OPTIMASI RENDEMEN PADA DERIVATISASI BRAZILIN DENGAN BENZIL KLORIDA MELALUI REAKSI ETERIFIKASI

PANDU CAKRA WARDHANA, - (2025) OPTIMASI RENDEMEN PADA DERIVATISASI BRAZILIN DENGAN BENZIL KLORIDA MELALUI REAKSI ETERIFIKASI. Skripsi thesis, Sekolah Tinggi Farmasi Indonesia.

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Abstract

Brazilin merupakan senyawa fenolik dari kayu secang Caesalpinia sappan L. yang memiliki aktivitas antioksidan tinggi, namun sifat fisikokimia yakni kepolaran yang kuat membatasi potensi dalam formulasi obat. Pada penelitian ini brazilin dimodifikasi menjadi benzil eternya dengan bantuan katalis natrium tert- butoksida menggantikan metode sebelumnya yang menggunakan piperidin. Identifikasi hasil derivatisasi dilakukan menggunakan KLT, spektrofotometer UV-Visibel dan FTIR. Spektrum UV menunjukkan hilangnya serapan 445 nm dan bergeser dari 286 nm ke 283 nm, menandakan penurunan konjugasi akibat konversi gugus hidroksil menjadi eter. Analisis FTIR menunjukkan perubahan gugus atau hilangnya intensitas -OH dan munculnya pita regangan C-O-C eter di 1255 ; 1026 cm-1 dan benzil 3036 cm-1 . Produk akhir menunjukan rendemen yang meningkat hingga 40,45%% dibandingkan penelitian sebelumnya <10%. Pada uji aktivitas antioksidan menunjukkan penurunan pada derivat (IC₅₀ = 86,92 μg/mL) dibandingkan isolat (IC₅₀ = 22,89 μg/mL), akibat hilangnya gugus hidroksil aktif. Meskipun aktivitas antioksidan menurun, proses derivatisasi berhasil memodifikasi struktur brazilin dengan meningkatkan potensi sifat lipofilik dan peluang pengembangan dalam sistem penghantaran obat. ----- Brazilin is a phenolic compound derived from Caesalpinia sappan L. heartwood, known for its high antioxidant activity; however, its strong polarity limits its potential in drug formulation. In this study, brazilin was modified into its benzyl ether derivative using sodium tert-butoxide as a catalyst, replacing the previously used piperidine method. The derivatization products were identified using Thin Layer Chromatography (TLC), UV–Visible spectrophotometry, and Fourier Transform Infrared (FTIR) spectroscopy. The UV spectrum showed the disappearance of absorption at 445 nm and a shift from 286 nm to 283 nm, indicating reduced conjugation due to the conversion of hydroxyl groups into ether groups. FTIR analysis revealed changes in or decreased intensity of –OH bands, along with the appearance of ether C–O–C stretching bands at 1255 and 1026 cm⁻¹, and benzyl-specific bands at 3036 cm⁻¹. The final product yield increased to 40.45%, compared to less than 10% in the previous study. Antioxidant activity testing showed a decrease in the derivative (IC₅₀ = 86.92 μg/mL) compared to the isolate (IC₅₀ = 22.89 μg/mL), attributed to the loss of active hydroxyl groups. Although antioxidant activity was reduced, the derivatization successfully modified brazilin’s structure, enhancing its lipophilic properties and potential for development in drug delivery systems.

Item Type:	Thesis (Skripsi)
Uncontrolled Keywords:	Brazilin, derivatisasi, benzil eter, natrium tert-butoksida, antioksidan. ----- Brazilin, derivatization, benzyl chloride, sodium tert-butoxide, antioxidant activity
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Divisions:	Program Studi S1 Farmasi
Depositing User:	pustakawan - -
Date Deposited:	04 Sep 2025 03:39
Last Modified:	04 Sep 2025 03:39
URI:	http://repository.stfi.ac.id/id/eprint/2763

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