Ferulic Acid-Based Polymers with Glycol Functionality as a Versatile Platform for Topical Applications

Abstract

Ferulic acid-based polymers with aliphatic linkages have been previously synthesized via solution polymerization methods, yet they feature relatively slow ferulic acid release rates (∼11 months to 100% completion). To achieve a more rapid release rate as required in skin care formulations, ferulic acid-based polymers with ethylene glycol linkers were prepared to increase hydrophilicity and, in turn, increase ferulic acid release rates. The polymers were characterized using nuclear magnetic resonance and Fourier transform infrared spectroscopies to confirm chemical composition. The molecular weights, thermal properties (e.g., glass transition temperature), and contact angles were also obtained and the polymers compared. Polymer glass transition temperature was observed to decrease with increasing linker molecule length, whereas increasing oxygen content decreased polymer contact angle. The polymers' chemical structures and physical properties were shown to influence ferulic acid release rates and antioxidant activity. In all polymers, ferulic acid release was achieved with no bioactive decomposition. These polymers demonstrate the ability to strategically release ferulic acid at rates and concentrations relevant for topical applications such as skin care products.

Bio-based Polymer from Ferulic Acid by Electropolymerization

“…Ferulic acid has many physiological functions including antimicrobial, anti-oxidant, anti-thrombotic, and carcinostatic activities; it has been studied for its applications in the food, cosmetic, and pharmaceutical fields (Ou and Kwok 2004;Pei et al 2015;Takahashi et al 2015). Bioactive polymers, which are based on ferulic acid, can also be prepared by incorporating ferulic acid into the polymer backbone, which can be regenerated again via biodegradation (Nagata and Hizakae 2003;Ouimet et al 2015Ouimet et al , 2013. However, these conversion processes involve several steps.…”

Biodegradable Kojic Acid-Based Polymers: Controlled Delivery of Bioactives for Melanogenesis Inhibition

“…As expected, 4e was the most hydrophilic dienol, presumably due to the increase in oxygen content. 36 The remaining dienols followed a trend of increasing aliphatic content between the KA moieties, where longer aliphatic chains corresponded to a higher log P . All compounds possessed a log P value greater than KA, which has been reported as low as −1.11 and as high as −0.66.…”

“…Using these reference samples’ of published log P o,w values, a calibration curve was generated in which log P o,w values were plotted on the y -axis with log k w values, obtained from the same method as above, were plotted on the x -axis. 35,36 Dienol log P values were then calculated from the curve using eq 2. $$k_{\mathrm{w}}=false(t_{\mathrm{R}}-t_{0}false)/t_0$$ $$\text{log }P=\text{slope }x\text{ log }{k}_{\mathrm{w}}+y-\text{intercept}$$…”

Processing, Valorization and Application of Bio-Waste Derived Compounds from Potato, Tomato, Olive and Cereals: A Review

“…In this study by incorporating FA into a polymer backbone FA retained its antioxidant activity when released via polymer degradation. Further, the FA-based polymer prevented discoloration, indicating a promising FA-based topical formulation [334].…”

“…In general, the main drawback related to the use of extracted natural phenols is their generally limited temperature stability, which causes their degradation during the polymer melt processing. Furthermore, natural phenols have often limited solubility in polymers [334].…”