23405-70-1

Usage

Chemical Properties

Light Brown Solid

InChI:InChI=1/C36H28O6/c37-34-33-31(41-24-27-14-8-3-9-15-27)20-30(40-23-26-12-6-2-7-13-26)21-32(33)42-36(35(34)38)28-16-18-29(19-17-28)39-22-25-10-4-1-5-11-25/h1-21,38H,22-24H2

Upstream product

• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 
• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 1246814-24-3 2-benzoyloxy-2'-(4''-(benzyloxy)benzoyloxy)-4',6'-dibenzyloxyacetophenone 
• 1246814-23-2 2'-(4''-(benzyloxy)benzoyloxy)-4',6'-dibenzyloxy-2-bromoacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 1192260-72-2 2'-(4''-(benzyloxy)benzoyloxy)-4',6'-dibenzyloxyacetophenone 
• 100-39-0 benzyl bromide 
• 23243-67-6 3-(4-benzyloxyphenyl)-1-(2,4-dibenzyloxy-6-hydroxyphenyl)prop-2-en-1-one 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 480-41-1 naringenin 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Downstream Products

• 1246814-39-0 5,7,4'-tri-O-benzyl-3-O-(2'',3'',5''-tri-O-benzoyl-β-D-ribofuranosyl)kaempferol 
• 1246814-29-8 5,7,4'-tri-O-benzyl-3-O-(3'',6''-di-O-allyl-2'',4''-di-O-benzoyl-β-D-glucopyranosyl)kaempferol 
• 1246814-35-6 5,7,4'-tri-O-benzyl-3-O-(2'',4''-di-O-acetyl-3'',6''-di-O-allyl-β-D-glucopyranosyl)kaempferol 
• 480-10-4 astragalin 
• 1254190-95-8 4',7-di-O-benzyl-3-O-(2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)kaempferol 
• 1254190-96-9 4',7-di-O-benzyl-3-O-(2-O-(α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)kaempferol 
• 30652-27-8 4',7-di-O-benzyl-kaempferol 
• 520-18-3 kaempferol 
• 1313028-11-3 C₈₁H₆₈O₁₄ 
• 1313028-12-4 C₈₁H₆₈O₁₄ 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols

The synthesis of two series of five kaempfer-3-ols was described. The first set all have a C-3 hydroxyl group and the second has a carboxymethoxy ether at the C-3 position. Both series have variable substitution at the C-4 position (i.e., OH, Cl, F, H, OMe). Both kaempferols and carboxymethoxy ethers were evaluated for their ability to inhibit ribosomal s6 kinase (RSK) activity and cancer cell proliferation.

NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS

The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.

Study of kaempferol glycoside as an insulin mimic reveals glycon to be the key active structure

Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1), a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

Synthesis of kaempferol 3- O -(3″,6″-Di- O - E - p -coumaroyl)-β- D -glucopyranoside, efficient glycosylation of flavonol 3-OH with glycosyl o -alkynylbenzoates as donors

Kaempferol 3-O-(3″,6″-di-O-E-p-coumaroyl)-β-d- glucopyranoside (1), an optimal metabolite of Scots pine seedlings for protection of deep-lying tissue against damaging UV-B, represents a typical acylated flavonol 3-O-glycoside. This compound was synthesized for the first time via two approaches. The first approach, starting with kaempferol, featured formation of the flavonol 3-O-glycosidic linkage with a glycosyl bromide under conventional PTC conditions. In the second approach, 5,7,4′-tri-O-benzyl- kaempferol was readily prepared from 2′,4′,6′- trihydroxyacetophenone and p-hydroxybenzoic acid, which was coupled with a glucopyranosyl o-hexynylbenzoate under the catalysis of a gold(I) complex to provide the desired 3-O-glycoside in excellent yield. A variety of the glycosyl o-hexanylbenzoates equipped with the 2-O-benzoyl group were also proven to be highly efficient donors for construction of the flavonol 3-O-glycosidic linkages.

De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation

(Chemical Equation Presented) The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.

Synthesis of a potent and selective inhibitor of p90 Rsk

(Chemical Equation Presented) The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.