23598-08-5

Basic information

• Product Name: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate
• Synonyms: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate
• CAS NO: 23598-08-5
• Molecular Weight: 524.479
• Mol File: 23598-08-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate(23598-08-5)
• EPA Substance Registry System: methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate(23598-08-5)

Safety Data

• Hazardous Substances Data: 23598-08-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 117405-51-3 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside 
• 2309-07-1 Methyl ferulate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 494-08-6 glucovanillin 

Downstream Products

• 66642-79-3 trans-ferulic acid methyl ester 4-tetraacetylglucoside 
• 124151-33-3 coniferin 
• 94393-06-3 4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester 

Relevant articles and documents

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation

This work describes the chemical synthesis of O-aryl-β-D-glucosides and 1-O-β-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-β-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-β-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-β-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the π-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.