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Synthesis and Characterization of a Novel Phenolic Lipid for Use as Potential Lipophilic Antioxidant and as a Prodrug of Butyric Acid.

Journal of oleo science (2015-07-17)
Shiva Shanker Kaki, Konda Reddy Kunduru, Sanjit Kanjilal, Rachapudi Badari Narayana Prasad
ABSTRACT

Ferulic acid was modified to produce a novel phenolipid containing butyl chains. Ferulic acid was esterified with butanol to produce butyl ferulate which was further dihydroxylated followed by esterification with butyric anhydride to produce the phenolipid containing butyric acid. IR, NMR and MS techniques confirmed the structure of the synthesized structured lipophilic phenolic compound. The synthesized compound was tested for in vitro antioxidant and antimicrobial activities. The produced phenolipid showed moderate antioxidant activity in DPPH (2, 2-diphenyl-1-picrylhydrazyl) radical scavenging assay but in linoleic acid oxidation method, it exhibited good activity compared with the parent compound and the reference compounds. The prepared derivative could find applications as antioxidant in lipophilic systems and also as a potential prodrug of butyric acid. It also showed antibacterial effect against the four bacterial strains studied. The drug-likeness properties of the prepared molecule calculated were in the acceptable ranges according to Lipinski's rule of 5 and suggest that it has potential to cross the blood-brain barrier.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Butanol, anhydrous, 99.8%
Sigma-Aldrich
4-(Dimethylamino)pyridine, ReagentPlus®, ≥99%
Sigma-Aldrich
tert-Butyldimethylsilyl chloride, reagent grade, 97%
Sigma-Aldrich
1-Butanol, for molecular biology, ≥99%
Sigma-Aldrich
trans-Ferulic acid, 99%
Sigma-Aldrich
2-Aminopyridine, ≥99%
Sigma-Aldrich
Butyl alcohol, natural, ≥99.5%, FCC, FG
Sigma-Aldrich
trans-Ferulic acid, ≥99%
Sigma-Aldrich
2-Aminopyridine, 99%
Sigma-Aldrich
Potassium bromide, BioXtra, ≥99.0%
Sigma-Aldrich
Potassium bromide, BioUltra, ≥99.5% (AT)
Sigma-Aldrich
Butyric anhydride, 98%
Sigma-Aldrich
Butyric anhydride, 98%
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.999% trace metals basis
Sigma-Aldrich
tert-Butylchlorodimethylsilane solution, 50 wt. % in toluene
Sigma-Aldrich
Potassium bromide, anhydrous, powder, 99.95% trace metals basis
Sigma-Aldrich
tert-Butyldimethylsilyl chloride solution, 1.0 M in THF
Sigma-Aldrich
tert-Butyldimethylsilyl chloride solution, 1.0 M in methylene chloride
Supelco
1-Butanol, suitable for HPLC, 99.8%