Synthesis and Characterization of N-Methyl Fatty Hydroxamic Acids from Ketapang Seed Oil Catalyzed by Lipase.

Dedy Suhendra,Hajidi Hajidi,Erin Ryantin Gunawan

doi:10.3390/molecules24213895

Abstract

N-methyl fatty hydroxamic acid (N-MFHA), which is a derivative of hydroxamic acid (HA), was synthesized from ketapang seed oil (Terminalia catappa L.). In general, HAs have wide applications due to their chelating properties and biological activities. N-MFHAs were synthesized using immobilized lipase (Lipozyme TL IM) in biphasic medium which was the ketapang seed oil dissolved in hexane and N-methylhydroxylamine dissolved in water. The products were characterized through color testing and FT-IR spectroscopy after purification. Various factors affecting the enzyme activity investigated in the study included the effect of incubation time, the amount of lipase used, and the temperature. On the basis of the results, the optimum conditions for the synthesis of N-MFHA obtained are 25 h of incubation time, a temperature of 40 °C, and a ratio of 1:100 for the amount of enzyme (g)/oil (g). At the optimum conditions of the reaction, 59.7% of the oils were converted to N-MFHA.

Highlights

According to [1], hydroxamic acid (HA), represented by the general formula, R-CO-NHOH, is a compound derived from oxoacid by replacing the –OH in it by –NHOH, and its hydrocarbyl derivatives
On the basis of a literature review, it is evident that many studies have been carried out involving the production of HA from various feedstocks, which are available as commercial products, the long chain HA have not been commercially available
The edible oils that have been used as a raw material for the synthesis of Fatty hydroxamic acids (FHA) are soybean oil [19] and palm oil [20]

Summary

Introduction

According to [1], hydroxamic acid (HA), represented by the general formula, R-CO-NHOH, is a compound derived from oxoacid by replacing the –OH in it by –NHOH, and its hydrocarbyl derivatives. As a metal binding group, HA are widely used as a metalloenzyme inhibitor, including tyrosinase inhibitors [3], histone deacetylase inhibitors [4,5,6,7], and HIV-integrase inhibitors [8]. On the basis of a literature review, it is evident that many studies have been carried out involving the production of HA from various feedstocks, which are available as commercial products, the long chain HA have not been commercially available They are widely used as surfactants in the pharmaceutical and soap industries [18]. Fatty hydroxamic acids (FHA), one of the derivatives of long chain HA, have been synthesized with the use of both edible and non-edible vegetable oils. The non-edible oil that has been used for the synthesis of FHA is ketapang kernel oil [21]

Methods

Results

Conclusion