17348-76-4

Basic information

• Product Name: 2'-HYDROXYFLAVANONE
• Synonyms: 2'-HYDROXYFLAVANONE;2-HYDROXYFLAVANONE;HYDROXYFLAVANONE, 2'-;HYDROXYFLAVANONE, 2'-(RG);2-(2-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one;2'-OH Flavanone;2-(2-hydroxyphenyl)-2,3-dihydrochromen-4-one;2-(2-hydroxyphenyl)chroman-4-one
• CAS NO: 17348-76-4
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Product Categories: Flavanones;Biochemistry;Flavonoids
• Mol File: 17348-76-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 164.0 to 168.0 °C
• Boiling Point: 184°C at 760 mmHg
• Flash Point: 65.1°C
• Appearance: /
• Density: 1.397g/cm³
• Vapor Pressure: 0.748mmHg at 25°C
• Refractive Index: 1.429
• CAS DataBase Reference: 2'-HYDROXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXYFLAVANONE(17348-76-4)
• EPA Substance Registry System: 2'-HYDROXYFLAVANONE(17348-76-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 17348-76-4(Hazardous Substances Data)

Usage

General Description

2'-Hydroxyflavanone is a chemical compound belonging to the flavanone class and is a derivative of flavone. It is a naturally occurring flavonoid found in various plant sources, including citrus fruits, and has been studied for its potential health benefits. 2'-Hydroxyflavanone has been reported to possess antioxidant, anti-inflammatory, and anti-cancer properties, and is being investigated for its potential role in preventing and treating various health conditions. Additionally, 2'-Hydroxyflavanone has shown promising results in preclinical studies for its ability to inhibit the growth of cancer cells and reduce inflammation, making it a compound of interest for further research and potential therapeutic applications.

InChI:InChI=1/C6H3F3O2/c7-6(8,9)5-2-1-4(3-10)11-5/h1-3H

Upstream product

• 15131-80-3 trans-2,2'-dihydroxychalcone 
• 89-95-2 2-methyl-benzyl alcohol 
• 118-93-4 o-hydroxyacetophenone 
• 5533-04-0 2-(methoxymethoxy)benzaldehyde 
• 90-02-8 salicylaldehyde 
• 1006623-69-3 2′-hydroxyflavylium tetrafluoroborate 
• 34000-30-1 2',2-dihydroxychalcone 
• 3055-86-5 3-phenoxypropionitrile 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 89466-08-0 2-hydroxyphenyl boronic acid 

Downstream Products

• 1386980-98-8 2-(4-oxochroman-2-yl)phenyl phenylcarbamate 
• 534569-40-9 C₁₆H₁₅N₃O₃ 
• 29337-79-9 2-[3-(2-hydroxyphenyl)propyl]phenol 
• 140480-04-2 4-[1,3-Bis-(2-hydroxy-phenyl)-propyl]-2-[3-(2-hydroxy-phenyl)-propyl]-phenol 

Relevant articles and documents

Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the s

5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer

Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2′-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR-dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum antiproliferative activity at 5–10 μM against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses.

2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2′ cyclize to form flavanones in basic media. By synthesizing 2′-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2′-dihydroxychalcone that in solution can evolve to 2′-hydroxyflavanone or back to 2′-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylium network of chemical reactions is briefly exploited.