SYNTHESIS OF n-OCTYL CINNAMATE USING DCC COUPLING REAGENT ASSISTED BY ULTRASONIC WAVE AND ANTIOXIDANT ACTIVITY TESTS

n-Octyl cinnamate is a cinnamic acid derivative that can be synthesized by an esterification reaction between cinnamic acid and n-octanol with the addition of a DCC coupling reagent (N,N'-dicyclohexylcarbodiimide), which is varied into three concentrations equivalent to 1:0.5, 1:0.75, and 1:1 moles of cinnamic acid. Ultrasonic waves assisted in the synthesis of n-octyl cinnamate at 2-8°C for 4 hours. The obtained n-octyl cinnamate was characterized by its organoleptic properties, solubility, melting point, TLC, FTIR-ATR, GC-MS, and antioxidant activity was measured using the DPPH assay. In the results, n-octyl cinnamate was obtained using DCC coupling reagent in 11.85; 14.83; and 35.83 % yields, respectively. This ester dissolves in methanol, ethanol, chloroform, ether, and n-hexane but is insoluble in water. It had a melting point range of 151.4-157.8 ºC. TLC shows that this ester has a different Rf value from that of the reactant. The FTIR spectrum showed suitable bonds with n-octyl cinnamate, as can be seen from its aromatic bands (C=C and C-H), which are characterized by the stretching of C=O and C-O bonds, aliphatic C=C, and aliphatic C-H absorptions. The results from the GC-MS analysis of the targeted compound appeared at 17.184 minutes with a 44.74% purity rate using synthesized n-ocytl cinnamate with the addition of 0,75 equivalent of DCC. The antioxidant activity test using the DPPH assay showed an IC50 value of 93.3375 ppm, indicating strong antioxidant activity. Keywords : antioxidant, esterification, ultrasonic wave, N,N?-dicyclohexylcarbodiimide, n-octyl cinnamate

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Publication Details

Journal
Medical Sains Jurnal Ilmiah Kefarmasian
Published
2025-06-11
DOI
https://doi.org/10.37874/ms.v10i2.1714
Primary Topic
Water Quality Monitoring and Analysis
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article
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article

SYNTHESIS OF n-OCTYL CINNAMATE USING DCC COUPLING REAGENT ASSISTED BY ULTRASONIC WAVE AND ANTIOXIDANT ACTIVITY TESTS

Achmad Wildan, Eka Susanti Hanhadyanaputri, Ananda Endah Devianti
Medical Sains Jurnal Ilmiah Kefarmasian
Water Quality Monitoring and Analysis
article

SYNTHESIS OF n-OCTYL CINNAMATE USING DCC COUPLING REAGENT ASSISTED BY ULTRASONIC WAVE AND ANTIOXIDANT ACTIVITY TESTS

Achmad Wildan, Eka Susanti Hanhadyanaputri, Ananda Endah Devianti
article en

Abstract

n-Octyl cinnamate is a cinnamic acid derivative that can be synthesized by an esterification reaction between cinnamic acid and n-octanol with the addition of a DCC coupling reagent (N,N'-dicyclohexylcarbodiimide), which is varied into three concentrations equivalent to 1:0.5, 1:0.75, and 1:1 moles of cinnamic acid. Ultrasonic waves assisted in the synthesis of n-octyl cinnamate at 2-8°C for 4 hours. The obtained n-octyl cinnamate was characterized by its organoleptic properties, solubility, melting point, TLC, FTIR-ATR, GC-MS, and antioxidant activity was measured using the DPPH assay. In the results, n-octyl cinnamate was obtained using DCC coupling reagent in 11.85; 14.83; and 35.83 % yields, respectively. This ester dissolves in methanol, ethanol, chloroform, ether, and n-hexane but is insoluble in water. It had a melting point range of 151.4-157.8 ºC. TLC shows that this ester has a different Rf value from that of the reactant. The FTIR spectrum showed suitable bonds with n-octyl cinnamate, as can be seen from its aromatic bands (C=C and C-H), which are characterized by the stretching of C=O and C-O bonds, aliphatic C=C, and aliphatic C-H absorptions. The results from the GC-MS analysis of the targeted compound appeared at 17.184 minutes with a 44.74% purity rate using synthesized n-ocytl cinnamate with the addition of 0,75 equivalent of DCC. The antioxidant activity test using the DPPH assay showed an IC50 value of 93.3375 ppm, indicating strong antioxidant activity. Keywords : antioxidant, esterification, ultrasonic wave, N,N?-dicyclohexylcarbodiimide, n-octyl cinnamate

Medical Sains Jurnal Ilmiah KefarmasianVol. 10(2)
Openalex Percentile: Top 84%
Water Quality Monitoring and Analysis
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