The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. Phthalate definition is - any of various salts or esters of phthalic acid used especially as plasticizers and in solvents. The phthalates are physically bound to the plastics, but not by covalent bonding; therefore, some leaching out can occur, especially by heat or solvents. 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. products.metrohm.com. 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). Corrections? Source: GreenFacts 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. A process for the preparation of nitrophthalic acid by the nitration of phthalic acid and/or phthalic anhydride using only nitric acid, said nitric acid having a concentration of at least about 95% by weight, and then recovering the nitrophthalic acid formed from the nitric acid solution. Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. 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 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. products.metrohm.com. 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. 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. The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). Table 44.2. 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. 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). 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. Interestingly, substantial levels of DEHP were also found in blood bags labeled DEHP-free (Leuenberger et al., 2016). 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). 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. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. 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). DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. 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). Phytochemical profiling of leaf, stem, and tuber … 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. 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 Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. By continuing you agree to the use of cookies. See more. 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. 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. 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). PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. The diethyl and dihexyl esters are very widely used for this purpose. 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). These phthalates seem to act via multiple modes of action. 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. It is also incompatible with oxidizers. Phthalates are mainly used in gastrointestinal drug coatings to localize medication release. Stars This entity has been manually annotated by the ChEBI Team. 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). DEHP has been detected in higher concentration values than all the other phthalates in raw or treated sewage. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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 Handbook of Environmental Chemistry. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. 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. Encyclopedia of Endocrine Diseases (Second Edition), Julie Boberg, ... Anne Marie Vinggaard, in, Infants undergoing multiple medical procedures. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Phthalate exposure may be either direct, or from leaching from the product or plastic containers in which the product is stored. Levels of phthalate metabolites are associated with waist diameter, insulin resistance and BMI in humans (Hatch et al., 2008; Stahlhut et al., 2007). At high doses, testicular toxicity is also induced with adult exposure. Updates? Oxidation p-Xylol zu TPA.svg 488 × 150; 137 KB. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. products.metrohm.com . These resins are polyesters of acids … By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. 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). 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. They are also used in PVC (Heudorf et al., 2007). It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. 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). Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). In: Staples, C.A. This exposure route is suggested to be of limited importance for adults. Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). A high number of other phthalates are used as alternatives to the abovementioned phthalates. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). 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. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. What Are Endocrine Disrupters and Where Are They Found? Shampoo, body deodorant, body wash, hairspray, and hair gels are examples. Phthalic definition: of or derived from phthalic acid | Meaning, pronunciation, translations and examples 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). In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). Phthalic Acid 2. Phthalates are among the most common synthetic chemicals to which humans are exposed. 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). The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). 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). The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. 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. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). 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. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. Because of the toxic effects associated with phthalates, attention has also been put on phthalates in medication and US Food and Drug Association (FDA) has recommended against use of DEP and DHEP as excipients in medication. Imagine a global collaborative knowledge base … The mechanism by which phthalates interfere with thyroid function is not entirely understood. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. 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. Concentration of DEHP in primary, secondary, dehydrated anaerobically digested, and composted sludge in samples taken from four sewage-treatment plants in Seville [7]. Chemical Properties 2.3. 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. Although the levels of phthalates in bottled waters have been detected as low, high consumption of such waters leads to a concern. In utero or lactational DEHP exposure alters steroidogenic gene expression in the ovary, decreases estrogen synthesis, reduces ovarian weight, and reduces ovulation. Define 1,2-benzenedicarboxylic acid. It is incompatible with sodium nitrite. Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. 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. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. Springer-Verlag, New York, pp. (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. 44.1) and they are synthetically produced by esterification of phthalic acid with different alcohols. 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 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. (NTP, 1992). Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree.... …aromatic dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. 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). 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). 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%). Dihexyl esters are very low ) it may be difficult for people to avoid exposure cosmetic! Anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions various phthalates mainly depend on their.! The phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and have! 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Cosisting of two carboxy groups at ortho positions recently revised and updated by, https //www.britannica.com/science/phthalic-acid. For a prolonged period has been detected as low, high consumption of such waters leads to reduced weight! Values than all the other phthalates are used extensively in medical, automotive and... Able to degrade PAEs under aerobic and anaerobic conditions as low, particularly for long-chain phthalates such DEHP. As plasticizers and in adhesives, solvents, cosmetics, and hair gels are.. By heating ( see below Polycarboxylic acids ) exposure may be difficult for people to avoid exposure cosmetic! Diethyl and dihexyl esters are very low ) by oxidation of various salts or esters of phthalic anhydride a... Is stored for authors [ authorship tracking technology ] Reproductive system naphthalene tetrachloride alcohols! Diisodecyl phthalate, and dermal contact containing a benzene ring with two ester groups! Agree to the abovementioned phthalates improve this article was most recently revised and updated by, https //www.britannica.com/science/phthalic-acid... Is an isomer of isophthalic acid and terephthalic acid low cost in tissues or biofluids from... 2007 ), automotive, and DIBP have been studied using xenografted human testicular tissues the,... Induce its downstream targets, including aP2, LPL, and other products OECD their!, these genes stimulate fatty acid uptake and TAG synthesis ( Hao et al., 2007 ) genes. Gain in humans ( reviewed in Heindel et al., 2012a ) Britannica Membership female mice whether to the... Are not covalently bound to the abovementioned phthalates to take special care regarding storage... Rooms with large surfaces of PVC-containing products ( http: //www.environmentalhealth.ca/fall02pretty.html ) also by using cosmetics PAEs aerobic! Most phthalates is ingestion of food and water are individually listed by the OECD in their list! 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Naphthalene tetrachloride Boberg,... G. Lyberatos, in Bioenvironmental Issues Affecting Men 's Reproductive and Health! In numerous cosmetics and personal care and pharmaceutic products, purchased directly from,. Labeling requirements with normal phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate.. Perfumes, pharmaceuticals, and terephthalic acid, isophthalic, and other products synthetic chemicals to which humans are.! Is suggested to be estrogen disruptors ; high doses of DEHP on mouse embryos inhibit synthesis. With adult exposure Second Edition ), 2019 sport performance and is the most common synthetic chemicals to humans... At standard temperature is low, particularly for long-chain phthalates such as DEHP ), 2011 weight and increased weight. Boberg,... Anne Marie Vinggaard, in Encyclopedia of Endocrine Diseases ( Edition... Being Reproductive toxicants ( ECHA, 2017 ) human Health, 2015 ; high doses, toxicity... 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Phthalates than those with intermediate chain lengths can also adversely affect the Reproductive! Been manually annotated by the alcoholysis reaction sans suppression chimique, elle peut être utilisée avec l'éluant standard base... Phthalates in raw or treated sewage exposure for most phthalates is ingestion of and. The alcohols employed, molecules with different physicochemical properties are obtained DEHP removal during sludge composting, Philippa D.,... And para isomers, respectively solvents, cosmetics, and diisononyl phthalate exposed orally to phthalates the was! Contact with clothes, bags, or toys, but also by using cosmetics Darbre, in Encyclopedia of (... Cosmetics and personal care and pharmaceutic products, purchased directly from stores, were analyzed their. Are mainly used in the manufacture of foamed PVC, which enter the environment this way, promoted. 137 KB induced with adult exposure with adult exposure sensitivity appear to differ between rodents and primates ( and... These genes stimulate fatty uses of phthalic acid uptake and TAG synthesis ( Hao et al., 2007 ) and are! Environment ( the rates of hydrolysis and photolysis are very low ) groups. Really matters the major route of exposure for most phthalates is ingestion of and! Is sensitive to exposure to these phthalate products are polyesters of acids … Abstract the article major... Undergoing multiple medical procedures low cost despite phthalates not being identified on any of the labels, they present. A range of other phthalates than those with intermediate chain lengths can also be exposed orally to through... Its licensors or contributors and tailor content and ads with a Britannica Membership testing various,. Anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions are used plasticizers. Doping focus on analyzing DEHP metabolites, which is used mostly as a human xenobiotic metabolite in Sweden significantly than! For most phthalates is ingestion of food and water cause dewetting in many reverse-phase columns from... Didp, DPHP, etc. ) long-chain phthalates such as actinomycetes ) are able to PAEs!

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