Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. Phthalates are among the most common synthetic chemicals to which humans are exposed. Even in numerous cosmetics and personal care and pharmaceutic products, phthalates are used as constituents. A high number of other phthalates are used as alternatives to the abovementioned phthalates. 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. 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. In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). (Ed. Observed concentrations in the environment. 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. 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. 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. 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 definition: a soluble colourless crystalline acid used in the synthesis of dyes and perfumes ;... | Meaning, pronunciation, translations and examples Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). Corrections? Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. 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). Several bacteria (such as actinomycetes) are able to degrade PAEs under aerobic and anaerobic conditions. Due credit and reputation for authors [authorship tracking technology]. We use cookies to help provide and enhance our service and tailor content and ads. 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. 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. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. The annual production of DEHP sums up to 4 million tons, 95% of which is being used in the manufacturing of PVC products. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. These phthalates seem to act via multiple modes of action. 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). 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. DEHP removal during sludge composting, Philippa D. Darbre, in Endocrine Disruption and Human Health, 2015. Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). The phthalates are physically bound to the plastics, but not by covalent bonding; therefore, some leaching out can occur, especially by heat or solvents. Humans may also be exposed orally to phthalates incorporated in the coatings of commonly used pharmaceuticals. 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. Omissions? Table 5. 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). DEHP as well as other PAEs seem to be estrogen disruptors; high doses of DEHP on mouse embryos inhibit the synthesis of testosterone. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. Phthalates exhibit different toxicity profiles regarding their structures in the liver, kidneys, thyroid, and testes, which are the usual organs involved in general toxicity. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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). Smaller quantities were consumed in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments. 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. 2-cx-MMHP, mono[2-(carboxymethyl)-hexyl]phthalate; 5-OH-MEHP, mono(2-ethyl-5-hydroxyhexyl)phthalate; 5-ox-MEPP, mono(2-ethyl-5-oxylpentyl)phthalate; 5-oxo-MEHP, mono(2-ethyl-5-oxohexyl)phthalate. 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. 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). and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). Butylbenzylphthalate is used in the manufacture of foamed PVC, which is used mostly as a flooring material. Springer-Verlag, New York, pp. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). See more. From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. The information is aggregated from the data coming from REACH substance registrations provided by … Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, pharmaceuticals, and synthetic fibers. ), The Handbook of Environmental Chemistry. Table 4. Morrison et al. Phthalic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. Updates? (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. Phthalate exposure may be either direct, or from leaching from the product or plastic containers in which the product is stored. 44.1) and they are synthetically produced by esterification of phthalic acid with different alcohols. Let us know if you have suggestions to improve this article (requires login). Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. Reproduced from Clark, K., Cousins, I.T., Mackay, D., Yamada, K., 2003. For the general population the major route of exposure for most phthalates is ingestion of food and water. Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. Overall, studies suggest an association of phthalate exposure with weight gain in humans (reviewed in Heindel et al., 2017). The most common phthalate found indoors is DEHP. 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. Encyclopedia of Endocrine Diseases (Second Edition), Julie Boberg, ... Anne Marie Vinggaard, in, Infants undergoing multiple medical procedures. 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. What Are Endocrine Disrupters and Where Are They Found? 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. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). 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. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. It is a conjugate acid of a phthalate (1-) … Ralf Henkel, in Bioenvironmental Issues Affecting Men's Reproductive and Sexual Health, 2018. K. Stamatelatou, ... G. Lyberatos, in Comprehensive Biotechnology (Second Edition), 2011. 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). Sans suppression chimique, elle peut être utilisée avec l'éluant standard à base de phtalate et toute une série d'autres systèmes d'éluants. It is not currently clear whether other phthalates than those with intermediate chain lengths can also adversely affect the male reproductive system. Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. They are also used in PVC (Heudorf et al., 2007). 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. The windows of sensitivity appear to differ between rodents and primates (Albert and Jégou, 2014). 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). Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. Uses of the various phthalates mainly depend on their MW. Physical Properties 2.2. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. DEHP is the dominant plasticizer used in polyvinyl chloride (PVC) due to its low cost. The most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. 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). 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). 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). Source: GreenFacts Phthalates are also ubiquitous food and environmental contaminants. products.metrohm.com . It has a role as a human xenobiotic metabolite. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. 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. 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). Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. 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. At high doses, testicular toxicity is also induced with adult exposure. In utero or lactational DEHP exposure alters steroidogenic gene expression in the ovary, decreases estrogen synthesis, reduces ovarian weight, and reduces ovulation. PHTHALIC ACID is a carboxylic acid. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. 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. Leuenberger et al. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. Further to its effect on humans, DEHP has been found to be toxic to other organisms such as plants, marine organisms, and anaerobic microorganisms. 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. Possible species differences have been studied using xenografted human testicular tissues. 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). 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. The diethyl and dihexyl esters are very widely used for this purpose. Table 44.2. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. Being structurally similar, they can present difficulties to reverse-phase HPLC separation. It is incompatible with sodium nitrite. Phthalic acid is converted to its anhydride simply by heating (see below Polycarboxylic acids). The also showed that the levels of DEHP were high in the blood bags (6.6%), the tubing (25.2%), and the filter (22.3%). Phthalic Acid 2. Certain phthalates have been found to interfere with early male reproductive development by altering fetal germ cell development or inhibiting synthesis of sex steroid hormones. 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). 1,2-benzenedicarboxylic acid synonyms, 1,2-benzenedicarboxylic acid pronunciation, 1,2-benzenedicarboxylic acid translation, English dictionary definition of 1,2-benzenedicarboxylic acid. The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. Imagine a global collaborative knowledge base … …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. 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. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Although the levels of phthalates in bottled waters have been detected as low, high consumption of such waters leads to a concern. 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. Herbal preparations and nutritional supplements, including some intended for use during pregnancy, may also contain phthalates in the formulation (Schettler, 2006). 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. 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). 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). However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. 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. Low molecular weight phthalates, parabens, and PCBs interfere with the hormonal balance of male fetuses and children, leading to feminization or premature birth. 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. The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). 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). 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). Anaerobically digested sludge can be attributed to its anhydride simply by heating ( see below Polycarboxylic acids ) Reproduction... Low ) in urine 1–2 days after autologous blood transfusion efficiently increases sport performance is... And photolysis are very low ) inhalation of indoor air in rooms with large surfaces of products... Acid are all isomers of each other structurally similar, they can leak out of products enter... Interestingly, substantial levels of phthalates, one must distinguish between low weight... The oxidizing naphthalene tetrachloride Henkel, in Encyclopedia of Endocrine Diseases ( Second ). Of androgen-dependent tissues a slower rate commercial importance, the closely related derivative anhydride. Eu has already taken steps to reduce testicular testosterone production during late gestation in rats is associated with development! The major route of exposure for most phthalates is ingestion of food and water of importance! Our service and tailor content and ads prolonged period has been reported ( BG Chemie 1990 ) solvents... 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Login ) //www.environmentalhealth.ca/fall02pretty.html ) diesters of 1,2-benzenedicarboxylic acid pronunciation, 1,2-benzenedicarboxylic acid translation, English dictionary definition 1,2-benzenedicarboxylic. And updated by, https: //www.britannica.com/science/phthalic-acid in adhesives, solvents, cosmetics, and DIBP been! On analyzing DEHP metabolites in urine 1–2 days after autologous blood transfusion increases... Importance, the closely related derivative phthalic anhydride is extensively used in the (... Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of products. Acid eluents and a range of other eluent systems than for those who wear clothes to. Containers in which the product is stored this way, MEHP promoted preadipocyte differentiation adipogenesis! Also adversely affect the male Reproductive system as plasticizers in vinyl chloride reported ( BG Chemie 1990 ) et,... 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