499-21-8

Upstream product

• 119014-23-2 3-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid ethyl ester 
• 40555-40-6 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde 
• 80585-56-4 methyl pentaacetyl-4-O-β-D-glucopyranosylcaffeate 
• 39175-73-0 Platyconin chloride 
• 67-56-1 methanol 
• 80585-53-1 (E)-3-[4-Hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-((E)-2-methoxycarbonyl-vinyl)-phenoxy]-tetrahydro-pyran-2-ylmethyl ester 

Downstream Products

• 147511-61-3 4-O-(β-D-glucopyranosyl)-trans-caffeic acid 
• 80585-57-5 (E)-3-[3-Hydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester 

Relevant academic research and scientific papers

Structure of anthocyanin from the blue petals of Phacelia campanularia and its blue flower color development

The dicaffeoyl anthocyanin, phacelianin, was isolated from blue petals of Phacelia campanularia. Its structure was determined to be 3-O-(6-O-(4′-O- (6-O-(4′-O-β-D-glucopyranosyl-(E)-caffeoyl)-β-D-glucopyranosyl) -(E)-caffeoyl)-β-D-glucopyranosyl)-5-O-(6-O

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.

STRUCTURE OF CINERARIN, A TETRA-ACYLATED ANTHOCYANIN ISOLATED FROM THE BLUE GARDEN CINERARIA, SENECIO CRUENTUS

Structure of cinerarin is determined to be 3-O-(6-O-malonyl-β-D-glucopyranosyl)-7-O-(6-O-(4-O-(6-O-caffeyl-β-D-glucopyranosyl)caffeyl)-β-D-glucopyranosyl)-3'-O-(6-O-caffeyl-β-D-glucopyranosyl)delphinidin.

STRUCTURE OF PLATYCONIN, A DIACYLATED ANTHOCYANIN ISOLATED FROM THE CHINESE BELL-FLOWER PLATYCODON GRANDIFLORUM

Structure of platyconin is determined to be 3-O-(6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl)-7-O-(6-O-(trans-4-O-(6-O-(trans-4-O-(β-D-glucopyranosyl)-caffeoyl)-β-D-glucopyranosyl)caffeoyl)-β-D-glucopyranosyl)delphinidin.

HEAVENLY BLUE ANTHOCYANIN II TRANS-4-O-(6-O-(TRANS-3-O-(β-D-GLUCOPYRANOSYL)CAFFEYL)-β-D-GLUCOPYRANOSYL)-CAFFEIC ACID, A NOVEL COMPONENT IN HEAVENLY BLUE ANTHOCYANIN

Structure of an alkaline hydrolysis product of heavenly blue anthocyanin was determined to be trans-4-O-(6-O-(trans-3-O-(β-D-glucopyranosyl)caffeyl)-β-D-glucopyranosyl)caffeic acid (1).