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

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

• 1、 Wang, Haomeng,Yan, Zhihong,Lei, Yanan,Sheng, Kai,Yao, Qingwei,Lu, Kui,Yu, Peng. "Concise synthesis of prenylated and geranylated chalcone natural products by regiospecific iodination and Suzuki coupling reactions". . p. 897 - 899. Retrieved 2014/02/14.
• 2、 Sugamoto, Kazuhiro,Matsusita, Yoh-Ichi,Matsui, Kana,Kurogi, Chiaki,Matsui, Takanao. "Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei". . p. 5346 - 5359. Retrieved 2011/08/04.