American Journal of Quantum Chemistry and Molecular Spectroscopy

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A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’

Received: 6 January 2022    Accepted: 27 January 2022    Published: 29 March 2022
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Abstract

Background of study: Vanillin is a white monoclinic crystalline compound whose chemical nomenclature is p-hydroxy-m-methoxy benzaldehyde. It is a phenolic aldehyde with a pleasant flavor and popularly found in vanilla beans and roasted coffee amongst many other sources. It possesses antitumor and particularly antioxidant activity which formed the essence of this study. Objectives: The insidious presence of free radicals in the human body has become a worrisome concern. These chemical species continue to plague the human cells, tissues and organs resulting in different patho-physiological conditions such as cancers and neurodegenerative disorders like Alzheimer’s disease and Parkinson’s disease amongst many other ailments. The search for novel pharmacological compounds with the aim of checking these radicals led the choice of vanillin in this present study. Methodology: Vanillin was separately subjected to some derivatization reactions namely; acetylation, O-demethylation, reduction and oxidation. The melting points, refractive indices and optical rotations of the lead compound and derivatives were obtained. The antioxidant activities of the five compounds were determined using the DPPH (2, 2-diphenyl-1-picrylhydrazyl hydrate) test. Comparison of the obtained antioxidant activities was done to determine if any improvements could be seen in the derivatives. Results: The identities of the derivatives have been revealed to be vanillyl acetate (E-1), 3, 4-dihydroxy benzaldehyde or protocatechui aldehyde (E-2), o-methoxy-p-methyl cyclohexan-1-ol (J-1) and vanillic acid (J-2) respectively using the IR spectral technique. Vanillin, E-2 and J-2 gave marginal antioxidant activity of IC50 of 0.81, 0.84 and 0.0.85 µg/mL respectively while J-1 and E-1 demonstrated moderately significant IC50 of 0.59 and 0.63 µg/mL which compare favorably with 0.44 µg/mL elicited by Vitamin C (a standard antioxidant drug). It is pertinent to point out that the obtained reduced derivative is a substituted cycloalkanol (a saturated cyclic compound) instead of a substituted phenolic compound as was expected. Conclusion: The results from this study indicate that reduction and acetylation separately enhances the antioxidant activity of vanillin.

DOI 10.11648/j.ajqcms.20220601.11
Published in American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 6, Issue 1, June 2022)
Page(s) 1-7
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This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Vanillyl Acetate, Protocatechui Aldehyde, o-methoxy-p-methyl Cyclohexan-1-ol, Antioxidant Activity

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    Olawale Hakeem Oladimeji, Ekemini Samuel Idiong, Udeme Akpan Joseph, Victor Udo Anah, Moji Taibat Bakare-Odunola, et al. (2022). A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’. American Journal of Quantum Chemistry and Molecular Spectroscopy, 6(1), 1-7. https://doi.org/10.11648/j.ajqcms.20220601.11

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    Olawale Hakeem Oladimeji; Ekemini Samuel Idiong; Udeme Akpan Joseph; Victor Udo Anah; Moji Taibat Bakare-Odunola, et al. A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’. Am. J. Quantum Chem. Mol. Spectrosc. 2022, 6(1), 1-7. doi: 10.11648/j.ajqcms.20220601.11

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    AMA Style

    Olawale Hakeem Oladimeji, Ekemini Samuel Idiong, Udeme Akpan Joseph, Victor Udo Anah, Moji Taibat Bakare-Odunola, et al. A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’. Am J Quantum Chem Mol Spectrosc. 2022;6(1):1-7. doi: 10.11648/j.ajqcms.20220601.11

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  • @article{10.11648/j.ajqcms.20220601.11,
      author = {Olawale Hakeem Oladimeji and Ekemini Samuel Idiong and Udeme Akpan Joseph and Victor Udo Anah and Moji Taibat Bakare-Odunola and Stanislaus Ngaitad Njinga and Saad Toyin Abdullahi},
      title = {A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’},
      journal = {American Journal of Quantum Chemistry and Molecular Spectroscopy},
      volume = {6},
      number = {1},
      pages = {1-7},
      doi = {10.11648/j.ajqcms.20220601.11},
      url = {https://doi.org/10.11648/j.ajqcms.20220601.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajqcms.20220601.11},
      abstract = {Background of study: Vanillin is a white monoclinic crystalline compound whose chemical nomenclature is p-hydroxy-m-methoxy benzaldehyde. It is a phenolic aldehyde with a pleasant flavor and popularly found in vanilla beans and roasted coffee amongst many other sources. It possesses antitumor and particularly antioxidant activity which formed the essence of this study. Objectives: The insidious presence of free radicals in the human body has become a worrisome concern. These chemical species continue to plague the human cells, tissues and organs resulting in different patho-physiological conditions such as cancers and neurodegenerative disorders like Alzheimer’s disease and Parkinson’s disease amongst many other ailments. The search for novel pharmacological compounds with the aim of checking these radicals led the choice of vanillin in this present study. Methodology: Vanillin was separately subjected to some derivatization reactions namely; acetylation, O-demethylation, reduction and oxidation. The melting points, refractive indices and optical rotations of the lead compound and derivatives were obtained. The antioxidant activities of the five compounds were determined using the DPPH (2, 2-diphenyl-1-picrylhydrazyl hydrate) test. Comparison of the obtained antioxidant activities was done to determine if any improvements could be seen in the derivatives. Results: The identities of the derivatives have been revealed to be vanillyl acetate (E-1), 3, 4-dihydroxy benzaldehyde or protocatechui aldehyde (E-2), o-methoxy-p-methyl cyclohexan-1-ol (J-1) and vanillic acid (J-2) respectively using the IR spectral technique. Vanillin, E-2 and J-2 gave marginal antioxidant activity of IC50 of 0.81, 0.84 and 0.0.85 µg/mL respectively while J-1 and E-1 demonstrated moderately significant IC50 of 0.59 and 0.63 µg/mL which compare favorably with 0.44 µg/mL elicited by Vitamin C (a standard antioxidant drug). It is pertinent to point out that the obtained reduced derivative is a substituted cycloalkanol (a saturated cyclic compound) instead of a substituted phenolic compound as was expected. Conclusion: The results from this study indicate that reduction and acetylation separately enhances the antioxidant activity of vanillin.},
     year = {2022}
    }
    

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  • TY  - JOUR
    T1  - A Cycloalkanol from Derivatization Studies on Vanillin: Evaluation of Antioxidant Activity of Obtained Derivatives’
    AU  - Olawale Hakeem Oladimeji
    AU  - Ekemini Samuel Idiong
    AU  - Udeme Akpan Joseph
    AU  - Victor Udo Anah
    AU  - Moji Taibat Bakare-Odunola
    AU  - Stanislaus Ngaitad Njinga
    AU  - Saad Toyin Abdullahi
    Y1  - 2022/03/29
    PY  - 2022
    N1  - https://doi.org/10.11648/j.ajqcms.20220601.11
    DO  - 10.11648/j.ajqcms.20220601.11
    T2  - American Journal of Quantum Chemistry and Molecular Spectroscopy
    JF  - American Journal of Quantum Chemistry and Molecular Spectroscopy
    JO  - American Journal of Quantum Chemistry and Molecular Spectroscopy
    SP  - 1
    EP  - 7
    PB  - Science Publishing Group
    SN  - 2994-7308
    UR  - https://doi.org/10.11648/j.ajqcms.20220601.11
    AB  - Background of study: Vanillin is a white monoclinic crystalline compound whose chemical nomenclature is p-hydroxy-m-methoxy benzaldehyde. It is a phenolic aldehyde with a pleasant flavor and popularly found in vanilla beans and roasted coffee amongst many other sources. It possesses antitumor and particularly antioxidant activity which formed the essence of this study. Objectives: The insidious presence of free radicals in the human body has become a worrisome concern. These chemical species continue to plague the human cells, tissues and organs resulting in different patho-physiological conditions such as cancers and neurodegenerative disorders like Alzheimer’s disease and Parkinson’s disease amongst many other ailments. The search for novel pharmacological compounds with the aim of checking these radicals led the choice of vanillin in this present study. Methodology: Vanillin was separately subjected to some derivatization reactions namely; acetylation, O-demethylation, reduction and oxidation. The melting points, refractive indices and optical rotations of the lead compound and derivatives were obtained. The antioxidant activities of the five compounds were determined using the DPPH (2, 2-diphenyl-1-picrylhydrazyl hydrate) test. Comparison of the obtained antioxidant activities was done to determine if any improvements could be seen in the derivatives. Results: The identities of the derivatives have been revealed to be vanillyl acetate (E-1), 3, 4-dihydroxy benzaldehyde or protocatechui aldehyde (E-2), o-methoxy-p-methyl cyclohexan-1-ol (J-1) and vanillic acid (J-2) respectively using the IR spectral technique. Vanillin, E-2 and J-2 gave marginal antioxidant activity of IC50 of 0.81, 0.84 and 0.0.85 µg/mL respectively while J-1 and E-1 demonstrated moderately significant IC50 of 0.59 and 0.63 µg/mL which compare favorably with 0.44 µg/mL elicited by Vitamin C (a standard antioxidant drug). It is pertinent to point out that the obtained reduced derivative is a substituted cycloalkanol (a saturated cyclic compound) instead of a substituted phenolic compound as was expected. Conclusion: The results from this study indicate that reduction and acetylation separately enhances the antioxidant activity of vanillin.
    VL  - 6
    IS  - 1
    ER  - 

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Author Information
  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Ilorin, Ilorin, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Ilorin, Ilorin, Nigeria

  • Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Ilorin, Ilorin, Nigeria

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