|Molar mass||250.27 g·mol−1|
|Appearance||White colorless solid; forms needle shaped crystals in water|
|Melting point||245 to 250 °C (473 to 482 °F; 518 to 523 K)|
|Solubility||soluble in ethanol|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Bisphenol S (BPS) is an organic compound with the formula (HOC6H4)2SO2. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used in curing fast-drying epoxy resin adhesives. It is a bisphenol, and a close analog of bisphenol A (BPA) in which the dimethylmethylene group (C(CH3)2) is replaced with a sulfone group (SO2).
BPS has become increasingly common as a plasticizing agent following the widespread bans on the use of BPA due to its estrogen-mimicking properties, and BPS can now be found in a variety of common consumer products. In some cases, BPS is used where the legal prohibition on BPA allows products containing BPS to be labelled "BPA free". BPS also has the advantage of being more stable to heat and light than BPA.
To comply with restrictions and regulations on BPA due to its confirmed toxicity, manufacturers are gradually replacing BPA with other related compounds, mainly bisphenol S (BPS; 4,4′-sulfonyldiphenol), as substitutes in industrial applications.
BPS is also used as an anticorrosive agent in epoxy glues. Chemically, BPS is being used as a reagent in polymer reactions. BPS has also been reported to occur in canned foodstuffs, such as tin cans.
In a recent study analyzing BPS in a variety of paper products worldwide, BPS was found in 100% of tickets, mailing envelopes, airplane boarding passes, and airplane luggage tags. In this study, very high concentrations of BPS were detected in thermal receipt samples collected from cities in the United States, Japan, Korea, and Vietnam. The BPS concentrations were large but varied greatly, from a few tens of nanograms per gram to several milligrams per gram. Finally, BPS can get into the human body through dermal absorption from handling banknotes.
Health and safety
Recent work suggests that, like BPA, BPS also has endocrine disrupting properties. What makes BPS, and BPA, endocrine disruptors is the presence of the alcohol group on the benzene ring. This is called a phenol ring and it allows BPA and BPS to mimic estradiol. In a study of human urine BPS was found in 78% of the samples tested. This percentage is comparable to BPA which was found in 95% of urine samples. Another study done on thermal receipt paper shows that 88% of human exposure to BPS is through receipts. In rodent studies BPS also has shown influenced uterine growth which indicates activation of estradiol.
BPS has been shown to have similar in vitro estrogenic activity to BPA and acts as a xenoestrogen. One study showed that exposure to low levels of BPS in cultured rat pituitary cells altered the estrogen estradiol signaling pathway to induce inappropriate release of prolactin, which, as a result, affected cell proliferation and apoptosis.
BPS has also been linked to changes in neurodevelopment. In a 2014 study performed by researchers at the University of Calgary, exposure to low levels of BPS disrupted the timing of neurogenesis within the hypothalamus in embryonic zebrafish. The rate at which neurons developed increased by 240 percent.
BPS is more resistant to environmental degradation than BPA.
BPS was first made in 1869 as a dye  and is currently common in everyday consumer products. BPS is an analog of BPA that has replaced BPA in a variety of ways, being present in thermal receipt paper, plastics, and indoor dust. After health concerns associated with bisphenol A grew in 2012, BPS began to be used as a replacement.
It is difficult for consumers to determine if a product contains BPS due to limited labeling regulations.
- 2 C6H5OH + H2SO4 → (C6H4OH)2SO2 + 2 H2O
- 2 C6H5OH + SO3 → (C6H4OH)2SO2 + H2O
- Liao, C.; Liu, F.; Kannan, K. (2012). "Bisphenol S, a New Bisphenol Analogue, in Paper Products and Currency Bills and Its Association with Bisphenol a Residues". Environmental Science & Technology 46 (12): 6515–22. doi:10.1021/es300876n. PMID 22591511.
- Liao, C.; Liu, F.; Guo, Y.; Moon, H. B.; Nakata, H.; Wu, Q.; Kannan, K. (2012). "Occurrence of Eight Bisphenol Analogues in Indoor Dust from the United States and Several Asian Countries: Implications for Human Exposure". Environmental Science & Technology 46 (16): 9138–9145. doi:10.1021/es302004w.
- Jenna Bilbrey (Aug 11, 2014). "BPA-Free Plastic Containers May Be Just as Hazardous". Scientific American.
- Kuruto-Niwa, R.; Nozawa, R.; Miyakoshi, T.; Shiozawa, T.; Terao, Y. (2005). "Estrogenic activity of alkylphenols, bisphenol S, and their chlorinated derivatives using a GFP expression system". Environmental Toxicology and Pharmacology 19 (1): 121–130. doi:10.1016/j.etap.2004.05.009. PMID 21783468.
- Chen, M. Y.; Ike, M.; Fujita, M. Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols. Environ. Toxicol. 2002, 17 (1), 80−86.
- (Viñas, P.; Campillo, N.; Martínez-Castillo, N.; Hernandez- ́ Cordoba, M. Comparison of two derivatization-based methods for ́ solid-phase microextraction-gas chromatography-mass spectrometric determination of bisphenol A, bisphenol S and biphenol migrated from food cans. Anal. Bioanal. Chem. 2010, 397 (1), 115−125.)
- Liao, Chunyang; Liu, Fang; Kannan, Kurunthachalam (2012). "Bisphenol S, a new bisphenol analogue, in paper products and currency bills and its association with bisphenol A residues". Environmental science & technology 46 (12): 6515–6522. Bibcode:2012EnST...46.6515L. doi:10.1021/es300876n.
- Manjumol Mathew, S. Sreedhanya, P. Manoj, C.T. Aravindakumar, and Usha K. Aravind (2014). "Exploring the interaction of Bisphenol-S with Serum Albumins: A Better or Worse Alternative for Bisphenol A?". The journal of physical chemistry 118 (14): 3832–3843. doi:10.1021/jp500404u. PMID 24635450.
- Johanna R. Rochester and Ashely L. Bolden (2015). "Bisphenol S and F: A Systematic Review and Comparison of the Hormonal Activity of Bisphenol A Substitutes". Environmental Health Perspectives: 1–33. doi:10.1289/ehp.1408989.
- Viñas, R.; Watson, C. S. (2013). "Bisphenol S Disrupts Estradiol-Induced Nongenomic Signaling in a Rat Pituitary Cell Line: Effects on Cell Functions". Environmental Health Perspectives 121 (3): 352–8. doi:10.1289/ehp.1205826. PMID 23458715.
- Ji, K.; Hong, S.; Kho, Y.; Choi, K. (2013). "Effects of Bisphenol S Exposure on Endocrine Functions and Reproduction of Zebrafish". Environmental Science & Technology: 8793–8800. doi:10.1021/es400329t.
- Kinch, Cassandra D et al. "Low-dose exposure to bisphenol A and replacement bisphenol S induces precocious hypothalamic neurogenesis in embryonic zebrafish". PNAS. Proceedings of the National Academy of Sciences of the United States of America. PMID 25583509.
- Gehring, M.; Tennhardt, L.; Vogel, D.; Weltin, D.; Bilitewski, B. Bisphenol A Contamination of Wastepaper, Cellulose and Recycled Paper Products. In Waste Management and the Environment II. WIT Transactions on Ecology and the Environment; Brebbia, C. A., Kungulos, S., Popov, V., Itoh, H., Eds.; WIT Press: Southampton, Boston, 2004; Vol. 78, pp 294−300.
- European Commission-Joint Research Centre. European Union Risk Assessment Report, 4,4′-Isopropylidenediphenol (Bisphenol-A). 2008, available from http://ecb.jrc.ec.europa.eu/documents/ExistingChemicals/RISK_ASSESSMENT/ADDENDUM/bisphenola_add_ 325.pdf
- Ike, M.; Chen, M. Y.; Danzl, E.; Sei, K.; Fujita, M. Biodegradation of a variety of bisphenols under aerobic and anaerobic conditions. Water Sci. Technol. 2006, 53 (6), 153−159.
- Glausiusz, Josie. "Toxicology: The plastics puzzle". Nature Publishing Group. Retrieved 25 March 2015.
- Liao, C; Liu, F; Alomirah, H; Loi, V. D.; Mohd, M. A.; Moon, H. B.; Nakata, H; Kannan, K (2012). "Bisphenol S in urine from the United States and seven Asian countries: Occurrence and human exposures". Environmental Science & Technology 46 (12): 6860–6. Bibcode:2012EnST...46.6860L. doi:10.1021/es301334j. PMID 22620267.
- Howard, Brian. "Chemical in BPA-Free Products Linked to Irregular Heartbeats". National Geographic. National Geographic. Retrieved 29 March 2015.
- METHOD OF PREPARATION OF 4,4′-DIHYDROXYDIPHENYLSULPHONE (Freepatentsonline).