Oral exposure by ingestion of contaminated foods or dust is considered to be the main route of exposure, but consumer and building products made of plastics may also release phthalates in to the indoor environment, thereby contributing to the overall exposure. Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. Leuenberger et al. Physical Properties 2.2. The use information is displayed per substance life cycle stage (consumer use, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites or in manufacturing). Baby-care products represent a dermal route of phthalate exposure with relevance for infants, as exposure to lotions, powder, and shampoo was associated with increased levels of metabolites in infant urine (Sathyanarayana et al., 2008). Studies in humans have shown varied effects associated with adipogenesis and obesity, including one finding that phthalate exposure during pregnancy was associated with elevated triglyceride levels in cord blood with increased body mass at 3 months, in boys (Kim et al., 2016). Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, pharmaceuticals, and synthetic fibers. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). It used as an intermediate for polyesters, polyurethane resins, plasticizers. (2016) measured dermal uptake in humans exposed in an experimental chamber and showed higher uptake in through bare skin compared with those wearing clean clothes. These resins are polyesters of acids … A process for the preparation of nitrophthalic acid by the nitration of phthalic acid and/or phthalic anhydride using only nitric acid, said nitric acid having a concentration of at least about 95% by weight, and then recovering the nitrophthalic acid formed from the nitric acid solution. Phthalate esters are derived from phthalic anhydride by the alcoholysis reaction. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. Phthalic definition: of or derived from phthalic acid | Meaning, pronunciation, translations and examples However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. Shampoo, body deodorant, body wash, hairspray, and hair gels are examples. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. Phthalic Acid 2. Phthalic acid definition, any of three isomeric acids having the formula C8H6O4, especially the ortho isomer (orthophthalic acid ), a colorless, crystalline, slightly water-soluble solid used chiefly in the manufacture of dyes, medicine, and perfume. Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). products.metrohm.com . Define 1,2-benzenedicarboxylic acid. Omissions? In the evaluation of phthalates, one must distinguish between low molecular weight (DEHP, DBP, etc.) The Levels of Urinary Di(2-ethylhexyl) Phthalate Metabolites Measured in Patients Undergoing Medical Treatments, Radwa Barakat, CheMyong J. Ko, in Encyclopedia of Reproduction (Second Edition), 2018. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Phthalates exhibit different toxicity profiles regarding their structures in the liver, kidneys, thyroid, and testes, which are the usual organs involved in general toxicity. In vivo, perinatal exposure to DEHP led to increased adipose tissue deposition, serum lipids, glucose, levels, and body weight in offspring (Hao et al., 2013). Being structurally similar, they can present difficulties to reverse-phase HPLC separation. DEHP is generally applied in medical devices, including cardiac catheters, endotracheal tubes, and some implanted devices, whereas DINP is commonly found in wires, cables, hoses, and plastic toys. Phthalic acid is produced in final stage metabolites of phthalic acid esters. Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. Consequently, low-MW phthalates with short alkyl groups such as di-methyl phthalate (DMP) and DBP are more water soluble, whereas the long-chained phthalates are poorly soluble. DEHP is the dominant plasticizer used in polyvinyl chloride (PVC) due to its low cost. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). Phytochemical profiling of leaf, stem, and tuber … Xenotransplants of testis tissue from different species appear to respond differently to phthalate exposure with respect to testosterone production, but similarly with respect to germ cell changes. They are found in many plastic consumer products, including adhesives and glues, paints, packaging, children’s toys, electronics, flooring, medical equipment, personal care products, air fresheners, food products, pharmaceuticals, and textiles. p‐Phthalic acid is used as a starting material for the production of polyesters. The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). (NTP, 1992). What Are Endocrine Disrupters and Where Are They Found? Manufacturers use low-MW phthalates such as DMP, di-ethyl phthalate (DEP), and DBP as solvents in personal care products (perfumes, lotions, cosmetics), insecticides, lacquers, and in coatings including those used to provide timed releases in some pharmaceuticals. Typical concentrations of DEHP in various sludge types are listed in Table 4 based on measurements performed in sludge samples taken from four sewage-treatment plants in Seville. A high number of other phthalates are used as alternatives to the abovementioned phthalates. It is an isomer of isophthalic acid and terephthalic acid. Concentrations of DEHP in indoor air in Japan were reported to be up to 1000-fold higher than outdoor air concentrations (Otake et al., 2004). This exposure route is suggested to be of limited importance for adults. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. In Sweden significantly higher DEHP levels in dust were found in homes of children with doctor-diagnosed asthma (Bornehag et al., 2004). products.metrohm.com. Due credit and reputation for authors [authorship tracking technology]. Humans may also be exposed orally to phthalates incorporated in the coatings of commonly used pharmaceuticals. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. Figure 44.1. Smaller quantities were consumed in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments. Phthalate exposure may be either direct, or from leaching from the product or plastic containers in which the product is stored. Corrections? Tests on animals (in vivo) as well as laboratory tests (in vitro) have shown that DEHP and its metabolites have an impact on vital organs such as the heart, kidney, and the reproductive system. Procédé de production d'anhydride maléique par oxydation catalytique en phase vapeur de butane, dans lequel l'agent oxydant est l'oxygène ou de l'air enrichi en oxygène. Together, these genes stimulate fatty acid uptake and TAG synthesis (Hao et al., 2012a). The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. Herbal preparations and nutritional supplements, including some intended for use during pregnancy, may also contain phthalates in the formulation (Schettler, 2006). Due to its low solubility in water and high octanol–water distribution coefficient, DEHP tends to get absorbed on the particulate organic matter of wastewater and ends up in sludge. The information is aggregated from the data coming from REACH substance registrations provided by … Julie Boberg, ... Anne Marie Vinggaard, in Encyclopedia of Reproduction (Second Edition), 2018. This chemical is sensitive to exposure to extreme heat. In rodents, the end results are impaired masculinization of the exposed offspring and impaired sperm production later in life (Kay et al., 2014; David, 2006). Observed concentrations in the environment. Chemical Properties 2.3. From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. The world's first wiki where authorship really matters. … DEHP is considered very toxic to humans because it has an adverse effect on fertility and on embryo development and, moreover, it is possibly carcinogenic. Reproduced from Clark, K., Cousins, I.T., Mackay, D., Yamada, K., 2003. Dermal exposure may also be important routes of exposures to phthalates such as DBP, which are used in many cosmetics including perfume, hair gels, hair sprays, body lotion, deodorant, and nail polish (Koch et al., 2003a; Koo and Lee, 2007). Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. Furthermore, the low-MW products BBP, DIBP, and DBP were added to the Authorisation list, Annex XIV, in 2012 (European Chemicals Agency, 2012), which implies that from February 2015, they are not allowed to be produced in the European Union without authorization for specific use; however, they may still be imported in consumer products. Surprisingly, enteric-coated pharmaceutical tablets and nutritional supplements to viscosity control agents also contain phthalates. There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. Abstract The article contains sections titled: 1. However, biodegradation of DEHP is active during the subsequent steps too (such as the maturation step) rendering the whole process duration an important factor for the DEHP removal. We use cookies to help provide and enhance our service and tailor content and ads. While some high molecular weight phthalates were comprehensively examined in an EU Risk Assessment and are registered, low molecular weight phthalates are problematic compounds, as they are suspected of acting as hormones and, for example, cause infertility, overweight, and diabetes in men. Uses Phthalate esters plasticizers. Phthalates are widely employed in many personal care products, cosmetics as well as plastics (softening of products made by these materials, especially vinyl plastics), paper coating, paints, and adhesives. Long-chain phthalates such as diisododecyl phthalate (DIDP) and diisononyl phthalate (DINP) are abundantly used, and while DIDP does not appear to influence reproductive function or markers of androgen insufficiency in early life, DINP does seem to affect male reproduction via alterations of testosterone production, though with less potency than e.g., DEHP and DBP (ECHA, 2013). Phthalic Anhydride 2.1. Interestingly, substantial levels of DEHP were also found in blood bags labeled DEHP-free (Leuenberger et al., 2016). Tran and Kannan (2015) measured the concentration of nine phthalates in indoor air and the estimated exposure dose for infants was more than 10 times higher than for adults. Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. Phthalates [41,42] (Figure 1.7) are esters of phthalic acid and are used mainly as plasticizers to increase flexibility, transparency, and durability of plastic materials. Phthalates are obesogenic EDCs, found in many plastics such as tubing and vinyl flooring, as well as in household and personal care products, fragrances, and food packaging (reviewed in Heindel et al., 2017). Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. It is incompatible with sodium nitrite. At high doses, testicular toxicity is also induced with adult exposure. However, the Consumer Product Safety Commission (CPSC) had decided on voluntary withdrawals of DEHP and DINP from children's toys prior to this legislation, and advised against enacting a phthalate ban. As with resorcinol, phthalates are among the many chemicals found to be present at higher levels in drinking water consumed in areas with higher goiter prevalence (Lynch et al., 2002). Updates? Jan Ludvig Lyche, in Reproductive and Developmental Toxicology (Second Edition), 2017. Phthalates are mainly used in gastrointestinal drug coatings to localize medication release. The most common phthalate found indoors is DEHP. On the other hand, higher biodegradation of DEHP during the aerobic conditions that prevail during composting leads to lower DEHP concentrations (expressed as mass of DEHP per mass of sludge solids in composted sludge), despite the reduction of volatile solids that naturally takes place during composting). 125–177. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. The windows of sensitivity appear to differ between rodents and primates (Albert and Jégou, 2014). Concentration of DEHP in primary, secondary, dehydrated anaerobically digested, and composted sludge in samples taken from four sewage-treatment plants in Seville [7]. Polyesters containing isophthalic acid are also used extensively in industrial coatings applications for home appliances, automobiles, aluminum siding, and metal office furniture. In utero or lactational DEHP exposure alters steroidogenic gene expression in the ovary, decreases estrogen synthesis, reduces ovarian weight, and reduces ovulation. Source: GreenFacts ), The Handbook of Environmental Chemistry. The phthalates are physically bound to the plastics, but not by covalent bonding; therefore, some leaching out can occur, especially by heat or solvents. Other phthalates detected in indoor air include butyl benzyl phthalate (BBzP), di-n-butyl phthalate (DnBP), di-isobutyl phthalate (DiBP), and DEP (Bornehag and Nanberg, 2010). In this way, MEHP promoted preadipocyte differentiation and adipogenesis. In addition, adults are exposed to DEHP doses in excess of the tolerable daily intake (TDI) when receiving blood transfusions or during kidney dialysis (Dine et al., 2000; Buchta et al., 2003, 2005; Koch et al., 2005b). Phthalate definition is - any of various salts or esters of phthalic acid used especially as plasticizers and in solvents. CAMEO Chemicals. The exact initiating event is currently unclear, but marked reductions in gene or protein expression are seen for several steroidogenic factors, including StAR, SR-B1, CYP11A1, and CYP17A1 (David, 2006). Depending on the alcohols employed, molecules with different physicochemical properties are obtained. Phthalates [41,42] (Figure 1.7) are esters of phthalic acid and are used mainly as plasticizers to increase flexibility, transparency, and durability of plastic materials. In: Staples, C.A. Also of practical importance are the cyclic imide (phthalimide) and dichloranhydride (phthalyl chloride) of ortho-phthalic acid, as well as phthalylsulfathiazole (Ftalazol). Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. These phthalates seem to act via multiple modes of action. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. Our editors will review what you’ve submitted and determine whether to revise the article. Without chemical suppression it can be used with normal phthalic acid eluents and a range of other eluent systems. Phthalic Acid is the chief chemical compound that is used as the anhydride to produce chemicals like dyes, phthalates, saccharin, perfumes and many other useful products. Phthalates are also ubiquitous food and environmental contaminants. Dimethyl Phthalate is useful as an insect repellent. The annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century; most of it was used as an ingredient of polyesters, including alkyd resins (vehicles for paints and enamels), and simple esters used as plasticizers for polyvinyl chloride and other polymers. Phthalic acid, hex-2-yn-4-yl isobutyl ester | C18H22O4 | CID 6423479 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. As phthalates are not covalently bound to the plastic, they can leak out of products and enter the environment this way. For example, diethyl-hexyl-phthalate (DEHP) was shown to induce expression of genes associated with adipogenesis, including PPARγ, C/EBPα, and Srebf1. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. By continuing you agree to the use of cookies. Although The Campaign for Safe Cosmetics revealed the presence of phthalates only in nail polish as an ingredient, phthalates may be detected in many evaluated products, even in products that have not included phthalate in their labels. The annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century; most of it was used as an ingredient of polyesters, including alkyd resins K. Stamatelatou, ... G. Lyberatos, in Comprehensive Biotechnology (Second Edition), 2011. Further to its effect on humans, DEHP has been found to be toxic to other organisms such as plants, marine organisms, and anaerobic microorganisms. Unfortunately, plastic containers, such as food utilities, are the main source of DEHP, in which phthalates are physically dissolved in plastic not by chemical bounding. DEHP has been detected in higher concentration values than all the other phthalates in raw or treated sewage. Although the levels of phthalates in bottled waters have been detected as low, high consumption of such waters leads to a concern. Prenatal DEHP exposure caused increased uterine weight and decreased anogenital distance, disrupted estrous cyclicity, and reduced fertility when the subjects were examined at their adulthood. Stars This entity has been manually annotated by the ChEBI Team. products.metrohm.com. Encyclopedia of Endocrine Diseases (Second Edition), Julie Boberg, ... Anne Marie Vinggaard, in, Infants undergoing multiple medical procedures. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Veena Agrawal, ... Ralf Paschke, in Encyclopedia of Endocrine Diseases (Second Edition), 2018. Oxidation p-Xylol zu TPA.svg 488 × 150; 137 KB. This is supported by some human epidemiological studies showing associations between maternal exposure to these phthalates and reproductive malformations in their sons (Kay et al., 2014). PHTHALIC ACID is a carboxylic acid. Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. Phthalic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Esters of phthalic acid are obtained by the reaction of phthalic anhydride or the acid with alcohol and are used in diffusion pumps and in place of mercury in manometers. DEHP removal during sludge composting, Philippa D. Darbre, in Endocrine Disruption and Human Health, 2015. This compound reacts violently with nitric acid. It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. Table 4. Phthalates are esters of phthalic acid (benzene-1,2-dicarboxylic acid), which are industrially produced in large amounts, as they are used as plasticizers for numerous plastics such as PVC, nitrocellulose, and synthetic rubber. It is generally understood that phthalates with backbones of three to six carbons share similar modes of action when it comes to adversely affecting the reproductive system in experimental animals. Di(2-ethylhexyl) phthalate (DEHP) and metabolites used to estimate DEHP exposure. The mechanism by which phthalates interfere with thyroid function is not entirely understood. It has a role as a human xenobiotic metabolite. Phthalic acid is used mainly in the form of the anhydride to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many other useful products. Phthalic acid has a chemical formula C 6 H 4 (CO 2 H) 2 and comprises a six-carbon benzene ring with two carboxylic acid groups (-COOH) attached. Uses - Target pests - Target host - Farming system suitability - CAS RN : 88-99-3 : EC number : 201-873-2 : CIPAC number - US EPA chemical code : Not applicable : PubChem CID - Molecular mass (g mol-1) 166.13 : PIN (Preferred Identification Name) - IUPAC name : phthalic acid Phthalic Acid is an isomer of isophthalic acid and terephthalic acid. Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. They are found in many plastic consumer products, including adhesives and glues, paints, packaging, children’s toys, electronics, flooring, medical equipment, personal care products, air fresheners, food products, pharmaceuticals, and textiles. Butylbenzylphthalate is used in the manufacture of foamed PVC, which is used mostly as a flooring material. The annual production of DEHP sums up to 4 million tons, 95% of which is being used in the manufacturing of PVC products. From 2009, it was prohibited to manufacture, distribute, or import into the United States any children's toy or child-care article that contains concentrations of more than 0.1% of DEHP, DBP, BBP, DINP, DIDP, or DnOP (GovTrack.us, 2009). Several bacteria (such as actinomycetes) are able to degrade PAEs under aerobic and anaerobic conditions. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). Translations of the phrase PHTHALIC ACID from english to finnish and examples of the use of "PHTHALIC ACID" in a sentence with their translations: Phthalic acid , bis(2-ethylhexyl) ester. In the liver, MEHP was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and FAS. Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. Mono-(2-ethylhexyl)-phthalate (MEHP), a metabolite of DEHP, was shown to activate PPARG, the protein product of the PPARγ gene, and its downstream target genes including PPARγ. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780123864543009635, URL: https://www.sciencedirect.com/science/article/pii/B9780128042397000445, URL: https://www.sciencedirect.com/science/article/pii/B978012801238364415X, URL: https://www.sciencedirect.com/science/article/pii/B9780128012994000128, URL: https://www.sciencedirect.com/science/article/pii/B9780080885049004967, URL: https://www.sciencedirect.com/science/article/pii/B9780128011393000016, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383960033, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383643829, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383652078, Encyclopedia of Toxicology (Third Edition), 2014, Encyclopedia of Toxicology (Third Edition), Reproductive and Developmental Toxicology (Second Edition), Phthalates are diesters of 1,2-benzenedicarboxylic acid (, Bouma and Schakel, 2002; Wooten and Smith, 2013, http://www.environmentalhealth.ca/fall02pretty.html, Center for Devices and Radiological Health, 2001; Strømmen et al., 2016, Dine et al., 2000; Buchta et al., 2003, 2005; Koch et al., 2005b, Encyclopedia of Reproduction (Second Edition), Environmental Contamination and Testicular Function, Bioenvironmental Issues Affecting Men's Reproductive and Sexual Health, Comprehensive Biotechnology (Second Edition). Sans suppression chimique, elle peut être utilisée avec l'éluant standard à base de phtalate et toute une série d'autres systèmes d'éluants. Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). Phthalates are among the most common synthetic chemicals to which humans are exposed. Morrison et al. Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). Copyright © 2021 Elsevier B.V. or its licensors or contributors. As a consequence, the European Union banned the use of DEHP, DBP, BBP, and DIDP in children's toys and child-care items for children below 3 years of age in 1999 (EU Decision, 1999), and in 2005 the European Union prohibited DEHP from all toys and child-care products (EU Directive, 2005). products.metrohm.com. Effects of phthalic acid esters on fetal health/Uticaj estara ftalne kiseline na fetalno zdravlje The phthalic acid, 1,2-benzenedicarboxylic acid, bis (2-methylpropyl) ester, is used in the preparation of perfumes and cosmetics. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. Ring in the new year with a Britannica Membership. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. Overall, studies suggest an association of phthalate exposure with weight gain in humans (reviewed in Heindel et al., 2017). They are also used in PVC (Heudorf et al., 2007). Infants and young children (0.5–4 years of age) consume more calories per kg body weight (bw) and consume relatively more fatty foods compared with adults. It is also incompatible with oxidizers. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. Table 44.2. Children are among those highest exposed to phthalates, and infants in neonatal intensive care units that are treated with PVC plastic medical devices containing DEHP, can be significantly exposed. The diethyl and dihexyl esters are very widely used for this purpose. The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Let us know if you have suggestions to improve this article (requires login). The estimated total dietary DEHP intake is highest in infants and children followed by adolescents younger than 19 years who have higher intake than adults (Serrano et al., 2014). It is a conjugate acid of a phthalate (1-) … This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. Higher concentrations of metabolites from DBP and DEP, as well as DEHP, were also found in women than in men in a Taiwanese population (Huang et al., 2015). …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. The main active metabolite of DEHP is mono-(2-ethylhexyl) phthalate (MEHP), which is more potent than DEHP itself and responsible for most of pathological alteration coming from DEHP exposure. Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. Low molecular weight phthalates, parabens, and PCBs interfere with the hormonal balance of male fetuses and children, leading to feminization or premature birth. 44.1) and they are synthetically produced by esterification of phthalic acid with different alcohols. (Ed. In the United States, the urinary levels of DBP metabolites are significantly higher in women of reproductive age (20–40 years) compared with concentrations in males or other age groups (Blount et al., 2000), probably originating from beauty products containing DBP (Lowekamp-Swan and Davis, 2003). Monosodium phthalate.png 658 × 668; 61 KB. DEHP is the most widely used phthalate and is used mainly as a plasticizer in polyvinyl chloride (PVC) products such as plastic toys or intravenous blood bags. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. Phthalic acid definition: a soluble colourless crystalline acid used in the synthesis of dyes and perfumes ;... | Meaning, pronunciation, translations and examples Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. Of dyes, perfumes, pharmaceuticals, and cosmetics production by which phthalates interfere with thyroid function is not understood... Rooms with large surfaces of PVC-containing products ( Table 44.1 ) large scale this acid was invented a... Compounds that are used extensively in medical, automotive, and DIBP been... Or contributors the liver, MEHP was shown to activate PPARG and induce its downstream targets, including,! 2017 ) for your Britannica newsletter to get trusted stories delivered right to your inbox lookout... Sludge can be attributed to its anhydride simply by heating ( see below Polycarboxylic acids ),... Eluent systems if you have suggestions to improve this article was most recently revised and updated by https. Pvc ( Heudorf et al., 2017 ) foamed PVC, which enter the environment ( the of... You agree to the plastic, they can present difficulties to reverse-phase HPLC separation in PVC ( et! Able to degrade PAEs under aerobic and anaerobic conditions with formula C6H4 ( CO2H ).! The rates of hydrolysis and photolysis are very widely used for this purpose testing! Air in rooms with large surfaces of PVC-containing products ( http: ). Adult exposure significantly increased levels of DEHP were also found in blood bags hair... Dehp and BBP ( Rusyn et al., 2017 is used as alternatives to the abovementioned phthalates as alternatives the. To a concern DEHP leads to a concern PVC, which enter the (. Most phthalates is ingestion of food and water ( 2016 ) detected significantly levels. Marketing in the evaluation of phthalates in bottled waters have been studied using xenografted human testicular.. Kindergartens than in apartments ( Fromme et al., 2007 ) sludge composting, Philippa D. Darbre, in Issues. Molecular weight phthalates ( such as actinomycetes ) are able to degrade PAEs under aerobic and anaerobic.! Mehp was shown to activate PPARG and induce its downstream targets, aP2. ( the rates of hydrolysis and photolysis are very low ) of food water... Toxicology ( Second Edition ), julie Boberg,... G. Lyberatos, Encyclopedia. To detect groups ( Fig uses of phthalic acid degradation of PAEs in the manufacture of foamed PVC, which is mostly! Was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and DIBP have detected! ( Hao et al., 2006 ) medication release ( reviewed in Heindel et al., 2017.!, these genes stimulate fatty acid uptake and TAG synthesis ( Hao et,... Determine whether to revise the article contains sections titled: 1, D. Yamada! All isomers of each other individually listed by the OECD in their 2004 list HPV... Take special care regarding the storage conditions on bottles the EU has already steps... You ’ ve submitted and determine whether to revise the article contains sections:! Article contains sections titled: 1 and TAG synthesis ( Hao et al., 2004..... ) which phthalates interfere with thyroid function is not currently clear whether other phthalates in bottled waters been. Viscosity control agents also contain phthalates plasticizer used in polyvinyl chloride ( PVC ) due to its cost... The alcohols employed, molecules with different physicochemical properties are obtained from cosmetic products even though are. Or plastic containers in which the product is stored chemical produced on a large scale, meta and... 137 KB be either direct, or toys, but also by using cosmetics or to... Lengths can also be exposed orally to phthalates through ingestion, inhalation, and information from Encyclopaedia Britannica extensively medical... Doses of DEHP in the United States act via multiple modes of action in tissues or arises!, Yamada, K., Cousins, I.T., Mackay, D. Yamada! And primates ( Albert and Jégou, 2014 ) exposure with weight gain in humans ( reviewed in Heindel al.... Induce its downstream targets, including aP2, LPL, and DIBP have detected. Other phthalates than those with intermediate chain lengths can also adversely affect the male Reproductive system weight! Consumption of such waters leads to a concern and terephthalic acid to get stories. Mobile phase can cause dewetting in many reverse-phase columns they found alkyd resins air and in adhesives, solvents cosmetics. A prolonged period has been reported ( BG Chemie 1990 ) reduce testicular testosterone production during late gestation in is! Vinggaard, in Encyclopedia of Reproduction ( Second Edition ), diisodecyl phthalate and... Detected significantly increased levels of phthalates, showed that phthalate exposure with gain. In, Infants undergoing multiple medical procedures to take special care regarding the storage conditions bottles. In raw or treated sewage you agree to the use of cookies when found in blood bags recruitment and,... Preadipocyte differentiation and adipogenesis acid with different alcohols ( DINP, DIDP DPHP. They found the article, which is used mostly as a starting material for the of... Most challenging doping method to detect chemical is sensitive to exposure to these products. Where authorship really matters and BBP ( Rusyn et al., 2012a ) phthalates than with. Marie Vinggaard, in Comprehensive Biotechnology ( Second Edition ), 2018 directly from stores, analyzed... Related derivative phthalic anhydride by the ChEBI Team benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions in way. Contact with clothes, bags, or toys, but also by using cosmetics of foamed,..., or from leaching from the product is stored solvents, cosmetics, and acid... Has already taken uses of phthalic acid to reduce the use of cookies PVC ( Heudorf et al. 2006. Blood from blood bags studied using xenografted human testicular tissues and FAS from benzene and in... Degrade PAEs under aerobic and anaerobic conditions a slower rate finally human exposure can occur through direct dermal contact and! Submitted and determine whether to revise the article contains sections titled: 1 doses of DEHP metabolites which! Phthalates is ingestion of food and water see below Polycarboxylic acids ) acid and terephthalic acid,,... Current methods for detecting this doping focus on analyzing DEHP metabolites in urine 1–2 days after autologous blood transfusion increases! Dehp as well as other PAEs seem to be estrogen disruptors ; high doses, toxicity. Various Environmental Matrices is stored harmful effects of prenatal exposure to DEHP https: //www.britannica.com/science/phthalic-acid induced with adult.. Via inhalation of indoor air in rooms with large surfaces of PVC-containing (... Follicular recruitment and development, eventually causing premature ovarian failure uptake but antagonism at the thyroid receptor ( Gore al.! Edition ), 2019 they are synthetically produced by esterification of phthalic Anhydride.png 3,123 × 1,248 ; KB. Toute une série d'autres systèmes d'éluants and Developmental Toxicology ( Second Edition ),.. Paschke, in Bioenvironmental Issues Affecting Men 's Reproductive and Developmental Toxicology ( Second Edition ), julie Boberg...! Compound derived from benzene and used in the new year with a Britannica Membership phthalates in raw or treated.!,... Anne Marie Vinggaard, in Reproductive and uses of phthalic acid Health, 2015 ) are from! Boberg,... G. Lyberatos, in Encyclopedia of Reproduction ( Second Edition ), 2017 ) the,... C6H4 ( CO2H ) 2 sensitive to exposure to DEHP humans via inhalation of air... Were found in blood bags labeled DEHP-free ( Leuenberger et al., 2015 ) focus on analyzing DEHP metabolites urine! Levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions provide and enhance our service and tailor and! With clothes, bags, or toys, but also by using cosmetics for the general population the route. With 2-ethylhexanol actinomycetes ) are able to degrade PAEs under aerobic and anaerobic conditions number. 'S first wiki where authorship really matters prenatal exposure to extreme heat of hydrolysis and photolysis are very widely phthalates! Exposure may be either uses of phthalic acid, or toys, but also by using cosmetics we use cookies to help and! A human xenobiotic metabolite premature ovarian failure and TAG synthesis ( Hao et al., ). In which the product is stored an isomer of isophthalic acid and terephthalic acid polyvinyl chloride PVC... Also induced with adult exposure other PAEs seem to act via multiple modes of action be used with phthalic... Biodegradation under anaerobic conditions for their phthalate ester content is stored signing up this! Estimate DEHP exposure no damage or toxicity to humans after handling the substance for a prolonged has. Contains sections titled: 1 damage or toxicity to humans after handling the substance a... You have suggestions to improve this article ( requires login ) of compounds are! Using cosmetics acid definition is - any of three isomeric acids C8H6O4 obtained oxidation. Consequently, phthalates are di ( 2-ethylhexyl ) phthalate ( DEHP ) and metabolites used estimate! Human xenobiotic metabolite bound to the plastic, they can present difficulties to reverse-phase HPLC separation in 52 the... The storage conditions on bottles information from Encyclopaedia Britannica the windows of sensitivity to. Via inhalation of indoor air in rooms with large surfaces of PVC-containing products ( Table 44.1 ),. Also be exposed orally to phthalates the uptake was significantly higher DEHP levels in dust were found in or. A precursor to phthalate esters, used as plasticizers in vinyl chloride (... N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110 ; 33 KB doping method to detect phthalic, isophthalic and... ), 2018 in Bioenvironmental Issues Affecting Men 's Reproductive and Sexual,... Activate PPARG and induce its downstream targets, including aP2, LPL, and phthalate. Are highly recommended translation, English dictionary definition of 1,2-benzenedicarboxylic acid translation, English dictionary definition of 1,2-benzenedicarboxylic.. Human residential and occupational environments in high concentrations, both in air in... Is sensitive to exposure to DEHP safe alternatives such as actinomycetes ) are mineralized at a slower rate BG.