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Oleic Acid Based Cyclodextrins for the Development of New Hydrosoluble Amphiphilic Compounds
Author(s) -
Cocq Aurélien,
Rousseau Cyril,
Bricout Hervé,
Oliva Estefanía,
Bonnet Véronique,
DjedaïniPilard Florence,
Monflier Eric,
Tilloy Sébastien
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801609
Subject(s) - succinic anhydride , amphiphile , oleic acid , chemistry , maleic anhydride , acylation , solubility , maleic acid , organic chemistry , alkyl , cyclodextrin , succinic acid , polymer chemistry , grafting , copolymer , biochemistry , catalysis , polymer
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).