Event Title
Cinnamic Acid Derivatives as Precursors to Antibiotic Activity
Faculty Mentor
Koushik Banerjee
Keywords
Koushik Banerjee
Abstract
Cinnamic acid derivatives (CADs) occur naturally in plants, coffee beans, fruits, vegetables and have some commercial applications in food-flavoring. Different substitutions on CADs display a wide range of cellular activities including antioxidative, antimicrobial, anti-inflammatory and enzyme inhibition. Here, we introduce a fundamental organic reaction , the Knoevenagel-Doebner modification, as a greener approach toward synthesis of CADs. Pyridine is typically used in this reaction but a safer solvent, triethylamine (TEA) is substituted for its lower environmental toxicity. A modified Knoevenagel-Doebner reflux of four aldehyde substrates afforded alpha-beta unsaturated carboxylic acids—4-chlorocinnamic acid, trans-3-methylcinnamic acid, (2E)-hex-2-enoic acid and (2E)-4-methylhept-2-enoic acid—with recoveries 72%, 91%, 29% and 81% respectively. The two aliphatic aldehydes, 2-methylpentanal and butanal, were chosen to test the limitations of the Knoevenagel-Doebner approach. Many cinnamic acid derivatives have not yet been studied for their pharmacological activities which broaden the variety of possibilities in unknown cinnamic acid effects.
Session Name:
Chemistry II
Start Date
4-4-2014 1:15 PM
End Date
4-4-2014 2:15 PM
Location
HSB 144
Cinnamic Acid Derivatives as Precursors to Antibiotic Activity
HSB 144
Cinnamic acid derivatives (CADs) occur naturally in plants, coffee beans, fruits, vegetables and have some commercial applications in food-flavoring. Different substitutions on CADs display a wide range of cellular activities including antioxidative, antimicrobial, anti-inflammatory and enzyme inhibition. Here, we introduce a fundamental organic reaction , the Knoevenagel-Doebner modification, as a greener approach toward synthesis of CADs. Pyridine is typically used in this reaction but a safer solvent, triethylamine (TEA) is substituted for its lower environmental toxicity. A modified Knoevenagel-Doebner reflux of four aldehyde substrates afforded alpha-beta unsaturated carboxylic acids—4-chlorocinnamic acid, trans-3-methylcinnamic acid, (2E)-hex-2-enoic acid and (2E)-4-methylhept-2-enoic acid—with recoveries 72%, 91%, 29% and 81% respectively. The two aliphatic aldehydes, 2-methylpentanal and butanal, were chosen to test the limitations of the Knoevenagel-Doebner approach. Many cinnamic acid derivatives have not yet been studied for their pharmacological activities which broaden the variety of possibilities in unknown cinnamic acid effects.