3'-HYDROXYFLAVANONE

Base Information

• Chemical Name: 3'-HYDROXYFLAVANONE
• CAS No.: 1621-55-2
• Molecular Formula: C15H12 O3
• Molecular Weight: 240.258
• Hs Code.: 2932999099
• Mol file: 1621-55-2.mol

Synonyms:Flavanone,3-hydroxy- (6CI,7CI,8CI); 3-Hydroxyflavanone

Chemical Property of 3'-HYDROXYFLAVANONE

Chemical Property:

• Melting Point: 139-141℃
• Boiling Point: 441.6°Cat760mmHg
• Flash Point: 171.4°C
• PSA: 46.53000
• Density: 1.298g/cm³
• LogP: 3.09870
• Storage Temp.: 2-8°C

Purity/Quality:

99%HPLC ^*data from raw suppliers

3-Hydroxy-2-phenylchroman-4-one 98% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3'-HYDROXYFLAVANONE

There total 49 articles about 3'-HYDROXYFLAVANONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

cis-3-hydroxyflavanone dimethyl acetal (94137-50-5) → rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7)

Guidance literature:

With hydrogenchloride; In acetone; for 2h; Ambient temperature;

DOI:10.1021/jo00202a001

Reference yield: 85.0%

Trimethyl-(2-phenyl-2H-chromen-4-yloxy)-silane → rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -78 ℃; for 30h;

DOI:10.1021/jo00088a015

Reference yield: 75.0%

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7) → Flavanon-3-ol (1621-55-2)

Guidance literature:

With magnesium carbonate hydroxide hydrate; dihydrogen peroxide; In water; at 80 ℃; for 2h; Solvent; Temperature;

DOI:10.1002/adsc.201300555

upstream raw materials:

2-hydroxychalcone

trans-3-acetoxyflavanone

2-(2-chloroacetyl)phenol

benzaldehyde

Downstream raw materials:

3-hydroxyflavone

rac-trans-3-hydroxyflavanone

C₂₉H₂₂O₅

rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one

Refernces

7-O-METHYL-(2R:3R)-DIHYDROQUERCETIN 5-O-β-D-GLUCOSIDE AND OTHER FLAVONOIDS FROM PODOCARPUS NIVALIS

10.1016/S0031-9422(00)84968-7

The research investigate the flavonoid glycosides present in New Zealand Podocarpus species, specifically Podocarpus nivalis, as part of a chemotaxonomic survey. The study aimed to either support or refute the proposed subdivision of the classical gymnosperm genus Podocarpus into five different genera by identifying unique flavonoid glycosides in these species. The researchers isolated several new flavonoid glycosides, including luteolin 3’-O-β-D-xyloside, luteolin 7-O-β-D-glucoside-3’-O-β-D-xyloside, dihydroquercetin 7-O-β-D-glucoside, 7-O-methyl-(2R: 3R)-dihydrokaempferol 5-O-β-D-glucopyranoside, 7-O-methyl-(2R: 3R)-dihydroquercetin 5-O-β-D-glucopyranoside, 7-O-methylkaempferol 5-O-β-D-glucopyranoside, and 7-O-methylquercetin 5-O-β-D-glucopyranoside. They used various techniques such as absorption spectroscopy, acid and enzyme hydrolysis, sugar analysis, and NMR spectroscopy to identify and confirm the structures of these compounds. The study concluded that glucosylation of the 5-hydroxyl group in (+)-dihydroflavonols reverses the sign of rotation at 589 nm, and it highlighted diagnostic characteristics of substituted dihydroflavonols that can be useful in future research.

ENANTIOSELECTIVE SYNTHESIS OF FLAVONOIDS. PART 1. POLY-OXYGENATED CHALCONE EPOXIDES

10.1016/S0040-4020(01)82043-3

The research focuses on the enantioselective synthesis of poly-oxygenated chalcone epoxides, which are potentially useful as chiral precursors for the synthesis of enantiomerically enriched dihydroflavonols. The study employs the epoxidation of various poly-oxygenated chalcones using hydrogen peroxide (H2O2) in the presence of poly-α-amino acid catalysts. The resulting chiral aromatic oxygenated epoxides were characterized by their optical yields and absolute configurations, which were determined using circular dichroism (CD) spectroscopy. The research found that the oxygen functionalities and the position of substituents on the chalcone structure significantly influence the stereochemistry of the reaction. However, the study also encountered challenges such as low chemical yields and decreased optical purity during the conversion of the epoxides to dihydroflavonols, indicating that further optimization is needed to enhance the practicality of this synthetic approach for the production of C-4-oxygenated flavonoids.