57457-99-5

Basic information

• Product Name: 2-Epi-3a-epiburchellin
• Synonyms: 2-Epi-3a-epiburchellin;(2R,3S,3aS)-2-(1,3-Benzodioxol-5-yl)-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propen-1-yl)-6(2H)-benzofuranone
• CAS NO: 57457-99-5
• Molecular Formula: C20H20O5
• Molecular Weight: 340.3698
• Mol File: 57457-99-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 491.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-Epi-3a-epiburchellin(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Epi-3a-epiburchellin(57457-99-5)
• EPA Substance Registry System: 2-Epi-3a-epiburchellin(57457-99-5)

Safety Data

• Hazardous Substances Data: 57457-99-5(Hazardous Substances Data)

Usage

General Description

2-Epi-3a-epiburchellin is a chemical compound that belongs to the class of 3a-epiburchellins. It is a potent inhibitor of diacylglycerol acyltransferase (DGAT) and has shown potential anti-obesity and anti-diabetic effects in animal studies. 2-Epi-3a-epiburchellin is naturally found in the leaves and stems of the Ocimum tenuiflorum plant, also known as holy basil. Research has shown that 2-Epi-3a-epiburchellin may have therapeutic potential in the treatment of metabolic disorders and could be used as a natural remedy for obesity and diabetes. Its pharmacological properties make it a promising candidate for further development as a potential drug for these conditions.

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Relevant articles and documents

Burchellin and its stereoisomers: Total synthesis, structural elucidation and antiviral activity

Burchellin and its analogues are a class of neolignan natural products containing a rare core with three contiguous stereogenic centers. In previous reports, racemic burchellin was synthesized without accessing each of the enantiomers. In this paper, a concise and efficient total synthetic route to divergently access the enantiomers of burchellin and those of its 1′-epi-diastereoisomer over six steps for each is disclosed, where each of the enantiomers was obtained by preparative chiral phase HPLC purification. The key steps include the construction of a 2,3-dihydrobenzofuran moiety by two Claisen rearrangements and a one-step rearrangement/cyclization and subsequent tandem ester hydrolysis/oxy-Cope rearrangement/methylation to furnish the basic skeleton of burchellin. The structures and absolute configurations of the four stereoisomers were determined using spectroscopic data analyses and comparison of experimental and calculated electronic circular dichroism data. These stereoisomers were found to have potent antiviral effects against coxsackie virus B3, and is the first time that bioactivity has been reported for these compounds. This journal is