Improved Synthesis of α-Glycerol Monolaurate Using Lipozyme TL IM

Abstract

This study aimed to synthesize α-Glycerol Monolaurate from protected glycerol (glycerol 1,2-acetonide) using Lipozym TL IM as a catalyst. In the first step, transesterification of methyl laurate and glycerol 1,2-acetonide with Lipozyme TL IM produced 1,2-acetonide-3-lauryl glycerol. In the second step, deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 produced α-Glycerol Monolaurate. Furthermore, the optimum yield (82.1%) of 1,2-acetonide-3-lauryl glycerol (light yellow liquid, purity of 92%) was achieved at a reactant mole ratio of 1, n-hexane (4 mL) with a reaction time of 12 hours, and total Lipozyme TL IM of 5% (w/w of the total weight of reactants) at a temperature of 35℃. Deprotection of 1,2-acetonide-3-lauryl glycerol with Amberlyst-15 was conducted at room temperature for 24 hours. At a melting point of 62.8℃, and purity of 100% α-Glycerol Monolaurate in the form of a white solid was obtained with a yield of 74.6% after the recrystallization of the crude product. This α-glycerol monolaurate synthesis reaction pathway can be referred to as a green α-monoacylglyceride synthesis method.

Glyceryl Laurate Tablets: Effect of the Excipients and Granule Size on the Tablet Quality

“…The richest source is coconut oil, but GL is also found in breast milk and palm oil. In addition to natural sources, it is produced by partial esterification of pure glycerol, chemical glycerolysis of fats and oils by inorganic catalysts, or enzymatic glycerolysis (Nandi et al, 2004;Nitbani et al, 2022;Serri and Muhammad Shahrin, 2019). The formation of an ester bond between lauric acid and glycerol occurs in two isoforms, that is, α-glyceryl laurate and β-glyceryl laurate.…”

“…In addition, a beneficial effect of GL on maintaining healthy vaginal microflora has been demonstrated as it can inhibit the pathogens Candida vaginalis and Gardenella vaginalis without adversely affecting the beneficial bacterial strains of Lactobacillus and altering the vaginal pH (Strandberg et al, 2010). Besides Candida albicans, GL exhibits antifungal activity against Aspergillus sp., Penicillium sp., Cladosporium sp., Fusarium sp., Alternaria sp., Fonsecaea pedrosoi, and Cryptococcus neoformans (Nitbani et al, 2022). The mechanism of antiviral action consists in damaging the lipid envelope of the virus.…”

“…It occurs naturally in breast milk. At an amount of about 3 mg mL -1 , it forms an important part of its lipid composition (Nitbani et al, 2022;Subroto and Indiarto, 2020). The support for the immune system happens through modulating lymphocyte production and controlling immune cell proliferation.…”