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

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

Uses

Used in Pharmaceutical Industry:
2'-Hydroxyflavanone is used as a pharmaceutical agent for its potential role in preventing and treating various health conditions. Its antioxidant, anti-inflammatory, and anti-cancer properties make it a promising candidate for the development of therapeutic interventions.
Used in Cancer Therapy:
In the field of oncology, 2'-Hydroxyflavanone is used as an anti-cancer agent, targeting the inhibition of cancer cell growth. Its ability to reduce inflammation and show promising results in preclinical studies positions it as a potential therapeutic option for cancer treatment.
Used in Nutraceutical Industry:
2'-Hydroxyflavanone is used as a nutraceutical ingredient for its health-promoting properties. Its presence in various plant sources, particularly citrus fruits, makes it a valuable component in dietary supplements and functional foods aimed at enhancing overall health and well-being.
Used in Cosmetic Industry:
Given its antioxidant and anti-inflammatory properties, 2'-Hydroxyflavanone is used in the cosmetic industry for the development of skincare products. It may contribute to the prevention of skin aging, protection against environmental stressors, and reduction of inflammation-related skin conditions.
Used in Agricultural Industry:
2'-Hydroxyflavanone's natural occurrence in plants and its health-promoting properties make it a potential candidate for use in agricultural applications. It could be utilized in the development of plant-based products or as a component in organic farming practices to enhance crop health and resistance to diseases.

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 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 108-95-2 phenol 

Downstream Products

• 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 
• 534569-40-9 C₁₆H₁₅N₃O₃ 
• 1386980-98-8 2-(4-oxochroman-2-yl)phenyl phenylcarbamate 

Relevant articles and documents

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

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.

Synthesis and evaluation of novel carbamate-substituted flavanone derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents

This study was designed to synthesize and evaluate flavanone derivatives with phenylcarbamate moiety as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents for management of AD. The synthesis of carbamate-substituted flavanone derivativ

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.

Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives

Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized compounds. The results of the antibacterial studies shows that compounds 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compound (2h) has remarkable activity against all strains viz. 25 μg/ml inhibitory concentration against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compound 2f possess minimum inhibitory concentration of 200 μg/ml against E. coli and S. typhimurium and 25 μg/ml against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compounds were performed and the predicted result showed that the compound having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivatives undergo demethylation reaction. The biologically active compounds are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.

Synthesis of flavanones using nanocrystalline MgO

The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.