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A robust and efficient enantioselective separation of racemic menthol was achieved on a standard C column with reverse-phase high-performance liquid chromatography (RP-HPLC) and UV detector. (R)-α-hydroxy-4-methylbenzeneacetic acid was utilized as the pre-column derivatization reagent. The impact of mobile phase composition on diastereomer selectivity was thoroughly investigated, resulting in a high resolution of 2.11 under optimized conditions. The method was rigorously validated for linearity, precision, accuracy, limit of detection (LOD) and limit of quantification (LOQ). Notably, a separation pre-screening mechanism (SPM) and a prediction model was developed based on density functional theory (DFT) studies. This model elucidated the relationship between molecular polarity differences (△MPI) and chromatographic behavior, facilitating the interpretation and prediction of racemic menthol resolution with various chiral derivatization reagents. The present work not only presents an efficient and economical approach for menthol enantiomeric separation, but also offers valuable insights for the innovative design and advancement of chromatographic methodologies for a wide array of chiral enantiomers.
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http://dx.doi.org/10.1016/j.talanta.2024.127062 | DOI Listing |
Nicotine Tob Res
May 2025
Department of Health Behavior, Roswell Park Comprehensive Cancer Center, Buffalo, NY, USA.
Introduction: Flavored oral tobacco-free pouches (ONPs) are novel products that resemble traditional oral tobacco-containing pouches (OTPs) in design and route of administration. However, ONPs contain nicotine, various additives, and a filler material rather than tobacco leaves. Our study compares nicotine content, release, and form, along with selected flavorings content, between brands of ONPs and OTPs.
View Article and Find Full Text PDFAnal Bioanal Chem
March 2025
Department of Chemistry, Sapienza University, P.Le Aldo Moro 5, 00185, Rome, Italy.
The increasing use of chiral agrochemicals sold as racemic formulations raises concern for the negative impacts that inactive enantiomers can have on aquatic life and human health. The present work just focuses on the determination of ten chiral pesticides in river water samples by applying a ferrofluid-based microextraction followed by their stereoselective liquid chromatography analysis. To develop the ferrofluid, magnetite nanoparticles were prepared and coated with oleic acid and then dispersed in a hydrophobic natural deep eutectic solvent (NaDES), composed of L-menthol and thymol (1:1).
View Article and Find Full Text PDFTalanta
January 2025
Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, China; Shanghai Research Institute of Fragrance & Flavor Industry, 480 Nanning Road, Shanghai, 200232, China. Electronic address:
Int J Biol Macromol
March 2024
The Key Laboratory of Industrial Biotechnology, Ministry of Education, Laboratory of Applied Microorganisms and Metabolic Engineering, School of Biotechnology, Jiangnan University, Wuxi 214122, China.. Electronic address:
(R)-Citronellal is a valuable molecule as the precursor for the industrial synthesis of (-)-menthol, one of the worldwide best-selling compounds in the flavors and fragrances field. However, its biocatalytic production, even from the optically pure substrate (E)-citral, is inherently limited by the activity of Old Yellow Enzyme (OYE). Herein, we rationally designed a different approach to increase the activity of OYE in biocatalytic production.
View Article and Find Full Text PDFPhys Chem Chem Phys
July 2023
Department of Cell and Molecular Biology, Faculty of Life Science and Biotechnology, Shahid Beheshti University, P.O. Box 1983969411, Tehran, Iran.
The structural and physicochemical properties of chiral deep eutectic solvents (DESs) consisting of racemic mixtures of menthol and acetic acid (DES1), racemic mixtures of menthol and lauric acid (DES2), and racemic mixtures of menthol and pyruvic acid (DES3) for enantioselective extraction processes are investigated. Structural results, such as the radial distribution function (RDF) and the combined distribution function (CDF), indicate that the hydroxyl hydrogen of menthol has a dominant interaction with the carbonyl oxygen of the acids in the considered DESs. The number of hydrogen bonds and non-bonded interaction energies formed between -menthol and HBDs are larger than those with -menthol, resulting in the self-diffusion coefficient of -menthol being larger than that of -menthol.
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