Sintesis Senyawa Hibrid Isatin Berbasis Etil P-Metoksisinamat Hasil Isolasi dari Rimpang Kaempferia galanga Linn.

Ingeswari, Aulya Vidiana (2024) Sintesis Senyawa Hibrid Isatin Berbasis Etil P-Metoksisinamat Hasil Isolasi dari Rimpang Kaempferia galanga Linn. Masters thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Etil p-metoksisinamat (EPMS) 1, ester turunan asam sinamat, merupakan senyawa biomarker dalam rimpang Kaempferia galanga Linn. atau kencur. Senyawa 1 dapat diisolasi dari rimpang kencur dengan metode maserasi menggunakan n-heksana. Struktur senyawa 1 dapat dimodifikasi melalui transformasi gugus ester menghasilkan senyawa asil klorida yang memungkinkan untuk dikombinasi lebih lanjut dengan senyawa heterosiklik isatin 8 termodifikasi menghasilkan senyawa hibrid. Kombinasi isatin 8 teralkilasi dan etil p-metoksisinamat 1 termodifikasi menjadi senyawa hibrid dapat disintesis dengan pendekatan analisis retrosintesis. Namun, sejauh ini belum ada penelitian yang melaporkan tahap sintesis dan karakterisasi senyawa hibrid tersebut. Penelitian ini bertujuan untuk memperoleh senyawa hibrid isatin teralkilasi berbasis etil p-metoksisinamat 1 hasil isolasi dari rimpang K. galanga L. Senyawa 1 berhasil diisolasi dari rimpang K. galanga L. dengan rendemen 1,43% melalui teknik maserasi dalam pelarut n-hekana. Hidrolisis senyawa 1 dalam suasana basa memberikan senyawa asam p-metoksisinamat 2 dengan yield sebesar 91%. Lebih lanjut, p-metoksisinamoil klorida 3 berhasil diperoleh dari reaksi antara asam p-metoksisinamat 2 dengan oksalil klorida 19. Sementara itu, reaksi isatin 8 dengan benzil klorida 23 membentuk senyawa 1-benzil indolin-2,3-dion 20 (yield 86%) yang pada reaksi selanjutnya dengan hidrazin hidrat 22 menghasilkan senyawa 1-benzil-3-hidrazonoindolin-2-on 18 (yield 44%). Akhirnya, senyawa hibrid isatin berbasis etil p-metoksisinamat 1 berupa (2E,N’E)-N’-(1-benzil-2-oksoindolin-3-iliden)-3-(4-metoksifenil)akrilohidrazida 17 dengan yield sebesar 35% berhasil didapatkan dari reaksi antara p-metoksisinamoil klorida 3 dengan 1-benzil-3-hidrazonoindolin-2-on 18. Senyawa hasil isolasi dan sintesis diuji kemurnian dengan KLT sistem 3 eluen, KLT dua dimensi, dan uji titik leleh. Struktur senyawa hasil isolasi dan sintesis diidentifikasi dengan spektroskopi FTIR, NMR, dan LCMS-MS.
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Ethyl p-methoxycinnamate (EPMC) 1, an ester derivative of cinnamic acid, serves as a biomarker compound in the rhizome of Kaempferia galanga Linn. (kencur). Compound 1 can be isolated from the kencur rhizome using various methods with organic solvents. The structure of compound 1 can be modified via ester group transformation to affford acyl chloride compounds, enabling further combination with the modified heterocyclic compound isatin 8 to produce hybrid compounds. The combination of alkylated isatin 8 and modified ethyl p-methoxycinnamate 1 into hybrid compounds can be synthesized using a retrosynthetic analysis approach. However, to date, no research has reported the synthesis and characterization steps of these hybrid compounds. So, this study aimed to synthesize an alkylated isatin hybrid compound based on ethyl p-methoxycinnamate 1, isolated from the rhizome of K. galanga L. Compound 1 was successfully isolated from the rhizome of K. galanga L. with a yield of 1,43% using maceration techniques in n-hexane solvent. Hydrolysis of compound 1 in a basic condition yielded p-methoxycinnamic acid 2 with a 91% yield. Furthermore, p-methoxycinnamoyl chloride 3 was obtained from the reaction between p-methoxycinnamic acid 19 and oxalyl chloride 19. Meanwhile, the reaction of isatin 8 with benzyl chloride 23 produced 1-benzylindoline-2,3-dione 20 (yield 86%), which, in a subsequent reaction with hydrazine hydrate 22, formed 1-benzyl-3-hydrazonoindoline-2-one 18 (yield 44%). Finally, the isatin hybrid compound based on ethyl p-methoxycinnamate 1, (2E,N’E)-N’-(1-benzyl-2-oxoindoline-3-ylidene)-3-(4-methoxyphenyl)acrylohy-drazide 17, with a yield of 35%, was successfully synthesized from the reaction between p-methoxycinnamoyl chloride 3 and 1-benzyl-3-hydrazonoindoline-2-one 18. The purity of the isolated and synthesized compounds was confirmed using TLC with three eluent systems, two-dimensional TLC, and melting point determination. The structures of the isolated and synthesized compounds were characterized by FTIR, NMR, and LCMS-MS spectroscopy.

Item Type:	Thesis (Masters)
Uncontrolled Keywords:	Kaempferia galanga, etil p-metoksisinamat, isatin, senyawa hibrid, ethyl p-methoxycinnamate, isatin, hybrid compound
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Mathematics and Science > Chemistry > 47101-(S2) Master Thesis
Depositing User:	Aulya Vidiana Ingeswari
Date Deposited:	09 Aug 2024 02:35
Last Modified:	09 Aug 2024 02:35
URI:	http://repository.its.ac.id/id/eprint/114585

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