Comparison of Sinapic acid Derivative Chain Length on Initial Rate of Radical Scavenging with DPPH Assay
Format
Poster Presentation
Faculty Mentor Name
Andreas H. Franz
Faculty Mentor Department
Chemistry
Graduate Student Mentor Name
Cate Simmermaker
Graduate Student Mentor Department
Chemistry
Abstract/Artist Statement
Sinapic acid is a natural hydroxycinnamic acid found in fruits and vegetables. Among other positive health benefits this compound has been considered for, it is a well characterized free radical scavenger. The mitigation of biological free radicals is linked to reduced risk of atherosclerosis, vision loss and cancer. Characteristics of an effective radical scavenger include relatively stable radical accommodation. Derivatives with the ability to extend the number of resonance structures of the primary scaffold can have a stabilizing effect, allowing for more efficient radical scavenging. The phenolic structure of sinapic acid is stabilized by the ortho methoxy groups to the hydroxy; this gives an enhanced stability compared to similar compounds like p-coumaric and ferulic acid. The derivatives prepared to compare to previous recorded data results of glycine and aspartic acid additions include amino acid derivative portions of β-alanine and glutamic acid, which were synthesized using an established pathway of acetylation > chlorination > amidation > deprotection. Both sets of derivative structures are the same, apart from a single carbon atom, secondly the additional carboxylic acid group on the Asp and Glu derivatives can be directly compared with the β-Ala and Gly derivatives. Effectiveness and activity as a radical scavenger were characterized with a DPPH, 2,2-diphenyl-1-picrylhydrazyl, assay. [J. Xie and K. M. Schaich (2014) J. Agric. Food Chem] In this assay a stable free radical is reduced by the compound of interest, DPPH in MeOH is converted from a purple to yellow which can be quantitatively analyzed by UV-Vis at 515 nm. The initial reaction rate is linked to the mechanism of reduction. In this work, we attempt to identify the overall capacity for reduction and mechanism of action affected by the derivative chain length. The major difference in rate of initial reaction was observed in the additional carboxylic acids.
Location
Virtual
Start Date
25-4-2020 1:00 PM
End Date
25-4-2020 3:00 PM
Comparison of Sinapic acid Derivative Chain Length on Initial Rate of Radical Scavenging with DPPH Assay
Virtual
Sinapic acid is a natural hydroxycinnamic acid found in fruits and vegetables. Among other positive health benefits this compound has been considered for, it is a well characterized free radical scavenger. The mitigation of biological free radicals is linked to reduced risk of atherosclerosis, vision loss and cancer. Characteristics of an effective radical scavenger include relatively stable radical accommodation. Derivatives with the ability to extend the number of resonance structures of the primary scaffold can have a stabilizing effect, allowing for more efficient radical scavenging. The phenolic structure of sinapic acid is stabilized by the ortho methoxy groups to the hydroxy; this gives an enhanced stability compared to similar compounds like p-coumaric and ferulic acid. The derivatives prepared to compare to previous recorded data results of glycine and aspartic acid additions include amino acid derivative portions of β-alanine and glutamic acid, which were synthesized using an established pathway of acetylation > chlorination > amidation > deprotection. Both sets of derivative structures are the same, apart from a single carbon atom, secondly the additional carboxylic acid group on the Asp and Glu derivatives can be directly compared with the β-Ala and Gly derivatives. Effectiveness and activity as a radical scavenger were characterized with a DPPH, 2,2-diphenyl-1-picrylhydrazyl, assay. [J. Xie and K. M. Schaich (2014) J. Agric. Food Chem] In this assay a stable free radical is reduced by the compound of interest, DPPH in MeOH is converted from a purple to yellow which can be quantitatively analyzed by UV-Vis at 515 nm. The initial reaction rate is linked to the mechanism of reduction. In this work, we attempt to identify the overall capacity for reduction and mechanism of action affected by the derivative chain length. The major difference in rate of initial reaction was observed in the additional carboxylic acids.