Novel Biobased Furanic Diols as Potential Alternatives to BPA: Synthesis and Endocrine Activity Screening

Abstract

A series of asymmetric and symmetric diols were prepared in high yields from biomass-derived feedstocks 5-hydroxymethyl furfural (HMF) and 2,5-diformyl furan (DFF) as potential replacements for bisphenol A (BPA). The diols were screened for estrogenic, androgenic, antiandrogenic, and antithyroid activities in reporter gene assays. Several of the low molecular weight asymmetric diols did not exhibit activity in any of the assays and thus have promise as potentially more sustainable alternatives to BPA.

Terephthalic Acid Copolyesters Containing Tetramethylcyclobutanediol for High‐Performance Plastics

“…Moreover, many other substituents based on CBDO chemistry can open new doors towards industrially useful copolyesters. Renewable monomers like 2,5‐furandicarboxylic acid (2,5‐FDCA) have been used as TPA substitutes[ 62 , 63 ] but the polyethylene furandicarboxylate (PEF) has a T g of 82–89 °C. [64] Therefore, copolymerizing TMCD with FDCA and EG may give a partially renewable copolyester with higher T g than PEF.…”

Bio-Based Furanic Di(meth)acrylates as Reactive Diluents for UV Curable Coatings: Synthesis and Coating Evaluation

“…Four asymmetric and five symmetric diols were prepared from biomass-derived feedstock HMF and 2,5-diformyl furan according to a previously published procedure . The furan-based diols tended to slowly degrade and were immediately used to prepare diluents when they were synthesized.…”

“…It was purified before use. 2,5-Bishydromethyl furan and the symmetric and asymmetric furan-based diols were synthesized by following previously reported procedures . Unless otherwise stated, all commercially procured reagents were used as received without further purification.…”

“…Recently, our group has synthesized a series of asymmetric and symmetric diols derived from HMF in high yields using an operationally simple protocol . Several of these diols were found to exhibit no endocrine activity in several assays.…”

Estrogenic activity of lignin-derivable alternatives to bisphenol A assessed via molecular docking simulations

“…5,[7][8][9] BPA also is a suspected endocrine disruptor compound because it can mimic the natural estrogen hormone 17b-estradiol (E2) by binding to estrogen receptor alpha (ERa). 5,6,[9][10][11][12][13] The disruption of the endocrine system can lead to severe human health impacts, including diabetes, 14 obesity, 15 cardiovascular diseases, 16 reproductive disorders, 17 and cancer. 2,18 Therefore, several countries have restricted or eliminated BPA use in food contact applications.…”