Selected Physicochemical and Biological Properties of Ethyl Ascorbic Acid Compared to Ascorbic Acid

• Published in: Biological & pharmaceutical bulletin Vol. 40; no. 8; pp. 1199 - 1206
• Main Authors: Golonka, Iwona, Oleksy, Monika, Junka, Adam, Matera-Witkiewicz, Agnieszka, Bartoszewicz, Marzenna, Musiał, Witold
• Format: Journal Article
• Language: English; Japanese
• Published: Japan The Pharmaceutical Society of Japan 2017; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: Acids; Activation energy; Animals; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; antimicrobial; Antimicrobial activity; Antimicrobial agents; antioxidant; Antioxidants - chemistry; Antioxidants - pharmacology; Ascorbic acid; Ascorbic Acid - analogs & derivatives; Ascorbic Acid - chemistry; Ascorbic Acid - pharmacology; Bacteria - drug effects; Bacteria - growth & development; Biological properties; Biphenyl Compounds - metabolism; Candida albicans - drug effects; Candida albicans - growth & development; Cell Line; Cell Survival - drug effects; Cytotoxicity; Differential thermal analysis; Drug Stability; Endothermic reactions; ethyl ascorbic acid; Evaluation; Exothermic reactions; Fibroblasts; Hydrogen-Ion Concentration; Kinetics; Mice; pH effects; Picrates - metabolism; Spectroscopic analysis; stability; Staphylococcus; Temperature effects; Thermal analysis; Thermal stability; Thermogravimetry; Toxicity; Vitamin C; antimicrobial; ethyl ascorbic acid; antioxidant; cytotoxicity; stability
• ISSN: 0918-6158; 1347-5215
• DOI: 10.1248/bpb.b16-00967

The aim of the work was the evaluation of selected biological and physicochemical, applicative properties of ethylated ascorbic acid (AAE) compared to ascorbic acid (AA). Thermogravimetry (TG), differential thermogravimetry (DTG), and differential thermal analysis (DTA) were conducted, followed by the evaluation of AAE decomposition by the UV-Vis spectroscopic method including the influence of temperature and pH. Scavenging, antimicrobial activity and cytotoxicity against L929 fibroblasts were also performed. The difference in mass loss between AA and AAE was 30% via TG. DTA revealed characteristic exothermic and endothermic effects. The AAE solution was more thermally stable than AA. The calculated zero-order rate constants of free-radical scavenging kinetics for AAE were in the range of 4.9×10−3–1.35×10−2 s−1. The activation energy for the process was 11,2281 kJ/mol. AAE was active against Staphylococcus (S.) aureus and Enterococcus (E.) faecalis and acted stronger against Candida (C.) albicans than AA. The concentrations of AA ≥2.5% were cytotoxic, whereas in the case of AAE, a 10% concentration was considered cytotoxic. DTG enables the detailed differentiation between AA and AAE. AAE in aqueous solution is more stable compared to AA. The antioxidant activity of AAE is significant. However, the reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH) indicates prolonged activity compared to AA. Variability in the antimicrobial activity of AAE may find practical application in the pharmaceutical and cosmetic industries. The potential for applicative aims may be supported by the relatively low in vitro toxicity of AAE.