Esterifikasi Asam 2-Metilsinamat Dengan Metode Shiina

Pamela, Egar (2022) Esterifikasi Asam 2-Metilsinamat Dengan Metode Shiina. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Asam sinamat (1a), asam sinamat tersubstitusi, dan turunannya dimanfaatkan sebagai pewangi, denaturant, UV filter, UV absorber, pencerah kulit, dan anti ageing. Penelitian yang dilakukan berhasil mendapatkan dua senyawa baru berupa fenetil (E)-3-(2-tolil)akrilat (8a) dan metoksifenetil (E)-3-(2-tolil)akrilat (8b) yang merupakan hasil transformasi asam 2- metilsinamat (1c). Transformasi dilakukan dengan menerapkan metoda Shiina yang melibatkan reaksi asam 2-metilsinamat (1c), trietilamina, (dimetilamino piridina (4), anhidrida asam 2- metil-6-nitrobenzoat (5) dengan senyawa alkohol berupa fenetil alkohol (6a) dan 4- metoksifenetil alkohol (6b). Senyawa (8a) berhasil diperoleh dengan rendemen 46%, sedangkan senyawa (8b) dengan rendemen 51%. Identifikasi struktur senyawa (8a-b) dilakukan menggunakan spektra yang diperoleh dari spektrometer NMR, FTIR, UV-Vis, massa resolusi tinggi. Spektrum UV-Vis senyawa (8a-b) menunjukkan λmaks 280 nm sehingga menyerap sinar UV-B (280-315 nm) dan megindikasikan potensi dimanfaatkan sebagai tabir surya UV-B, selain potensi sebagai pewangi.
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Cinnamic acid (1a), substituted cinnamic acids, and their derivatives are used as fragrances, denaturants, UV absorbers, UV filters, skin lightening and anti-aging properties. The research has succeeded in obtaining two new compounds, namely phenethyl (E)-3-(2-tolyl)acrylate (8a) and methoxyphenethyl (E)-3-(2-tolyl)acrylate (8b) by the transformation of 2-methylcinnamic acid (1c). The transformation was carried out by applying the Shiina method which involved the reaction of 2-methylcinnamic acid (1c), triethylamine, (dimethylamino)pyridine (4), 2- methyl-6-nitrobenzoic acid anhydride (5) with an alcohol compound in the form of phenethyl alcohol (6a) and 4-methoxyphenethyl alcohol (6b). Compound (8a) was successfully obtained in 46% yield, while compound (8b) with 51% yield. Identification of the structure of the compound (8a-b) using NMR, FTIR, UV-Vis, high resolution mass spectrometer. The UV-Vis spectrum of the compound (8a-b) shows λmax 280 nm so that it absorbs UV-B radiation (280-315 nm). It indicated their potential as a UV-B sunscreen, in addition to its potential as fragrances

Item Type:	Thesis (Other)
Additional Information:	RSKi 541.39 Pam e-1 2022
Uncontrolled Keywords:	asam 2-metil sinamat, fenetil alkohol, 4-metoksifenetil alkohol, esterifikasi Shiina. 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, phenethyl alcohol, Shiina esterification
Subjects:	Q Science > QD Chemistry > QD75.2 Chemistry, Analytic
Divisions:	Faculty of Mathematics and Science > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Mr. Marsudiyana -
Date Deposited:	07 May 2026 07:45
Last Modified:	08 May 2026 01:13
URI:	http://repository.its.ac.id/id/eprint/132971

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