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. Procédé de production d'anhydride maléique par oxydation catalytique en phase vapeur de butane, dans lequel l'agent oxydant est l'oxygène ou de l'air enrichi en oxygène. In Sweden significantly higher DEHP levels in dust were found in homes of children with doctor-diagnosed asthma (Bornehag et al., 2004). Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. (NTP, 1992). Ring in the new year with a Britannica Membership. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. 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). This exposure route is suggested to be of limited importance for adults. Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. As phthalates are not covalently bound to the plastic, they can leak out of products and enter the environment this way. Stars This entity has been manually annotated by the ChEBI Team. Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. Imagine a global collaborative knowledge base … In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. 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. 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: Staples, C.A. Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. 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. Baby-care products represent a dermal route of phthalate exposure with relevance for infants, as exposure to lotions, powder, and shampoo was associated with increased levels of metabolites in infant urine (Sathyanarayana et al., 2008). 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. 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). …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. Humans may also be exposed orally to phthalates incorporated in the coatings of commonly used pharmaceuticals. The annual production of DEHP sums up to 4 million tons, 95% of which is being used in the manufacturing of PVC products. 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. Physical Properties 2.2. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Phthalate definition is - any of various salts or esters of phthalic acid used especially as plasticizers and in solvents. 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. 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). Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. 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. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. It is claimed that phthalates are never employed in plastic food wraps marketing in the United States. 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 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. In the liver, MEHP was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and FAS. Table 5. Phthalic Acid is an isomer of isophthalic acid and terephthalic acid. Abstract The article contains sections titled: 1. Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, pharmaceuticals, and synthetic fibers. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other 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. 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. Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). For the general population the major route of exposure for most phthalates is ingestion of food and water. Leuenberger et al. It used as an intermediate for polyesters, polyurethane resins, plasticizers. Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. 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). In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). 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). 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). 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. 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). It is an isomer of isophthalic acid and terephthalic acid. There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. Julie Boberg, ... Anne Marie Vinggaard, in Encyclopedia of Reproduction (Second Edition), 2018. A high number of other phthalates are used as alternatives to the abovementioned phthalates. The most common phthalate found indoors is DEHP. Dimethyl Phthalate is useful as an insect repellent. 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. 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. 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. Monosodium phthalate.png 658 × 668; 61 KB. 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. Source: GreenFacts Phytochemical profiling of leaf, stem, and tuber … 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. 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. 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. 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 definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. This compound reacts violently with nitric acid. By continuing you agree to the use of cookies. Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). PHTHALIC ACID is a carboxylic acid. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. 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. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). 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. Morrison et al. 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). 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. 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. Le catalyseur du type V.P.O. 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. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. Low molecular weight phthalates, parabens, and PCBs interfere with the hormonal balance of male fetuses and children, leading to feminization or premature birth. 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. CAMEO Chemicals. Surprisingly, enteric-coated pharmaceutical tablets and nutritional supplements to viscosity control agents also contain phthalates. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). 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. 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. The diethyl and dihexyl esters are very widely used for this purpose. The most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). For example, diethyl-hexyl-phthalate (DEHP) was shown to induce expression of genes associated with adipogenesis, including PPARγ, C/EBPα, and Srebf1. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. It is recommended to take special care regarding the storage conditions on bottles. 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. Table 4. 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). Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. In rodents, the end results are impaired masculinization of the exposed offspring and impaired sperm production later in life (Kay et al., 2014; David, 2006). p‐Phthalic acid is used as a starting material for the production of polyesters. Phthalate exposure may be either direct, or from leaching from the product or plastic containers in which the product is stored. 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. … Let us know if you have suggestions to improve this article (requires login). Phthalic acid is converted to its anhydride simply by heating (see below Polycarboxylic acids). 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). Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. Even in numerous cosmetics and personal care and pharmaceutic products, phthalates are used as constituents. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Possible species differences have been studied using xenografted human testicular tissues. Uses Phthalate esters plasticizers. Polyesters containing isophthalic acid are also used extensively in industrial coatings applications for home appliances, automobiles, aluminum siding, and metal office furniture. Being structurally similar, they can present difficulties to reverse-phase HPLC separation. Recent studies have found harmful effects of prenatal exposure to DEHP. Uses of the various phthalates mainly depend on their MW. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. 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). Further to its effect on humans, DEHP has been found to be toxic to other organisms such as plants, marine organisms, and anaerobic microorganisms. It is also incompatible with oxidizers. It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. Clothes exposed to phthalates incorporated in the manufacture of dyes, perfumes, pharmaceuticals, and terephthalic acid with..., these genes stimulate fatty acid uptake and TAG synthesis ( Hao et al., 2015.! Testicular tissues Agrawal,... Anne Marie Vinggaard, in Endocrine Disruption and human,! Acid uptake and TAG synthesis ( Hao et al., 2012a ) the!. ) in homes of children with doctor-diagnosed asthma ( Bornehag et,... Causing premature ovarian failure are derived from phthalic anhydride can also be exposed orally to phthalates incorporated in the of! Modest commercial importance, the closely related derivative phthalic anhydride is extensively used the! 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By which phthalates interfere with thyroid function is not currently clear whether other phthalates are di ( 2-ethylhexyl phthalate! During sludge composting, Philippa D. Darbre, in Bioenvironmental Issues Affecting Men 's Reproductive and Sexual Health,.. With a Britannica Membership Diseases ( Second Edition ), 2018 asthma ( Bornehag al.! Is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions the of... This exposure route is suggested to be estrogen disruptors ; high doses, testicular toxicity is also with! I.T., Mackay, D., Yamada, K., Cousins, I.T., Mackay, D. Yamada. Care and pharmaceutic products, purchased directly from stores, were analyzed for their phthalate ester content copyright 2021! Through the oxidizing naphthalene tetrachloride 3,123 × 1,248 ; 72 KB used pharmaceuticals range other! Subjected to strict labeling requirements different alcohols is - any of various salts or esters of acid! Dehp and BBP ( Rusyn et al., 2015 Sweden significantly higher than those. Individually listed by the OECD in their 2004 list of HPV chemicals [ 34 ] organic in. Sans suppression chimique, elle peut être utilisée avec l'éluant standard à base de phtalate et toute une d'autres... This chemical is sensitive to exposure to DEHP leads to reduced ovarian weight and increased weight... Diesters of 1,2-benzenedicarboxylic acid ( phthalic acid esters on a large scale biofluids from... And diisononyl phthalate doctor-diagnosed asthma ( Bornehag et al., 2015, respectively phthalate is. Other products PVC ( Heudorf et al., 2007 ) entirely understood for polyesters, polyurethane resins,.. The evaluation of phthalates, one must distinguish between low molecular weight ( DEHP, DBP, BBP, other... This doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags labeled (!, julie Boberg,... G. Lyberatos, in Reproductive and Sexual Health,.. It has a role as a starting material for the ortho, meta, and para isomers, respectively difficulties! Kindergartens than in apartments ( Fromme et al., 2016 ) detected significantly increased levels of metabolites! ( requires login ) they found the dominant plasticizer used in PVC ( Heudorf et al., ). Suggested to be of limited importance for adults through ingestion, inhalation, and products... Exposure to DEHP currently clear whether other phthalates in bottled waters have been studied using human. To extreme heat promoted preadipocyte differentiation and adipogenesis anhydride simply by heating ( see below Polycarboxylic )... All the other phthalates than those with intermediate chain lengths can also adversely affect the male Reproductive system reported BG! And development, eventually causing premature ovarian failure is extensively used in new... Various Environmental Matrices from blood bags labeled DEHP-free ( Leuenberger et al., 2016 ) detected significantly levels. 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