111003-33-9

Basic information

• Product Name: (-)-Dihydroquercetin
• Synonyms: (2S,3S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
• CAS NO: 111003-33-9
• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25158
• Mol File: 111003-33-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 232-234 °C(Solv: ethanol (64-17-5))
• Boiling Point: 687.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.702±0.06 g/cm3(Predicted)
• PKA: 7.39±0.60(Predicted)
• CAS DataBase Reference: (-)-Dihydroquercetin(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Dihydroquercetin(111003-33-9)
• EPA Substance Registry System: (-)-Dihydroquercetin(111003-33-9)

Safety Data

• Hazardous Substances Data: 111003-33-9(Hazardous Substances Data)

Usage

Uses

(-)-Taxifolin is a flavanoid compound which modulates chemopreventive genes. Inhibits NO production in cells.

Upstream product

• 29838-67-3 astilbin 
• 109430-52-6 (-)-taxifolin 3-O-β-D-xylopyranoside 
• 109430-54-8 (-)-epitaxifolin 3-O-β-D-xylopyranoside 
• 69256-15-1 (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan 
• 850177-05-8 (E)-3-[3,4-bis(methoxymethoxy)phenyl]acrylic acid 
• 120677-47-6 1,3,5-tris(methoxymethoxy)benzene 
• 331-39-5 caffeic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 36804-12-3 (E)-3-(3,4-bis(methoxymethoxy)phenyl)-1-(2,4,6-tris(methoxymethoxy)phenyl)-prop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 480-18-2 (+/-)-taxifolin 
• 480-18-2 (-)-epitaxifolin 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 

Downstream Products

• 480-18-2 (2S,3S)-taxifolin 3-O-β-D-glucoside 
• 6685-67-2 (+/-)-taxifolin pentaacetate 
• 480-18-2 taxifolin 
• 1186493-51-5 (2S,3S)-3',4',5,7-tetrahydroxy-2,3-dihydroflavonol-6-C-β,D-glucopyranoside 
• 112494-39-0 (2R,3R)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-β-D-glucopyranoside 
• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 493-36-7 (±)-alphitonin 
• 117-39-5 quercetol 
• 1089147-17-0 (2R,3R)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-(prop-2-ynyloxy)chroman 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 

Relevant articles and documents

Chemical Studies on the Mistletoe. IV. The Structure of Isoglucodistylin, a New Flavonoid Glycoside Isolated from Taxillus kaempferi

A new flavonoid glycoside, isoglucodistylin was isolated from Taxillus kaempferi, and (2R,3S)-taxifolin 3-β-D-glucopyranoside was assigned to this substance from studies on the hydrolysis products and on the isomerization products, and from analyses of the carbon-13 NMR spectra.

-

-

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.

Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives

A series of C7-O- and C20-O-amidated 2,3-dehydrosilybin (DHS) derivatives ((±)-1a-f and (±)-2), as well as a set of alkenylated DHS analogues ((±)-4a-f), were designed and de novo synthesized. A diesteric derivative ofDHS((±)-3) and two C23 esterifiedDHSanalogues ((±)-5a and (±)-5b) were also prepared for comparison. The cell viability of PC12 cells, Fe2+ helation, lipid peroxidation (LPO), free radical scavenging, and xanthine oxidase inhibition models were utilized to evaluate their antioxidative and neuron protective properties. The study revealed that the diether atC7-OHand C20-OHas well as the monoether at C7-OH, which possess aliphatic substituted acetamides, demonstrated more potent LPO inhibition and Fe2+chelation compared to DHS and quercetin. Conversely, the diallyl ether at C7-OH and C20-OH was more potent in protection of PC12 cells against H2O2-induced injury than DHS and quercetin. Overall, the more lipophilic alkenylated DHS analogues were better performing neuroprotective agents than the acetamidated derivatives. The results in this study would be beneficial for optimizing the therapeutic potential of lignoflavonoids, especially in neurodegenerative disorders such as Alzheimer's and Parkinson's disease.