Current methods for detecting this doping focus on analyzing DEHP metabolites, which enter the stored blood from blood bags. phthalic acid: ChEBI ID CHEBI:29069: Definition A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. PAEs with long alkyl chain (such as DEHP) are mineralized at a slower rate. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). 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 is produced in final stage metabolites of phthalic acid esters. Table 5. For the general population the major route of exposure for most phthalates is ingestion of food and water. We use cookies to help provide and enhance our service and tailor content and ads. Phthalates are among the most common synthetic chemicals to which humans are exposed. 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). 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). 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). Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. The EU has already taken steps to reduce the use of certain phthalates (such as 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. Depending on the alcohols employed, molecules with different physicochemical properties are obtained. This exposure route is suggested to be of limited importance for adults. Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. 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). It has a role as a human xenobiotic metabolite. These phthalates seem to act via multiple modes of action. Herbal preparations and nutritional supplements, including some intended for use during pregnancy, may also contain phthalates in the formulation (Schettler, 2006). However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. (NTP, 1992). …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. Di(2-ethylhexyl) phthalate (DEHP) and metabolites used to estimate DEHP exposure. 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. Encyclopedia of Endocrine Diseases (Second Edition), Julie Boberg, ... Anne Marie Vinggaard, in, Infants undergoing multiple medical procedures. Dimethyl Phthalate is useful as an insect repellent. 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). Hydrolysis of Phthalic Anhydride.png 3,123 × 1,248; 72 KB. 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. Reproduced from Clark, K., Cousins, I.T., Mackay, D., Yamada, K., 2003. Copyright © 2021 Elsevier B.V. or its licensors or contributors. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. 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. Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. At high doses, testicular toxicity is also induced with adult exposure. The diethyl and dihexyl esters are very widely used for this purpose. 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). Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. 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. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. 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). The mechanism by which phthalates interfere with thyroid function is not entirely understood. Imagine a global collaborative knowledge base … 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. Also of practical importance are the cyclic imide (phthalimide) and dichloranhydride (phthalyl chloride) of ortho-phthalic acid, as well as phthalylsulfathiazole (Ftalazol). Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. Ring in the new year with a Britannica Membership. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate 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. They are also used in PVC (Heudorf et al., 2007). (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. Animal studies have shown enhancement of NIS expression and iodide uptake but antagonism at the thyroid receptor (Gore et al., 2015). Springer-Verlag, New York, pp. Consequently, phthalates are found in human residential and occupational environments in high concentrations, both in air and in dust. 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. This compound reacts violently with nitric acid. 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. Together, these genes stimulate fatty acid uptake and TAG synthesis (Hao et al., 2012a). Without chemical suppression it can be used with normal phthalic acid eluents and a range of other eluent systems. 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). Table 44.2. Omissions? DEHP has been detected in higher concentration values than all the other phthalates in raw or treated sewage. Table 4. Surprisingly, enteric-coated pharmaceutical tablets and nutritional supplements to viscosity control agents also contain phthalates. 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. Phthalates are mainly used in gastrointestinal drug coatings to localize medication release. Corrections? Infants and young children (0.5–4 years of age) consume more calories per kg body weight (bw) and consume relatively more fatty foods compared with adults. Butylbenzylphthalate is used in the manufacture of foamed PVC, which is used mostly as a flooring material. Phthalic acid is an organic compound derived from benzene and used in the manufacture of dyes, perfumes, pharmaceuticals, and synthetic fibers. 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. 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 a conjugate acid of a phthalate (1-) … Safe alternatives such as glass or polyethylene plastics and phthalate-free labeled are highly recommended. 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 incompatible with sodium nitrite. Updates? 1,2-benzenedicarboxylic acid synonyms, 1,2-benzenedicarboxylic acid pronunciation, 1,2-benzenedicarboxylic acid translation, English dictionary definition of 1,2-benzenedicarboxylic acid. Due credit and reputation for authors [authorship tracking technology]. 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. Phthalates are also ubiquitous food and environmental contaminants. … DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. Phthalates are chemicals used as plasticizers and in adhesives, solvents, cosmetics, and other products. products.metrohm.com. The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. Uses of the various phthalates mainly depend on their MW. Morrison et al. This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. 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. 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). 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). In Sweden significantly higher DEHP levels in dust were found in homes of children with doctor-diagnosed asthma (Bornehag et al., 2004). It is an isomer of isophthalic acid and terephthalic acid. Overall, studies suggest an association of phthalate exposure with weight gain in humans (reviewed in Heindel et al., 2017). 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. This chemical is sensitive to exposure to extreme heat. 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). Phthalic Anhydride 2.1. Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. 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. Le catalyseur du type V.P.O. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Define 1,2-benzenedicarboxylic acid. In the evaluation of phthalates, one must distinguish between low molecular weight (DEHP, DBP, etc.) The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. Ralf Henkel, in Bioenvironmental Issues Affecting Men's Reproductive and Sexual Health, 2018. 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. Polyesters containing isophthalic acid are also used extensively in industrial coatings applications for home appliances, automobiles, aluminum siding, and metal office furniture. 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). 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. 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. 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. The world's first wiki where authorship really matters. It is claimed that phthalates are never employed in plastic food wraps marketing in the United States. 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 exhibit different toxicity profiles regarding their structures in the liver, kidneys, thyroid, and testes, which are the usual organs involved in general toxicity. 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. 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. 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). Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. 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. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. 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. 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 Concentration of DEHP in primary, secondary, dehydrated anaerobically digested, and composted sludge in samples taken from four sewage-treatment plants in Seville [7]. 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. Phthalate exposure may be either direct, or from leaching from the product or plastic containers in which the product is stored. 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 Handbook of Environmental Chemistry. Phthalates work by activating PPARs as well as causing antiandrogenic affects, both of which can lead to obesity (Kim and Park, 2014). Interestingly, substantial levels of DEHP were also found in blood bags labeled DEHP-free (Leuenberger et al., 2016). 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