Bioaccumulation and ecotoxicity increase during indirect photochemical transformation of polycyclic musk tonalide: A modeling study

Gao, Yanpeng; Ji, Yuemeng; Li, Guiying; Mai, Bi-Xian; An, Taicheng

doi:10.1016/j.watres.2016.08.055

Cited by 47 publications

(13 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the present work, quantum chemical calculations were performed using the Gaussian 09 package (35). The solvent effect of water in the aqueous phase was considered by a continuum solvation model (SMD) (36,37). The solvation free energy included two main components, including the bulk electrostatic contribution and cavity-dispersion-solvent-structure contribution from short-range interactions between the solute and solvent molecules (37).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Carbenium ion-mediated oligomerization of methylglyoxal for secondary organic aerosol formation

Shi

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

Secondary organic aerosol (SOA) represents a major constituent of tropospheric fine particulate matter, with profound implications for human health and climate. However, the chemical mechanisms leading to SOA formation remain uncertain, and atmospheric models consistently underpredict the global SOA budget. Small α-dicarbonyls, such as methylglyoxal, are ubiquitous in the atmosphere because of their significant production from photooxidation of aromatic hydrocarbons from traffic and industrial sources as well as from biogenic isoprene. Current experimental and theoretical results on the roles of methylglyoxal in SOA formation are conflicting. Using quantum chemical calculations, we show cationic oligomerization of methylglyoxal in aqueous media. Initial protonation and hydration of methylglyoxal lead to formation of diols/tetrol, and subsequent protonation and dehydration of diols/tetrol yield carbenium ions, which represent the key intermediates for formation and propagation of oligomerization. On the other hand, our results reveal that the previously proposed oligomerization via hydration for methylglyoxal is kinetically and thermodynamically implausible. The carbenium ion-mediated mechanism occurs barrierlessly on weakly acidic aerosols and cloud/fog droplets and likely provides a key pathway for SOA formation from biogenic and anthropogenic emissions.

show abstract

Section: Methodsmentioning

confidence: 99%

“…The structural parameters of all possible ionic reaction pathways are summarized in SI Appendix, Table S3. Based on the above PES information, the reaction kinetics were calculated using conventional TST, solvent cage effects (36), and diffusion-limited effects (29), as shown in SI Appendix.…”

Section: Methodsmentioning

confidence: 99%

Carbenium ion-mediated oligomerization of methylglyoxal for secondary organic aerosol formation

Shi

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Limonene is employed in degreasing metals before industrial painting, for cleaning in electronic and painting industries, in paint products as solvent and in many household cleaning detergents (Filipsson et al 1998). The widespread use of synthetic musks leads to their release in large amounts through discharges of wastewater treatment plants (WWTPs) into the environment (Santiago-Morales et al 2012;Gao et al 2016). These compounds are persistent and therefore can be accumulated in sediments and in lipid tissues of aquatic organisms (Daughton and Ternes 1999;Reiner and Kannan 2011).…”

Section: Introductionmentioning

confidence: 99%

Polycyclic musk fragrances (PMFs) in wastewater and activated sludge: analytical protocol and application to a real case study

Tasselli

Guzzella

2020

Environ Sci Pollut Res

View full text Add to dashboard Cite

Two different analytical methods for the determination of polycyclic musk fragrances (PMFs) in wastewater and in activated sludge were developed. PMFs in filtered water samples were determined by gas chromatography coupled with a triplequadrupole mass spectrometer in selected reaction monitoring (SRM) mode. Activated sludge samples were extracted using an ultrasonic bath and analysed using a GC-Ion trap. The developed methods respected a linear model (R 2 > 0.995). Detection limits of selected compounds (Celestolide, Galaxolide, Galaxolidone, Phantolide and Tonalide) varied from 1.7 to 80 ng L −1 for water and from 0.1 ng g −1 to 210 ng g −1 for activated sludge considering laboratory contamination for each PMF. Recovery studies were performed on spiked water samples and, for sludges, on procedural blanks, showing recoveries above 70% for all the considered compounds, while recovery of the internal standard was always above limit of acceptance (30%). Proposed methods were used to determine PMFs concentrations in wastewaters and activated sludges of a wastewater treatment plant (WWTP) located in Northern Italy. Concentrations in the range of μg L −1 of Galaxolide and of its metabolite Galaxolidone were detected even in the WWTP effluent. Biotransformation of Galaxolide into Galaxolidone occurred during biological treatment with the consequent release of this compound through WWTP effluents. In activated sludges, concentrations of all PMFs except Galaxolidone were one order of magnitude higher than wastewaters, as expected according to their physicochemical properties. Present wastewater treatment technologies were confirmed to not be efficient in removing PMFs from influent wastewaters since with only ≃ 30% of Celestolide and Tonalide were removed.

show abstract

“…22,23 For example, Fang et al 22 reported that tonalide (AHTN) can act as a photosensitizer to increase photo-induced oxidative damage to natural amino acid on skin surfaces. Gao et al 24 reported that indirect photochemical transformation products of AHTN in water could have up to 8 times higher bioconcentration factor than parent AHTN. Quantitative Structure Activity Relationships (QSAR)-based risk assessment indicated that HHCB could pose a risk to biota exposed through sediment, soil, water and in some cases air by Homem et al 25 These potential effects of PCMs, when combined with their propensity to bioaccumulate due to their high lipophilicity (log K OW $ 4.5-7.0, Table 1), have led to concern about their long-term human and environmental health effects.…”

Section: Introductionmentioning

confidence: 99%

Urban sources of synthetic musk compounds to the environment

Wong

Robson

Melymuk

et al. 2019

Environ. Sci.: Processes Impacts

View full text Add to dashboard Cite

show abstract

Bioaccumulation and ecotoxicity increase during indirect photochemical transformation of polycyclic musk tonalide: A modeling study

Cited by 47 publications

References 55 publications

Carbenium ion-mediated oligomerization of methylglyoxal for secondary organic aerosol formation

Carbenium ion-mediated oligomerization of methylglyoxal for secondary organic aerosol formation

Polycyclic musk fragrances (PMFs) in wastewater and activated sludge: analytical protocol and application to a real case study

Urban sources of synthetic musk compounds to the environment

Contact Info

Product

Resources

About