Identification of α-Tocopherol and Its Oxidation Products by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry

Tang, Chuanhui; Tao, Guanjun; Wang, Yue; Liu, Yuanfa; Li, Jinwei

doi:10.1021/acs.jafc.9b06544

Cited by 16 publications

(12 citation statements)

References 37 publications

(85 reference statements)

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“…THC has a stronger tendency to degrade compared to VEA. − Regarding ketene that has been suggested to be formed by vaping or pyrolytic heating of VEA, it is not clear whether it is identifiable with our methods or is not formed at the temperatures tested here. Products like duroquinone and durohydroquinone ,− are reported to be formed below a vaping coil temperature of 300 °C; however, we do not observe them with the preparation or detection methods used in this work. The selectivity and solubility of GC-MS extraction solvent could be a reason why products like quinones were not observed in the current study.…”

Section: Discussioncontrasting

confidence: 65%

Vaping Aerosols from Vitamin E Acetate and Tetrahydrocannabinol Oil: Chemistry and Composition

Dai

Tran

et al. 2022

Chem. Res. Toxicol.

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The popularity of vaping cannabis products has increased sharply in recent years. In 2019, a sudden onset of electronic cigarette/vaping-associated lung injury (EVALI) was reported, leading to thousands of cases of lung illness and dozens of deaths due to the vaping of tetrahydrocannabinol (THC)-containing e-liquids that were obtained on the black market. A potential cause of EVALI has been hypothesized due to the illicit use of vitamin E acetate (VEA) in cannabis vape cartridges. However, the chemistry that modifies VEA and THC oil, to potentially produce toxic byproducts, is not well understood under different scenarios of use. In this work, we quantified carbonyls, organic acids, cannabinoids, and terpenes in the vaping aerosol of pure VEA, purified THC oil, and an equal volume mixture of VEA and THC oil at various coil temperatures (100−300 °C). It was found under the conditions of our study that degradation of VEA and cannabinoids, including Δ 9 -THC and cannabigerol (CBG), occurred via radical oxidation and direct thermal decomposition pathways. Evidence of terpene degradation was also observed. The bond cleavage of aliphatic side chains in both VEA and cannabinoids formed a variety of smaller carbonyls. Oxidation at the ring positions of cannabinoids formed various functionalized products. We show that THC oil has a stronger tendency to aerosolize and degrade compared to VEA at a given temperature. The addition of VEA to the e-liquid nonlinearly suppressed the formation of vape aerosol compared to THC oil. At the same time, toxic carbonyls including formaldehyde, 4-methylpentanal, glyoxal, or diacetyl and its isomers were highly enhanced in VEA e-liquid when normalized to particle mass.

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Section: Discussioncontrasting

confidence: 65%

Vaping Aerosols from Vitamin E Acetate and Tetrahydrocannabinol Oil: Chemistry and Composition

Dai

Tran

et al. 2022

Chem. Res. Toxicol.

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“…Mass spectrometry is deemed to be the most precise method for the qualitative analysis and identification of unknown compounds. Hence, it has been successfully used with LC and GC to identify vitamin E isomers (Bartosińska et al., 2016; Lu et al., 2019; C. Tang et al., 2019).…”

Section: Methods For Vitamin E Analysismentioning

confidence: 99%

Vitamin E in foodstuff: Nutritional, analytical, and food technology aspects

Zaaboul

Liu

2022

Comp Rev Food Sci Food Safe

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Vitamin E is a group of isoprenoid chromanols with different biological activities. It comprises eight oil‐soluble compounds: four tocopherols, namely, α‐, β‐, γ‐, and δ‐tocopherols; and four tocotrienols, namely, α‐, β‐, γ, and δ‐tocotrienols. Vitamin E isomers are well‐known for their antioxidant activity, gene‐regulation effects, and anti‐inflammatory and nephroprotective properties. Considering that vitamin E is exclusively synthesized by photosynthetic organisms, animals can only acquire it through their diet. Plant‐based food is the primary source of vitamin E; hence, oils, nuts, fruits, and vegetables with high contents of vitamin E are mostly consumed after processing, including industrial processes and home‐cooking, which involve vitamin E profile and content alteration during their preparation. Accordingly, it is essential to identify the vitamin E content and profile in foodstuff to match daily intake requirements. This review summarizes recent advances in vitamin E chemistry, metabolism and metabolites, current knowledge on their contents and profiles in raw and processed plant foods, and finally, their modern developments in analytical methods.

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“…It led us to discover the other oxidative product ions of α-T, including those with m/z values of 445.368, 463.378, and 447.383, as described in Figure 1 and the literature. 19)…”

Section: Determination Of Split Timingmentioning

confidence: 99%

“…α-Tocopherol (α-T), in particular, is well known to prevent lipid peroxidation. [15][16][17] The α-T oxidation reaction scheme reported by Kumar et al 18) and Tang et al 19) is summarized in Figure 1 Although the details of the self-defense system of plant cells against 1 O2 using α-T are recently being determined by combining several analytical methods, the analytical process involves complex procedures and requires more than 30 min of chromatographic run time. Accordingly, a more rapid and sensitive method for investigating the defense system in individual cells is required.…”

Section: Introductionmentioning

confidence: 99%

Rapid Analysis of α-Tocopherol and Its Oxidation Products Using Supercritical Carbon Dioxide and Proton Transfer Reaction Ionization Mass Spectrometry

et al. 2022

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We have developed a rapid and sensitive analytical method for α-tocopherol and its oxidative products by combining online hyphenation of supercritical fluid extraction-supercritical fluid chromatography (SFC) with proton transfer reaction (PTR) ionization mass spectrometry (MS). α-Tocopherol is a well-known antioxidant that plays a vital role in the antioxidant defense system in plant cells. However, studies on the cellular mechanisms of α-tocopherol have been limited owing to the lack of a rapid analytical method, which limits the comparison of plant cells incubated in various conditions. Additionally, complex sample preparation and long chromatography separation times are required. Moreover, the majority of the involved molecules are a combination of isomers, which must be separated before applying tandem MS. α-Tocopherol produces the α-tocopheroxyl radical in the first step of its antioxidant function; another ion with the same mass may also be generated from the source. SFC separation effectively distinguished the observed ions from their oxidative products in the sample and those produced during the ionization reaction process. This method enabled the measurement of α-tocopherol and its oxidative products such as α-tocopheroxyl radical and αtocopheryl quinone in approximately 3 min per sample, including the time required for sample preparation.

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Identification of α-Tocopherol and Its Oxidation Products by Ultra-Performance Liquid Chromatography Coupled with Quadrupole Time-of-Flight Mass Spectrometry

Cited by 16 publications

References 37 publications

Vaping Aerosols from Vitamin E Acetate and Tetrahydrocannabinol Oil: Chemistry and Composition

Vaping Aerosols from Vitamin E Acetate and Tetrahydrocannabinol Oil: Chemistry and Composition

Vitamin E in foodstuff: Nutritional, analytical, and food technology aspects

Rapid Analysis of α-Tocopherol and Its Oxidation Products Using Supercritical Carbon Dioxide and Proton Transfer Reaction Ionization Mass Spectrometry

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