Oleic Acid Based Cyclodextrins for the Development of New Hydrosoluble Amphiphilic Compounds. Issue 6 (15th January 2019)

• Record Type: Journal Article
• Authors: Cocq, Aurélien; Rousseau, Cyril; Bricout, Hervé; Oliva, Estefanía; Bonnet, Véronique; Djedaïni‐Pilard, Florence; Monflier, Eric; Tilloy, Sébastien
• Is Part Of: European journal of organic chemistry. Issue 6(2019)
• Page Start: 1236
• Page End: 1241
• Publication Date: 2019-01-15
• Subjects: Cyclodextrins -- Maleic anhydride -- Maleinisation -- Oleic acid -- Succinic anhydride; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801609
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A new family of amphiphilic cyclodextrins produced from oleic acid derivatives and maleic anhydride is described. These amphiphilic cyclodextrins are synthesized in two steps. The first step is the alkenylation of maleic anhydride by oleic acid derivatives to produce the oleic succinic anhydrides. The second step is the grafting of the oleic succinic anhydrides on various cyclodextrins. A self‐inclusion of the alkyl chain or an inclusion of one alkyl chain in the cavity of another CD is showed by NMR experiments. The twelve amphiphilic cyclodextrins described possess high solubility in water (50–500 g/L at 20 °C) and low critical aggregation concentration (16–360 mg/L). Abstract : A new family of amphiphilic cyclodextrins produced from methyl oleate or oleic acid and maleic anhydride is described. A self‐inclusion of the alkyl chain or an inclusion of an alkyl chain in another CD cavity is evidenced. These oleic succinyl‐CDs possess a high solubility in water, a low surface tension, and a low critical aggregation concentration.