Isoflavone

Base Information

• Chemical Name: Isoflavone
• CAS No.: 574-12-9
• Molecular Formula: C15H10O2
• Molecular Weight: 222.243
• Hs Code.: 2914399090
• European Community (EC) Number: 611-522-9
• NSC Number: 135405
• UNII: OVO2KUW8H8
• DSSTox Substance ID: DTXSID90205986
• Nikkaji Number: J46.301I
• Wikidata: Q27102918
• NCI Thesaurus Code: C599
• ChEMBL ID: CHEMBL366460
• Mol file: 574-12-9.mol

Synonyms:3 Benzylchroman 4 One;3 Benzylchroman 4 Ones;3 Benzylidene 4 Chromanone;3 Benzylidene 4 Chromanones;3-Benzylchroman-4-One;3-Benzylchroman-4-Ones;3-Benzylidene-4-Chromanone;3-Benzylidene-4-Chromanones;Derivative, Isoflavone;Derivatives, Isoflavone;Homoisoflavone;Homoisoflavones;Isoflavone;Isoflavone Derivative;Isoflavone Derivatives;Isoflavones

Chemical Property of Isoflavone

Chemical Property:

• Vapor Pressure: 1.41E-05mmHg at 25°C
• Melting Point: 150oC
• Refractive Index: 1.635
• Boiling Point: 367 °C at 760 mmHg
• Flash Point: 171.1 °C
• PSA: 30.21000
• Density: 1.239 g/cm³
• LogP: 3.46000
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.068079557
• Heavy Atom Count: 17
• Complexity: 326

Purity/Quality:

40% ^*data from raw suppliers

Isoflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=COC3=CC=CC=C3C2=O
• Recent ClinicalTrials: Effect of Soy on Cognition and Hot Flashes in Men With Prostate Cancer Undergoing Testosterone Suppression Therapy
• Recent NIPH Clinical Trials: The effect of isoflavones in endometriotic pain
• General Description: Isoflavone, also known as 3-phenyl-4-chromone or 3-phenylchromone, is a biologically active compound with applications in pharmaceutical chemistry. It serves as a key precursor in the synthesis of fused heteroaromatic compounds like 3,4-diphenylimidazo[1,5-a]pyrimidines under microwave-assisted conditions, demonstrating regioselectivity and moderate to good yields. Additionally, isoflavone analogues derived from *Dalbergia oliveri* exhibit cytotoxic effects against leukemia cells and inhibit fungal growth, though they lack antibacterial activity. These properties highlight its potential in drug development and medicinal research.

Technology Process of Isoflavone

There total 79 articles about Isoflavone 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: 98.0%

2-hydroxy-deoxybenzoin (2491-31-8) → isoflavone (574-12-9)

Guidance literature:

With methanesulfonyl chloride; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 1h;

Reference yield: 97.0%

isoflavanone (97904-75-1,4737-27-3,143358-19-4,143358-34-3) → isoflavone (574-12-9)

Guidance literature:

With sulfuric acid; iodine; dimethyl sulfoxide; at 100 ℃; for 0.5h;

Reference yield: 96.0%

3-(2-bromophenyl)-3-oxo-2-phenylpropanal (1258792-30-1) → isoflavone (574-12-9)

Guidance literature:

With 2-Picolinic acid; copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 135 - 140 ℃; for 20h; Inert atmosphere;

DOI:10.1002/hlca.201000400

upstream raw materials:

3-(2-methoxy-phenyl)-3-oxo-2-phenyl-propionaldehyde

3-phenyl-3-phenylthio-2,3-dihydro-(4H)-benzopyran-4-one

lead(IV) tetraacetate

acetic acid

Downstream raw materials:

3-phenyl-2H-benzopyran

2,3-epoxyisoflavone

3-cyano-6-(2-hydroxylphenyl)-5-phenylpyridine-2(1H)-thione

2-methyl-6-phenyl-7-(2-hydroxylphenyl)pyrazolo[1,5-a]pyrimidine

Refernces

Microwave irradiation for accelerating synthesis of diarylimidizo[1,5-a] pyrimidine based on isoflavones

10.1002/cjoc.201100405

The research aimed to develop an efficient and regioselective method for the synthesis of 3,4-diphenylimidazo[1,5-a]pyrimidines, which are important fused heteroaromatic compounds with potential biological activities. The study utilized microwave irradiation to accelerate the cyclocondensation of isoflavones with 5-amino-1H-imidazole-4-carboxamide in the presence of sodium hydroxide, resulting in the formation of the target compounds in good to moderate yields. The optimized conditions involved the use of DMF as a solvent and sodium hydroxide as a base, with a molar ratio of 1a (isoflavone) to 2 (5-amino-1H-imidazole-4-carboxamide) to base of 1:1.6:3. The method was found to be suitable for a variety of structurally divergent isoflavones, leading to the synthesis of 3,4-diphenylimidazo[1,5-a]pyrimidines with yields ranging from 58% to 88%. The research concluded that this approach is an efficient and regioselective method for constructing fused 3,4-diphenylimidazo[1,5-a]pyrimidines derivatives, offering a valuable contribution to the field of pharmaceutical chemistry.

Synthesis and biological evaluation of isoflavone analogues from Dalbergia oliveri

10.1016/j.tet.2007.10.030

The research focuses on the synthesis and biological evaluation of isoflavone analogues derived from Dalbergia oliveri, a plant used in traditional Thai medicine for treating chronic ulcers. The purpose of the study was to investigate the potential of these compounds as mitosis inhibitor agents, specifically their cytotoxic effects against leukemia cell lines, their ability to inhibit microtubule assembly, and their antimicrobial activity. The researchers synthesized mucronulatol 1, violanone 2, and isoflavone 3 using an aryllead-mediated coupling reaction, which involved organolead reagents. The conclusions drawn from the study were that mucronulatol 1 exhibited significant cytotoxicity against the HBL100 leukemia cell line with an IC50 value of 5.7 mM, while all compounds modestly inhibited microtubule assembly, independent of their cytotoxic abilities. However, none of the compounds showed antibacterial activity, but were potent inhibitors of Fusarium oxysporum, a phytopathogenic fungal growth. The chemicals used in the synthesis process included 3-phenylthio-chroman-4-one, mucronulatol, violanone, and various reagents such as lead tetraacetate, tin compounds, and palladium on charcoal, among others.