Sintesis Senyawa-senyawa Kapsaisinoid

Dwiyono, Fajar Nurharyadi (2023) Sintesis Senyawa-senyawa Kapsaisinoid. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Senyawa-senyawa kapsaisinoida yang dapat diekstrak dan dipisahkan dari buah cabai, terdapat pada konsentrasi yang rendah. Senyawa-senyawa kapsaisinoida menunjukkan aktivitas analgesik, antikanker, antiinflamasi, antioksidan, dan antiobesitas. Beberapa metode sintesis senyawa-senyawa kapsaisinoida telah dilaporkan, dan metode Wang dkk. lebih mudah dilakukan dan memberikan rendemen yang tinggi; tetapi belum sesuai dengan prinsip green chemistry perihal design for energy efficiency. Sehubungan dengan hal tersebut, maka penelitian yang dilakukan bertujuan untuk memodifikasi metode Wang dkk. yang semula reaksi dilakukan pada suhu 20°C selama kurang lebih 75 menit dan dilanjutkan pemanasan pada suhu 35-40°C untuk menuntaskan reaksi, kemudian hanya dilakukan pada suhu ruang. Reaksi substitusi nukleofilik oktanoil klorida (25) dan isobutiril klorida (26) dengan nukleofil berupa vanililamina (7) masing-masing diperoleh senyawa 18 dan 24 masing-masing berlangsung selama 30 menit dan masing-masing dengan rendemen 77% dan 48%, sedangkan reaksi substitusi nukleofilik azelaoil klorida (28) dengan dua gugus asil halida berlangsung selama 120 menit dan diperoleh senyawa 27 dengan rendemen 59%. Elusidasi struktur senyawa 24 dan 27 dilakukan dengan spektrometer resonansi magnetik inti (1H-NMR dan 13C-NMR), spektrofotometer inframerah (FTIR), dan spektrometer massa resolusi tinggi (HRMS-ESI); penetapan struktur senyawa 18 dilakukan dengan membandingkan data spektrum 1H-NMR yang diperoleh dengan data spektrum 1H-NMR yang dilaporkan Wang dkk., dan diperkuat dengan data spektrum 13C-NMR.
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Capsaicinoids can be extracted and separated from chili pepper fruit but less concentrated. Nevertheless, capsaicinoids showed analgesic, anti-cancer, anti-inflammatory, anti-oxidant, and anti-obesity activities. Several capsaicinoids synthesis methods were reported, then Wang and co-workers’ were easier to do and gave better amount of yield; but their method didn’t suit yet of green chemistry principles about design for energy efficiency. Due to that case, this research aimed to modify Wang and co-workers’ method, from reacting at temperature 20oC for almost 75 minutes and followed by heating at temperature 35-40oC to finish the reaction, changed to react at room temperature. Nucleophilic substitution reaction of octanoyl chloride (25) and isobutyryl chloride (26) with vanillylamine (7) as nucleophile giving compound 18 and 24, were reacted for 30 minutes then 77% and 48% of yield obtained respectively, while nucleophilic substitution of azelaoyl chloride (28) with two acyl halide groups were reacted for 120 minutes and giving compound 27 by 59% obtained yield. Structures elucidation of compound 24 and 27 were identified by nuclear magnetic resonance spectrometer (1H-NMR and 13C-NMR), infrared spectrophotometer (FTIR), and high resolution mass spectrometer (ESI-HRMS); compound 18 were determined by comparing spectrum datas of 1H-NMR experimental and Wang and co-workers’, strengthened by 13C-NMR spectrum.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	Asil Klorida, Green Chemistry, Senyawa-senyawa Kapsaisinoida, Vanililamina; Acyl Chlorides, Capsaicinoids, Green Chemistry, Vanillylamine
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Fajar Nurharyadi Dwiyono
Date Deposited:	03 Oct 2023 08:29
Last Modified:	03 Oct 2023 08:29
URI:	http://repository.its.ac.id/id/eprint/103641

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