First Report on the Occurrence of N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and 6PPD-Quinone as Pervasive Pollutants in Human Urine from South China

Environmental Science & Technology Letters, Journal Year: 2022, Volume and Issue: 9(12), P. 1056 - 1062

Published: Nov. 21, 2022

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and its quinone derivative, 6PPD-quinone (6PPD-Q), have been found to be prevalent in the environment, but there are currently no data on their presence humans. Herein, we conducted first human biomonitoring study of 6PPD 6PPD-Q by measuring 150 urine samples collected from three different populations (general adults, children, pregnant women) South China. Both were detected samples, with detection frequencies between 60% 100%. Urinary concentrations significantly higher than those correlated well (p < 0.01), indicating coexposure In vitro metabolic experiments demonstrated rapid depletion liver microsomes, which should responsible for lower urine. Additionally, women exhibited apparently (median 0.068 2.91 ng/mL, respectively) did adults (0.018 0.40 ng/mL) children (0.015 0.076 ng/mL). The high daily urinary excretion was estimated 273 (ng/kg bw)/day. Considering that a lethal toxicant multiple aquatic species, potential health risks posed long-term exposure require urgent attention.

Language: Английский

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Widespread Occurrence and Transport of p-Phenylenediamines and Their Quinones in Sediments across Urban Rivers, Estuaries, Coasts, and Deep-Sea Regions

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(6), P. 2393 - 2403

Published: Jan. 31, 2023

p-Phenylenediamines (PPDs) are widely used as antioxidants in tire rubber, and their derived quinone transformation products (PPD-Qs) may pose a threat to marine ecosystems. A compelling example is N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD)-derived quinone, called 6PPD-Q, the causal toxicant for stormwater-linked acute mortality toward coho salmon. However, knowledge of co-occurrences PPDs PPD-Qs transport from freshwater oceanic waterbodies on large geographical scale remains unknown. Herein, we performed first large-scale survey these chemicals sediments across urban rivers, estuaries, coasts, deep-sea regions. Our results demonstrated that seven four ubiquitously present riverine, estuarine, coastal sediments, most them also occur sediments. The dominant concern were identified 6PPD 6PPD-Q. Total sedimentary concentrations presented clear spatial trend with decreasing levels rivers (medians: 39.7 15.2 ng/g) estuaries (14.0 5.85 then coasts (9.47 2.97 regions (5.24 3.96 ng/g). Interestingly, variation ratios 6PPD-Q (R6PPD/6PPD-Q) trend. field measurements implied riverine outflows be an important route rubber-derived open oceans.

Language: Английский

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Analysis, environmental occurrence, fate and potential toxicity of tire wear compounds 6PPD and 6PPD-quinone

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 452, P. 131245 - 131245

Published: March 21, 2023

Language: Английский

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Tire-rubber related pollutant 6-PPD quinone: A review of its transformation, environmental distribution, bioavailability, and toxicity

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 459, P. 132265 - 132265

Published: Aug. 15, 2023

Language: Английский

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6PPD and its metabolite 6PPDQ induce different developmental toxicities and phenotypes in embryonic zebrafish

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 455, P. 131601 - 131601

Published: May 8, 2023

Language: Английский

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Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(14), P. 5621 - 5632

Published: March 30, 2023

6PPD, a tire rubber antioxidant, poses substantial ecological risks because it can form highly toxic quinone transformation product (TP), 6PPD-quinone (6PPDQ), during exposure to gas-phase ozone. Important data gaps exist regarding the structures, reaction mechanisms, and environmental occurrence of TPs from 6PPD ozonation. To address these gaps, ozonation was conducted over 24–168 h were characterized using high-resolution mass spectrometry. The probable structures proposed for 23 with 5 subsequently standard-verified. Consistent prior findings, 6PPDQ (C18H22N2O2) one major in (∼1 19% yield). Notably, not observed 6QDI (N-(1,3-dimethylbutyl)-N′-phenyl-p-quinonediimine), indicating that formation does proceed through or associated TPs. Other included multiple C18H22N2O C18H22N2O2 isomers, presumptive N-oxide, N,N′-dioxide, orthoquinone structures. Standard-verified quantified roadway-impacted samples, total concentrations 130 ± 3.2 μg/g methanol extracts tread wear particles (TWPs), 34 4 μg/g-TWP aqueous TWP leachates, 2700 1500 ng/L roadway runoff, 1900 1200 creeks. These demonstrate are likely an important ubiquitous class contaminants environments.

Language: Английский

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Screening p-Phenylenediamine Antioxidants, Their Transformation Products, and Industrial Chemical Additives in Crumb Rubber and Elastomeric Consumer Products

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(7), P. 2779 - 2791

Published: Feb. 9, 2023

Recently, roadway releases of

Language: Английский

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Environmental Occurrence and Toxicity of 6PPD Quinone, an Emerging Tire Rubber-Derived Chemical: A Review

Environmental Science & Technology Letters, Journal Year: 2023, Volume and Issue: 10(10), P. 815 - 823

Published: Sept. 1, 2023

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) is a chemical added to tires prevent their oxidative degradation. 6PPD highly reactive with ozone and oxygen, leading the formation of transformation products such as quinone (6PPDQ) on tire surfaces and, subsequently, in road wear particles. 6PPDQ toxicant that has been found roadway runoff receiving water systems. Its presence municipal stormwater led acute mortality coho salmon during migration urban creeks reproduce, generating global interest studying its occurrence toxicity environment. This review aims provide critical overview current state knowledge 6PPDQ, assisting researchers policymakers understanding potential impacts this emerging environment human health. As there are many unanswered questions surrounding further research needed. highlights importance including regulations for 6PPD, well all synthetic chemicals concern.

Language: Английский

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Urine Excretion, Organ Distribution, and Placental Transfer of 6PPD and 6PPD-Quinone in Mice and Potential Developmental Toxicity through Nuclear Receptor Pathways

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(36), P. 13429 - 13438

Published: Aug. 29, 2023

The rubber antioxidant 6PPD has gained significant attention due to its highly toxic transformation product, 6PPD-quinone (6PPDQ). Despite their detection in urines of pregnant women, the placental transfer and developmental toxicity 6PPDQ are unknown. Here, we treated C57Bl/6 mice with 4 mg/kg or investigate urine excretion transfer. Female male exhibited sex difference profiles 6PPDQ. Urine concentrations were one order magnitude lower than those 6PPD, suggesting higher bioaccumulation In from embryonic day 11.5 15.5, showed ∼1.5–8 times placenta, embryo body, brain, Using vitro dual-luciferase reporter assays, revealed that activated human retinoic acid receptor α (RARα) retinoid X (RXRα) at as low 0.3 μM, which was ∼10-fold detected urines. RXRα 1.2 μM. These results demonstrate exposure risks during pregnancy emphasize need for further toxicological epidemiological investigations.

Language: Английский

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Uptake and Biotransformation of the Tire Rubber-derived Contaminants 6-PPD and 6-PPD Quinone in the Zebrafish Embryo (Danio rerio)

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(41), P. 15598 - 15607

Published: Oct. 2, 2023

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6-PPD) is a widely used antioxidant in tire rubber known to enter the aquatic environment via road runoff. The associated transformation product (TP) 6-PPD quinone (6-PPDQ) causes extreme acute toxicity some fish species (e.g., coho salmon). To interpret species-specific toxicity, information about biotransformation products of 6-PPDQ would be relevant. This study investigated toxicokinetics and zebrafish embryo (ZFE) model. Over 96 h exposure, accumulated ZFE with concentration factors ranging from 140 2500 for 70 220 6-PPDQ. A total 22 TPs 12 were tentatively identified using liquid chromatography coupled high-resolution mass spectrometry. After exposure 6-PPD, comprised 47% peak area (TPA), 4-hydroxydiphenylamine being most prominent ZFE. Upon >95% taken up was biotransformed, + O glucuronide dominating (>80% TPA). Among other reactive N-phenyl-p-benzoquinone imine found. knowledge this may support studies organisms.

Language: Английский

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