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Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin

Received: 12 May 2015    Accepted: 29 May 2015    Published: 11 June 2015
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Abstract

The synthesis of myristicin ketone from myristicin has been achieved through conversion of allyl group to ketone. Myristicin was isolated from nutmeg oil. The reaction of myristicin with mercury acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline solution sodium borohydride produced myristicin alcohol. Myristicin alcohol was oxidized with PCC at 40 0C for 90 minutes, followed by purified with saturated potassium disulphite yield myristicin ketone (3-methoxy-4,5-methylenedioxyphenyl)-2-propanone (68.32%).

Published in Science Journal of Chemistry (Volume 3, Issue 3)
DOI 10.11648/j.sjc.20150303.15
Page(s) 62-66
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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

Myristicin Ketone, Myristicin, Nutmeg Oil

References
[1] Muchtaridi, Subarnas, A, Apriyantono, A, Mustarichie, R, Identification of Compounds in the Essential Oil of Nutmeg Seeds (Myristica fragrans, Houtt) That Inhibit Locomotor Activity in Mice, Int. J. Mol. Sci, 2010, 11, 4771-4781.
[2] Lee, J. Y and Park, Anti-Inflammatory Effect of Myristicin on RAW 264.7 Macrophages Stimulated with Polyinosinic-Polytidylic Acid, Molecules 2011, 16, 7132-7142
[3] French, L.G, The Sassafras Tree and Designer Drugs, J.Chem.Educ, 1995.72, (6) 484-491
[4] Sohilait, H. J., Sastrohamidjojo, H., Sabirin, M and Gossert, J.S, Synthesis of Secondary Alcohol Compounds from Safrole and Methyleugenol, Indo. J. Chem, 2003, 3 (3), 176 – 178
[5] Sohilait, H. J., Sastrohamidjojo, H., Sabirin, M and Gossert, J.S, Synthesis of Safryl Ketone from Safrole, Indo. J. Chem, 2004, 4 (1), 58-61.
[6] Sohilait, H. J., Sastrohamidjojo, H., Sabirin, M and Gossert, J.S, Synthesis of Analog L-α-Methyl DOPA from Eugenol, Indo. J. Chem, 2005, 5 (3), 198-2002.
[7] Brown, H.C and Geoghegen, Jr, P.J, 1970, The Oxymercuration-Demercuration of Representative Olefins in an Aqueous System. A Convenient Mild Procedure for Markonikov Hydration of the Carbon-Carbon Double Bond, J. Org.Chem, 1970, 6, 1844–1850.
[8] Brown, H.C and Lynch, G.J, Oxymercuration-Demercuration of Methoxy, Hydroxy, and Acetoxy-Substitued Alkenes, J. Org. Chem, 1981, 6, (3), 531-538.
[9] Corey, E.J and Suggs, J.W, Pyridinium Chlorochromate. An Efficient Reagen for Oxidation of Primary and Secondary Alkohols To Carbonyl Compounds, Tetrahedron Letters, 1975 (31), 2647-2650.
[10] Servi, S and Acar, A, An Investigation of the Reaction of Substituted Homoallylic Alcohols with Various Oxidation Reagents, Molecules, 2002, 7, 104-111.
[11] Trikojus, V. M and D. E. White, Synthesis of Myristicin, J. Chem. Soc. 1949, 436-439.
[12] Shulgin, A. T,. Composition of the Myristicin Fraction from Oil of Nutmeg, Nature, 1963, (4805), 379l.
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  • APA Style

    Hanoch Julianus Sohilait, Healthy Kainama. (2015). Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin. Science Journal of Chemistry, 3(3), 62-66. https://doi.org/10.11648/j.sjc.20150303.15

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    ACS Style

    Hanoch Julianus Sohilait; Healthy Kainama. Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin. Sci. J. Chem. 2015, 3(3), 62-66. doi: 10.11648/j.sjc.20150303.15

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    AMA Style

    Hanoch Julianus Sohilait, Healthy Kainama. Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin. Sci J Chem. 2015;3(3):62-66. doi: 10.11648/j.sjc.20150303.15

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  • @article{10.11648/j.sjc.20150303.15,
      author = {Hanoch Julianus Sohilait and Healthy Kainama},
      title = {Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin},
      journal = {Science Journal of Chemistry},
      volume = {3},
      number = {3},
      pages = {62-66},
      doi = {10.11648/j.sjc.20150303.15},
      url = {https://doi.org/10.11648/j.sjc.20150303.15},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20150303.15},
      abstract = {The synthesis of myristicin ketone from myristicin has been achieved through conversion of allyl group to ketone. Myristicin was isolated from nutmeg oil. The reaction of myristicin with mercury acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline solution sodium borohydride produced myristicin alcohol. Myristicin alcohol was oxidized with PCC at 40 0C for 90 minutes, followed by purified with saturated potassium disulphite yield myristicin ketone (3-methoxy-4,5-methylenedioxyphenyl)-2-propanone (68.32%).},
     year = {2015}
    }
    

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    T1  - Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin
    AU  - Hanoch Julianus Sohilait
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    DO  - 10.11648/j.sjc.20150303.15
    T2  - Science Journal of Chemistry
    JF  - Science Journal of Chemistry
    JO  - Science Journal of Chemistry
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    AB  - The synthesis of myristicin ketone from myristicin has been achieved through conversion of allyl group to ketone. Myristicin was isolated from nutmeg oil. The reaction of myristicin with mercury acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline solution sodium borohydride produced myristicin alcohol. Myristicin alcohol was oxidized with PCC at 40 0C for 90 minutes, followed by purified with saturated potassium disulphite yield myristicin ketone (3-methoxy-4,5-methylenedioxyphenyl)-2-propanone (68.32%).
    VL  - 3
    IS  - 3
    ER  - 

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Author Information
  • Department of Chemistry Faculty of Mathematic and Natural Science, Pattimura Univerisity, Ambon, Indonesia

  • Departement of Chemistry Education, Faculty of Training and Education, Pattimura University, Ambon, Indonesia

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