Phthalates are among the most common synthetic chemicals to which humans are exposed. Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. 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). Ring in the new year with a Britannica Membership. 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. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). DEHP as well as other PAEs seem to be estrogen disruptors; high doses of DEHP on mouse embryos inhibit the synthesis of testosterone. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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. 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. The information is aggregated from the data coming from REACH substance registrations provided by … products.metrohm.com. 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). Animal studies have shown enhancement of NIS expression and iodide uptake but antagonism at the thyroid receptor (Gore et al., 2015). products.metrohm.com. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. This chemical is sensitive to exposure to extreme heat. Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. Copyright © 2021 Elsevier B.V. or its licensors or contributors. 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. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. 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. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). 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). 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. 125–177. Define 1,2-benzenedicarboxylic acid. Observed concentrations in the environment. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Monosodium phthalate.png 658 × 668; 61 KB. Our editors will review what you’ve submitted and determine whether to revise the article. (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. 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). …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). Being structurally similar, they can present difficulties to reverse-phase HPLC separation. These resins are polyesters of acids … Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. 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). 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. Physical Properties 2.2. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other products. 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. 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. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. The windows of sensitivity appear to differ between rodents and primates (Albert and Jégou, 2014). Phthalate esters are derived from phthalic anhydride by the alcoholysis reaction. Levels of phthalate metabolites are associated with waist diameter, insulin resistance and BMI in humans (Hatch et al., 2008; Stahlhut et al., 2007). 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. 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). Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. 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. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. 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. The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under 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). 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). No damage or toxicity to humans after handling the substance for a prolonged period has been reported (BG Chemie 1990). It is also incompatible with oxidizers. Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. 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. 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). Phthalates are mainly used in gastrointestinal drug coatings to localize medication release. What Are Endocrine Disrupters and Where Are They Found? Several bacteria (such as actinomycetes) are able to degrade PAEs under aerobic and anaerobic conditions. Interestingly, substantial levels of DEHP were also found in blood bags labeled DEHP-free (Leuenberger et al., 2016). Phthalate definition is - any of various salts or esters of phthalic acid used especially as plasticizers and in solvents. 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. 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. Phthalic Acid 2. Higher-MW DEHP, DINP, and DIDP are used in construction materials and numerous PVC products including clothing (footwear, raincoats), flooring and wall coverings, food packaging, children's products (toys, grip bumpers), and medical devices. 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). 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. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. 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. Due credit and reputation for authors [authorship tracking technology]. p‐Phthalic acid is used as a starting material for the production of polyesters. This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. 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. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. This exposure route is suggested to be of limited importance for adults. 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. Together, these genes stimulate fatty acid uptake and TAG synthesis (Hao et al., 2012a). DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. They are also used in PVC (Heudorf et al., 2007). It is not currently clear whether other phthalates than those with intermediate chain lengths can also adversely affect the male reproductive system. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). 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. Stars This entity has been manually annotated by the ChEBI Team. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. 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). 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