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Phthalates
Published in Dongyou Liu, Handbook of Foodborne Diseases, 2018
Phthalates are a group of colorless, odorless, synthetic chemicals first produced in the 1920s that have been used as plasticizers since their synthesis as a replacement for the more volatile plasticizer camphor.6 Their widespread use did not occur until the synthesis of PVC and DEHP (also known as bis[2-ethylhexyl] phthalate, Bisoflex 81, Eviplast 80, Octoil, Plantinol DOP, and Starflex DOP) in 1931 and 1933, respectively.6 Phthalates consist of a benzene ring with a diester structure, and are synthesized from phthalic anhydride in a two-step process.6 In the first step, a monoester is rapidly formed through the reaction of phthalic anhydride with an alcohol. The second step occurs more slowly, resulting in the conversion of the monoester into a diester through a second alcoholysis reaction. This reaction is reversible and generates H2O as a by-product.6
Environmental toxicants on Leydig cell function
Published in C. Yan Cheng, Spermatogenesis, 2018
Leping Ye, Xiaoheng Li, Xiaomin Chen, Qingquan Lian, Ren-Shan Ge
Phthalates are synthetic compounds that are esters created by joining a phthalic anhydride with two alcohols that range from methanol (C1) up to tridecyl alcohol (C13). Phthalates can have either a straight chain or a branching chain. They are widely used as plasticizers and solvents in a variety of consumer products.86 Low-molecular-weight phthalates (those with 1–6 carbons in the alcohol moiety), including dimethyl (DMP, C1), diethyl (DEP, C2), dipropyl (DPrP, C3), dibutyl (DBP, C4), diisobutyl (DIBP, C4), dipentyl (DPeP, C5), butyl benzyl (BBzP, C4/C6), dihexyl (DHP, C6), bis(2-butoxyethyl) (BBOP, C6+O), and dicyclohexyl (DCHP, C6) phthalate, are dominantly used in personal care products (such as perfumes, lotions, and other cosmetics) or as solvents for cellulose acetate, and in making lacquers and varnishes.87 High-molecular-weight phthalates (those with 7–13 carbons in the alcohol moiety), including diisoheptyl (DIHP, C7), di(2-ethylhexyl) (DEHP, C8), di-n-octyl (DNOP, C8), diisononyl (DINP, C9), diisodecyl (DIDP, C10), diundecyl (DIUP, C11), and ditridecyl (DTDP, C13), are primarily used as plasticizers in the manufacture of flexible vinyl that is used in consumer products such as flooring and wall coverings, food containers and covers, and medical devices.87
Chemical Compounds as Trigger Factors of Immediate Contact Skin Reactions
Published in Ana M. Giménez-Arnau, Howard I. Maibach, Contact Urticaria Syndrome, 2014
In the plastic industry, workers are in contact with highly reacting chemicals. Cyclic acid anhydrides are synthetic highly reactive LMW compounds widely used as curing agents for epoxy resins and in the production of polyester resins. Commonly used anhydrides are phthalic anhydride, tetrahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, maleic anhydride, and trimellitic anhydride. Cyclic acid anhydrides often cause allergic respiratory diseases, and in the literature only single case reports of CoU of a few patients were found. However, recently, occupational CoU has been described by a Finnish study as workers may be exposed in powder or liquid form during manufacturing processes.[64] Data are presented for 21 subjects who had been diagnosed with occupational CoU because of exposure to organic acid anhydrides and examined during 1990–2006. Prick tests with HSA-acid anhydrides conjugates, RAST determination of specific IgE and open application tests were used for the diagnosis. The majority of the patients had been exposed to an epoxy resin containing methyl hexahydrophthalic anhydride. Specific IgE results were in line with the prick tests and the large reaction was seen for the acid anhydride the patient had been exposed to. Phthalic anhydride IgE was positive in 19 of 20 patients. The authors concluded that CoU to these compounds may be more common than previously believed, as first shown by a previous Finnish study with two patients.[65]
Characterization of diphenyl phthalate as an agonist for estrogen receptor: an in vitro and in silico study
Published in Toxicology Mechanisms and Methods, 2022
Chengyu Lv, Zhengyi Wei, Benjie Yue, Ning Xia, Wei Huang, Yulan Yue, Zhuolin Li, Tiezhu Li, Xiuxia Zhang, Yongjun Wang
Phthalate esters (PAEs) can be used to improve the flexibility, processability and longevity of plastic products. However, PAEs have become global organic pollutants to the environment for their wide application in food packing materials, cosmetics, toys, building materials, medical tubing, blood bags and other products (Wormuth et al. 2006; Martino Andrade and Chahoud 2010; Kim et al. 2020). Phthalates are synthesized by the reaction of phthalic anhydride with alcohols of different chain lengths (C1 to C13) (Gardner et al. 2016). Phthalates are not covalent with polymer chains, since they can easily migrate to fatty food (Sharman et al. 1994), water, indoor air (Preece et al. 2021), indoor dust (Rudel et al. 2003), soil and other environmental media during production and application. Some research suggested that phthalates and their metabolites have been detected in human biological samples (Silva et al. 2005; Valvi et al. 2015), which may enter the human body through the respiratory tract, digestive tract, and skin (Latini 2005; Bao et al. 2015). Naturally, the concerning safety issues have attracted much attention.
Framework for sensitization assessment of extractables and leachables in pharmaceuticals
Published in Critical Reviews in Toxicology, 2022
Patricia Parris, Geraldine Whelan, Anders Burild, Jessica Whritenour, Uma Bruen, Joel Bercu, Courtney Callis, Jessica Graham, Esther Johann, Troy Griffin, Martin Kohan, Elizabeth A. Martin, Melisa Masuda-Herrera, Brad Stanard, Eric Tien, Maureen Cruz, Lee Nagao
For the purposes of E&L sensitization assessment, ELSIE recommends a conservative and precautionary approach that any chemical identified (or predicted using in silico methods) to be a skin sensitizer provides an indication that the chemical can activate T cells (or activate the immune system). Therefore, the chemical is assumed to have the potential to be a respiratory sensitizer and is evaluated accordingly. A literature search was conducted to identify if there are any human case reports of induction of sensitization associated with known respiratory sensitizers as E&Ls. No case studies or clinical reports were found suggesting there is little evidence of a safety concern thus far. However, measurement of IgE levels is not routinely conducted on clinical studies with novel pharmaceuticals, let alone for E&Ls. Occupational case reports were identified associated with phthalic anhydride (CAS No. 85-44-9) which is a known respiratory sensitizer, and a chemical intermediate in the plastics industry. Phthalic anhydride is reported in the ELSIE database however, based on feedback from ELSIE consortium members, it is generally observed as an extractable and not a leachable substance.