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Bisphenol A (BPA) is an organic synthetic compound with the
chemical formula A chemical formula is a way of presenting information about the chemical proportions of atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes ...
(CH3)2C(C6H4OH)2 belonging to the group of
diphenylmethane Diphenylmethane is an organic compound with the chemical formula, formula (C6H5)2CH2 (often abbreviated ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid. Diphenylmethane is a com ...

diphenylmethane
derivatives and
bisphenol The bisphenols () are a group of chemical compounds with two hydroxyphenyl functionalities. Most of them are based on diphenylmethane Diphenylmethane is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic com ...
s, with two hydroxyphenyl
group A group is a number A number is a mathematical object used to counting, count, measurement, measure, and nominal number, label. The original examples are the natural numbers 1, 2, 3, 4, and so forth. Numbers can be represented in language with ...
s. It is a colorless
solid Solid is one of the four fundamental states of matter 4 (four) is a number A number is a mathematical object A mathematical object is an abstract concept arising in mathematics. In the usual language of mathematics, an ''object'' is an ...

solid
that is
soluble In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence i ...

soluble
in
organic solvent A solvent (from the Latin Latin (, or , ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken in the area around Rome, known as Latium. Through the power of the ...

organic solvent
s, but poorly soluble in water (0.344 wt % at 83 °C). BPA is a
precursor Precursor or Precursors may refer to: *Precursor (religion) In religion, a precursor, also known as forerunner, predecessor, harbinger or herald, is a holy person who announced the approaching appearance of a central figure of the religion or who ...
to important
plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. Synthetic may also refer to: In the sense of both "combination" and "artificial" * Synthetic chemical or s ...

plastic
s, primarily certain
polycarbonate Polycarbonates (PC) are a group of thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material c ...

polycarbonate
s and
epoxy resin Epoxy is the family of basic components or cured A cure is a completely effective treatment for a disease. Cure, or similar, may also refer to: Places * Cure (river), a river in France * Cures, Sabinum, an ancient Italian town * Cures, S ...

epoxy resin
s, as well as some
polysulfone Polysulfones are a family of high performance thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplast ...

polysulfone
s and certain niche materials. BPA-based plastic is clear and tough, and is made into a variety of common consumer goods, such as
plastic bottle A plastic bottle is a bottle constructed from high-density or low density plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. Synthetic may also r ...

plastic bottle
s (including
water bottle A water bottle is a container that is used to hold water Water (chemical formula H2O) is an , transparent, tasteless, odorless, and , which is the main constituent of 's and the s of all known living organisms (in which it acts as a ) ...

water bottle
s),
food storage container Food storage containers are widespread in use throughout the world and have probably been in use since the first human civilizations. Early civilizations In early civilizations cereal grains such as maize Maize ( ; ''Zea mays'' subsp. ''m ...
s,
baby bottle A baby bottle, or nursing bottle, or feeding bottle, is a bottle with a teat (also called a nipple in the US) to drink directly from. It is typically used by infant 222x222px, Eight-month-old sororal twin sisters An infant (from the La ...

baby bottle
s,
sports equipment Sporting equipment, also called sporting goods, are the tools, materials, apparel, and gear used to compete in a sport and varies depending on the sport. The equipment ranges from balls, nets, and protective gear Personal protective equipm ...
,
CDs The compact disc (CD) is a digital Digital usually refers to something using discrete digits, often binary digits. Technology and computing Hardware *Digital electronics Digital electronics is a field of electronics The field of ele ...

CDs
, and
DVD The DVD (common abbreviation for Digital Video Disc or Digital Versatile Disc) is a digital Digital usually refers to something using digits, particularly binary digits. Technology and computing Hardware *Digital electronics Digital elect ...

DVD
s. Epoxy resins derived from BPA are used to line water pipes, as coatings on the inside of many food and beverage cans, and in making
thermal paper Thermal paper (sometimes referred to as an audit roll) is a special fine paper that is coated with a material formulated to change color when exposed to heat. It is used in thermal printers, particularly in inexpensive or lightweight devices su ...

thermal paper
such as that used in sales receipts. In 2015, an estimated 4 million tonnes of BPA-derived chemical were produced, making it one of the highest volume of chemicals produced worldwide. BPA is a
xenoestrogen Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as Polychlorinated biphenyls, PCBs, Bisphenol A ...
, exhibiting
estrogen Estrogens or oestrogens, are a class of natural or synthetic sex hormone Sex hormones, also known as sex steroids, gonadocorticoids and gonadal steroids, are steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid ho ...

estrogen
-mimicking,
hormone A hormone (from the Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is appr ...

hormone
-like properties. Although the effect is very weak, the pervasiveness of BPA-containing materials raises concerns. Since 2008, several governments have investigated its safety, which prompted some retailers to withdraw polycarbonate products. Since then, BPA-free plastics have been manufactured using alternative bisphenols such as
bisphenol S Bisphenol S (BPS) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, be ...

bisphenol S
and
bisphenol F Bisphenol F (BPF; 4,4’-dihydroxydiphenylmethane) is a small aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), p ...

bisphenol F
, but there is controversy around whether these are actually safer.


History

Bisphenol A was prepared in 1891 by Russian chemist
Aleksandr Dianin Aleksandr Pavlovich Dianin (russian: Александр Павлович Дианин; 20 April 1851 – 6 December 1918) was a Russians, Russian chemist from Saint Petersburg. He carried out studies on phenols and discovered a phenol derivative ( ...
. In 1934 workers at I.G. Farbenindustrie reported the coupling of BPA and
epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic co ...

epichlorohydrin
. Over the following decade, coatings and resins derived from similar materials were described by workers at the companies of DeTrey Freres in Switzerland and DeVoe and Raynolds in the US. This early work underpinned the development of epoxy resins, which in turn motivated production of BPA. The utilization of BPA further expanded with discoveries at
Bayer Bayer Aktiengesellschaft, AG (; ) is a German multinational corporation, multinational pharmaceutical company, pharmaceutical and life sciences company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, ...

Bayer
and
General Electric General Electric Company (GE) is an American Multinational corporation, multinational Conglomerate (company), conglomerate incorporated in New York State and headquartered in Boston. Until 2021, the company operated through GE Aviation, aviat ...
on polycarbonate plastics. These plastics first appeared in 1958, being produced by Mobay and General Electric, and Bayer.Volker Serini "Polycarbonates" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000. In terms of the endocrine disruption controversy, the British biochemist Edward
Charles Dodds Sir Edward Charles Dodds, 1st Baronet (13 October 1899 – 16 December 1973) was a British biochemist. Personal life He was born in Liverpool in 1899, the only child of Ralph Edward Dodds, a shoe retailer, and Jane (née Pack) Dodds. The family s ...
tested BPA as an artificial estrogen in the early 1930s. He found BPA to be 1 / 37,000 as effective as estradiol. Dodds eventually developed a structurally similar compound,
diethylstilbestrol Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for women with a ...

diethylstilbestrol
(DES), which was used as a synthetic estrogen drug in women and animals until it was banned due to its risk of causing cancer; the ban on use of DES in humans came in 1971 and in animals, in 1979. BPA was never used as a drug.


Uses

In 2003, U.S. consumption was 856,000 tons, of which 75% was used to make polycarbonate plastic and 21% for epoxy resins. In the U.S., less than 5% of the BPA produced is used in food contact applications, but remains in the canned food industry and printing applications, such as sales receipts.


Polycarbonates

Bisphenol A is a precursor to
polycarbonate Polycarbonates (PC) are a group of thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material c ...

polycarbonate
plastics. Its reaction with
phosgene Phosgene is the organic chemical compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, mo ...

phosgene
is conducted under biphasic conditions; the hydrochloric acid is scavenged with aqueous base: : 3.6 million tonnes (8 billion pounds) of BPA are consumed for this purpose yearly. These polymers do not contain BPA, but esters derived from it.


Epoxy and vinyl ester resins

BPA is a precursor in production of major classes of
resin In polymer chemistry Polymer chemistry is a sub-discipline of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, stru ...

resin
s, specifically the
vinyl ester resin Vinyl ester resin, or often just vinyl ester, is a resin produced by the esterification of an epoxy Epoxy is the family of basic components or cured A cure is a completely effective treatment for a disease. Cure, or similar, may also refer ...
s. This application usually begins with alkylation of BPA with
epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic co ...

epichlorohydrin
.


Specialized derivatives

BPA is a versatile building block from which many derivatives have been prepared.
Nitration In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, pro ...

Nitration
gives . Bromination gives
tetrabromobisphenol A Tetrabromobisphenol A (TBBPA) is a brominated flame retardant. The compound is a white solid (not colorless), although commercial samples appear yellow. It is one of the most common fire retardants. Production and use TBBPA is produced by the r ...

tetrabromobisphenol A
(TBBPA), which exhibits
fire retardant A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability , Germany ) , image_map = , map_caption = ...
properties. Several drug candidates have been developed from bisphenol A, including
Ralaniten Ralaniten (developmental code name EPI-002) is an N-terminal domain antiandrogen which was never marketed. It is a derivative In mathematics Mathematics (from Greek: ) includes the study of such topics as numbers (arithmetic and num ...

Ralaniten
,
Ralaniten acetate Ralaniten acetate (developmental code name EPI-506) is a first-in-class antiandrogen that targets the N-terminal domain, ''N''-terminal domain (NTD) of the androgen receptor (AR) developed by ESSA Pharmaceuticals and was under investigation for th ...

Ralaniten acetate
, and
EPI-001 EPI-001 is the first inhibitor of the androgen receptor amino-terminal domain. The single stereoisomer of EPI-001, EPI-002, is a first-in-class drug that the USAN council assigned a new stem class "-aniten" and the generic name "ralaniten". This d ...

EPI-001
.


Health effects

BPA's ability to mimic the effects of natural estrogen derive from the similarity of phenol groups on both BPA and
estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous cycle, estrous and menstrual cycle, menstrual female reproductive cycles. Estradiol is resp ...

estradiol
, which enable this synthetic molecule to trigger estrogenic pathways in the body. Typically phenol-containing molecules similar to BPA are known to exert weak estrogenic activities, thus it is also considered an endocrine disruptor (ED) and estrogenic chemical. Xenoestrogens is another category the chemical BPA fits under because of its capability to interrupt the network that regulates the signals which control the reproductive development in humans and animals. BPA has been found to bind to both of the nuclear
estrogen receptor Estrogen receptors (ERs) are a group of proteins found inside cell (biology), cells. They are receptor (biochemistry), receptors that are activated by the hormone estrogen (17β-estradiol). Two classes of ER exist: nuclear estrogen receptors (ER ...
s (ERs),
ERα Estrogen receptor alpha (ERα), also known as NR3A1 (nuclear receptor subfamily 3, group A, member 1), is one of two main types of estrogen receptor Estrogen receptors (ERs) are a group of proteins found inside cells. They are receptors that are ...
and
ERβ Estrogen receptor beta (ERβ) also known as NR3A2 (nuclear receptor subfamily 3, group A, member 2) is one of two main types of estrogen receptor Estrogen receptors (ERs) are a group of proteins found inside cell (biology), cells. They are rec ...

ERβ
. It is 1000- to 2000-fold less potent than estradiol. BPA can both mimic the action of
estrogen Estrogens or oestrogens, are a class of natural or synthetic sex hormone Sex hormones, also known as sex steroids, gonadocorticoids and gonadal steroids, are steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid ho ...

estrogen
and antagonize estrogen, indicating that it is a
selective estrogen receptor modulator Selective estrogen receptor modulators (SERMs), also known as estrogen receptor agonist/antagonists (ERAAs), are a class of drug Uncoated tablets, consisting of about 90% acetylsalicylic acid, along with a minor amount of inert fillers and b ...
(SERM) or
partial agonist In pharmacology Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which ex ...
of the ER. At high concentrations, BPA also binds to and acts as an
antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist 200px, Shakespeare's ''Hamlet, Prince of Denmark.'' William Morris Hunt, oil on canvas, c. 1864 A protagonist (from grc, πρωταγωνιστής, ...
of the
androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor In the field of molecular biology, nuclear receptors are a class of proteins found within cells that are responsi ...

androgen receptor
(AR). In addition to receptor binding, the compound has been found to affect
Leydig cell Leydig cells, also known as interstitial cells of Leydig, are found adjacent to the seminiferous tubules Seminiferous tubules are located within the testes Testicle or testis (plural testes) is the male reproductive gland or gonad A go ...
steroidogenesis A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes which alter membrane fluidity; and ...

steroidogenesis
, including affecting 17α-hydroxylase/17,20 lyase and
aromatase Aromatase, also called estrogen synthetase or estrogen synthase, is an enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are cal ...
expression and interfering with
LH receptor The luteinizing hormone/choriogonadotropin receptor (LHCGR), also lutropin/choriogonadotropin receptor (LCGR) or luteinizing hormone receptor (LHR) is a transmembrane receptor found predominantly in the ovary and testis, but also many extragonadal ...
-ligand binding. In 1997, adverse effects of low-dose BPA exposure in laboratory animals were first proposed. Some studies have found that BPA increases anxiety in rats. Modern studies began finding possible connections to health issues caused by exposure to BPA during pregnancy and during development. As of 2014, research and debates are ongoing as to whether BPA should be banned or not. A 2007 study investigated the interaction between bisphenol A's and estrogen-related receptor γ (ERR-γ). This
orphan receptor In biochemistry Biochemistry or biological chemistry, is the study of chemical process In a scientific Science () is a systematic enterprise that Scientific method, builds and organizes knowledge in the form of Testability, testable ex ...
(endogenous ligand unknown) behaves as a constitutive activator of transcription. BPA seems to bind strongly to ERR-γ (
dissociation constant In chemistry, biochemistry, and pharmacology, a dissociation constant (K_D) is a specific type of equilibrium constant that measures the propensity of a larger object to separate (dissociate) reversibly into smaller components, as when a Complex (ch ...
= 5.5 nM), but only weakly to the ER. BPA binding to ERR-γ preserves its basal constitutive activity. It can also protect it from deactivation from the SERM 4-hydroxytamoxifen (afimoxifene). This may be the mechanism by which BPA acts as a
xenoestrogen Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as Polychlorinated biphenyls, PCBs, Bisphenol A ...
. Different expression of ERR-γ in different parts of the body may account for variations in bisphenol A effects. BPA has also been found to act as an
agonist An agonist is a chemical that binds to a receptor and activates the receptor to produce a biological response. In contrast, an antagonist blocks the action of the agonist, while an inverse agonist causes an action opposite to that of the agonist ...

agonist
of the
GPER G protein-coupled estrogen receptor 1 (GPER), also known as G protein-coupled receptor 30 (GPR30), is a protein that in humans is encoded by the ''GPER'' gene. GPER binds to and is activated by the female sex hormone estradiol and is responsible f ...
(GPR30). According to the
European Food Safety Authority The European Food Safety Authority (EFSA) is the agency Agency may refer to: * a governmental or other institution Institutions, according to Samuel P. Huntington, are "stable, valued, recurring patterns of behavior". Institutions can refer ...
"BPA poses no health risk to consumers of any age group (including unborn children, infants and adolescents) at current exposure levels". But in 2017 the
European Chemicals Agency The European Chemicals Agency (ECHA; ) is an agency of the European Union An agency of the European Union is a decentralised body of the European Union The European Union (EU) is a political and economic union of Member state of the ...

European Chemicals Agency
concluded that BPA should be listed as a substance of very high concern due to its properties as an
endocrine disruptor Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine The endocrine system is a messenger system compri ...
. In 2012, the United States'
Food and Drug Administration The United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, st ...
(FDA) banned the use of BPA in
baby bottle A baby bottle, or nursing bottle, or feeding bottle, is a bottle with a teat (also called a nipple in the US) to drink directly from. It is typically used by infant 222x222px, Eight-month-old sororal twin sisters An infant (from the La ...

baby bottle
s. The U.S.
Environmental Protection Agency A biophysical environment is a biotic Biotics describe living or once living components of a community; for example organisms, such as animals and plants. Biotic may refer to: *Life, the condition of living organisms *Biology, the study of life ...
(EPA) holds the position that BPA is not a health concern. In 2011, Andrew Wadge, the chief scientist of the United Kingdom's
Food Standards Agency , type = Non-ministerial government department Non-ministerial government departments (NMGDs) are a type of department of the Government of the United Kingdom that deal with matters for which direct political oversight has been judged unnecess ...
, commented on a 2011 U.S. study on dietary exposure of adult humans to BPA, saying, "This corroborates other independent studies and adds to the evidence that BPA is rapidly absorbed, detoxified, and eliminated from humans – therefore is not a health concern." The
Endocrine Society The Endocrine Society is a professional, international medical organization in the field of endocrinology Endocrinology (from '' endocrine'' + '' -ology'') is a branch of biology Biology is the natural science that studies life and livin ...
said in 2015 that the results of ongoing laboratory research gave grounds for concern about the potential hazards of endocrine-disrupting chemicals – including BPA – in the environment, and that on the basis of the
precautionary principle The precautionary principle (or precautionary approach) is a broad epistemological Epistemology (; ) is the branch of philosophy concerned with knowledge Knowledge is a familiarity or awareness, of someone or something, such as fac ...

precautionary principle
these substances should continue to be assessed and tightly regulated. A 2016 review of the literature said that the potential harms caused by BPA were a topic of scientific debate and that further investigation was a priority because of the association between BPA exposure and adverse human health effects including reproductive and developmental effects and metabolic disease. In July 2019, the European Union upheld a decision by the
European Chemicals Agency The European Chemicals Agency (ECHA; ) is an agency of the European Union An agency of the European Union is a decentralised body of the European Union The European Union (EU) is a political and economic union of Member state of the ...

European Chemicals Agency
to list BPA as a
substance of very high concern A substance of very high concern (SVHC) is a chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday ...
, the first step in the procedure for restrictions of its use. The decision is based on concerns about BPA's toxicity for human reproduction.


Environmental effects

In 2010, the U.S. Environmental Protection Agency reported that over one million pounds of BPA are released into the environment annually. BPA can be released into the environment by both pre-consumer and post-consumer leaching. Common routes of introduction from the pre-consumer perspective into the environment are directly from plastics, coat and staining manufacturers, foundries who use BPA in casting sand, or transport of BPA and BPA-containing products. Post-consumer BPA waste comes from effluent discharge from municipal wastewater treatment plants, irrigation pipes used in agriculture, ocean-borne plastic trash, indirect leaching from plastic, paper, and metal waste in landfills, and paper or material recycling companies. Despite a rapid soil and water
half-life Half-life (symbol ''t''1⁄2) is the time required for a quantity to reduce to half of its initial value. The term is commonly used in nuclear physics Nuclear physics is the field of physics Physics is the natural science that studies ...
of 4.5 days, and an air half-life of less than one day, BPA's ubiquity makes it an important
pollutant A pollutant is a substance or energy introduced into the environment that has undesired effects, or adversely affects the usefulness of a resource. A pollutant may cause long- or short-term damage by changing the growth rate of plant or animal s ...
. BPA has a low rate of evaporation from water and soil, which presents issues, despite its
biodegradability Biodegradation is the breakdown of organic matter Organic matter, organic material, or natural organic matter refers to the large source of Carbon compounds, carbon-based compounds found within natural and engineered, terrestrial, and aquatic ...
and low concern for bio-accumulation. BPA has low volatility in the atmosphere and a low
vapor pressure Vapor pressure (or vapour pressure in British English British English (BrE) is the standard dialect A standard language (also standard variety, standard dialect, and standard) is a language variety that has undergone substantial cod ...

vapor pressure
between 5.00 and 5.32 Pascals. Aqueous solutions of BPA absorbs at wavelengths greater than 250 nm. BPA interferes with
nitrogen fixation Nitrogen fixation is a chemical process by which molecular nitrogen Nitrogen is the chemical element upright=1.0, 500px, The chemical elements ordered by link=Periodic table In chemistry Chemistry is the science, scientific st ...
at the roots of
leguminous A legume () is a plant Plants are predominantly photosynthetic Photosynthesis is a process used by plants and other organisms to Energy transformation, convert light energy into chemical energy that, through cellular respiration, can ...

leguminous
plants associated with the bacterial symbiont ''
Sinorhizobium meliloti ''Ensifer meliloti'' (formerly ''Rhizobium meliloti'' and ''Sinorhizobium meliloti'') are an Aerobic respiration, aerobic, Gram staining, Gram-negative, and diazotrophic species of bacteria. ''S. meliloti'' are Motility, motile and possess a clu ...
.'' BPA affects
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume A legume () is a plant Plants are predominantly photosynthetic Photosynthesis is a process used by plants and other organisms to Energy transformation ...

soybean
seedlings with respect to root growth,
nitrate Nitrate is a polyatomic ion A polyatomic ion, also known as a molecular ion, is a covalently bonded A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the format ...

nitrate
production,
ammonium The ammonium cation An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects t ...

ammonium
production, and the activities of
nitrate reductase Nitrate reductases are molybdoenzymes that reduce Reduce is a general-purpose computer algebra system geared towards applications in physics. The development of the Reduce computer algebra system was started in the 1960s by Anthony C. Hearn. ...

nitrate reductase
and nitrite reductase. At low doses of BPA, the growth of roots were improved, the amount of nitrate in roots increased, the amount of ammonium in roots decreased, and the nitrate and nitrite reductase activities remained unchanged. However, at considerably higher concentrations of BPA, the opposite effects were seen for all but an increase in nitrate concentration and a decrease in nitrite and
nitrate reductase Nitrate reductases are molybdoenzymes that reduce Reduce is a general-purpose computer algebra system geared towards applications in physics. The development of the Reduce computer algebra system was started in the 1960s by Anthony C. Hearn. ...

nitrate reductase
activities. Nitrogen is both a plant nutritional substance, but also the basis of growth and development in plants. A 2005 study conducted in the United States had found that 91–98% of BPA may be removed from water during treatment at municipal water treatment plants. A more detailed explanation of aqueous reactions of BPA can be observed in the Degradation of BPA section below. Nevertheless, a 2009 meta-analysis of BPA in the surface water system showed BPA present in surface water and sediment in the U.S. and Europe. According to
Environment Canada Environment and Climate Change Canada (ECCC; french: Environnement et Changement climatique Canada)Environment and Climate Change Canada is the applied title under the Federal Identity Program on the Remote Manipulator System, Canadarm The Fede ...
in 2011, "BPA can currently be found in municipal wastewater. nitial assessment shows that at low levels, bisphenol A can harm fish and organisms over time." BPA affects growth, reproduction, and development in aquatic organisms. Among freshwater organisms, fish appear to be the most sensitive species. Evidence of endocrine-related effects in fish, aquatic invertebrates, amphibians, and reptiles has been reported at environmentally relevant exposure levels lower than those required for acute toxicity. There is a widespread variation in reported values for endocrine-related effects, but many fall in the range of 1μg/L to 1 mg/L. A 2009 review of the biological impacts of
plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity Plasticity may refer to: Science * Plasticity (physics), in engineering and physics, the propensity of ...
s on wildlife published by the
Royal Society The Royal Society, formally The Royal Society of London for Improving Natural Knowledge, is a learned society A learned society (; also known as a learned academy, scholarly society, or academic association) is an organization that exis ...
with a focus on aquatic and terrestrial
annelids The annelids (Annelida , from Latin Latin (, or , ) is a classical language A classical language is a language A language is a structured system of communication Communication (from Latin ''communicare'', meaning "to share ...
,
molluscs Mollusca is the second-largest phylum In biology, a phylum (; plural The plural (sometimes list of glossing abbreviations, abbreviated ), in many languages, is one of the values of the grammatical number, grammatical category of number ...

molluscs
,
crustaceans Crustaceans (Crustacea ) form a large, diverse arthropod An arthropod (, (gen. ποδός)) is an invertebrate Invertebrates are animals that neither possess nor develop a vertebral column (commonly known as a ''backbone'' or ''spine''), de ...
, insects, fish and
amphibian Amphibians are ectothermic, tetrapod vertebrates of the Class (biology), class Amphibia. All living amphibians belong to the group Lissamphibia. They inhabit a wide variety of habitats, with most species living within terrestrial animal, ter ...
s concluded that BPA affects reproduction in all studied animal groups, impairs development in crustaceans and amphibians and induces genetic aberrations.


Toxicity

BPA exhibits very low acute toxicity as indicated by its
LD50 In toxicology Toxicology is a scientific discipline Discipline is action ACTION is a bus operator in Canberra Canberra ( ) is the capital city of Australia. Founded following the Federation of Australia, federation of the col ...
of 4 g/kg (mouse). In those mice, weight gain was reduced and exhibited estrogen-like properties. Reports indicate that it is a minor skin irritator as well, though less so than
phenol Phenol (also called carbolic acid) is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), plane (geometry), p ...

phenol
. The FDA's National Center for Toxicology Research conducted its own research studies. In rodent studies, the amount of BPA passed from the mother to the unborn offspring after oral administration was found to be insignificant. The BPA administration dose for the rodents was 100-1000 times higher than human exposure.


Production

World production capacity of BPA was 1 million tons in the 1980s, and more than 2.2 million tons in 2009. It is a high production volume chemical. This compound is synthesized by the
condensation Condensation is the change of the state of matter In physics Physics is the natural science that studies matter, its Elementary particle, fundamental constituents, its Motion (physics), motion and behavior through Spacetime, space ...
of
acetone Acetone, or propanone, is an organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, ...

acetone
(hence the suffix A in the name) with two
equivalents ''Equivalents'' is a series of photographs of clouds taken by Alfred Stieglitz from 1925 to 1934. They are generally recognized as the first photographs intended to free the subject matter from literal interpretation, and, as such, are some of the ...
of
phenol Phenol (also called carbolic acid) is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), plane (geometry), p ...

phenol
. The reaction is
catalyzed that utilizes a low-temperature oxidation catalyst to convert carbon monoxide to less toxic carbon dioxide at room temperature. It can also remove formaldehyde from the air. Catalysis () is the process of increasing the reaction rate, rate of a ...

catalyzed
by a strong acid, such as
hydrochloric acid Hydrochloric acid +(aq) Cl−(aq) or H3O+ Cl− also known as muriatic acid, is an aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a salin ...

hydrochloric acid
(HCl) or a . Industrially, a large excess of phenol is used to ensure full condensation; the product mixture of the
cumene process The cumene process (cumene–phenol process, Hock process) is an industrial process Industrial processes are procedures involving chemical A chemical substance is a form of matter having constant chemical composition and characteristic propert ...
(acetone and phenol) may also be used as starting material: : Numerous
ketone In chemistry Chemistry is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or something, such as facts A fact is an occurrence i ...
s undergo analogous condensation reactions.


BPA substitutes

Concerns about the health effects of BPA have led many manufacturers to replace BPA with substitutes such as
bisphenol S Bisphenol S (BPS) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, be ...

bisphenol S
(BPS) and diphenyl sulfone. However, health concerns have been raised about these substitutes as well.


Identification in plastics

In the U.S., plastic packaging is split into seven broad classes for identification purposes by a
Resin identification code The ASTM International Resin Identification Coding System, often abbreviated RIC, is a set of symbols appearing on plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic ch ...

Resin identification code
. As of 2014 there are no BPA labeling requirements for plastics in the U.S. "In general, plastics that are marked with Resin Identification Codes 1, 2, 4, 5, and 6 are very unlikely to contain BPA. Some, but not all, plastics that are marked with the Resin Identification Code 7 may be made with BPA." Type 7 is the catch-all "other" class, and some type 7 plastics, such as
polycarbonate Polycarbonates (PC) are a group of thermoplastic A thermoplastic, or thermosoft plastic, is a plastic polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material c ...

polycarbonate
(sometimes identified with the letters "PC" near the
recycling symbol The universal recycling symbol ( or in Unicode Unicode, formally the Unicode Standard, is an information technology Technical standard, standard for the consistent character encoding, encoding, representation, and handling of Character ( ...

recycling symbol
) and epoxy resins, are made from bisphenol A monomer. Type 3 (
PVC Polyvinyl chloride (colloquial Colloquialism or colloquial language is the linguistic style used for casual (informal) communication Communication (from Latin Latin (, or , ) is a classical language belonging to the Italic la ...

PVC
) may contain bisphenol A as an antioxidant (not a plasticizer) in "flexible PVC" softened by
plasticizers A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity Plasticity may refer to: Science * Plasticity (physics), in engineering and physics, the propensity of ...
, but not rigid PVC such as pipe, window frames, and siding.


Legislation

The U.S.
Food and Drug Administration The United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, st ...
(FDA) has ended its authorization of the use of BPA in
baby bottle A baby bottle, or nursing bottle, or feeding bottle, is a bottle with a teat (also called a nipple in the US) to drink directly from. It is typically used by infant 222x222px, Eight-month-old sororal twin sisters An infant (from the La ...

baby bottle
s and infant formula packaging, based on market abandonment, not safety. The
European Union The European Union (EU) is a political and economic union of member states that are located primarily in Europe Europe is a which is also recognised as part of , located entirely in the and mostly in the . It comprises the wester ...

European Union
and Canada have banned BPA use in baby bottles. Currently in the United States, there are 12 states, in addition to Washington D.C. that have restrictions in place against BPA. These states include California, Connecticut, Delaware, Maine, Maryland, Massachusetts, Minnesota, Nevada, New York, Vermont, Washington, and Wisconsin. Each state's restrictions differ slightly, but all restrict the use of BPA in some way. The following are some examples of legislation in place in these states: * California - Assembly Bill 1319 (2011) prohibits the manufacture and sale of bottles and cups with BPA at detectable levels above 0.1 parts per billion if these items are meant to be used by children 3 years old or younger. It requires manufacturers to use alternative non-toxic materials that are not categorized as carcinogenic or reproductive toxicants. * Delaware - Senate Bill 70 (2011) prohibits the sale of bottles and cups containing BPA if the items are designed to be used by children 4 years old or younger. * Illinois - Senate Bill 2950 (2011) prohibits the sale of empty containers like bottles or cups designed to store food and beverage for children that contain BPA * Maine - House Bill 330 (2011) helped process BPA to be recognized as a priority chemical under Title 38, §1691, Maine's law on toxic chemicals in products designed to be used by children. BPA was formally designated as a substance that must pass through certain reporting requirements for manufactureres of products that contain BPA, as well as authorize the prohibition of sale of products that are reported to contain BPA.


See also

* *
Bisphenol S Bisphenol S (BPS) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, be ...

Bisphenol S


References


Further reading

* * {{Authority control 2,2-Bis(4-hydroxyphenyl)propanes Bis(4-hydroxyphenyl)methanes Commodity chemicals Endocrine disruptors GPER agonists Medical controversies Nonsteroidal antiandrogens Plasticizers Russian inventions Selective estrogen receptor modulators Xenoestrogens