Scaled-up production of poacic acid, a plant-derived antifungal agent
Poacic acid, a decarboxylated product from 8–5-diferulic acid that is commonly found in monocot lignocellulosic hydrolysates, has been identified as a natural antifungal agent against economically significant fungi and oomycete plant pathogens. Starting from commercially available or monocot-derivable ferulic acid, a three-step synthetic procedure has been developed for the production of poacic acid needed for field testing in a controlled agricultural setting. First, ferulic acid was esterified to produce ethyl ferulate in 92% yield. Second, peroxidase-catalyzed free radical dehydrodimerization of ethyl ferulate produced crude diferulates, mainly 8–5-diferulate, in 91% yield. Finally, crystalline poacic acid was obtained in 25% yield via alkaline hydrolysis of the crude diferulates after purification by flash-column chromatography. Thus, this new procedure offers two key improvements relevant to large-scale production: 1) bubbling air through the reaction mixture in the second step to remove acetone greatly improves the recovery efficiency of the crude diferulates; and 2) telescoping minor impurities directly into the alkaline hydrolysis step eliminates the need for additional column purifications, thus reducing the overall cost of production and removing a major impediment to process scale-up.
- South China Univ. of Technology (SCUT), Guangzhou (China). State Key Lab. of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.
- Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.
- Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry, Dept. of Plant Pathology, Great Lakes Bioenergy Research Center and Wisconsin Energy Inst.; Yumanity Therapeutics, Cambridge, MA (United States)
- Publication Date:
- Grant/Contract Number:
- FC02-07ER64494; 178899
- Published Article
- Journal Name:
- Industrial Crops and Products
- Additional Journal Information:
- Journal Volume: 103; Journal Issue: C; Journal ID: ISSN 0926-6690
- Research Org:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org:
- USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
- Country of Publication:
- United States
- 60 APPLIED LIFE SCIENCES; 59 BASIC BIOLOGICAL SCIENCES; Lignocellulosic hydrolysates; Diferulates; Fungicide; Hydrolysis; Radical coupling
- OSTI Identifier:
- Alternate Identifier(s):
- OSTI ID: 1427248