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

Hanoch Julianus Sohilait; Healthy Kainama

doi:doi:10.11648/j.sjc.20150303.15

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

Hanoch Julianus Sohilait, Healthy Kainama

Published in Science Journal of Chemistry (Volume 3, Issue 3)

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
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), 2015. 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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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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TY  - JOUR
T1  - Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin
AU  - Hanoch Julianus Sohilait
AU  - Healthy Kainama
Y1  - 2015/06/11
PY  - 2015
N1  - https://doi.org/10.11648/j.sjc.20150303.15
DO  - 10.11648/j.sjc.20150303.15
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 62
EP  - 66
PB  - Science Publishing Group
SN  - 2330-099X
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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

Hanoch Julianus Sohilait

Department of Chemistry Faculty of Mathematic and Natural Science, Pattimura Univerisity, Ambon, Indonesia
Healthy Kainama

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

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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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TY  - JOUR
T1  - Synthesis of Myristicin Ketone (3,4-Methylenedioxy-5-Methoxyphenyl)-2-Propanone from Myristicin
AU  - Hanoch Julianus Sohilait
AU  - Healthy Kainama
Y1  - 2015/06/11
PY  - 2015
N1  - https://doi.org/10.11648/j.sjc.20150303.15
DO  - 10.11648/j.sjc.20150303.15
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 62
EP  - 66
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20150303.15
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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