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

Olawale Hakeem Oladimeji; Ekemini Samuel Idiong; Udeme Akpan Joseph; Victor Udo Anah; Moji Taibat Bakare-Odunola; Stanislaus Ngaitad Njinga; Saad Toyin Abdullahi

doi:doi:10.11648/j.ajqcms.20220601.11

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

Olawale Hakeem Oladimeji, Ekemini Samuel Idiong, Udeme Akpan Joseph, Victor Udo Anah, Moji Taibat Bakare-Odunola, Stanislaus Ngaitad Njinga, Saad Toyin Abdullahi

Published in American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 6, Issue 1)

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.

Published in	American Journal of Quantum Chemistry and Molecular Spectroscopy (Volume 6, Issue 1)
DOI	10.11648/j.ajqcms.20220601.11
Page(s)	1-7
Creative Commons	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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ACS 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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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

Olawale Hakeem Oladimeji

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria
Ekemini Samuel Idiong

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria
Udeme Akpan Joseph

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria
Victor Udo Anah

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmacy, University of Uyo, Uyo, Nigeria
Moji Taibat Bakare-Odunola

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Ilorin, Ilorin, Nigeria
Stanislaus Ngaitad Njinga

Department of Pharmaceutical & Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Ilorin, Ilorin, Nigeria
Saad Toyin Abdullahi

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

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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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ACS 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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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

Copy | Download

@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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