Synthesis of 5-(4-bromobutyl)-2, 3-dimethyl-1, 4-benzoquinone and the Solubility Test in n-Octanol/Water Partition System. Issue 1 (May 2020)

• Record Type: Journal Article
• Authors: Zuhroh, Nadiyah; Ulfa, Siti Mariyah
• Is Part Of: IOP conference series. Volume 833:Issue 1(2020)
• Publication Date: 2020-05
• Subjects: Materials science -- Periodicals; 620.1105
• DOI: 10.1088/1757-899X/833/1/012056
• Languages: English
• ISSNs: 1757-8981

Abstract

Abstract: The modification structure of 1, 4-benzoquinone is fascinating in the frame of drug design. The solubility properties of a new drug are important, especially for oral drug administration. The 2-isopropyl-5-methyl-1, 4-benzoquinone (known as thymoquinone) which is the major constituent in Nigella sativa seed extract is known as an active compound with poor lipophilicity. Here, we reported the synthesis of 5-(4-bromobutyl)-2, 3-dimethyl-1, 4-benzoquinone which analog with thymoquinone having higher lipophilicity. The synthesis proposed by oxidation reaction of 2, 3-dimethyl-1, 4-hydroquinone (1 ) with H2 SO4 followed by bromoalkylation reaction using bromopentanoic acid in the presence of AgNO3 and (NH4 )2 S2 O8 . The oxidation product 2, 3-dimethyl-1, 4-benzoquinone (2 ) and alkylated-quinone 5-(4-bromobutyl)-2, 3-dimethyl-1, 4-benzoquinone (3 ) were obtained in 52.64% and 5.85%, respectively. The FTIR analysis of 3 showed the additional C-Br stretching at 562 cm −1 . The solubility test in n -octanol/water system using HPLC gave the log P value of 5-(4-bromobutyl)-2, 3-dimethyl-1, 4-benzoquinone (3 ) is 2.99, higher than thymoquinone. By this result, it is suggested that the modification of 1, 4-benzoquinone by bromo alkylating agent increased the solubility of the compound.