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All Journal Journal of Tropical Life Science : International Journal of Theoretical, Experimental, and Applied Life Sciences JURNAL KIMIA SAINS DAN APLIKASI Teknotan: Jurnal Industri Teknologi Pertanian Jurnal Ilmu Kimia Universitas Brawijaya Bulletin of Chemical Reaction Engineering & Catalysis Journal of Innovation and Applied Technology Jurnal Pembangunan dan Alam Lestari Natural B The Journal of Pure and Applied Chemistry Research Jurnal Penelitian Pendidikan IPA (JPPIPA) Indonesian Journal of Chemistry Indonesian Food Science and TechnologyJournal Media Akuakultur ALKIMIA : Jurnal Ilmu Kimia dan Terapan Makara Journal of Science Bulletin of Chemical Reaction Engineering & Catalysis
Siti Mariyah Ulfa
Department Of Chemistry, Faculty Of Mathematics And Natural Sciences, Brawijaya University, Jl. Veteran, Malang 65145, Indonesia
Agriculture, Biological Sciences & Forestry Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Civil Engineering, Building, Construction & Architecture Computer Science & IT Control & Systems Engineering Decision Sciences, Operations Research & Management Education Engineering Environmental Science Materials Science & Nanotechnology Medicine & Pharmacology Physics Social Sciences Other

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Journal : JURNAL KIMIA SAINS DAN APLIKASI

 1 
Effect of methyl substituent on the solubility of 1,4-benzoquinone derivatives in n-octanol/water system Siti Mariyah Ulfa; Fath Dwisari; Ade Cintyia Sally; Mohammad Farid Rahman
Jurnal Kimia Sains dan Aplikasi Vol 23, No 5 (2020): Volume 23 Issue 5 Year 2020
Publisher : Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (2428.245 KB) | DOI: 10.14710/jksa.23.5.142-146

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.
Facile synthesis of 5-Isopropyl-2,3-dimethylbenzene-1,4-diol by Friedel-Crafts and Determination of Partition Coefficient in n- Octanol/Water Siti Mariyah Ulfa; Alma Miranda; Fath Dwisari; Mohammad Farid Rahman
Jurnal Kimia Sains dan Aplikasi Vol 25, No 1 (2022): Volume 25 Issue 1 Year 2022
Publisher : Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.14710/jksa.25.1.7-12

Abstract

The wide therapeutic effect of quinone-based drugs has received considerable interest for a long time. In this research, Friedel-Crafts performed a facile synthesis of quinone derivatives using the mixture of Brønsted acid. Reflux of 2,3-dimethylhydroquinone (1), isopropanol, glacial acetic acid, and H2SO4 for 15 minutes gave yellow oil product of 5-isopropyl-2,3-dimethylbenzene-1,4-diol (2) as a major product. Characterization using Nuclear Magnetic Resonance (NMR) revealed the methine proton splitting for isopropyl at δ 3.13 ppm, which has a cross-coupling with aromatic carbon at δ 119.6 ppm suggested the substitution of a proton on quinone ring with isopropyl group. Analysis Fourier Transform Infra-Red (FT-IR) showed the broad spectrum of –OH, the vibration of CH sp3, and isopropyl groups. The minor products identified as 5-isopropyl-2,3-dimethylcyclohexa-2,5-diene-1,4-dione (3), 5-isopropyl-2,3-dimethyl-1,4 phenylene diacetate (4), and 2,3-dimethylbenzene-5,6-isopropyl-1,4-diol (5) confirmed from 2D HETCOR and MS analysis. The partition coefficient (log P) of compound 2 showed a higher solubility by 1.9-fold compared to hydroquinone 1. It is suggested that an additional methyl group increased the partition into the organic phase.
Co-Authors A.A. Ketut Agung Cahyawan W Adam Mahfud Ade Cintyia Sally Al zamzami, Ilham Misbakudin Alma Miranda Amaniyah, Amaniyah Amin, Abd Aziz Amini, Helda Wika Ananda, Regina Ridha Andi Kurniawan Andi Kurniawan Anggayasti, Wresti L. Anjani, Ryzki Martha Arda Rista Lestari Budi Kamulyan Caterina Widya Astutik Chairulita Putri Kusumaningsih Destiara, Irena Amelia Dinia Rizqi Dwijayanti Dwi Susanti, Yogita Ayu Edi Priyo Utomo Edi Priyo Utomo Edi Priyo Utomo Efani, Anton Eka Novitasari Elvina Dhiaul Iftitah Elvina Dhiaul Iftitah Elvina Dhiaul Iftitah Esya, Firdausy Amalina Fadlilah, Lilik Nur Fath Dwisari Fatma, Aliya Galisong, Ridwan Danuarta Grahadi, Rahmat Gunawan, Firza Rajasa Hapsari, Febriyana Rizky Helda Wika Amini Hermanto, Feri Eko Hermin Sulistyarti Hidayatul Mustafidah Hideki Okamoto Hideki Okamoto Iftitah, Elvina Dhiaul Indah Nur Pramesti Inra Sari Kamila, Fairuz Sarah Karimah Karimah Kyosuke Satake Kyosuke Satake Lisa Aulia, Lisa Listianingsih, Lia Lukman Hakim Lutfi Ni’matus Salamah Luthfia Ayu Dhea Maharani Pertiwi Koentjoro Mahfuzh Huda Masruri Masruri Masruri Masruri Masruri Moehammad, Khibar Syiar Moh. Farid Rahman Mohammad Elham Firdaus Mohammad Farid Rahman Mohammad Farid Rahman Momodou Salieu Sowe Momodou Salieu Sowe Muzdhalifa, Sefira Putri Nashi Widodo Nisa', Khibrun Nur Ikhtiarini Nuraini Uswatun Chasana Pangesti, Laras Pramudia, Zulkisam Pratama, Safreno Panggih Pratiwi, Rahmania Tulus Setya Prihartini, Dita Puspitasari, Rizka Dwitya Rachmat Triandi Tjahjanto Rizka Fauzia Ohorella Rizqi Alima Fabri, Ahmad Rosyadah, Nuraini Rurini Retnowati Safitri, Anna Salamah, Lutfi Ni’matus Suratmo Suratmo, Suratmo SUTRISNO Sutrisno, Sutrisno Utomo, Edi Priyo Wardani, Eris Agustin Warsito Warsito Warsito Warsito Widia Edy Kuncoro Widodo Widodo Widyananda, Muhammad Hermawan Yanuar, Adi Tiya Yosua Yosua Yulistian, Dhoni Prielananta Yusnawan, Eriyanto Yusuf Hendrawan Zahara, Izaz Aqeiluz