SINTESIS 1-MONOMIRISTIN DARI ASAM MIRISTAT SERTA UJI AKTIVITASNYA SEBAGAI ANTIJAMUR DAN ANTIBAKTERI

ANGGIT FITRIA, Prof. Drs. Jumina, Ph.D.; Dr. Deni Pranowo, S.Si., M.Si.

2016 | Skripsi | S1 KIMIA

Telah dilakukan sintesis gliserol terproteksi, yaitu 2,2-dimetil-1,3-dioxolan-4-metanol (senyawa 1), etil miristat (senyawa 2), 2,2-dimetil-1,3-dioxolan-4-metilmiristat (senyawa 3), 1-monomiristin (senyawa 4), serta uji aktivitas antijamur dan antibakteri dari senyawa 4 secara in vitro. Senyawa 1 disintesis melalui reaksi ketalisasi gliserol dengan aseton menggunakan katalis asam p-toluensulfonat (pTSA) dan pemurnian dengan distilasi vakum. Senyawa 2 disintesis dari reaksi asam miristat dan etanol yang dikatalisis asam sulfat pekat dengan bantuan radiasi ultrasonik (sonokimia). Senyawa 3 disintesis melalui reaksi antara senyawa 1 dan senyawa 2 dengan bantuan variasi katalis basa, yaitu NaHCO3 (A), KHCO3 (B), dan K2CO3 (C), sehingga diperoleh senyawa 3A, 3B, dan 3C. Sintesis senyawa 4 dilakukan dengan cara mereaksikan senyawa 3A, 3B, dan 3C dengan etanol dan dibantu katalis asam resin penukar ion-wet Amberlyst 15, sehingga diperoleh senyawa 4A, 4B, dan 4C. Produk sintesis dianalisis menggunakan spektrofotometer FTIR, GC-MS, LC-MS, 1H-, dan 13C-NMR. Uji aktivitas antijamur dan antibakteri dilakukan pada senyawa 4 menggunakan metode difusi sumuran dengan bahan uji, antara lain jamur Candida albicans, bakteri Gram positif (Staphylococcus aureus dan Bacillus subtilis), bakteri Gram negatif (Escherechia coli dan Aggregatibacter Actinomycetemcomitans), polietilen glikol 400 20% sebagai kontrol negatif, dan 4-isopropil-3-metilfenol 1% sebagai kontrol positif. Semua hasil penelitian menghasilkan produk yang diinginkan dengan persen hasil sebagai berikut, senyawa 1 sebesar 33,70%, senyawa 2 sebesar 98,43%, senyawa 3A, 3B, dan 3C masing-masing sebesar 30,66; 43,80; dan 32,12%, serta senyawa 4A, 4B, dan 4C masing-masing 70,79; 100; dan 100%. Senyawa 4 menunjukkan adanya aktivitas antijamur dan antibakteri pada semua bakteri uji (Gram positif dan Gram negatif). Aktivitas tertinggi ditunjukkan pada konsentrasi 15% untuk jamur Candida albicans, bakteri Gram positif (Staphylococcus aureus dan Bacillus subtilis), dan bakteri Gram negatif (Escherechia coli dan Aggregatibacter Actinomycetemcomitans).

Synthesis of a protected glycerol, i.e. 2,2-dimethyl-1,3-dioxolan-4-methanol (compound 1), ethyl myristate (compound 2), 2,2-dimethyl-1,3-dioxolan-4-methylmyristate (compound 3), 1-monomyristin (compound 4), and testing the capabilities of antifungal and antibacterial activity of compound 4 in vitro have been carried out. Compound 1 was synthesized through the ketalization reaction of glycerol with acetone using p-toluenesulfonic acid (pTSA) catalyst and purification by vacuum distillation. Compound 2 was obtained by reacting myristic acid and ethanol with concentrated sulfuric acid catalyst with the aid of ultrasonic radiation (sonochemical). Compound 3 was prepared by reacting 2,2-dimethyl-1,3-dioxolan-4-methanol and ethyl myristate with the presence of some alkaline catalysts, such as NaHCO3 (A), KHCO3 (B), and K2CO3 (C), thus obtained compound 3A, 3B, and 3C. Synthesis of compound 4 was done by reacting compound 3A, 3B, and 3C with ethanol in the presence of acid catalyst ion exchange resin-wet Amberlyst 15 to obtain compound 4A, 4B, and 4C. The products of the synthesis were analyzed using FTIR, GC-MS, LC-MS, 1H- and 13C-NMR spectrophotometer. Antifungal and antibacterial activity test was done at compound 4 using the wells diffusion method towards Candida albicans fungus, Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherechia coli and Aggregatibacter Actinomycetemcomitans), polyethylene glycol 400 20% as a negative control, and 4-isopropyl-3-methylphenol 1% as a positive control. All synthesis experiments afforded the expected products in the percent yield as the following: compound 1 was 33.70%, compound 2 was 98.43%, compound 3A, 3B, and 3C were 30.66; 43.80; and 32.12% respectively, and compound 4A, 4B, and 4C were 70.79; 100; and 100% respectively. Compound 4 showed antifungal and antibacterial activity to all tested bacteria (Gram-positive and Gram-negative). The highest activity was shown at concentration of 15% for the fungus Candida albicans, Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), and Gram-negative bacteria (Escherechia coli and Aggregatibacter Actinomycetemcomitans).

Kata Kunci : 1-monomiristin, aktivitas, antibakteri, antijamur, transesterifikasi, 1-monomyristin, activity, antibacteria, antifungi, transesterification