724434-08-6

Basic information

• Product Name: 3,5,7,4''-TETRAHYDROXYFLAVANONE
• Synonyms: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS NO: 724434-08-6
• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25218
• Mol File: 724434-08-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5,7,4''-TETRAHYDROXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,7,4''-TETRAHYDROXYFLAVANONE(724434-08-6)
• EPA Substance Registry System: 3,5,7,4''-TETRAHYDROXYFLAVANONE(724434-08-6)

Safety Data

• Hazardous Substances Data: 724434-08-6(Hazardous Substances Data)

Upstream product

• 520-18-3 kaempferol 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 25515-46-2 2',4',6',4-tetrahydroxydihydrochalcone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 104435-34-9 C₂₃H₂₈O₉ 
• 3162-03-6 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 742072-29-3 7-acetoxy-2-(4-acetoxy-phenyl)-3,5-dihydroxy-chroman-4-one 
• 26207-81-8 3-acetoxy-4',5,7-trihydroxyflavanone 
• 55313-03-6 1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone 
• 27200-12-0 ampelopsin 

Downstream Products

• 520-18-3 kaempferol 
• 118333-31-6 (2S,3S)-3,40,5,7-tetrahydroxyflavanone 
• 480-20-6 Aromadendrin 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 3316-46-9 apigenin triacetate 

Relevant articles and documents

Synthesis, biological evaluation, and molecular docking of dihydroflavonol derivatives as anti-inflammatory agents

A series of dihydroflavonol derivatives (4a–4l) were synthesized from chalcones via classical Algar–Flynn–Oyamada (AFO) reaction and characterized on the basis of spectroscopic analyses. All synthesized compounds were evaluated for their inhibitory activity against the pro-inflammatory-inducible TNF-alpha, IL-1beta, and IL-6 in lipopolysaccharide (LPS)-stimulated RAW 264.7 cell lines and showed various efficiency. Furthermore, compounds 4d and 4k were selected to examine their in vivo anti-inflammatory activity by using two classical models. Herein compound 4k showed maximum anti-inflammatory activity of 32.98% inhibition in mice ear-swelling model and 40.06% inhibition at the 2 h intervals in rat paw edema model in comparison to the two references: aspirin and meloxicam. Similar effect was observed at a lower dose. In addition, the compound 4k was docked against cyclooxygenases-2 to validate the attained pharmacological data and provide understandable evidence for the observed anti-inflammatory activity.

Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives

Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and showed various efficiency. Compounds D1–D30 showed no toxic effects on RAW 264.7 cells at the concentration 20 μM; among them, compounds D9, D13, and D19 exhibited best anti-inflammatory activity through decreasing IL-1β, IL-6, and TNF-α. Furthermore, their structure–activity relationships were discussed preliminarily.

Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant.