Details

Autor(en) / Beteiligte

• Tempestini, Elia
• Bucci, Martina
• Mastromartino, Vincenzo
• Gori, Marianna
• Tanini, Damiano
• Ambrosi, Moira
• Fratini, Emiliano
• Capperucci, Antonella
• Lo Nostro, Pierandrea

Titel

Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives

Ist Teil von

• Chemphyschem, 2017-05, Vol.18 (10), p.1400-1406

Ort / Verlag

Germany

Erscheinungsjahr

2017

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• 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. Surfactant stacks: Lamellar discs are observed in organogels obtained from double‐chained vitamin C surfactants. The figure depicts the sequence of hydrophobic (yellow) and hydrophilic (blue) layers, as determined by small‐angle X‐ray scattering analysis.