Prenatal exposure to DEHP leads to reduced ovarian weight and increased uterine weight in female mice. It is incompatible with sodium nitrite. It used as an intermediate for polyesters, polyurethane resins, plasticizers. Phthalates are mainly used in gastrointestinal drug coatings to localize medication release. There are six different types of phthalates; DEHP (di-ethylhexyl phthalate), BBP (benzyl-butyl phthalate,), and DINP (diisononyl phthalate) have potent antiandrogenic properties. DEHP removal during sludge composting, Philippa D. Darbre, in Endocrine Disruption and Human Health, 2015. The mechanism by which phthalates interfere with thyroid function is not entirely understood. DEHP is the dominant plasticizer used in polyvinyl chloride (PVC) due to its low cost. Jan Ludvig Lyche, in Reproductive and Developmental Toxicology (Second Edition), 2017. 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). Dimethyl Phthalate is useful as an insect repellent. 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). 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). (2016) detected significantly increased levels of DEHP metabolites in urine 1–2 days after autologous blood transfusions. The high value of DEHP in the anaerobically digested sludge can be attributed to its low biodegradation under anaerobic conditions. Interestingly, substantial levels of DEHP were also found in blood bags labeled DEHP-free (Leuenberger et al., 2016). Table 44.2. N-Hydroxyphthalimid aus Phthalsäuredichlorid.svg 433 × 110; 33 KB. 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. Indeed, multiple studies in animals, testing various phthalates, showed that phthalate exposure led to increases in body fat and. Omissions? 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. 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). 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. In Germany higher levels of DEHP were detected in kindergartens than in apartments (Fromme et al., 2004). Phthalates may permeate into humans via inhalation of indoor air in rooms with large surfaces of PVC-containing products (Table 44.1). This compound reacts violently with nitric acid. Both animal and human epidemiologic data support the hypothesis that phthalates lead to reductions in thyroid hormone levels (Eisenbrand and Gelbke, 2016). Also of practical importance are the cyclic imide (phthalimide) and dichloranhydride (phthalyl chloride) of ortho-phthalic acid, as well as phthalylsulfathiazole (Ftalazol). The water solubility is low and decreases with increasing length of the side chain (the alcohol moiety) or with higher molecular weight (MW). Abstract The article contains sections titled: 1. 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. Phthalic acid, also called 1, 2-benzenedicarboxylic Acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. 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. products.metrohm.com. 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. Exposure during fetal development altered follicular recruitment and development, eventually causing premature ovarian failure. Table 4. 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). Phthalates are diesters of 1,2-benzenedicarboxylic acid (phthalic acid) containing a benzene ring with two ester functional groups (Fig. The most widely used phthalates are di(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate, and diisononyl phthalate. Phthalic acid esters (phthalates) are used as plasticizers in numerous consumer products, commodities, and building materials. Their ability to reduce testicular testosterone production during late gestation in rats is associated with impaired development of androgen-dependent tissues. Phthalic acid definition: a soluble colourless crystalline acid used in the synthesis of dyes and perfumes ;... | Meaning, pronunciation, translations and examples 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. 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). It may be difficult for people to avoid exposure from cosmetic products even though they are subjected to strict labeling requirements. Phthalic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Le catalyseur du type V.P.O. In the liver, MEHP was shown to activate PPARG and induce its downstream targets, including aP2, LPL, and FAS. It is recommended to take special care regarding the storage conditions on bottles. 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. Phthalic anhydride is extensively used in the manufacture of the so-called alkyd resins. In the evaluation of phthalates, one must distinguish between low molecular weight (DEHP, DBP, etc.) No damage or toxicity to humans after handling the substance for a prolonged period has been reported (BG Chemie 1990). In this way, MEHP promoted preadipocyte differentiation and adipogenesis. Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for Safe alternatives such as glass or polyethylene plastics and phthalate-free labeled are highly recommended. Phthalic Acid 2. 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). 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. Leuenberger et al. It has a role as a human xenobiotic metabolite. 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. 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. However, for those who wear clothes exposed to phthalates the uptake was significantly higher than for those who were exposed without clothes. Further to its effect on humans, DEHP has been found to be toxic to other organisms such as plants, marine organisms, and anaerobic microorganisms. 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). 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). The world's first wiki where authorship really matters. Phytochemical profiling of leaf, stem, and tuber … Many of the phthalates are individually listed by the OECD in their 2004 list of HPV chemicals [34]. 44.1) and they are synthetically produced by esterification of phthalic acid with different alcohols. CAMEO Chemicals. …dicarboxylic acids are called phthalic, isophthalic, and terephthalic acid, for the ortho, meta, and para isomers, respectively. 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). 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). Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. Therefore, DEHP, DBP, BBP, and DIBP have been classified as being reproductive toxicants (ECHA, 2017). Concentrations of Di(2-ethylhexyl) Phthalate in Various Environmental Matrices. Let us know if you have suggestions to improve this article (requires login). 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. Oxidation p-Xylol zu TPA.svg 488 × 150; 137 KB. 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. p‐Phthalic acid is used as a starting material for the production of polyesters. Together, these genes stimulate fatty acid uptake and TAG synthesis (Hao et al., 2012a). Chemical Properties 2.3. The windows of sensitivity appear to differ between rodents and primates (Albert and Jégou, 2014). What Are Endocrine Disrupters and Where Are They Found? It is an isomer of isophthalic acid and terephthalic acid. 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 DEHP is produced from phthalate anhydride reacting with 2-ethylhexanol. 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). 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. and higher molecular weight phthalates (DINP, DIDP, DPHP, etc.). PHTHALIC ACID is a carboxylic acid. 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. The EU has already taken steps to reduce the use of certain phthalates (such as DEHP). Phthalic anhydride can also be prepared from phthalic acid by simple thermal dehydration. 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. Table 44.1. 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). K. Stamatelatou, ... G. Lyberatos, in Comprehensive Biotechnology (Second Edition), 2011. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. 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. 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. 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. 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). Phthalic Anhydride 2.1. 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. It is not currently clear whether other phthalates than those with intermediate chain lengths can also adversely affect the male reproductive system. Herbal preparations and nutritional supplements, including some intended for use during pregnancy, may also contain phthalates in the formulation (Schettler, 2006). 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. 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). Phthalic definition: of or derived from phthalic acid | Meaning, pronunciation, translations and examples Reproduced from Clark, K., Cousins, I.T., Mackay, D., Yamada, K., 2003. Smaller quantities were consumed in the manufacture of anthraquinone (a dye intermediate), phenolphthalein (a laxative and acid-base indicator), and phthalocyanine pigments. Phthalic acid, isophthalic acid and terephthalic acid are all isomers of each other. 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. Our editors will review what you’ve submitted and determine whether to revise the article. 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. Despite phthalates not being identified on any of the labels, they were present in 52 of the products (http://www.environmentalhealth.ca/fall02pretty.html). Springer-Verlag, New York, pp. 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 (Ed. Source: GreenFacts Polyesters containing isophthalic acid are also used extensively in industrial coatings applications for home appliances, automobiles, aluminum siding, and metal office furniture. Concentration of DEHP in primary, secondary, dehydrated anaerobically digested, and composted sludge in samples taken from four sewage-treatment plants in Seville [7]. … ), The Handbook of Environmental Chemistry. Uses Phthalate esters plasticizers. Physical Properties 2.2. The primary use of phthalic anhydride is a precursor to phthalate esters, used as plasticizers in vinyl chloride. 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. The annual production of DEHP sums up to 4 million tons, 95% of which is being used in the manufacturing of PVC products. Without chemical suppression it can be used with normal phthalic acid eluents and a range of other eluent systems. Although the levels of phthalates in bottled waters have been detected as low, high consumption of such waters leads to a concern. 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. Phthalic acid definition is - any of three isomeric acids C8H6O4 obtained by oxidation of various benzene derivatives. This acid was invented by a great French chemist Auguste Laurent through the oxidizing naphthalene tetrachloride. Uses of the various phthalates mainly depend on their MW. 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). Morrison et al. 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. 1,2-benzenedicarboxylic acid synonyms, 1,2-benzenedicarboxylic acid pronunciation, 1,2-benzenedicarboxylic acid translation, English dictionary definition of 1,2-benzenedicarboxylic acid. Phthalates are among the most common synthetic chemicals to which humans are exposed. phthalic acid: ChEBI ID CHEBI:29069: Definition A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. 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. Imagine a global collaborative knowledge base … As phthalates are not covalently bound to the plastic, they can leak out of products and enter the environment this way. They are also used in PVC (Heudorf et al., 2007). Humans are exposed to phthalates through ingestion, inhalation, and dermal contact. Humans may also be exposed orally to phthalates incorporated in the coatings of commonly used pharmaceuticals. 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). The information is aggregated from the data coming from REACH substance registrations provided by … Being structurally similar, they can present difficulties to reverse-phase HPLC separation. The dinitrile of ortho-phthalic acid (phthalonitrile) is used in the production of phthalocyanine dyes and polyphthalocyanines. 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. 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. 125–177. 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. 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. Define 1,2-benzenedicarboxylic acid. Animal studies have shown enhancement of NIS expression and iodide uptake but antagonism at the thyroid receptor (Gore et al., 2015). Phthalates are a family of compounds that are used extensively in medical, automotive, and cosmetics production. 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). Media in category "Phthalic acid" The following 23 files are in this category, out of 23 total. Butylbenzylphthalate is used in the manufacture of foamed PVC, which is used mostly as a flooring material. 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