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

Autor(es)

Mouad, Ana Maria ^{[1, 2]} ; Taupin, Delphine ^[1] ; Lehr, Laurent ^[1] ; Yvergnaux, Florent ^[1] ; Meleiro Porto, Andre Luiz ^[2]

Afiliação do(s) autor(es)

^[1] BioEurope Grp Solabia, Route Oulins 28260, Anet, Eure Et Loir - France

^[2] Univ Sao Paulo, Inst Quim Sao Carlos, Ave Joao Dagnone 1100, BR-13563120 Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC; v. 126, p. 64-68, APR 2016.
• Citações Web of Science: 14

Resumo

In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecy1-2-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 degrees 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. (C) 2016 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 04/09498-2 - Caracterização estrutural, identificação e quantificação de substâncias orgânicas e moléculas bioativas por cromatografia em fase líquida acoplada a espectrometria de massas tandem (LC-MS/MS) com equipamento híbrido quadrupolo-tempo de voo
• Beneficiário: Fernando Mauro Lanças
• Modalidade de apoio: Auxílio à Pesquisa - Programa Equipamentos Multiusuários