Aulia, Tinezsia (2022) Sintesis Sinamamida Baru: (E)-N’-(3-(4-Metilfenil)Akriloil) Isonikotinohidrazida Dan (E)-N’-(3-(2-Metilfenil)Akriloil) Isonikotinohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.
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Abstract
Asam sinamat (5a) dan asam sinamat tersubstitusi tersusun atas gugus fenil yang terkonjugasi dengan gugus alkena dan gugus karboksilat. Asam sinamat (5a) dan asam sinamat tersubstitusi memiliki berbagai bioaktivitas, sehingga dapat dijadikan sebagai prekusor untuk pengembangan senyawa obat. Turunan dari asam sinamat (5a) dan asam sinamat tersubstitusi berupa sinamamida merupakan kelompok senyawa dengan bioaktivitas antikanker, antitumor, anti-inflamasi, antioksidan, antimalaria, antituberkulosis, dan antidiabetes. Sinamamida pada umumnya disintesis dengan melibatkan pereaksi tionil klorida (13) yang termasuk dalam Chemical Weapons Conventions, serta Bahan Kimia Daftar-3 di Undang-undang Republik Indonesia Nomor 9 Tahun 2008 tentang penggunaan bahan kimia dan larangan penggunaan bahan kimia sebagai senjata kimia. Penelitian yang dilakukan berhasil mensintesis sinamamida baru berupa (E)-N’-(3-(4-metilfenil)akriloil)isonikotinohidrazida (17a) dan (E)-N’-(3-(2- metilfenil)akriloil)isonikotinohidrazida (17b), menggunakan metode yang tidak melibatkan pereaksi tionil klorida (13). Sinamamida (17a) diperoleh dari reaksi yang melibatkan asam 4- metilsinamat (5b) dengan rendemen 59%, sedangkan sinamamida (17a) diperoleh dari reaksi yang melibatkan asam 2-metilsinamat (5c) dengan rendemen 78%. Identifikasi struktur senyawa (17a-b) dilakukan melibatkan spektra yang diperoleh dari dengan pengukuran menggunakan spektrometer resonansi magnetik inti (1H dan 13C), spektrofotometer inframerah, dan spektrometer massa resolusi tinggi.
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Cinnamic acid (5a) and substituted cinnamic acid are composed of a phenyl group conjugated with an alkene group and a carboxylic group. Cinnamic acid (5a) and substituted cinnamic acid have various bioactivities, therefore they can be used as precursors for the development of drug compounds. The derivatives of cinnamic acid (5a) and substituted cinnamic acid in the form of cinnamamides are a group of compounds with anticancer, antitumor, anti-inflammatory, antioxidant, antimalarial, antituberculosis, and antidiabetic bioactivity. Cinnamides are generally synthesized by involving thionyl chloride reagent (13) which is included in the Chemical Weapons Conventions, as well as Chemicals List-3 in the Law of the Republic of Indonesia Number 9 of 2008 concerning the use of chemicals and the prohibition of the use of chemicals as chemical weapons. This research have succeeded in synthesizing new cinnamamides in the form of (E)-N'-(3-(4-methylphenyl)acryloyl)isonicotinohydrazide (17a) and (E)-N'-(3-(2-methylphenyl)acrylyl) isonicotinohydrazide (17b), using a method that did not involve thionyl chloride as reagent (13). Cinamamide (17a) was obtained from a reaction involving 4-methylcinnamic acid (5b) with a yield of 59%, while cinnamamide (17a) was obtained from a reaction involving 2-methylcinnamic acid (5c) with a yield of 78%. Identification of the structure of the compounds (17a-b) was carried out involving the spectra obtained from measurements using a nuclear magnetic resonance spectrometer (1H and 13C), an infrared spectrophotometer, and a high-resolution mass spectrometer.
| Item Type: | Thesis (Other) |
|---|---|
| Additional Information: | RSKi 541.39 Aul s-12022 |
| Uncontrolled Keywords: | asam 2-metilsinamat, asam 4-metilsinamat, sinamamida, reaksi. 2-methylcinnamic acid, 4-methylcinnamic acid, cinnamamide, reaction. |
| Subjects: | T Technology > TP Chemical technology > TP159.A5 Antioxidants |
| Divisions: | Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis |
| Depositing User: | Mr. Marsudiyana - |
| Date Deposited: | 05 May 2026 04:17 |
| Last Modified: | 08 May 2026 01:33 |
| URI: | http://repository.its.ac.id/id/eprint/132985 |
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