4250-77-5

Basic information

• Product Name: 6-HYDROXYFLAVANONE
• Synonyms: HYDROXYFLAVANONE, 6-;6'-HYDROXYFLAVANONE;6-HYDROXYFLAVANONE;6-Hydroxyflavanone,98+%;HYDROXYFLAVANONE, 6-(RG);(2R)-6-hydroxy-2-phenyl-chroman-4-one;2-Phenyl-6-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one;6-OH Flavanone
• CAS NO: 4250-77-5
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• EINECS: -0
• Product Categories: Flavanones;Biochemistry;Flavonoids;Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 4250-77-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 220-222 °C (dec.)(lit.)
• Boiling Point: 464.3ºC at 760 mmHg
• Flash Point: 181.2ºC
• Appearance: Slightly yellow-cream powder
• Density: 1.288g/cm3
• Vapor Pressure: 3.05E-09mmHg at 25°C
• Refractive Index: 1.631
• PKA: 9.53±0.40(Predicted)
• BRN: 87354
• CAS DataBase Reference: 6-HYDROXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXYFLAVANONE(4250-77-5)
• EPA Substance Registry System: 6-HYDROXYFLAVANONE(4250-77-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4250-77-5(Hazardous Substances Data)

Usage

Chemical Properties

Slightly yellow-cream powder

Uses

6-Hydroxyflavanone (6-HF) has been used for the enantiomeric separation of flavonoids using polysaccharide-based chiral stationary phases by nano-liquid chromatography (nano-LC). Racemic 6-HF may be used in the synthesis of 6-propionoxy-flavanone (6-PF). 6-HF may be employed as synthetic flavone to investigate the mechanism of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induced cytotoxic and apoptotic effects in HeLa cancer cells.

Definition

ChEBI: A monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 6.

General Description

6-Hydroxyflavanone is a flavonoid. Its biotransformation by Aspergillus niger strains have been described. Crystal structure of S and R enanti-omers of 6-hydroxyflavanone has been reported to have four crystallographic sites of the unit cell in an approximate 3:1/1:3 ratio. It was identified as a metabolite of flavnone on incubation with rat liver microsomes by positive ion electrospray LC/MS analysis.

InChI:InChI=1/C15H12O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15-16H,9H2

Upstream product

• 100-52-7 benzaldehyde 
• 6665-83-4 6-hydroxyflavone 
• 19312-13-1 3-phenyl-1-(2,5-dihydroxyphenyl)-2-propen-1-one 
• 80096-64-6 6-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 90563-81-8 3-(4-hydroxyphenoxy)propionitrile 
• 123-31-9 hydroquinone 
• 3034-04-6 6-methoxyflavanone 
• 1289081-28-2 6-propionoxyflavanone 
• 76279-00-0 4-oxo-2-phenylchroman-6-yl acetate 
• 487-26-3 Flavanone 
• 31405-69-3 2’-hydroxy-5’-(methoxymethoxy)acetophenone 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 108238-41-1 3,6-dihydroxyflavone 
• 92496-92-9 5,6-dihydroxyflavanone 
• 76279-00-0 4-oxo-2-phenylchroman-6-yl acetate 
• 1289081-28-2 6-propionoxyflavanone 
• 6665-83-4 6-hydroxyflavone 
• 1228118-69-1 (-)-(S)-6,4'-dihydroxyflavanone 

Relevant articles and documents

Synthesis and evaluation of the thermal behavior of flavonoids: Thermal decomposition of flavanone and 6-hydroxyflavanone

Flavonoids in the broad sense of the term are virtually universal plant pigments. Synthesis of flavanone and 6-hydroxyflavanone was carried out and identified by H and C NMR. Details concerning the thermal behavior were evaluated by thermogravimetry under oxygen and nitrogen purge gases. Additionally, the kinetic studies were evaluated from several heating rates (5, 10 and 20?°C?min?1) and sample mass of 2?mg in open crucibles. The obtained data were evaluated with the isoconversional method, where the values of activation energy (Ea/kJ?mol?1) were plotted in function of the conversion degree (α). The results of thermal behavior of the flavanone under a nitrogen purge gas showed that this compound has a homogeneous degradation process while the hydroxyl group in the aromatic ring of 6-hydroxyflavanone there are two mass losses.

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.

A novel synthesis of naringenin and related flavanones

Efficient methods are reported for the preparation of naringenin (4',5,7-trihydroxyflavanone) which could be easily scaled-up. They have been applied to three other flavanones (6.hydroxyflavanone, 6,4'-dihydroxyflavanone, 6,3',4'-trihydroxyflavanone) suitably.