A fast and efficient method for the analysis of α-dicarbonyl compounds in aqueous solutions: Development and application

Brun, Nicolas; González-Sánchez, Juan Miguel; Demelas, Carine; Clément, Jean‐Louis; Monod, Anne

doi:10.1016/j.chemosphere.2023.137977

Cited by 11 publications

(8 citation statements)

References 51 publications

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“…Evaporation of the solvent allowed us to obtain 57% of the desired pure product as a pale-yellow oil. Spectroscopic analyses of 1-nitrooxy-2-propanone (A2) CAS [6745-71-7] and 3-nitrooxy-2-butanone (B2) CAS [124855-10-3] revealed that they are identical to already published data. , …”

Section: Experimental Sectionsupporting

confidence: 54%

Gas-Phase Photolysis and Photo-Oxidation of Isoprene-Derived Atmospherically Relevant Hydroxy Nitrates

Verma,

Zgheib,

Perrier

et al. 2024

ACS EST Air

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Volatile organic compounds (VOCs), released from both natural and anthropogenic activities, undergo oxidation in the atmosphere to form alkyl peroxy radicals (RO2) that, through subsequent chemistry, form a variety of oxygenated species that may impact both air quality and climate. Among the potential oxygenated species formed are organic nitrates (ON) that can be transported over long distances and contribute to ozone production and particle formation. The atmospheric lifetime of an ON is influenced by its molecular structure. The ON structure impacts both further gas phase reaction (e.g., photolysis and photo-oxidation with OH radical reaction) and gas-to-particle partitioning that may result in multiphase chemistry (e.g., hydrolysis) and secondary organic aerosol (SOA) formation. This study investigates the photo-oxidation of two atmospheric-relevant ON, specifically, hydroxy nitrates, 2-methyl-1-nitrooxy-3-buten-2-ol (C5H9NO4, secondary -ONO2, C5-ON), and 3-methyl-2-nitrooxy-4-penten-3-ol (C6H11NO4, tertiary -ONO2, C6-ON). Significant differences in their reactivity are demonstrated, and the C5-ON underwent faster photolysis, while the C6-ON was more resistant to photolysis, whereas the C6-ON underwent faster degradation during OH-initiated photo-oxidation. These differences in reactivity are attributed to the presence of the extra methyl group on C6-ON. Furthermore, oxidation products that demonstrate the complexity of the reaction processes were detected by chemical ionization Orbitrap mass spectrometry operated in negative mode. Notably, cleavage of the O–N bond and subsequent alkoxy radical chemistry is the dominant pathway during photolysis, whereas OH addition followed by RO2 bimolecular reactions (i.e., RO2 + RO2 or HO2) is the dominant pathway during OH oxidation. This research sheds light on the intricate chemistry of organic nitrates in the atmosphere, emphasizing the role of the molecular structure on their fate.

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Section: Experimental Sectionsupporting

confidence: 54%

Gas-Phase Photolysis and Photo-Oxidation of Isoprene-Derived Atmospherically Relevant Hydroxy Nitrates

Verma,

Zgheib,

Perrier

et al. 2024

ACS EST Air

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“…(MGO), diacetyl (DA), and pentanedione (PD), and so on [1,2]. α-DCs are mainly produced during food heating treatment containing frying and baking [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

“…α‐Dicarbonyl compounds (α‐DCs) are a series of highly reactive intermediates, such as d ‐glucosone (DS), 3‐deoxyglucosone (3‐DG), glyoxal (GO), methylglyoxal (MGO), diacetyl (DA), and pentanedione (PD), and so on [1, 2]. α‐DCs are mainly produced during food heating treatment containing frying and baking [3–5].…”

Section: Introductionmentioning

confidence: 99%

Simultaneous determination of six α‑dicarbonyl compounds in traditional Chinese medicines using high‐performance liquid chromatography‐fluorescence detector with pre‐column derivatization

Xu,

Yin,

Liu

et al. 2023

J of Separation Science

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A reliable method for determination of six α‐dicarbonyl compounds in traditional Chinese medicines was first developed and validated by high‐performance liquid chromatography‐fluorescence detector with pre‐column derivatization. α‐Dicarbonyl compounds in traditional Chinese medicines were extracted and derivatized with 2,3‐diaminaphthalene. The derivatization procedure of six α‐dicarbonyl compounds was confirmed by high‐resolution mass spectrometry. The limits of quantitation for six α‐dicarbonyl compounds ranged from 3.70 × 10−3 to 2.21 × 10−2 μM. The established method showed good linearity (regression coefficient > 0.9990), precision (relative standard deviation < 3.37%), and high recovery (97.8%∼113.1%). The developed method was successfully applied to detect the six α‐dicarbonyl compounds in traditional Chinese medicines. The result exhibited six α‐dicarbonyl compounds was found in the 15 kinds of traditional Chinese medicines, which suggested us that the determination of α‐dicarbonyl compounds should be paid more attention in the quality control of traditional Chinese medicines.

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“…On the other hand, they are not retained by the most common chromatography variants owing to their hydrophilicity. For these reasons, the analysis of such compounds by LC typically requires derivatization [ 1 , 3 , 4 , 25 , 26 , 27 ] or other chemical reactions (e.g., oxidation) aimed at converting the analytes into detectable molecules [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

A Novel Chromatographic Method to Assess the Binding Ability towards Dicarbonyls

et al. 2023

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Human exposure to dicarbonyls occurs via ingestion (e.g., food), inhalation (e.g., electronic cigarettes) and dysregulation of endogenous metabolic pathways (e.g., glycolysis). Dicarbonyls are electrophiles able to induce carbonylation of endogenous substrate. They have been associated with the onset and progression of several human diseases. Several studies have advocated the use of dicarbonyl binders as food preservatives or as drugs aimed at mitigating carbonylation. This study presents the setup of an easy and cheap assay for the screening of selective and potent dicarbonyl binders. The method is based on the incubation of the candidate molecules with a molecular probe. The activity is then determined by measuring the residual concentration of the molecular probe over time by liquid chromatography (LC). However, the naturally occurring dicarbonyls (e.g., glyoxal, methylglyoxal) are not appealing as probes since they are hard to separate and detect using the most popular LC variants. Benzylglyoxal (BGO) was therefore synthesized and tested, proving to be a convenient probe that allows a direct quantification of residual dicarbonyls by reversed phase LC without derivatization. The method was qualified by assessing the binding ability of some molecules known as binders of natural occurring dicarbonyls, obtaining results consistent with literature.

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A fast and efficient method for the analysis of α-dicarbonyl compounds in aqueous solutions: Development and application

Cited by 11 publications

References 51 publications

Gas-Phase Photolysis and Photo-Oxidation of Isoprene-Derived Atmospherically Relevant Hydroxy Nitrates

Gas-Phase Photolysis and Photo-Oxidation of Isoprene-Derived Atmospherically Relevant Hydroxy Nitrates

Simultaneous determination of six α‑dicarbonyl compounds in traditional Chinese medicines using high‐performance liquid chromatography‐fluorescence detector with pre‐column derivatization

A Novel Chromatographic Method to Assess the Binding Ability towards Dicarbonyls

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