A new and efficient synthesis of 6-O-methylscutellarein, the major metabolite of the natural medicine scutellarin

Molecules. 2015 Jun 2;20(6):10184-91. doi: 10.3390/molecules200610184.

Abstract

In this paper, a new and efficient synthesis of 6-O-methylscutellarein (3), the major metabolite of the natural medicine scutellarin, is reported. Two hydroxyl groups at C-4' and C-7 in 2 were selectively protected by chloromethyl methyl ether after the reaction conditions were optimized, then 6-O-methyl-scutellarein (3) was produced in high yield after methylation of the hydroxyl group at C-6 and subsequent deprotection of the two methyl ether groups.

Keywords: 6-O-methylscutellarein; metabolite; scutellarein; scutellarin; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apigenin / chemistry*
  • Biotransformation
  • Flavones / chemical synthesis*
  • Glucuronates / chemistry*
  • Humans
  • Methyl Ethers / chemistry
  • Methylation
  • Solutions

Substances

  • 6-O-methylscutellarein
  • Flavones
  • Glucuronates
  • Methyl Ethers
  • Solutions
  • scutellarin
  • chloromethyl methyl ether
  • Apigenin
  • scutellarein