Sugar fatty acid esters (SFAEs) are non-ionic surfactants that are characterized by excellent surface and interfacial tension reduction capability, low toxicity, and biodegradability. These features make SFAEs extremely promising for industrial applications as emulsifiers in the cosmetic and food sectors.[1] Interestingly, SFAEs can be obtained from renewable resources (from industrial waste and biomass) by enzymatic and/or chemoenzymatic approaches, thus answering the need for evermore sustainable and circular chemistry.[2,3] 6-O-Lauroyl-, 6-O-palmitoyl- and 6-O-stearoyl-1-O-butyl glucopyranosides were enzymatically synthesized by reacting n-butyl glucoside with molten fatty acids in an easily scalable solvent-free system. Derivatization of glucose as an alkyl glucoside before the esterification reaction played a key role to circumvent the striking different solubility of glucose and fatty acids. The physico-chemical properties of these tensides, such as interfacial tension features, W/O emulsification capability and W/O stability over time were deeply investigated.[4] References 1. N.S. Neta, J.A. Teixeira, L.R. Rodrigues, Crit. Rev. Food Sci. Nutr. 2015, 5, 595. 2. A.R. Alcántara, P. Domínguez de María, J.A. Littlechild, M. Schürmann, R.A. Sheldon, R. Wohlgemuth, ChemSusChem 2022, e202102709. 3. T. Keijer, Nat. Chem. 2019, 11, 190. 4. S. Sangiorgio, E. Pargoletti, M. Rabuffetti, M.S. Robescu, R. Semproli, D. Ubiali, G. Cappelletti, G. Speranza, under review This work was financially supported by Cariplo Foundation (Italy) (call: “Circular Economy for a sustainable future 2020”, project BioSurf, ID 2020-1094).

Chemoenzymatic Synthesis of Alkyl Glycoside Fatty Acid Esters and Investigation of their Emulsifying Properties / S. Sangiorgio, E. Pargoletti, M. Rabuffetti, S. Nasserian, M.S. Robescu, R. Semproli, D. Ubiali, G. Cappelletti, G. Speranza. ((Intervento presentato al 46. convegno A. Corbella International Summer School on Organic Synthesis (ISOS 2022) tenutosi a Gargnano nel 2022.

Chemoenzymatic Synthesis of Alkyl Glycoside Fatty Acid Esters and Investigation of their Emulsifying Properties

S. Sangiorgio;E. Pargoletti;M. Rabuffetti;G. Cappelletti;G. Speranza
2022

Abstract

Sugar fatty acid esters (SFAEs) are non-ionic surfactants that are characterized by excellent surface and interfacial tension reduction capability, low toxicity, and biodegradability. These features make SFAEs extremely promising for industrial applications as emulsifiers in the cosmetic and food sectors.[1] Interestingly, SFAEs can be obtained from renewable resources (from industrial waste and biomass) by enzymatic and/or chemoenzymatic approaches, thus answering the need for evermore sustainable and circular chemistry.[2,3] 6-O-Lauroyl-, 6-O-palmitoyl- and 6-O-stearoyl-1-O-butyl glucopyranosides were enzymatically synthesized by reacting n-butyl glucoside with molten fatty acids in an easily scalable solvent-free system. Derivatization of glucose as an alkyl glucoside before the esterification reaction played a key role to circumvent the striking different solubility of glucose and fatty acids. The physico-chemical properties of these tensides, such as interfacial tension features, W/O emulsification capability and W/O stability over time were deeply investigated.[4] References 1. N.S. Neta, J.A. Teixeira, L.R. Rodrigues, Crit. Rev. Food Sci. Nutr. 2015, 5, 595. 2. A.R. Alcántara, P. Domínguez de María, J.A. Littlechild, M. Schürmann, R.A. Sheldon, R. Wohlgemuth, ChemSusChem 2022, e202102709. 3. T. Keijer, Nat. Chem. 2019, 11, 190. 4. S. Sangiorgio, E. Pargoletti, M. Rabuffetti, M.S. Robescu, R. Semproli, D. Ubiali, G. Cappelletti, G. Speranza, under review This work was financially supported by Cariplo Foundation (Italy) (call: “Circular Economy for a sustainable future 2020”, project BioSurf, ID 2020-1094).
12-giu-2022
Settore CHIM/06 - Chimica Organica
Settore CHIM/02 - Chimica Fisica
Chemoenzymatic Synthesis of Alkyl Glycoside Fatty Acid Esters and Investigation of their Emulsifying Properties / S. Sangiorgio, E. Pargoletti, M. Rabuffetti, S. Nasserian, M.S. Robescu, R. Semproli, D. Ubiali, G. Cappelletti, G. Speranza. ((Intervento presentato al 46. convegno A. Corbella International Summer School on Organic Synthesis (ISOS 2022) tenutosi a Gargnano nel 2022.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/940431
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