Are structural analogues to bisphenol A a safe alternative?

Rosenmai, Anna Kjerstine; Dybdahl, Marianne; Pedersen, Gitte Alsing; Pedersen, Mikael; Vugt-Lussenburg, Barbara van; Taxvig, Camilla; Vinggard, Anne Marie

doi:10.1016/j.toxlet.2013.05.282

Cited by 4 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The US EPA identified 19 substances that could potentially be used in thermal paper as BPA substitutes through stakeholder involvement and based on their physical and chemical properties and commercial use (US EPA, 2014). Another study identified five phenolic alternatives to BPA based on their chemical structure (Rosenmai et al, 2013). Only bisphenol S (BPS; 4,4 0 -sulfonyldiphenol) and bisphenol F (BPF, Bis(4-hydroxyphenyl)methane) were identified as alternatives in both studies.…”

Section: Introductionmentioning

confidence: 99%

Bisphenol A and its structural analogues in household waste paper

et al. 2015

View full text Add to dashboard Cite

Bisphenol A (BPA) is an industrial chemical produced in large volumes. Its main use is associated with polycarbonate plastic, epoxy resins and thermal paper. In contrast to other applications, thermal paper contains BPA in its un-reacted form as an additive, which is subjected to migration. Receiving a significant amount of attention from the scientific community and beyond, due to its controversial endocrine-disrupting effects, the industry is attempting to substitute BPA in variety of applications. Alternative phenolic compounds have been proposed for use in thermal paper; however, information to what extent BPA alternatives have been used in paper is sparse. The aim of the present work was to quantify BPA and its alternatives (bisphenol S (BPS), bisphenol E (BPE), bisphenol B (BPB), 4-cumylphenol (HPP) and bisphenol F (BPF)) in waste paper and board from Danish households, thermal paper receipts, non-carbon copy paper and conventional printer paper. BPA was found in all waste paper samples analysed, while BPS was identified in 73% of them. Only BPB was not identified in any of the samples. BPA and BPS were found in the majority of the receipts, which contained no measurable concentrations of the remaining alternatives. Although receipts showed the highest concentrations of BPA and BPS, office paper, flyers and corrugated boxes, together with receipts, represented the major flux of the two compounds in waste paper streams.

show abstract

Section: Introductionmentioning

confidence: 99%

Bisphenol A and its structural analogues in household waste paper

et al. 2015

View full text Add to dashboard Cite

show abstract

“…A paper on the safety of five BPA alternatives was recently published 21 during the preparation of this manuscript. For the four out of their five BPA alternatives cited by Rosenmai, we had extracted similar experimental estrogenic activity data from EADB in the course of our work.…”

Section: ■ Discussionmentioning

confidence: 99%

Estrogenic Activity Data Extraction and in Silico Prediction Show the Endocrine Disruption Potential of Bisphenol A Replacement Compounds

Shu

Luo

et al. 2015

Chem. Res. Toxicol.

View full text Add to dashboard Cite

Bisphenol A (BPA) replacement compounds are released to the environment and cause widespread human exposure. However, a lack of thorough safety evaluations on the BPA replacement compounds has raised public concerns. We assessed the endocrine disruption potential of BPA replacement compounds in the market to assist their safety evaluations. A literature search was conducted to ascertain the BPA replacement compounds in use. Available experimental estrogenic activity data of these compounds were extracted from the Estrogenic Activity Database (EADB) to assess their estrogenic potential. An in silico model was developed to predict the estrogenic activity of compounds lacking experimental data. Molecular dynamics (MD) simulations were performed to understand the mechanisms by which the estrogenic compounds bind to and activate the estrogen receptor (ER). Forty-five BPA replacement compounds were identified in the literature. Seven were more estrogenic and five less estrogenic than BPA, while six were nonestrogenic in EADB. A two-tier in silico model was developed based on molecular docking to predict the estrogenic activity of the 27 compounds lacking data. Eleven were predicted as ER binders and 16 as nonbinders. MD simulations revealed hydrophobic contacts and hydrogen bonds as the main interactions between ER and the estrogenic compounds.

show abstract

“…Because of the similarity in the structure, these analogues are suspected to have similar toxic effects. , It has been reported that BPB, BPF, BPS, and bisphenol AF (BPAF) exhibit estrogenic or anti-androgenic activities similar to or even greater than those of BPA. − Bisphenol FL (BPFL) has been suggested to have anti-estrogenic effects in vitro and cause adverse effects on uterotrophic activity in mice, even at doses lower than the NOAEL (5 mg/kg bw/day) reported for BPA . Moreover, the chlorinated derivatives exhibited a higher estrogenic activity and a greater capability to activate peroxisome proliferator-activated receptor γ (PPAR-γ) than BPs. , …”

Section: Introductionmentioning

confidence: 99%

Bisphenol Analogues and Their Chlorinated Derivatives in Breast Milk in China: Occurrence and Exposure Assessment

Niu

Wang

Yang

et al. 2021

J. Agric. Food Chem.

View full text Add to dashboard Cite

Concentrations of bisphenol A (BPA) and its analogues (together with their chlorinated derivatives are referred to as BPs) were measured in 181 breastmilk samples collected from 9 provinces in China in 2014. Twelve BP types were found. The BP concentrations ranged from not detected to 5.912 μg/L. BPA was the predominant BP, followed by bisphenol F (BPF) and bisphenol S (BPS). The mean BPA, BPF, and BPS levels were 0.444, 0.107, and 0.027 μg/L, respectively. Other BPs were sporadically detected in breastmilk samples. There were no differences (p > 0.05) in BPA, BPF, BPS, or total BP levels in the urban and rural regions or the northern and southern regions. BPA accounted for approximately 70% of the BPs and BPF accounted for more than 20% of the BPs in breast milk samples. The high contribution of BPF indicated that BPA analogues, not only BPA, should receive attention. The upper-bound daily intakes of BPs for infants 0–6 months old were 0.044–1.291 μg/kg bw/day. Despite the absence of tolerable daily intake data, attention should be paid not only on BPA but also BPF.

show abstract

Are structural analogues to bisphenol A a safe alternative?

Cited by 4 publications

References 0 publications

Bisphenol A and its structural analogues in household waste paper

Bisphenol A and its structural analogues in household waste paper

Estrogenic Activity Data Extraction and in Silico Prediction Show the Endocrine Disruption Potential of Bisphenol A Replacement Compounds

Bisphenol Analogues and Their Chlorinated Derivatives in Breast Milk in China: Occurrence and Exposure Assessment

Contact Info

Product

Resources

About