Synthesis of sugar-containing surfactants based on 8-hydroxyoctanoic acid

: 28-33
Lviv Polytechnic National University
Lviv Polytechnic National University
Lviv Polytechnic National University

In the recipes of modern cosmetic, sanitary and pharmaceutical preparations, there is a large number of accessory compounds, including surface-active substances. One of the main requirements for these compounds is the efficacy, availability, lack of allergenicity, low toxicity of decomposition products and the ability to biodegradate in natural conditions. For surfactants used in the biomedical industry and pharmacy, additional requirements are put forward - biocompatibility with body tissues, bio-inertness and non-toxicity of products of their metabolism. All the more widely used surfactants, which receive modification of compounds of natural origin - amino acids, oils and saccharides. Taking into account that we have developed an effective one-reactor method for the synthesis of ω-hydroxycarboxylic acids on the basis of cyclic ketones, we decided to consider the possibility of obtaining new surface-active substances on their basis. Creation of new type of surfactants of this type is actual today as derivatives of hydroxycarboxylic acids are widely used in cosmetics and in recipes of medical preparations.

We proposed to obtain derivatives of monosaccharides and higher ω-hydroxy acids by the primary hydroxyl group of acid. The saccharide fragment in such a compound will play the role of hydrophilic, and the remainder of the carboxylic acid - a hydrophobic block. In alkaline medium, such a compound will form carboxylate ion and turn into a "Gemini"-surfactant with different nature of hydrophilic groups (non-ionic and anionic). In addition, the presence in the molecule of the carboxyl group will allow it to construct other types of reactive surfactants on its basis.

As the previouses compounds, we have selected available α-D-glucopyranose and synthesized 8-hydroxyoctanoic acid.

The preferred direction of the interaction of ω-hydroxycarboxylic acids with α-D-glucopyranose in the presence of traces of hydrochloric acid is the formation of the ether with the participation of the glycoside group of saccharide and the OH hydroxy acid group.

The structure of the compound obtained was confirmed and characterized by physicochemical constants. An isotherm of surface tension on the border air - aqueous solution for the obtained surfactant, a critical concentration of micelle formation was calculated.


1. Chemistry and Technology of Surfactants. Edited by Richard J. Farnby. - Blackwell Publishing Ltd. - 2006 - 331.
2. Dopomizhni rechovyny v tekhnolohii likiv: vplyv na tekhnolohichni, spozhyvchi, ekonomichni kharakterystyky i terapevtychnu efektyvnist: navch. posib. dlia stud. vyshch. farmats. navch. zakl. / avt.uklad.: I. M. Pertsev, D. I. Dmytriievskyi, V. D. Rybachuk ta in.; za red. I. M. Pertseva. - Kh.: Zoloti storinky, 2010. - 600 s.  
3. Basinska T. (2005) Hydrophilic core-shell microspheres: a suitable support for controlled attachment of proteins and biomedical diagnostics. Macromol Boisc - P. 1145-1168.
4. Borzenkov, M., Hevus, O. (2014) Surface Active Monomers. SpringerBriefs in Materials. -  R. 67.
5. Muthukrishnan, S., Jutz, G., André,, X., Mori, H., & Müller. (2005) Synthesis of Hyperbranched Glycopolymers via Self-Condensing Atom Transfer Radical Copolymerization of a Sugar-Carrying Acrylate. Macromolecules, 38(1), R. 9-18.
6. Cosima Stubenrauch (2001) Sugar surfactants - Aggregation, interfacial, and adsorption phenomena. Current Opinion in Colloid & Interface Science. 6(2) - R. 160-170.
7. Brycki, B. E., Kowalczyk, I. H., Szulc, A., Kaczerewska, O., & Pakiet, M. (2017) Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications. Application and Characterization of Surfactants. - R. 97-155.
8. Kamal, M. S. (2015) A Review of Gemini Surfactants: Potential Application in Enhanced Oil Recovery. Journal of Surfactants and Detergents. 19(2), 223-236.
9. B. S. Sekhon. Gemini (dimeric) surfactants The two-faced molecules. Resonance, March 2004, Vol. 9, Issue 3, P. 42-49.
10. Kornhauser, A. (2010) Applications of hydroxy acids: classification, mechanisms, and photoactivity. Clinical, Cosmetic and Investigational Dermatology. R. 135-142.
11. Green, B. A., Yu, R. J., & Van Scott, E. J. (2009) Clinical and cosmeceutical uses of hydroxyacids. Clinics in Dermatology. 27(5), R. 495-501.
12. Rodrigues L. H., Maia Campos PM. (2002) Comparative study of the effects of cosmetic formulations with or without hydroxy acids on hairless mouse epidermis by histopathologic, morphometric, and stereologic evaluation. J Cosmet Sci. 53(5). - R. 269-82.
13. Belcher R. Submicro Methods of Organic Analysis. - Elsevier. - Amsterdam. - 1966. - 346 p.
14. Borzenkov M. M. Syntez ta vlastyvosti poverkhnevo-aktyvnykh monomeriv - pokhidnykh hidroksy- ta aminokarbonovykh kyslot: dys. … kand. khim. nauk. Lviv, 2012.