Mass Spectrometric Characterization of Epoxidized Vegetable Oils

Kuki, Ákos; Nagy, Tibor; Hashimov, Mahir; File, Stella; Nagy, Miklós; Zsuga, Miklós; Kéki, Sándor

doi:10.3390/polym11030394

Cited by 9 publications

(6 citation statements)

References 17 publications

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“…ESI of the synthesized materials generated MS signals corresponding to [M + NH 4 ] + and minor [M + Na] + ions. Although prior reports demonstrated simplified MS/MS spectra for [M + Na] + ESO ions, 12 this ion type was not studied further due to low precursor ion intensity and fragment ion yield.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, these techniques cannot directly detect the intact ESO byproduct species and other components of the formulation, limiting the approach’s utility for nontargeted analysis and suspect screening . Although other studies utilize direct infusion with electrospray ionization (ESI) or matrix assisted laser desorption/ionization (MALDI) to observe intact ESO species, their application is limited to detection of ESO only. − …”

Section: Introductionmentioning

confidence: 99%

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Monitoring Epoxidized Soybean Oil Degradation Using Liquid Chromatography–Mass Spectrometry and In Silico Spectral Libraries

Hutchins,

Saez Cabezas,

Enokida

et al. 2024

J. Am. Soc. Mass Spectrom.

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Epoxidized soybean oil (ESO) is routinely used as a bioderived plasticizer and stabilizer in polyvinyl chloride (PVC), as it prolongs material integrity during dehydrochlorination. During this process, the epoxide moieties of ESO are progressively converted to chlorohydrins, which amplify ESO's inherent structural complexity. Past characterization efforts utilized separation−mass spectrometry (MS) analysis of the hydrolyzed acyl chains to simplify the complexity. However, this approach significantly increases the complexity of sample preparation and cannot directly monitor the chlorination of individual ESO species during aging. Here, we present a comprehensive LC−MS/MS data acquisition and in silico spectral library identification workflow optimized for intact ESO byproduct analysis. Detailed MS/MS fragmentation rules derived from synthesized standards were coupled with improved fragment ion intensity modeling capabilities to generate a high-fidelity spectral library for rapid ESO byproduct identification. Identification confidence was further bolstered by using retention time modeling to filter spurious MS/MS matches. Finally, we paired this informatic approach with an optimized extraction procedure and reversed-phase separation to generate a detailed timeline of more than 400 ESO species and byproducts during PVC thermal aging. These developments significantly improve our ability to detect, characterize, and understand ESO degradation in complex PVC formulations with new levels of molecular resolution.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Monitoring Epoxidized Soybean Oil Degradation Using Liquid Chromatography–Mass Spectrometry and In Silico Spectral Libraries

Hutchins,

Saez Cabezas,

Enokida

et al. 2024

J. Am. Soc. Mass Spectrom.

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“…Recently, we developed the Mass-remainder analysis (MARA), which is capable of handling the mass spectra of copolymers, even those obtained by low-resolution mass spectrometer. The capability of our method was proved by analyzing copolymers [15], epoxidized vegetable oils [16], crude oil [17], copolymer blends [18] and even for the analysis of flavonoids [19]. The further development of such a filtering method is of paramount importance for the processing of complex mass spectra.…”

Section: Introductionmentioning

confidence: 94%

A Short-Cut Data Mining Method for the Mass Spectrometric Characterization of Block Copolymers

et al. 2021

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A new data mining approach as a short cut method is given for the determination of the copolymer composition from mass spectra. Our method simplifies the copolymer mass spectra by reduction of the number of mass peaks. The proposed procedure, namely the selection of the mass peaks, which is based on the most abundant peak of the mass spectrum, can be performed manually or more efficiently using our recently invented Mass-remainder analysis (MARA). The considerable reduction of the MS spectra also simplifies the calculation of the copolymer quantities for instance the number- and weight-average molecular weights (Mn and Mw, respectively), polydispersity index (Đ = Mw/Mn), average molar fraction (cA) and weight fraction (wA) of the comonomer A and so on. These copolymer properties are in line with those calculated by a reference method taking into account all the mass peaks of the copolymer distribution. We also suggest a highly efficient method and template for the determination of the composition drift by processing the reduced mass spectra.

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“…Recently, we have developed a data mining algorithm, called mass-remainder analysis (MARA) and its improved variant, multi-step mass-remainder analysis (M-MARA) for the processing and assessment of complex mass spectra [ 23 , 24 , 25 , 26 , 27 ]. In this paper, we propose a novel method for the comprehensive filtering and screening of flavonoids in the DIMS spectra of natural extracts.…”

Section: Introductionmentioning

confidence: 99%

Mass Spectral Filtering by Mass-Remainder Analysis (MARA) at High Resolution and Its Application to Metabolite Profiling of Flavonoids

Nagy

Roth

Kuki

et al. 2021

IJMS

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Flavonoids represent an important class of secondary metabolites because of their potential health benefits and functions in plants. We propose a novel method for the comprehensive flavonoid filtering and screening based on direct infusion mass spectrometry (DIMS) analysis. The recently invented data mining procedure, the multi-step mass-remainder analysis (M-MARA) technique is applied for the effective mass spectral filtering of the peak rich spectra of natural herb extracts. In addition, our flavonoid-filtering algorithm facilitates the determination of the elemental composition. M-MARA flavonoid-filtering uses simple mathematical and logical operations and thus, it can easily be implemented in a regular spreadsheet software. A huge benefit of our method is the high speed and the low demand for computing power and memory that enables the real time application even for tandem mass spectrometric analysis. Our novel method was applied for the electrospray ionization (ESI) DIMS spectra of various herb extract, and the filtered mass spectral data were subjected to chemometrics analysis using principal component analysis (PCA).

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Mass Spectrometric Characterization of Epoxidized Vegetable Oils

Cited by 9 publications

References 17 publications

Monitoring Epoxidized Soybean Oil Degradation Using Liquid Chromatography–Mass Spectrometry and In Silico Spectral Libraries

Monitoring Epoxidized Soybean Oil Degradation Using Liquid Chromatography–Mass Spectrometry and In Silico Spectral Libraries

A Short-Cut Data Mining Method for the Mass Spectrometric Characterization of Block Copolymers

Mass Spectral Filtering by Mass-Remainder Analysis (MARA) at High Resolution and Its Application to Metabolite Profiling of Flavonoids

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