Xanthoangelol

Base Information

• Chemical Name: Xanthoangelol
• CAS No.: 62949-76-2
• Molecular Formula: C25H28O4
• Molecular Weight: 392.495
• UNII: 91D4GN26Z1
• DSSTox Substance ID: DTXSID301317693
• Nikkaji Number: J20.204E,J2.069.001A
• Metabolomics Workbench ID: 26530
• ChEMBL ID: CHEMBL494083
• Mol file: 62949-76-2.mol

Synonyms:xanthoangelol

Chemical Property of Xanthoangelol

Chemical Property:

• Vapor Pressure: 2.85E-15mmHg at 25°C
• Melting Point: 141-143 °C
• Boiling Point: 605.8°C at 760 mmHg
• PKA: 7.57±0.50(Predicted)
• Flash Point: 334.2°C
• PSA: 77.76000
• Density: 1.165g/cm³
• LogP: 5.93470
• XLogP3: 7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 392.19875937
• Heavy Atom Count: 29
• Complexity: 606

Purity/Quality:

≥98% ^*data from raw suppliers

Xanthoangelol 98.36% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)/C)C
• General Description: Xanthoangelol is a geranylated chalcone natural product belonging to the flavonoid subclass, known for its diverse biological and pharmacological activities. It is structurally characterized as 3-geranyl-2,4,4'-trihydroxychalcone or 2',4,4'-trihydroxy-3'-geranylchalcone. Xanthoangelol was synthesized efficiently in this study using regiospecific iodination and Suzuki coupling reactions, demonstrating improved yield and regiochemical control compared to previous methods.

Technology Process of Xanthoangelol

There total 12 articles about Xanthoangelol 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: 77.0%

4,4'-bis(methoxymethoxy)-3'-geranyl-2'-hydroxychalcone (1314539-28-0) → xanthoangelol (62949-76-2)

Guidance literature:

With carbon tetrabromide; In isopropyl alcohol; for 5h; Reflux;

DOI:10.1016/j.tet.2011.04.104

Reference yield: 75.0%

(2E)-1-[3-geranyl-2-hydroxy-4-(methoxymethoxy)phenyl]-3-{4-{[2-(trimethylsilyl)ethoxy]methoxy}-phenyl}prop-2-en-1-one (1229515-77-8) → xanthoangelol (62949-76-2)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 10h; Inert atmosphere;

DOI:10.1002/hlca.200900251

Reference yield: 72.0%

(E)-1-(3-((E)-3,7-dimethylocta-2,6-dien-1-yl)-2,4-bis(methoxymethoxy)phenyl)-3-(4-(methoxymethoxy)phenyl)prop-2-en-1-one (1544322-63-5) → xanthoangelol (62949-76-2)

Guidance literature:

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

DOI:10.1016/j.tetlet.2013.12.044

upstream raw materials:

(2E)-1-[3-geranyl-2-hydroxy-4-(methoxymethoxy)phenyl]-3-{4-{[2-(trimethylsilyl)ethoxy]methoxy}-phenyl}prop-2-en-1-one

2',4'-dihydroxy-4-acetophenone

2'-gerenyloxy-4'-(methoxymethoxy)acetophenone

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

Downstream raw materials:

4,2',4'-triacetoxy-3'-geranylchalcone

(2E)-1-[5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-1-benzopyran-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.