Several studies have also shown a positive association between urinary phthalates and serum TSH, although the overall strength of this association is weaker than that between urinary phthalates and serum thyroid hormone levels (Gore et al., 2015; Dirtu et al., 2013; Wu et al., 2013). 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). Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). This chemical is sensitive to exposure to extreme heat. Encyclopedia of Endocrine Diseases (Second Edition), Julie Boberg, ... Anne Marie Vinggaard, in, Infants undergoing multiple medical procedures. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, pharmaceuticals, and synthetic fibers. products.metrohm.com . Without chemical suppression it can be used with normal phthalic acid eluents and a range of other eluent systems. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. Smaller quantities were consumed in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments. Depending on the alcohols employed, molecules with different physicochemical properties are obtained. Table 5. 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). 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. Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. For phthalates with shorter or longer chain lengths, a few human epidemiological studies have found associations between prenatal exposures and anogenital distance, a marker of prenatal androgen insufficiency. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. Phthalic acid is converted to its anhydride simply by heating (see below Polycarboxylic acids). (Ed. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. 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. Omissions? Shampoo, body deodorant, body wash, hairspray, and hair gels are examples. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. 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. Jan Ludvig Lyche, in Reproductive and Developmental Toxicology (Second Edition), 2017. Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. Together, these genes stimulate fatty acid uptake and TAG synthesis (Hao et al., 2012a). DEHP as well as other PAEs seem to be estrogen disruptors; high doses of DEHP on mouse embryos inhibit the synthesis of testosterone. DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. 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). Several bacteria (such as actinomycetes) are able to degrade PAEs under aerobic and anaerobic conditions. 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). Veena Agrawal, ... Ralf Paschke, in Encyclopedia of Endocrine Diseases (Second Edition), 2018. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. The diethyl and dihexyl esters are very widely used for this purpose. p‐Phthalic acid is used as a starting material for the production of polyesters. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. At high doses, testicular toxicity is also induced with adult exposure. 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). Phthalic acid is produced in final stage metabolites of phthalic acid esters. 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). Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. 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. 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. Being structurally similar, they can present difficulties to reverse-phase HPLC separation. Ring in the new year with a Britannica Membership. 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. Possible species differences have been studied using xenografted human testicular tissues. Due credit and reputation for authors [authorship tracking technology]. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. It has a role as a human xenobiotic metabolite. The world's first wiki where authorship really matters. Recent studies have found harmful effects of prenatal exposure to DEHP. 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). In this way, MEHP promoted preadipocyte differentiation and adipogenesis. 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. ), The Handbook of Environmental Chemistry. 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. Source: GreenFacts 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. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. This exposure route is suggested to be of limited importance for adults. A high number of other phthalates are used as alternatives to the abovementioned phthalates. They are also used in PVC (Heudorf et al., 2007). 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). 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. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. 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. Uses of the various phthalates mainly depend on their MW. For example, diethyl-hexyl-phthalate (DEHP) was shown to induce expression of genes associated with adipogenesis, including PPARγ, C/EBPα, and Srebf1. Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. Updates? 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). DEHP removal during sludge composting, Philippa D. Darbre, in Endocrine Disruption and Human Health, 2015. Sans suppression chimique, elle peut être utilisée avec l'éluant standard à base de phtalate et toute une série d'autres systèmes d'éluants. Phthalic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Table 44.1. 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. Reproduced from Clark, K., Cousins, I.T., Mackay, D., Yamada, K., 2003. 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