1-1-bis(4-hydroxyphenyl)cyclohexane and bis(4-hydroxyphenyl)sulfone

In recent years, the reproductive toxicity of new bisphenol analogs has garnered much interest, but it remains to be determined whether bisphenol analogs affect polycystic ovarian syndrome (PCOS).. This study utilized data from a multicenter hospital-based case-control study conducted in 2014-2016 to examine the association between endocrine-disrupting chemicals and infertility in China. 321 PCOS cases and 412 controls were included in the current analysis. We quantified seven bisphenol analogs in urine samples, including bisphenol A (BPA), bisphenol AP (BPAP), bisphenol AF (BPAF), bisphenol B (BPB), bisphenol S (BPS), bisphenol P (BPP), and bisphenol Z (BPZ). Spearman correlation and generalized linear regression were used in assessing the relationship between bisphenol analogs and hormonal parameters. To examine the association of bisphenol analogs with odds of PCOS, multiple logistic regression, and two multi-pollutant models [quantile-based g-computation (QGC) and extreme gradient boosting (XGBoost) methods] were used.. After covariates adjustment, BPA, BPS, and BPAF were positively correlated with testosterone (T) in the control group (P < 0.05). Dose-response relationships were discovered between BPA, BPS, BPZ, and BPAF quartiles and PCOS. Mixed exposure to seven bisphenol analogs was found to be positively associated with the odds of PCOS (adjusted odds ratio = 1.26; 1.12-1.45), which was primarily driven by BPS (weight = 0.51), BPZ (weight = 0.26), and BPAF (weight = 0.23). Women who were overweight or obese tended to have a stronger association between bisphenol analogs and PCOS than normal-weight women.. Environmental exposure to bisphenol analogs was associated with increased odds of PCOS in this case-control study. This association was stronger among obese and overweight women.

Topics: Benzhydryl Compounds; Case-Control Studies; Female; Humans; Obesity; Overweight; Polycystic Ovary Syndrome

Bisphenol analogues (BPs) and natural estrogens (NEs) as two important groups of endocrine-disrupting compounds (EDCs) in drinking water treatment plants (DWTPs) have been hardly investigated except bisphenol A (BPA) and three major NEs including estrone (E1), 17β-estradiol (E2) and estriol (E3). In this study, a GC-MS analytical method was firstly established and validated for trace simultaneous determination of ten BPs and twelve NEs in drinking water, which included BPA, bisphenol B (BPB), bisphenol C (BPC), bisphenol E (BPE), bsiphenol F (BPF), bsiphenol P (BPP), bisphenol S (BPS), bisphenol Z (BPZ), bisphenol AF (BPAF), bisphenol AP (BPAP), E1, E2, E3, 17α-estradiol (17α-E2), 2-hydroestrone (2OHE1), 16hydroxyestrone (16α-OHE1), 4-hydroestrone (4OHE1), 2-hydroxyesstradiol (2OHE2), 4-hydroxyestradiol (4OHE2), 17-epiestriol (17epiE3), 16-epiestriol (16epiE3) and 16keto-estraiol (16ketoE2). This investigation showed that eighteen out of twenty-two targeted compounds were detected in drinking source waters of eight DWTPs with concentrations ranging from not detected to 142.8 ng/L. Although the conventional treatment process of DWTP could efficiently remove both BPs and NEs with respective removal efficiencies of 74.1%-90.9% and 74.5%-100%, BPA, BPS, BPE, BPZ, E1, 2OHE1, and 2OHE2 were found in the finished drinking waters. Chlorination could remove part of BPs and NEs, but the efficiency varied greatly with DWTP and the reason was unknown. In the finished drinking waters of eight DWTPs, the highest chemically calculated estrogen equivalence (EEQ) derived from BPs and NEs was up to 6.11 ngE2/L, which was over 22 times that could do harm to zebrafish, indicating a potential risk to human health. Given the fact that many chlorination products of BPs and NEs likely have higher estrogenic activities, the estrogenic effect of BPs and NEs in finished drinking water should be accurately examined urgently with the inclusion of BPs, NEs as well as their main chlorinated by-products. This study shed new light on the occurrence, removal, and potential estrogenic effects of BPs and NEs in DWTPs.

Topics: Animals; Benzhydryl Compounds; Drinking Water; Estradiol; Estriol; Estrogens; Estrone; Humans; Water Purification; Zebrafish

Bisphenol A (BPA) exposure has been linked to adverse childhood neurodevelopment, but little is known about whether BPA substitutes exposures are also related to childhood neurodevelopment.. To investigate the associations of exposure to BPA and its substitutes with infant neurodevelopment at 12 months.. A total of 420 infants at 12 months were included from the Laizhou Wan (Bay) Birth Cohort in Shandong, China. Urinary concentrations of BPA and its substitutes including bisphenol S (BPS), bisphenol B (BPB), bisphenol AF (BPAF), bisphenol AP (BPAP), bisphenol P (BPP) and bisphenol Z (BPZ) were measured. Developmental quotient (DQ) scores based on the Gesell Development Schedules (GDS) were used to evaluate infant neurodevelopment. The multivariable linear regression and weighted quantile sum (WQS) regression were applied to estimate the associations of exposure to individual bisphenols and their mixtures with DQ scores, respectively. Sex-stratified analyses were also performed.. BPA was detected in most infants (89.05%) and had the highest median concentration (0.709 ng/mL) among all bisphenols. BPA substitutes except BPZ were ubiquitous in infants' urine samples (>70%), and BPS showed the highest median concentration (0.064 ng/mL) followed by BPAP (0.036 ng/mL), BPAF (0.028 ng/mL), BPP (0.015 ng/mL) and BPB (0.013 ng/mL). In multivariable linear regression, only BPAF exposure was inversely associated with social DQ scores among all infants (β = -0.334; 95% CI: -0.650, -0.019). After sex stratification, this inverse association was significant in girls (β = -0.605; 95% CI: -1.030, -0.180). Besides, BPA exposure was negatively related to gross motor DQ scores in boys (β = -1.061; 95% CI: -2.078, -0.045). WQS analyses confirmed these results.. Our study suggests that bisphenol exposure during infancy may be associated with poor infant neurodevelopment, and BPAF as a commonly used BPA substitute contributing the most to this adverse association deserves more attention.

Topics: Benzhydryl Compounds; Child; Cross-Sectional Studies; Female; Humans; Infant; Male; Phenols

Bisphenol Z (BPZ), bisphenol S (BPS), bisphenol C (BPC), and bisphenol F (BPF) had been widely used as alternatives to bisphenol A (BPA), but the toxicity data of these bisphenol analogues were very limited. In this study, the joint toxicity of BPZ, BPS, BPC, and BPF to zebrafish (

Topics: Animals; Benzhydryl Compounds; Cyclohexanes; Phenols; Sulfones; Zebrafish; Zebrafish Proteins

Topics: Benzhydryl Compounds; China; Cyclohexanes; Environmental Monitoring; Phenols; Rivers; Sulfones; Water; Water Pollutants, Chemical

Several structural analogues of bisphenol A (BPA), e.g., bisphenol F (BPF), bisphenol S (BPS), and bisphenol Z (BPZ), have been used as its substitutes in many applications and consequently detected in the environment, and human specimen such as urine and serum. While BPA has been frequently reported for thyroid hormone disruption in both experimental and epidemiological studies, less is known for the BPA analogues. In the present study, thyroid hormone disrupting effects of BPF, BPS and BPZ, were investigated, and compared with those of BPA, using embryo-larval zebrafish (Danio rerio). At 120 hpf, significant increases in T3 and/or T4 were observed in the larval fish following exposure to BPA, BPF, or BPS. Moreover, transcriptional changes of the genes related to thyroid development (hhex and tg), thyroid hormone transport (ttr) and metabolism (ugt1ab) were observed as well. Thyroid hormone (T4) disruption by BPF was observed even at the concentration (2.0 mg/L) lower than the effective concentration determined for BPA (>2.0 mg/L). Delayed hatching was observed by all tested bisphenols. Our results clearly show that these BPA analogues can disrupt thyroid function of the larval fish, and their thyroid hormone disruption potencies could be even greater than that of BPA. The concentrations which disrupt thyroid function of the larval fish were orders of magnitude higher than those occurring in the ambient environment. However, thyroid hormone disruption by longer term exposure and its consequences in the fish population, deserve further investigation.

Topics: Animals; Benzhydryl Compounds; Cyclohexanes; Endocrine Disruptors; Humans; Larva; Phenols; Sulfones; Thyroid Hormones; Thyroxine; Triiodothyronine; Zebrafish

Topics: Animals; Benzhydryl Compounds; Chromatography, High Pressure Liquid; Cyclohexanes; Geologic Sediments; Humans; Male; Microwaves; Phenols; Rats, Sprague-Dawley; Solid Phase Extraction; Solvents; Sulfones; Tandem Mass Spectrometry; Ultrasonics

In the present study, a method has been efficiently developed for the first time to determine nine bisphenol analogues [bisphenol A (BPA), bisphenol C (BPC), bisphenol AF (BPAF), bisphenol E (BPE), bisphenol F (BPF), bisphenol G (BPG), bisphenol M (BPM), bisphenol S (BPS), and bisphenol Z (BPZ)] together in bottled carbonated beverages (collected from the local market of Lucknow, India) using dispersive liquid-liquid microextraction process. This is based on solidification of floating organic droplet (DLLME-SFO) followed by injector port silylation coupled with gas chromatography-tandem mass spectrometry. The process investigated parameters of DLLME-SFO (including the type of extraction and disperser solvents with their volumes, effect of pH, ionic strength, and the sample volume), factors influencing to injection port derivatization like, collision energy, injector port temperature, derivatizing reagent with sample injection volume, and type of organic solvent. BPA, BPF, BPZ, and BPS were detected in each sample; whereas, other bisphenols were also detected in some carbonated beverage samples. After optimizing the required conditions, good linearity of analytes was achieved in the range of 0.097-100ngmL

Topics: Benzhydryl Compounds; Carbonated Beverages; Chromatography, Gas; Cyclohexanes; Food Analysis; Limit of Detection; Liquid Phase Microextraction; Phenols; Solvents; Sulfones; Tandem Mass Spectrometry

A molecularly imprinted polymer (MIP) for selective recognition of seven bisphenols (BPs) was prepared using dummy template phenolphthalein (PP) by bulk polymerization. The characterization results of scanning electron microscopy and nitrogen adsorption-desorption measurements showed that the prepared PP-MIP possessed narrow particle diameter distribution (40-60 µm), a specific surface area (S(BET)) of 359.77 m2/g and a total pore volume (Vt) of 0.730 cm3/g. The adsorption capacity for bisphenol A (BPA) of PP-MIP was evaluated by static adsorption experiment. And the Scatchard analysis revealed that the maximum specific adsorption capacity of PP-MIP was 4.661 µmol/g. Good class selectivity for BPA and its six structural analogues of bisphenol B (BPB) , bisphenol E (BPE), bisphenol AF (BPAF), bisphenol S (BPS), bisphenol AP (BPAP) and bisphenol Z (BPZ) was demonstrated by the chromatographic evaluation experiment. The prepared PP-MIP was successfully used as solid-phase extraction (SPE) sorbent for the separation and purification of the seven BPs in human urine, bovine serum and beer samples. Meanwhile, an accurate and sensitive MIP-SPE-HPLC method was established for the determination of the seven BPs in human urine, bovine serum and beer samples. The limits of detection (LODs) for the three samples were in the range of 1.2-2.0 µg/L. The results showed that good linearities were obtained in the range of 0.02-2 mg/L for the seven BPs and the correlation coefficients (r) were higher than 0.999 8. The recoveries of the BPs spiked in blank samples at two spiked levels (100 and 500 µg/L for each BP) were in the range of 90.1%-107.1% with the RSDs ≤ 8.1%. The proposed method is simple and reliable for the rapid detection of the seven BPs in human urine, bovine serum and beer samples.

Topics: Adsorption; Animals; Beer; Benzhydryl Compounds; Cattle; Chromatography, High Pressure Liquid; Cyclohexanes; Humans; Microscopy, Electron, Scanning; Molecular Imprinting; Phenols; Polymerization; Polymers; Serum; Solid Phase Extraction; Sulfones; Urinalysis

Due to their growing consumption, ready-made meals are a major dietary component for many people in today's society, representing an important potential route of human exposure to several food contaminants. The recent restrictions in the use of bisphenol A have led the plastic industry to look for alternative chemicals, most of them belonging to the same family of p,p'-bisphenols. The aim of the current work was to develop and validate a method based on stable-isotope dilution liquid chromatography-tandem mass spectrometry for the analysis of bisphenol A and its main analogs - bisphenol S, 4,4'-sulfonylbis(2-methylphenol), bisphenol F, bisphenol E, bisphenol B, bisphenol Z, bisphenol AF, bisphenol AP, tetrabromobisphenol A and bisphenol P - in solid foodstuffs, and particularly in ready-made meals. Extraction was carried out by ultrasound-assisted extraction after sample disruption with sand. A selective solid-phase extraction procedure was then applied to reduce potential matrix interferences. Derivatization of bisphenols with pyridine-3-sulfonyl chloride increased their ionization efficiency by electrospray ionization. Validation of the proposed method was performed in terms of selectivity, matrix effects, linearity, precision, measurement uncertainty, trueness and limits of detection. Satisfactory repeatability and intermediate precision were obtained; the related relative standard deviations were ≤7.8% and ≤10%, respectively. The relative expanded uncertainty (k=2) was below 17% for all bisphenol analogs and the trueness of the method was demonstrated by spike recovery experiments. Low limits of detection, in the range from 0.025μgkg(-1) to 0.140μgkg(-1), were obtained for all compounds. To demonstrate the applicability of the proposed method, it was eventually applied to several ready-made meals purchased from different supermarkets in Belgium.

Topics: Belgium; Benzhydryl Compounds; Chromatography, Liquid; Cyclohexanes; Food Analysis; Food Contamination; Humans; Indicator Dilution Techniques; Isotopes; Phenols; Solid Phase Extraction; Spectrometry, Mass, Electrospray Ionization; Sulfones; Tandem Mass Spectrometry