| Peer-Reviewed

Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative

Received: 5 July 2021     Accepted: 27 July 2021     Published: 23 November 2021
Views:       Downloads:
Abstract

Background: Cinnamic acid is a white crystalline substance, chemically known as 2(E)-3-phenylprop-2-enoicacid or benzopropenoic acid. It is a mono-carboxylic acid naturally occurring in plants with low toxicity and serves as a flavoring agent in the food, pharmaceutical and perfumery industries. Objectives: The rising incidence of deleterious and harmful effects of free radicals in the human body leading to wide ranging disease conditions such as diabetes, cardiovascular ailments, cancers, hay-fever amongst many others necessitated this present study. Method: The acid was subjected to the acetylation reaction using acetic anhydride in acetic acid. In addition, the acid and the resultant derivative were screened for antioxidant activity using the DPPH (2, 2-diphenyl-1-picrylhydrazylhydrate) test. The comparison of the observed activities was also done. Results: The acetylation of the acid led to a derivative which has been identified to be cinnamyl acetate using the IR spectral technique. Both the cinnamic acid and acetyl derivative demonstrated remarkably significant antioxidant activity of IC50 at 0.18 and 0.16 µg/mL respectively which compare favorably with 0.12 µg/mL elicited by Vitamin C (a standard antioxidant drug). Conclusion: The obtained results indicate that acetylation slightly enhances the antioxidant activity of cinnamic acid.

Published in International Journal of Bioorganic Chemistry (Volume 6, Issue 2)
DOI 10.11648/j.ijbc.20210602.13
Page(s) 26-29
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), 2021. Published by Science Publishing Group

Keywords

Cinnamic Acid, Acetylation, Cinnamyl Acetate, Derivative, Antioxidant Activity

References
[1] Lei, L., Hudgins, W. R., Shack, S., Yin, M. Q., Samid, D., Cinnamic acid: A natural product with potential use in cancer intervention. Inter. J. Of Cancer, 1995, 62 (3), 345-350.
[2] Lobo, U., Patil, A., Phatak, A., Chandra, N., Free radicals, antioxidants and functional foods: impact on human health. Pharmacol. Rev., 2010, 4 (8), 77118-77126. www.http://doi.org/10.4103/0973-7847.70902.
[3] Sova, M., Antioxidant and antimicrobial activities of cinnamic acid and derivatives. Mini Rev. In Med. Chem., 2012, 12, 749-767. www.http://doi.org/10.2174/“Antioxidant activity”.8955712799829276.
[4] Oladimeji, H. O., Aniekeme, E. E., Arthur, J. S., Taiwo, E. A., Evaluation of antioxidant activity of cinnamic acid and some of its derivatives. Eur. Chem. Bull, 2019, 8 (7), 224-226. www.http://DOI:10.17628/ecb.2019.8.224-226.
[5] Olugbade, T. A., Adesanya, S. A., Prieurianoside, a protolimonoid glucoside from the leaves of Trichilia prieuriana, Phytochemistry, 2000, 54, 867-870.
[6] Chris, I. A., Laboratory organic chemistry: Techniques, qualitative analysis, organic preparations and spectroscopy, 17th edition, 2010, pp. 55-56.
[7] B. P., British pharmacopeia. The pharmaceutical press, London, appendix VA, A109, 1993, p. 754.
[8] Olaniyi, A. A., Principles of quality assurance and pharmaceutical analysis. Mosuro publishers, 2000, pp. 151-158, 216-217, 264-269 and 443-457.
[9] Olaniyi. A., Ogungbamila, F. O., Experimental pharmaceutical chemistry. Shaneson C. I. limited, 1991, pp. 49-52.
[10] Nagalapur, S. K., Paramjyothi, S., In-vitro antioxidant activity of Launaea pinnatifida Cass leaves. The Bioscan, 2010, 5 (1), 105-108. www.http:thebioscan.in/journals/abs2010.5nl_105_108htm.
[11] Guangrong, H., Jiaxin, J., Dehui, D., Anti-oxidative and antibacterial activity of the methanol extract of Artemisia anomala S. Moore. Afri. J. Biotech., 2008, 7 (9), 1335-1338. www.http://doi.org/10.1011060.8245andrep.repl.
[12] Lebeau, J., Furman, G., Bernier, J. L., Durietz, P., Teissier, E., Cotelle, N., Antioxidant properties of di-tert-butylhydroxylated flavonoids. Free-Radical Biology and Med., 2000, 29 (9), 900-912. https://doi.org/10.1016/s0891-5849(00)00390-7.
[13] Leitao, G. G., Leitao, S. G., Vilegas, W., Z. Quick preparative separation of natural naphthoquinones with antioxidant activity by high speed countercurrent chromatography, Z. Naturforsch, 2002, 57C, 1051-1055. www.https://doi.org/10.1515/znc-2002-11-1217.
[14] Bunta, G. W., Ingold, R. U., β-carotene: An unusual type of lipid antioxidant. Sci., 1984, 224, 569-573. https://doi.org/10.1126/science.6710156.
[15] Dapkevicius, A., Vanskulons, R., Van-Beek, T. A., Linssen, J.P., Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in Lithuania. J. Sci. Food Agric., 1998, 77 (1), 140-146. https://doi.org/10.1002/(sici)1097-0010(199805)77:1<140::aid-jsfa18>3.3.co;2-b.
Cite This Article
  • APA Style

    Olawale Hakeem Oladimeji, Promise Omoridion Owere, Paschal Chidera Anthony. (2021). Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative. International Journal of Bioorganic Chemistry, 6(2), 26-29. https://doi.org/10.11648/j.ijbc.20210602.13

    Copy | Download

    ACS Style

    Olawale Hakeem Oladimeji; Promise Omoridion Owere; Paschal Chidera Anthony. Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative. Int. J. Bioorg. Chem. 2021, 6(2), 26-29. doi: 10.11648/j.ijbc.20210602.13

    Copy | Download

    AMA Style

    Olawale Hakeem Oladimeji, Promise Omoridion Owere, Paschal Chidera Anthony. Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative. Int J Bioorg Chem. 2021;6(2):26-29. doi: 10.11648/j.ijbc.20210602.13

    Copy | Download

  • @article{10.11648/j.ijbc.20210602.13,
      author = {Olawale Hakeem Oladimeji and Promise Omoridion Owere and Paschal Chidera Anthony},
      title = {Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative},
      journal = {International Journal of Bioorganic Chemistry},
      volume = {6},
      number = {2},
      pages = {26-29},
      doi = {10.11648/j.ijbc.20210602.13},
      url = {https://doi.org/10.11648/j.ijbc.20210602.13},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijbc.20210602.13},
      abstract = {Background: Cinnamic acid is a white crystalline substance, chemically known as 2(E)-3-phenylprop-2-enoicacid or benzopropenoic acid. It is a mono-carboxylic acid naturally occurring in plants with low toxicity and serves as a flavoring agent in the food, pharmaceutical and perfumery industries. Objectives: The rising incidence of deleterious and harmful effects of free radicals in the human body leading to wide ranging disease conditions such as diabetes, cardiovascular ailments, cancers, hay-fever amongst many others necessitated this present study. Method: The acid was subjected to the acetylation reaction using acetic anhydride in acetic acid. In addition, the acid and the resultant derivative were screened for antioxidant activity using the DPPH (2, 2-diphenyl-1-picrylhydrazylhydrate) test. The comparison of the observed activities was also done. Results: The acetylation of the acid led to a derivative which has been identified to be cinnamyl acetate using the IR spectral technique. Both the cinnamic acid and acetyl derivative demonstrated remarkably significant antioxidant activity of IC50 at 0.18 and 0.16 µg/mL respectively which compare favorably with 0.12 µg/mL elicited by Vitamin C (a standard antioxidant drug). Conclusion: The obtained results indicate that acetylation slightly enhances the antioxidant activity of cinnamic acid.},
     year = {2021}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - Acetylation of Cinnamic Acid and Evaluation of Antioxidant Activity of the Resultant Derivative
    AU  - Olawale Hakeem Oladimeji
    AU  - Promise Omoridion Owere
    AU  - Paschal Chidera Anthony
    Y1  - 2021/11/23
    PY  - 2021
    N1  - https://doi.org/10.11648/j.ijbc.20210602.13
    DO  - 10.11648/j.ijbc.20210602.13
    T2  - International Journal of Bioorganic Chemistry
    JF  - International Journal of Bioorganic Chemistry
    JO  - International Journal of Bioorganic Chemistry
    SP  - 26
    EP  - 29
    PB  - Science Publishing Group
    SN  - 2578-9392
    UR  - https://doi.org/10.11648/j.ijbc.20210602.13
    AB  - Background: Cinnamic acid is a white crystalline substance, chemically known as 2(E)-3-phenylprop-2-enoicacid or benzopropenoic acid. It is a mono-carboxylic acid naturally occurring in plants with low toxicity and serves as a flavoring agent in the food, pharmaceutical and perfumery industries. Objectives: The rising incidence of deleterious and harmful effects of free radicals in the human body leading to wide ranging disease conditions such as diabetes, cardiovascular ailments, cancers, hay-fever amongst many others necessitated this present study. Method: The acid was subjected to the acetylation reaction using acetic anhydride in acetic acid. In addition, the acid and the resultant derivative were screened for antioxidant activity using the DPPH (2, 2-diphenyl-1-picrylhydrazylhydrate) test. The comparison of the observed activities was also done. Results: The acetylation of the acid led to a derivative which has been identified to be cinnamyl acetate using the IR spectral technique. Both the cinnamic acid and acetyl derivative demonstrated remarkably significant antioxidant activity of IC50 at 0.18 and 0.16 µg/mL respectively which compare favorably with 0.12 µg/mL elicited by Vitamin C (a standard antioxidant drug). Conclusion: The obtained results indicate that acetylation slightly enhances the antioxidant activity of cinnamic acid.
    VL  - 6
    IS  - 2
    ER  - 

    Copy | Download

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

  • Sections