Aminolysis of linoleic and salicylic acid derivatives with Candida antarctica lipase B: A solvent-free process to obtain amphiphilic amides for cosmetic application

• An enzymatic and solvent-free process was developed in order to produce amphiphilic molecules for cosmetic application.
• The fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecyl-2-hydroxybenzamide (5) were synthesized through aminolysis reactions.
• The reactions were catalyzed by Candida antarctica lipase B. Reactions were carried out in a solvent-free process, at 65 °C and reduced pressure (50 mbar).
• The products were monitored by HPLC analysis.
• The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0/mol of acyl donor group substrate and an equimolar substrates ratio (1:1).

In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecyl-2-hydroxybenzamide (5), respectively derived from linoleic acid and salicylic acid were synthesized through aminolysis reactions catalyzed by Candida antarctica lipase B. These amphiphilic compounds receive great attention from cosmetic industry due to a range of beneficial properties for skin. The aminolysis reactions were performed with the esters ethyl linoleate (1) and ethyl salicylate (4) as acyl group donors and the fatty compound N-dodecylamine (2) as the nucleophilic substrate. The aminolysis reactions were carried out in a solvent-free process, which is beneficial from an environmental and economical perspective, at 65 °C and reduced pressure (50 mbar). Parameters as enzyme amount and substrates molar ratios were investigated and the products were monitored by HPLC analysis. The conversion rates were measured through disappearance of ethyl linoleate and ethyl salicylate. The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0 g/mol of acyl donor group substrate and an equimolar substrates ratio (1:1). The products characterization was performed by High Resolution Mass Spectrometry, Infrared spectroscopy and Nuclear Magnetic Ressonance. This work reveals that enzymatic synthesis provides an attractive way for the cosmetic industrial production of fatty amides, which may represent key ingredients to maintain and/or restore a healthy skin.

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