Bisphenol A

Bisphenol A
Names
IUPAC name
4,4'-(propane-2,2-diyl)diphenol
Other names
BPA, p,p'-isopropylidenebisphenol,
2,2-bis(4-hydroxyphenyl)propane.
Identifiers
  • 80-05-7 checkY
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.133
EC Number
  • 201-245-8
KEGG
RTECS number
  • SL6300000
UNII
UN number 2430
  • Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
  • CC(C)(c1ccc(cc1)O)c2ccc(cc2)O
Properties
C15H16O2
Molar mass 228.29 g·mol−1
Appearance White to light brown flakes or powder
Density 1.20 g/cm³, solid
Melting point 158 to 159 °C (430 K)
Boiling point 220 °C (493 K) / 4 mmHg
120–300 ppm (at 21.5 °C)
Hazards
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Danger
H317, H318, H335, H360, H410
P201, P202, P261, P271, P272, P273, P280, P302+P352, P304+P340+P312, P305+P351+P338+P310, P308+P313, P333+P313, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0
Flash point 227 °C (441 °F; 500 K)
600 °C
Safety data sheet (SDS) Sigma-Aldrich Co., Bisphenol A.
Related compounds
Related bisphenols
 Bisphenol AF
Bisphenol S
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Bisphenol A is often used to make plastics, such as this polycarbonate water bottle.

Bisphenol A (BPA) is an organic compound. It is a bisphenol, a type of compound with two linked phenol groups. The "A" stands for acetone, which is used to link the two phenols. BPA is an important commodity chemical, with billions of tonnes made every year. It is used to make many different types of plastic, mostly polycarbonates and epoxy resins.

BPA is controversial because of links to health issues. Scientists discovered in the mid 1930s that people and animals react to BPA in the same way that they react to hormones (with oestrogen-like effects). Some stores stopped selling products made with BPA in 2008 because government reports said BPA was not safe for humans. Many news stories wrote about BPA safety.

A 2010 report from the United States Food and Drug Administration said that contact with BPA could hurt fetuses, infants and young children. In September 2010, Canada became the first country to say that BPA was a toxic substance. In the European Union and Canada, BPA cannot be used to make baby bottles.

Uses

BPA will react with other chemicals to make different types of plastic. The most common use of BPA is to make polycarbonate. In this reaction, BPA reacts with phosgene to make a long chain made of carbonate esters. Hydrogen chloride is made as a byproduct, so a base is usually added to neutralise it.[source?]

BPA is also used to make bisphenol A diglycidyl ether (BADGE). This reaction uses epichlorohydrin and a strong base like sodium hydroxide.[source?] BADGE is an ingredient in epoxy resin and other thermoset materials like vinyl ester resin.

The use of these plastics for bottles, plumbing, and canning means that contamination of food and drinking water by BPA is a public health problem. Because of this, people have started to use alternatives to BPA for food and drink containers.

Health effects

Bisphenol A damages the way hormones regulate (control) the human body (endocrine disruptor). BPA can pretend to be the body's own hormones. BPA may cause health problems. Very young children are most sensitive to BPA. Some studies have shown that there is a link (connection) between BPA exposure before birth and later problems of the nervous system. Health organizations have decided how much BPA (in a substance) is safe for people. But new studies have caused other scientists and health organizations to disagree with these decisions. A 2011 study that investigated the number of chemicals to which pregnant women in the U.S. are exposed found BPA in 96% of women.

Expert panel conclusions

In 2007, 38 experts on bisphenol A wrote a scientific consensus statement which said average levels in people are above those that cause harm to many animals in laboratory experiments. However, the experts noted that 1) BPA is not persistent in the environment or in humans, 2) biomonitoring surveys indicate that exposure is continuous, 3) it is hard to use acute animal exposure studies to estimate daily human exposure to BPA, and 4) no studies that had examined BPA pharmacokinetics in animal models had followed continuous low level exposures. The measurement of BPA levels in human serum and other body fluids suggests that either BPA intake is much higher than previously thought or that BPA can bioaccumulate in some conditions such as pregnancy, or both. A 2011 study, the first to examine BPA in a continuous low level exposure throughout the day, did find an increased absorption and accumulation of BPA in the blood of mice.

In 2007, 153 government-funded BPA experiments on lab animals and tissues found adverse effects and 14 did not. In contrast, all 13 studies funded by chemical corporations reported no harm. The studies indicating harm reported a variety of harmful effects in rodent offspring exposed in the womb: abnormal weight gain, insulin resistance, prostate cancer, and too much mammary gland development.

A panel convened by the U.S. National Institutes of Health in 2007 determined that there was "some concern" about BPA's effects on fetal and infant brain development and behavior. The concern over the effect of BPA on infants was also heightened by the fact that infants and children are estimated to have the highest daily intake of BPA. A 2008 report by the U.S. National Toxicology Program later agreed with the panel, expressing "some concern for effects on the brain, behavior, and prostate gland in fetuses, infants, and children at current human exposures to bisphenol A," and "minimal concern for effects on the mammary gland and an earlier age for puberty for females in fetuses, infants, and children at current human exposures to bisphenol A." The NTP had "negligible concern that exposure of pregnant women to bisphenol A will result in fetal or neonatal mortality, birth defects, or reduced birth weight and growth in their offspring."

Other opinions

In 2009, The Endocrine Society said it was worried about current human exposure to BPA.

In 2011, the United Kingdom Food Standards Agency's chief scientist said "the evidence [is] that BPA is rapidly absorbed, detoxified, and eliminated from humans – therefore is not a health concern."

References

  1. ↑ Qu, Jianli; Guo, Ruyue; Liu, Lin; Ren, Fangfang; Jin, Hangbiao (2024). "Occurrence of bisphenol analogues and their conjugated metabolites in foodstuff". Science of the Total Environment. 948 174922. Bibcode:2024ScTEn.94874922Q. doi:10.1016/j.scitotenv.2024.174922. PMID 39038674.
  2. ↑ "Update on Bisphenol A for Use in Food Contact Applications: January 2010". U.S. Food and Drug Administration. 15 January 2010. Archived from the original on 19 January 2010. Retrieved 15 January 2010.
  3. ↑ "CANADIAN ENVIRONMENTAL PROTECTION ACT, 1999" (PDF). Canada Gazette Part II. 144 (21): 1806–18. 13 October 2010.
  4. ↑ Martin Mittelstaedt (13 October 2010). "Canada first to declare bisphenol A toxic". The Globe and Mail. Canada. Archived from the original on 2 January 2012. Retrieved 21 August 2017.
  5. ↑ EU to ban Bisphenol A in baby bottles in 2011 101125
  6. ↑ {{cite journal|doi=10.1016/j.toxlet.2007.11.001]}
  7. ↑ Gore, Andrea C. (8 June 2007). Endocrine-Disrupting Chemicals: From Basic Research to Clinical Practice. Contemporary Endocrinology. Humana Press. ISBN 978-1588298300.
  8. ↑ O’Connor, JC; Chapin, RE (2003). "Critical evaluation of observed adverse effects of endocrine active substances on reproduction and development, the immune system, and the nervous system" (Full Article). Pure Appl. Chem. 75 (11–12): 2099–2123. Bibcode:2003PApCh..75.2099O. doi:10.1351/pac200375112099. S2CID 97899046. Retrieved 28 February 2007.
  9. ↑ Okada H; Tokunaga T; Liu X; Takayanagi S; Matsushima A; Shimohigashi Y (January 2008). "Direct evidence revealing structural elements essential for the high binding ability of bisphenol A to human estrogen-related receptor-gamma". Environ. Health Perspect. 116 (1): 32–8. Bibcode:2008EnvHP.116...32O. doi:10.1289/ehp.10587. PMC 2199305. PMID 18197296.
  10. ↑ vom Saal FS, Myers JP (2008). "Bisphenol A and Risk of Metabolic Disorders". JAMA. 300 (11): 1353–5. Bibcode:2008JAMA..300.1353V. doi:10.1001/jama.300.11.1353. PMID 18799451.
  11. ↑ Draft Screening Assessment for The Challenge Phenol, 4,4' -(1-methylethylidene)bis- (Bisphenol A)Chemical Abstracts Service Registry Number 80-05-7. Health Canada, 2008.
  12. ↑ Ginsberg G, Rice DC (2009). "Does Rapid Metabolism Ensure Negligible Risk from Bisphenol A?". EPH. 117 (11): 1639–1643. Bibcode:2009EnvHP.117.1639G. doi:10.1289/ehp.0901010. PMC 2801165. PMID 20049111.[permanent dead link]
  13. ↑ Beronius, A.; Rudén, C.; Håkansson, H.; Hanberg, A. (2009). "Risk to all or none?-A comparative analysis of controversies in the health risk assessment of Bisphenol A". Reproductive Toxicology (Elmsford, N.Y.). 29 (2): 132–146. doi:10.1016/j.reprotox.2009.11.007. PMID 19931376.
  14. ↑ "99% of pregnant women in US test positive for multiple chemicals including banned ones, study suggests". ScienceDaily.
  15. ↑ vom Saal FS; Akingbemi BT; Belcher SM; et al. (2007). "Chapel Hill bisphenol A expert panel consensus statement: integration of mechanisms, effects in animals and potential to impact human health at current levels of exposure". Reprod. Toxicol. 24 (2): 131–8. Bibcode:2007RepTx..24..131V. doi:10.1016/j.reprotox.2007.07.005. PMC 2967230. PMID 17768031.
  16. ↑ "Bisphenol A (BPA) accumulates more rapidly within the body than previously thought". ScienceDaily.
  17. ↑ "Chemical & Engineering News: Government & Policy - Bisphenol a on Trial".
  18. ↑ Are BPA Products Safe for Infants and Children? Archived 2011-07-25 at the Wayback Machine, National Research Center for Women and Families Website.
  19. ↑ Since you asked - Bisphenol A: Questions and Answers about the Draft National Toxicology Program Brief on Bisphenol A Archived 2010-05-13 at the Wayback Machine, National Institute of Environmental Health Sciences website.
  20. ↑ "Endocrinology News - Healio". www.healio.com.
  21. ↑ Wage, Andrew (27 July 2011). "Small pond, same big issues". FSA. Archived from the original on 10 September 2011. Retrieved 3 August 2011.

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