Bisphenol A

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Bisphenol A
Bisphenol A.svg
Bisphenol A.png
IUPAC name 4,4'-(propane-2,2-diyl)diphenol
Other names BPA, p,p'-isopropylidenebisphenol,
2,2-bis(4-hydroxyphenyl)propane.
Identifiers
CAS number 80-05-7
PubChem 6623
EC number 201-245-8
DrugBank DB06973
KEGG C13624
ChEBI CHEBI:33216
RTECS number SL6300000
SMILES Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
Properties
Molecular formula C15H16O2
Molar mass 228.28 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

Solubility in water 120–300 ppm (at 21.5 °C)
Hazards
NFPA 704

NFPA 704.svg

0
3
0
 
R-phrases R36, R37, R38, R43
S-phrases S24, S26, S37
Flash point 227 °C
Related compounds
Related compounds phenols
Bisphenol S
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Bisphenol A (BPA) is an organic compound which has two phenol functional groups. It is used to make polycarbonate plastic, epoxy resins, and other things.

Scientist discovered in the mid 1930s that people and animals react to BPA in the same way that they react to hormone (estrogenic 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 (FDA) said that contact with BPA could hurt fetuses (unborn children), infants and young children.[1] In September 2010, Canada became the first country to say that BPA was a toxic substance.[2][3] In the European Union and Canada, BPA cannot be used to make baby bottles.[4]

Health effects[change | change source]

Bisphenol A hurts 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.[5][6][7][8] Very young children are most sensitive to BPA.[9] Some studies have shown that there is a link (connection) between BPA exposure before birth (prenatal) 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. [10][11] 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.[12]

In 2009, The Endocrine Society said it was worried about current human exposure to BPA.[13]

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."[14]

Expert panel conclusions[change | change source]

In 2007, 38 experts on bisphenol A wrote a 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.[15] 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.[16]

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 deleterious effects in rodent offspring exposed in the womb: abnormal weight gain, insulin resistance, prostate cancer, and too much mammary gland development.[17]

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.[18] A 2008 report by the U.S. National Toxicology Program (NTP) 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."[19]

References[change | change source]

  1. "Update on Bisphenol A for Use in Food Contact Applications: January 2010". U.S. Food and Drug Administration. 15 January 2010. http://www.fda.gov/NewsEvents/PublicHealthFocus/ucm197739.htm. Retrieved 15 January 2010.
  2. Canada Gazette Part II 144 (21): 1806–18. 13 October 2010. http://www.gazette.gc.ca/rp-pr/p2/2010/2010-10-13/pdf/g2-14421.pdf.
  3. Martin Mittelstaedt (13 October 2010). "Canada first to declare bisphenol A toxic". The Globe and Mail (Canada). http://www.theglobeandmail.com/news/national/canada-first-to-declare-bisphenol-a-toxic/article1755272/.
  4. EU to ban Bisphenol A in baby bottles in 2011 101125
  5. Gore, Andrea C. (8 June 2007). Endocrine-Disrupting Chemicals: From Basic Research to Clinical Practice. Contemporary Endocrinology. Humana Press. ISBN 978-1588298300 .
  6. 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. doi:10.1351/pac200375112099 . http://www.iupac.org/publications/pac/2003/pdf/7511x2099.pdf. Retrieved 28 February 2007.
  7. 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. doi:10.1289/ehp.10587 . PMC 2199305 . PMID 18197296 .
  8. vom Saal FS, Myers JP (2008). "Bisphenol A and Risk of Metabolic Disorders". JAMA 300 (11): 1353–5. doi:10.1001/jama.300.11.1353 . PMID 18799451 . http://jama.ama-assn.org/cgi/content/full/300.11.1353.
  9. 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.
  10. Ginsberg G, Rice DC (2009). "Does Rapid Metabolism Ensure Negligible Risk from Bisphenol A?". EPH 117 (11): 1639–1643. doi:10.1289/ehp.0901010 . PMC 2801165 . PMID 20049111 . http://www.ehponline.org/members/2009/0901010/0901010.html.
  11. 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 .
  12. http://www.sciencedaily.com/releases/2011/01/110114081653.htm
  13. Endocrine Society released scientific statement on endocrine-disrupting chemicals
  14. Wage, Andrew (27 July 2011). "Small pond, same big issues". FSA. http://blogs.food.gov.uk/science/entry/small_pond_same_big_issues. Retrieved 3 August 2011.
  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. doi:10.1016/j.reprotox.2007.07.005 . PMC 2967230 . PMID 17768031 .
  16. http://www.sciencedaily.com/releases/2011/06/110606075708.htm
  17. http://pubs.acs.org/cen/government/85/8516gov2.html
  18. Are BPA Products Safe for Infants and Children?, 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, National Institute of Environmental Health Sciences website.

Other websites[change | change source]

     . PMID 20414285
      . http://www.nature.com/news/2010/100421/full/4641122a.html. Retrieved 21 April 2010.
  • Kabiersch, G; Rajasärkkä, J; Ullrich, R; Tuomela, M; Hofrichter, M; Virta, M; Hatakka, A; Steffen, K (2011). "Fate of bisphenol a during treatment with the litter-decomposing fungi Stropharia rugosoannulata and Stropharia coronilla". Chemosphere 83 (3): 226–32. doi:10.1016/j.chemosphere.2010.12.094
     . PMID 21295326
      .
  • Vogel, S. A. (2009). "The Politics of Plastics: the Making and Unmaking of Bisphenol A "Safety"". American Journal of Public Health 99 (S3): S559–S566. doi:10.2105/AJPH.2008.159228
     . PMC 2774166
     . PMID 19890158
      .
     . PMC 2661896
     . PMID 19337501
      . http://www.ehponline.org/members/2008/0800173/0800173.html.
  • Hazard in a bottle Attempt to regulate BPA in California defeated (from The Economist)
  • Bisphenol-A News & Products News commentary on BPA Containing Products
  • Bondesson, M.; Jönsson, J.; Pongratz, I.; Olea, N.; Cravedi, J.; Zalko, D.; Håkansson, H.; Halldin, K. et al. (Jul 2009). "A CASCADE of effects of bisphenol A". Reproductive toxicology (Elmsford, N.Y.) 28 (4): 563–567. doi:10.1016/j.reprotox.2009.06.014
     . ISSN 0890-6238
      . PMID 19577634
      .