Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity

Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco‐friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposolu...

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Published in:Biotechnology and applied biochemistry 2015-07, Vol.62 (4), p.458-466
Main Authors: Stojanović, Marija, Carević, Milica, Mihailović, Mladen, Veličković, Dušan, Dimitrijević, Aleksandra, Milosavić, Nenad, Bezbradica, Dejan
Format: Article
Language:English
Subjects:
antioxidant
Antioxidants
Ascorbic Acid - chemistry
ascorbyl ester
Candida - enzymology
Candida antarctica lipase B
Esters
fatty acid
Fatty acids
Fatty Acids - chemistry
Free Radical Scavengers - chemical synthesis
Free Radical Scavengers - chemistry
Free radicals
Fungal Proteins - chemistry
Lipase - chemistry
Lipases
Oleic acid
Scavenging
Synthesis
vitamin C
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Summary:Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco‐friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase‐catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short‐chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L−1 of lipase, 50 mM of vitamin C, 10‐fold molar excess of oleic acid, and 0.7 mL L−1 of initial water. Obtained results showed that even short‐ and medium‐chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l‐ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes.
ISSN:0885-4513
1470-8744
DOI:10.1002/bab.1296