Pangesti, Laras (2019) Sintesis Senyawa 3-(10-bromodesil)-2-metil-5-metoksi-1,4-benzokuinon serta Uji Kelarutan dalam Oktanol-Air. Sarjana thesis, Universitas Brawijaya.
Abstract
Sintesis senyawa 3-(10-bromodesil)-2-metil-5-metoksi-1,4-benzokuinon dilakukan melalui dua tahap reaksi yaitu reaksi substitusi metoksi dan reaksi bromoalkilasi. Reaksi metoksi senyawa 2-metil-1,4-benzokuinon (MBQ) dilakukan menggunakan katalis ZnCl2 dan pelarut metanol membentuk senyawa 2-metil-5-metoksi-1,4-benzokuinon (MMBQ) menghasilkan rendemen 1,052 %. Dilanjutkan dengan reaksi bromoalkilasi (C10) menggunakan asam bromoandekanoat pada senyawa MMBQ menghasilkan senyawa 3-(10-bromodesil)-2-metil-5-metoksi-1,4-benzokuinon (BMMBQ) dengan yield 0,764 %. Karakterisasi produk sintesis menggunakan spektrofotometer FT-IR dan 1H-NMR sesuai dengan karakteristik struktur senyawa 2-metil-5-metoksi-1,4-benzokuinon (MMBQ) dan senyawa 3-(10-bromodesil)-2-metil-5-metoksi-1,4-benzokuinon (BMMBQ). Selanjutnya uji kelarutan senyawa 3-(10-bromodesil)-2-metil-5-metoksi-1,4-benzokuinon (BMMBQ) dalam oktanol-air. Hasil analisis menunjukkan BMMBQ memiliki kelarutan lebih tinggi dalam fasa oktanol dibandingkan dengan fasa air dengan nilai Log P = 3,03. Nilai Log P dari produk BMMBQ lebih besar dibandingkan senyawa timokuinon (Log P = 2,15) menunjukkan bahwa produk BMMBQ memiliki kemampuan menembus membran yang lebih baik dibandingkan senyawa timokuinon.
English Abstract
Synthesis of 3-(10-bromodesil)-2-methyl-5-methoxy-1,4-benzoquinone was carried out through two reaction routes, that is methoxy substitution and bromoalkylation reaction. Substitution of methoxy was carried out using ZnCl2 as catalyst and methanol as solvent gave 1.052 % yield of 2-methyl-5-methoxy-1,4-benzoquinone (MMBQ). The bromoalkylation reaction (C10) using bromundecanoic acid to MMBQ compound gave 0,764 % yield of 3-(10-bromodecyl)-2-methyl-5methoxy-1,4-benzoquinone (BMMBQ). Characterization of synthesized product using spectrophotometer FT-IR and 1H-NMR are in accordance with the chemical structure of 2-methyl-5-methoxy-1,4-benzoquinone (MMBQ) and 3-(10-bromodesil)-2-methyl-5-methoxy-1,4-benzoquinone (BMMBQ). Furthermore, solubility tests of BMMBQ in octanol-water showed that BMMBQ has greater solubility in octanol phase than in the water phase gave Log P= 3,03. The partition coefficient (Log P) value of BMMBQ compound is higher than that of thymoquinone (Log P = 2.15) thus BMMBQ compound is expected to have better ability as drug candidate.
Other obstract
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| Item Type: | Thesis (Sarjana) |
|---|---|
| Identification Number: | SKR/MIPA/2019/485/052001649 |
| Uncontrolled Keywords: | sintesis, benzokuinon, bromoalkilasi, lipofilisitas, Synthesis, benzoquinone, bromoalkylation, lipophilicity |
| Subjects: | 500 Natural sciences and mathematics > 542 Techniques, procedures, apparatus, equipment, materials > 542.3 Testing and measuring |
| Divisions: | Fakultas Matematika dan Ilmu Pengetahuan Alam > Kimia |
| Depositing User: | Budi Wahyono Wahyono |
| Date Deposited: | 10 Aug 2020 08:02 |
| Last Modified: | 10 Aug 2020 08:02 |
| URI: | http://repository.ub.ac.id/id/eprint/179255 |
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