Synthesis and Antibacterial Activity 1-Monolaurin

Abstract

An improvement of method for synthesizing 1-monolaurin from lauric acid and glycerol has been done. The reaction was carried on mol ratio between lauric acid and glycerol 1:1 at 130 °C for 6 h with variation of pTSA catalyst of 2.5%, 5%, 7.5% (w/w of lauric acid). The purification of 1-monolaurin was conducted only by extracting with alcoholic solution. The product of 1-monolaurin was obtained as a white solid with 100% of purity from variation of 2.5% and 5% of pTSA catalyst with 43.54% and 27.89% yield, respectively. 1-Monolaurin could inhibit the growth of S. aureus and E. coli bacteria at 500 µg/mL of concentration.

Monomyristin and Monopalmitin Derivatives: Synthesis and Evaluation as Potential Antibacterial and Antifungal Agents

“…From these results, monomyristin showed better antibacterial and antifungal activities compared to monopalmitin. This is probably due to the shorter carbon chain near the monolauric acid [18]. The 1-position showed high activity for both antibacterial and antifungal agent.…”

“…Monoacylglycerol can be prepared through selective glycerolysis by using an inorganic base catalyst under a nitrogen atmosphere [14]. Lauric acid and monocaprin have been investigated as intravaginal microbicides to correct sexually transmitted diseases [15,16]. In our previous work, the 1-monolaurin compound was prepared in a simple and efficient method from lauric acid and glycerol in the presence of p -toluenesulfonic acid as the catalyst [17,18].…”

“…Lauric acid and monocaprin have been investigated as intravaginal microbicides to correct sexually transmitted diseases [15,16]. In our previous work, the 1-monolaurin compound was prepared in a simple and efficient method from lauric acid and glycerol in the presence of p -toluenesulfonic acid as the catalyst [17,18]. Chinatangkul et al (2018) reported that monolaurin compounds can be loaded onto shellac nanofibers and used as an antimicrobial agent [19].…”

Preparation of Fatty Acid and Monoglyceride from Vegetable Oil

“…In this transesterification reaction, alcohol is derived from 1,2-acetonide glycerol. For example, the reaction of fatty acids ethyl ester from ethyl capric with 1,2-acetonide glycerol using Na 2 CO 3 as a catalyst will produce 1,2-acetonide-3-capryl glycerol compound 78 . Usually, the transesterification of fatty acids ethyl ester ethyl capric 18 , ethyl myristic 19 with 1,2-acetonide glycerol took place at 110 for approximately 24 hours.…”

“…The results of the analysis with Gas Chromatography showed that the 1-monolinolein product produced was cis-monolinolein 41.3 purity and trans-monolinolein 41.93 purity 32 . Deprotection reactions of 1,2-acetonide-3-alkyl glycerol can take place at room temperature for 24 hours using Amberlyst-15 in methanol 12 and ethanol 78 . The deprotection reaction in ethanol solvents is more advantageous because it can avoid the toxicity of the monoglyceride compounds produced.…”