Isolation and Analysis of Essential Oils from Spices

O’Shea, Stephen K.; Riesen, Daniel D. Von; Rossi, Lauren L.

doi:10.1021/ed101141w

Cited by 24 publications

(20 citation statements)

References 46 publications

(56 reference statements)

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“…They could be converted to the corresponding ketones in this catalytic system, and the overall yields of the ketones were 64.8% ( Table 2 , entry 5), 74.2% ( Table 2 , entry 6) and 60.2% ( Table 2 , entry 7), respectively. Anethole and trans -anethole exist widely in anise, fennel and tarragon, which can be extracted 21 22 23 . Anethole ( Table 2 , entry 8) and trans -anethole ( Table 2 , entry 9) could be converted into to 4-propylcyclohexanone with yields of 77.3% and 71.8%, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of ketones from biomass-derived feedstock

et al. 2017

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Cyclohexanone and its derivatives are very important chemicals, which are currently produced mainly by oxidation of cyclohexane or alkylcyclohexane, hydrogenation of phenols, and alkylation of cyclohexanone. Here we report that bromide salt-modified Pd/C in H2O/CH2Cl2 can efficiently catalyse the transformation of aromatic ethers, which can be derived from biomass, to cyclohexanone and its derivatives via hydrogenation and hydrolysis processes. The yield of cyclohexanone from anisole can reach 96%, and the yields of cyclohexanone derivatives produced from the aromatic ethers, which can be extracted from plants or derived from lignin, are also satisfactory. Detailed study shows that the Pd, bromide salt and H2O/CH2Cl2 work cooperatively to promote the desired reaction and inhibit the side reaction. Thus high yields of desired products can be obtained. This work opens the way for production of ketones from aromatic ethers that can be derived from biomass.

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Section: Resultsmentioning

confidence: 99%

“…It can be expected that more feasible methods will be developed to produce various aromatic ethers from lignin. Moreover, aromatic ethers, such as anethole, trans -anethole, exist widely in plants and can be directly extracted 21 22 23 . The representative aromatic ethers depicted in Fig.…”

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confidence: 99%

Synthesis of ketones from biomass-derived feedstock

et al. 2017

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“…Gas chromatography (GC), coupled with mass spectrometry detection, is a powerful technique used for volatile components analysis, as it provides qualitative and quantitative data for complex mixtures such as those usually present in EOs …”

Section: Introductionmentioning

confidence: 99%

Comparative study of GC‐MS characterization, antioxidant activity and hyaluronidase inhibition of different species of Lavandula and Thymus essential oils

Carrasco

Pérez-Ruíz

Tudela

et al. 2015

Flavour & Fragrance J

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The chemical compositions of essential oils of Lavandula angustifolia, Lavandula latifolia, Lavandula hybrida cultivar Grosso and cultivar Super, Thymus zygis with high proportions of thymol and linalool and Thymus hyemalis, from Murcia country (Spain), were studied in relative (%), absolute (mM) and chiral concentrations by GC/MS. Hyaluronidase inhibition and antioxidant activities of the essential oils were evaluated using ABTS•+, DPPH•, ORAC, chelating power, hydroxyl radical, nitric oxide, TBARS and reducing power assays. Linalool and linalyl acetate were the most abundant components in the Lavandula genus whereas thymol, linalool and 1,8‐cineole were the most abundant molecules in the respective Thymus species. Chiral determination of the main components showed (+)‐enantiomers like terpinen‐4‐ol, β‐pinene, borneol and α‐terpineol and (−)‐enantiomers like linalool, linalyl acetate and camphene in Lavandula sp. In the case of Thymus sp. (+)‐enantiomers like α‐pinene, limonene, terpinen‐4‐ol and α‐terpineol and (−)‐enantiomers like borneol were found. Essential oils containing thymol were found especially powerful in all assays but chelating power, ORAC and hydroxyl radical scavenging assays. The capacity for inhibiting hyaluronidase showed that T. zygis with a high proportion of thymol was the most effective inhibitor. Essential oils containing thymol and linalool/linalyl acetate have a potential use as antioxidant agents. Thymol shows strong inhibition of hyaluronidase. Copyright © 2015 John Wiley & Sons, Ltd.

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“…O'Shea and co-workers published an exercise wherein various essential oils are isolated from spices, and high performance liquid chromatography (HPLC) and gas chromatography−mass spectrometry (GC−MS) are then used to deduce the spice associated with each oil. 8 Finally, LeFevre and co-workers described a laboratory experiment in which friedelin (3, Figure 1) is isolated from cork and reduced to the corresponding alcohol. 9 To determine which diastereomer is formed in this reaction, force field minimizations are used to determine optimal dihedral angles for each diastereomer, followed by application of the Karplus equation 10 to calculate the corresponding coupling constants expected for each diastereomer.…”

Section: Previous Laboratory Exercises Involving Natural Product Isolmentioning

confidence: 99%

Reassigning the Structures of Natural Products Using NMR Chemical Shifts Computed with Quantum Mechanics: A Laboratory Exercise

et al. 2014

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An applied computational chemistry laboratory exercise is described in which students use modern quantum chemical calculations of chemical shifts to assign the structure of a recently isolated natural product. A pre/post assessment was used to measure student learning gains and verify that students demonstrated proficiency of key learning objectives. ■ INTRODUCTIONThe elucidation of the structures (connectivity, relative stereochemistry, and configuration) of complex natural products is a challenging endeavor despite huge leaps in spectroscopic technology over the past century. Among the most useful tools for structure elucidation is nuclear magnetic resonance (NMR) spectroscopy. Recently, Breton and Reynolds presented an excellent review of the various tools natural products chemists utilize in assigning structures, with an emphasis on how the use of NMR spectroscopy has evolved over the years. 1 Previous work has demonstrated the utility of NMR computations, in conjunction with traditional analyses, in the assignment and reassignment of natural product structures. 2 Upper-division undergraduate chemistry courses generally do not expose students to this important aspect of NMR spectroscopy. Herein, a computer-based laboratory experiment is described that highlights this application of NMR spectroscopy, as well as the utility of quantum chemical calculations, through a brief project that models a state-of-the-art research project in the field of structural elucidation. This exercise is appropriate for students who have been introduced to the basic concepts of NMR spectroscopy and quantum mechanics; advanced knowledge of neither is required. Consequently, this lab exercise could be adapted for an undergraduate or graduate organic, natural products, quantum chemistry, or applied theoretical chemistry course (and perhaps others).Key features of the approach include the following: 1. The exercise described is derived from recent reports on current research problems in the natural products and applied theoretical chemistry fields. 2. The exercise is designed to encourage hypothesis generation and testing, experimental design, discovery, active learning, 3 and data analysis by utilizing many activities and questions that involve higher order cognitive processes. 4 3. The exercise provides a basic framework for applying NMR calculations to structure elucidation that is suitable for a 1−2 h laboratory period, but possible extensions appropriate for different courses, cohorts of students, and instructors are provided in the Supporting Information.

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Isolation and Analysis of Essential Oils from Spices

Cited by 24 publications

References 46 publications

Synthesis of ketones from biomass-derived feedstock

Synthesis of ketones from biomass-derived feedstock

Comparative study of GC‐MS characterization, antioxidant activity and hyaluronidase inhibition of different species of Lavandula and Thymus essential oils

Reassigning the Structures of Natural Products Using NMR Chemical Shifts Computed with Quantum Mechanics: A Laboratory Exercise

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