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14-September-2008 18:38:41 - Bisphenol A Bisphenol A Bisphenol A IUPAC name 4,4'-dihydroxy-2,2-diphenylpropane Other names BPA, 4,4'-propan-2-ylidenediphenol, p, p'-isopropylidenebisphenol, 4,4´-isopropylidenediphenol. Identifiers CAS number 80-05-7 RTECS number SL6300000 SMILES CCc2cccOcc2Cc1cccOcc1 Properties Molecular formula C15H16O2 228.286906 g/mol 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 0 3 0 R/S statement R: 36, 37, 38, 43 S: 24, 26, 37 Flash point 227 °C, autoignition: 600 °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 Infobox references Bisphenol A, commonly abbreviated as BPA, is an organic compound with two phenol functional groups. It is a difunctional building block of several important polymers and polymer additives. With an annual production of approximately 3 million tonnes, it is an important monomer in the production of polycarbonate. Suspected of being hazardous to humans since the 1930s, concerns about the use of Bisphenol A in consumer products grabbed headlines in 2008 when several governments issued reports questioning its safety, and some retailers pulled products made from it off their shelves. Contents 1 Synthesis 2 Use 3 Health effects 3.1 Endocrine disruption 3.2 Selected studies on low dose bisphenol A exposure in animals 3.3 Human exposure to bisphenol A 4 Government and industry response 5 Environmental risk 6 Identification in plastics 7 References 8 External links Synthesis Bisphenol A was first reported by A.P. Dianin in 1891.12 It is prepared by the condensation of acetone hence the suffix A in the name3 with two equivalents of phenol. The reaction is catalyzed by an acid, such as hydrochloric acid HCl or a sulfonated polystyrene resin. Typically, a large excess of phenol is used to ensure full condensation: CH32CO + 2 C6H5OH → CH32CC6H4OH2 + H2O A large number of ketones undergo analogous condensation reactions. The method is efficient and the only by-product is water.4 Use Further information: Polycarbonate Products containing or made from Bisphenol A have been in commerce for more than 50 years, and its current uses are numerous. It is used in the synthesis of polyesters, polysulfones, and polyether ketones, as an antioxidant in some plasticizers, and as a polymerization inhibitor in PVC. It is a key monomer in production of polycarbonate plastic and epoxy resins.4 Polycarbonate plastic, which is clear and nearly shatter-proof, is used to make a variety of common products including baby and water bottles, sports equipment, medical devices, CDs, and household electronics.5 Epoxy resins are used as coatings on the inside of almost all food and beverage cans.6 It is also a precursor to the flame retardant, tetrabromobisphenol A, and was formerly used as a fungicide.7 Global production of bisphenol A in 2003 was estimated to be about 3 million metric tonnes t.8 In the U.S., it is manufactured by Bayer MaterialScience, Dow Chemical Company, General Electric, Hexion Specialty Chemicals, and Sunoco Chemicals. In 2004, these companies produced just over 1 million t of bisphenol A, up from just 7,260 t in 1991. In 2003, annual U.S. consumption was 856,000 t, 72% of which was used to make polycarbonate plastic and 21% going into epoxy resins.5 Health effects Bisphenol A has low acute toxicity, with an oral LD50 of 3250 mg/kg in rats.9 However, bisphenol A is an endocrine disruptor: it is an estrogen receptor agonist,10 and such agonists can act like the body's own hormones, leading to similar physiological effects on the body.11 There is thus concern that long term low dose exposure to bisphenol A may induce chronic toxicity in humans.121314 Endocrine disruption The first evidence of the estrogenicity of bisphenol A came from experiments in the 1930s in which it was fed to ovariectomized rats,1516 but it was not until 1997 that adverse effects of low-dose exposure on laboratory animals were first reported.6 Since then, its endocrine disrupting properties have been extensively investigated, and more than 100 studies have been published raising health concerns about the chemical.17 Early development appears to be the period of greatest sensitivity to its effects,18 and studies have demonstrated developmental toxicity, carcinogenic effects, and possible neurotoxicity at low doses in animal models see table below.1920 Recent studies suggest it may also be linked to obesity21 by triggering fat-cell activity22 and have confirmed that bisphenol A exposure during development has carcinogenic effects and produce precursors of breast cancer.2324 However, neither the U.S. Environmental Protection Agency25 nor the International Agency for Research on Cancer26 have evaluated Bisphenol A for possible carcinogenic activity. Most recently, a study by the Yale School of Medicine demonstrated that adverse neurological effects occur in non-human primates regularly exposed to bisphenol A at levels equal the EPA's maximum safe dose of 50 µg/kg/day.2728 In 2007, a consensus statement by 38 experts on bisphenol A concluded that average levels in people are above those that cause harm to animals in laboratory experiments,29 and a panel convened by the U.S. National Institutes of Health determined that there was some concern about BPA's effects on fetal and infant brain development and behavior.5 A 2008 report by the U.S. National Toxicology Program NTP 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.30 In April 2008, the Health Canada released its Draft Screening Assessment for bisphenol A, which concluded that the chemical may pose some risk to infants31 and proposed classifying the chemical as 'toxic' to human health and the environment.32 This action follows Canadian regulators selection of bisphenol A in 2006 as one of 200 substances deserving of thorough safety assessments because preliminary studies had found it to be inherently toxic; the chemical had not previously been studied by them in depth, having been accepted under grandfather clauses when stricter regulations were passed in the 1980s.33 In contrast to the recent actions in North America, in January 2006 the German Federal Institute for Risk Assessment announced that polycarbonate baby bottles are safe and stated that published research on the health effects of Bisphenol A is difficult to interpret and is occasionally contradictory.34 An assessment released later that year by the European Union's Food Safety Authority reached a similar conclusion, expressing considerable reservations about the biological significance and robustness of the low-dose exposure studies on rodents.35 In 2007 Japan also concluded that for individuals in that country, the current exposure levels of BPA will not pose any unacceptable risk to human health and that a ban is not needed.36 Some toxicologists and regulatory agencies have criticized low-dose toxicity studies, especially those that involved injecting bisphenol A directly into animals, since human exposures typically involve ingestion and subsequent metabolism in the liver, and the experimental design of a few of these early studies has also been questioned.3738 On the other hand, studies have also appeared pointing out flaws in chemical industry funded studies that found no evidence of adverse effects from low dose exposure,39 and a study from 2008 concluded that blood levels of bisphenol A in neonatal mice are the same whether it is injected or ingested.40 Selected studies on low dose bisphenol A exposure in animals Dose µg/kg/day Effects measured in studies of mice or rats, descriptions are from Environmental Working Group4133 Study Year 0.025 Permanent changes to genital tract 200542 0.025 Changes in breast tissue that predispose cells to hormones and carcinogens 200543 2 increased prostate weight 30% 199744 2 lower bodyweight, increase of anogenital distance in both genders, signs of early puberty and longer estrus. 200245 2.4 Decline in testicular testosterone 200446 2.5 Breast cells predisposed to cancer 200747 10 Prostate cells more sensitive to hormones and cancer 200648 10 Decreased maternal behaviors 200249 30 Reversed the normal sex differences in brain structure and behavior 200350 50 U.S. human exposure limit not a result from an animal study, but a guideline set by EPA 199851 Human exposure to bisphenol A Bisphenol A has been known to leach from the plastic lining of canned foods52 and, to a lesser degree, polycarbonate plastics that are cleaned with harsh detergents or used to contain acidic or high-temperature liquids. Studies by the CDC found bisphenol A in the urine of 95% of adults sampled in 1988-199453 and in 93% of children and adults tested in 2003-04.54 Almost all exposure is through diet, and infants fed with liquid formula are among the most exposed. Infants fed canned formula with polycarbonate bottles can consume quantities of bisphenol A up to 13 µg/kg/day see table below,55 while the most sensitive animal studies show effects at much lower concentrations. Debate continues on what the safe limit of this compound is. Within the United States, an exposure of up to 50 µg/kg/day 50 ppb/day is considered safe33 by the United States Environmental Protection Agency.56 Dr. Maida Galvez, a pediatrician studying BPA, recommends parents stay away from bottles containing the chemical and says, We know the animal studies raise concerns, but there aren't human studies showing effects yet ... so, when we don't have the evidence, what we recommend is that parents try to err on the side of caution.57 Population Estimated daily bisphenol A intake, μg/kg/day. Table adapted from the National Toxicology Program Expert Panel Report.5 Infant 0-6 months formula-fed 1-11 Infant 0-6 months breast-fed 0.2-1 Infant 6-12 months 1.65-13 Child 1.5-6 years 0.043-14.7 Adult 0.008-1.5 Government and industry response On April 18, 2008 Canadian Health Minister Tony Clement announced that Canada intends to ban the import, sale, and advertising of polycarbonate baby bottles containing bisphenol A over concerns about the safety of bisphenol A. While Health Canada concluded that human exposures are less than the levels deemed to be potentially unsafe, the margin of safety was considered too low for formula-fed infants.1858 Around the same time, Wal-Mart announced that it was immediately ceasing sales in all its Canadian stores of food containers, water and baby bottles, sippy cups, and pacifiers containing bisphenol A, and that it would phase out baby bottles made with it in U.S. stores by early 2009.59 Nalgene also announced it will stop using the chemical in its products,60 and Toys-R-Us said it too will cease selling baby bottles made from it.61 Subsequent news reports showed many retailers removing polycarbonate drinking products from their shelves.62 As of the release of NTP and Health Canada reports, 10 U.S. states, including California,63 Maryland,17 Connecticut64 and New Jersey,65 already had legislation pending that would affect the use of BPA, and in the wake of these reports, U.S. Senator Charles Schumer D-N.Y. introduced legislation that would ban bisphenol A nationally from products for infants.17 In addition, the U.S. Congress is investigating the Weinberg Group, a chemical industry consulting firm, for its role in downplaying the health effects of bisphenol A and other chemicals,66 and the Energy and Commerce Committee in the House of Representatives is investigating the use of BPA in baby products as well as the FDA's approval of the chemical. In asking the FDA to reassess its approval of bisphenol A, committee chairman Bart Stupak D-Mich. said We would expect the FDA to make decisions based on the best available science...Yet the FDA relied on only two industry-funded studies, while other respected authorities used all available data to reach vastly different conclusions. The FDA maintains that bisphenol A is safe and is not recommending that people avoid using products made from it. The Consumer Product Safety Commission agrees, and its deputy director has stressed that use of bisphenol A based plastics has many practical benefits, and that a ban could result in less effective protection of children from head, eye, or bodily injury.6 FDA has set up a task force to address these concerns, and in August it released a draft finding67 concurring with its initial position that the chemical is safe. The agency will make its final decision after an advisory panel on the issues is convened in September.68 In response to the recent events, an American Chemistry Council ACC/BPA Global Group spokesman said, The weight of scientific evidence, as assessed by Health Canada and other agencies around the world, provides reassurance that consumers can continue to safely use products made from bisphenol A.69 The ACC says that bisphenol A does not pose a risk to consumers and has called on the Food and Drug Administration to review the chemical. The ACC also called the media coverage of the controversy unnecessarily confusing and frightening the public.64 The Grocery Manufacturers Association also insists that bisphenol A is safe, and argues that Data purporting to demonstrate 'low' dose effects on the male reproductive system by BPA have not been successfully replicated and, therefore, are not credible to estimate human health risks and safety in light of the weight of a large body of evidence to the contrary.70 A spokesman for the tin can industry has said that without lining cans with bisphenol A based resins, E. coli and botulism poisoning would be rampant.6 An industry website Bisphenol-a.org also carries a number of articles dated as recently as February 2008 claiming the use of Polycarbonate water bottles is safe. The chemical industry has been criticized over bisphenol A by Democrats and their allies. David Michaels, who served in the Clinton Administration, told the Washington Post that Tobacco figured this out, and essentially it's the same model ... If you fight the science, you're able to postpone regulation and victim compensation, as well. As in this case, eventually the science becomes overwhelming. But if you can get five or 10 years of avoiding pollution control or production of chemicals, you've greatly increased your product.17 In the U.S. retail sector, growing concern over bisphenol A exposure had already led a number of retailers to stop using bisphenol A, particularly chains promoting healthy food and lifestyles. In 2005, Patagonia Inc. ceased selling polycarbonate bottles, and in 2006, Whole Foods Markets ceased selling baby bottles as did Mountain Equipment Co-op in 2007.71 Environmental risk As an environmental contaminant this compound interferes with nitrogen fixation at the roots of leguminous plants associated with the bacterial symbiont Sinorhizobium meliloti. Despite a half-life in the soil of only 1-10 days, its ubiquity makes it an important pollutant.72 According to Health Canada, initial assessment shows that at low levels, bisphenol A can harm fish and organisms over time. Studies also indicate that it can currently be found in municipal wastewater.73 Identification in plastics Some type 7 plastics may leach bisphenol A Some type 7 plastics may leach bisphenol A Some type 3 plastics may leach bisphenol A Some type 3 plastics may leach bisphenol A There are seven classes of plastics used in packaging applications. Type 7 is the catch-all other class, and some type 7 plastics, such as polycarbonate sometimes identified with the letters PC near the recycling symbol and epoxy resins, are made from bisphenol A monomer.4 When such plastics are exposed to hot liquids, bisphenol A leaches out 55 times faster than it does under normal conditions, at up to 32 ng/hour.74 Type 3 PVC can also contain bisphenol A as antioxidant in plasticizers.4 Types 1 PET, 2 HDPE, 4 LDPE, 5 polypropylene, and 6 polystyrene do not use bisphenol A during polymerization or package forming,75 and thus will not leach bisphenol A into food or beverages. References ^ Dianin 1891. Zhurnal russkogo fiziko-khimicheskogo obshchestva 23: pp. 492-. ^ Zincke, Theodor 1905. Ueber die Einwirkung von Brom und von Chlor auf Phenole: Substitutionsprodukte, Pseudobromide und Pseudochloride. Justus Liebigs Annalen der Chemie 343: 75-99. doi:10.1002/jlac.19053430106. ^ Uglea, Constantin V.; Ioan I. Negulescu 1991. Synthesis and Characterization of Oligomers. CRC Press, page 103. ^ a b c d Fiege, Helmut 2002, Phenol Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a19_313 ^ a b c d National Toxicology Program, U.S. Department of Health and Human Services 2007-11-26. CERHR Expert Panel Report for Bisphenol A. Retrieved on 2008-04-18. ^ a b c d Erickson, Britt E. June 2, 2008. Bisphenol A under scrutiny. Chemical and Engineering News 86 22: 36-39. American Chemical Society. ^ Pesticideinfo.org: Bisphenol A ^ Draft Screening Assessment for The Challenge Phenol, 4,4' -1-methylethylidenebis- Bisphenol A Chemical Abstracts Service Registry Number 80-05-7, Environment Canada. ^ MSDS: Bisphenol A 99+% ^ Okada H, Tokunaga T, Liu X, Takayanagi S, Matsushima A, Shimohigashi Y Jan 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. PMID 18197296. ^ O'Connor, Chapin 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. Retrieved on 2007-02-28. ^ vom Saal FS, Hughes C 2005. An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment. Environ. Health Perspect. 113 8: 926-33. PMID 16079060. ^ Hot liquids release potentially harmful chemicals in polycarbonate plastic bottles ^ Le HH, Carlson EM, Chua JP, Belcher SM 2008. Bisphenol A is released from polycarbonate drinking bottles and mimics the neurotoxic actions of estrogen in developing cerebellar neurons. Toxicol. Lett. 176 2: 149-56. doi:10.1016/j.toxlet.2007.11.001. PMID 18155859. ^ E. C. Dodds and Wilfrid Lawson, Synthetic Œstrogenic Agents without the Phenanthrene Nucleus, Nature, 137 1936, 996. ^ E. C. Dodds and W. Lawson, Proceedings of the Royal Society of London, Series B, Biological Sciences, 125, #839 27-IV-1938, pp. 222-232. ^ a b c d Layton, Lyndsey April 27, 2008, Studies on Chemical In Plastics Questioned Congress Examines Role Of Industry in Regulation, Washington Post: A1, http://www.washingtonpost.com/wp-dyn/content/article/2008/04/26/AR2008042602126.html . ^ a b Draft Screening Assessment for The Challenge Phenol, 4,4' -1-methylethylidenebis- Bisphenol AChemical Abstracts Service Registry Number 80-05-7. Health Canada, 2008. ^ Lee YM, Seong MJ, Lee JW, et al Mar 2007. Estrogen receptor independent neurotoxic mechanism of bisphenol A, an environmental estrogen. J. Vet. Sci. 8 1: 27-38. PMID 17322771. ^ Zsarnovszky A, Le HH, Wang HS, Belcher SM. 2005. Ontogeny of rapid estrogen-mediated extracellular signal-regulated kinase signaling in the rat cerebellar cortex: potent nongenomic agonist and endocrine disrupting activity of the xenoestrogen bisphenol A. Endocrinology. 146 12: 5388-96. doi:10.1210/en.2005-0565. PMID 16123166. ^ Bisphenol A linked to obesity in mice, study says, CTV News 2008-05-15. Retrieved on 2008-05-16. ^ Grossman, Elizabeth. March 12, 2007. Chemicals May Play Role in Rise in Obesity. Washington Post.. ^ Murray TJ, Maffini MV, Ucci AA, Sonnenschein C, Soto AM 2007. Induction of mammary gland ductal hyperplasias and carcinoma in situ following fetal bisphenol A exposure. Reprod. Toxicol. 23 3: 383-90. doi:10.1016/j.reprotox.2006.10.002. PMID 17123778. ^ Soto AM, Vandenberg LN, Maffini MV, Sonnenschein C 2008. Does breast cancer start in the womb?. Basic Clin. Pharmacol. Toxicol. 102 2: 125-33. doi:10.1111/j.1742-7843.2007.00165.x inactive 2008-06-22. PMID 18226065. ^ U.S.EPA, IRIS: Bisphenol A ^ AGENTS REVIEWED BY THE IARC MONOGRAPHS Volumes 1-99 ^ Leranth C, Hajszan T, Szigeti-Buck K, Bober J, Maclusky NJ September 2008. Bisphenol A prevents the synaptogenic response to estradiol in hippocampus and prefrontal cortex of ovariectomized nonhuman primates. Proc. Natl. Acad. Sci. U.S.A.. doi:10.1073/pnas.0806139105. PMID 18768812. ^ Layton, Lindsey Sept. 4, 2008. Chemical in Plastic Is Connected to Health Problems in Monkeys, Washington Post, pp. A02. Retrieved on 2008-09-06. ^ 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. PMID 17768031. ^ 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. ^ Morrissey, Susan R. April 23, 2008, Banning Bisphenol A In Baby Bottles: Canada moves toward restricting the chemical; Congress proposes similar legislation, Chemical and Engineering News, http://pubs.acs.org/cen/news/86/i17/8617news4.html . ^ Government of Canada Takes Action on Another Chemical of Concern: Bisphenol A, Chemical Substances, Health Canada. Accessed April 19, 2008. ^ a b c Mittelstaedt, Martin 2007-04-07. 'Inherently toxic' chemical faces its future, Globe Mail. Retrieved on 2007-04-07. ^ Selected questions and answers relating to bisphenol A in baby bottles- Federal Institute for Risk Assessment ^ Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food AFC related to 2,2-BIS4-HYDROXYPHENYLPROPANE, European Food Safety Authority, November 29, 2006. Accessed April 19, 2008 ^ Bisphenol A Risk Assessment Document AIST Risk Assessment Document Series No. 4 Summary, New Energy and Industrial Technology Development Organization, Research Center for Chemical Risk Management, National Institute of Advanced Industrial Science and Technology, November 2007. ^ Goodman JE, McConnell EE, Sipes IG, et al 2006. An updated weight of the evidence evaluation of reproductive and developmental effects of low doses of bisphenol A. Crit. Rev. Toxicol. 36 5: 387-457. doi:10.1080/10408440600758317. PMID 16954066. ^ Weight of the Evidence Evaluation of Low-Dose Reproductive and Developmental Effects of Bisphenol A, George M. Gray, Joshua T. Cohen, Gerald Cunha, Claude Hughes, Ernest E. McConnell, Lorenz Rhomberg, I. Glenn Sipes, and Donald Mattison7Human and Ecological Risk Assessment, 10: 875-921, 2004. ^ vom Saal FS, Welshons WV Jan 2006. Large effects from small exposures. II. The importance of positive controls in low-dose research on bisphenol A. Environ. Res. 100 1: 50-76. doi:10.1016/j.envres.2005.09.001. PMID 16256977. ^ Taylor JA, Welshons WV, Vom Saal FS February 2008. No effect of route of exposure oral; subcutaneous injection on plasma bisphenol A throughout 24h after administration in neonatal female mice. Reprod. Toxicol. 25 2: 169-76. doi:10.1016/j.reprotox.2008.01.001. PMID 18295446. Retrieved on 2008-05-05. ^ This table is adapted from: EWG, 2007. Many studies confirm BPA's low-dose toxicity across a diverse range of toxic effects, Environmental Working Group Report: A Survey of Bisphenol A in U.S. Canned Foods. Accessed November 4th, 2007 at http://www.ewg.org/node/20941. All studies included in this table where judged by the CEHRH panel to be at least of moderate usefulness for assessing the risk of BPA to human reproduction. ^ Markey CM, Wadia PR, Rubin BS, Sonnenschein C, Soto AM 2005. Long-term effects of fetal exposure to low doses of the xenoestrogen bisphenol-A in the female mouse genital tract. Biol. Reprod. 72 6: 1344-51. doi:10.1095/biolreprod.104.036301. PMID 15689538. ^ Muñoz-de-Toro M, Markey CM, Wadia PR, et al 2005. Perinatal exposure to bisphenol-A alters peripubertal mammary gland development in mice. Endocrinology 146 9: 4138-47. doi:10.1210/en.2005-0340. PMID 15919749. ^ Nagel SC, vom Saal FS, Thayer KA, Dhar MG, Boechler M, Welshons WV 1997. Relative binding affinity-serum modified access RBA-SMA assay predicts the relative in vivo bioactivity of the xenoestrogens bisphenol A and octylphenol. Environ. Health Perspect. 105 1: 70-6. PMID 9074884. ^ Honma S, Suzuki A, Buchanan DL, Katsu Y, Watanabe H, Iguchi T 2002. Low dose effect of in utero exposure to bisphenol A and diethylstilbestrol on female mouse reproduction. Reprod. Toxicol. 16 2: 117-22. PMID 11955942. ^ Akingbemi BT, Sottas CM, Koulova AI, Klinefelter GR, Hardy MP 2004. Inhibition of testicular steroidogenesis by the xenoestrogen bisphenol A is associated with reduced pituitary luteinizing hormone secretion and decreased steroidogenic enzyme gene expression in rat Leydig cells. Endocrinology 145 2: 592-603. doi:10.1210/en.2003-1174. PMID 14605012. ^ Murray TJ, Maffini MV, Ucci AA, Sonnenschein C, Soto AM 2007. Induction of mammary gland ductal hyperplasias and carcinoma in situ following fetal bisphenol A exposure. Reprod. Toxicol. 23 3: 383-90. doi:10.1016/j.reprotox.2006.10.002. PMID 17123778. ^ Ho SM, Tang WY, Belmonte de Frausto J, Prins GS 2006. Developmental exposure to estradiol and bisphenol A increases susceptibility to prostate carcinogenesis and epigenetically regulates phosphodiesterase type 4 variant 4. Cancer Res. 66 11: 5624-32. doi:10.1158/0008-5472.CAN-06-0516. PMID 16740699. ^ Palanza PL, Howdeshell KL, Parmigiani S, vom Saal FS 2002. Exposure to a low dose of bisphenol A during fetal life or in adulthood alters maternal behavior in mice. Environ. Health Perspect. 110 Suppl 3: 415-22. PMID 12060838. ^ Kubo K, Arai O, Omura M, Watanabe R, Ogata R, Aou S 2003. Low dose effects of bisphenol A on sexual differentiation of the brain and behavior in rats. Neurosci. Res. 45 3: 345-56. PMID 12631470. ^ EPA Environmental Protection Agency. 1988. Oral RfD Assessment: Bisphenol A. Integrated Risk Information System. ^ Environmental Working Group. Retrieved on 2007-03-07. ^ Calafat AM, Kuklenyik Z, Reidy JA, Caudill SP, Ekong J, Needham LL 2005. Urinary concentrations of bisphenol A and 4-nonylphenol in a human reference population. Environ. Health Perspect. 113 4: 391-5. PMID 15811827. ^ Calafat AM, Ye X, Wong LY, Reidy JA, Needham LL 2008. Exposure of the U.S. population to bisphenol A and 4-tertiary-octylphenol: 2003-2004. Environ. Health Perspect. 116 1: 39-44. doi:10.1289/ehp.10753. PMID 18197297. ^ European Food Safety Authority Opinion Abstract. Retrieved on 2007-02-28. ^ Bisphenol A - United States Environmental Protection Agency ^ Parents Concerned Over Potentially Toxic Baby Bottles ABC News, Feb. 7, 2008. ^ The government has given the public 60 days to comment on the proposed ban starting April 19, 2008 and will evaluate whether the ban will become law in October 2008. Government of Canada Takes Action on Another Chemical of Concern: Bisphenol A. Retrieved on 2008-04-18. ^ Wal-Mart to pull baby bottles made with chemical BPA: Washington Post, Market Watch, April 18, 2008. ^ Bottle Maker to Stop Using Plastic Linked to Health Concerns, New York Times, April 18, 2008. ^ Toys 'R' Us to phase out bisphenol A baby bottles, CBC News 2008-04-22. Retrieved on 2008-04-22. ^ CANOE - CNEWS - Politics: Bisphenol A water-bottle removal expanding among Canadian retailers ^ Bill List ^ a b Weil, William April 23, 2008, Debate In A Bottle dead link - Scholar search, Hartford Courant, http://www.courant.com/features/lifestyle/green/hc-bottled.art0apr23,0,5170837.story . ^ Momentum Builds to End BPA in Plastics, NewsInferno.com, April 22, 2008, http://www.newsinferno.com/archives/2955 . ^ Congressional Probe Targets Consulting Group, Integrity in Science Watch, Center for Science in the Public Interest, 02/11/2008. ^ http://www.fda.gov/ohrms/dockets/ac/08/briefing/2008-0038b1_01_02_FDA%20BPA%20Draft%20Assessment.pdf DRAFT ASSESSMENT OF BISPHENOL A FOR USE IN FOOD CONTACT APPLICATIONS, US Food and Drug Administration, undated. ^ Health Highlights: Aug. 16, 2008, Washington Post Aug. 16, 2008. Retrieved on 2008-08-17. ^ Canada bans BPA plastic from baby bottles, Kansas City Star, Apr. 18, 2008 . ^ Canada Could Ban Baby Bottles Containing Bisphenol A, Environment News Service 2008-04-22. Retrieved on 2008-04-24. ^ Polycarbonate bottles raise questions, Associated Press 2007-12-23. ^ Fox, J.E., J. Gulledge, E. Engelhaupt, M.E. Burrow J.A. McLachlan 2007. Pesticides reduce symbiotic efficiency of nitrogen-fixing rhizobia and host plants. Proc. Nat. Acad. Sci. 104: 10282-7. doi:10.1073/pnas.0611710104. PMID 17548832. ^ Bisphenol A Fact Sheet, Health Canada. Assessed April 19, 2008. ^ Biello D 2008-02-19. Plastic not fantastic: Food containers leach a potentially harmful chemical. Scientific American 2. Retrieved on 2008-04-09. ^ http://www.ehponline.org/docs/2006/8804/letter.html Environmental Health Perspectives Volume 114, Number 2, February 2006 External links US FDA statement on bisphenol A Plastics chemical alters female brains Frontline Fooling With Nature, interview Fredrick Vom Saal, Ph.D. News report on effect through plastic bottles Bisphenol A. A Known Endocrine Disruptor WWF publication Plastics Industry Bisphenol A information site United States Environmental Protection Agency page on Bisphenol A An Endocrine/Estrogen Letter special Report on BPA News coverage of bisphenol A from EnvironmentalHealthNews.org The Toxic Origins of Disease, Liza Gross, PLoS Biology - an essay examining some of the evidence and effects. CHEMICAL FALLOUT: JOURNAL SENTINEL WATCHDOG REPORT, Milwaukee Journal Star newspaper article examining effects of Bisphenol A on lab animals and humans. Safe Use Of Plastic Food Packaging And Containers, Agri-Food Veterinary, Authority of Singapore Human Exposure to Bisphenol A, Vandenberg, L.N., et al. via Living on Earth Hazard in a bottle Attempt to regulate BPA in California defeated from The Economist v d e Health issues of plastics Plasticizers: Phthalates DIBP · DBP · BBP aka BBzP · DEHP aka DOP · DIDP · DINP · DIDP Other plasticizers Organophosphates · Adipate-based DEHA · DOA Hardeners Bisphenol A in Polycarbonates Other additives PBDEs · PCBs · Organotins Health issues Teratogen · Carcinogen · Endocrine disruptor · Diabetes · Obesity Miscellaneous PVC · Plastic recycling · Plastic bottle · Vinyl chloride · dioxin · polystyrene · Styrofoam · PTFE Teflon · California Proposition 65 1986 · List of environmental health hazards · Persistent organic pollutant Retrieved from http://en..org/wiki/Bisphenol_A Categories: Phenols | Plasticizers | Russian inventionsHidden categories: Pages with DOIs broken since 2008 | All articles with dead external links | Articles with dead external links since June 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Česky Dansk Deutsch Français Nederlands 日本語 Polski Suomi Svenska 中文 This page was last modified on 9 September 2008, at 15:30
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So many of us do not eat a balanced diet, get enough sleep, have too much stress, or are impacted with toxins and pollutants. Drinking 2 ounces of MonaVie twice a day will help your body detoxify as well as build your immune system. Its the smartest thing you can do for yourself, so start today. Buying MonaVie through our company guarantees you support 7 days a week and, if you would like to share MonaVie with your family and friends we will guide you from start to finish.
1. Click on Enroll Now (30 - 55% off retail price)
2. Pay $39 for your Wholesale ID number.
3. NO minimum order required.
4. MonaVie is delivered to your door in 3 to 5 days.