Abstract
References
- [1] Ulanowska M., Olas B., Biological Properties and Prospects for the Application of Eugenol—A Review, Int J Mol Sci, 22 (7) (2021) 3671.
- [2] Yuwono M., Siswandono, Hafid A.F., Poernomo A.T., Agil M., Indrayanto G., Ebel S., Eugenol, In Analytical Profiles of Drug Substances and Excipients, 29 (2002) 149–177.
- [3] Makuch E., Nowak A., Günther A., Pełech R., Kucharski Ł., Duchnik W., Klimowicz A., Enhancement of the antioxidant and skin permeation properties of eugenol by the esterification of eugenol to new derivatives, AMB Express, 10 (1) (2020) 187.
- [4] Vilas-Boas S.M., Cordova I.W., Abranches D.O., Coutinho J.A.P., Ferreira O., Pinho S.P., Modeling the Solubility of Monoterpenoids with Hybrid and Predictive Thermodynamic Tools, Ind Eng Chem Res, 62 (12) (2023) 5326–5335.
- [5] Dinurrosifa R.S., Indriyanti E., A Green Synthesis of Acetyl Eugenol by Sonochemical Method and Potential as Anti-Inflammatory In-Vitro, JKPK (Jurnal Kimia dan Pendidikan Kimia), 7 (3) (2022) 324.
- [6] Liu C., Liu Y., Chen T., Liu J., He H., Rate constant and secondary organic aerosol formation from the gas-phase reaction of eugenol with hydroxyl radicals, Atmos Chem Phys, 19 (3) (2019) 2001–2013.
- [7] Khalil A.A., Rahman U.U., Khan M.R., Sahar A., Mehmood T., Khan M., Essential oil eugenol: sources, extraction techniques and nutraceutical perspectives, RSC Adv, 7 (52) (2017) 32669–32681.
- [8] Gökalp F., A Study on the Chemical Properties of Eugenol and Eugenol Acetate, Clove Essential Oils, Sigma J Eng & Nat Sci, 34 (3) (2016) 407–414.
- [9] Mohammadi Nejad S., Özgüneş H., Başaran N., Pharmacological and Toxicological Properties of Eugenol, Turkish Journal of Pharmaceutical Sciences, 14 (2) (2017) 201–206.
- [10] Sarrami N., Pemberton M.N., Thornhill M.H., Theaker E.D., Adverse reactions associated with the use of eugenol in dentistry, Br Dent J, 193 (5) (2002) 257–259.
- [11] Devi K.P., Nisha S.A., Sakthivel R., Pandian S.K., Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi by disrupting the cellular membrane, J Ethnopharmacol, 130 (1) (2010) 107–115.
- [12] Lane T., Anantpadma M., Freundlich J.S., Davey R.A., Madrid P.B., Ekins S., The Natural Product Eugenol Is an Inhibitor of the Ebola Virus In Vitro, Pharm Res, 36 (7) (2019) 104.
- [13] Jaganathan S.K., Supriyanto E., Antiproliferative and Molecular Mechanism of Eugenol-Induced Apoptosis in Cancer Cells, Molecules, 17 (6) (2012) 6290–6304.
- [14] Al-Sharif I., Remmal A., Aboussekhra A., Eugenol triggers apoptosis in breast cancer cells through E2F1/survivin down-regulation, BMC Cancer, 13 (1) (2013) 600.
- [15] Aburel O.M., Pavel I.Z., Dănilă M.D., Lelcu T., Roi A., Lighezan R., Muntean D.M., Rusu L.C., Pleiotropic Effects of Eugenol: The Good, the Bad, and the Unknown, Oxidative Medicine and Cellular Longevity, (1) (2021) 1–15.
- [16] Damiani C.E.N., Rossoni L.V., Vassallo D.V., Vasorelaxant effects of eugenol on rat thoracic aorta, Vascul Pharmacol, 40 (1) (2003) 59–66.
- [17] Woranuch S., Yoksan R., Eugenol-loaded chitosan nanoparticles: I. Thermal stability improvement of eugenol through encapsulation, Carbohydr Polym, 96 (2) (2013) 578–585.
- [18] Paulo F., Santos L., Double emulsion solvent evaporation approach as a novel eugenol delivery system – Optimization by response surface methodology, Ind Crops Prod, 126 (2018) 287–301.
- [19] Anand T., Anbukkarasi M., Thomas P.A., Geraldine P., A comparison between plain eugenol and eugenol-loaded chitosan nanoparticles for prevention of in vitro selenite-induced cataractogenesis, J Drug Deliv Sci Technol, 65 (2021) 102696.
Computational Study of the Structural, Electronic, and Thermodynamic Properties of the Eugenol in The Gas Phase and Solvated Environments
Abstract
In this study, the structural and electronic properties of the eugenol molecule in the gas phase and in various solvent environments (n-octanol, acetone, ethanol, acetonitrile, DMF and water) were investigated theoretically. In accordance with the quantum chemical calculations performed at the MP2/6-311G(d,p) level, NLO (Nonlinear Optical) parameters of the eugenol molecule such as dipole moment, polarizability, anisotropy, hyperpolarizability, HOMO–LUMO energy difference and bond lengths were evaluated. The obtained results revealed that the solvent polarity affects the electronic distribution and bond characteristics of the molecule. Especially in polar solvents, a significant increase was observed in the dipole moment and hyperpolarizability values of eugenol; this increases the sensitivity and interaction capacity of the molecule in optoelectronic applications. In addition, small but systematic changes in the bond lengths support the effect of solvent–solute interactions on the molecule geometry. This study contributes to the understanding of the electronic and structural behaviors of eugenol depending on the solvent environment and sheds light on its usability in application areas such as pharmacological carrier systems and optical material design.
Keywords
Eugenol Clove oil Solvent-molecule interaction HOMO–LUMO Theoretical calculations quantum chemical calculations.
References
- [1] Ulanowska M., Olas B., Biological Properties and Prospects for the Application of Eugenol—A Review, Int J Mol Sci, 22 (7) (2021) 3671.
- [2] Yuwono M., Siswandono, Hafid A.F., Poernomo A.T., Agil M., Indrayanto G., Ebel S., Eugenol, In Analytical Profiles of Drug Substances and Excipients, 29 (2002) 149–177.
- [3] Makuch E., Nowak A., Günther A., Pełech R., Kucharski Ł., Duchnik W., Klimowicz A., Enhancement of the antioxidant and skin permeation properties of eugenol by the esterification of eugenol to new derivatives, AMB Express, 10 (1) (2020) 187.
- [4] Vilas-Boas S.M., Cordova I.W., Abranches D.O., Coutinho J.A.P., Ferreira O., Pinho S.P., Modeling the Solubility of Monoterpenoids with Hybrid and Predictive Thermodynamic Tools, Ind Eng Chem Res, 62 (12) (2023) 5326–5335.
- [5] Dinurrosifa R.S., Indriyanti E., A Green Synthesis of Acetyl Eugenol by Sonochemical Method and Potential as Anti-Inflammatory In-Vitro, JKPK (Jurnal Kimia dan Pendidikan Kimia), 7 (3) (2022) 324.
- [6] Liu C., Liu Y., Chen T., Liu J., He H., Rate constant and secondary organic aerosol formation from the gas-phase reaction of eugenol with hydroxyl radicals, Atmos Chem Phys, 19 (3) (2019) 2001–2013.
- [7] Khalil A.A., Rahman U.U., Khan M.R., Sahar A., Mehmood T., Khan M., Essential oil eugenol: sources, extraction techniques and nutraceutical perspectives, RSC Adv, 7 (52) (2017) 32669–32681.
- [8] Gökalp F., A Study on the Chemical Properties of Eugenol and Eugenol Acetate, Clove Essential Oils, Sigma J Eng & Nat Sci, 34 (3) (2016) 407–414.
- [9] Mohammadi Nejad S., Özgüneş H., Başaran N., Pharmacological and Toxicological Properties of Eugenol, Turkish Journal of Pharmaceutical Sciences, 14 (2) (2017) 201–206.
- [10] Sarrami N., Pemberton M.N., Thornhill M.H., Theaker E.D., Adverse reactions associated with the use of eugenol in dentistry, Br Dent J, 193 (5) (2002) 257–259.
- [11] Devi K.P., Nisha S.A., Sakthivel R., Pandian S.K., Eugenol (an essential oil of clove) acts as an antibacterial agent against Salmonella typhi by disrupting the cellular membrane, J Ethnopharmacol, 130 (1) (2010) 107–115.
- [12] Lane T., Anantpadma M., Freundlich J.S., Davey R.A., Madrid P.B., Ekins S., The Natural Product Eugenol Is an Inhibitor of the Ebola Virus In Vitro, Pharm Res, 36 (7) (2019) 104.
- [13] Jaganathan S.K., Supriyanto E., Antiproliferative and Molecular Mechanism of Eugenol-Induced Apoptosis in Cancer Cells, Molecules, 17 (6) (2012) 6290–6304.
- [14] Al-Sharif I., Remmal A., Aboussekhra A., Eugenol triggers apoptosis in breast cancer cells through E2F1/survivin down-regulation, BMC Cancer, 13 (1) (2013) 600.
- [15] Aburel O.M., Pavel I.Z., Dănilă M.D., Lelcu T., Roi A., Lighezan R., Muntean D.M., Rusu L.C., Pleiotropic Effects of Eugenol: The Good, the Bad, and the Unknown, Oxidative Medicine and Cellular Longevity, (1) (2021) 1–15.
- [16] Damiani C.E.N., Rossoni L.V., Vassallo D.V., Vasorelaxant effects of eugenol on rat thoracic aorta, Vascul Pharmacol, 40 (1) (2003) 59–66.
- [17] Woranuch S., Yoksan R., Eugenol-loaded chitosan nanoparticles: I. Thermal stability improvement of eugenol through encapsulation, Carbohydr Polym, 96 (2) (2013) 578–585.
- [18] Paulo F., Santos L., Double emulsion solvent evaporation approach as a novel eugenol delivery system – Optimization by response surface methodology, Ind Crops Prod, 126 (2018) 287–301.
- [19] Anand T., Anbukkarasi M., Thomas P.A., Geraldine P., A comparison between plain eugenol and eugenol-loaded chitosan nanoparticles for prevention of in vitro selenite-induced cataractogenesis, J Drug Deliv Sci Technol, 65 (2021) 102696.
Details
| Primary Language | English |
|---|---|
| Subjects | Inorganic Chemistry (Other), Computational Chemistry, Theoretical Quantum Chemistry, Theoretical and Computational Chemistry (Other) |
| Journal Section | Research Article |
| Authors | |
| Submission Date | July 1, 2025 |
| Acceptance Date | October 1, 2025 |
| Publication Date | December 30, 2025 |
| Published in Issue | Year 2025 Volume: 46 Issue: 4 |
Editor