“Green” Synthesis of Sucrose Octaacetate and Characterization of Its Physicochemical Properties and Antimicrobial Activity

Abstract

Sucrose octaacetate (octa-O-acetylsucrose) has been synthesized by esterification of sucrose with acetic anhydride using ultrasound-assisted irradiation. This sucrose ester is a white, water-insoluble substance with a bitter taste. The FT-IR and NMR spectra confirmed acetylation and revealed the hydrophobic incorporation in sucrose molecule. Furthermore, the foamability, foam stability, emulsification and antimicrobial properties of octa-O-acetylsucrose were evaluated. Foams and 50 % (oil/water) model emulsions were prepared with 2 % (w/w) octa-O-acetylsucrose. The obtained results demonstrate the formation of emulsions and foams with high stability (50-70 %). The antimicrobial activity of octa-O-acetylsucrose was evaluated against seventeen microorganisms (Gram-positive and Gram-negative bacteria, yeasts, and fungi). Octa-O-acetylsucrose inhibited the growth of fungi Penicillium sp., Rhizopus sp. and Fusarium moniliforme at 5 mg cm -3 , and yeasts Candida albicans at 1 mg cm -3. Inhibition against Gram-positive and Gram-negative bacteria was not observed. The obtained results demonstrate the potential applications of octa-O-acetylsucrose as a foaming agent, oil-in-water emulsion stabilizer, and antifungal substance in pharmaceutical and cosmetic preparations.

New bio-amphiphilic structures of sucrose via amides linkages

“…The surface tension was measured for the series of sucrose compounds solution with different concentrations by the DuNouy ring The critical micelles concentrations CMC of the sucrose monoamide in aqueous solutions were evaluated from the across a point in surface tension versus log concentration plots at 25 • C (Nouy, 1919). All sucrose derivatives are shown an ability to reduce the surface tension with different degrees, and the results are in a good agreement with other sugar surfactants (Petkova, 2018;Zhang et al, 2014). The ability to reduce the surface tension increased with the increasing number of the carbon atoms in the hydrophobic group 32 mN/m for C 10−6 to 36 mN/m for C 12 , the ability of reducing surface tension, the solubility at room temperature and biodegradability make the sucrose compounds a good candidate for oil in water emulsi ier.…”

Comparative Study of the Emulsifying Properties of a Homologous Series of Long-Chain 6′-O-Acylmaltose Esters

“…Evaluations of the foamability and the foaming stability of esters 2−8 together with four controls were undertaken using a previously described method. 38 Thus, 10 mL of 0.2% and 0.5% w/w aqueous dispersions of each sample were placed in a 50 mL, flat-bottomed measuring cylinder and the height of solution (H 0 ) was measured before being homogenized, using a blender, at 3000 rpm for 2 min. The foam height (H 2 ) and the total height (H 1 ) were determined immediately.…”

Phytochemistry and anti‐inflammatory activity of iridoids from Dolichandrone spathacea collected in the mangrove forest of Phu Loc district, Thua Thien Hue province, Vietnam

“…The 13 C NMR of 6 exhibited thirty carbon signals presenting for a carboxylic triterpene: a carboxylic acid group at δC 178.52 (C-18), two olefinic carbons at δC 139.26 (C-13) and 129.80 (C-12), two oxygenated methine groups at δC 80.18 (C-3) and 68.96 (C-6), an oxygenated quaternary carbon at δC 73.66 (C- 19), four methines at δC 57.24 (C-5), 55. 15 The NMR and MS spectral data of 6 were in agreement with uncaric acid. [2] This compound was obtained firstly from Uncaria elliptica.…”

“…The (+)-ESI-MS spectra showed a molecular ion peak at m/z 654.1 [M-COCH3+H2O+H] + . By analysis the spectroscopic data and the comparison with the literature, [15] Compound 8 was an acetylated product purified from the fruits extract as amorphous powder. The mass spectra exhibited a molecular peak at m/z 762.2 [M+H2O].…”