Sintesis Empat Senyawa Analog kapsaisin

Utami, Febiola Putri (2023) Sintesis Empat Senyawa Analog kapsaisin. Diploma thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Kapsaisinoid merupakan kelompok senyawa bahan alam yang identik dengan rasa pedas dan panas, serta banyak ditemui dalam genus capsicum (Solanaceae). Senyawa-senyawa ini memiliki bioaktivitas anti inflamasi, analgesik, antioksidan, anti karsinogen, fungisida, bakterisida, nematisida. Sifat pedas dan bioaktivitas tersebut menyebabkan senyawa-senyawa ini dimanfaatkan dalam makanan, elemen aktif pada senjata yang berguna sebagai pengendali kerusuhan, salep/krim. Senyawa-senyawa kapsaisinoid ditemukan dengan kadar yang rendah dengan beragam struktur, hal ini mendorong untuk dikembangkan metoda sintesis kapsaisin (1) dan senyawa-senyawa analognya. Penelitian yang dilakukan bertujuan untuk memodifikasi metoda yang dilaporkan Wang dkk (2009), dan diterapkan untuk mendapatkan senyawa-senyawa analog kapsaisin berupa N-(4-hidroksi-3-metoksibenzil)-3,3-dimetilbutanamida (30), N-(4-hidroksi-3-metoksibenzil)nonanamida (31), N1,N10-bis(4-hidroksi-3-metoksibenzil)dekanadiamida (32), dan N1,N8-bis(4-hidroksi-3-metoksi-benzil)oktanadiamida (33). Senyawa (30-33) masing-masing diperoleh dengan rendemen berturut-turut sebesar 73%, 83%, 70% dan 53%. Identifikasi struktur senyawa-senyawa (30-33) dilakukan dengan spektrometer NMR (1H,13C), spektrofotometer FTIR, dan spektrometer massa resolusi tinggi (HRESIMS).
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Capsaicinoids, a group of natural compounds synonymous with spicy and hot flavors are commonly found in the genus capsicum (Solanaceae). These compounds have anti inflammatory, analgesic, antioxidant, anti carcinogen, fungicide, bactericide, nematicide, and other bioactivities. These pungent properties and bioactivities cause these compounds to be utilized in foods, active elements in weapons useful as riot control, ointments/creams. Capsaicinoid compounds are found in low levels with a variety of structures, that encourages the development of synthesis methods of capsaicin (1) and its analog compounds. The research conducted aims to modify the method reported by Wang et al (2009) and applied to obtain capsaicin analog compounds in the form of N-(4-hydroxy-3-methoxybenzyl)-3, 3-dimethylbutanamide (30), N-(4-hydroxy-3-methoxybenzyl)nonanamide (31), N1,N10-bis(4-hydroxy-3-methoxybenzyl)decanediamide (32), and N1,N8-bis(4-hydroxy-3-methoxybenzyl)octanediamide (33). Compounds (30-33) were obtained with yields of 73%, 83%, 70% and 53%, respectively. Structural identification of compounds (30-33) was carried out by NMR spectrometer (1H,13C), FTIR spectrophotometer, and high resolution mass spectrometer (HRESIMS).

Item Type:	Thesis (Diploma)
Uncontrolled Keywords:	Asil klorida, Asil diklorida, Kapsaisinoid, Vanililamina Acyl chloride, Acyl dichloride, Capsaisinoid, 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:	Febiola Putri Utami
Date Deposited:	16 Aug 2023 04:21
Last Modified:	16 Aug 2023 04:21
URI:	http://repository.its.ac.id/id/eprint/103984

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