5-Geranyloxy-7-methoxycoumarin

Base Information

• Chemical Name: 5-Geranyloxy-7-methoxycoumarin
• CAS No.: 7380-39-4
• Molecular Formula: C20H24 O4
• Molecular Weight: 328.408
• UNII: 39A7K6NN3W
• DSSTox Substance ID: DTXSID001045382
• Nikkaji Number: J475.318F,J573.344H
• Wikipedia: 5-Geranyloxy-7-methoxycoumarin
• Wikidata: Q13461252
• Metabolomics Workbench ID: 45810
• ChEMBL ID: CHEMBL4176013
• Mol file: 7380-39-4.mol

Synonyms:5-geranyloxy-7-methoxycoumarin

Chemical Property of 5-Geranyloxy-7-methoxycoumarin

Chemical Property:

• Vapor Pressure: 1.22E-09mmHg at 25°C
• Melting Point: 86-88°C
• Boiling Point: 487.1°C at 760 mmHg
• Flash Point: 213.2°C
• PSA: 48.67000
• Density: 1.092g/cm³
• LogP: 4.87310
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 514

Purity/Quality:

98%Min ^*data from raw suppliers

5-Geranyloxy-7-methoxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCOC1=CC(=CC2=C1C=CC(=O)O2)OC)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COC1=CC(=CC2=C1C=CC(=O)O2)OC)/C)C

Technology Process of 5-Geranyloxy-7-methoxycoumarin

There total 2 articles about 5-Geranyloxy-7-methoxycoumarin 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-geranyloxy-7-hydroxycoumarin (185463-71-2) → 5-geranyloxy-7-methoxycoumarin (7380-39-4)

Guidance literature:

In methanol; Yield given; Ambient temperature;

DOI:10.1248/cpb.44.2231

Reference yield:

trans-geranyl bromide (6138-90-5) + 5,7-dihydroxycoumarin 7-methyl ether (23053-61-4) → 5-geranyloxy-7-methoxycoumarin (7380-39-4)

Guidance literature:

DOI:10.1016/j.ejmech.2018.04.051

Reference yield:

5-geranyloxy-7-methoxycoumarin (7380-39-4) → Limettin (487-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; acetic acid

2: methanol; diethyl ether

With methanol; diethyl ether; sulfuric acid; acetic acid;

DOI:10.1021/ja01570a049

upstream raw materials:

diazomethane

5-geranyloxy-7-hydroxycoumarin

trans-geranyl bromide

5,7-dihydroxycoumarin 7-methyl ether

Downstream raw materials:

5,7-dihydroxycoumarin 7-methyl ether

Limettin

Refernces

• 1、 Fiorito, Serena,Epifano, Francesco,Preziuso, Francesca,Cacciatore, Ivana,di Stefano, Antonio,Taddeo, Vito Alessandro,de Medina, Philippe,Genovese, Salvatore. "Natural oxyprenylated coumarins are modulators of melanogenesis". . p. 274 - 282. Retrieved 2018/05/14.