Isobavachalcone

Base Information

• Chemical Name: Isobavachalcone
• CAS No.: 20784-50-3
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• UNII: ZWO2SC993A
• ChEMBL ID: CHEMBL253467
• DSSTox Substance ID: DTXSID601317123
• Metabolomics Workbench ID: 26516
• Nikkaji Number: J1.041.729E,J19.902H
• Wikidata: Q27103503
• Mol file: 20784-50-3.mol

Synonyms:isobavachalcone

Chemical Property of Isobavachalcone

Chemical Property:

• Vapor Pressure: 1.15E-12mmHg at 25°C
• Melting Point: 156.8-157.8 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 549°Cat760mmHg
• PKA: 7.99±0.40(Predicted)
• Flash Point: 299.9°C
• PSA: 77.76000
• Density: 1.243g/cm³
• LogP: 4.20820
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Soluble in DMSO
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 324.13615911
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Isobavachalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)C
• Isomeric SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
• General Description: Isobavachalcone is a prenylated chalcone natural product belonging to the flavonoid subclass, recognized for its diverse biological and pharmacological activities. It was synthesized in this study through an efficient method involving regiospecific iodination and Suzuki coupling reactions, which improved yield and regiochemical control compared to previous approaches. The compound, along with related chalcones, demonstrates potential as a bioactive molecule, though further exploration of its specific properties and applications is warranted.

Technology Process of Isobavachalcone

There total 18 articles about Isobavachalcone 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: 89.0%

(E)-1-(2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1449202-18-9) → isobavachalcone (54676-49-2,20784-50-3) + 2',4-dihydroxy-4'-methoxymethoxy-3'-prenylchalcone

Guidance literature:

With hydrogenchloride; In methanol; water; for 3h; Reflux;

DOI:10.1002/ejoc.201201063

Reference yield: 75.0%

(E)-1-(2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1449202-18-9) → isobavachalcone (54676-49-2,20784-50-3)

Guidance literature:

With hydrogenchloride; methanol; In water; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.12.044

Reference yield: 72.0%

4,4'-bis(methoxymethoxy)-2'-hydroxyl-3'-prenylchalcone → isobavachalcone (54676-49-2,20784-50-3)

Guidance literature:

With hydrogenchloride; In methanol; water; for 0.5h; Reflux;

DOI:10.1016/j.tet.2011.04.104

upstream raw materials:

2',4'-dihydroxy-4-acetophenone

2'-prenyloxy-4'-methoxymethoxyacetophenone

4,4'-bis(methoxymethoxy)-2'-prenyloxychalcone

4-methoxymethoxy-benzaldehyde

Downstream raw materials:

(E)-1-(5-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Refernces

Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions

10.1016/j.tetlet.2013.12.044

The research aims to develop an efficient synthetic method for prenylated and geranylated chalcone natural products, which exhibit various biological and pharmacological activities. The study employs regiospecific iodination and Suzuki coupling reactions as key steps to synthesize four natural chalcones: isobavachalcone (1), bavachalcone (2), xanthoangelol (3), and 2,4',4-trihydroxy-5'-geranylchalcone (isoxanthoangelol, 4). The researchers used NIS (N-iodosuccinimide) for iodination and palladium catalysts along with bases like Cs2CO3 for the Suzuki coupling. The new synthetic strategy significantly improves the overall yields of the first three chalcones compared to previously reported methods, and it also achieves the first total synthesis of isoxanthoangelol (4) with a 36% overall yield. The study concludes that this approach offers better regiochemical control and higher efficiency in synthesizing these chalcone natural products, and the authors are exploring its extension to other C-alkyl substituted flavonoids and their derivatives. Isobavachalcone (1), bavachalcone (2), and xanthoangelol (3) are three natural chalcones containing prenyl or geranyl groups that were synthesized. These compounds are part of the flavonoid subclass and are known for their various biological and pharmacological activities.