The Effect of Isomerization Reactions in Myristicin Against Its Potential as Sunscreens Agent In-Vitro
Abstract
Myristicin has an alkenyl benzene structure with a double bond that is not conjugated with a benzene ring with good sunscreen activity, the change of the double bond to the conjugated position can be done by an isomerization reaction. This change will result in the molecule having longer delocalized double bonds and is expected to increase its activity as a sunscreen. The purpose of this study was to see the effect of changes in myristicin structure on its activity as a sunscreen.
The isomerization reaction was carried out by reflux method using 20% KOH catalyst in ethanol for 5 hours. Sunscreen activity test was carried out in-vitro using a UV spectrophotometer.
The results of the isomerization reaction obtained isomyristicin in the form of a clear light yellow liquid that dissolves in ethanol (1: 1) with a% yield of 84% and a purity of 90% E: Z (6: 1). The results of the sunscreen activity test showed changes that were not much different between myristicin and isomyristicin, which indicated that the isomerization reaction had no significant effect on sunscreen activity.
Keywords:
myristicin, isomerization reaction, sunscreen
References
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[3]. Gupta, A. D., Bansal, V. K., Babu, V., & Maithil, N. (2013). Chemistry, antioxidant and antimicrobial potential of nutmeg (Myristica fragrans Houtt). Journal of Genetic engineering and Biotechnology, 11(1), 25-31. https://doi.org/10.1016/j.jgeb.2012.12.001
[4]. Asgarpanah, J., & Kazemivash, N. (2012). Phytochemistry and pharmacologic properties of Myristica fragrans Hoyutt.: A review. African Journal of Biotechnology, 11(65), 12787-12793. https://doi.org/10.5897/AJB12.1043
[5]. Nguyen, P. H., Kang, H. W., Le, T. V. T., Chae, J., Kim, S. K., Kwon, K. I., ... & Oh, W. K. (2011). Simple process for the decrease of myristicin content from myristica fragrans (nutmeg) and its activity with amp‐activated protein kinase (ampk). Journal of Food Biochemistry, 35(6), 1715-1722.
[6]. Ansory, H. M., Sari, E. N., Nilawati, A., Handayani, S., & Aznam, N. (2020). Sunscreen and Antioxidant Potential of Myristicin in Nutmeg Essential Oils (Myristica fragrans), 138–142. https://doi.org/10.2991/ahsr.k.200523.034
[7]. Hassam, M., Taher, A., Arnott, G. E., Green, I. R., & Van Otterlo, W. A. L. (2015). Isomerization of Allylbenzenes. Chemical Reviews, 115(11), 5462–5569. https://doi.org/10.1021/acs.chemrev.5b00052
[8]. Halpern, M., Yonowich-Weiss, M., Sasson, Y., Rabinovitz, M., & HHH, O. Hydroxide ion initiated reactions in phase transfer catalysis. I. Isomerization of allylbenzene. (1981)
[9]. Halpern, M., Sasson, Y., & Rabinovitz, M.. Hydroxide ion initiated reactions under phase-transfer-catalysis conditions. 5. Isomerization of allylbenzene via hydroxide ion extraction. The Journal of Organic Chemistry, 48(7), 1022-1025. (1983). https://doi.org/10.1021/jo00155a018
[10]. Mansur JS, Breder MN, Mansur MC, Aulay RD, ” Determination of Sun protection factor by spectrophotometry," An Bras Dermatol vol 61, pp.121, 1995
[11]. de Lima, M. E. F.; Gabriel, A. J. A.; Castro, R. N. Synthesis of a New Strigol Analogue from Natural Safrole. J. Braz. Chem. Soc. 2000, 11, 371−374.
[12]. Fujimura, O.; Fu, G. C.; Grubbs, R. H. The Synthesis of Cyclic Enol Ethers Via Molybdenum Alkylidene-Catalysed Ring-Closing Metathesis. J. Org. Chem. 1994, 59, 4029−4031.
[13]. Ela, S. W.; Cram, D. J. Electrophilic Substitution at Saturated Carbon. XXX. Behavior of Phenylallylic Anions and Their Conjugate Acids. J. Am. Chem. Soc. 1966, 88, 5791−5802.
[14]. Hunter, D. H.; Cram, D. J. Electrophilic Substitution at Saturated Carbon. XXIII. Stereochemical Stability of Allyl and Vinyl Anions. J. Am. Chem. Soc. 1964, 86, 5478−5490.
[15]. Ela, S. W.; Cram, D. J. Electrophilic Substitution at Saturated Carbon. XXIX. Relationships between Position of Protonation of Allylic Anions and the Kinetic and Thermodynamic Stabilities of the Olefinic Products. J. Am. Chem. Soc. 1966, 88, 5777−5791.
[16]. Hartley, R. C.; McKiernan, G. J. Titanium Reagents for the Alkylidenation of Carboxylic Acid and Carbonic Acid Derivatives. J. Chem. Soc., Perkin Trans. 1 2002, 2763−2793.
Published
2021-04-08
Section
Articles
