Lipase-Catalyzed Transesterification Synthesis of Geranyl Acetate in Organic Solvents and Its Kinetics

Xiong, Jian; Huang, Ya-Juan; Zhang, Hua; Hou, Liyun

doi:10.3136/fstr.20.207

Cited by 33 publications

(18 citation statements)

References 25 publications

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“…However, it slightly decreased at 55 °C (56.6 ± 2.2%), possibly due to the esterification of EGCG, which can change hydrolysis direction under high temperatures [ 13 ]. High temperatures enhance the interaction between enzymes and substrates [ 31 ]. High temperatures can also lead to a loss of enzyme activity by destroying its active conformation.…”

Section: Resultsmentioning

confidence: 99%

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

et al. 2021

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Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the molar ratio of vinyl stearate: EGCG as 3:1, an enzyme amount of 4.0% (ratio of substrate mass), and a reaction temperature and time of 50 °C and 96 h, respectively, achieving 65.2% EGCG conversion. HPLC–MS and NMR were used to determine the structure of EGCG stearyl derivative (3″,5″-2-O-stearyl-EGCG). The lipophilicity of EGCG stearyl derivatives (3.49 ± 0.34) was higher (5.06 times) than that of the parent EGCG (0.69 ± 0.08). Furthermore, EGCG stearyl derivatives had excellent lipid oxidation compared with BHT, BHA, and parent EGCG. The POVs of soybean oil with EGCG stearyl derivatives (18.17 ± 0.92 mEq/kg) were significantly reduced (by 62.5%) at 21 d compared with those of EGCG (48.50 ± 1.23 mEq/kg). These results indicate that EGCG derivatives have broad antioxidant application prospects in lipophilic environments/high-fat food.

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Section: Resultsmentioning

confidence: 99%

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

et al. 2021

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“…However, the trend was reversed at 50°C with the maximum value of 70.1 ± 1.9%. Although, the increasing temperature can reduce the viscosity of the mixture, and increase the mutual solubility and matrix diffusion, thus enhancing the interactions between the catalytic enzymes and the substrates and increasing the reaction rate (Xiong et al., 2014), esterification reaction of EGCG may promote the reverse reaction under high temperature, resulting in a decrease in the conversion rate of EGCG (N. Zhu et al., 2014), as well as high temperature may destroy the enzyme, leading to loss of selectivity and activity. Therefore, the selection of temperature has a vital influence on the progress of the enzyme‐catalyzed reaction and the allocation of resources.…”

Section: Resultsmentioning

confidence: 99%

Structural characterization and antioxidant property of enzymatic‐transesterification derivatives of (−)‐epigallocatechin‐3‐O‐gallate and vinyl laurate

Jiang

Wang

Huang

et al. 2021

Journal of Food Science

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(−)‐Epigallocatechin‐3‐O‐gallate(EGCG) was enzymatically modified to enhance the lipophilicity and the antioxidant property. The determination of optimal reaction conditions are as follows: Lipase DF “Amano” 15 and acetone were used as catalyst and solvent, respectively. Equal molar of EGCG and vinyl laurate (1:1); lipase addition of 6.0% (w/w of total substrates); reaction temperature of 50°C and reaction time of 96 h, which obtained the conversion rate of EGCG at 80.1%. The structure of EGCG lauroyl derivatives were 5″‐O‐lauroyl‐EGCG, 3″,5″‐2‐O‐lauroyl‐EGCG, and 5′,3″,5″‐3‐O‐lauroyl‐EGCG, identified by high‐performance liquid chromatography‐mass spectrometry (HPLC–MS) and nuclear magnetic resonance (NMR). Compared with the logP of precursor EGCG (0.69 ± 0.03), the logP of EGCG lauroyl derivatives was 1.37 ± 0.19, 2.27 ± 0.33, and 3.28 ± 0.37, increasing by 0.98, 2.28, and 3.75 times, respectively (p < 0.05), suggesting the grafted fatty acid chains make EGCG derivatives more lipophilic, and the lipid solubility gradually increased as the number of substituents increased. Furthermore, EGCG lauroyl derivatives had excellent lipid oxidation than that of EGCG. The POVs (peroxide values) of soybean oil with mono‐, di‐, tri‐lauroyl EGCG were significantly reduced by 42%, 47%, and 57% than that of EGCG at 21 days, respectively, indicating the antioxidative inhibition of these derivatives decreased with the increase in substituents. This indicates that these derivatives have broad prospects of the antioxidant application while improving their solubility properties in lipophilic environments/high‐fat food. Practical Application: The lipophilic esterification reaction of EGCG catalyzed by new catalytic lipase DF “Amano” 15 was carried out in a non‐aqueous solvent.Various reaction factors on a higher conversion rate of EGCG lauroyl derivatives were evaluated. The lipophilicity and antioxidant properties of EGCG lauroyl derivatives were much excellent than that of parent EGCG.

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“…Geranyl acetate, a monoterpene ester commonly used as an important flavor component, has a sweet lemon fruity flavor and the fragrance of rose and lavender. Geranyl acetate is mainly used to prepare fruit‐flavored essences with aromas of lemon, lavender, rose, Convallaria majalis , Osmanthus fragrans , and Flores aurantii as important flavor and fragrance components in the food, perfume, cosmetics, brewing, and pharmaceutical industries [6–8] …”

Section: Introductionmentioning

confidence: 99%

Cross‐Linked Enzyme‐Adhered Nanoparticles (CLEANs) for Continuous‐Flow Bioproduction

et al. 2021

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Nanostructured but micro‐sized biocatalysts were created by bottom‐up technology using multi‐functionalized silica nanoparticles (NPs) as nano‐sized building blocks to form cross‐linked enzyme‐adhered nanoparticles (CLEANs) as robust micro‐sized particles with beneficial internal structure and good mechanical properties. Systematic surface modification of NPs with a grafting mixture consisting of organosilanes with reactive (aminopropyl) and inert (e. g., vinyl, propyl, phenyl, or octyl) functions resulted in functional NPs enabling cross‐linking agents, such as glutardialdehyde or bisepoxides (glycerol diglycidyl ether, neopentylglycol diglycidyl ether, and poly(propylene glycol) diglycidyl ether), to bind and cross‐link enzymes covalently and to form macroporous microparticles. These CLEANs were able to diminish several weaknesses of traditional cross‐linked enzyme aggregates as biocatalysts, such as poor mechanical resistance, difficult recovery, and storage, strengthening their use for packed‐bed enzyme reactors. Lipase B from Candida antarctica (CaLB) was selected as model enzyme for development of robust CLEANs, which were successfully tested for various industrially relevant applications including a kinetic resolution of a racemic alcohol and the production of various natural fragrance compounds under continuous‐flow conditions.

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Lipase-Catalyzed Transesterification Synthesis of Geranyl Acetate in Organic Solvents and Its Kinetics

Cited by 33 publications

References 25 publications

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems

Structural characterization and antioxidant property of enzymatic‐transesterification derivatives of (−)‐epigallocatechin‐3‐O‐gallate and vinyl laurate

Cross‐Linked Enzyme‐Adhered Nanoparticles (CLEANs) for Continuous‐Flow Bioproduction

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