Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates

Vosmann, Klaus; Weitkamp, Petra; Weber, Nikolaus

doi:10.1021/jf060052t

Cited by 41 publications

(42 citation statements)

References 46 publications

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“…Cinnamic acid, 3-phenyl-2-propenoic acid, is an unsubstituted phenylpropanoid with limited antioxidant capacity. Previous studies reported the chemical and biocatalytic synthesis of cinnamoyl esters and glycerols [9,10]. A recent work examined the kinetics of chemical esterification of glycerol with cinnamic acid and its derivatives [11].…”

Section: Introductionmentioning

confidence: 99%

Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids

Choo

Birch

2008

Lipids

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Lipase-catalyzed transesterification of triolein with cinnamic and ferulic acids using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate the antioxidant activity of the lipophilized products as model systems for enhanced protection of unsaturated oil. The lipophilized products were identified using ESI-MS. Free radical scavenging activity was determined using the DPPH radical method. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Ferulic acid showed much higher radical scavenging activity than cinnamic acid, which has limited activity. The esterification of cinnamic acid and ferulic acid with triolein resulted in significant increase and decrease in the radical scavenging activity, respectively. These opposite effects were due to the effect of addition of electron-donating alkyl groups on the predominant mechanism of reaction (hydrogen atom transfer or electron transfer) of a species with DPPH. The effect of esterification of cinnamic acid was confirmed using ethyl cinnamate which greatly enhances the radical scavenging activity. Although, compared to the lipophilized cinnamic acid product, the activity was lower. The radical scavenging activity of the main component isolated from lipophilized cinnamic acid product using solid phase extraction, monocinnamoyl dioleoyl glycerol, was as good as the unseparated mixture of lipophilized product. Based on the ratio of a substrate to DPPH concentration, lipophilized ferulic acid was a much more efficient radical scavenger than lipophilized cinnamic acid.

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Section: Introductionmentioning

confidence: 99%

Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids

Choo

Birch

2008

Lipids

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“…4. In previous studies [5][6][7][8][21][22][23][24], different phenolic acids from cinnamic series have been used for esterification in various media. It was found esterification was possible for the phenolic acids which the aromatic cycle was not parahydroxylated and the side chain was saturated.…”

Section: Effect Of Substrate Concentrationmentioning

confidence: 99%

“…However, most of phenolic acids are hydrophilic compounds and can mainly confer their functional properties or health effects in aqueous environments or water compartments [4]. Therefore, to apply natural phenolic acids in lipophilic formulation and processing, lipophilization is needed where enzymatic esterification with alcohols has proved itself to be a promising approach [5][6][7][8].…”

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confidence: 99%

Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids

Yang

Guo

2012

J Americ Oil Chem Soc

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Lipophilic derivatives of phenolic acids could greatly extend their applications in the lipophilic bioenvironment and food processing, therefore, developing an efficient lipophilization reaction system constitutes an interesting topic of biocatalysis. Low solubility of phenolic acids in most enzyme-benign solvents represents the main reason for the inefficiency of enzymatic production of lipophilic phenolic derivatives. This work reports a novel approach to improve Candida antartica lipase B (Novozym 435) catalyzed lipophilization of phenolic acids by means of ionic liquids (IL), trioctylmethylammonium trifluoroacetate (tOMA.TFA) assisted solubilization of the substrate. In this approach, the IL plays two major roles, namely, to dissolve phenolic acids at high concentration so as to create a homogeneous system with another substrate-1-octanol, and to be benign to the enzyme to keep the biocatalyst active; which is proved itself to be a correct strategy as improved conversion and volumetric productivity are obtained. The results showed that dosage of IL (denoted as the volume ratio of 1-octanol/tOMA.TFA), concentration of dihydrocaffeic acid (DHCA) and temperature are the key parameters governing the reaction efficiency. A maximum conversion of DHCA was achieved at the ratio of 1-octanol/tOMA.TFA 12:1 (v/v) (1-octanol/ DHCA, 38:1 (mol/mol)). A temperature of 70°C was correct to obtain optimal conversion of DHCA. Even though the conversion of DHCA was higher at lower concentrations of DHCA, the overall volumetric productivity (reaction rate) was much higher when a high concentration of DHCA (1.6 M) was applied, due to IL-assisted solubilization of DHCA. Remarkable enhancement of the conversions of ferulic and caffeic acids were achieved, when the same reaction approach (tOMA.TFA assisted solubilization) was applied to these two phenolic acids, indicating the general applicability of this novel approach.

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“…In an early study, C. rugosa lipase was compared to other lipases on different cinnamic acid derivatives, showing 8% conversion to 1‐octanol in 12 days for ferulic acid in solvent‐free system . Later on, applying C. rugosa lipase in solvent‐free condition under reduced pressure (80 kPa) for the esterification of 4‐methoxycinnamic acid with oleyl alcohol lead to no or very low‐esterification activity . However, also a reasonable conversion of 26% has been reported for the transesterification of ethyl ferulate with tributyrin in toluene in 4 days .…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of steryl ferulates

Schär

Nyström

2016

Euro J Lipid Sci & Tech

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Steryl ferulates are plant sterols esterified to ferulic acid, a common phenolic acid. This esterification leads to sterol esters with improved biological properties, such as antioxidant activity. Commercially available and extracted steryl ferulates from rice bran are often limited in their sterol profiles. For further research and later food applications, a simple enzymatic esterification could address the lack of availability of single steryl ferulates. Whereas several enzymatic procedures for the esterification of steryl fatty acid esters have been published, no fully enzymatic procedure for steryl ferulates has been reported so far. We optimized both direct esterification of b-sitosterol with ferulic acid as well as transesterification with ethyl ferulate yielding steryl ferulates. The reaction was catalyzed by a lipase from Candida rugosa, which lead to yields of 35 and 55% for the direct esterification and transesterification, respectively. Moreover, both reactions followed a similar time course over incubation. The enzyme activity was rather low, which is probably due to the specificity of the different isoenzymes of C. rugosa lipase. However, successful conditions for a fully enzymatic synthesis of steryl ferulates are reported for the first time.Practical applications: This enzymatic procedure leads to steryl ferulates, which do not need thorough purification, as no toxic catalysts were applied. This is especially an advantage when animal or human studies are conducted, which are needed for further evaluation of the potential health benefits of steryl ferulates. Further, it is less labor intensive than earlier published procedures using vinyl esters as substrates, which have to be synthesized and chromatographically purified.

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Solvent-free Lipase-Catalyzed Preparation of Long-Chain Alkyl Phenylpropanoates and Phenylpropyl Alkanoates

Cited by 41 publications

References 46 publications

Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids

Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids

Ionic Liquid‐Assisted Solubilization for Improved Enzymatic Esterification of Phenolic Acids

Enzymatic synthesis of steryl ferulates

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