Synthesis of 2-O-(4-Coumaroyl)-3-(4-hydroxyphenyl)lactic Acid, an Important Intermediate of Rosmarinic Acid Biosynthesis.

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  • MATSUNO Michiyo
    Graduate School of Pharmaceutical Sciences, Nagoya City University
  • NAGATSU Akito
    Graduate School of Pharmaceutical Sciences, Nagoya City University
  • OGIHARA Yukio
    Graduate School of Pharmaceutical Sciences, Nagoya City University
  • MIZUKAMI Hajime
    Graduate School of Pharmaceutical Sciences, Nagoya City University

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A simple method to synthesize (±)-2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactic acid (1), a key intermediate in rosmarinic acid biosynthesis in higher plant cells, was established by condensation of protected 4-coumaric acid and (±)-3-(4-hydroxyphenyl)lactic acid followed by deprotection. A stable supply of 1 thus attained will lead to biochemical and molecular biological characterization of later steps of rosmarinic acid biosynthesis.

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