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Sintesis Asam Sinamat Dari Benzaldehida Dan Asam Malonat Dengan Katalis Dietilamina
Sintesis Asam Sinamat Dari Benzaldehida Dan Asam Malonat Dengan Katalis Dietilamina
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ISSN : 1693-5683
Abstract: Cinnamic acid is a natural compound that has known had activities as: antimicrobia;
flavour in food; soap; cosmetic; and inhibitor proliferation of caco-2 cells. Cinammic acid
compound commonly got by isolated kayu manis bark with yield 2.2%. There was a limitation
amount of cinnamic acid that got by isolation so needed another effort to get much amount of
cinnamic acid. There was an effort to get much amount of cinnamic acid that was by synthesized
it. Synthesis process was carried out by reacted benzaldehyde 45 mmol (4.9 g) and malonic acid
45 mmol (4.5 ml) with catalyzed dietylamina for 7.5 hours at 80OC. Synthetic compound was
carried out organoleptic test, solubility test, melting point test, gas chromatography, structure
elucidation with ultraviolet spectrophotometry, infrared spectrophotometry, nuclear magnetic
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resonance spectroscopy ( H-NMR), mass spectroscopy; and amount of yield.
Synthetic compound was white smooth crystal powder, and had a specific flavour with yield was
O
4.68% and melting point was 132-133 C. Solubility test showed the synthetic compound
dissolved in ethanol, methanol, chloroform, dimethyl sulfoxide, hot water, and acetone; very
difficult soluble in water. Gas chromatography chromatogram showed one peak with retention
time 13.321 minute. Based on structure elucidation conclude that synthetic compound was
cinnamic acid.
O O
H
N
O O 1. C 2 H5 C2 H 5
H OH
+
2. HCl 2N /
HO OH
O
O-
H
H
Gambar 3. Perhitungan muatan pada benzaldehida (A) dan struktur hasil resonansinya (B)
dengan program MarvinSketch 5.2.5.1
4 JULIANUS, LUCKYVANO Jurnal Farmasi Sains dan Komunitas
O O O O
H O O H C2H5 -O O- +
N+H H N C2H5
Asam malonat Garam malonat
N N H
C2H5 C2H5 C2H5 C2H5 H
C2H5 C2H5
H H
O O O O-
+
H2
+ N
C 2H 5 +-O CH O-+
C 2 H5 -O C O-+ C 2 H5 C 2H 5
N H H N C 2 H5 N+ H H N C 2H 5
H
H H C2 H5 H H H
C 2H 5 C 2H 5 C2H5
N
C 2H 5 C2 H 5
C 2H 5
H O -H + N O
H
O O
O
C2 H 5
H
C 2H 5 -O C O-+
N +H H H N C 2H 5
O
H C2 H 5 H
C 2H 5 -
O +
H N C 2H 5
C2 H5 H
H
C 2H 5
H
N
C 2H 5
C2H5 C 2H 5 H+
O -+H C2H5 O O
H +N H N
O- O -+H
O
C 2H 5 O OH H+ HO OH
- H OH
O N C 2H 5
O C 2H 5
O-
H +N C 2H 5
O-
H H +N C 2H 5
C2H5
C 2H 5 H b eta-h id ro k si k a rbo n il
H H
O O +H O O O O
H
HO OH HO OH HO O
OH
OH H+
H O
O
OH
HO
A sam sin a m at