Flavanone

Base Information

• Chemical Name: Flavanone
• CAS No.: 487-26-3
• Deprecated CAS: 24271-98-5
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 29329900
• European Community (EC) Number: 207-654-8
• NSC Number: 50393
• UNII: WX22P730FB
• DSSTox Substance ID: DTXSID9022318
• Nikkaji Number: J11.632G
• Wikidata: Q27077305
• NCI Thesaurus Code: C68459
• Pharos Ligand ID: DA7BC2RPL6TP
• Metabolomics Workbench ID: 129984
• ChEMBL ID: CHEMBL274318
• Mol file: 487-26-3.mol

Synonyms:(+-)-flavanone;flavanone;flavanone, (+-)-isomer;flavanone, (R)-isomer;flavanone, (S)-isomer;flavanone, 2-(14)C-labeled

Chemical Property of Flavanone

Chemical Property:

• Appearance/Colour: Very slightly yellow powder
• Vapor Pressure: 3.6E-06mmHg at 25°C
• Melting Point: 76-78 °C(lit.)
• Refractive Index: 1.603
• Boiling Point: 386.2 °C at 760 mmHg
• Flash Point: 181.9 °C
• PSA: 26.30000
• Density: 1.192 g/cm³
• LogP: 3.39310
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

98%,99%, ^*data from raw suppliers

Flavanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC2=CC=CC=C2C1=O)C3=CC=CC=C3
• Uses: Propafenone (P757500) impurity. Flavanone was used in HPLC coupled to electrospray ion trap mass spectrometric method for separation and detection of natural flavonoid aglycones. Silibinin, a flavanone, was used in a variety of biological functions.

Technology Process of Flavanone

There total 297 articles about Flavanone 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: 86.0%

(R)-3-Hydroxy-1-(2-hydroxy-phenyl)-3-phenyl-propan-1-one (351458-84-9) → (E)-2'-hydroxy-chalcone (888-12-0) + (2S)-flavanone (487-26-3,17002-31-2,24271-98-5,27439-12-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)00567-6

Reference yield: 79.0%

2'-hydroxy-3-phenylpropiophenone (3516-95-8) → FLAVONE (525-82-6,66585-04-4) + Flavanone (487-26-3) + 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7)

Guidance literature:

2'-hydroxy-3-phenylpropiophenone; With palladium(II) trifluoroacetate; copper diacetate; In dimethyl sulfoxide; at 100 ℃; for 15h; Inert atmosphere;

With hydrogenchloride; In water; dimethyl sulfoxide; ethyl acetate; at 100 ℃; for 24h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/d1ra01672e

Reference yield: 72.0%

1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1214-47-7) → FLAVONE (525-82-6,66585-04-4) + Flavanone (487-26-3)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; cesium acetate; In dimethyl sulfoxide; at 120 ℃; Solvent;

DOI:10.1021/acs.orglett.7b03325

upstream raw materials:

(2S,4S)-(+)-cis-4-hydroxyflavan

sulfuric acid

(S)-3,4-dihydro-2-phenyl-2H-1-benzopyran

(R)-3-Hydroxy-1-(2-hydroxy-phenyl)-3-phenyl-propan-1-one

Downstream raw materials:

2-phenyl-chroman-3,4-dione

Phenyl-2 oximino-3 chromanone-4

6-bromoflavone

2'-hydroxy-3-phenylpropiophenone

Refernces

• 1、 Nemeth, Istvan,Kiss-Szikszai, Attila,Gulacsi, Katalin,Mandi, Attila,Komaromi, Istvan,Kurtan, Tibor,Antus, Sandor. "Oxidation of enol acetate of flavanone with thallium(III) nitrate or phenyliodonium diacetate: A convenient new route to isoflavone and flavone". . p. 849 - 855. Retrieved 2014.
• 2、 Douglass et al.. "-". . p. 6372. Retrieved 1955.
• 3、 Gnyawali, Krishna,Kirinde Arachchige, Pandula T.,Yi, Chae S.. "Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines". supporting information. p. 218 - 222. Retrieved 2022/01/15.
• 4、 Chang, Chao-Che,Chen, Chao-Tsen,Chou, Pi-Tai,Huang, Chun-Hao,Li, Elise Y.,Liao, Yu-Chan,Liu, Yi-Hung,Liu, Zong-Ying,Meng, Fan-Yi,Wang, Chun-Hsiang. "Chapter Open for the Excited-State Intramolecular Thiol Proton Transfer in the Room-Temperature Solution". supporting information. p. 12715 - 12724. Retrieved 2021/08/30.