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Phthalic acid esters (PAEs) are a class of lipophilic chemicals widely used as plasticizers and additives to improve various products’ mechanical extensibility and flexibility. At present, synthesized PAEs, which are considered to cause potential hazards to ecosystem functioning and public health, have been easily detected in the atmosphere, water, soil, and sediments; PAEs are also frequently discovered in plant and microorganism sources, suggesting the possibility that they might be biosynthesized in nature. In this review, we summarize that PAEs have not only been identified in the organic solvent extracts, root exudates, and essential oils of a large number of different plant species, but also isolated and purified from various algae, bacteria, and fungi. Dominant PAEs identified from natural sources generally include di-n-butyl phthalate, diethyl phthalate, dimethyl phthalate, di(2-ethylhexyl) phthalate, diisobutyl phthalate, diisooctyl phthalate, etc. Further studies reveal that PAEs can be biosynthesized by at least several algae. PAEs are reported to possess allelopathic, antimicrobial, insecticidal, and other biological activities, which might enhance the competitiveness of plants, algae, and microorganisms to better accommodate biotic and abiotic stress. These findings suggest that PAEs should not be treated solely as a “human-made pollutant” simply because they have been extensively synthesized and utilized; on the other hand, synthesized PAEs entering the ecosystem might disrupt the metabolic process of certain plant, algal, and microbial communities. Therefore, further studies are required to elucidate the relevant mechanisms and ecological consequences.

Background: Observations of adverse developmental and reproductive effects in laboratory animals and wildlife have fueled increasing public concern regarding the potential for various chemicals to impair human fertility. Objective: Our objective in this study was to assess the effect of occupational exposure to high levels of phthalate esters on the balance of gonadotropin and gonadal hormones including luteinizing hormone, follicle-stimulating hormone, free testosterone (fT), and estradiol. Methods: We examined urine and blood samples of 74 male workers at a factory producing unfoamed polyvinyl chloride flooring exposed to di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) and compared them with samples from 63 male workers from a construction company, group matched for age and smoking status. Results: Compared to the unexposed workers, the exposed workers had substantially and significantly elevated concentrations of mono-n-butyl phthalate (MBP; 644.3 vs. 129.6 µg/g creatinine, p < 0.001) and mono-2-ethylhexyl phthalate (MEHP; 565.7 vs. 5.7 µg/g creatinine, p < 0.001). fT was significantly lower (8.4 vs. 9.7 µg/g creatinine, p = 0.019) in exposed workers than in unexposed workers. fT was negatively correlated to MBP (r = -0.25, p = 0.03) and MEHP (r = -0.19, p = 0.095) in the exposed worker group. Regression analyses revealed that fT decreases significantly with increasing total phthalate ester score (the sum of quartiles of MBP and MEHP; r = -0.26, p = 0.002). Conclusion: We observed a modest and significant reduction of serum fT in workers with higher levels of urinary MBP and MEHP compared with unexposed workers.

The chronic ecological risks posed by residual PAEs in China remain unclear. In this study, we analyzed the spatial distribution of five typical PAEs in the surface waters of China, dibutyl phthalate (DBP), diethylhexyl phthalate (DEHP), butylbenzyl phthalate (BBP), diethyl phthalate (DEP), and dimethyl phthalate (DMP). The highest concentration of PAEs were detected in the Liao River, ranging from 5 to 79.8 µg/L. DBP was of the PAEs type with the highest concentration in the surface waters in China. By fitting the species sensitivity distribution curves base on the collected data over the past decade, the chronically hazardous concentrations affecting 5% of the aquatic species were calculated to be 0.018, 0.022, 0.062, 0.851, and 9.437 mg/L for DBP, DEHP, BBP, DEP, and DMP, respectively. Thus, DBP, DEHP, and BBP pose the greatest threat to aquatic organisms, and PAEs pose high ecological risks in the Liao, Huangpu, and Pearl Rivers.

Phthalic acid esters (PAEs) are compounds that are used in the bottle as the main plasticizers. Therefore, the possibility of releasing phthalate esters into beverages is very high and there is a concern to consumer health and monitoring organizations. The aim of this research was to assess the phthalic acid esters (di-n-octyl phthalate (DNOP), butyl benzyl phthalate (BBP), dimethyl phthalate (DMP), diethyl phthalate (DEP) and dibutyl phthalate (DBP), bis(di-ethylhexyl) phthalate (DEHP), and total PAEs) in bottled non-alcoholic malt beverages ( n = 120) by multi-walled carbon nanotubes were magnetized with iron (MWCNT-Fe 3 O 4 ) using gaschromatography/mass spectrometry (GC-MS). The results showed that the highest and the lowest levels of total phthalate esters in samples were 9483.93 and 2412.50 ng/L, respectively. The mean of DEHP which has also been found to be carcinogenic in all samples was lower than 5944.73 ng/L. The highest concentration of DEHP in four samples was upper than 8957.87 ng/L. Perceived limit of detection (LOD) ranged from 13 to 30 ng/L and the limit of quantification (LOQ) ranged from 39 to 90 ng/L. Multivariate techniques and heat map visualization were used to assess the correlation among the type and levels of PAEs with the brand, color, product date, pH, sugar, volume, and gas pressure. Therefore, based on heat map and principal component analysis (PCA) results, the DEHP and total PAEs were the closest accessions, indicating that these variables had similar trends. Based on the results, it can be stated that due to the low average of total phthalate esters in non-alcoholic malt beverages, there is no serious health hazard of these compounds for humans.

Objective: We previously demonstrated that among 54 infants in neonatal intensive care units, exposure to polyvinyl chloride plastic medical devices containing the plasticizer di(2-ethylhexyl) phthalate (DEHP) is associated with urinary concentrations of mono(2-ethylhexyl) phthalate (MEHP), a DEHP metabolite. In this follow-up report, we studied the neonates' exposure to DEHP-containing devices in relation to urinary concentrations of two other DEHP metabolites, and to urinary concentrations of metabolites of dibutyl phthalate (DBP) and benzylbutyl phthalate (BzBP), phthalates found in construction materials and personal care products. Measurements: A priori, we classified the intensiveness of these 54 infants' exposure to DEHP-containing medical products. We measured three metabolites of DEHP in infants' urine: MEHP and two of its oxidative metabolites, mono(2-ethyl-5-hydroxylhexyl) phthalate (MEHHP) and mono(2-ethyl-5-oxohexyl) phthalate (MEOHP). We also measured monobutyl phthalate (MBP), a metabolite of DBP, and monobenzyl phthalate (MBzP), a metabolite of BzBP. Results: Intensiveness of DEHP-containing product use was monotonically associated with all three DEHP metabolites. Urinary concentrations of MEHHP and MEOHP among infants in the high-DEHP-intensiveness group were 13-14 times the concentrations among infants in the low-intensiveness group (p ≤ 0.007). Concentrations of MBP were somewhat higher in the medium- and high-DEHP-intensiveness group; MBzP did not vary by product use group. Incorporating all phthalate data into a structural equation model confirmed the specific monotonic association between intensiveness of product use and biologic measures of DEHP. Conclusion: Inclusion of the oxidative metabolites MEHHP and MEOHP strengthened the association between intensiveness of product use and biologic indices of DEHP exposure over that observed with MEHP alone.

Phthalates are often used as plasticizers in the production of plastic food contact materials (FCMs) and pharmaceutical contact materials (PCMs), and having in mind that they are not bound to plastics, phthalates may easily leach from plastics under certain conditions. The aim of this research is determination of phthalates leaching potential from different plastic materials and quantitative determination of 5 phthalates (dimethyl phthalate (DMP), di-n-butyl phthalate (DnBP), benzyl butyl phthalate (BBP), diethyl hexyl phthalate (DEHP), and di-n-octyl phthalate (DOP)) in 44 different plastic articles of 7 different plastic polymers used as FCMs and PCMs by FTIR, GC-MS, and gravimetric methods. The FTIR technique is shown to be rapid method for determination of phthalate content in PVC articles. Comparing of FTIR method with GC-MS and gravimetric showed that separation and quantitative determination of each phthalate separately favor the GC-MS method, because FTIR method determines the total amount of phthalate content. However, the FTIR method is less expensive and demanding in terms of sample preparation, which is suited for use in pre-screening analysis. The results of GC-MS phthalates determination showed that PVC articles used as PCMs contain DEHP in significant amount, from 5.19 to 28.76% by weight and could be a potential risk to human health.

Diet is an important exposure pathway of phthalate esters (PAEs) for humans. A total of 174 food samples covering 11 food groups were collected from Xi'an, a typical valley city in Northwest China, and analyzed to assess the occurrence and exposure risks for PAEs in the food. Twenty-two PAEs were detected. The sum of the 22 PAEs (∑22PAEs) varied between 0.0340 and 56.8 µg/g, with a mean of 3.94 µg/g. The major PAEs were di-iso-butyl phthalate (DiBP), di-n-butyl phthalate (DnBP), bis(2-ethylhexyl) phthalate (DEHP), di-iso-nonyl phthalate (DiNP), and di-iso-decyl phthalate (DiDP), which were associated mainly with the usage of plasticizers. Bio-availability of the PAEs in the combined gastro-intestinal fluid simulant of digestion was higher than that in the single gastric or intestinal fluid simulant. Bis(2-methoxyethyl) phthalate exhibited the highest bio-availability in each of the three simulants. Bio-availability of the PAEs was negatively correlated with the molecular weight and octanol–water partition coefficient of the PAEs and positively correlated with the solubility and vapor pressure of the PAEs. The estimated daily intake (EDI) of PAEs based on national and municipal food consumption data was lower than the reference dose (RfD) of the United States Environmental Protection Agency and the tolerable dairy intake (TDI) of European Food Safety Authority (EFSA), except for the EDI of DnBP and DiBP being higher than the TDI of EFSA. Grains and vegetables were the major sources of human dietary exposure to PAEs. The hazardous quotient for human dietary exposure to PAEs was less than the critical value of 1 and the cancer risk of butyl benzyl phthalate and DEHP was in the range of 10 –11 -10 –6 , suggesting relatively low health risks. The results indicated that human exposure to DnBP, DiBP, DEHP, DiNP, and DiDP in food is considerable and a health concern.

Due to the increasing population of the world, the presence of harmful compounds, especially phthalate esters (PAEs), are one of the important problems of environmental pollution. These compounds are known as carcinogenic compounds and Endocrine-disrupting chemicals (EDCs) for humans. In this study, the occurrence of PAEs and the evaluation of its ecological risks were carried out in the Persian Gulf. Water samples were collected from two industrial sites, a rural site and an urban site. Samples were analyzed using magnetic solid phase extraction (MSPE) and gas chromatography-mass spectrometry (GC/MS) technique to measure seven PAEs including Di(2-ethylhexyl) phthalate (DEHP), butyl benzyl phthalate (BBP), diethyl phthalate (DEP), dibutyl phthalate (DBP), Dimethyl phthalate (DMP), di-n-octyl phthalate (DNOP), and Di-iso-butyl phthalate (DIBP). The BBP was not detected in any of the samples. The total concentration of six PAEs (Σ6PAEs) ranged from 7.23 to 23.7 μg/L, with a mean concentration of 13.7μg/L. The potential ecological risk of each target PAEs was evaluated by using the risk quotient (RQ) method in seawater samples, and the relative results declined in the sequence of DEHP >DIBP > DBP > DEP > DMP in examined water samples. DEHP had a high risk to algae, crustaceans and fish at all sites. While DMP and DEP showed lower risk for all mentioned trophic levels. The results of this study will be helpful for the implementation of effective control measures and remedial strategies for PAEs pollution in the Persian Gulf.

Prenatal phthalate exposure impairs testicular function and shortens anogenital distance (AGD) in male rodents. We present data from the first study to examine AGD and other genital measurements in relation to prenatal phthalate exposure in humans. A standardized measure of AGD was obtained in 134 boys 2-36 months of age. AGD was significantly correlated with penile volume (R = 0.27, p = 0.001) and the proportion of boys with incomplete testicular descent (R = 0.20, p = 0.02). We defined the anogenital index (AGI) as AGD divided by weight at examination [AGI = AGD/weight (mm/kg)] and calculated the age-adjusted AGI by regression analysis. We examined nine phthalate monoester metabolites, measured in prenatal urine samples, as predictors of age-adjusted AGI in regression and categorical analyses that included all participants with prenatal urine samples (n = 85). Urinary concentrations of four phthalate metabolites [monoethyl phthalate (MEP), mono-n-butyl phthalate (MBP), monobenzyl phthalate (MBzP), and monoisobutyl phthalate (MiBP)] were inversely related to AGI. After adjusting for age at examination, p-values for regression coefficients ranged from 0.007 to 0.097. Comparing boys with prenatal MBP concentration in the highest quartile with those in the lowest quartile, the odds ratio for a shorter than expected AGI was 10.2 (95% confidence interval, 2.5 to 42.2). The corresponding odds ratios for MEP, MBzP, and MiBP were 4.7, 3.8, and 9.1, respectively (all p-values < 0.05). We defined a summary phthalate score to quantify joint exposure to these four phthalate metabolites. The age-adjusted AGI decreased significantly with increasing phthalate score (p-value for slope = 0.009). The associations between male genital development and phthalate exposure seen here are consistent with the phthalate-related syndrome of incomplete virilization that has been reported in prenatally exposed rodents. The median concentrations of phthalate metabolites that are associated with short AGI and incomplete testicular descent are below those found in one-quarter of the female population of the United States, based on a nationwide sample. These data support the hypothesis that prenatal phthalate exposure at environmental levels can adversely affect male reproductive development in humans.

Phthalic acid esters are predominantly used as plasticizers and are industrially produced on the million ton scale per year. They exhibit endocrine-disrupting, carcinogenic, teratogenic, and mutagenic effects on wildlife and humans. For this reason, biodegradation, the major process of phthalic acid ester elimination from the environment, is of global importance. Here, we studied bacterial phthalic acid ester degradation at Saravan landfill in Hyrcanian Forests, Iran, an active disposal site with 800 tons of solid waste input per day. A di-n-butyl phthalate degrading enrichment culture was established from which Paenarthrobacter sp. strain Shss was isolated. This strain efficiently degraded 1 g L–1 di-n-butyl phthalate within 15 h with a doubling time of 5 h. In addition, dimethyl phthalate, diethyl phthalate, mono butyl phthalate, and phthalic acid where degraded to CO2, whereas diethyl hexyl phthalate did not serve as a substrate. During the biodegradation of di-n-butyl phthalate, mono-n-butyl phthalate was identified in culture supernatants by ultra-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight mass spectrometry. In vitro assays identified two cellular esterase activities that converted di-n-butyl phthalate to mono-n-butyl phthalate, and the latter to phthalic acid, respectively. Our findings identified Paenarthrobacter sp. Shss amongst the most efficient phthalic acid esters degrading bacteria known, that possibly plays an important role in di-n-butyl phthalate elimination at a highly phthalic acid esters contaminated landfill.