87562-76-3

Basic information

• Product Name: kelampayoside A
• Synonyms: kelampayoside A;3,4,5-Trimethoxyphenyl 6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranoside
• CAS NO: 87562-76-3
• Molecular Formula: C₂₀H₃₀O₁₃
• Molecular Weight: 478.4444
• Mol File: 87562-76-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 685.6 °C at 760 mmHg
• Flash Point: 368.4 °C
• Appearance: /
• Density: 1.41 g/cm³
• CAS DataBase Reference: kelampayoside A(CAS DataBase Reference)
• NIST Chemistry Reference: kelampayoside A(87562-76-3)
• EPA Substance Registry System: kelampayoside A(87562-76-3)

Safety Data

• Hazardous Substances Data: 87562-76-3(Hazardous Substances Data)

Usage

General Description

Kelampayoside A is a natural compound isolated from the roots of the plant Syzygium myrtifolium. It belongs to the class of flavonoid compounds and has been found to possess various biological activities. Kelampayoside A has been demonstrated to exhibit strong anti-inflammatory and antioxidant properties, making it a potentially valuable compound for the development of new drugs for treating inflammation-related disorders and oxidative stress-related diseases. Additionally, it has shown promising cytotoxic activity against cancer cells, indicating its potential as a candidate for anticancer drug development. The discovery of Kelampayoside A highlights the importance of natural products in drug discovery and development, and its diverse biological activities make it a promising candidate for further research and development.

Upstream product

• 245432-69-3 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside 
• 642-71-7 3,4,5-trimethoxyphenol 
• 209113-70-2 3,4,5-trimethoxyphenyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 35784-51-1 ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 209113-72-4 3,4,5-trimethoxyphenyl 6-O-(5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside 

Relevant articles and documents

An expeditious route to the synthesis of kelampayosides A and B

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri- O-benzoyl-1-thio-β-D-glucopyranoside (13) with ethyl 2,3-di-O-acetyl-5-O- benzyl-1-thio-α/β-erythro-apiofuranoside (4a) gave direct 14 in an excellent yield. BF3·Et2O-catalysed condensation of the α- trichloroacetimidate 31, accessible in two steps from 14, with 3,4,5- trimethoxyphenol gave β-linked derivative 32 followed by deprotection gave Kelampayoside A. Protecting group manipulations of 32 and subsequent caffeoylation of resulting 36 followed by deprotection gave Kelampayoside B.

Three new hemiterpene glycosides from Ilex macropoda

Phytochemical studies of Ilex macropoda led to the isolation of three new hemiterpene glycosides, 4-β- D-glucopyranosyloxy-5-hydroxyprenyl caffeate (aohada-glycoside A), 5-caffeoyloxy-4-β-D-glucopyranosyloxy-prenyl alcohol (aohada-glycoside B), 4-(6-O-caffeoyl-β-D-glucopyranosyloxy)-5- hydroxyprenyl caffeate (aohada-glycoside C), together with betulin, acetyl ursolic acid, ilexosides XVII and XVIII, and 3,4,5-trimethoxyphenol β-D-5- O-caffeoyl-apiofuranosyl-(1→6)-β-D-glucopyranoside from the bark. Rotundioic acid, ursolic acid, ilexosides II and XXX, ziyu-glycoside I and rutin were also isolated from fresh leaves, and 3,5-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid from the wood.