Related Experiment Video
Updated: Aug 7, 2025

Fabricating Superhydrophobic Polymeric Materials for Biomedical Applications
Published on: August 28, 2015
Synthesis of hydrophilic glyceryl monocaffeate with economical catalyst cation-exchange resin Amberlyst-35
Dami Li1,2, Xinying Wang1,2, Xuebei Hou1,2
1School of Food Science and Engineering, Henan University of Technology, Zhengzhou, PR China.
Background:
Caffeic acid (CA) has anti-oxidation and anti-inflammatory. However, the poor hydrophilicity of CA limits its biological activities. In this work, hydrophilic glyceryl monocaffeate (GMC) was synthesized by esterification using different caffeoyl donors (deep eutectic solvent and solid CA). Cation-exchange resins were used as the catalysts. The effects of reaction conditions were also investigated.
Results:
The mass transfer limitation of esterification was eliminated using deep eutectic solvent. Compared with the previous catalysts (immobilized lipase Novozym 435), an economic cation-exchange resin, Amberlyst-35 (A-35), showed good catalytic performance for GMC preparation. The activation energies of GMC synthesis and CA conversion were 43.71 kJ mol-1 and 43.07 kJ mol-1 , respectively. The optimal reaction conditions were a temperature reaction of 90 °C, catalyst load of 7%, glycerol/CA molar ratio of 5:1 (mol mol-1 ), and reaction time of 24 h, which resulted in a maximum GMC yield and CA conversion of 69.75 ± 1.03% and 82.23 ± 2.02%, respectively.
Conclusion:
The results of the work showed a promising alternative for the synthesis of GMC. © 2023 Society of Chemical Industry.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
10:54Facile and Efficient Preparation of Tri-component Fluorescent Glycopolymers via RAFT-controlled Polymerization
Published on: June 19, 2015
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis