3O4@SiO2@mSiO2 structure, a magnetic dummy molecularly imprinted mesoporous silica nanoparticles (m-DMI-MSNPs) with a core-shell structure and superefficient aqueous phase selectivity for bisphenols was synthesized. The morphology and structure of the m-DMI-MSNPs were characterized using transmission electron microscopy (TEM), nitrogen adsorption-desorption analysis, Fourier transform infrared spectroscopy (FT-IR), and vibrating sample magnetometry (VSM). The prepared m-DMI-MSNPs presented excellent water compatibility and magnetic separation abilities. The m-DMI-MSNPs showed excellent recognition selectivity towards BPs with imprinting factors of 7.6, 8.2, and 7.5 for bisphenol F (BPF), bisphenol E (BPE), and bisphenol A (BPA), respectively. Fast binding kinetics (equilibrium time < 1 min) and a high rebinding capacity (maximum adsorption capacity, 38.75 mg g–1) were observed in the adsorption experiments. More importantly, the m-DMI-MSNPs, which combine good water compatibility, class selectivity, and magnetic separation performance, exhibited excellent performance for the removal of BPF, BPE, and BPA from tap water, mineral water, and sewage water samples, with removal efficiencies in the ranges of 96.6–97.8, 95.6–97.1, and 93.1–95.3%, respectively.

As typical environmental hormones, endocrine-disrupting chemicals (EDCs) have become a global environmental health issue of high concern due to their property of interfering with the endocrine systems of organisms. As a commonly used substitute for bisphenol A (BPA), bisphenol E (BPE) has been frequently detected in environmental matrices such as soil and water in recent years. Existing research has unveiled the developmental and reproductive toxicity of BPE; however, only one in vitro cellular experiment has preliminarily indicated potential neurotoxic risks, with its underlying mechanisms remaining largely unelucidated in the current literature. Potential toxic mechanisms and action targets of BPE were predicted using the zebrafish model via network toxicology and molecular docking, with RT-qPCRs being simultaneously applied to uncover neurotoxic effects and associated mechanisms of BPE. A significant decrease (p < 0.05) in the frequency of embryonic spontaneous movements was observed in zebrafish at exposure concentrations ≥ 0.01 mg/L. At 72 hpf and 144 hpf, the larval body length began to shorten significantly from 0.1 mg/L to 1 mg/L, respectively (p < 0.01), accompanied by a reduced neuronal fluorescence intensity and a shortened neural axon length (p < 0.01). By 144 hpf, the motor behavior in zebrafish larvae was inhibited. Through network toxicology and molecular docking, HSP90AB1 was identified as the core target, with the cGMP/PKG signaling pathway determined to be the primary route through which BPE induces neurotoxicity in zebrafish larvae. BPE induces neuronal apoptosis and disrupts neurodevelopment by inhibiting the cGMP/PKG signaling pathway, ultimately suppressing the larval motor behavior. To further validate the experimental outcomes, we measured the expression levels of genes associated with neurodevelopment (elavl3, mbp, gap43, syn2a), serotonergic synaptic signaling (5-ht1ar, 5-ht2ar), the cGMP/PKG pathway (nos3), and apoptosis (caspase-3, caspase-9). These results offer crucial theoretical underpinnings for evaluating the ecological risks of BPE and developing environmental management plans, as well as crucial evidence for a thorough comprehension of the toxic effects and mechanisms of BPE on neurodevelopment in zebrafish larvae.