Suppressive Effect of Alkyl Ferulate on the Oxidation of Linoleic Acid

Xu, Fang; Shima, Masasuke; Kadota, Megumi; Tsuno, Takuo; Adachi, Shuji

doi:10.1271/bbb.70.457

Cited by 23 publications

(19 citation statements)

References 13 publications

(11 reference statements)

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“…The hydrophobic derivatives, alkyl ferulates, have a higher antioxidative activity than unmodified ferulic acid for the prevention of oxidation of linoleic acid in a bulk system (Fang et al 2006). The enzymatic synthesis of hydrophilic and hydrophobic derivatives of ferulic acid has been investigated (Stamatis et al 2001) in order to increase their water-or oil-solubility as well as derivatives of other phenolic acids (Buisma et al 1998).…”

Section: Introductionmentioning

confidence: 99%

Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature

et al. 2006

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1-Pentyl, 1-hexyl and 1-heptyl ferulates were continuously synthesized at 60-90 degrees C using a reactor system in which a column packed with ferulic acid powders and another column packed with immobilized Candida antarctica lipase particles were connected in series. Conversions greater than 0.9 were achieved for the synthesis of the 1-hexyl and 1-heptyl ferulates at 90 degrees C. The system could be stably operated for the 1-heptyl ferulate synthesis at 90 degrees C for at least two weeks.

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Section: Introductionmentioning

confidence: 99%

Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature

et al. 2006

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“…We reported the synthesis of alkyl ferulates in primary alcohols using an immobilized lipase 7) . Alkyl ferulates were more soluble in oil and suppressed more effectively the oxidation of linoleic acid in both bulk 8) and encapsulated 9) systems than unmodified ferulic acid.…”

Section: Introductionmentioning

confidence: 98%

Continuous Synthesis of Glyceryl Ferulate Using Immobilized Candida antarctica Lipase

et al. 2008

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Glyceryl ferulate was synthesized through condensation of ferulic acid and glycerol at 50 in glycerols with different water contents using an immobilized lipase from Candida antarctica in a batch reactor, and condensation in the glycerol with a 7.5% (w/w) water content was shown to be the favorite. The solubility of ferulic acid was higher at higher temperature in glycerol with a lower water content. The viscosity was lower at higher temperature for the glycerol with a higher water content. The condensation was carried out using a batch reactor at a temperature from 50 to 90 . These observations indicated that the condensation at 80 in the glycerol with a 7.5% (w/w) water content was the most adequate for continuously synthesizing glyceryl ferulate. A reactor system was constructed for the continuous synthesis and was steadily operated to realize a productivity of 430 kg/(m 3 -reactor(day) without any decrease in the conversion for at least 6 days.

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“…A related study has indicated that the ester form of FA has better antioxidant activity than the original form, especially when compared to butylated hydroxytoluene (BHT) [7]. To overcome the problem of poor solubility, pharmaceutical particle technology of chemical modifications has attracted attention [8][9][10][11][12][13]. However, it is difficult to chemically synthesize such derivatives because FA is oxidation-sensitive under certain pH conditions [7,14,15].…”

Section: Introductionmentioning

confidence: 99%

Developing a High-Temperature Solvent-Free System for Efficient Biocatalysis of Octyl Ferulate

Huang

Chen

et al. 2018

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Ferulic acid esters have been suggested as a group of natural chemicals that have the function of sunscreen. The study aimed to utilize an environmentally-friendly enzymatic method through the esterification of ferulic acid with octanol, producing octyl ferulate. The Box-Behnken experimental design for response surface methodology (RSM) was performed to determine the synthesis effects of variables, including enzyme amount (1000-2000 propyl laurate units (PLU)), reaction temperature (70-90 • C), and stir speed (50-150 rpm) on the molar conversion of octyl ferulate. According to the joint test, both the enzyme amount and reaction temperature had great impacts on the molar conversion. An RSM-developed second-order polynomial equation further showed a data-fitting ability. Using ridge max analysis, the optimal parameters of the biocatalyzed reaction were: 72 h reaction time, 92.2 • C reaction temperature, 1831 PLU enzyme amount, and 92.4 rpm stir speed, respectively. Finally, the molar conversion of octyl ferulate under optimum conditions was verified to be 93.2 ± 1.5%. In conclusion, it has been suggested that a high yield of octyl ferulate should be synthesized under elevated temperature conditions with a commercial immobilized lipase. Our findings could broaden the utilization of the lipase and provide a biocatalytic approach, instead of the chemical method, for ferulic acid ester synthesis.

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Suppressive Effect of Alkyl Ferulate on the Oxidation of Linoleic Acid

Cited by 23 publications

References 13 publications

Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature

Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature

Continuous Synthesis of Glyceryl Ferulate Using Immobilized Candida antarctica Lipase

Developing a High-Temperature Solvent-Free System for Efficient Biocatalysis of Octyl Ferulate

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