Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). (NTP, 1992). The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. Veena Agrawal, ... Ralf Paschke, in Encyclopedia of Endocrine Diseases (Second Edition), 2018. products.metrohm.com . Define 1,2-benzenedicarboxylic acid. Julie Boberg, ... Anne Marie Vinggaard, in Encyclopedia of Reproduction (Second Edition), 2018. 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. The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). However, as a temperature increase favors DEHP biodegradation under aerobic conditions, sludge composting, as a thermophilic aerobic biological process, results in high DEHP removal efficiencies (Table 5). Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. (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. According to literature from the Pediatric Environmental Health Specialty Units program, some advice should be kept in mind to avoid releasing of phthalate from plastic containers: food/beverages and plastic clean wraps should not be heated at microwave in plastic containers and also plastics should not be placed in the dishwasher. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. Levels of phthalate metabolites are associated with waist diameter, insulin resistance and BMI in humans (Hatch et al., 2008; Stahlhut et al., 2007). 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. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. Our editors will review what you’ve submitted and determine whether to revise the article. Monosodium phthalate.png 658 × 668; 61 KB. 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). Phthalate definition is - any of various salts or esters of phthalic acid used especially as plasticizers and in solvents. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). In the case of phthalates used in medicaments, there is as yet no evidence of any damage in humans, but the European Medicines Agency suggests a restriction on the use, because animal experimental studies indicate damage by adequate doses. Concentration of DEHP in primary, secondary, dehydrated anaerobically digested, and composted sludge in samples taken from four sewage-treatment plants in Seville [7]. 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). Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). 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). Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. Table 44.1. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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). products.metrohm.com. 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). By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. 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. 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. The mechanism by which phthalates interfere with thyroid function is not entirely understood. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). 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. 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). The information is aggregated from the data coming from REACH substance registrations provided by … Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). However, the FDA has limited the advice to recommendation because the available data have only demonstrated association between exposure to phthalates and effects and not clear cause–effect relationship (Gallinger and Nguyen, 2013). Dimethyl Phthalate is useful as an insect repellent. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. Phthalates are among the most common synthetic chemicals to which humans are exposed. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. 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. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. Physical Properties 2.2. Shampoo, body deodorant, body wash, hairspray, and hair gels are examples. In mice, only minor changes in fetal steroid production are seen, whereas changes in early germ cell development are seen in both rats and mice (Albert and Jégou, 2014). … 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. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other products. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. By continuing you agree to the use of cookies. 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 It is claimed that phthalates are never employed in plastic food wraps marketing in the United States. 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. It has a role as a human xenobiotic metabolite. This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. Neonates may be exposed to high doses during blood transfusions and other life-saving procedures (Table 44.2) because medical devices for administration of medicines or nutrients may contain high levels of DEHP (20–40%) resulting in mono(2-ethylhexyl)phthalate (MEHP) concentrations several orders of magnitude higher than the general population (Center for Devices and Radiological Health, 2001; Strømmen et al., 2016). 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). 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. Due credit and reputation for authors [authorship tracking technology]. 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. In the evaluation of phthalates, one must distinguish between low molecular weight (DEHP, DBP, etc.) Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. Stars This entity has been manually annotated by the ChEBI Team. There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. Phthalic Acid 2. 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 definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. Phthalate esters are derived from phthalic anhydride by the alcoholysis reaction. Di(2-ethylhexyl) phthalate (DEHP) and metabolites used to estimate DEHP exposure. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). For example, diethyl-hexyl-phthalate (DEHP) was shown to induce expression of genes associated with adipogenesis, including PPARγ, C/EBPα, and Srebf1. Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. This means that even though the health risk associated with exposure to phthalates from plastics is likely reduced due to current regulations of the most toxic phthalates, the possible impact of other phthalates and alternative plasticizers on male reproductive function is not fully understood. 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). 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). It is a conjugate acid of a phthalate (1-) … Possible species differences have been studied using xenografted human testicular tissues. The world's first wiki where authorship really matters. Surprisingly, enteric-coated pharmaceutical tablets and nutritional supplements to viscosity control agents also contain phthalates. 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 most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. Several bacteria (such as actinomycetes) are able to degrade PAEs under aerobic and anaerobic conditions. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Further to its effect on humans, DEHP has been found to be toxic to other organisms such as plants, marine organisms, and anaerobic microorganisms. Updates? See more. Low molecular weight phthalates, parabens, and PCBs interfere with the hormonal balance of male fetuses and children, leading to feminization or premature birth. Springer-Verlag, New York, pp. The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). Figure 44.1. 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. 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). In the liver, MEHP was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and FAS. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. In addition to dietary exposure, oral intake of phthalates also occurs when children mouth, suck, or chew on toys containing phthalates (Bouma and Schakel, 2002; Wooten and Smith, 2013). From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. 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. However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. Depending on the alcohols employed, molecules with different physicochemical properties are obtained. 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. 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