Efficient Synthesis of Pinoresinol, an Important Lignin Dimeric Model Compound

Journal Article · Tue Mar 30 04:00:00 UTC 2021 · Frontiers in Energy Research

DOI: https://doi.org/10.3389/fenrg.2021.640337 · OSTI ID:2325263

Yue, Fengxia; Lan, Wu; Zhang, Liming; Lu, Fachuang; Sun, Runcang; Ralph, John

Pinoresinol is a high-value monolignol-derived lignan used in plant defense and with human health-supporting effects. The synthetic yield and isolation efficiency of racemic pinoresinol from coniferyl alcohol by conventional radical coupling methods is sub-optimal. In this work, a facile and efficient synthetic approach was developed to synthesize pinoresinol with much higher yield. By using 5-bromoconiferyl alcohol, which was synthesized in high yield from 5-bromovanillin, to make 5,5′-bromopinoresinol via a peroxidase-mediated radical coupling reaction takes advantage of the smaller variety of radical coupling products from the 5-substituted monolignol, producing simpler product mixtures from which 5,5′-bromopinoresinol may be readily crystalized with good yield (total yield of 44.1% by NMR; isolated crystalline yield of 24.6%). Hydro-debromination of the crystalline 5,5′-bromopinoresinol to pinoresinol was essentially quantitative. Gram quantities of pinoresinol were conveniently synthesized by using this approach. This simple alternative pathway to make pinoresinol will impact pinoresinol-related research including structural characterization and modification of lignins, as well as clinical applications of pinoresinol and its derivatives.

• Sponsoring Organization: USDOE
• OSTI ID: 2325263
• Journal Information: Frontiers in Energy Research, Journal Name: Frontiers in Energy Research Vol. 9; ISSN 2296-598X
• Publisher: Frontiers Media SACopyright Statement
• Country of Publication: Switzerland
• Language: English