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Carvone is an important flavoring substance and widely used in the food and chemical industries. Carvone has two optical isomers (L-carvone and D-carvone), which have different aroma characteristics. However, the green extraction of natural carvone and isolation of chiral carvone present challenges, leading to its limited application. In this study, a deep eutectic solvent (DES) was prepared and used as a green extraction solvent for the extraction of carvone from herbaceous plants, and then a chiral chromatography column combined with GC-MS was used for the separation and detection of L-carvone and D-carvone. Response surface methodology was used to optimize the extraction conditions including the volume of DES, extraction time and extraction temperature. The results showed that the extraction recoveries and intra-day precision ( = 6) were 83.5-101.3% and 3.2-6.1% when the volume of DES was 5 mL, and the extraction time and temperature were 25 min and 51 °C, respectively. The MLOD and MLOQ of L-carvone and D-carvone were 8.0 mg kg and 25.0 mg kg, respectively. The real sample detection results revealed that about 235.8-1600.0 mg kg of L-carvone was detected in L., and 6658.5-9788.6 mg kg of D-carvone in L. seeds. The established method can be an effective method for the detection of chiral carvone in herbaceous plants.
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http://dx.doi.org/10.1039/d4ay02002b | DOI Listing |
Dalton Trans
April 2025
A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 28 Vavilova str., Moscow, 119334, Russia.
Natural -carvone was converted into chiral 1-aryl-2-methyl-5-isopropyl-cyclohexadienes using a cross-coupling reaction as a key step. These dienes react with RuCl to give planar-chiral complexes [(arene)RuCl] in 70-75% yields. Complex [(1-Ph-2-Me-5-Pr-CH)RuCl], a chiral analogue of the classical catalyst [(cymene)RuCl], promotes C-H activation of -methoxy-benzamide and intramolecular insertion of a diazo compound into a C-H bond, but gives products with low stereoselectivity.
View Article and Find Full Text PDFAdv Sci (Weinh)
May 2025
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Science, 2 Bei Yi Jie, Zhong Guan Cun, Haidian District, Beijing, 100190, China.
Significant advances have been made in the preparation and application of luminescent hydrogen-bonded organic frameworks (HOFs) in recent years. These materials exhibit unique structural flexibility in accommodating guest molecules, rendering them promising candidates for dynamic applications. Herein, a 2D HOF material is presented, constructed by the binary assembly of 5,5'-bis(azanediyl)oxalyl diisophthalic acid and tetra(pyrid-4-ylphenyl)ethylene to achieve dynamic circularly polarized luminescence (CPL) with the aid of chiral guests.
View Article and Find Full Text PDFJ Coord Chem
January 2025
Department of Chemistry, University of the Free State, Bloemfontein, South Africa.
Bis-rhodium--chlorido dinuclear complexes with natural occurring limonene-type enantiomeric diene nucleophiles, (S)- and (R)-carvone [Car and Car], are presented and their single crystal structures reported. Utilizing the diolefinic bonds of the carvones, -[Rh(Car)Cl] () and -[Rh(Car)Cl] () were obtained in ca. 80% yields in clean reactions with reactant RhCl(HO).
View Article and Find Full Text PDFAnal Methods
February 2025
Guangzhou Quality Supervision and Testing Institute, Research Center of Risk Dynamic Detection and Early Warning for Food Safety of Guangzhou City, Key Laboratory of Detection Technology for Food Safety of Guangzhou City, Collaborative Innovation Center for NQI-Quality Safety of Guangzhou, Guangzhou
Carvone is an important flavoring substance and widely used in the food and chemical industries. Carvone has two optical isomers (L-carvone and D-carvone), which have different aroma characteristics. However, the green extraction of natural carvone and isolation of chiral carvone present challenges, leading to its limited application.
View Article and Find Full Text PDFPhys Chem Chem Phys
October 2024
Theoretical Chemistry Laboratory, Unit of Theoretical and Structural Physical Chemistry, Namur Institute of Structured Matter, University of Namur, B-5000 Namur, Belgium.
In this work, the HRS-OA circular differential scattering ratios of medium-size chiral molecules, -carvone and (1,5)-α-pinene, has been computed by means of TD-DFT calculations. The results have been discussed as a function of the basis set size. For -carvone a conformational analysis has been taken into account.
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