Dataset Information

Data on the identification and characterization of by-products from N-Cbz-3-aminopropanal and t-BuOOH/H2O2 chemical reaction in chloroperoxidase-catalyzed oxidations.

ABSTRACT: This data article is related to the subject of a publication in Process Biochemistry, entitled "Chloroperoxidase-catalyzed amino alcohol oxidation: Substrate specificity and novel strategy for the synthesis of N-Cbz-3-aminopropanal" (Masdeu et al., 2016) [1]. Here, the products of the chemical reaction involving the amino aldehyde (N-Cbz-3-aminopropanal) and peroxides (tert-butyl hydroperoxide and H2O2) are characterized by NMR. (1)H and (13)C NMR full characterization of the products was obtained based on 2D NMR, 1D selective NOESY and diffusion spectroscopy (DOSY) experiments.

SUBMITTER: Masdeu G

PROVIDER: S-EPMC4939320 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Data on the identification and characterization of by-products from N-Cbz-3-aminopropanal and t-BuOOH/H2O2 chemical reaction in chloroperoxidase-catalyzed oxidations.

Masdeu Gerard G Pérez-Trujillo Míriam M López-Santín Josep J Álvaro Gregorio G

Data in brief 20160623

This data article is related to the subject of a publication in Process Biochemistry, entitled "Chloroperoxidase-catalyzed amino alcohol oxidation: Substrate specificity and novel strategy for the synthesis of N-Cbz-3-aminopropanal" (Masdeu et al., 2016) [1]. Here, the products of the chemical reaction involving the amino aldehyde (N-Cbz-3-aminopropanal) and peroxides (tert-butyl hydroperoxide and H2O2) are characterized by NMR. (1)H and (13)C NMR full characterization of the products was obtain ...[more]

PMID: 27437440

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Project description:Recently, cannabidiol (CBD), one of the major components of the Cannabis species, has been a focus in the cannabis industry due to its various pharmacological effects. Interestingly, CBD can be converted into several psychoactive cannabinoids, such as 9-tetrahydrocannabinol (Δ9-THC) and its structural isomers, under acidic reaction conditions. In this study, chemical transformation of CBD in ethanol solution was conducted with variation in pH at 2.0, 3.5, and 5.0 by addition of 0.1 M hydrochloric acid (HCl). These resulting solutions were derivatized with trimethylsilyl (TMS) reagent and analyzed using GC/MS-scan mode. Time profiles of CBD degradation and transformation of products were examined according to variations in pH and temperature. Several transformed products produced after the acidic reaction of CBD were identified by matching retention times and mass spectra to authentic standards. Regarding the identification of products without authentic standards, the EI-mass spectra of such cannabinoid-OTMS derivatives were interpreted according to structural class, suggesting mass fragmentation pathways. From the GC/MS data, Δ9-THC, CBC, and ethoxy-hexahydrocannabinol (HHC) analogs were shown to be major components, and THC isomers (Δ8- and Δ10-THCs) and 9-hydroxy-HHC were observed as minor components. Using time profile data, the acidity of the reaction solution was an important factor in degradation of CBD. Degradation of CBD and formation of THC rarely occurred at pH 5.0, even at 70 °C with a long process time of 24 h. In contrast, degradation of CBD occurred readily at pH 3.5 and 30 °C over a short process time and was further accelerated by lowering pH, increasing temperature, and lengthening the process time. Based on profile data and identified transformed products, formation pathways from the degradation of CBD under acidic reaction conditions are suggested. Among the transformed products, seven components are known to have psychoactive effects. Thus, industrial CBD manufacturing processes in food and cosmetic products should be carefully controlled. These results will provide important guidelines on the control of manufacturing processes, storage, fermentation processes, and new regulation in industrial applications of CBD.

Dataset Information

Data on the identification and characterization of by-products from N-Cbz-3-aminopropanal and t-BuOOH/H2O2 chemical reaction in chloroperoxidase-catalyzed oxidations.

Publications

Data on the identification and characterization of by-products from N-Cbz-3-aminopropanal and t-BuOOH/H2O2 chemical reaction in chloroperoxidase-catalyzed oxidations.

Similar Datasets

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