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

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

Uses

Used in Pharmaceutical Industry:
Kelampayoside A is used as a potential drug candidate for the treatment of inflammation-related disorders due to its strong anti-inflammatory properties. Its ability to modulate inflammatory responses can provide relief and management of various conditions characterized by excessive inflammation.
Kelampayoside A is also used as a potential drug candidate for the treatment of oxidative stress-related diseases. Its antioxidant properties can help mitigate the damaging effects of oxidative stress on cells and tissues, thereby preventing or treating diseases associated with oxidative damage.
Used in Anticancer Applications:
Kelampayoside A is used as an anticancer agent, demonstrating promising cytotoxic activity against cancer cells. Its potential to target and eliminate cancer cells makes it a candidate for further research and development in the field of oncology.
Used in Drug Discovery and Development:
Kelampayoside A is used as a promising candidate in drug discovery and development due to its diverse biological activities. Its discovery underscores the significance of natural products in identifying new therapeutic agents with potential applications in various medical fields. Further research and development of Kelampayoside A may lead to the creation of novel drugs with improved efficacy and safety profiles.

Upstream product

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

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.

Synthesis of 3,4,5-trimethoxyphenyl 5-O-caffeoyl-β-D-erythro- apiofuranosyl-(1→6)-β D-glucopyranoside: Kelampayoside B

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri- O-benzoyl-1-thio-β-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O- benzyl-1-thio-β-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the α-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxyphenol gave β-linked derivative 19 which could be transformed in five steps into the title compound.

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.