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Bisphenol A

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.

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

Scientist discovered in the mid 1930s that people and animals react to BPA in the same way that they react to hormone (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 (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]

Uses

Uses: in at least one European country, BPA is used in epoxy glue for repairing pipes that transport water into apartments.[5]

In at least one other European country, BPA is part of surfaces of rotors (sometimes nicknamed propellor) of wind turbines; In at least one (place or) municipality, rotors with BPA are not permitted near a lake that is a source of drinking water.[6]

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.[7][8][9][10] Very young children are most sensitive to BPA.[11] 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. [12][13] 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.[14]

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.[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 harmful 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 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]

Other opinions

In 2009, The Endocrine Society said it was worried about current human exposure to BPA.[20]

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."[21]

Bisphenol A Media

  • Synthesis of bisphenol A from phenol and acetone

  • Polycarbonate water bottle.JPG

    Bisphenol A is primarily used to make plastics, such as this polycarbonate water bottle.

  • Polycarbonatsynthese.svg

    Synthesis of polycarbonate from bisphenol-A and phosgene

  • Diglycidether.svg

    Synthese Diglycidether auf der Basis von Bisphenol A

  • Bisphenol AF.svg

    Bisphenol AF; Hexafluorobisphenol a; 4,4'-(Hexafluoroisopropylidene)diphenol

  • Bisphenol F.svg

    Bisphenol F; 4,4'-Bisphenol F; Bis(4-hydroxyphenyl)methane

  • Structure of Bisphenol S

  • Bisphenol Z.svg

    Bisphenol Z; 4,4'-Cyclohexylidenebisphenol

  • Tetramethyl bisphenol F.png

    Skeletal structure of tetramethyl bisphenol F

  • Import canned foods in Kobe.jpg

    The largest exposure humans have had to BPA is from food packaging, particularly the epoxy lining of metal food, beverage cans and plastic bottles.

References

  1. ↑ "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.
  2. ↑ "CANADIAN ENVIRONMENTAL PROTECTION ACT, 1999" (PDF). Canada Gazette Part II. 144 (21): 1806–18. 13 October 2010.
  3. ↑ Martin Mittelstaedt (13 October 2010). "Canada first to declare bisphenol A toxic". The Globe and Mail (Canada). https://www.theglobeandmail.com/news/national/canada-first-to-declare-bisphenol-a-toxic/article1755272/. Retrieved 21 August 2017. 
  4. ↑ EU to ban Bisphenol A in baby bottles in 2011 101125
  5. ↑ https://yle.fi/a/74-20080206. Retrieved 2024-03-21
  6. ↑ https://www.nrk.no/tromsogfinnmark/flytter-vindturbiner-_-unngar-drikkevannskilde-pa-raggovidda-1.16855346. Retrieved 2024-04-24
  7. ↑ Gore, Andrea C. (8 June 2007). Endocrine-Disrupting Chemicals: From Basic Research to Clinical Practice. Contemporary Endocrinology. Humana Press. ISBN 978-1588298300.
  8. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
  9. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
  10. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
  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. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).[dead link]
  13. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
  14. ↑ "99% of pregnant women in US test positive for multiple chemicals including banned ones, study suggests". ScienceDaily.
  15. ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
  16. ↑ "Bisphenol A (BPA) accumulates more rapidly within the body than previously thought". ScienceDaily.
  17. ↑ http://pubs.acs.org/cen/government/85/8516gov2.html
  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.

Other websites

Template:Androgen receptor modulators

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