KONDISI OPTIMUM HIDROLISIS KARIOFILENA ASETAT MENJADI KARIOFILENA ALKOHOL PADA SUASANA BASA

Ajda Firasyan Shiddiq, - and Asep Kadarohman, - and Ratnaningsih Eko Sardjono, - (2025) KONDISI OPTIMUM HIDROLISIS KARIOFILENA ASETAT MENJADI KARIOFILENA ALKOHOL PADA SUASANA BASA. S1 thesis, Universitas Pendidikan Indonesia.

Abstract

Sintesis turunan kariofilena melalui pendekatan asam cenderung memicu ring rearrangement serta menurunkan selektivitas hasil reaksi akibat degradasi rangka utama kariofilena. Penelitian ini bertujuan untuk mengembangkan jalur sintesis alternatif yang lebih selektif dalam pembuatan derivat kariofilena, khususnya kariofilena alkohol, melalui reaksi hidrolisis ester dalam suasana basa menggunakan kariofilena asetat sebagai prekursor dan basa NaOH. Reaksi dilakukan dengan metode refluks menggunakan pelarut etanol, melalui optimasi tiga variabel utama yaitu suhu, mol ekuivalen NaOH, dan waktu reaksi. Proses pemisahan dilakukan dengan metode ekstraksi cair-cair menggunakan n-heksana dan pemurnian melalui evaporasi alami atau destilasi fraksinasi vakum, dilanjutkan dengan rekristalisasi menggunakan n-heksana. Karakterisasi produk dilakukan melalui morfologi kristal, serta analisis instrumentasi GC-FID, GC-MS, FTIR, ¹H-NMR, dan ¹³C-NMR. Hasil penelitian menghasilkan padatan amorf beraroma spicy-pungent dengan woody undertone. Penentuan kondisi optimum dicapai pada suhu 70 °C, mol ekuivalen NaOH 4 Ev, dan waktu reaksi 135 menit. Produk utama yang dihasilkan adalah kariofilena alkohol dengan selektivitas 98,13% berdasarkan GC-FID, serta rendemen reaksi sebesar 56,401%. Analisis GC-MS menunjukkan similarity index 69% dengan α-kariofilena alkohol, sedangkan perbandingan dengan referensi kariolan-1-ol menunjukkan kemiripan kuat dengan spektrum MS produk utama sintesis. Spektrum FTIR menegaskan keberadaan gugus –OH (3379,40 cm⁻¹) dan ikatan C–O (1057,03 dan 1018,45 cm⁻¹) dari gugus alkohol, sedangkan hasil ¹H-NMR (δ 3,740 ppm) dan ¹³C-NMR (δ 70,77 ppm) konsisten dengan proton dan karbon dari gugus alkohol di kariofilena alkohol, dan cukup identik dengan kariolan-1-ol referensi. The synthesis of caryophyllene derivatives via acidic approaches often induces ring rearrangement and reduces product selectivity due to degradation of the main caryophyllene skeleton. This study aims to develop an alternative and more selective synthetic pathway for producing caryophyllene derivatives, particularly caryophyllene alcohol, through ester hydrolysis under basic conditions using caryophyllene acetate as a precursor and NaOH as the base. The reaction was carried out under reflux in ethanol, with optimization of three main variables: temperature, molar equivalents of NaOH, and reaction time. Product separation was performed by liquid–liquid extraction using n-hexane, followed by purification through natural evaporation or vacuum fractional distillation, and recrystallization with n-hexane. Product characterization included crystal morphology analysis and instrumental methods such as GC-FID, GC-MS, FTIR, ¹H-NMR, and ¹³C-NMR. The synthesis yielded an amorphous solid with a spicy-pungent aroma and a woody undertone. Optimal conditions were determined at 70 °C, 4 molar equivalents of NaOH, and a reaction time of 135 minutes. The main product, caryophyllene alcohol, was obtained with a selectivity of 98.13% based on GC-FID and a reaction yield of 56.401%. GC-MS analysis showed a 69% similarity index with α-caryophyllene alcohol, while comparison with the reference compound caryolan-1-ol revealed a strong resemblance to the MS spectrum of the synthesized product. FTIR spectra confirmed the presence of an –OH group (3379.40 cm⁻¹) and C–O bonds (1057.03 and 1018.45 cm⁻¹) characteristic of alcohols. Furthermore, ¹H-NMR (δ 3.740 ppm) and ¹³C-NMR (δ 70.77 ppm) signals were consistent with the alcohol group in caryophyllene alcohol and closely matched those of caryolan-1-ol.

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Item Type:	Thesis (S1)
Additional Information:	https://scholar.google.com/citations?user=r2BDpiYAAAAJ&hl=en&authuser=1 ID SINTA Dosen Pembimbing: Asep Kadarohman: 5984423 Ratnaningsih Eko Sardjono: 5979503
Uncontrolled Keywords:	Kariofilena alkohol, Kariofilena asetat, hidrolisis basa, optimasi reaksi, selektivitas, GC-MS, FTIR, NMR caryophyllene alcohol, caryophyllene acetate, base hydrolysis, reaction optimization, selectivity, GC-MS, FTIR, NMR
Subjects:	Q Science > QD Chemistry
Divisions:	Fakultas Pendidikan Matematika dan Ilmu Pengetahuan Alam > Program Studi Kimia - S1 > Program Studi Kimia (non kependidikan)
Depositing User:	Ajda Firasyan Shiddiq
Date Deposited:	16 Sep 2025 02:28
Last Modified:	16 Sep 2025 02:28
URI:	http://repository.upi.edu/id/eprint/138973

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