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The potential of Sn–B–NaY–ZE catalyst for transformation of citronellal-rich essential oils to menthol-enrich oil via optimization through single factorial design to enhance their organoleptic profile and biological activities

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Abstract

Citronellal-rich essential oils of Cymbopogon winterianus and Corymbia citriodora were catalytically modified in a two-step process to produce menthol and other terpene alcohols using Sn–B–NaY–ZE and 1%Pd/AC, successively. The reaction parameters such as solvent selection, reaction time, temperature, and catalyst loading were optimized using a single factorial design. In the first step, the citronellal was cyclized to isopulegol isomers with 99% selectivity at 80 °C for 90 min using 10% catalyst loading (Sn–B–NaY–ZE) in cyclohexane medium. Further, in the second step, this isopulegol was reduced to menthol using 1%Pd/AC. A part of menthol was isolated from the modified oils under low-temperature freezing (− 40 °C) process. Further modified menthol-rich essential oils and spent oil (after partial separation of menthol) were tested against the antibacterial and antioxidant activities. The results reveal that the modified spent oil of C. citriodora is effective against S. aureus and S. typhimurium bacterial strains. It was observed that the spent oil showed potent antimicrobial activities due to the enrichment of oxygenated monoterpenoids. Therefore, it suggested that the significant antimicrobial activity is due to the synergistic effects of menthol and other oxygenated monoterpenoids. Moreover, the spent oils have shown better antioxidant activities. The menthol in modified oil has changed the olfactometry to a sweet minty odor with cooling sensation. Hence, the modified essential oils are organoleptically superior due to their enhanced percentage of terpene alcohols and found potential application in various cosmeceutical preparations.

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The quality and reproducibility of the catalytic experiments were verified by triplicate analysis, and data reported on the average of these measurements. The spectroscopic measurements and bioactivity results are kept in their original files.

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Acknowledgements

The authors are grateful for research support from the Science and Engineering Research Board (SERB), DST, India (CRG/2021/002525). Director, CSIR-CIMAP, Lucknow, is respectfully acknowledged for providing the requisite facility as part of the CSIR-Aroma Mission, Phase-III (HCP 0007).

Funding

The Science and Engineering Research Board, DST, India funded the research with Grant Number CRG/2021/002525. The establishment of a laboratory facility as part of the CSIR-Aroma Mission, Phase III (HCP 0007, PE-III).

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Authors and Affiliations

  1. Phytochemistry Division, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, Uttar Pradesh, 226015, India

    Prashant Kumar, Anju Yadav, Chandan Singh Chanotiya, Debasmita Sahoo & Prasant Kumar Rout

  2. Bioprospection and Product Development Division, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow, Uttar Pradesh, 226015, India

    Laldingngheti Bawitlung & Anirban Pal

  3. Department of Chemistry, Krupajal Engineering College, Bhubaneswar, Odisha, 751002, India

    Priyabrat Mohapatra

  4. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    Prashant Kumar, Anju Yadav, Chandan Singh Chanotiya, Anirban Pal & Prasant Kumar Rout

  5. Centre for Advance Materials and Industrial Chemistry (CAMIC), School of Science, RMIT University, GPO Box 2476, Melbourne, 3001, Australia

    Prashant Kumar

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  1. Prashant Kumar
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Contributions

PK: validation, data curation and writing. AY: validation and data curation. CSC: investigation and visualization. DS: investigation and visualization. LB: validation and data curation. AP: validation, data curation. PM: investigation, visualization and supervision. PKR: investigation, methodology, visualization and supervision. All authors reviewed the manuscript

Corresponding authors

Correspondence to Priyabrat Mohapatra or Prasant Kumar Rout.

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There are no conflicting financial or non-financial interests that are directly or indirectly connected to the work submitted for publication.

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The work has been authorized for publication by the institute's internal publishing committee, with communication number CIMAP/PUB/2023/68.

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There are no results on living vertebrates or higher invertebrates, including humans, in the article. As a result, permission is granted for its publishing. Because all of the photographs are original and not taken from other sources, authorization is granted for the production of these images.

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Kumar, P., Yadav, A., Chanotiya, C.S. et al. The potential of Sn–B–NaY–ZE catalyst for transformation of citronellal-rich essential oils to menthol-enrich oil via optimization through single factorial design to enhance their organoleptic profile and biological activities. Res Chem Intermed 49, 3909–3931 (2023). https://doi.org/10.1007/s11164-023-05056-w

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