20881-11-2Relevant articles and documents
Enzymatic Preparation of a Homologous Series of Long-Chain 6- O -Acylglucose Esters and Their Evaluation as Emulsifiers
Liang, Min-Yi,Chen, Yongsheng,Banwell, Martin G.,Wang, Yong,Lan, Ping
, p. 3949 - 3956 (2018)
Sugar fatty acid esters are nonionic surfactants that are widely exploited in the food and cosmetics industries, as well as in the oral care and medical supply fields. Accordingly, new methods for their selective synthesis and the tuning of their emulsifying properties are of considerable interest. Herein we report simple and irreversible enzymatic esterifications of d-glucose with seven fatty acid vinyl esters. The foaming and emulsifying effects of the resulting 6-O-acylglucose esters were then evaluated. In accord with expectations, when the length of the alkyl side chain associated with the 6-O-acylglucose esters increases, then their hydrophilic-lipophilic balance (HLB) values decrease, while the stabilities of the derived emulsions improve. In order to maintain good foaming properties, alkyl side chains of at least 9 to 11 carbons in length are required. In the first such assays on 6-O-acylglucose esters, most of those described herein are shown to be nontoxic to the HepG2, MCF-7, LNacp, SW549, and LO-2 cell lines.
Synthesis and evaluation of saccharide-based aliphatic and aromatic esters as antimicrobial and antibiofilm agents
Campana, Raffaella,Merli, Alessio,Verboni, Michele,Biondo, Francesca,Favi, Gianfranco,Duranti, Andrea,Lucarini, Simone
, (2020/01/11)
A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different development times of selected food-borne pathogens (E. coli, L. monocytogenes, S. aureus, S. enteritidis). The antibiofilm activity during biofilm formation resulted in the following: mannose C10 > lactose biphenylacetate > glucose C10 > lactose C10. Among them, mannose C10 and lactose biphenylacetate showed an inhibition for E. coli 97% and 92%, respectively. At MICs values, no toxicity was observed on Caco-2 cell line for all the examined compounds. Overall, based on these results, all the sugar-based monoesters showed an interesting profile as safe antimicrobial agents. In particular, mannose C10 and lactose biphenylacetate are the most promising as possible biocompatible and safe preservatives for pharmaceutical and food applications.
Retarding activity of 6-O-Acyl-D-alloses against plant growth
Kobayashi, Miyuki,Ueda, Mariko,Furumoto, Toshio,Kawanami, Yasuhiro
experimental part, p. 216 - 217 (2010/04/04)
The retarding activity of 6-O-dodecanoyl-D-allose against rice growth was higher than that of the octanoate and the decanoate. The activities of 6-O-dodecanoyl-D-glucose,-D-mannose, and-D-galactose against rice seedlings were examined. 6-O-Dodecanoyl-D-allose exhibited the highest activity, suggesting the importance of the a-axial hydroxy group at C-3 of D-allose.
