Synthesis of naringin 6"-ricinoleate using immobilized lipase.

Chemistry Central Journal
Verônica M AlmeidaAlexsandro Branco

Abstract

Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica. Analysis of the 1H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative. After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments. Using immobilized lipase from C. antarctica, the best conversio...Continue Reading

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Citations

Jun 10, 2016·Applied Microbiology and Biotechnology·Io AntonopoulouVincenza Faraco
Jul 8, 2016·Revista da Escola de Enfermagem da U S P·Weslla Karla Albuquerque Silva de PaulaSuzana Lins da Silva
Aug 29, 2020·Free Radical Research·Iwona Binkowska, Sławomir Binkowski
Feb 14, 2013·Chemical Society Reviews·Patrick Adlercreutz

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Methods Mentioned

BETA
acylation
NMR
column chromatography
2D

Software Mentioned

Ezchrom Elite

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