94393-06-3

Upstream product

• 107668-85-9 helonioside D 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 
• 93343-68-1 protoplumericin B 
• 117591-89-6 3-O-feruloyl-6'-O-(4-O-β-D-glucopyranosylferuloyl)sucrose 
• 67-56-1 methanol 
• 107647-22-3 helonioside C 

Downstream Products

• 117405-51-3 4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside 
• 2309-07-1 Methyl ferulate 

Relevant academic research and scientific papers

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.

Iridoids of Apocynaceae. III. Minor Iridoids from Allamanda neriifolia

New iridoids, including isoallamandicin, allamcin, allamancin, 3-O-methyl derivatives of allamcin and allamancin, allamcidin, allamcidin glucoside, 13-O-acetylplumieride, plumiepoxide, and protoplumericin B, were isolated in addition to ten known iridoids from the stem and leaves of Allamanda neriifolia HOOK.Their structures were determined on the basis of spectral and chemical evidence.Gardenoside and 10-dehydrogardenoside, two ordinal-type iridoids, were also obtained.Keywords -iridoid; plumericin; plumieride; protoplumericin; plumericin monohydrate; plumericin dihydrate; epoxyplumieride; dihydroplumieride; 13-O-acylplumieride; Allamanda neriifolia, Apocynaceae.