Synthesis and Characterization of a Series of Novel Monoacylated Ascorbic Acid Derivatives, 6-O-Acyl-2-O-α-d-glucopyranosyl-l-ascorbic Acids, as Skin Antioxidants

Abstract

A series of novel monoacylated vitamin C derivatives were chemically synthesized with a stable ascorbate derivative, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G), and acid anhydrides in pyridine. Their solubility in organic phase, thermal stability, radical scavenging activity, and in vitro skin permeability was evaluated. These monoacylated derivatives were identified as 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) by UV spectra, elemental analyses, and nuclear magnetic resonance spectroscopy. The reactions afforded 6-Acyl-AA-2G in high yields (30-60%). 6-Acyl-AA-2G exhibited satisfactory stability in neutral solution comparable to that of a typical stable derivative, AA-2G, and also showed the radical scavenging activity. The lipid solubility of 6-Acyl-AA-2G was increased with increasing length of their acyl group. Increased skin permeability was superior to those of AA-2G and ascorbic acid (AsA). 6-Acyl-AA-2G that is susceptible to enzymatic hydrolysis by tissue esterase and/or alpha-glucosidase produces AA-2G and AsA, which is in the skin tissues. Thus, these findings indicate that the novel vitamin C derivatives presented here, 6-Acyl-AA-2G, may be effective antioxidants in skin care and medicinal use.

Enhancement of skin permeation of vitamin C using vibrating microneedles

“…[12][13][14] L-Ascorbic acid (vitamin C), a representative water-soluble vitamin, has a variety of biological, pharmaceutical and dermatological functions; it promotes collagen biosynthesis, provides photoprotection, causes melanin reduction, scavenges free radicals, and enhances the immunity (antiviral effect). [15][16][17][18][19] These properties are closely related to the well-known antioxidant properties of this compound. However, the transdermal permeability of vitamin C is low.…”

“…Therefore, the application of vitamin C in various fields of cosmetics, dermatologicals, or pharmaceuticals are limited despite its benefits. [17,[22][23][24][25] Additionally, to exploit the TDDS more efficiently scientists have worked on some combinational approaches for manufacturing TDDS by iontophoresis, electroporation, ultrasound, and pressure waves, which subsequently reported the synergistic effect of TDDS. [26] In this study, vibrating microneedles de-…”

Protease-Catalyzed Monoacylation of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid in Three Solvent Systems

“…1) by its 1 H-NMR spectrum and mass spectrum and by comparing the 1 H-NMR spectrum with that in our previous report. 8) In conclusion, we succeeded in synthesizing 6-sDode-AA-2G from AA-2G and vinyl laurate with a protease in 30% DMF/dioxane with a low water content. The addition of 3% (v/v) water to DMF/dioxane dramatically enhanced the 6-sDode-AA-2G synthesis.…”

“…1). 8,9) 6-sDode-AA-2G had outstanding permeability in a human living skin equivalent model. The AA derivative was susceptible to enzymatic hydrolysis by tissue esterase and -glucosidase to produce AA.…”

Synthesis, Characterization, and Anti-microbial Study of Polycyclicacetal Metal Complexes Derived from PEG and (Erythro-Ascorbic Acid) Derivative

“…L-ascorbic acid (LAA; i.e., vitamin C, a water soluble vitamin) contains a variety of biological, pharmaceutical and dermatological functions; for example, it can promote collagen biosynthesis, provide photoprotection, scavenge free radical, cause melaninreduction and enhances the immunity (e.g., anti-viral effect) [7]- [9]. From the perspective in biochemistry, these functions are closely related to the so-calledantioxidant properties of this compound.…”