Voltammetric sensor based on carboxylated carbon nanotubes and poly(pyrogallol red) for determination of eugenol in essential oils

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

A voltammetric sensor based on a glassy cardon electrode with a layer-by-layer combination of carboxylated multi-walled carbon nanotubes and electropolymerized pyrogallol red has been developed for the determination of eugenol in essential oils. Optimal conditions for the preparation of poly(pyrogallol red) film in potentiodynamic mode in neutral medium were found to provide the best voltammetric response of eugenol. The electrode was characterized using scanning electron microscopy and a suite of electrochemical methods. A significant improvement in the voltammetric characteristics of eugenol on the polymer-modified electrode was shown. The parameters of eugenol electrooxidation were calculated and it was shown that the reaction proceeds with the formation of o-quinone. Under the conditions of differential-pulse voltammetry in Britton-Robinson buffer with pH 2.0, the range of detectable eugenol content is 0.75-100 μM with a detection limit of 0.73 μM. High selectivity of eugenol determination in the presence of inorganic ions and typical phenolic and terpene components of essential oils was shown. The approach was successfully tested on eugenol-containing essential oils and compared with an independent method.

Авторлар туралы

A. Kalmykova

Kazan Federal University

Email: Ziyatdinovag@mail.ru

A.M. Butlerov Chemical Institute

Ресей, 420008 Kazan

G. Ziyatdinova

Kazan Federal University

Хат алмасуға жауапты Автор.
Email: Ziyatdinovag@mail.ru

A.M. Butlerov Chemical Institute

Ресей, 420008 Kazan

Әдебиет тізімі

  1. Khalil A.A., Rahman U., Khan M.R., Sahar A., Mehmood T., Khan M. Essential oil eugenol: Sources, extraction techniques and nutraceutical perspectives // RSC Adv. 2017. V. 7. № 52. P. 32669. https://doi.org/10.1039/C7RA04803C
  2. Handbook of Herbs and Spices, 2nd Ed. / Ed. Peter K.V. Cambridge: Woodhead Publishing Ltd, 2012. V. 1. 336 p.
  3. Зиятдинова Г.К., Будников Г.К. Природные фенольные антиоксиданты в биоаналитической химии: состояние проблемы и перспективы развития // Успехи химии. 2015. Т. 84. № 2. C. 194. (Ziyatdinova G.K., Budnikov H.C. Natural phenolic antioxidants in bioanalytical chemistry: State of the art and prospects of development // Russ. Chem. Rev. 2015. V. 84. № 2. P. 194. https://doi.org/10.1070/RCR4436)
  4. WHO Food Additives Series: 56. Safety Evaluation of Certain Food Additives. Geneva: WHO Press, 2006. 440 p.
  5. Ozkan S.A., Kauffmann J., Zuman P. Electroanalysis in Biomedical and Pharmaceutical Sciences: Voltammetry, Amperometry, Biosensors, Applications. Berlin/Heidelberg, Germany: Springer, 2015. 363 p. https://doi.org/10.1007/978-3-662-47138-8.
  6. Ziyatdinova G., Ziganshina E., Budnikov H. Voltammetric sensing and quantification of eugenol using nonionic surfactant self-organized media // Anal. Methods. 2013. V. 5. № 18. P. 4750. https://doi.org/10.1039/C3AY40693H
  7. Yildiz G., Aydogmus Z., Cinar M.E., Senkal F., Ozturk T. Electrochemical oxidation mechanism of eugenol on graphene modified carbon paste electrode and its analytical application to pharmaceutical analysis // Talanta. 2017. V. 173. P. 1. https://doi.org/10.1016/j.talanta.2017.05.056
  8. Wang S., Zhang T., Wang Z., Wang D., Wang Z., Sun M., Liu H. Direct electrochemistry of eugenol at a glassy carbon electrode modified with electrochemically reduced graphene oxide // Int. J. Electrochem. Sci. 2019. V. 14. № 4. P. 3618. https://doi.org/10.20964/2019.04.27
  9. Maciel J.V., Silva T.A., Dias D., Fatibello-Filho O. Electroanalytical determination of eugenol in clove oil by voltammetry of immobilized microdroplets // J. Solid State Electrochem. 2018. V. 22. № 7. P. 2277. https://doi.org/10.1007/s10008-018-3933-z
  10. Verma A., Jain R. (1-Butyl-3-methylimidazolium hexafluorophosphate) based sensor for quantification of eugenol antioxidant // Electroanalysis. 2016. V. 28. № 10. P. 2598. https://doi.org/10.1002/elan.201600228
  11. Afzali D., Zarei S., Fathirad F., Mostafavi A. Gold nanoparticles modified carbon paste electrode for differential pulse voltammetric determination of eugenol // Mater. Sci. Eng. C. 2014. V. 43. P. 97. https://doi.org/10.1016/j.msec.2014.06.035
  12. Lin X., Ni Y., Kokot S. Electrochemical mechanism of eugenol at a Cu doped gold nanoparticles modified glassy carbon electrode and its analytical application in food samples // Electrochim. Acta. 2014. V. 133. P. 484. https://doi.org/10.1016/j.electacta.2014.04.065
  13. Ziyatdinova G., Ziganshina E., Romashkina S., Budnikov H. Highly sensitive amperometric sensor for eugenol quantification based on CeO2 nanoparticles and surfactants // Electroanalysis. 2017. V. 29. № 4. P. 1197. https://doi.org/10.1002/elan.201600719
  14. Muthukutty B., Ganesamurthi J., Chen T.-W., Chen S.-M., Yu J., Liu X. A novel high-performance electrocatalytic determination platform for voltammetric sensing of eugenol in acidic media using pyrochlore structured lanthanum stannate nanoparticles // J. Ind. Eng. Chem. 2022. V. 106. P. 103. https://doi.org/10.1016/j.jiec.2021.10.015
  15. Anu Prathap M.U., Wei C., Sun S., Xu Z.J. A new insight into electrochemical detection of eugenol by hierarchical sheaf-like mesoporous NiCo2O4 // Nano Res. 2015. V. 8. № 8. P. 2636. https://doi.org/10.1007/s12274-015-0769-z
  16. Kang S.Z., Liu H., Li X., Sun M., Mu J. Electrochemical behavior of eugenol on TiO2 nanotubes improved with Cu2O clusters // RSC Adv. 2014. V. 4. № 2. P. 538. https://doi.org/10.1039/C3RA44895A
  17. Ganesamurthi J., Shanmugam R., Chen S.-M., Alagumalai K., Balamurugan M., Fan C.-H. A portable electrochemical sensor based on binary transition metal oxide (CoO/ZnO) for the evaluation of eugenol in real-time samples // Surf. Interfaces. 2023. V. 38. Article 102845. https://doi.org/10.1016/j.surfin.2023.102845
  18. Veerapandi G., Meenakshi S., Anitta S., Arul C., Ashokkumar P., Sekar C. Precise and quick detection of ascorbic acid and eugenol in fruits, pharmaceuticals and medicinal herbs using hydroxyapatite-titanium dioxide nanocomposite-based electrode // Food Chem. 2022. V. 382. Article 132251. https://doi.org/10.1016/j.foodchem.2022.132251
  19. Shi Z., Xia L., Li G., Hu Y. Platinum nanoparticles-embedded raspberry-liked SiO2 for the simultaneous electrochemical determination of eugenol and methyleugenol // Microchim. Acta. 2021. V. 188. № 7. P. 1. https://doi.org/10.1007/s00604-021-04892-0
  20. Fadillah G., Wicaksono W.P., Fatimah I., Saleh T.A. A sensitive electrochemical sensor based on functionalized graphene oxide/SnO2 for the determination of eugenol // Microchem. J. 2020. V. 159. Article 105353. https://doi.org/10.1016/j.microc.2020.105353
  21. Feng, Q., Duan K., Ye X., Lu D., Du Y., Wang C. A novel way for detection of eugenol via poly (diallyldimethylammonium chloride) functionalized graphene-MoS2 nano-flower fabricated electrochemical sensor // Sens. Actuators B. 2014. V. 192. P. 1. https://doi.org/10.1016/j.snb.2013.10.087
  22. Murtada K., Moreno V., Ríos Á., Zougagh M. Decoration of graphene oxide with copper selenide in supercritical carbon dioxide medium as a novel approach for electrochemical sensing of eugenol in various samples // J. Supercrit. Fluids. 2019. V. 153. Article 104597. https://doi.org/10.1016/j.supflu.2019.104597
  23. Luque M., Ríos A., Valcárcel M. Use of supported liquid membranes incorporated in a flow system for the direct determination of eugenol in spice samples // Analyst. 2000. V. 125. № 10. P. 1805. https://doi.org/10.1039/B001974G
  24. Wang Z., Yao Y., Zhang H., Zhang J., Ding W., Liu Z., et al. Highly water-stable PEDOT:PSS composite electrode decorated with polyvinylpyrrolidone and carbon nanotubes for sensitive detection of eugenol // Int. J. Electrochem. Sci. 2015. V. 10. № 9. P. 6997. https://doi.org/10.1016/S1452-3981(23)17325-1
  25. Naskar H., Ghatak B., Biswas S., Singh P.P., Tudu B., Bandyopadhyay R. Electrochemical detection of eugenol (EU) using polyacrylonitrile molecular imprinted polymer embedded graphite (PAN-MIP/G) electrode // IEEE Sens. J. 2019. V. 20. № 1. P. 39. https://doi.org/10.1109/JSEN.2019.2941637
  26. Yang L., Zhao F., Zeng B. Electrochemical determination of eugenol using a three-dimensional molecularly imprinted poly (p-aminothiophenol-co-p-aminobenzoic acids) film modified electrode // Electrochim. Acta. 2016. V. 210. P. 293. https://doi.org/10.1016/j.electacta.2016.05.167
  27. Ziyatdinova G., Guss E., Morozova E., Budnikov H., Davletshin R., Vorobev V., Osin Yu. Simultaneous voltammetric determination of gallic and ellagic acids in cognac and brandy using electrode modified with functionalized SWNT and poly(pyrocatechol violet) // Food Anal. Methods. 2019. V. 12. № 10. P. 2250. https://doi.org/10.1007/s12161-019-01585-6
  28. Гусс Е.В., Зиятдинова Г.К., Жупанова А.С., Будников Г.К. Вольтамперометрическое определение кверцетина и рутина при совместном присутствии на электроде, модифицированном политимолфталеином // Журн. аналит. химии. 2020. Т. 75. № 4. С. 348. https://doi.org/10.31857/S0044450220040064 (Guss E.V., Ziyatdinova G.K., Zhupanova A.S., Budnikov H.C. Voltammetric determination of quercetin and rutin in their simultaneous presence on an electrode modified with polythymolphthalein // J. Anal. Chem. 2020. V. 75. № 4. P. 526. https://doi.org/10.1134/S106193482004005X)
  29. Chernousova N., Ziyatdinova G. Electrode based on the MWCNTs and electropolymerized thymolphthalein for the voltammetric determination of total isopropylmethylphenols in spices // Micromachines. 2023. V. 14. № 3. Article 636. https://doi.org/10.3390/mi14030636
  30. Zhupanova A., Guss E., Ziyatdinova G., Budnikov H. Simultaneous voltammetric determination of flavanones using an electrode based on functionalized single-walled carbon nanotubes and polyaluminon // Anal. Lett. 2020. V. 53. № 13. P. 2170. https://doi.org/10.1080/00032719.2020.1732402
  31. Ziyatdinova G., Zhupanova A., Davletshin R. Simultaneous determination of ferulic acid and vanillin in vanilla extracts using voltammetric sensor based on electropolymerized bromocresol purple // Sensors. 2022. V. 22. № 1. Article 288. https://doi.org/10.3390/s22010288
  32. Chandrashekar B.N., Swamy B.E.K., Mahesh K.R.V., Chandra U., Sherigara B.S. Electrochemical studies of bromothymol blue at surfactant modified carbon paste electrode by using cyclic voltammetry // Int. J. Electrochem. Sci. 2009. V. 4. № 3. P. 471.
  33. Ziyatdinova G., Guss E., Yakupova E. Electrochemical sensors based on the electropolymerized natural phenolic antioxidants and their analytical application // Sensors. 2021. V. 21. № 24. Article 8385. https://doi.org/10.3390/s21248385
  34. Feng P.-S., Wang S.-M., Su W.-Y., Cheng S.-H. Electrochemical oxidation and sensitive determination of pyrogallol at preanodized screen-printed carbon electrodes // J. Chinese Chem. Soc. 2012. V. 59. № 2. P. 231. https://doi.org/10.1002/jccs.201100384
  35. Atala E., Velásquez G., Vergara C., Mardones C., Reyes J., Tapia R.A., et al. Mechanism of pyrogallol red oxidation induced by free radicals and reactive oxidant species. A kinetic and spectroelectrochemistry study // J. Phys. Chem. B. 2013. V. 117. № 17. P. 4870. https://doi.org/10.1021/jp400423w
  36. Bard A.J., Faulkner L.R. Electrochemical Methods, Fundamentals and Applications. 2nd Ed. New York: John Wiley& Sons Inc., 2001. 850 p.
  37. Lasia A. Electrochemical Impedance Spectroscopy and Its Applications. New York: Springer, 2014. 367 p. https://doi.org/10.1007/978-1-4614-8933-7
  38. Randviir E.P. A cross examination of electron transfer rate constants for carbon screen-printed electrodes using electrochemical impedance spectroscopy and cyclic voltammetry // Electrochim. Acta. 2018. V. 286. P. 179. https://doi.org/10.1016/j.electacta.2018.08.021
  39. Lopez J.C., Zon M.A., Fernández H., Granero A.M. Development of an enzymatic biosensor to determine eugenol in dental samples // Talanta. 2020. V. 210. Article 120647. https://doi.org/10.1016/j.talanta.2019.120647
  40. Backheet E.Y. Micro determination of eugenol, thymol and vanillin in volatile oils and plants // Phytochem. Anal. 1998. V. 9. № 3. P. 134. https://doi.org/10.1002/(SICI)1099-1565 (199805/06)9:3<134::AID-PCA398>3.0.CO;2-9
  41. Chemistry of Spices / Eds. Parthasarathy V.A., Chempakam B., Zachariah T.J. Oxfordshire: CABI, 2008. 445 p.

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2024