Impact of the chemical structure on amphiphilic properties of sugar-based surfactants: A literature overview

Gaudin, Théophile; Lü, Heng; Fayet, Guillaume; Drelich, Audrey; Rotureau, Patricia; Pourceau, Gwladys; Wadouachi, Anne; Hecke, Elizabeth Van; Nesterenko, Alla; Pezron, Isabelle

doi:10.1016/j.cis.2019.06.003

Cited by 73 publications

(64 citation statements)

References 70 publications

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“…Thus, CXE has a strong ability to reduce the interfacial tension between water and solvents of low polarity. This result might be attributed to the hydrophobic effect 42 of the nonpolar groups in CXE. Nonpolar molecules in water tend to bury hydrophobic residues within the molecules, and nonpolar solvents can disrupt hydrophobic interactions, which makes solvents with low polarity more conducive to CXE extension at the oil–water interface.…”

Section: Resultsmentioning

confidence: 95%

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

Qiu

Chen

Wei

et al. 2020

J of Applied Polymer Sci

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An environmental friendly oil-soluble surfactant colophony xylitol ester (CXE) is first synthesized from natural colophony and xylitol with the use of hotcompressed water and subcritical CO 2 in a steel autoclave. In this solvent-free system, the conversion of the reaction was up to 90.30% in 4 h. Thermal gravimetric analysis determine that its thermal stability was as high as 310 C. CXE is effective in reducing the surface tension of six different organic solvents. The greatest effect of surface tension reduction by CXE is in the case of dimethyl sulfoxide, the surface tension of the surfactant solution was as low as 36.26 mN/m at its critical micelle concentration value of 7.49 mM; The greatest effect of interfacial tension reduction by CXE is in the case of turpentine and water, the interfacial tension low to 1.51 mN/m. Furthermore, transmission electron microscope and particle size measurement showed that CXE is successfully self-assembled into micelles, vesicles, and heteromorphic vesicles in six kinds of organic solvents. Finally, the critical micelle concentration curves at different temperatures provided the thermodynamic parameters of the aggregate formation, found that 4G 0 agg , 4H 0 agg , and 4S 0 agg are negative and increased as the temperature increased. K E Y W O R D S colophony xylitol ester, interfacial properties, micelle, thermodynamics, vesicle 1 | INTRODUCTION Colophony is a renewable natural resin consisting of a series of tricyclic diterpenoid resin acids. 1 Colophony and its products are used in welding, paper, and coatings, as well as polymer and food industries. 2,3 Modification of brittle colophony to colophony esters can produce materials with good antioxidant properties and mechanically pliable. 4 Furthermore, owing to the hydrophobic structure of the tricyclic skeleton, surfactants can be prepared by introducing hydrophilic groups into the molecules. 5 Unlike long chain fatty acids, the rigid structure of colophony can enhance the thermal, chemical, and mechanical stability of the resulting surfactants. 6 Xylitol is widely found in fruits, vegetables, cereals, mushrooms, and other plants. 7 It is also an intermediate metabolite in the human body and has good biocompatibility and biodegradability. Fatty acid xylitol esters are a class of nonionic surfactants with important physiological activities. 8,9 Some derivates have been shown to have antitumor activity 10 and plant growth inhibition. 11 Enzymatic syntheses of xylitol esters in organic solvents have been reported. 12,13

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Section: Resultsmentioning

confidence: 95%

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

Qiu

Chen

Wei

et al. 2020

J of Applied Polymer Sci

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“…Gaudin et al [56] described how that the chemical nature of a substance linked to a sugar molecule possesses an important impact on the surfactant properties. For example, surfactants with thioether linkers were found to have a lower CMC and to be less soluble than their analogues with ether linkers.…”

Section: Non-ionic Sugar Bio-based Surfactantsmentioning

confidence: 99%

Synthetic and Bio-Derived Surfactants Versus Microbial Biosurfactants in the Cosmetic Industry: An Overview

Moldes

Rincón-Fontán

López-Prieto

et al. 2021

IJMS

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This article includes an updated review of the classification, uses and side effects of surfactants for their application in the cosmetic, personal care and pharmaceutical industries. Based on their origin and composition, surfactants can be divided into three different categories: (i) synthetic surfactants; (ii) bio-based surfactants; and (iii) microbial biosurfactants. The first group is the most widespread and cost-effective. It is composed of surfactants, which are synthetically produced, using non-renewable sources, with a final structure that is different from the natural components of living cells. The second category comprises surfactants of intermediate biocompatibility, usually produced by chemical synthesis but integrating fats, sugars or amino acids obtained from renewable sources into their structure. Finally, the third group of surfactants, designated as microbial biosurfactants, are considered the most biocompatible and eco-friendly, as they are produced by living cells, mostly bacteria and yeasts, without the intermediation of organic synthesis. Based on the information included in this review it would be interesting for cosmetic, personal care and pharmaceutical industries to consider microbial biosurfactants as a group apart from surfactants, needing specific regulations, as they are less toxic and more biocompatible than chemical surfactants having formulations that are more biocompatible and greener.

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“…However, there are few studies on structural modifications based on VAA. Sucrose fatty acid esters (SEs), as representative compounds of polyols similar in structure to VAA, are widely used in the fields of food and cosmetics 14,15 . Traditional chemical synthesis methods of SEs are accompanied by a variety of esterification products 16 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a series of validoxylamine A esters and their biological activities

Kang

Zhu

et al. 2021

Pest Management Science

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BACKGROUND The worldwide reduction in food production due to pests and diseases is still an important challenge facing today. Validoxylamine A (VAA) is a natural polyhydroxyl compound derived from validamycin, acting as an efficient trehalase inhibitor with insecticidal and antifungal activities. To extend the application and discover green pesticide, a series of ester derivatives were prepared based on VAA as a lead compound. Their biological activities were investigated against three typically agricultural disease, Rhizoctonia solani, Sclerotinia sclerotiorum and Aphis craccivora. RESULTS This study involved 30 novel validoxylamine A fatty acid esters (VAFAEs) synthesized by Novozym 435 and they were characterized with high‐resolution electrospray ionization mass spectrometry (HR‐ESI‐MS) and proton nuclear magnetic resonance (1H‐NMR). Of these 30 derivatives, most compounds showed improved antifungal activity, and 12 novel compounds showed improved insecticidal activity. When reacted with pentadecanoic acid, compound 14 showed the highest inhibitory activity against R. solani [median effective concentration (EC50) 0.01 μmol L−1], while the EC50 value of VAA was 34.99 μmol L−1. Furthermore, 21 novel VAFAEs showed higher inhibitory activity against S. sclerotiorum. Validoxylamine A oleic acid ester, compound 21, exhibited the highest insecticidal activity against A. craccivora [median lethal concentration (LC50) 39.63 μmol L−1], while the LC50 value of Pymetrozine was 50.45 μmol L−1, a commercialized pesticide against A. craccivora. CONCLUSION Combining our results, esterification of VAA by introducing different acyl donors was beneficial for the development of new eco‐friendly drugs in the field of pesticides.

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Impact of the chemical structure on amphiphilic properties of sugar-based surfactants: A literature overview

Cited by 73 publications

References 70 publications

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

Synthetic and Bio-Derived Surfactants Versus Microbial Biosurfactants in the Cosmetic Industry: An Overview

Synthesis of a series of validoxylamine A esters and their biological activities

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