Chromatographic separations of sucrose monostearate structural isomers

Torres, Mercè; Dean, Maria A.; Wagner, Fred

doi:10.1016/0021-9673(90)85194-z

Cited by 15 publications

(3 citation statements)

References 12 publications

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“…The synthesized esters were methyl 2-O-acyl-a-D-glucopyranoides (25)(26)(27) and azido 2-O-acyl-a-D-glucuronic acids (28-30) as shown in Figure 1. The yields of corresponding esters are listed in Table 1.…”

Section: -24mentioning

confidence: 99%

Selective Synthesis of Glycoside Fatty Acid Esters and Their Antibacterial Structure‐activity Relationship against Bacterial Staphylococcus Aureus and Salmonella Agona

Lou

Cassidy²

2015

J Chinese Chemical Soc

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Fatty acid esters of glycosides and glucopyranosiduronides were regioselectively synthesized with tin-mediated method using dibutyltin dimethoxide as the stannylating agent, these novel esters were investigated for their antibacterial activities against bacterial Staphylococcus Aureus and Salmonella Agona, the essential structural feature as antibacterial agents was probed. Antimicrobial tests showed that some laurates of trans-ol glycosides are effective inhibitors against S. Aureus, while some laurates and myristates of cis-ol glycosides are moderate inhibitors against both S. Aureus and S. Agona. Studies on antimicrobial structure-activity relationship of sugar fatty acid esters showed that both the carbohydrate moiety and the length of fatty acid played a vital role on the antibacterial effect.

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Section: -24mentioning

confidence: 99%

Selective Synthesis of Glycoside Fatty Acid Esters and Their Antibacterial Structure‐activity Relationship against Bacterial Staphylococcus Aureus and Salmonella Agona

Lou

Cassidy²

2015

J Chinese Chemical Soc

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“…While the production of sucrose esters has been explored for over a century, 84 selectivity in the synthesis of these esters remains a challenge; 255 distinct possible isomers with varying degrees of substitution can be obtained from acylation with a single FA. 85 Perhaps as a result of these challenges the market for sucrose esters remains modest, with an estimated production of o10 000 t/a. 70 Early syntheses of sucrose esters used FA chlorides and anhydrides to achieve acylation, however these methods gave way to direct condensation with FAs or TGs in either polar solvents, emulsion systems, or solvent-free systems.…”

Section: Glycerolmentioning

confidence: 99%

Derivation and synthesis of renewable surfactants

et al. 2012

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This critical review focuses on the origins and preparation of bio-based surfactants, defined here as non-soap, amphiphilic molecules in which the carbon atoms are derived from annually renewable feedstocks. Environmental concerns and market pressures have led to greater relevance of these chemicals in commercial applications in recent years and extensive research has gone into exploring new classes of surfactants. Highlighted here are examples of bio-based surfactants that are produced on an industrial scale and/or are based on abundant starting materials. The trend of increasing use of renewable resources as starting materials for surfactants is introduced, followed by extensive discussion of the major classes of bio-derived hydrophobes and hydrophiles. Also discussed is the status of research and development with regard to biosynthetically produced surfactants. Finally, concluding remarks address the potential for new surfactant molecular structures as a result of ongoing development in the chemistry of biorefineries, i.e., that the transformation of lignocellulose into fuels is likely to support the manufacturing of new bio-based coproducts (238 references).

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“…[7][8][9] Gas chromatography has been used to analyze SEs a er derivatization by silylation. 10,11) e most common method for separating SEs is reversed-phase high-performance liquid chromatography (RP-HPLC) with a refractive index detector (RID), [12][13][14] evaporative light scattering detector (ELSD), 15,16) or charged aerosol detector (CAD) 17) ; RP-HPLC has also been used in tandem with mass spectrometry (MS). 15,16) However, these methods are time-consuming and are restricted to the separation of mono-and di-esters but not higher analogs.…”

Section: Introductionmentioning

confidence: 99%

High-Throughput Analysis of Sucrose Fatty Acid Esters by Supercritical Fluid Chromatography/Tandem Mass Spectrometry

et al. 2014

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Supercritical uid chromatography (SFC) coupled with triple quadrupole mass spectrometry was applied to the pro ling of sucrose fatty acid esters (SEs). e SFC conditions (column and modi er gradient) were optimized for the e ective separation of SEs. In the column test, a silica gel reversed-phase column was selected. en, the method was used for the detailed characterization of commercial SEs and the successful analysis of SEs containing di erent fatty acids. e present method allowed for fast and high-resolution separation of monoesters to tetra-esters within a shorter time (15 min) as compared to the conventional high-performance liquid chromatography. e applicability of our method for the analysis of SEs was thus demonstrated.Please cite this article as: K. Hori, et al

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Chromatographic separations of sucrose monostearate structural isomers

Cited by 15 publications

References 12 publications

Selective Synthesis of Glycoside Fatty Acid Esters and Their Antibacterial Structure‐activity Relationship against Bacterial Staphylococcus Aureus and Salmonella Agona

Selective Synthesis of Glycoside Fatty Acid Esters and Their Antibacterial Structure‐activity Relationship against Bacterial Staphylococcus Aureus and Salmonella Agona

Derivation and synthesis of renewable surfactants

High-Throughput Analysis of Sucrose Fatty Acid Esters by Supercritical Fluid Chromatography/Tandem Mass Spectrometry

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