Measurements of octanol–air partition coefficients, vapor pressures and vaporization enthalpies of the (E) and (Z) isomers of the 2-ethylhexyl 4-methoxycinnamate as parameters of environmental impact assessment

Pegoraro, César Nicolás; Chiappero, Malisa S.; Montejano, Hernán A.

doi:10.1016/j.chemosphere.2015.07.035

Cited by 17 publications

(8 citation statements)

References 48 publications

(48 reference statements)

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“…RMSEs for the comparison between GC-RT estimates in this study and the literature for all compounds were 0.60 log unit for p L 298 /Pa and 0.65 for K OA 298 . Exceptions to this agreement included literature GC-RT values for TCiPP and octinoxate, which differed from GC-RT values estimated in this study by 1.40 to 1.64 log units. Bias for log 10 K OA 298 was higher than for log 10 p L 298 /Pa.…”

Section: Results and Discussioncontrasting

confidence: 96%

Gas Chromatographic Estimation of Vapor Pressures and Octanol–Air Partition Coefficients of Semivolatile Organic Compounds of Emerging Concern

et al. 2020

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The subcooled liquid-phase vapor pressures (p L 298 /Pa) and octanol−air partition coefficients (K OA 298 ) at T/K = 298, enthalpies of vaporization (Δ VAP H/kJ•mol −1 ), and internal energies of phase transfer from octanol to air (Δ OA U/kJ•mol −1 ) were estimated for synthetic musks, novel brominated flame retardants (N-BFR), organophosphate esters, and ultraviolet filters using the capillary gas chromatographic retention time (GC-RT) method. These compounds, which spanned approximately six and three orders of magnitude for p L 298 /Pa and K OA 298 , respectively, were co-chromatographed with one of three reference compounds to give initial estimates of properties at T/K = 298. The initial GC-RT property estimates were subsequently calibrated using 18 compounds that spanned 6 log units for p L 298 /Pa and 13 compounds covering 4 log units for K OA 298 . The calibrated log 10 p L 298 /Pa values estimated here ranged from 0.14 ± 0.19 to −9.19 ± 0.29 for cyclopentadecanone to syndechlorane plus (syn-DDC-CO), respectively, while the range of log 10 K OA 298 values was 6.59 ± 0.26 to 11.40 ± 0.23 for cyclopentadecanone to 2,2′,4,4′,5-pentabromodiphenyl ether (BDE-99), respectively. The calibrated GC-RT-derived values were highly correlated with, and were within an average of 0.70 log units of, the literature data for compounds with well-established p L 298 / Pa and K OA 298 measured or derived using non-GC-RT methods. Nonpolar compounds were used in this study to estimate the target polar compound data, which may introduce systematic errors. However, the comparison of our GC-RT results against the literature non-GC-RT values shows that the GC-RT methods performed similarly well for estimating both polar and nonpolar target compounds studied in this work.

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Section: Results and Discussioncontrasting

confidence: 96%

Gas Chromatographic Estimation of Vapor Pressures and Octanol–Air Partition Coefficients of Semivolatile Organic Compounds of Emerging Concern

et al. 2020

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“… a Maximum concentrations of drug medicinal ingredients in sunscreens (“Guidance Document Sunscreen Monograph,” Health Canada, 2012). b EPA EPI suite. c Pegoraro et al d Okeme et al e Pegoraro et al f MW = molecular weight, KOA = octanol–air partition coefficient, E = trans isomer, Z = cis isomer. …”

Section: Methodsmentioning

confidence: 99%

“…In fact, the atmospheric fate of organic UV-filters is relatively unknown. A recent assessment of their physical and chemical properties suggests that organic UV-filters are relatively persistent in air and are semivolatile compounds, which should exist both in the gas phase and associated with particles …”

Section: Introductionmentioning

confidence: 99%

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Occurrence and Gas–Particle Partitioning of Organic UV-Filters in Urban Air

Pegoraro

Harner

et al. 2020

Environ. Sci. Technol.

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A retrospective analysis of a comprehensive series of high-volume air samples (n = 70) collected during 2010−2011 in Toronto (Canada) was performed. Seven UV compounds were analyzed by gas chromatography−tandem mass spectrometry (GC−MS/MS) with sum of concentrations (gas + particle phase) ranging from 80 to 2030 pg/m 3 . Homosalate (HMS) was the most prevalent organic UV-filter in air (47% of the total concentration), followed by 2-ethylhexyl salicylate (EHS, ∼29%), E-and Z-2-ethylhexyl 4-methoxycinnamate (EHMC, ∼17%). Ambient air (gas + particle phase) concentrations of organic UVfilters showed a strong seasonality, with peak levels during the summer. An analysis of Clausius−Clapeyron slopes indicated that much of the ambient burden of organic UV-filters are explained by volatilization from terrestrial and aquatic surfaces and supplemented with human activities and use of lotions and sunscreens, containing organic UV-filters, in addition to its use in plastics, textiles, paints, and pesticides. The results showed that organic UVfilters exist mainly in the gas phase with some exceptions, for instance, octocrylene (OCR), which was associated with both gas and particle phases, and avobenzone (AVB), which was predominantly in the particle phase. Lastly, this study revealed the need for basic physical chemical property data for organic UV-filters, including information on transformation rates and products, for better evaluating their environmental fate and effects.

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“…In sunscreens, the OMC can be found only in E-OMC isomer (trans-isomer), while in other PCPs, it may be present in both isomers (E-OMC or Z-OMC) (Pegoraro et al 2015). This UV-B filter is photo-unstable because, when exposed to sunlight, OMC undergoes a photoisomerization of trans-isomer to cis-isomer as shown in Fig.…”

Section: Uv-b Filter Octylmethoxycinnamate Photoinstabilitymentioning

confidence: 99%

Antioxidants as stabilizers of UV filters: an example for the UV-B filter octylmethoxycinnamate

Lorigo

2019

biomed dermatol

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Background: Sunlight is one of the main harmful exogenous factors that induce the reactive oxygen species formation. The human skin is the first line of photoprotection against harmful exogenous factors, such as UV radiations. The topical application of sunscreens, containing UV-B filters, is widely used to protect against UV-induced damage. Octylmethoxycinnamate is the world's most widely used UV-B filter in sunscreens. However, recent studies have demonstrated that this substance is an endocrine disruptor compound and with potential to damage DNA. Thus, the safety of this organic filter is a current concern for human health, and it was urgent to develop new photoprotective strategies. In this sense, due to the potential to neutralize the UV-induced free radicals, the use of antioxidants as UV filter stabilizers presented as a novel promising strategy. Research: The purpose of this review was to assess the use of antioxidants as stabilizers for UV-B filter octylmethoxycinnamate. For this, we discuss the chemical and physical characteristics of UV-B filter octylmethoxycinnamate, emphasizing the stability, photostability, and reactivity of this UV filter. The use of antioxidants in sunscreens will also be addressed, from a perspective of the main characteristics that allowed their use in sunscreen formulations. Then, the concomitant use of both was described from a historical and physical chemical perspective, always emphasizing the advantages and disadvantages of this association. Conclusions: The combination of antioxidants with UV-B filter octylmethoxycinnamate in appropriated formulations represents a viable strategy to protect the human skin against UV-induced damage.

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Measurements of octanol–air partition coefficients, vapor pressures and vaporization enthalpies of the (E) and (Z) isomers of the 2-ethylhexyl 4-methoxycinnamate as parameters of environmental impact assessment

Cited by 17 publications

References 48 publications

Gas Chromatographic Estimation of Vapor Pressures and Octanol–Air Partition Coefficients of Semivolatile Organic Compounds of Emerging Concern

Gas Chromatographic Estimation of Vapor Pressures and Octanol–Air Partition Coefficients of Semivolatile Organic Compounds of Emerging Concern

Occurrence and Gas–Particle Partitioning of Organic UV-Filters in Urban Air

Antioxidants as stabilizers of UV filters: an example for the UV-B filter octylmethoxycinnamate

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