118333-31-6

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, (2S,3S)-
• CAS NO: 118333-31-6
• Molecular Formula: C15H12O6
• Molecular Weight: 288.257
• Mol File: 118333-31-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, (2S,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, (2S,3S)-(118333-31-6)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-, (2S,3S)-(118333-31-6)

Safety Data

• Hazardous Substances Data: 118333-31-6(Hazardous Substances Data)

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 104435-34-9 C₂₃H₂₈O₉ 
• 480-41-1 naringenin 
• 480-41-1 (+)-Naringenin 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 724434-08-6 dihydrokaempferol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 482-38-2 kaempferitrin 
• 118160-11-5 tetrakis(methoxymethoxy) isosalipurpol 
• 104435-35-0 tetrakis(methoxymethoxy)isosalipurpol Epoxide 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 

Downstream Products

• 115728-45-5 (2S,3S)-(-)-aromadendrin trimethyl ether 
• 76792-94-4 (2R,3R)-(+)-4',5,7-trimethoxydihydroflavonol 
• 480-18-2 taxifolin 
• 57601-13-5 2'-hydroxy-4,α,4',6'-tetramethoxy-chalcone 
• 19879-29-9 (+/-)-epiafzelechin tetraacetate 
• 19879-29-9 (+/-)-afzelechin tetraacetate 
• 132400-79-4 (+/-)-2,3-trans-3,4-cis-4-methoxy-3,5,7,4'-tetraacetoxyflavan 
• 132400-76-1 (+/-)-afzelechin 5-methyl ether triacetate 
• 132400-74-9 (+/-)-afzelechin 3,7,4'-triacetate 
• 118205-77-9 (2S,3R,4R)-(-)-5,7,4'-trimethoxyflavan-3,4-diol 
• 118205-74-6 (2R,3S,4R)-(+)-5,7,4'-trimethoxyflavan-3,4-diol 
• 118205-76-8 (2S,3R,4S)-(-)-5,7,4'-trimethoxyflavan-3,4-diol 
• 118205-75-7 (2R,3S,4S)-(+)-5,7,4'-trimethoxyflavan-3,4-diol 
• 132400-77-2 (+/-)-2,3-trans-3,4-trans-4-hydroxy-3,5,7,4'-tetraacetoxyflavan 

Relevant articles and documents

In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.

cDNA corresponding to a flavonol synthase gene from Arabidopsis thaliana was cloned and expressed in Escherichia coli. The recombinant protein was purified to near-homogeneity and the catalytic properties of the enzyme were studied in vitro. Together with kaempferol and apigenin the recombinant protein synthesised the (2R,3S)-cis- and (2S,3S)-trans-isomers of dihydrokaempferol from the (2S)- and (2R)-isomers of naringenin, respectively. Flavanones and dihydroflavanols differing in degree of A- or B-ring hydroxylation were also accepted as substrates.

Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship

To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.

Heterocycles. XXII. Stereoselective Synthesis of (+)-Aromadendrin Trimethyl Ether and Its Enantiomer, and Their Reduction

Two enantiomeric chalcone epoxides 2a and 2b are synthesized under phase-transfer conditions using 1-benzylquinidinium chloride and 1-benzylquininium chloride as catalysts, respectively.Stereoselective cyclisation of 2a and 2b, followed by methylation and