Xanthotoxol geranyl ether

Base Information

• Chemical Name: Xanthotoxol geranyl ether
• CAS No.: 71612-25-4
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.403
• European Community (EC) Number: 806-173-6,866-393-3
• DSSTox Substance ID: DTXSID001315117
• Nikkaji Number: J1.210.783H,J475.317H
• Wikidata: Q3599893
• Metabolomics Workbench ID: 48486
• ChEMBL ID: CHEMBL1412710
• Mol file: 71612-25-4.mol

Synonyms:5-geranoxypsoralen;8-geranyloxypsoralen;bergamottin

Chemical Property of Xanthotoxol geranyl ether

Chemical Property:

• Vapor Pressure: 2.85E-10mmHg at 25°C
• Boiling Point: 503.7°Cat760mmHg
• Flash Point: 258.4°C
• Density: 1.153g/cm³
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 338.15180918
• Heavy Atom Count: 25
• Complexity: 570

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C)C
• Isomeric SMILES: CC(=CCC/C(=C/COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)/C)C

Technology Process of Xanthotoxol geranyl ether

There total 3 articles about Xanthotoxol geranyl ether 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: 82.0%

trans-geranyl bromide (6138-90-5) + 8-hydroxypsoralen (2009-24-7) → 8-geranyloxypsoralen (71612-25-4,7437-55-0)

Guidance literature:

With potassium carbonate; In acetone; for 17h; Heating;

DOI:10.1016/j.bmc.2006.01.046

Reference yield:

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (298-81-7) → 8-geranyloxypsoralen (71612-25-4,7437-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / BBr₃ / CH₂Cl₂ / 4 h / 20 °C

2: 82 percent / K₂CO₃ / acetone / 17 h / Heating

With boron tribromide; potassium carbonate; In dichloromethane; acetone;

DOI:10.1016/j.bmc.2006.01.046

Reference yield:

→ 8-geranyloxypsoralen (71612-25-4)

Guidance literature:

Xanthotoxol , Geranylbromid ;

DOI:10.1016/S0040-4020(01)82304-8

upstream raw materials:

trans-geranyl bromide

8-hydroxypsoralen

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one

Downstream raw materials:

Dihydro-8-hydroxypsoralen

8-hydroxypsoralen

6',7'-Epoxy-8-geranyloxypsoralen