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Concept: Phthalates

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Di-(2-ethylhexyl) phthalate (DEHP) is a plasticizer widely used in the production of poly-(vinyl) chloride (PVC) materials. It is a reproductive and developmental toxicant in animals and a suspected endocrine modulator in humans. DEHP is not covalently bound within the PVC molecule, which is why migration into a suitable medium can be expected. Since application of infusion solutions is one of the most common medical treatments, the objective of this study was to determine the migration of phthalates from softened PVC storage bags into infusion solution in different time periods within one year from date of production using a gas chromatography-mass spectrometry method. The measured values of DEHP ranged between 0.22 and 14.00 µg l(-1) , but the unexpected presence of other phthalate esters was also detected. It was concluded that values obtained in infusion solutions match the reference data and represent a minor risk for the patient. The presence of other phthalate esters leads to the conclusion that the pharmacopeic requirement for polymer cleanness was not fully met. Since phthalate esters are among the most extensively used industrial chemicals and are widely distributed in the environment, special precautions and further monitoring should be conducted to minimize any possible health risks.

Concepts: Diisononyl phthalate, Phthalates, Plasticizers, Plastic, Chemistry, Bis(2-ethylhexyl) phthalate, Phthalate, Plasticizer

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This survey determined the levels of eight phthalates - i.e. dimethyl phthalate (DMP), diethyl phthalate (DEP), diisobutyl phthalate (DiBP), di-n-butyl phthalate (DnBP), benzylbutyl phthalate (BzBP), di(2-ethylhexyl) phthalate (DEHP), dicyclohexyl phthalate (DCHP) and di-n-octyl phthalate (DnOP) - in several Belgian milk and dairy products. Samples were obtained from various farms, a dairy factory and from different shops in order to investigate phthalate contamination “from farm to fork”. At several stages in the milk chain, product contamination with phthalates - mostly DiBP, DnBP, BzBP and DEHP - was observed. At farm level, the mechanical milking process and the intake of phthalate containing feed by the cattle were found to be possible contamination sources. At industry and retail level, contact materials including packaging materials were additional contamination sources for phthalates in milk and dairy products.

Concepts: Diethyl phthalate, Diisobutyl phthalate, Cattle, Plasticizers, Milk, Dairy, Phthalate, Phthalates

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Human exposure to phthalates was assessed through digestive and respiratory intakes. Six phthalates (DMP, DEP, DnBP, BBP, DEHP, DnOP) were investigated in drinking water, in current foodstuff and in ambient air. Digestive intake was prevailing (92 %) with a major contribution of food (95.5 %). Phthalate intake from water was mainly due to bottled water (60 %) in spite of the minor volume absorbed daily. From the respiratory tract, it was dominated by DEP: 30.3 ng kg(-1) bw day(-1) and the part played by indoor air prevailed. Total intake were as ng kg(-1) bw day(-1), for DEHP: 1458, DnBP: 191.8, BBP: 164.3, DEP: 107.7, DMP: 79.1.

Concepts: Assessment, Intake, Phthalates, Plasticizer, Water, Bottled water, Bis(2-ethylhexyl) phthalate, Phthalate

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Urinary phthalate excretion is used as marker of phthalate exposure in epidemiological studies. Here we examine the reliability of urinary phthalate levels in exposure classification by comparing the inter- and intra-subject variation of urinary phthalate metabolite levels. 33 young healthy men each collected two spot-, three first-morning- and three 24-hour urine samples during a three month period. Samples were analyzed for the content of 12 urinary metabolites of seven different phthalates. Variability was assessed as intraclass correlation coefficients (ICC). For the metabolites of diethyl-, dibutyl-, and butylbenzyl-phthalates moderate ICCs were observed in all three sample types, albeit highest in 24-hour urine (0.51 - 0.59). For the metabolites of di(2-ethylhexyl) phthalate and di-iso-nonyl phthlates lower ICCs (0.06-0.29) were found. These low ICCs indicate a high risk of misclassification of exposures for these two phthalates in population studies and hence an attenuation of the power to detect possible exposure-outcome associations. The only slightly higher ICCs for 24-hour pools compared to first-morning and spot urine samples does not seem to justify the extra effort needed to collect 24-hour pools.

Concepts: The Extra, Epidemiology, Demography, Metabolism, Phthalates

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Esters of phthalic acid are chemical agents used to improve the plasticity of industrial polymers. Their ubiquitous use in multiple commercial products results in extensive exposure to humans and the environment. This study investigated cytotoxicity, endocrine disruption, effects mediated via AhR, lipid peroxidation and effects on expression of enzymes of xenobiotic metabolism caused by di-(2-ethy hexyl) phthalate (DEHP), diethyl phthalate (DEP), dibutyl phthalate (DBP) and benzyl butyl phthalate (BBP) in developing fish embryos. Oxidative stress was identified as the critical mechanism of toxicity (CMTA) in the case of DEHP and DEP, while the efficient removal of DBP and BBP by phase 1 enzymes resulted in lesser toxicity. DEHP and DEP did not mimic estradiol (E(2)) in transactivation studies, but at concentrations of 10mg/L synthesis of sex steroid hormones was affected. Exposure to 10mg BBP/L resulted in weak transactivation of the estrogen receptor (ER). All phthalates exhibited weak potency as agonists of the aryl hydrocarbon receptor (AhR). The order of potency of the 4 phthalates studied was; DEHP>DEP>BBP>DBP. The study highlights the need for simultaneous assessment of (1) multiple cellular targets affected by phthalates and (2) phthalate mixtures to account for additive effects when multiple phthalates modulate the same pathway. Such cumulative assessment of multiple biological parameters is more realistic, and offers the possibility of more accurately identifying the CMTA.

Concepts: Phthalic acid, Dibutyl phthalate, Bis(2-ethylhexyl) phthalate, Estrogen, Steroid, Phthalate, Metabolism, Phthalates

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Food products can be contaminated with toxic compounds via the environment. Another possibility of food contamination is that toxicants are generated in foods or that chemicals migrate from food contact materials into foods during processing. In this study, the effect of cooking at home on the levels of phthalates - world’s most used group of plasticisers - in various food types (starchy products, vegetables and meat and fish) was examined. Eight compounds were considered, namely dimethyl phthalate (DMP), diethyl phthalate (DEP), diisobutyl phthalate (DiBP), di-n-butyl phthalate (DnBP), benzylbutyl phthalate (BBP), di(2-ethylhexyl) phthalate (DEHP), dicyclohexyl phthalate (DCHP) and di-n-octyl phthalate (DnOP). Food products were analysed before as well as after cooking (boiling, steaming, (deep-)frying or grilling). In general, phthalate concentrations in foods declined after cooking, except in vegetables, where almost no effect was seen. Several factors influenced the degree of this decline (e.g. weight difference, fat uptake, etc.). Of all phthalates, DEHP, DiBP and BBP were affected the most. In conclusion, cooking at home definitely affected phthalate concentrations in foods and thus needs to be considered in order to correctly assess humans' dietary exposure to these contaminants.

Concepts: Bis(2-ethylhexyl) phthalate, Food safety, Food, Plasticizers, Phthalate, Cooking, Phthalates, Nutrition

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A comprehensive study of the sonochemical degradation of dimethyl phthalate (DMP) was carried out using high-frequency ultrasonic processes. The effects of various operating parameters were investigated, including ultrasonic frequency, power density, initial DMP concentration, solution pH and the presence of hydrogen peroxide. In general, a frequency of 400kHz was the optimum for achieving the highest DMP degradation rate. The degradation rate was directly proportional to the power density and inversely related to the initial DMP concentration. It was interesting to find that faster removal rate was observed under weakly acidic condition, while hydrolysis effect dominated in extreme-basic condition. The addition of hydrogen peroxide can increase the radical generation to some extent. Furthermore, both hydroxylation of the aromatic ring and oxidation of the aliphatic chain appear to be the major mechanism of DMP degradation by sonolysis based on LC/ESI-MS analysis. Among the principle reaction intermediates identified, tri- and tetra-hydroxylated derivatives of DMP, as well as hydroxylated monomethyl phthalates and hydroxylated phthalic acid were reported for the first time in this study. Reaction pathways for DMP sonolysis are proposed based on the detected intermediates.

Concepts: Redox, Ultrasound, Phthalates, Oxygen, Acid, PH, Phthalic acid, Phthalate

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Several phthalates, particularly diethyl phthalate (DEP) and di-n-butyl phthalate, can be used in personal care products (PCPs) to fix fragrance and hold color. We investigated associations between women’s reported use of PCPs within the 24 h before urine collection and concentrations of several urinary phthalate metabolites. Between 2002 and 2005, 337 women provided spot urine samples and answered questions regarding their use of 13 PCPs at a follow-up visit 3-36 months after pregnancy. We examined associations between urinary concentrations of several phthalate metabolites and use of PCPs using linear regression. Use of individual PCPs ranged from 7% (nail polish) to 91% (deodorant). After adjusting for age, education, and urinary creatinine, women reporting use of perfume had 2.92 times higher (95% CI: 2.20-3.89) concentration of monoethyl phthalate (MEP; the primary metabolite of DEP) than other women. Other PCPs that were significantly associated with MEP concentrations included: hair spray, nail polish, and deodorant. MEP concentrations increased with the number of PCPs used. PCP use was widespread in this group of recently pregnant women. Women’s use of PCPs, particularly of perfumes and fragranced products, was positively associated with urinary concentration of multiple phthalate metabolites.Journal of Exposure Science and Environmental Epidemiology advance online publication, 21 November 2012; doi:10.1038/jes.2012.105.

Concepts: Diethyl phthalate, Metabolite, Phthalate, Perfume, Pregnancy, Toiletry, Cosmetics, Phthalates

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A method based on gas chromatography-mass spectrometry (GC-MS) combined with a pressurised liquid extraction (PLE) to determine four organophosphates, seven phthalate esters and bis(2-ethylhexyl) adipate in particulated material of harbour air samples has been developed. Some studies show that these compounds may cause hormone disrupting effects on human health. Moreover, the U.S. Environmental Protection Agency (EPA) has classified benzyl butyl phthalate and di(2-ethylhexyl) phthalate as possible human carcinogens.The chromatographic time per run analysis is less than 15min and the complete separation of all compounds is achieved. The PLE was optimised with recoveries above 90% and the repeatability of the method with real samples is less than 11% (%RSD, n=4). The MDLs (0.004-0.4ngm(-3)) and MQLs (0.02-2ngm(-3)) are limited by the fact of some compounds are present in low levels in sampling blank filters.The method was successfully applied in several samples and most of the compounds under study were found. The most relevant values were the high concentration of di-iso-butyl phthalate (between 28 and 529ngm(-3)) and the significant concentration of di(2-ethylhexyl) phthalate (between MQL and 22ngm(-3)). In addition, benzyl butyl phthalate was also detected in some samples but at low concentration levels (between MQL to 0.2ngm(-3)).

Concepts: Mass spectrometry, Analytical chemistry, Chromatography, Phthalates, Phthalate, Concentration, United States Environmental Protection Agency, Plasticizer

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Some phthalates are endocrine disruptors and reproductive and developmental toxicants. Data on newborn phthalate exposure and elimination characteristics are scarce. We determined 21 urinary phthalate metabolites (indicating exposure to 11 parent phthalates) in two study approaches: in the first approach we collected the urine of 20 healthy newborns at days 2-5 post partum together with 47 urine samples of 7 women during pregnancy. In the second fine tuned approach we collected first urine samples of 9 healthy newborns together with their mother’s urine shortly before birth. To ensure full and contamination free collection of the newborns first urines we used special adhesive urine bags for children. All urine samples revealed ubiquitous exposures to phthalates comparable to other populations. Metabolite levels in the newborns first day urine samples were generally lower than in all other samples. However, the newborns urines (both first and day 2-5 urines) showed a metabolite pattern distinctly different from the maternal and general population samples: in the newborns urines the carboxy-metabolites of the long chain phthalates (DEHP, DiNP, DiDP) were the by far dominant metabolites with a relative share in the metabolite spectrum up to 6 times higher than in maternal urine. Oppositely, for the short chain phthalates (DBP, DiBP) oxidized metabolites seemed to be less favored than the simple monoesters in the newborns urines. The skewed metabolite distribution in the newborns urine warrants further investigation in terms of early phthalate metabolism, the quantity of internal phthalate exposure of the fetus/newborn and its possible health effects.

Concepts: Metabolism, Plasticizer, Bis(2-ethylhexyl) phthalate, Phthalates, Phthalate, Infant, Pregnancy, Childbirth