64625-37-2

Usage

Uses

Used in Pharmaceutical Applications:
(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester is used as a pharmaceutical compound for its potential medicinal properties. (E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester's unique structure and functional groups may allow it to interact with biological targets, making it a candidate for the development of new drugs or therapies.
Used in Chemical Research:
In the field of chemical research, (E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester is used as a subject of study for understanding its reactivity, stability, and potential applications in various chemical reactions. Its complex structure may provide insights into new reaction mechanisms or the development of novel synthetic methods.
Used in Industrial Applications:
(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acrylic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester may be utilized in industrial applications due to its unique structure and functional groups. It could potentially be used as a building block for the synthesis of other complex molecules or as a component in the development of new materials with specific properties.

Upstream product

• 830322-96-8 1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose 
• 30572-07-7 2,3,4,6-tetra-O-chloroacetyl-D-glucopyranose 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 

Downstream Products

• 20905-74-2 3,5-di-O-β-D-glucopyranoside of cyanidin 

Relevant academic research and scientific papers

Engineering faster transglycosidases and their acceptor specificity

Transglycosidases are enzymes that have the potential to catalyze the synthesis of a wide range of high-value compounds starting from biomass-derived feedstocks. Improving their activity and broadening the substrate range are important goals to enable the widespread application of this family of biocatalysts. In this work, we engineered 20 mutants of the rice transglycosidase Os9BGlu31 and evaluated their catalysis in 462 reactions over 18 different substrates. This allowed us to identify mutants that expanded their substrate range and showed high activity, including W243L and W243N. We also developed double mutants that show very high activity on certain substrates and exceptional specificity towards hydrolysis, such as L241D/W243N. In order to guide a more general use of Os9BGlu31 variants as transglycosylation catalysts, we built cheminformatics models based on topological descriptors of the substrates. These models showed useful predictive potential on the external validation set and are allowing the identification of efficient catalytic routes to novel phytohormone and antibiotic glucoconjugates of interest.

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Synthesized p-coumaroyl and feruloyl l-tartrate esters were submitted to Brettanomyces bruxellensis strains AWRI 1499, AWRI 1608, and AWRI 1613 to assess their role as precursors to ethylphenols in wine. No evolution of ethylphenols was observed. Additionally, p-coumaroyl and feruloyl glucose were synthesized and submitted to B. bruxellensis AWRI 1499, which yielded both 4-ethylphenol and 4-ethylguaiacol. Unexpected chemical transformations of the hydroxycinnamoyl glucose esters during preparation were investigated to prevent these in subsequent synthetic attempts. Photoisomerization gave an isomeric mixture containing the trans-esters and undesired cis-esters, and acyl migration resulted in a mixture of the desired 1-O-β-ester and two additional migrated forms, the 2-O-α- and 6-O-α-esters. Theoretical studies indicated that the photoisomerization was facilitated by deprotonation of the phenol, and acyl migration is favored during acidic, nonaqueous handling. Preliminary LC-MS/MS studies observed the migrated hydroxycinnamoyl glucose esters in wine and allowed for identification of feruloyl glucose in red wine for the first time.