Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant α-Pinene Oxidation Products

Kołodziejczyk, Agata; Pyrcz, Patryk; Błaziak, Kacper; Pobudkowska, Aneta; Sarang, Kumar; Szmigielski, Rafał

doi:10.1021/acsomega.9b04231

Cited by 14 publications

(13 citation statements)

References 43 publications

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“…Consequently, the temperature at which the first peak appeared is referred to as the melting temperature ( T m ). In this study, the T m values for 3-MBTCA, terpenylic acid, DTAA, and 1,2,4-B3CA were found to be 136.1, 81.3, 110.6, and 219.7 °C, respectively, which were comparable to previously reported ranges: 144–149.6, 92–94, 121.1, and 229–231 °C, respectively. ,− In heat flow profiles of 3-MBTCA, DTAA, and 1,2,4,5-B4CA, two endothermic peaks were found in addition to the last peak, at which the sample vaporized completely. For the case of 3-MBTCA, DTAA, and 1,2,4,5-B4CA, the first endothermic peaks were found at 30.4, 111.7, and 58.1 °C, respectively, with a slight decrease in mass as evident in the corresponding TGA thermograms.…”

Section: Resultssupporting

confidence: 86%

“…TGA and DSC recorded the change in mass and the difference in energy supplied to reference and sample pans as a function of the temperature. DSC is a well-established technique to analyze the phase transition processes such as melting point, crystallization, and decomposition of chemical species. ,− DSC analysis was utilized to determine the melting temperatures ( T m ) of the aforementioned chemical species. In each analysis, two aluminum pans were utilized.…”

Section: Materials and Methodsmentioning

confidence: 99%

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Exploring Volatility Properties of Discrete Secondary Organic Aerosol Constituents of α-Pinene and Polycyclic Aromatic Hydrocarbons

Babar

Ashraf

Park

et al. 2020

ACS Earth Space Chem.

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Limited experimental data are available on the volatility parameters of saturation vapor pressure, vaporization enthalpy, and melting temperature of secondary organic aerosol (SOA) constituents. In this study, we aimed to determine the volatility of individual components of typical biogenic and anthropogenic SOA. The volatility profiles of four synthesized and two commercial SOA constituents were generated using a thermal denuder coupled with a scanning particle sizer. For the volatility measurement, four constituents of α-pinene SOA were synthesized in the laboratory because of the lack of commercial reagents. For each of the SOA species, a volatility profile was measured by changing the thermal denuder temperature below its melting point measured using thermal gravimetric analysis and differential scanning calorimetry. Saturation pressure (P sat 0) and vaporization enthalpy (ΔH v) at 25 °C of the SOA constituents were determined by applying the integrated volume method to the measured volatility profiles. The determined P sat 0 values of 3-methylbutane-1,2,3-tricarboxylic acid (3-MBTCA), terpenylic acid, diaterpenylic acid acetate (DTAA), sodium-(1R,2R,3S,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl sulfate (Na-2-OH-2,6,6-TMBHS), 1,2,4,5-benzenetetracarboxylic acid (1,2,4,5-B4CA), and 1,2,4-benzenetricarboxylic acid (1,2,4-B3CA) were 3.4 ± 0.6 × 10–5, 1.7 ± 0.3 × 10–4, 1.8 ± 0.2 × 10–5, 3.4 ± 0.4 × 10–5, 7.7 ± 0.7 × 10–5, and 2.1 ± 0.3 × 10–6 Pa, respectively. The estimated values of ΔH v for 3-MBTCA, terpenylic acid, DTAA, Na-2-OH-2,6,6-TMBHS, 1,2,4,5-B4CA, and 1,2,4-B3CA were 128.4 ± 4.7, 88.4 ± 3.5 135.4 ± 3.7, 38.4 ± 1.7, 42.8 ± 2.1, and 108.1 ± 4.1 kJ mol–1, respectively. These data will improve the knowledge of the formation and fate of SOA.

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Section: Resultssupporting

confidence: 86%

Section: Materials and Methodsmentioning

confidence: 99%

Exploring Volatility Properties of Discrete Secondary Organic Aerosol Constituents of α-Pinene and Polycyclic Aromatic Hydrocarbons

Babar

Ashraf

Park

et al. 2020

ACS Earth Space Chem.

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“…MBTCA (3-methyl-1,2,3-butanetricarboxylic acid, 99% purity) and cis -pinic acid (99.5% purity) were synthesized in our laboratory, as described previously. , α-Pinene (>99% purity), cis -pinonic acid (98% purity), dimethyl sulfoxide (DMSO, MolBio-Grade), Dulbecco’s phosphate-buffered saline (PBS), methanol (ChromaSolv-Grade), and 0.1% acetic acid were purchased from Sigma-Aldrich (Merck, Poland). High-purity methanol (optima LC/MS grade) was purchased from Fisher Chemical (U.S.A.).…”

Section: Methodsmentioning

confidence: 99%

Toxicological Responses of α-Pinene-Derived Secondary Organic Aerosol and Its Molecular Tracers in Human Lung Cell Lines

Khan

Kwapiszewska

Zhang

et al. 2021

Chem. Res. Toxicol.

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Secondary organic aerosol (SOA) is a major component of airborne fine particulate matter (PM 2.5 ) that contributes to adverse human health effects upon inhalation. Atmospheric ozonolysis of α-pinene, an abundantly emitted monoterpene from terrestrial vegetation, leads to significant global SOA formation; however, its impact on pulmonary pathophysiology remains uncertain. In this study, we quantified an increasing concentration response of three well-established α-pinene SOA tracers (pinic, pinonic, and 3-methyl-1,2,3-butanetricarboxylic acids) and a full mixture of α-pinene SOA in A549 (alveolar epithelial carcinoma) and BEAS-2B (bronchial epithelial normal) lung cell lines. The three aforementioned tracers contributed ∼57% of the α-pinene SOA mass under our experimental conditions. Cellular proliferation, cell viability, and oxidative stress were assessed as toxicological end points. The three α-pinene SOA molecular tracers had insignificant responses in both cell types when compared with the α-pinene SOA (up to 200 μg mL –1 ). BEAS-2B cells exposed to 200 μg mL –1 of α-pinene SOA decreased cellular proliferation to ∼70% and 44% at 24- and 48-h post exposure, respectively; no changes in A549 cells were observed. The inhibitory concentration-50 (IC 50 ) in BEAS-2B cells was found to be 912 and 230 μg mL –1 at 24 and 48 h, respectively. An approximate 4-fold increase in cellular oxidative stress was observed in BEAS-2B cells when compared with untreated cells, suggesting that reactive oxygen species (ROS) buildup resulted in the downstream cytotoxicity following 24 h of exposure to α-pinene SOA. Organic hydroperoxides that were identified in the α-pinene SOA samples likely contributed to the ROS and cytotoxicity. This study identifies the potential components of α-pinene SOA that likely modulate the oxidative stress response within lung cells and highlights the need to carry out chronic exposure studies on α-pinene SOA to elucidate its long-term inhalation exposure effects.

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“…The contribution of SOA to the Earth’s solar radiative budget, climate change, and cloud formation, as well as its impact on human health through gas- and aqueous-phase processes, have been progressively investigated. − Still, however, the vast fraction of potentially important SOA sources and transformation processes remain unknown. ,, Hydrophilic aerosol particles serve as Cloud Condensation Nuclei (CCN) and promote cloud formation playing a significant role in cooling the Earth’s climate . Among biogenic VOCs (BVOCs), isoprene − and monoterpenes − have already gained ample attention, while green leaf volatiles (GLVs), also potentially precursors of SOA, have been much less studied.…”

Section: Introductionmentioning

confidence: 99%

Reaction Kinetics of Green Leaf Volatiles with Sulfate, Hydroxyl, and Nitrate Radicals in Tropospheric Aqueous Phase

Sarang

Otto

Rudziński

et al. 2021

Environ. Sci. Technol.

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Green plants exposed to abiotic or biotic stress release C-5 and C-6 unsaturated oxygenated hydrocarbons called Green Leaf Volatiles (GLVs). GLVs partition into tropospheric waters and react to form secondary organic aerosol (SOA). We explored the kinetics of aqueous-phase reactions of 1-penten-3-ol (PENTOL), (Z)-2-hexen-1-ol (HEXOL), and (E)-2-hexen-1-al (HEXAL) with SO4 •–, •OH, and NO3 •. At 298 K, the rate constants for reactions of PENTOL, HEXOL, and HEXAL with SO4 •– were, respectively, (9.4 ± 1.0) × 108 L mol–1 s–1, (2.5 ± 0.3) × 109 L mol–1 s–1, and (4.8 ± 0.2) × 108 L mol–1 s–1; with •OH – (6.3 ± 0.1) × 109 L mol–1 s–1, (6.7 ± 0.3) × 109 L mol–1 s–1, and (4.8 ± 0.3) × 109 L mol–1 s–1; and with NO3 • – (1.5 ± 0.15) × 108 L mol–1 s–1, (8.4 ± 2.3) × 108 L mol–1 s–1, and (3.0 ± 0.7) × 107 L mol–1 s–1. The rate constants increased weakly with temperatures ranging from 278 to 318 K. The diffusional limitations of the rate constants appeared significant only for the GLV–•OH reactions. The aqueous-phase reactions appeared negligible in deliquescent aerosol and haze water but not in clouds and rains. The atmospheric lifetimes of GLVs decreased from many days to hours with increasing liquid water content and radicals’ concentration.

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Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant α-Pinene Oxidation Products

Cited by 14 publications

References 43 publications

Exploring Volatility Properties of Discrete Secondary Organic Aerosol Constituents of α-Pinene and Polycyclic Aromatic Hydrocarbons

Exploring Volatility Properties of Discrete Secondary Organic Aerosol Constituents of α-Pinene and Polycyclic Aromatic Hydrocarbons

Toxicological Responses of α-Pinene-Derived Secondary Organic Aerosol and Its Molecular Tracers in Human Lung Cell Lines

Reaction Kinetics of Green Leaf Volatiles with Sulfate, Hydroxyl, and Nitrate Radicals in Tropospheric Aqueous Phase

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