Naringin is a flavonoid found in citrus fruits. It exhibits biological activities, such as anticancer and antioxidant effects, but it suffers from low solubility and low stability in lipophilic systems. These drawbacks lead to difficulties in the commercial application of naringin, but they can be overcome through esterification. In this study, naringin oleate was synthesized by enzymatic esterification and optimal conditions for the reaction were investigated. Experiments were conducted focusing on the following parameters: enzyme type, enzyme concentration, molar ratio of naringin to oleic acid, reaction temperature, and reaction solvent. We further confirmed the degree of esterification based on the difference in the initial and the final naringin concentrations. A conversion of 93.10% was obtained under optimized conditions (Lipozyme TL IM 10 g/L, molar ratio 1:20, reaction temperature 40 °C, acetonitrile as solvent, and 48 h reaction time). Thus, naringin oleate, a high value-added material that overcomes the low hydrophobicity of naringin and enhances its performance, was obtained through esterification of naringin using oleic acid. This study presented a method for the efficient enzymatic synthesis that could ensure high conversion within a shorter reaction time compared with that required in previously reported methods.

A composite solid propellant which generates high propulsive force in a short time is typically composed of an oxidizer, a metal fuel powder and a binder. Among these, the binder is an important component. The binder maintains the mechanical properties of propellant grains and endures several thermal and mechanical stresses in the engine. Several studies have been reported for the development of energetic propellant binders for increasing the propellant′s propulsive force. While several materials have been studied for the synthesis of energetic prepolymers, a nitramine-group-containing prepolymer is a suitable candidate because these types of prepolymers are less toxic and more cost-effective when compared to the traditional glycidyl azide polymers (GAP) and triazole-based prepolymers. Considering the lack of studies for the binder using a nitramine-group-containing prepolymers, we synthesized a nitramine-group-containing monomer and polymerized a nitramine-group-containing prepolymer. The prepolymer was then used for the preparation of the binder and its thermal and mechanical properties, as well as the effect of the plasticizer, were studied. The binder that was prepared using the prepolymer containing a nitramine-group showed very high elongation, tensile strength. Nitrate-ester (NE)-type plasticizer could reduce the glassy transition temperature (T_g)of the binder successfully. Also, high-energy is released due to the decomposition of the nitramine-group at around 245 °C, thus exhibiting the efficiency of the nitramine-group-containing prepolymer as an excellent energetic binder material.

Puerarin is a flavonoid known as a natural antioxidant found in the root of Pueraria robata. Its antioxidant, anticancer, and anti-inflammatory effects have attracted attention as a potential functional ingredient in various bioindustries. However, puerarin has limited bioavailability owing to its low lipid solubility and stability. Acylation is proposed as a synthesis method to overcome this limitation. In this study, lipase-catalyzed acylation of puerarin and various acyl donors was performed, and the enzymatic synthetic condition was optimized. Under the condition (20 g/L of Novozym 435, palmitic anhydride, 1:15, 40 °C, tetrahydrofuran (THF)), the synthesis of puerarin ester achieved a significantly high conversion (98.97%) within a short time (3 h). The molecule of the synthesized puerarin palmitate was identified by various analyses such as liquid chromatography–mass spectrometry (LC–MS), Fourier-transform infrared spectroscopy (FT-IR), and carbon-13 nuclear magnetic resonance (¹³C NMR). The lipid solubility and the radical scavenging activity were also evaluated. Puerarin palmitate showed a slight decrease in antioxidant activity, but lipid solubility was significantly improved, improving bioavailability. The high conversion achieved for puerarin esters in this study will provide the foundation for industrial applications.