Lipase-catalyzed synthesis of dilauryl azelate ester: process optimization by artificial neural networks and reusability study

Khairudin, Nurshafira; Basri, Mahiran; Masoumi, Hamid Reza Fard; Samiun, Wan Sarah; Samson, Shazwani

doi:10.1039/c5ra16623c

Cited by 12 publications

(10 citation statements)

References 35 publications

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“…Moreover, high dosage pharmaceutical preparations lead to side effects associated to the acid character of the molecule. Therefore, the enzymatic synthesis of lauryl esters [19,20] have been described with the aim of improving its compatibility respect to other ingredients of cosmetic and dermatologic formulations. The enzymatic synthesis of poly(glycerolazelate) have been also reported in patent US005962624A [21] but in all cases the synthesis were catalyzed by means of the adsorbed immobilized lipase Novozyme 435 and the option of carrying out the process in two steps was not considered.…”

Section: Introductionmentioning

confidence: 99%

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

et al. 2022

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The lipase‐catalyzed polycondensation of azelaic acid and glycerol is investigated according to a Design‐of‐Experiment approach that helps to elucidate the effect of experimental variables on monomer conversion, Mn and regioselectivity of acylation of glycerol. Chemometric analysis shows that after 24 h the reaction proceeds regardless of the presence of the enzyme. Accordingly, the biocatalyst was removed after a first step of synthesis and the chain elongation continued at 80 °C. That allowed the removal of the biocatalyst and the preservation of its activity: pre‐requites for efficient applicability at industrial scale. The experimental study, combined with docking‐based computational analysis, provides rational guidelines for the optimization of the regioselective acylation of glycerol. The process is scaled up to 73.5 g of monomer. The novelty of the present study is the rigorous control of the reaction conditions and of the integrity of the immobilized biocatalyst, which serve to avoiding any interference of free enzyme or fines released in the reaction mixture. The quantitative analysis of the effect of experimental conditions and the overcoming of some major technical bottlenecks for the scalability of enzymatic polycondensation opens new scenarios for industrial exploitation.

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Section: Introductionmentioning

confidence: 99%

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

et al. 2022

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“…network ANN-based design of experiment [58] and by central composite rotatable design [59]. The optimization of the process parameters included the enzyme amount, reaction time, reaction temperature, and molar ratio of substrates.…”

Section: Enzymatic Synthesis Of Azelaic Acid Based Esters and Polyestersmentioning

confidence: 99%

“…Hydrolytic enzymes and lipases were employed for the synthesis of esters and polyesters of AzA, also with the aim of improving its compatibility, with respect to other ingredients of cosmetic and dermatologic formulation. It is known that AzA suffers from low-solubility, high melting point and large dosage requirement, which limit wide application in cosmetics and pharmaceutical products [ 58 ]. Moreover, some side effects are associated with the acid character of the molecule, demonstrated by high dosage pharmaceutical preparations.…”

Section: Azelaic Acid In the Synthesis Of Bio-based Polymersmentioning

confidence: 99%

“…Khairudin et al synthesized dilauryl azelate ester by using Novozyme 453 as catalyst. The synthesis was optimized in two reports, one by using an artificial neural network ANN-based design of experiment [ 58 ] and by central composite rotatable design [ 59 ]. The optimization of the process parameters included the enzyme amount, reaction time, reaction temperature, and molar ratio of substrates.…”

Section: Azelaic Acid In the Synthesis Of Bio-based Polymersmentioning

confidence: 99%

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Azelaic Acid: A Bio-Based Building Block for Biodegradable Polymers

et al. 2021

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Azelaic acid is a dicarboxylic acid containing nine C atoms, industrially obtained from oleic acid. Besides its important properties and pharmacological applications, as an individual compound, azelaic acid has proved to be a valuable bio-based monomer for the synthesis of biodegradable and sustainable polymers, plasticizers and lubricants. This review discusses the studies and the state of the art in the field of the production of azelaic acid from oleic acid, the chemical and enzymatic synthesis of bio-based oligo and polyester and their properties, including biodegradability and biocompostability.

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“…Azelaic acid possesses antimicrobial, anti-inflammatory, and comedolytic actions with a well-established role in the treatment of acne vulgaris [ 1 ]. Currently, Azelaic acid is available in the market as a 20% azelaic acid cream for the treatment of acne vulgaris (AV) when applied twice daily, and it has been approved for use by the Food and Drug Administration (FDA) [ 2 ]. These formulations have been shown to be effective in the treatment of inflammatory (nodulocystic, papulopustular, and nodular) acne and comedonal acne, as well as in various cutaneous hyperpigmentary disorders in pharmacological applications.…”

Section: Introductionmentioning

confidence: 99%

Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology

et al. 2018

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Azelaic acid (AzA) and its derivatives have been known to be effective in the treatment of acne and various cutaneous hyperpigmentary disorders. The esterification of azelaic acid with lauryl alcohol (LA) to produce dilaurylazelate using immobilized lipase B from Candida antarctica (Novozym 435) is reported. Response surface methodology was selected to optimize the reaction conditions. A well-fitting quadratic polynomial regression model for the acid conversion was established with regards to several parameters, including reaction time and temperature, enzyme amount, and substrate molar ratios. The regression equation obtained by the central composite design of RSM predicted that the optimal reaction conditions included a reaction time of 360 min, 0.14 g of enzyme, a reaction temperature of 46 °C, and a molar ratio of substrates of 1:4.1. The results from the model were in good agreement with the experimental data and were within the experimental range (R2 of 0.9732).The inhibition zone can be seen at dilaurylazelate ester with diameter 9.0±0.1 mm activities against Staphylococcus epidermidis S273. The normal fibroblasts cell line (3T3) was used to assess the cytotoxicity activity of AzA and AzA derivative, which is dilaurylazelate ester. The comparison of the IC50 (50% inhibition of cell viability) value for AzA and AzA derivative was demonstrated. The IC50 value for AzA was 85.28 μg/mL, whereas the IC50 value for AzA derivative was more than 100 μg/mL. The 3T3 cell was still able to survive without any sign of toxicity from the AzA derivative; thus, it was proven to be non-toxic in this MTT assay when compared with AzA.

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Lipase-catalyzed synthesis of dilauryl azelate ester: process optimization by artificial neural networks and reusability study

Abstract: An application of artificial neural networks (ANNs) to predict the performance of a lipase-catalyzed synthesis for esterification of dilauryl azelate ester was carried out.

Cited by 12 publications

References 35 publications

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

Azelaic Acid: A Bio-Based Building Block for Biodegradable Polymers

Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology

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