Wahyuni, Sri (2018) Sintesis Senyawa [10-(2,4-dimetil-3,6-dioksosikloheksa-1,4- dien-1-il)desil]trifenilfosfonium bromida dan Penentuan Koefisien Partisi dalam Sistem Oktanol-Air. Sarjana thesis, Universitas Brawijaya.
Abstract
Timokuinon merupakan senyawa turunan benzokuinon yang memiliki bioaktivitas sebagai antioksidan, antiinflamasi, antikanker, antidiabetes dan antimikroba. Modifikasi struktur turunan benzokuinon banyak dilakukan untuk meningkatkan bioavaibilitas senyawanya. Pada penelitian ini modifikasi senyawa 2,6-dimetil-1,4- benzokuinon dilakukan dengan penambahan gugus alkil sebanyak sepuluh karbon (C10) melalui reaksi alkilasi menggunakan asam bromoundekanoat dan penambahan kation fosfonium melalui reaksi substitusi menggunakan trifenilfosfin. Reaksi alkilasi menghasilkan senyawa 2-(10-bromodesil)-3,5-dimetilsikloheksa-2,5-dien-1,4-dion (BDQ) dan reaksi substitusi menghasilkan senyawa [10-(2,4-dimetil- 3,6-dioksosikloheksa-1,4-dien-1-il)desil]trifenilfosfonium bromida (TFB). Berdasarkan analisis menggunakan spektrofotometer UVVis, FTIR, spektrometer 1H-NMR dan 13C-NMR terbentuk produk BDQ sebesar 28,18% dan produk TFB sebesar 12,52%. Penentuan nilai koefisien partisi dihasilkan nilai log P timokuinon, BDQ dan TFB masing-masing 2,50; 4,97 dan 3,03. Hal ini menunjukkan bahwa TFB dan BDQ merupakan senyawa yang lebih mudah menembus membran dibandingkan timokuinon
English Abstract
Thymoquinone is one of benzoquinone derivative that has bioactivity as an antioxidant, anti-inflammatory, anticancer, antidiabetic and antimicrobial. Structure modification of benzoquinone have been widely explored in order to increase its bioavailability. In this research, modification of 2,6-dimethyl-1,4- benzoquinone was performed by the addition of carbons (C10) alkyl groups by alkylation reaction using bromoundecanoic acid and substitution of bromin by phosphonium cations. The alkylation reaction gave 2-(10-bromodesil)-3,5-dimethylcyclohexa-2,5-dien- 1,4-dione (BDQ) compound and the substitution reaction yields [10- (2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl]triphenylphos phonium bromide (TFB). Based on analysis using UV-Vis spectrophotometer, FTIR spectrophotometer, 1H-NMR and 13C-NMR spectrometers, the BDQ was obtain in 28.18% yield, where as TFB in 12.52% yield. Based on the coefficient partition calculation using HPLC, log P of tymoquinone, BDQ and TFB is 2.50; 4.97 and 3.03, respectively. It showed that TFB and BDQ are compounds that more easily to penetrate the membrane than thymoquinone.
Other obstract
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| Item Type: | Thesis (Sarjana) |
|---|---|
| Identification Number: | SKR/MIPA/2018/291/051807051 |
| Uncontrolled Keywords: | timokuinon, benzokuinon, alkilasi, substitusi kation fosfonium, koefisien partisi, thymoquinone, benzoquinone, alkylation, substitution phosphonium cation, partition coefficient |
| Subjects: | 500 Natural sciences and mathematics > 512 Algebra > 512.7 Number theory > 512.73 Analytic number theory |
| Divisions: | Fakultas Matematika dan Ilmu Pengetahuan Alam > Kimia |
| Depositing User: | Nur Cholis |
| Date Deposited: | 19 Jun 2020 06:38 |
| Last Modified: | 22 Oct 2021 08:40 |
| URI: | http://repository.ub.ac.id/id/eprint/168468 |
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