Abstract
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.
Highlights
In the last few years there has been increased interest in work focused on synthesis and properties of new surfactants based on natural products
The reasons for choosing natural raw materials are: [5] renewable substrates—derived from continuous ecological cycles; [6] low cost of substrates—generally they are easy to obtain in nature, i.e. sucrose, lactose, glucose; [7] low toxicity and high biodegradability—the starting material come from nature microorganisms adapted to their degradation can be found in the environment; [8] variety of products—surfactants have very broad range of structural diversities, i.e. sugars may be connected to the hydrophobic tail at any of their hydroxyl groups and by different types or connecting linkages
The results showed that tested surfactant with an alkyl chain length of 12 carbon atoms demonstrated the highest efficiency, while antimicrobial activity of surfactant containing 10 carbon atoms was the worst
Summary
In the last few years there has been increased interest in work focused on synthesis and properties of new surfactants based on natural products. Literature present some examples of that type of surfactants based on sugars, sterols or fatty acids [1,2,3,4]. The reasons for choosing natural raw materials are: [5] renewable substrates (starting materials)—derived from continuous ecological cycles; [6] low cost of substrates—generally they are easy to obtain in nature, i.e. sucrose, lactose, glucose; [7] low toxicity and high biodegradability—the starting material come from nature microorganisms adapted to their degradation can be found in the environment; [8] variety of products—surfactants have very broad range of structural diversities, i.e. sugars (monosacharides, disacharides, etc.) may be connected to the hydrophobic tail at any of their hydroxyl groups and by different types or connecting linkages. Some of them are Molecules 2019, 24, 4010; doi:10.3390/molecules24214010 www.mdpi.com/journal/molecules
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