Xanthotoxol geranyl ether

Base Information

• Chemical Name: Xanthotoxol geranyl ether
• CAS No.: 7437-55-0
• 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: 7437-55-0.mol

Synonyms:5-geranoxypsoralen;8-geranyloxypsoralen;bergamottin

Chemical Property of Xanthotoxol geranyl ether

Chemical Property:

• Melting Point: 53-54 °C
• Boiling Point: 503.7±50.0 °C(Predicted)
• PSA: 52.58000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 5.61070
• Storage Temp.: 2-8°C
• 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:

99%, ^*data from raw suppliers

8-Geranopsoralen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 313632
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36-37

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
• Uses: 8-Geranyloxypsoralen is an anti-bacterial substances that were active against oral bacteria that causes dental caries and periodontitis such as Streptococcus mutans, Prevotella intermedia, and Porphyromonas gingivalis. Also, it is an β-secretase inhibitor.

Technology Process of Xanthotoxol geranyl ether

There total 2 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 (71612-25-4,7437-55-0) → Dihydro-8-hydroxypsoralen (68123-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / hexafluoroacetone trihydrate; H₂O₂; Na₂HPO₄ / CH₂Cl₂; H₂O / 18 h / 20 °C

2: camphorsulfonic acid / methanol

3: 77 percent / Et₃N; formic acid / Pd/C / acetone / 0.25 h

With disodium hydrogenphosphate; formic acid; camphor-10-sulfonic acid; dihydrogen peroxide; triethylamine; Hexafluoroacetone; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;

DOI:10.1016/j.bmc.2006.01.046

upstream raw materials:

trans-geranyl bromide

8-hydroxypsoralen

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

Downstream raw materials:

6',7'-Epoxy-8-geranyloxypsoralen

8-hydroxypsoralen

Dihydro-8-hydroxypsoralen

Refernces

• 1、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor". supporting information; experimental part. p. 784 - 788. Retrieved 2012/03/22.