24516-45-8Relevant academic research and scientific papers
Improved synthesis of sucrose fatty acid monoesters under ultrasonic irradiation
Huang, Dan,Jiang, Xue,Zhu, Hao,Fu, Xiaorong,Zhong, Kangrong,Gao, Weidong
experimental part, p. 352 - 355 (2010/12/25)
Sucrose fatty acid esters were synthesized by the transesterification of sucrose with aliphatic esters under ultrasound irradiation in good yield (≥73%). The optimum reaction conditions for the transesterification reaction include a molar ratio of sucrose to fatty acid ethyl ester of 2:1 and the use of a 13% mol anhydrous K2CO3 catalyst. The optimum reaction temperature was set at 70 °C, the optimum reaction time was 2 h, and the optimum reaction pressure was 11 kPa. The reaction had excellent monoester selectivity. The proportion of monoester (6-monoester + 6′-monoester) in the purified products was up to 92-95% via flash column chromatography over silica gel, the ratios of 6-monoester/6′-monoester are 2.1-2.7, and the sucrose monoesters were identified by HPLC-MS, NMR and IR.
Shape dependence in the formation of condensed phases exhibited by disubstituted sucrose esters
Molinier, Valerie,Kouwer, Paul J. J.,Fitremann, Juliette,Bouchu, Alain,Mackenzie, Grahame,Queneau, Yves,Goodby, John W.
, p. 1763 - 1775 (2008/02/04)
We report on the self-organizing properties of sucrose esters that are di-(1′,6′, 1′,6, and 6,6′)-substituted with aliphatic chains of identical or different chain lengths and levels of saturation. For the materials possessing two saturated aliphatic chains, the compounds exhibited thermotropic lamellar smectic A phases. A remarkable new phase transition was observed for the di-octadecanoyl homologue in which one smectic A phase transformed into another with a continuous change in layer spacing, but with a discontinuous change in the correlation length. The incorporation of long cis-unsaturated chains led to increased cross-sectional areas of the chains relative to the sucrose head groups and, hence, columnar phases were observed.
Self-organizing properties of monosubstituted sucrose fatty acid esters: The effects of chain length and unsaturation
Molinier, Valerie,Kouwer, Paul J. J.,Fitremann, Juliette,Bouchu, Alain,Mackenzie, Grahame,Queneau, Yves,Goodby, John W.
, p. 3547 - 3557 (2008/02/04)
Three families of mono-substituted sucrose fatty acid esters were prepared by enzymatic and classical synthetic procedures, and their self-assembly and self-organizational properties were investigated by thermal polarised light microscopy, differential scanning calorimetry and X-ray diffraction. The properties were evaluated as a function of the fatty acid chain length. For the lower homologues of the series columnar liquid-crystalline stacking structures were found, whereas for the higher homologues, lamellar phases predominated. A model for the columnar stacking arrangement, consisting of a unique arrangement of the molecules which could lead to the creation of multiple internal ion channels between the hydrophobic interior and the hydrophilic exterior of the columns, is suggested.
Sucrose esterification under Mitsunobu conditions: Evidence for the formation of 6-O-acyl-3′,6′-anhydrosucrose besides mono and diesters of fatty acids
Molinier, Valerie,Fitremann, Juliette,Bouchu, Alain,Queneau, Yves
, p. 1753 - 1762 (2007/10/03)
A series of sucrose monoesters and homogeneous or mixed diesters, which have various chain lengths and saturation levels, were prepared under Mitsunobu conditions with good regioselectivity. Among the anhydro derivatives arising from competitive intramolecular etherification, 3′,6′-anhydrosucrose 6-O-monoesters, which have never been reported, were identified.
Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters
Sarney, Douglas B.,Barnard, Mark J.,MacManus, David A.,Vulfson, Evgeny N.
, p. 1481 - 1487 (2007/10/03)
A regioselective synthesis of 6′-O-acyl sucrose monoesters has been developed through the lipase-catalyzed esterification of sucrose acetals with fatty acids in both organic solvents and under solvent-free conditions. The products were obtained in overall yields of 20-27% after hydrolysis of the isopropylidene groups with aqueous acids. The strict selectivity of the enzymes used also enabled the preparation of a monoester fraction that was highly enriched in 6-O-acyl sucrose. This was accomplished by lipase-catalyzed transesterification of sucrose monoesters, prepared by conventional chemical methods, in propan-2-ol. After removal of the transesterification products (sucrose and fatty acid isopropyl esters) and column chromatography on silica gel, the obtained monoester product contained 80% of the single regioisomer, 6-O-acyl sucrose.
