23405-70-1

Basic information

• Product Name: 5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE
• Synonyms: 5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE;3-Hydroxy-5,7-bis(phenylMethoxy)-2-[4-(phenylMethoxy)phenyl]-4H-1-benzopyran-4-one;4',5,7-Tris(benzyloxy)-3-hydroxy-flavone
• CAS NO: 23405-70-1
• Molecular Formula: C₃₆H₂₈O₆
• Molecular Weight: 556.60392
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles
• Mol File: 23405-70-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 756.2°C at 760 mmHg
• Flash Point: 244°C
• Appearance: /
• Density: 1.299g/cm³
• Vapor Pressure: 4.92E-24mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Refrigerator
• Solubility: Chlorofrom (Sparingly), DMSO
• PKA: 8.07±0.20(Predicted)
• CAS DataBase Reference: 5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE(23405-70-1)
• EPA Substance Registry System: 5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE(23405-70-1)

Safety Data

• Hazardous Substances Data: 23405-70-1(Hazardous Substances Data)

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

• 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 
• 88607-79-8 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 96333-59-4 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one 

Downstream Products

• 1232680-40-8 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-((1S,5S)-5-methyl-4-oxocyclohex-2-enyloxy)-4H-chromen-4-one 
• 1232680-31-7 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-((1R,5R)-5-methyl-4-oxocyclohex-2-enyloxy)4H-chromen-4-one 
• 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 

Relevant articles and documents

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.

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.

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.