Evaluation of the surfactant properties of ascorbyl palmitate sodium salt.
In this paper we report on the physicochemical surface properties of ascorbyl palmitate (Asc16) and of its sodium salt (Asc16Na) with a view to their use as surfactants. Asc16Na was synthesized from ascorbyl palmitate by neutralizing the -OH groups in position 3 of the ascorbyl ring. The acid-base properties, thermal analysis and stability of Asc16Na monomers were determined. Self-assembling parameters of micellar aggregates in aqueous dispersions through critical micellar concentration (CMC) and critical micellar temperature (CMT) were measured. Asc16Na micellar dispersions efficiently solubilize poorly soluble drugs such as phenacetin and griseofulvin, and enhance their apparent solubility in aqueous environments. Stability tests showed that Asc16Na is more unstable than ascorbyl palmitate. Ascorbyl palmitate and its sodium salt are insoluble at room temperature in water, but their solubilities strongly depend on temperature, and largely increase above the CMT. Although Asc16Na is insoluble at room temperature, it is more soluble than Asc16, and its CMT significantly lowers in the undissociated acidic form. The apparent solubilities of phenacetin and griseofulvin are increased in Asc16Na aqueous solutions. The Asc16Na potential use as surfactant is restricted by its low stability in water, therefore the addition of some antioxidant species is necessary.
Palma
Santiago
S
Departamento de Farmacia, Fac. de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria-5000, Córdoba, Argentina.
Lo Nostro
Pierandrea
P
Manzo
Ruben
R
Allemandi
Daniel
D
D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D055598:Chemical Phenomena; D002626:Chemistry, Pharmaceutical; D002627:Chemistry, Physical; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D008823:Micelles; D012995:Solubility; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors; D014867:Water
D008823:Micelles; D013501:Surface-Active Agents; D014867:Water; D001205:Ascorbic Acid; C031226:6-O-palmitoylascorbic acid