jf8b00913_si_001.pdf (2.54 MB)
Enzymatic Preparation of a Homologous Series of Long-Chain 6‑O‑Acylglucose Esters and Their Evaluation as Emulsifiers
journal contribution
posted on 2018-03-30, 00:00 authored by Min-Yi Liang, Yongsheng Chen, Martin G. Banwell, Yong Wang, Ping LanSugar
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.