Solvent-Free Synthesis of High-Purity Sucrose Fatty Acid Monoesters and a Comparison of Their Properties with Those of Their Commercial Counterparts

Xie, Mengfei; White, Lorenzo V.; Banwell, Martin G.; Wang, Yong; Lan, Ping

doi:10.1021/acsfoodscitech.1c00185

Cited by 6 publications

(5 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The digestion behavior of corn oil in emulsions stabilized by S-170, S-270, S-570, S-770, S-970, S-1170, S-1570, S-1670, SSE, and Tween-80 were examined using a stimulated gastrointestinal digestion model as described previously with minor modifications [ 23 ]. Firstly, a 20 mL emulsion aliquot was mixed with an equal volume of prepared artificial saliva working solution containing 15 mg/mL porcine gastric mucin (type II) and incubated at 37 °C for 2 min.…”

Section: Methodsmentioning

confidence: 99%

Sucrose Stearates Stabilized Oil-in-Water Emulsions: Gastrointestinal Fate, Cell Cytotoxicity and Proinflammatory Effects after Simulated Gastrointestinal Digestion

Zheng,

Guan,

Chen

et al. 2024

Foods

View full text Add to dashboard Cite

Different structural composition ratios of sucrose stearates with hydrophilic–hydrophobic balance (HLB) values ranging from 1 to 16 on lipolysis in emulsion were investigated using a simulated gastrointestinal tract (GIT). Results showed a direct correlation between the HLB values of sucrose stearates and the lipolysis rate of emulsions, and a lower HLB value led to diminished lipolysis in the GIT simulation model. Mechanism study indicated that poor emulsifying capacity of sucrose stearates and lipolysis of sucrose stearates with lower HLB value inhibited the digestive behavior of oil. In addition, monoester was mainly hydrolyzed in the gastric phase, whereas sucrose polyesters caused lipolysis in the intestinal phase using an in vitro digestive model and HPLC analysis, further suppressing lipid digestion. Furthermore, a decrease in cell cytotoxicity and proinflammatory effects on Caco-2 and Raw264.7 were observed post-digestion, respectively. This work offers important insights into the effects of the degree of esterification of sucrose stearate on lipid digestion behavior in oil-in-water emulsions.

show abstract

Section: Methodsmentioning

confidence: 99%

Sucrose Stearates Stabilized Oil-in-Water Emulsions: Gastrointestinal Fate, Cell Cytotoxicity and Proinflammatory Effects after Simulated Gastrointestinal Digestion

Zheng,

Guan,

Chen

et al. 2024

Foods

View full text Add to dashboard Cite

show abstract

“…The in vitro digestion of sucrose ester emulsions was studied using minor modifications of a previously reported method. 12 So, a gastrointestinal behavior model (GITBM) was constructed to simulate digestion during the oral, gastric, and small intestinal phases. In these simulations, the temperature was maintained at 37 °C.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Investigation of the Emulsifying and In Vitro Digestive Properties of High-Purity Sucrose Monostearate Esters

Chen

Liang

Qing

et al. 2022

ACS Food Sci. Technol.

View full text Add to dashboard Cite

Long-chain fatty acid mono- and higher-order esters of sucrose are important chemicals, often produced at kilotonne scales, due to their wide range of commercial applications, including as food emulsifiers. While the monoester content of commercial sucrose stearate ester products range up to 75% (in S-1670), this can be further increased to >99% when enzymatic techniques are deployed for product preparation. Although the emulsifying properties of sucrose stearate ester-containing products (such as S-1670) are well-defined, formulations with monoester contents greater than 75% have never been prepared and evaluated. In this study, three sucrose stearate samples with an 80, 85, or 90% monoester content (samples 1–3, respectively) were prepared and the influence of these on their digestive, emulsifying, and rheological properties was studied. The results show that emulsions stabilized by S-1670 (75%) and sample 1 (80%) exhibited the best digestive behavior in a gastrointestinal behavior model, recording 69 and 78% free fatty acid release, respectively. Counterintuitively, an inverted V-shaped profile was observed when the monoester content, which ranged from 75–99%, was plotted as a function of emulsifying properties. These results should serve as an important guide for the development of new sucrose ester products in the food industry.

show abstract

“…This approach required a high temperature with the use of methyl stearate/potassium stearate and K2CO3/KOH as the base catalyst. The final sucrose ester mixtures contain a monoester fraction in the range of 41-75% [38]. Concerning With regard to the chemical esterification, the regioselective production of SEs in one step is challenging due to the presence of eight different hydroxyl groups.…”

Section: Synthesis Of 6-o-sucrose Estersmentioning

confidence: 99%

Sugar-Based Monoester Surfactants: Synthetic Methodologies, Properties, and Biological Activities

Verboni,

Perinelli,

Buono

et al. 2023

Antibiotics

View full text Add to dashboard Cite

Glycolipids are biocompatible and biodegradable amphiphilic compounds characterized by a great scientific interest for their potential applications in various technological areas, including pharmaceuticals, cosmetics, agriculture, and food production. This report summarizes the available synthetic methodologies, physicochemical properties, and biological activity of sugar fatty acid ester surfactants, with a particular focus on 6-O-glucose, 6-O-mannose, 6-O-sucrose, and 6′-O-lactose ones. In detail, the synthetic approaches to this class of compounds, such as enzymatic lipase-catalyzed and traditional chemical (e.g., acyl chloride, Steglich, Mitsunobu) esterifications, are reported. Moreover, aspects related to the surface activity of these amphiphiles, such as their ability to decrease surface tension, critical micelle concentration, and emulsifying and foaming ability, are described. Biological applications with a focus on the permeability-enhancing effect across the skin or mucosa, antimicrobial and antifungal activities, as well as antibiofilm properties, are also presented. The information reported here on sugar-based ester surfactants is helpful to broaden the interest and the possible innovative applications of this class of amphiphiles in different technological fields in the future.

show abstract

Solvent-Free Synthesis of High-Purity Sucrose Fatty Acid Monoesters and a Comparison of Their Properties with Those of Their Commercial Counterparts

Cited by 6 publications

References 43 publications

Sucrose Stearates Stabilized Oil-in-Water Emulsions: Gastrointestinal Fate, Cell Cytotoxicity and Proinflammatory Effects after Simulated Gastrointestinal Digestion

Sucrose Stearates Stabilized Oil-in-Water Emulsions: Gastrointestinal Fate, Cell Cytotoxicity and Proinflammatory Effects after Simulated Gastrointestinal Digestion

Investigation of the Emulsifying and In Vitro Digestive Properties of High-Purity Sucrose Monostearate Esters

Sugar-Based Monoester Surfactants: Synthetic Methodologies, Properties, and Biological Activities

Contact Info

Product

Resources

About