Sintesis, Sun Protection Factor, Aktivitas Antibakteri: Ester Asam trans-4-Metoksi- dan 3,4-Dimetoksisinamat

Pamela, Egar (2023) Sintesis, Sun Protection Factor, Aktivitas Antibakteri: Ester Asam trans-4-Metoksi- dan 3,4-Dimetoksisinamat. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Ester dari asam 4-metoksisinamat (1d) berupa isoamil 4-metoksisinamat (amiloksat)(2b) dan 2-etoksietil 4-metoksisinamat (sinoksat) (2c) merupakan senyawa yang dimanfaatkan pada tabir surya komersial. Kemampuan fotoproteksi senyawa tabir surya dapat ditingkatkan dengan penambahan gugus metoksi untuk meningkatkan cakupan perlindungan spektrum luas (broad-spectrum protection). Penelitian yang dilakukan berhasil mendapatkan dua senyawa baru turunan (2b) dan (2c) berupa isopentil (E)-3-(3,4-dimetoksifenil)akrilat (2d) dan 2-etoksietanol (E)-3-(3,4-dimetoksifenil)akrilat (2e). Ester sinamat pada umumnya disintesis dengan reaksi yang melibatkan tionil klorida. Namun, tionil klorida merupakan senyawa yang termasuk dalam daftar Chemical Weapon Convention dan Undang-Undang Republik Indonesia Nomor 9 Tahun 2008 perihal Larangan Penggunaan Bahan Kimia sebagai Senjata Kimia. Akibatnya penelitian yang akan dilakukan bertujuan untuk mendapatkan senyawa (2b-e) melalui metode esterifikasi Shiina yang tidak melibatkan tionil klorida. Metode ini dapat dilakukan secara onepot pada temperatur ruang melalui transformasi asam karboksilat berupa asam 4-metoksisinamat (1d) dan asam 3,4-dimetoksisinamat (1e) dengan isoamil alkohol (7a) atau 2-etoksietanol (7b) yang melibatkan anhidrida asam 2-metil-6-nitrobenzoat (5), 4-(dimetilamino)piridina (6) dan trietilamina sehingga diperoleh senyawa (2b-e) dengan rendemen masing-masing sebesar 89, 92, 98 dan 90%. Identifikasi struktur senyawa (2b-e) dilakukan menggunakan spektra yang diperoleh dari spektrometer NMR (1H dan 13C), FTIR dan massa resolusi tinggi. Hasil sintesis (2b-e) memberikan kemampuan fotoprotektif tinggi dengan nilai SPF berturut-turut sebesar 36,61 ± 0,06; 36,52 ± 0,11; 37,10 ± 0,03; dan 36,88 ± 0,01. Spektra UV-Vis senyawa (2b-e) masing-masing menunjukkan λmaks 310, 290, 320 dan 324 nm. Sayangnya, senyawa (2b-e) tidak menunjukkan aktivitas antibakteri terhadap Staphylococcus aureus dan Escherichia coli.
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In commercial sunscreens, esters of 4-methoxycinnamic acid (1d) in the form of isoamyl 4-methoxycinnamate (amyloxate) (2b) and 2-ethoxyethyl 4-methoxycinnamate (cinoxate) (2c) are utilized. Methoxy groups can be added to sunscreen compounds to enhance their photoprotection properties and broaden their spectrum of protection. The research was successful in obtaining compound (2b) and (2c), and their two derivatives namely isopentyl (E)-3-(3,4-dimethoxyphenyl)acrylate (2d) and 2-ethoxyethanol (E)-3-(3,4-dimethoxyphenyl)acrylate (2e). Cinnamic esters are generally synthesized by reactions involving thionyl chloride. However, the Chemical Weapons Convention and the Law of the Republic of Indonesia Number 9 of 2008 concerning the Prohibition of the Use of Chemicals as Chemical Weapons both classify thionyl chloride in the list. Therefore, the research that will be conducted to obtain compound (2b-e) using a thionyl chloride-free method called Shiina esterification. This method can be carried out in one pot at room temperature through the transformation of carboxylic acids in the form of 4-methoxycinnamic acid (1d) and 3,4-dimethoxycinnamic acid (1e) with isoamyl alcohol (7a) or 2-ethoxyethanol (7b) involving 2-methyl-6-nitrobenzoic acid anhydride (5), 4-(dimethylamino)pyridine (6) and triethylamine resulting compounds (2b-e) in 89, 92, 98 and 90% yields respectively. Compounds (2b-e) were identified using NMR (1H and 13C), FTIR, and high-resolution mass spectrometers. High photoprotective ability is shown by the synthesis results (2b–e), which have SPF values of 36.61 ± 0.06, 36.52 ± 0.11, 37.10 ± 0.03, and 36.88 ± 0.01 respectively. The UV-Vis spectra of the compounds (2b-e) showed λmax of 310, 290, 320 and 324 nm, respectively. Unfortunately, compounds (2b-e) did not exhibit antibacterial activities against Escherichia coli and
Staphylococcus aureus.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	cinnamic acid esters, sunscreen, Shiina esterification, ester asam sinamat, tabir surya, esterifikasi Shiina, SPF
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry Q Science > QD Chemistry > QD305.A2 O73 Esterification
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Egar Pamela
Date Deposited:	11 Sep 2023 01:35
Last Modified:	11 Sep 2023 01:35
URI:	http://repository.its.ac.id/id/eprint/103938

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