Efficient Enzymatic Synthesis of Lipophilic Phenolic Glycoside Azelaic Acid Esters and Their Depigmenting Activity was written by Xu, Haixia;Li, Xiaofeng;Xin, Xuan;Mo, Lan;Zou, Yucong;Zhao, Guanglei. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Related Products of 27208-80-6 The following contents are mentioned in the article:
In this paper, an enzymic route for synthesizing phenolic glycoside azelaic acid esters was successfully set up via lipase-catalyzed esterification and transesterification. Among the lipases tested, Candida antarctica lipase B (Novozyme 435) showed the highest activity in catalyzing esterification and Thermomyces lanuginosus (Lipozyme TLIM) gave the highest substrate conversion in catalyzing transesterification for the synthesis of ester. The addition of 4A mol. sieves into the reaction system is found to be an effective method for in situ absorption of the byproduct water and methanol, with which the substrate conversions of the enzymic esterification and transesterification were 98.7 and 95.1%, resp. Also, the main product ratios in transesterification were above 99.0% with lipozyme TLIM as a catalyst because the hydrolysis reaction was hindered. The results of the phys. and biol. properties indicate that all esters had higher Clog p values than their parent compounds Also, the esters showed higher intracellular tyrosinase inhibitory and depigmentating activities than phenolic glycosides, azelaic acid (AA), and their phys. mixtures due to their higher membrane penetration and tyrosinase inhibitory effects. In particular, piceid 6′′-O-azelaic acid ester (PIA) showed the strongest inhibitory effect against melanin production Its inhibitory rate was 77.4% at a concentration of 0.25 mM, about 4.2 times higher than that of arbutin (18.5%). This study involved multiple reactions and reactants, such as (2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 27208-80-6Related Products of 27208-80-6).
(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 27208-80-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Related Products of 27208-80-6
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts