Comparative esterification of phenylpropanoids versus hydrophenylpropanoids acids catalyzed by lipase in organic solvent media

Chemo-enzymatic Synthesis, Derivatizations, and Polymerizations of Renewable Phenolic Monomers Derived from Ferulic Acid and Biobased Polyols: An Access to Sustainable Copolyesters, Poly(ester-urethane)s, and Poly(ester-alkenamer)s

“…However, lipase-mediated direct esterification of p-hydroxycinnamic acids (60-70) with alcohols generally suffers from long reaction time and/or low yields. To improve the efficiency of this reaction, one can either reduce the conjugated unsaturation (via catalytic hydrogenation) (65,(70)(71)(72)(73)(74)(75), use alkyl p-hydroxycinnamates (e.g., ethyl, n-octyl) (70,73,(75)(76)(77)(78)(79)(80)(81)(82)(83) or ionic liquids as solvents (68,84,85). Therefore, to warrant high yields transesterifications with the selected primary and/or secondary alcohols (i.e., ethylene glycol, 1,3-propanediol, 1,4-butanediol, isosorbide, and glycerol), the initial step of our synthetic approach was the production of ethyl dihydroferulate (2).…”

Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism

“…Alternatively, lipases have been successfully applied in the regioselective synthesis of sugar esters of phenylpropanoid related compounds and for the preparation of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic media [22] – [27] . More specifically, the comparative reactivity of phenylpropanoids such as caffeic and ferulic acids versus the corresponding dihydrophenyl propanoid acids revealed the strong influence of propanoid chain unsaturations on the transformation of these compounds by Candida antarctica lipase B (CaL-B) in organic solvent media [23] . According to the literature, saturated derivates of caffeic and ferulic acids have higher free radical scavenging activities than their corresponding unsaturated analogs, suggesting that this activity may be extended to the corresponding PPG analogs.…”

Isolation of new esters from the stems ofCinnamomum reticulatumHay

“…Altogether, the individual components of this mixture were identified as 4-hydroxy-3-methoxyphenethyl butyrate (1), 4-hydroxy-3-methoxyphenethyl hexyrate (2), 4-hydroxy-3-methoxyphenethyl pentadecyrate (3), 4-hydroxy-3-methoxyphenethyl stearate (4) and 4-hydroxy-3-methoxyphenethyl heneicosyrate (5). Compounds 3-5 are new compounds (Cassani, Luna, Navarro, & Castillo, 2007).…”