Tris(1,3-dichloro-2-propyl)phosphate

Last updated
Tris(1,3-dichloro-2-propyl)phosphate
Tris(1,3-dichloro-2-propyl)phosphate.svg
TDCPP 3D ball.png
Names
Preferred IUPAC name
Tris(1,3-dichloropropan-2-yl) phosphate
Other names
  • Tris
  • chlorinated tris
  • tris [2-chloro-1-(chloromethyl ethyl] phosphate
  • tris (1,3-dichloroisopropyl) phosphate
  • tris (1,3-dichloro-2-propyl) phosphate
  • TDCP
  • TDCPP
  • TDCIPP
  • Fyrol FR-2
  • Antiblaze 195[ citation needed ]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.033.767 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 237-159-2
PubChem CID
UNII
  • InChI=1S/C9H15Cl6O4P/c10-1-7(2-11)17-20(16,18-8(3-12)4-13)19-9(5-14)6-15/h7-9H,1-6H2 X mark.svgN=
    Key: ASLWPAWFJZFCKF-UHFFFAOYSA-N X mark.svgN=
  • O=P(OC(CCl)CCl)(OC(CCl)CCl)OC(CCl)CCl
Properties
C9H15Cl6O4P
Molar mass 430.89 g·mol−1
AppearanceColorless liquid
Hazards
GHS labelling: [1]
GHS-pictogram-silhouette.svg
Warning
H351
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tris(1,3-dichloroisopropyl)phosphate (TDCPP) is a chlorinated organophosphate. Organophosphate chemicals have a wide variety of applications and are used as flame retardants, pesticides, plasticizers, and nerve gases. TDCPP is structurally similar to several other organophosphate flame retardants, such as tris(2-chloroethyl) phosphate (TCEP) and tris(chloropropyl)phosphate (TCPP). TDCPP and these other chlorinated organophosphate flame retardants are all sometimes referred to as "chlorinated tris".

Contents

Manufacture

TDCPP is produced by the by the reaction of epichlorohydrin with phosphorus oxychloride.

Uses

Flame retardant

Until the late 1970s, TDCPP was used as a flame retardant in children’s pajamas in compliance with the U.S. Flammable Fabrics Act of 1953. This use was discontinued after children wearing fabrics treated with a very similar compound, tris(2,3-dibromopropyl) phosphate, were found to have mutagenic byproducts in their urine. [2]

Following the 2005 phase-out of PentaBDE in the United States, TDCPP became one of the primary flame retardants used in flexible polyurethane foam used in a wide variety of consumer products, including automobiles, upholstered furniture, and some baby products. [3] [4] [5] [6] TDCPP can also be used in rigid polyurethane foam boards used for building insulation. [7] In 2011 it was reported that TDCPP was found in about a third of tested baby products. [8]

Some fabrics used in camping equipment are also treated with TDCPP to meet CPAI-84, a standard established by the Industrial Fabrics Association International to evaluate the flame resistance of fabrics and other materials used in tents. [9]

Current total production of TDCPP is not well known. In 1998, 2002, and 2006, production in the United States was estimated to be between 4,500 and 22,700 metric tons, [7] and thus TDCPP is classified as a high production volume chemical.

Presence in the environment

TDCPP is an additive flame retardant, meaning that it is not chemically bonded to treated materials. Additive flame retardants are thought to be more likely to be released into the surrounding environment during the lifetime of the product than chemically bonded, or reactive, flame retardants. [7]

TDCPP degrades slowly in the environment and is not readily removed by waste water treatment processes. [7]

Indoors

TDCPP has been detected in indoor dust, although concentrations vary widely. A study of house dust in the U.S. found that over 96% of samples collected between 2002 and 2007 contained TDCPP at an average concentration of over 1.8 ppm, while the highest was over 56 ppm. [5] TDCPP was also detected in 99% of dust samples collected in 2009 in the Boston area from offices, homes, and vehicles. The second study found an average concentration similar to that of the previous study but a greater range of concentrations: one sample collected from a vehicle contained over 300 ppm TDCPP in the dust. [3] Similar concentrations have been reported for dust samples collected in Europe and Japan. [10] [11] [12]

TDCPP has also been measured in indoor air samples. Its detection in air samples, however, is less frequent and generally at lower concentrations than other organophosphate flame retardants such as TCEP and TCPP, likely due to its lower vapor pressure. [7] [13] [14]

Outdoors

Although TDCPP is generally found at the highest concentrations in enclosed environments, such as homes and vehicles, it is widespread in the environment. Diverse environmental samples, ranging from surface water to wildlife tissues, have been found to contain TDCPP. [7] The highest levels of contamination are generally near urban impacted areas; however, samples from even relatively remote reference sites have contained TDCPP. [15] [16]

Human exposure

Humans are thought to be exposed to TDCPP and other flame retardants through several routes, including inhalation, ingestion, and skin contact with treated materials. Rodent studies show that TDCPP is readily absorbed through the skin and gastrointestinal tract. [17] [18] Infants and young children are expected to have the highest exposure to TDCPP and other indoor contaminants for several reasons. Compared to adults, children spend more time indoors and closer to the floor, where they are exposed to higher amounts of dust particles. In addition, they frequently put their hands and other objects into their mouths without washing. [19]

Several studies show that TDCPP can accumulate in human tissues. It has been detected in semen, fat, and breast milk, [20] [21] [22] and the metabolite bis (1,3-dichloropropyl) phosphate (BDCPP) has been detected in urine. [3] [23] [24]

Health effects

Acute

Organophosphate toxicity is classically associated with acetylcholinesterase inhibition. Acetylcholinesterase is an enzyme responsible for breaking down the neurotransmitter acetylcholine. Many organophosphates, especially those designed to act as nerve agents or pesticides, bind with the active site on acetylcholinesterase, preventing it from breaking down acetylcholine. [25] In rodent studies, TDCPP was found to have very low capacity to inhibit acetylcholinesterase, and it is considered to have low acute toxicity. [26] Animals that were given very high doses (>1 g/kg/day) exhibited clinical signs of organophosphate poisoning, including muscle weakness, loss of coordination, hyperactivity, and death. [7]

Chronic

Cancer

Several studies suggest that TDCPP may be carcinogenic. Rodents that were fed TDCPP over two years showed increased tumor formation in the liver and brain. [27] Metabolites of TDCPP were also determined to be mutagenic in bacteria using the Ames test. [2]

In 2011, TDCPP was listed as a carcinogen under California Proposition 65, a law that identifies and regulates chemicals determined by the California Environmental Protection Agency ‘to cause cancer, birth defects or other reproductive harm.’ [28]

Reproduction

Men living in homes with high concentrations of TDCPP in house dust were more likely to have decreased sperm counts and increased serum prolactin levels. [29] Women typically have higher concentrations of the hormone prolactin than men do. Release of prolactin is regulated by the neurotransmitter dopamine. Prolactin is important for regulating lactation, sex drive, and other hormones.

Development

TDCPP and other similar organophosphate flame retardants have been found to disrupt normal development.

Chickens exposed to TDCPP as embryos developed abnormally: Exposure to 45 ug/g resulted in shorter head-to-bill lengths, decreased body weight, and smaller gallbladders, while 7.64 ug/g lowered free thyroxine (T4) levels in the blood. [30]

Similarly, zebrafish raised in water containing TDCPP died or developed severe malformations. When the TDCPP exposure began very early during embryogenesis, by the 2 cell stage, the developing embryos were more severely affected. [31] [32] [33]

TDCPP was found to affect several neurodevelopmental processes in a neuronal cell line. PC12 cells showed decreased cell replication and growth, increased oxidative stress, and altered cellular differentiation. [34] In a developing organism, these effects could change the way the brain cells communicate and function, resulting in permanent changes in nervous system function. [35]

Thyroid

TDCPP exposure was found to alter mRNA expression of several genes that regulate thyroid function in zebrafish embryos and larvae. [36] [37] Early life exposure also changed thyroid hormone levels in both zebrafish and chick embryos: triiodothyronine (T3) levels increased in exposed zebrafish while thyroxine (T4) levels decreased in both species. [30] [37]

TDCPP may affect brain development and function via the thyroid system. Thyroid hormones are critical for normal growth and development and for proper function in the endocrine system. The developing brain in particular is highly sensitive to thyroid hormone disruptions. Disruptions to the thyroid system of either the mother or the fetus during early brain development are associated with lower IQ scores and increased risk for ADHD or other neurobehavioral disorders. [38] [39]

Related Research Articles

Polybrominated diphenyl ethers or PBDEs, are a class of organobromine compounds that are used as flame retardants. Like other brominated flame retardants, PBDEs have been used in a wide array of products, including building materials, electronics, furnishings, motor vehicles, airplanes, plastics, polyurethane foams, and textiles. They are structurally akin to polychlorinated diphenyl ethers (PCDEs), polychlorinated biphenyls (PCBs) and other polyhalogenated compounds, consisting of two halogenated aromatic rings. PBDEs are classified according to the average number of bromine atoms in the molecule. The life-saving benefits of fire retardants led to their popularization. Standards for mass transit vehicles continues to increase as of 2021.

<span class="mw-page-title-main">Flame retardant</span> Substance applied to items to slow burning or delay ignition

The term flame retardant subsumes a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an ignition source and prevent or slow the further development of flames by a variety of different physical and chemical mechanisms. They may be added as a copolymer during the polymerisation process, or later added to the polymer at a moulding or extrusion process or applied as a topical finish. Mineral flame retardants are typically additive, while organohalogen and organophosphorus compounds can be either reactive or additive.

<span class="mw-page-title-main">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine systems. These disruptions can cause numerous adverse human health outcomes including, alterations in sperm quality and fertility, abnormalities in sex organs, endometriosis, early puberty, altered nervous system function, immune function, certain cancers, respiratory problems, metabolic issues, diabetes, obesity, cardiovascular problems, growth, neurological and learning disabilities, and more. Found in many household and industrial products, endocrine disruptors "interfere with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the body that are responsible for development, behavior, fertility, and maintenance of homeostasis ."

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

Environmental toxicants and fetal development is the impact of different toxic substances from the environment on the development of the fetus. This article deals with potential adverse effects of environmental toxicants on the prenatal development of both the embryo or fetus, as well as pregnancy complications. The human embryo or fetus is relatively susceptible to impact from adverse conditions within the mother's environment. Substandard fetal conditions often cause various degrees of developmental delays, both physical and mental, for the growing baby. Although some variables do occur as a result of genetic conditions pertaining to the father, a great many are directly brought about from environmental toxins that the mother is exposed to.

<span class="mw-page-title-main">Tricresyl phosphate</span> Chemical compound

Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant. Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.

<span class="mw-page-title-main">Decabromodiphenyl ether</span> Chemical compound

Decabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). It was commercialised in the 1970s and was initially thought to be safe, but is now recognised as a hazardous and persistent pollutant. It was added to Annex A of the Stockholm Convention on Persistent Organic Pollutants in 2017, which means that treaty members must take measures to eliminate its production and use. The plastics industry started switching to decabromodiphenyl ethane as an alternative in the 1990s, but this is now also coming under regulatory pressure due to concerns over human health.

Pentabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). Because of their toxicity and persistence, their industrial production is to be eliminated under the Stockholm Convention, a treaty to control and phase out major persistent organic pollutants (POP).

Octabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs).

<span class="mw-page-title-main">Tetrabromobisphenol A</span> Chemical compound

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant. The compound is a white solid, although commercial samples appear yellow. It is one of the most common flame retardants.

<span class="mw-page-title-main">Triphenyl phosphate</span> Chemical compound

Triphenyl phosphate (TPhP) is the chemical compound with the formula OP(OC6H5)3. It is the simplest aromatic organophosphate. This colourless solid is the ester (triester) of phosphoric acid and phenol. It is used as a plasticizer and a fire retardant in a wide variety of settings and products.

<span class="mw-page-title-main">Bisphenol S</span> Chemical compound

Bisphenol S (BPS) is an organic compound with the formula (HOC6H4)2SO2. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used in curing fast-drying epoxy resin adhesives. It is classified as a bisphenol, and a close molecular analog of bisphenol A (BPA). BPS differentiates from BPA by possessing a sulfone group (SO2) as the central linker of the molecule instead of a dimethylmethylene group (C 2), which is the case of bisphenol A.

<span class="mw-page-title-main">Tris(2,3-dibromopropyl) phosphate</span> Chemical compound

Tris(2,3-dibromopropyl) phosphate ("tris") is a chemical once widely used as a flame retardant in plastics and textiles.

The ZebraBox is an automated analysis chamber for the non-intrusive video observation of different types of freshwater marine indicator species, such as Dania rerio and Pimephales promelas. It is a type of Larval Photomoter Response (LPR) assay, which is used to monitor the swimming behaviour of larvae.

Silent Spring Institute is a nonprofit organization dedicated to studying and reporting primarily on breast cancer prevention, although its research covers other health-related topics as well.

<span class="mw-page-title-main">2-Ethylhexyl diphenyl phosphate</span> Chemical compound

2-Ethylhexyl diphenyl phosphate (Octicizer) is an organophosphate compound. It acts as both a plasticizer and flame retardant in PVC, its wide liquid range also makes it suitable as a flame retardant in hydraulic fluids. It has low acute toxicity in feeding experiments, but has been implicated as a potential hormone mimetic.

Heather M. Stapleton is an American environmental organic chemist and exposure scientist. She is the Ronie-Richele Garcia-Johnson Distinguished Professor at Duke University's Nicholas School of the Environment. During her tenure at Duke, Stapleton focused her research on identifying and understanding the uses of flame retardant chemicals in consumer products and evaluating the health impacts of exposures to those chemicals.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

<span class="mw-page-title-main">Tris(2-ethylhexyl) phosphate</span> Chemical compound

Tris(2-ethylhexyl)phosphate (TEHP) is an organic chemical compound in the organophosphate group. It is a triakylphosphate.

References

  1. ↑ "Tris(1,3-dichloro-2-propyl)phosphate". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 Gold MD, Blum A, Ames BN (May 1978). "Another flame retardant, tris-(1,3-dichloro-2-propyl)-phosphate, and its expected metabolites are mutagens". Science. 200 (4343): 785–7. Bibcode:1978Sci...200..785G. doi:10.1126/science.347576. PMID   347576.
  3. 1 2 3 Carignan CC, McClean MD, Cooper EM, Watkins DJ, Fraser AJ, Heiger-Bernays W, Stapleton HM, Webster TF (May 2013). "Predictors of tris(1,3-dichloro-2-propyl) phosphate metabolite in the urine of office workers". Environment International. 55: 56–61. Bibcode:2013EnInt..55...56C. doi:10.1016/j.envint.2013.02.004. PMC   3666188 . PMID   23523854.
  4. ↑ Stapleton HM, Klosterhaus S, Eagle S, Fuh J, Meeker JD, Blum A, Webster TF (October 2009). "Detection of organophosphate flame retardants in furniture foam and U.S. house dust". Environmental Science & Technology. 43 (19): 7490–5. Bibcode:2009EnST...43.7490S. doi:10.1021/es9014019. PMC   2782704 . PMID   19848166.
  5. 1 2 Stapleton HM, Klosterhaus S, Keller A, Ferguson PL, van Bergen S, Cooper E, Webster TF, Blum A (June 2011). "Identification of flame retardants in polyurethane foam collected from baby products". Environmental Science & Technology. 45 (12): 5323–31. Bibcode:2011EnST...45.5323S. doi:10.1021/es2007462. PMC   3113369 . PMID   21591615.
  6. ↑ Stapleton HM, Sharma S, Getzinger G, Ferguson PL, Gabriel M, Webster TF, Blum A (December 2012). "Novel and high volume use flame retardants in US couches reflective of the 2005 PentaBDE phase out". Environmental Science & Technology. 46 (24): 13432–9. Bibcode:2012EnST...4613432S. doi:10.1021/es303471d. PMC   3525014 . PMID   23186002.
  7. 1 2 3 4 5 6 7 van der Veen I, de Boer J (August 2012). "Phosphorus flame retardants: properties, production, environmental occurrence, toxicity and analysis". Chemosphere. 88 (10): 1119–53. Bibcode:2012Chmsp..88.1119V. doi:10.1016/j.chemosphere.2012.03.067. PMID   22537891.
  8. ↑ Martin A (17 May 2011). "Chemical Suspected in Cancer Is in Baby Products". The New York Times.
  9. ↑ Keller AS, Raju NP, Webster TF, Stapleton HM (February 2014). "Flame Retardant Applications in Camping Tents and Potential Exposure". Environmental Science & Technology Letters. 1 (2): 152–155. Bibcode:2014EnSTL...1..152K. doi:10.1021/ez400185y. PMC   3958138 . PMID   24804279.
  10. ↑ Bergh C, Torgrip R, Emenius G, Ostman C (February 2011). "Organophosphate and phthalate esters in air and settled dust - a multi-location indoor study". Indoor Air. 21 (1): 67–76. Bibcode:2011InAir..21...67B. doi:10.1111/j.1600-0668.2010.00684.x. PMID   21054550.
  11. ↑ Kanazawa A, Saito I, Araki A, Takeda M, Ma M, Saijo Y, Kishi R (February 2010). "Association between indoor exposure to semi-volatile organic compounds and building-related symptoms among the occupants of residential dwellings". Indoor Air. 20 (1): 72–84. Bibcode:2010InAir..20...72K. doi:10.1111/j.1600-0668.2009.00629.x. hdl: 2115/87324 . PMID   20028434.
  12. ↑ Marklund A, Andersson B, Haglund P (December 2003). "Screening of organophosphorus compounds and their distribution in various indoor environments". Chemosphere. 53 (9): 1137–46. Bibcode:2003Chmsp..53.1137M. doi:10.1016/S0045-6535(03)00666-0. PMID   14512118.
  13. ↑ Marklund A, Andersson B, Haglund P (October 2005). "Organophosphorus flame retardants and plasticizers in Swedish sewage treatment plants". Environmental Science & Technology. 39 (19): 7423–9. Bibcode:2005EnST...39.7423M. doi:10.1021/es051013l. PMID   16245811.
  14. ↑ Staaf T, Ostman C (September 2005). "Organophosphate triesters in indoor environments". Journal of Environmental Monitoring. 7 (9): 883–7. doi:10.1039/b506631j. PMID   16121268.
  15. ↑ Andresen JA, Grundmann A, Bester K (October 2004). "Organophosphorus flame retardants and plasticisers in surface waters". The Science of the Total Environment. 332 (1–3): 155–66. Bibcode:2004ScTEn.332..155A. doi:10.1016/j.scitotenv.2004.04.021. PMID   15336899.
  16. ↑ Regnery J, Püttmann W (February 2010). "Seasonal fluctuations of organophosphate concentrations in precipitation and storm water runoff". Chemosphere. 78 (8): 958–64. Bibcode:2010Chmsp..78..958R. doi:10.1016/j.chemosphere.2009.12.027. PMID   20074776.
  17. ↑ Minegishi KI, Kurebayashi H, Nambaru S, Morimoto L, Takahashi T, Yamaha T (1988). "Comparative studies on absorption, distribution, and excretion of flame retardants halogenated alkyl phosphate in rats". Eisei Kagaku. 34 (2): 102–114. doi: 10.1248/jhs1956.34.102 .
  18. ↑ Nomeir AA, Kato S, Matthews HB (March 1981). "The metabolism and disposition of tris(1,3-dichloro-2-propyl) phosphate (Fyrol FR-2) in the rat". Toxicology and Applied Pharmacology. 57 (3): 401–13. doi:10.1016/0041-008X(81)90238-6. PMID   7222047.
  19. ↑ Child-specific exposure factors handbook. United States Environmental Protection Agency. September 2008.
  20. ↑ Hudec T, Thean J, Kuehl D, Dougherty RC (February 1981). "Tris(dichloropropyl)phosphate, a mutagenic flame retardant: frequent cocurrence in human seminal plasma". Science. 211 (4485): 951–2. Bibcode:1981Sci...211..951H. doi:10.1126/science.7466368. PMID   7466368.
  21. ↑ LeBel GL, Williams DT, Berard D (August 1989). "Triaryl/alkyl phosphate residues in human adipose autopsy samples from six Ontario municipalities". Bulletin of Environmental Contamination and Toxicology. 43 (2): 225–30. Bibcode:1989BuECT..43..225L. doi:10.1007/BF01701752. PMID   2775890. S2CID   30730887.
  22. ↑ Sundkvist AM, Olofsson U, Haglund P (April 2010). "Organophosphorus flame retardants and plasticizers in marine and fresh water biota and in human milk". Journal of Environmental Monitoring. 12 (4): 943–51. doi:10.1039/b921910b. PMID   20383376.
  23. ↑ Cooper EM, Covaci A, van Nuijs AL, Webster TF, Stapleton HM (October 2011). "Analysis of the flame retardant metabolites bis(1,3-dichloro-2-propyl) phosphate (BDCPP) and diphenyl phosphate (DPP) in urine using liquid chromatography-tandem mass spectrometry". Analytical and Bioanalytical Chemistry. 401 (7): 2123–32. doi:10.1007/s00216-011-5294-7. PMC   3718013 . PMID   21830137.
  24. ↑ Meeker JD, Cooper EM, Stapleton HM, Hauser R (May 2013). "Urinary metabolites of organophosphate flame retardants: temporal variability and correlations with house dust concentrations". Environmental Health Perspectives. 121 (5): 580–5. doi:10.1289/ehp.1205907. PMC   3673195 . PMID   23461877.
  25. ↑ Eaton DL, Daroff RB, Autrup H, Bridges J, Buffler P, Costa LG, Coyle J, McKhann G, Mobley WC, Nadel L, Neubert D, Schulte-Hermann R, Spencer PS (2008). "Review of the toxicology of chlorpyrifos with an emphasis on human exposure and neurodevelopment". Critical Reviews in Toxicology. 38 Suppl 2 (s2): 1–125. doi:10.1080/10408440802272158. PMID   18726789. S2CID   84162223.
  26. ↑ Eldefrawi AT, Mansour NA, Brattsten LB, Ahrens VD, Lisk DJ (June 1977). "Further toxicologic studies with commercial and candidate flame retardant chemicals. Part II". Bulletin of Environmental Contamination and Toxicology. 17 (6): 720–6. Bibcode:1977BuECT..17..720E. doi:10.1007/BF01685960. PMID   880389. S2CID   31364047.
  27. ↑ Freudenthal RI, Henrich RT (2000). "Chronic toxicity and carcinogenic potential of tris-(1, 3-dichloro-2-propyl) phosphate in Sprague-Dawley rat". International Journal of Toxicology. 19 (13674): 119–125. doi:10.1080/109158100224926. S2CID   93824913.
  28. ↑ "Proposition 65 in Plain Language!". California Office of Environmental Health Hazard Assessment. 2013. Retrieved 2014-06-12.
  29. ↑ Meeker JD, Stapleton HM (March 2010). "House dust concentrations of organophosphate flame retardants in relation to hormone levels and semen quality parameters". Environmental Health Perspectives. 118 (3): 318–23. doi:10.1289/ehp.0901332. PMC   2854757 . PMID   20194068.
  30. 1 2 Farhat A, Crump D, Chiu S, Williams KL, Letcher RJ, Gauthier LT, Kennedy SW (July 2013). "In Ovo effects of two organophosphate flame retardants--TCPP and TDCPP--on pipping success, development, mRNA expression, and thyroid hormone levels in chicken embryos". Toxicological Sciences. 134 (1): 92–102. doi: 10.1093/toxsci/kft100 . PMID   23629516.
  31. ↑ McGee SP, Cooper EM, Stapleton HM, Volz DC (November 2012). "Early zebrafish embryogenesis is susceptible to developmental TDCPP exposure". Environmental Health Perspectives. 120 (11): 1585–91. doi:10.1289/ehp.1205316. PMC   3556627 . PMID   23017583.
  32. ↑ Dasgupta S, Cheng V, Vliet SM, Mitchell CA, Volz DC (September 2018). "Tris(1,3-dichloro-2-propyl) Phosphate Exposure During the Early-Blastula Stage Alters the Normal Trajectory of Zebrafish Embryogenesis". Environmental Science & Technology. 52 (18): 10820–10828. Bibcode:2018EnST...5210820D. doi:10.1021/acs.est.8b03730. PMC   6169527 . PMID   30157643.
  33. ↑ Dasgupta S, Vliet SM, Kupsco A, Leet JK, Altomare D, Volz DC (2017-12-14). "Tris(1,3-dichloro-2-propyl) phosphate disrupts dorsoventral patterning in zebrafish embryos". PeerJ. 5: e4156. doi: 10.7717/peerj.4156 . PMC   5733366 . PMID   29259843.
  34. ↑ Dishaw LV, Powers CM, Ryde IT, Roberts SC, Seidler FJ, Slotkin TA, Stapleton HM (November 2011). "Is the PentaBDE replacement, tris (1,3-dichloro-2-propyl) phosphate (TDCPP), a developmental neurotoxicant? Studies in PC12 cells". Toxicology and Applied Pharmacology. 256 (3): 281–9. doi:10.1016/j.taap.2011.01.005. PMC   3089808 . PMID   21255595.
  35. ↑ Bondy SC, Campbell A (September 2005). "Developmental neurotoxicology" (PDF). Journal of Neuroscience Research. 81 (5): 605–12. doi:10.1002/jnr.20589. PMID   16035107. S2CID   39938045.
  36. ↑ Liu X, Ji K, Choi K (June 2012). "Endocrine disruption potentials of organophosphate flame retardants and related mechanisms in H295R and MVLN cell lines and in zebrafish". Aquatic Toxicology. 114–115: 173–81. Bibcode:2012AqTox.114..173L. doi:10.1016/j.aquatox.2012.02.019. PMID   22446829.
  37. 1 2 Wang Q, Liang K, Liu J, Yang L, Guo Y, Liu C, Zhou B (January 2013). "Exposure of zebrafish embryos/larvae to TDCPP alters concentrations of thyroid hormones and transcriptions of genes involved in the hypothalamic-pituitary-thyroid axis". Aquatic Toxicology. 126: 207–13. Bibcode:2013AqTox.126..207W. doi:10.1016/j.aquatox.2012.11.009. PMID   23220413.
  38. ↑ Gilbert ME, Rovet J, Chen Z, Koibuchi N (August 2012). "Developmental thyroid hormone disruption: prevalence, environmental contaminants and neurodevelopmental consequences". Neurotoxicology. 33 (4): 842–52. doi:10.1016/j.neuro.2011.11.005. PMID   22138353.
  39. ↑ Zoeller TR, Dowling AL, Herzig CT, Iannacone EA, Gauger KJ, Bansal R (June 2002). "Thyroid hormone, brain development, and the environment". Environmental Health Perspectives. 110 Suppl 3 (April): 355–61. doi:10.1289/ehp.02110s3355. PMC   1241183 . PMID   12060829.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.