Identification and quantification of 1,3-dimethylbutylamine (DMBA) from Camellia sinensis tea leaves and dietary supplements

Avula, Bharathi; Wang, Mei; Sagi, S; Cohen, Pieter A.; Wang, Yanhong; Lasonkar, Pradeep B.; Chittiboyina, Amar G.; Wei, Feng; Khan, Ikhlas A.

doi:10.1016/j.jpba.2015.07.004

Cited by 13 publications

(7 citation statements)

References 17 publications

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“…For 1,3-DMBA (a small aliphatic amine), although its high abundance in TWPs correlates well with its high environmental occurrence, we still note that there are potential sources of 1,3-DMBA other than as a 6PPD TP . For example, it is reported as a potent stimulant used in dietary supplements. , TP 274/6PPDQ and TP 282b/6PPDQ peak area ratios were increased to 68 and 40 in roadway runoff versus 19 and 3 in TWP leachate, respectively (Figure d). The abundance and stability of TP 274 in TWP leachate and roadway runoff similarly indicate its high potential for environmental discharge; we now consider TP 274 to be a major environmentally relevant TP of 6PPD.…”

Section: Resultsmentioning

confidence: 93%

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Zhao

Tian

et al. 2023

Environ. Sci. Technol.

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6PPD, a tire rubber antioxidant, poses substantial ecological risks because it can form a highly toxic quinone transformation product (TP), 6PPD-quinone (6PPDQ), during exposure to gas-phase ozone. Important data gaps exist regarding the structures, reaction mechanisms, and environmental occurrence of TPs from 6PPD ozonation. To address these data gaps, gas-phase ozonation of 6PPD was conducted over 24–168 h and ozonation TPs were characterized using high-resolution mass spectrometry. The probable structures were proposed for 23 TPs with 5 subsequently standard-verified. Consistent with prior findings, 6PPDQ (C18H22N2O2) was one of the major TPs in 6PPD ozonation (∼1 to 19% yield). Notably, 6PPDQ was not observed during ozonation of 6QDI (N-(1,3-dimethylbutyl)-N′-phenyl-p-quinonediimine), indicating that 6PPDQ formation does not proceed through 6QDI or associated 6QDI TPs. Other major 6PPD TPs included multiple C18H22N2O and C18H22N2O2 isomers, with presumptive N-oxide, N,N′-dioxide, and orthoquinone structures. Standard-verified TPs were quantified in roadway-impacted environmental samples, with total concentrations of 130 ± 3.2 μg/g in methanol extracts of tire tread wear particles (TWPs), 34 ± 4 μg/g-TWP in aqueous TWP leachates, 2700 ± 1500 ng/L in roadway runoff, and 1900 ± 1200 ng/L in roadway-impacted creeks. These data demonstrate that 6PPD TPs are likely an important and ubiquitous class of contaminants in roadway-impacted environments.

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Section: Resultsmentioning

confidence: 93%

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Zhao

Tian

et al. 2023

Environ. Sci. Technol.

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“…1,3-DMBA was the highest TP detected (Figure c). Notably, although 1,3-DMBA was included in this study as a 6PPD TP, it is a powerful, unauthorized stimulant sometimes used in dietary supplements that became more widely used after another similar amine (dimethyl amylamine) was phased out due to severe health risks (strokes, heart failure, sudden death). , The CompTox Chemicals Dashboard also reports possible androgenic activity for 1,3-DMBA . 4s DPA, a TP of 6PPD with a nitroso group and therefore potentially carcinogenic, − was detected in the doormat and crumb rubber samples.…”

Section: Resultsmentioning

confidence: 99%

Screening p-Phenylenediamine Antioxidants, Their Transformation Products, and Industrial Chemical Additives in Crumb Rubber and Elastomeric Consumer Products

Zhao

Gonzalez

et al. 2023

Environ. Sci. Technol.

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Recently, roadway releases of N,N′-substituted p-phenylenediamine (PPD) antioxidants and their transformation products (TPs) received significant attention due to the highly toxic 6PPD-quinone. However, the occurrence of PPDs and TPs in recycled tire rubber products remains uncharacterized. Here, we analyzed tire wear particles (TWPs), recycled rubber doormats, and turf-field crumb rubbers for seven PPD antioxidants, five PPD-quinones (PPDQs), and five other 6PPD TPs using liquid chromatography-tandem mass spectrometry. PPD antioxidants, PPDQs, and other TPs were present in all samples with chemical profiles dominated by 6PPD, DTPD, DPPD, and their corresponding PPDQs. Interestingly, the individual [PPDQ]/[PPD] and [TP]/[PPD] ratios significantly increased as total concentrations of the PPD-derived chemical decreased, indicating that TPs (including PPDQs) dominated the PPD-derived compounds with increased environmental weathering. Furthermore, we quantified 15 other industrial rubber additives (including bonding agents, vulcanization accelerators, benzotriazole and benzothiazole derivatives, and diphenylamine antioxidants), observing that PPD-derived chemical concentrations were 0.5−6 times higher than these often-studied additives. We also screened various other elastomeric consumer products, consistently detecting PPD-derived compounds in lab stoppers, sneaker soles, and rubber garden hose samples. These data emphasize that PPD antioxidants, PPDQs, and related TPs are important, previously overlooked contaminant classes in tire rubbers and elastomeric consumer products.

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“…As an enhanced form of TLC, high‐performance thin‐layer chromatography (HPTLC) is an analytical technique based on TLC, but with enhancements intended to increase the resolution of the compounds to be separated and to allow quantitative analysis of the compounds (Attimarad, Mueen Ahmed, Aldhubaib, & Harsha, 2011). Existing literatures demonstrate the feasibility and efficiency of HPTLC in the quantification of chemical parameters, such as caffeine and theanine (Khan et al., 2011; Kumar, Gulati, & Sharma, 2016; Kunugi & Tabei, 1997), and organic contaminants, such as pesticides (Yue, Zhang, Fan, & Tang, 2008) and 1,3‐dimethylbutylamine (DMBA) (Avula et al., 2015). Applying HPTLC in the identification of green tea with different batches is also reported (Reich et al., 2006).…”

Section: Emerging Techniquesmentioning

confidence: 99%

Emerging techniques for determining the quality and safety of tea products: A review

Sun

2020

Comp Rev Food Sci Food Safe

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Spectroscopic techniques, electrochemical methods, nanozymes, computer vision, and modified chromatographic techniques are the emerging techniques for determining the quality and safety parameters (e.g., physical, chemical, microbiological, and classified parameters, as well as inorganic and organic contaminants) of tea products (such as fresh tea leaves, commercial tea, tea beverage, tea powder, and tea bakery products) effectively. By simplifying the sample preparation, speeding up the detection process, reducing the interference of other substances contained in the sample, and improving the sensitivity and accuracy of the current standard techniques, the abovementioned emerging techniques achieve rapid, cost‐effective, and nondestructive or slightly destructive determination of tea products, with some of them providing real‐time detection results. Applying these emerging techniques in the whole industry of tea product processing, right from the picking of fresh tea leaves, fermentation of tea leaves, to the sensory evaluation of commercial tea, as well as developing portable devices for real‐time and on‐site determination of classified and safety parameters (e.g., the geographical origin, grade, and content of contaminants) will not only eliminate the strong dependence on professionals but also help mechanize the production of tea products, which deserves further research. Conducting a review on the application of spectroscopic techniques, electrochemical methods, nanozymes, computer vision, and modifications of chromatographic techniques for quality and safety determination of tea products may serve as guide for other types of foods and beverages, offering potential techniques for their detection and evaluation, which would promote the development of the food industry.

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Identification and quantification of 1,3-dimethylbutylamine (DMBA) from Camellia sinensis tea leaves and dietary supplements

Cited by 13 publications

References 17 publications

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Screening p-Phenylenediamine Antioxidants, Their Transformation Products, and Industrial Chemical Additives in Crumb Rubber and Elastomeric Consumer Products

Emerging techniques for determining the quality and safety of tea products: A review

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