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Molecules (Basel, Switzerland) Jun 2023In the process of production, processing, transportation, and storage of edible oils, the oils inevitably come into contact with plastic products. As a result,... (Review)
Review
In the process of production, processing, transportation, and storage of edible oils, the oils inevitably come into contact with plastic products. As a result, plasticizers migrate into edible oils, are harmful to human health, and can exhibit reproductive toxicity. Therefore, the determination of plasticizers in edible oils is very important, and a series of sample preparation methods and determination techniques have been developed for the determination of plasticizers in edible oils. Phthalic acid ester (PAE) plasticizers are the most widely used among all plasticizers. This review aims to provide a comprehensive overview of the sample preparation methods and detection techniques reported for the determination of PAEs in edible oils since 2010, focusing on sample preparation methods of edible oils combined with various separation-based analytical techniques, such as gas chromatography (GC) and liquid chromatography (LC) with different detectors. Furthermore, the advantages, disadvantages, and limitations of these techniques as well as the prospective future developments are also discussed.
Topics: Humans; Plasticizers; Phthalic Acids; Plant Oils; Esters
PubMed: 37446766
DOI: 10.3390/molecules28135106 -
Environment International Mar 2023Di-2-ethylhexyl phthalate (DEHP) and its substitute 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINCH) are widely used as plasticizers but may have adverse...
Di-2-ethylhexyl phthalate (DEHP) and its substitute 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINCH) are widely used as plasticizers but may have adverse health effects. Via hydrolysis of one of the two ester bonds in the human body, DEHP and DINCH form the monoesters MEHP and MINCH, respectively. Previous studies demonstrated binding of these metabolites to PPARγ and the induction of adipogenesis via this pathway. Detailed structural understanding of how these metabolites interact with PPARγ and thereby affect human health is lacking until now. We therefore characterized the binding modes of MINCH and MEHP to the ligand binding domain of PPARγ by X-ray crystallography and molecular dynamics (MD) simulations. Both compounds bind to the activating function-2 (AF-2) binding site via an interaction of the free carboxylates with the histidines 323 and 449, tyrosine 473 and serine 289. The alkyl chains form hydrophobic interactions with the tunnel next to cysteine 285. These binding modes are generally stable as demonstrated by the MD simulations and they resemble the complexation of fatty acids and their metabolites to the AF-2 site of PPARγ. Similar to the situation for these natural PPARγ agonists, the interaction of the free carboxylate groups of MEHP and MINCH with tyrosine 473 and surrounding residues stabilizes the AF-2 helix in the upward conformation. This state promotes binding of coactivator proteins and thus formation of the active complex for transcription of the specific target genes. Moreover, a comparison of the residues involved in binding of the plasticizer metabolites in vertebrate PPARγ orthologs shows that these compounds likely have similar effects in other species.
Topics: Humans; Plasticizers; Diethylhexyl Phthalate; PPAR gamma; Furylfuramide; Phthalic Acids
PubMed: 36841188
DOI: 10.1016/j.envint.2023.107822 -
Mutation Research 2012Di(2-ethylhexyl) phthalate (DEHP) is a peroxisome proliferator agent that is widely used as a plasticizer to soften polyvinylchloride plastics and non-polymers. Both... (Review)
Review
Di(2-ethylhexyl) phthalate (DEHP) is a peroxisome proliferator agent that is widely used as a plasticizer to soften polyvinylchloride plastics and non-polymers. Both occupational (e.g., by inhalation during its manufacture and use as a plasticizer of polyvinylchloride) and environmental (medical devices, contamination of food, or intake from air, water and soil) routes of exposure to DEHP are of concern for human health. There is sufficient evidence for carcinogenicity of DEHP in the liver in both rats and mice; however, there is little epidemiological evidence on possible associations between exposure to DEHP and liver cancer in humans. Data are available to suggest that liver is not the only target tissue for DEHP-associated toxicity and carcinogenicity in both humans and rodents. The debate regarding human relevance of the findings in rats or mice has been informed by studies on the mechanisms of carcinogenesis of the peroxisome proliferator class of chemicals, including DEHP. Important additional mechanistic information became available in the past decade, including, but not limited to, sub-acute, sub-chronic and chronic studies with DEHP in peroxisome proliferator-activated receptor (PPAR) α-null mice, as well as experiments utilizing several transgenic mouse lines. Activation of PPARα and the subsequent downstream events mediated by this transcription factor represent an important mechanism of action for DEHP in rats and mice. However, additional data from animal models and studies in humans exposed to DEHP from the environment suggest that multiple molecular signals and pathways in several cell types in the liver, rather than a single molecular event, contribute to the cancer in rats and mice. In addition, the toxic and carcinogenic effects of DEHP are not limited to liver. The International Agency for Research on Cancer working group concluded that the human relevance of the molecular events leading to cancer elicited by DEHP in several target tissues (e.g., liver and testis) in rats and mice can not be ruled out and DEHP was classified as possibly carcinogenic to humans (Group 2B).
Topics: Animals; Carcinogens; Diethylhexyl Phthalate; Humans; Immune System; Kidney; Liver; Liver Neoplasms; Lung; Male; Mice; Peroxisome Proliferators; Plasticizers; Rats; Testicular Neoplasms; Testis
PubMed: 22198209
DOI: 10.1016/j.mrrev.2011.12.004 -
Analytical Chemistry Apr 2016Novel solid-contact iodide-selective electrodes based on covalently attached 1,2,3 triazole ionic liquid (IL) were prepared and investigated in this study....
Novel solid-contact iodide-selective electrodes based on covalently attached 1,2,3 triazole ionic liquid (IL) were prepared and investigated in this study. Triazole-based IL moieties were synthesized using click chemistry and were further copolymerized with lauryl methacrylate via a simple one-step free radical polymerization to produce a "self-plasticized" copolymer. The mechanical properties of the copolymer are suitable for the fabrication of plasticizer-free ion-selective membrane electrodes. We demonstrate that covalently attached IL moieties provide adequate functionality to the ion-selective membrane, thus achieving a very simple, one-component sensing membrane. We also demonstrate that the presence of iodide as the counterion in the triazole moiety has direct influence on the membrane's functionality. Potentiometric experiments revealed that each electrode displays high selectivity toward iodide anions over a number of inorganic anions. Moreover, the inherent presence of the iodide in the membrane reduces the need for conditioning. The nonconditioned electrodes show strikingly similar response characteristics compared to the conditioned ones. The electrodes exhibited a near Nernstian behavior with a slope of -56.1 mV per decade across a large concentration range with lower detection limits found at approximately 6.3 × 10(-8) M or 8 ppb. These all-solid-state sensors were utilized for the selective potentiometric determination of iodide ions in artificial urine samples in the nanomolar concentration range.
Topics: Electrodes; Humans; Iodides; Ionic Liquids; Molecular Structure; Plasticizers; Polymerization; Potentiometry; Triazoles
PubMed: 26965316
DOI: 10.1021/acs.analchem.5b04461 -
Journal of Occupational Health Jan 20192-Ethyl-1-hexanol (2EH), a fragrance ingredient and a raw material for the production of plasticizer di(2-ethylhexyl) phthalate, is responsible for sick building... (Review)
Review
OBJECTIVES
2-Ethyl-1-hexanol (2EH), a fragrance ingredient and a raw material for the production of plasticizer di(2-ethylhexyl) phthalate, is responsible for sick building syndrome (SBS). This review aims to clarify the 2EH characteristics as an indoor air pollutant such as indoor air concentration, emission mechanism, toxicity, and clinical effects.
METHODS
Scientific publications in English that has been made available on PubMed as of June 2018 and ad hoc publications in regional languages were reviewed.
RESULTS
Inhalation exposure to 2EH caused mucous membrane irritation in the eyes, nose, and throat in experimental animals. Studies in human volunteers revealed an increase in olfactory irritation and eye discomfort. There has been increasing evidence of 2EH being present in indoor air in buildings. The primary sources of 2EH emissions are not building materials themselves, but instead the hydrolysis of plasticizers and flooring adhesives. In particular, compounds like di(2-ethylhexyl) phthalate present in polyvinyl chloride flooring materials are hydrolyzed upon contact with alkaline moisture-containing concrete floors. That being said, it may be observed that indoor concentrations of 2EH increased every year during summer.
CONCLUSIONS
Unlike other volatile organic compounds that cause SBS, 2EH can be retained in indoor air for long durations, increasing the likelihood of causing undesirable health effects in building occupants exposed to it. As a precautionary measure, it is important to use flooring materials that do not emit 2EH by hydrolysis, or to dry concrete before covering with flooring materials.
Topics: Administration, Oral; Air Pollutants; Air Pollution, Indoor; Animals; Construction Materials; Disease Models, Animal; Floors and Floorcoverings; Hexanols; Humans; Inhalation Exposure; Mice; Plasticizers; Rats
PubMed: 30698348
DOI: 10.1002/1348-9585.12017 -
Cells Sep 2021The use of the plasticizer bis(2-ethylhexyl)phthalate (DEHP) and other plasticizers in the manufacture of plastic products has been restricted due to adverse health...
The use of the plasticizer bis(2-ethylhexyl)phthalate (DEHP) and other plasticizers in the manufacture of plastic products has been restricted due to adverse health outcomes such as obesity, metabolic syndrome, and asthma, for which inflammation has been described to be a driving factor. The emerging alternative plasticizer 1,2-cyclohexanedioic acid diisononyl ester (DINCH) still lacks information regarding its potential effects on the immune system. Here, we investigated the effects of DINCH and its naturally occurring metabolite monoisononylcyclohexane-1,2-dicarboxylic acid ester (MINCH) on the innate immune response. Human THP-1 macrophages were exposed to 10 nM-10 μM DINCH or MINCH for 4 h, 16 h, and 24 h. To decipher the underlying mechanism of action, we applied an untargeted proteomic approach that revealed xenobiotic-induced activation of immune-related pathways such as the nuclear factor κB (NF-κB) signaling pathway. Key drivers were associated with oxidative stress, mitochondrial dysfunction, DNA damage repair, apoptosis, and autophagy. We verified increased reactive oxygen species (ROS) leading to cellular damage, NF-κB activation, and subsequent TNF and IL-1β release, even at low nM concentrations. Taken together, DINCH and MINCH induced cellular stress and pro-inflammatory effects in macrophages, which may lead to adverse health effects.
Topics: Apoptosis; DNA Damage; DNA Repair; Dicarboxylic Acids; Esters; Humans; Inflammation; Macrophages; NF-kappa B; Oxidative Stress; Phthalic Acids; Plasticizers; Proteomics; Signal Transduction; THP-1 Cells
PubMed: 34572016
DOI: 10.3390/cells10092367 -
Cardiovascular Toxicology Dec 2014The ubiquitous nature of plastics has raised concerns pertaining to continuous exposure to plastic polymers and human health risks. Of particular concern is the use of... (Review)
Review
The ubiquitous nature of plastics has raised concerns pertaining to continuous exposure to plastic polymers and human health risks. Of particular concern is the use of endocrine-disrupting chemicals in plastic production, including di(2-ethylhexyl)phthalate (DEHP) and bisphenol A (BPA). Widespread and continuous exposure to DEHP and BPA occurs through dietary intake, inhalation, dermal and intravenous exposure via consumer products and medical devices. This article reviews the literature examining the relationship between DEHP and BPA exposure and cardiac toxicity. In vitro and in vivo experimental reports are outlined, as well as epidemiological studies which examine the association between these chemicals and cardiovascular outcomes. Gaps in our current knowledge are also discussed, along with future investigative endeavors that may help resolve whether DEHP and/or BPA exposure has a negative impact on cardiovascular physiology.
Topics: Benzhydryl Compounds; Cardiotoxicity; Child; Child, Preschool; Diethylhexyl Phthalate; Endocrine Disruptors; Environmental Exposure; Estrogens, Non-Steroidal; Humans; Infant; Infant, Newborn; Phenols; Plasticizers; Plastics
PubMed: 24811950
DOI: 10.1007/s12012-014-9258-y -
Scientific Reports Mar 2022Non-destructive spectroscopic analysis combined with machine learning rapidly provides information on the identity and content of plasticizers in PVC objects of heritage...
Non-destructive spectroscopic analysis combined with machine learning rapidly provides information on the identity and content of plasticizers in PVC objects of heritage value. For the first time, a large and diverse collection of more than 100 PVC objects in different degradation stages and of diverse chemical compositions was analysed by chromatographic and spectroscopic techniques to create a dataset used to construct classification and regression models. Accounting for this variety makes the model more robust and reliable for the analysis of objects in museum collections. Six different machine learning classification algorithms were compared to determine the algorithm with the highest classification accuracy of the most common plasticizers, based solely on the spectroscopic data. A classification model capable of the identification of di(2-ethylhexyl) phthalate, di(2-ethylhexyl) terephthalate, diisononyl phthalate, diisodecyl phthalate, a mixture of diisononyl phthalate and diisodecyl phthalate, and unplasticized PVC was constructed. Additionally, regression models for quantification of di(2-ethylhexyl) phthalate and di(2-ethylhexyl) terephthalate in PVC were built. This study of real-life objects demonstrates that classification and quantification of plasticizers in a general collection of degraded PVC objects is possible, providing valuable data to collection managers.
Topics: Diethylhexyl Phthalate; Machine Learning; Phthalic Acids; Plasticizers; Polyvinyl Chloride; Spectrum Analysis
PubMed: 35322097
DOI: 10.1038/s41598-022-08862-1 -
World Journal of Gastroenterology Nov 2013Pharmaceutical companies that produce gastrointestinal (GI) medications often utilize phthalates for their ability to localize medication release. Commonly prescribed GI... (Review)
Review
Pharmaceutical companies that produce gastrointestinal (GI) medications often utilize phthalates for their ability to localize medication release. Commonly prescribed GI medications that may utilize phthalates are 5-Aminosalicylates, proton pump inhibitors, and pancreatic enzymes. Our understanding of the cumulative health effects of phthalates from medications remains unclear, and there is increasing evidence that phthalates are not harmless. Experimental studies in animals have shown that phthalates, specifically dibutyl phthalate and Di-(2-ethyl-hexyl) phthalate, have the potential to alter and/or inhibit reproductive biology and in utero development. Despite the lack of definitive human data, many cohort and cross-sectional studies demonstrate concerning associations between phthalates and poor health status, specifically developmental problems. Longitudinal studies and studies with larger sample sizes are required to determine whether phthalates actually cause negative health consequences. It is also important that physicians regularly review and discuss with patients the medicinal ingredients in their medications and supplements, specifically in pregnant woman with inflammatory bowel disease.
Topics: Animals; Drug Contamination; Female; Gastrointestinal Agents; Humans; Inflammatory Bowel Diseases; Male; Patient Safety; Phthalic Acids; Plasticizers; Pregnancy; Pregnancy Complications; Risk Assessment; Risk Factors
PubMed: 24222946
DOI: 10.3748/wjg.v19.i41.7042 -
Food Chemistry Jan 2023Novel chitosan (Ch) films containing choline chloride and citric acid mixture as plasticizer (deep eutectic solvent, DES) and different amounts of quercetin (QUE) as...
Novel chitosan (Ch) films containing choline chloride and citric acid mixture as plasticizer (deep eutectic solvent, DES) and different amounts of quercetin (QUE) as antioxidant additive were prepared. Physicochemical and mechanical characteristics of the developed Ch/DES/QUE films were studied using FTIR, SEM, and AFM techniques. FTIR spectra revealed the possible interactions between all the components. The surface of the films was dense and rough. The addition of quercetin caused an increase in the tensile strength (TS) and Young's modulus, but significantly decreased the elongation at break. The films containing quercetin showed improved antioxidant activity in relation to Ch/DES film. Finally, the oxidation phenomena of rapeseed oils with and without chitosan films were evaluated as amounts of primary and secondary oxidation products and total oxidation index. The addition of Ch/DES films with quercetin to oil samples successfully retarded secondary lipid oxidation processes and improved its antioxidant activity under the accelerated storage condition.
Topics: Antioxidants; Chitosan; Food Packaging; Plasticizers; Quercetin; Tensile Strength
PubMed: 35998489
DOI: 10.1016/j.foodchem.2022.133934