Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase

Suhendra, Dedy; Gunawan, Erin Ryantin; Hajidi, Hajidi

doi:10.3390/molecules24213895

Cited by 5 publications

(8 citation statements)

References 25 publications

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“…Generally, reaction time affects the yield of reaction products, such as in the synthesis of 1,2-acetonide-3-lauryl glycerol. The longer the reaction time, the higher the yield of the transesterification reaction product with lipase catalyst 25,26) . The data in Fig.…”

Section: Effect Of Incubation Timementioning

confidence: 99%

“…The increase in reaction temperature damaged the active site of Lipozym TL IM to decrease the binding process of substrate and enzyme. Meanwhile, increased temperature denatures the Lipozyme TL IM protein molecule (damage to the enzyme structure) and loses its catalytic function 26) . The synthesis reaction of 1,2-acetonide-3-lauryl glycerol with Lipozym TL IM occurs effectively to produce high product yields at low temperatures (35℃) compared to K 2 CO 3 20) and Na 2 CO 3 22) in the synthesis of similar compounds.…”

Section: Effect Of Temperaturementioning

confidence: 99%

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Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM

et al. 2022

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This study aimed to synthesize α-Glycerol Monolaurate from protected glycerol (glycerol 1,2-acetonide) using Lipozym TL IM as a catalyst. In the first step, transesterification of methyl laurate and glycerol 1,2-acetonide with Lipozyme TL IM produced 1,2-acetonide-3-lauryl glycerol. In the second step, deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 produced α-Glycerol Monolaurate. Furthermore, the optimum yield (82.1%) of 1,2-acetonide-3-lauryl glycerol (light yellow liquid, purity of 92%) was achieved at a reactant mole ratio of 1, n-hexane (4 mL) with a reaction time of 12 hours, and total Lipozyme TL IM of 5% (w/w of the total weight of reactants) at a temperature of 35℃. Deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 was conducted at room temperature for 24 hours. At a melting point of 62.8℃, and purity of 100% α-Glycerol Monolaurate in the form of a white solid was obtained with a yield of 74.6% after the recrystallization of the crude product. This α-glycerol monolaurate synthesis reaction pathway can be referred to as a green α-monoacylglyceride synthesis method.

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Section: Effect Of Incubation Timementioning

confidence: 99%

Section: Effect Of Temperaturementioning

confidence: 99%

Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM

et al. 2022

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“…Metode ini bertujuan untuk mengoptimalkan hasil reaksi dengan mengamati berbagai kondisi yang dipengaruhi oleh beberapa variabel yaitu waktu reaksi, molar rasio, jumlah enzim dan suhu reaksi terhadap persen hasil yang didapatkan. Adapun pada penelitian [17] yang menggunakan metode one variable at time mendapatkan persen hasil sebesar 59,7 % sedangkan penelitian [18] yang menggunakan RSM mendapatkan persen hasil sebesar 65,7 %. Hal ini dapat menunjukkan bahwa optimasi menggunakan RSM diharapkan memiliki persen hasil yang lebih tinggi dibandingkan sintesis secara enzimatis menggunakan one variable at time.…”

Section: Pendahuluanunclassified

Optimasi Sintesis Asam Lemak Etanolamida Berbasis Minyak Ketapang Menggunakan Response Surface Methodology

2021

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Telah dilakukan optimasi sintesis asam lemak etanolamida berbasis minyak ketapang (Terminalia catappa L) menggunakan Response Surface Methodology (RSM). Asam lemak etanolamida adalah surfaktan yang banyak dibutuhkan pada industri farmasi. Sintesis asam lemak etanolamida dilakukan dengan mereaksikan minyak ketapang dan etanolamina sebagai substrat menggunakan katalis Lipozyme TL.IM. Penelitian ini bertujuan untuk mengamati interaksi antar variabel yang dapat mempengaruhi kondisi optimum dan hasil reaksi. Beberapa variabel yang dimaksud yaitu waktu reaksi, suhu reaksi, molar rasio substrat dan jumlah enzim. Metode RSM yang digunakan terdapat dalam perangkat lunak Design Expert v.7. Hasil penelitian menunjukkan model untuk mendapatkan kondisi yang optimal adalah model quadratic (p-value 0.0048/signifikan), lack of fit (p-value 0.3827 /non signifikan) dan nilai R-squared sebesar 0,7953. Kondisi optimum yang dihasilkan yaitu waktu reaksi 1,50 jam, suhu reaksi 38,10 °C, molar ratio minyak : etanolamina (1 : 20,52) gram/mol dan jumlah enzim 0.16 gram dengan prediksi dan aktual persen hasil asam lemak etanolamida secara berturut-turut sebesar 60,02 dan 64,00 %.

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“…According to Suhendra, et al (2019), one of the hydroxamic acid derivatives that can be used as chelating agents is N-methylhydroxamic fatty acids (N-MFHAs). This compound can be obtained by reacting with hydroxylamine derivatives and carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

“…This is due to the way the enzymatic works in a neutral atmosphere and low temperature, and is environmentally friendly and the enzymes used (lipases) can be reused (Moghaddam et al, 2014). Suhendra et al (2019) has successfully synthesized N-MFHAs enzymatically from ketapang seed oil with a maximum conversion percentage of 59.7%. However, the compound produced from this reaction is still composed of components that have not been separated, therefore it is necessary to separate them.…”

Section: Introductionmentioning

confidence: 99%

Separation of N-Methylhydroxamic Fatty Acids Based on Ketapang Seed Oil using High Performance Liquid Chromatography

Nirwana¹,

Suhendra

Gunawan³

2022

jppipa, pendidikan ipa, fisika, biologi, kimia

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N-methyl fatty hydroxamic acids (N-MFHAs) is a derivative of a hydroxamic acid (FHA), were synthesized from ketapang seed oil (Terminalia catappa L.) with N-methyl hydroxylamine enzymatically using immobilized lipase (Lipozyme TL IM). N-MFHAs that are synthesized are still in a mixed state of triglycerides of the ketapang seed oil. This research aims to determine the optimum conditions for the separation of N-MFHAs into their single components and their percentage composition using High Performance Liquid Chromatography (HPLC). The specification of the HPLC system includes using the reverse phase column SGE C-18 ODS-2 and UV detector 213 nm. The optimum conditions for the separation of N-MFHAs in the HPLC system include using the mobile phase of methanol 100% and flow rate of 0.25 mL/minutes with an injection volume of 20 µL and sample concentration of 10.000 ppm. The percentage of the N-MFHAs composition successfully separated using HPLC were linoleoyl-methyl-fatty hydroxamic acid (13.09%), oleoyl-methyl-fatty hydroxamic acid (62.46%), palmitoyl-methyl-fatty hydroxamic acid (19.51%), and stearoyl-methyl-fatty hydroxamic acid (4.93%).

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Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase

Cited by 5 publications

References 25 publications

Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM

Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM

Optimasi Sintesis Asam Lemak Etanolamida Berbasis Minyak Ketapang Menggunakan Response Surface Methodology

Separation of N-Methylhydroxamic Fatty Acids Based on Ketapang Seed Oil using High Performance Liquid Chromatography

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