The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. 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. It used as an intermediate for polyesters, polyurethane resins, plasticizers. Autologous blood transfusion efficiently increases sport performance and is the most challenging doping method to detect. 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). 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. 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. (NTP, 1992). Monosodium phthalate.png 658 × 668; 61 KB. Smaller quantities were consumed in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments. 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. Phytochemical profiling of leaf, stem, and tuber … Corrections? It is also incompatible with oxidizers. Phthalic definition: of or derived from phthalic acid | Meaning, pronunciation, translations and examples The information is aggregated from the data coming from REACH substance registrations provided by … products.metrohm.com. 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). No damage or toxicity to humans after handling the substance for a prolonged period has been reported (BG Chemie 1990). Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. 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. Methods that require high organic concentrations in the mobile phase can cause dewetting in many reverse-phase columns. 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). By continuing you agree to the use of cookies. Phthalic Acid 2. Phthalic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. 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. A high number of other phthalates are used as alternatives to the abovementioned phthalates. 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 EU has already taken steps to reduce the use of certain phthalates (such as DEHP). (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. Sigal A. Willner, Bruce Blumberg, in Encyclopedia of Endocrine Diseases (Second Edition), 2019. 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). 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. This chemical is sensitive to exposure to extreme heat. 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. Springer-Verlag, New York, pp. Surprisingly, enteric-coated pharmaceutical tablets and nutritional supplements to viscosity control agents also contain phthalates. Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. 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. Phthalic acid is produced in final stage metabolites of phthalic acid esters. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. In utero or lactational DEHP exposure alters steroidogenic gene expression in the ovary, decreases estrogen synthesis, reduces ovarian weight, and reduces ovulation. Abstract The article contains sections titled: 1. From: Encyclopedia of Toxicology (Third Edition), 2014, S. Saeidnia, in Encyclopedia of Toxicology (Third Edition), 2014. The most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. These phthalates seem to act via multiple modes of action. In: Staples, C.A. This exposure route is suggested to be of limited importance for adults. phthalic acid: ChEBI ID CHEBI:29069: Definition A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. 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). Di(2-ethylhexyl) phthalate (DEHP) and metabolites used to estimate DEHP exposure. What Are Endocrine Disrupters and Where Are They Found? This article was most recently revised and updated by, https://www.britannica.com/science/phthalic-acid. At high doses, testicular toxicity is also induced with adult exposure. In one study, 72 products, purchased directly from stores, were analyzed for their phthalate ester content. Leuenberger et al. 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. Volatility at standard temperature is low, particularly for long-chain phthalates such as DEHP and BBP (Rusyn et al., 2006). 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. 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). products.metrohm.com . The annual production of DEHP sums up to 4 million tons, 95% of which is being used in the manufacturing of PVC products. Updates? It is incompatible with sodium nitrite. We use cookies to help provide and enhance our service and tailor content and ads. In the liver, MEHP was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and FAS. 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 It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. 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). Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. 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. …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. Observed concentrations in the environment. 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. 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. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. Finally human exposure can occur through direct dermal contact with clothes, bags, or toys, but also by using cosmetics. 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. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. Biodegradation is the main mechanism of degradation of PAEs in the environment (the rates of hydrolysis and photolysis are very low). 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). PHTHALIC ACID is a carboxylic acid. 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. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Acids are called phthalic, isophthalic, and hair gels are examples matters... Blood transfusion efficiently increases sport performance and is the main mechanism of of! And iodide uptake but antagonism at the thyroid receptor ( Gore et al. 2004. 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