Epoxybergamottin

Base Information

• Chemical Name: Epoxybergamottin
• CAS No.: 206978-14-5
• Molecular Formula: C21H22O5
• Molecular Weight: 354.39600
• European Community (EC) Number: 801-696-6
• Nikkaji Number: J1.176.314F
• Wikidata: Q3730718
• Metabolomics Workbench ID: 27910
• ChEMBL ID: CHEMBL1957147
• Mol file: 206978-14-5.mol

Synonyms:epoxybergamottin

Chemical Property of Epoxybergamottin

Chemical Property:

• Melting Point: 69-70 °C
• Boiling Point: 517.8±50.0 °C(Predicted)
• PSA: 65.11000
• Density: 1.210
• LogP: 4.82190
• Storage Temp.: ?20°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.14672380
• Heavy Atom Count: 26
• Complexity: 608

Purity/Quality:

98%Min ^*data from raw suppliers

6′,7′-Epoxybergamottin analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)CCC4C(O4)(C)C
• Isomeric SMILES: C/C(=C\COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/CCC4C(O4)(C)C

Technology Process of Epoxybergamottin

There total 7 articles about Epoxybergamottin 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: 88.0%

bergamottin (7380-40-7) → Epoxybergamottin (206978-14-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

bergamottin (482-46-2) → Epoxybergamottin (206978-14-5)

Guidance literature:

With pyridine; dihydrogen peroxide; methyltrioxorhenium(VII); In dichloromethane; at 25 ℃; for 4h; regioselective reaction;

DOI:10.3390/molecules181113754

Reference yield:

methanesulfonyl chloride (124-63-0) + methanesulfonic acid 1-(1-methanesulfonyloxy-1-methyl-ethyl)-4-methyl-6-(7-oxo-7H-furo[3,2-g]chromen-4-yloxy)-hex-4-enyl ester → Epoxybergamottin (206978-14-5)

Guidance literature:

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(02)00739-1

upstream raw materials:

bergamottin

methanesulfonyl chloride

trans-geranyl bromide

bergaptol

Downstream raw materials:

17,18-dihydroxybergamottin

6',7'-dihydroxybergamottin

Refernces

• 1、 Abulrob, Abedel-Nasser,Suller, Marc T.E.,Gumbleton, Mark,Simons, Claire,Russell, A. Denver. "Identification and biological evaluation of grapefruit oil components as potential novel efflux pump modulators in methicillin-resistant Staphylococcus aureus bacterial strains". . p. 3021 - 3027. Retrieved 2004.
• 2、 Row,Brown,Stachulski,Lennard. "Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4". . p. 1604 - 1610. Retrieved 2008/02/03.