Abstract
Tyrosinase is the key and rate-limiting enzyme responsible for the conversion of tyrosine into melanin. Competitive inhibition of tyrosinase enzymatic activity results in decreased or absent melanin synthesis by melanocytes in human skin. DeoxyArbutin (4-[(tetrahydro-2H-pyran-2-yl)oxy]phenol), a novel skin whitening agent, was synthesized through the removal of hydroxyl groups from the glucose side-chain of arbutin. DeoxyArbutin not only shows greater inhibition of tyrosinase activity but is also safer than hydroquinone and arbutin. Hence, deoxyArbutin is a potential skin whitening agent for cosmetics and depigmenting drugs; however, stability of this compound under some conditions remains a problem. The lack of stability poses developmental and practical difficulties for the use of deoxyArbutin in cosmetics and medicines. Improving the thermostability of deoxyArbutin is an important issue for its development. In this research, we established an analytical procedure to verify the amount of deoxyArbutin in solutions using a high performance liquid chromatographic (HPLC) method. The results indicate that this novel skin whitening agent is a thermolabile compound in aqueous solutions. Additionally, the rate constant for thermodegradation (k) and the half-life (t1/2) of deoxyArbutin were determined and can be used to understand the thermodegradation kinetics of deoxyArbutin. This information can aid in the application of deoxyArbutin for many future uses.
Highlights
Human melanin is the skin’s most important protection against the harmful effects of UV light, the dark skin caused by melanin accumulation is not considered cosmetically pleasing to most people [1,2,3]
We established the analytical procedure to confirm the quantity of deoxyArbutin in solutions using an high performance liquid chromatographic (HPLC) method
Previous research has examined the solubility of deoxyArbutin in an ethanoic solutions, and the results showed that deoxyArbutin can be dissolved in a simple vehicle of propylene glycol-ethanol-water at a 1:2:1 (v/v/v) ratio or 1:1 (v/v) ethanol-water [13]
Summary
Human melanin is the skin’s most important protection against the harmful effects of UV light, the dark skin caused by melanin accumulation is not considered cosmetically pleasing to most people [1,2,3]. The increased levels of melanin are characteristic of a great number of skin diseases, including Melasma, Solar Lentigines, and Post-inflammatory Hyperpigmentation. There is an increasing desire for the development of skin whitening agents for both beauty and therapeutic purposes [4,5]. Tyrosine is the precursor for the synthesis of melanin. Tyrosinase is the key and rate-limiting enzyme responsible for the conversion of tyrosine into melanins by melanocytes in human skin [6,7]. Inhibition of the enzymatic activity of tyrosinase by competitive inhibitors results in decreased or absent melanin synthesis by the melanocytes in human skin [8,9]
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