Organogels from Double-Chained Vitamin C Amphiphilic Derivatives.
The syntheses and physicochemical characterization of double-chained amphiphilic compounds obtained from vitamin C are reported: dialkanoyl-5,6-O-ascorbic acid esters (Di-ASCn, n=8, 10, and 12). The acetyl-5-dodecanoyl-6-ascorbic acid ester is synthesized and investigated for comparison. These products are quite insoluble in water and in polar solvents, although they form homogeneous dispersions in cyclohexane. Upon cooling, these dispersions turn into a gel-like phase. Differential scanning calorimetry, FTIR spectroscopy, and small- and wide-angle X-ray scattering experiments are performed to investigate the properties of pure solids and their liquid dispersions. Di-ASCn retain the same redox properties of the parent molecule and represent a valid candidate for the production of nanosized protective carriers for valuable guests that are sensitive to oxidative radical attack. Moreover, the contribution of the vitamin C hydroxyl group in position 5 to the overall hydration properties of single- and double-chained amphiphilic derivatives is discussed.
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Elia
E
Tempestini
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Martina
M
Bucci
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Vincenzo
V
Mastromartino
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Marianna
M
Gori
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Damiano
D
Tanini
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Moira
M
Ambrosi
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Emiliano
E
Fratini
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.
Antonella
A
Capperucci
Department of Chemistry, University of Florence, Via della Lastruccia 3-13, 50019, Sesto Fiorentino, Italy.|Enzo Ferroni Foundation, Via della Lastruccia 3, 50019, Sesto Fiorentino, Italy.
Pierandrea
http://orcid.org/0000-0003-4647-0369
P
Lo Nostro
D001205:Ascorbic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005782:Gels / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013501:Surface-Active Agents / Q000737:chemistry*
D004952:Esters; D005782:Gels; D013501:Surface-Active Agents; D001205:Ascorbic Acid
amphiphiles; gels; hydrogen bonds; polymorphism; surfactants