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Organogels from Double‐Chained Vitamin C Amphiphilic Derivatives
Author(s) -
Tempestini Elia,
Bucci Martina,
Mastromartino Vincenzo,
Gori Marianna,
Tanini Damiano,
Ambrosi Moira,
Fratini Emiliano,
Capperucci Antonella,
Lo Nostro Pierandrea
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201601267
Subject(s) - ascorbic acid , differential scanning calorimetry , chemistry , amphiphile , cyclohexane , organic chemistry , copolymer , polymer , thermodynamics , physics , food science
The syntheses and physicochemical characterization of double‐chained amphiphilic compounds obtained from vitamin C are reported: dialkanoyl‐5,6‐ O ‐ascorbic acid esters (Di‐ASC n , 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‐ASC n 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.