Carbohydrate-Based Surfactants: Structure-Activity Relationships

Razafindralambo, Hary; Blecker, Christophe; Paquot, Michel

doi:10.5772/34971

Cited by 11 publications

(13 citation statements)

References 26 publications

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“…The effect described therein and works cited is due to increased hydrophobicity of the tail length, which significantly affects their CMC. The same impact of the alkyl chain length on the CMC value was observed also for other sugar-based surfactants such as urinate and uronoamide derivatives of dodecyl glucuronolactones [26], gluconamide-type surfactants [12,13] and sucrose monoesters [6].…”

Section: Methodssupporting

confidence: 61%

Synthesis, Surface and Antimicrobial Activity of New Lactose-Based Surfactants

et al. 2019

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This work presents a synthesis method for new surfactants based on lactose. The compounds obtained belong to the homologous series of O-β-D-Galactopyranosyl-(1→4)-N-alkyl-(3-sulfopropyl)-D-glucosamine hydrochloride, containing 12 and 14 carbon atoms in the alkyl chain, and they may serve as an example of cationic surfactants. The newly synthesized compounds exhibit good surface properties, low value of CMC (Critical Micelle Concentration) and good wetting properties. These surfactants’ ability to produce foam is considerably higher than in the commercial surfactants. Moreover, antibacterial and fungistatic activity was carried out by well diffusion assay against the selected bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa), yeasts (Candida albicans) and filamentous fungi (Fusarium graminearum, F. avenaceum, F. oxysporum, F. culmorum, F. equiseti, Alternaria alternata and Botrytis cinerea). It was shown that the resulting quaternary salts significantly inhibit the growth of tested microorganisms. Antibacterial and fungistatic activity of the surfactant compounds varied depending on the species of bacteria or fungi. The results of antimicrobial activity of new lactose derivatives indicate that the compounds exhibit larger or similar antagonistic activity against tested bacteria and fungi than typical cationic surfactant cetylpyridinium chloride.

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Section: Methodssupporting

confidence: 61%

Synthesis, Surface and Antimicrobial Activity of New Lactose-Based Surfactants

et al. 2019

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“…Interaction of pyd-glc with tween-20. 34 The change in the micro-environment from pre-micellar state to post-micellar state has been monitored by the py value of pyd-glc. 35 This type of carbohydrate based surfactants has one sugar moiety along with lipid chain; as a result they undergo micellization like other surfactants.…”

Section: Interaction Of Pyd-glc With β-Cdmentioning

confidence: 99%

“…In fact, in recent years efforts have been made to introduce transition metal based complexes with high lifetime to overcome the background fluorescence of biological samples. 34 Due to its non-toxicity it has its wide applications in drug, food, scientific research etc. β-CD is a doughnut shaped cyclic oligosaccharide having cavity diameter 6.2 Å and length 8.0 Å.…”

mentioning

confidence: 99%

Synthesis and evaluation of a glucose attached pyrene, as a fluorescent molecular probe in sugar and non-sugar based micro-heterogeneous media

et al. 2015

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A new fluorescent pyrene-glucose conjugate (pyd-glc), 1-(4,6-O-butylidene-β-dglucopyranosyl)-4-(1-pyrene)-butan-2-one, has been synthesized by attaching pyrene molecule with acetal (butylidene) protected glucose via butane-2-one linker. Detailed photo-physical studies of pyd-glc in homogeneous media have been carried out in both protic and aprotic solvents which lead to a py scale, a solvent polarity scale specific to this molecule, like that of pyrene. The molecule aggregates in water and partitions as a monomer in micro-heterogeneous media. The photo-physical response of pyd-glc has been studied in various sugar and non-sugar based micro-heterogeneous media. Similar to pyrene, this molecule offers multiple fluorescence parameters to investigate the organization of micro-heterogeneous media. The fluorescence parameters of pyd-glc faithfully reflect the state of organization of these anisotropic media.

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“…Finding alternatives for the hydrophilic moiety is therefore an important issue, and carbohydrates, arising from renewable crops, and owing to their polyhydroxylated structure, appear as ideal candidates. Since fats (for the hydrophobic moiety) are also abundantly available from renewable resources, the combination of fats with carbohydrates is a straightforward way to synthesize 100% bio-based surfactants [4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…The purpose of this chapter is to share the vision of carbohydrate chemists on synthetic carbohydrate-based surfactant (CBS) and to illustrate the diversity of molecular structures which can be found in this family; as a complement to important reviews, books and chapters published throughout the past decades [4][5][6][7][8][9][10]32,33]. The focus is made on the structural aspects and synthetic aspects, and giving basic information or referring to the relevant literature with respect to their physicochemical properties and applications.…”

Section: Introductionmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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Carbohydrate-Based Surfactants: Structure-Activity Relationships

Cited by 11 publications

References 26 publications

Synthesis, Surface and Antimicrobial Activity of New Lactose-Based Surfactants

Synthesis, Surface and Antimicrobial Activity of New Lactose-Based Surfactants

Synthesis and evaluation of a glucose attached pyrene, as a fluorescent molecular probe in sugar and non-sugar based micro-heterogeneous media

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

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