title: New multifunctional surfactants from natural phenolic acids.
abstract: Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.
authors.affiliation: Dipartimento Farmaco Chimico Tecnologico, University of Siena, Via Aldo Moro, 53100 Siena, Italy.
authors.forename: Marisanna
authors.initials: M
authors.lastname: Centini
authors.forename: Maria Sole
authors.initials: MS
authors.lastname: Rossato
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sega
authors.forename: Anna
authors.initials: A
authors.lastname: Buonocore
authors.forename: Sara
authors.initials: S
authors.lastname: Stefanoni
authors.forename: Cecilia
authors.initials: C
authors.lastname: Anselmi
mesh_terms: D002109:Caffeic Acids / Q000737:chemistry; D004951:Esterification; D062385:Hydroxybenzoates / Q000737:chemistry*; D015394:Molecular Structure; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002109:Caffeic Acids; D062385:Hydroxybenzoates; D013501:Surface-Active Agents; C017616:phenolic acid; C040048:caffeic acid