Veena Agrawal, ... Ralf Paschke, in Encyclopedia of Endocrine Diseases (Second Edition), 2018. 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. 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. Shampoo, body deodorant, body wash, hairspray, and hair gels are examples. 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). DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. 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. 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). It is claimed that phthalates are never employed in plastic food wraps marketing in the United States. Figure 44.1. 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). The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. 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). 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. Overall, studies suggest an association of phthalate exposure with weight gain in humans (reviewed in Heindel et al., 2017). Table 44.1. Monosodium phthalate.png 658 × 668; 61 KB. Morrison et al. This exposure route is suggested to be of limited importance for adults. Also of practical importance are the cyclic imide (phthalimide) and dichloranhydride (phthalyl chloride) of ortho-phthalic acid, as well as phthalylsulfathiazole (Ftalazol). 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). Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. products.metrohm.com. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). Abstract The article contains sections titled: 1. Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). 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). It used as an intermediate for polyesters, polyurethane resins, plasticizers. From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. 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. Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. 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). These phthalates seem to act via multiple modes of action. 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. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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. 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 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). 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). The phthalates are physically bound to the plastics, but not by covalent bonding; therefore, some leaching out can occur, especially by heat or solvents. 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. No damage or toxicity to humans after handling the substance for a prolonged period has been reported (BG Chemie 1990). (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. 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. Safe alternatives such as glass or polyethylene plastics and phthalate-free labeled are highly recommended. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). 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. Table 5. Herbal preparations and nutritional supplements, including some intended for use during pregnancy, may also contain phthalates in the formulation (Schettler, 2006). 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). It has a role as a human xenobiotic metabolite. Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for Springer-Verlag, New York, pp. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other products. Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. Phthalic definition: of or derived from phthalic acid | Meaning, pronunciation, translations and examples The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. In this way, MEHP promoted preadipocyte differentiation and adipogenesis. 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. (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. 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). Humans may also be exposed orally to phthalates incorporated in the coatings of commonly used pharmaceuticals. The most common phthalate found indoors is DEHP. By continuing you agree to the use of cookies. It is recommended to take special care regarding the storage conditions on bottles. 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. 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. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. 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. PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. (Ed. Stars This entity has been manually annotated by the ChEBI Team. At high doses, testicular toxicity is also induced with adult exposure. DEHP as well as other PAEs seem to be estrogen disruptors; high doses of DEHP on mouse embryos inhibit the synthesis of testosterone. Due credit and reputation for authors [authorship tracking technology]. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. Corrections? Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. K. Stamatelatou, ... G. Lyberatos, in Comprehensive Biotechnology (Second Edition), 2011. (NTP, 1992). … DEHP has been detected in higher concentration values than all the other phthalates in raw or treated sewage. Imagine a global collaborative knowledge base … Being structurally similar, they can present difficulties to reverse-phase HPLC separation. 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. Sans suppression chimique, elle peut être utilisée avec l'éluant standard à base de phtalate et toute une série d'autres systèmes d'éluants. products.metrohm.com. 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. 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. Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. 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. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. 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. This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. 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]. It is incompatible with sodium nitrite. It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. 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. Even in numerous cosmetics and personal care and pharmaceutic products, phthalates are used as constituents. Dimethyl Phthalate is useful as an insect repellent. Oxidation p-Xylol zu TPA.svg 488 × 150; 137 KB. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. 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 There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. Hydrazide of 3-Nitrophthalic acid.jpg 4,320 × 2,432; 1.91 MB. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. 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). Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. Jan Ludvig Lyche, in Reproductive and Developmental Toxicology (Second Edition), 2017. Possible species differences have been studied using xenografted human testicular tissues. Phthalates exhibit different toxicity profiles regarding their structures in the liver, kidneys, thyroid, and testes, which are the usual organs involved in general toxicity. 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). 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). 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). 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. 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). 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 Physical Properties 2.2. As phthalates are not covalently bound to the plastic, they can leak out of products and enter the environment this way. Our editors will review what you’ve submitted and determine whether to revise the article. 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). For example, diethyl-hexyl-phthalate (DEHP) was shown to induce expression of genes associated with adipogenesis, including PPARγ, C/EBPα, and Srebf1. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). 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. Fat and bags, or from leaching from the product or plastic in... Are used as an intermediate for polyesters, polyurethane resins, plasticizers many the! Synonyms uses of phthalic acid 1,2-benzenedicarboxylic acid pronunciation, 1,2-benzenedicarboxylic acid translation, English dictionary definition 1,2-benzenedicarboxylic! And water for the general population the major route of exposure for most phthalates is ingestion of food and.! Clothes exposed to phthalates incorporated in the anaerobically digested sludge can be used with normal phthalic ). 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