Bavachalcone

Base Information

• Chemical Name: Bavachalcone
• CAS No.: 28448-85-3
• Molecular Formula: C20H20 O4
• Molecular Weight: 324.376
• DSSTox Substance ID: DTXSID401317977
• Nikkaji Number: J16.995A,J3.588.291J
• Metabolomics Workbench ID: 26522
• ChEMBL ID: CHEMBL464428
• Mol file: 28448-85-3.mol

Synonyms:bavachalcone

Chemical Property of Bavachalcone

Chemical Property:

• Vapor Pressure: 1.09E-12mmHg at 25°C
• Melting Point: 168-169℃
• Boiling Point: 549.6oC at 760 mmHg
• PKA: 7.58±0.50(Predicted)
• Flash Point: 300.2oC
• PSA: 77.76000
• Density: 1.243g/cm3
• LogP: 4.20820
• 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:

≥98% ^*data from raw suppliers

Bavachalcone 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=CC(=C(C=C1O)O)C(=O)C=CC2=CC=C(C=C2)O)C
• Isomeric SMILES: CC(=CCC1=CC(=C(C=C1O)O)C(=O)/C=C/C2=CC=C(C=C2)O)C
• General Description: Bavachalcone is a prenylated chalcone belonging to the flavonoid subclass, known for its diverse biological and pharmacological activities. It is structurally characterized by a chalcone backbone with hydroxyl and prenyl (3-methyl-2-butenyl) substitutions, contributing to its bioactive properties. Bavachalcone has been synthesized efficiently through regiospecific iodination and Suzuki coupling reactions, demonstrating improved yield and regiochemical control compared to traditional methods.

Technology Process of Bavachalcone

There total 15 articles about Bavachalcone 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: 75.0%

(E)-1-(2,4-bis(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1544322-43-1) → buroussochalcone B (28448-85-3)

Guidance literature:

With hydrogenchloride; methanol; In water; at 0 - 50 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.12.044

Reference yield: 61.0%

(E)-1-(2-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (128961-13-7) → (+/-)-bavachin (78316-27-5,19879-32-4) + buroussochalcone B (28448-85-3)

Guidance literature:

With carbon tetrabromide; In methanol; for 8h; Reflux;

DOI:10.1016/j.tet.2011.04.104

Reference yield: 22.0%

2',4,4'-trihydroxychalcone (13745-20-5) + prenyl bromide (870-63-3) → buroussochalcone B (28448-85-3) + isobavachalcone (54676-49-2,20784-50-3)

Guidance literature:

With magnesium succinate; In N,N-dimethyl-formamide; at 60 ℃; for 16h; Solvent; regioselective reaction; Inert atmosphere;

DOI:10.1039/d1ob02228h

upstream raw materials:

4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone

1-(2-hydroxy-4-methoxyphenyl)ethanone

4-methoxymethoxy-benzaldehyde

1-(4-methoxy-2-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one

Downstream raw materials:

1-(7-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)propenone

(E)-1-(2,4-dimethoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-methoxyphenyl)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.

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