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Effect of methyl substituent on the solubility of 1,4-benzoquinone derivatives in n-octanol/water system

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Brawijaya University, Malang, Indonesia

Received: 28 Oct 2019; Revised: 26 Apr 2020; Accepted: 27 Apr 2020; Published: 31 May 2020.
Open Access Copyright 2020 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
The solubility of the compound is a crucial task for new drug design. Quinone is a promising candidate to develop as a new drug. In this research, the synthesis of 1,4-benzoquinone derivatives, that is, 2-(5-bromoamyl)-3,5-dimethyl-1,4-benzoquinone (2a) and 2-(5-bromoamyl)-5-methyl-1,4-benzoquinone (2b) were carried out by decarboxylation and insertion reaction of alkyl bromides. The product 2a and 2b are purified using SiO2 gel column chromatography and analyzed by UV-Visible, FT-IR, and NMR. The yield of 2a is 13.75%, and 2b is 4.04%. The solubility of 2a and 2b, expressed by log P, is measured in the n-octanol/water (3:7 (v/v)) system by the shake flask method. The log P of 2a and 2b are 2.99 and 1.36, respectively. It is showed that the log P of 2a is higher compared to 2b. The presence of two methyl substituents on the quinone ring of 2a supports the increase of hydrophobicity of the compound in the n-octanol/water system.
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Keywords: 1,4-benzoquinone; decarboxylation; bioavailability; coefficient partition
Funding: Brawijaya University

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