Enzymatic synthesis of geranyl acetate in batch and fed-batch reactors and evaluation of its larvicidal activity against Rhipicephalus (Boophilus) microplus

Remonatto, Daniela; Fantatto, Rafaela Regina; Pietro, Rosemeire Cristina Linhari Rodrigues; Oliveira, J. Vladimir; Paula, Ariela Veloso de; Bassan, Juliana Cristina

doi:10.1016/j.procbio.2022.06.012

Cited by 10 publications

(6 citation statements)

References 123 publications

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“…In acidolysis reactions, where fatty acids are esterified to glycerol, an excess of fatty acids is beneficial because these compounds shift the chemical balance of the reaction toward product formation, resulting in a high DI [ 9 ]. However, such behavior occurs up to a certain limit; an excessive amount of fatty acids can lead to acidification of the microaqueous layer at the active site of lipases, causing denaturation [ 61 , 62 ]. In acidolysis reactions with long-chain fatty acids, such as C13:0 and C17:0, enzyme inhibition problems are not as frequent as when short-chain fatty acids (C5:0 and C9:0) are used [ 60 , 63 ].…”

Section: Resultsmentioning

confidence: 99%

“…It is also worth mentioning that an increase in oil/acid molar ratio, that is, an excess of capric acid, can be beneficial due to the increase in reagent availability, enhancing the probability of its esterification to triacylglycerol and causing a shift in esterification equilibrium. Enzymatic esterification is controlled thermodynamically, which contributes to the formation of a stagnate chemical equilibrium [ 61 , 64 ]. A strategy to shift the equilibrium is to produce an excess of one of the substrates [ 61 ].…”

Section: Resultsmentioning

confidence: 99%

“…Enzymatic esterification is controlled thermodynamically, which contributes to the formation of a stagnate chemical equilibrium [ 61 , 64 ]. A strategy to shift the equilibrium is to produce an excess of one of the substrates [ 61 ].…”

Section: Resultsmentioning

confidence: 99%

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Solvent-Free Enzymatic Synthesis of Dietary Triacylglycerols from Cottonseed Oil in a Fluidized Bed Reactor

et al. 2023

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The synthesis of structured lipids with nutraceutical applications, such as medium-long-medium (MLM) triacylglycerols, via modification of oils and fats represents a challenge for the food industry. This study aimed to synthesize MLM-type dietary triacylglycerols by enzymatic acidolysis of cottonseed oil and capric acid (C10) catalyzed by Lipozyme RM IM (lipase from Rhizomucor miehei) in a fluidized bed reactor (FBR). After chemical characterization of the feedstock and hydrodynamic characterization of the reactor, a 22 central composite rotatable design was used to optimize capric acid incorporation. The independent variables were cycle number (20–70) and cottonseed oil/capric acid molar ratio (1:2–1:4). The temperature was set at 45 °C. The best conditions, namely a 1:4 oil/acid molar ratio and 80 cycles (17.34 h), provided a degree of incorporation of about 40 mol%, as shown by compositional analysis of the modified oil. Lipozyme RM IM showed good operational stability (kd = 2.72 × 10−4 h−1, t1/2 = 2545.78 h), confirming the good reuse capacity of the enzyme in the acidolysis of cottonseed oil with capric acid. It is concluded that an FBR configuration is a promising alternative for the enzymatic synthesis of MLM triacylglycerols.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Solvent-Free Enzymatic Synthesis of Dietary Triacylglycerols from Cottonseed Oil in a Fluidized Bed Reactor

et al. 2023

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“…However, biocatalytic synthesis of avor esters is becoming more and more popular in the avor and fragrance industries, due to the advantages of selectivity and speci city, reusability, mild conditions and much purer products [11,12,13,14,15]. Esteri cation, interesteri cation, thioesteri cation, and transesteri cation processes are produced by enzymes such lipases and esterases and are catalyzed by the ping-pong bibi mechanism, ternary complex ordered bibi mechanism, or ternary complex random bibi mechanism [16,17,18,19]. A variety of functional groups, halides, and linear as well as cyclic alkyl alcohols are allowed under this procedure.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of novel pyrrole esters and their thermal stability

Zhou

Zhang

et al. 2023

Preprint

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In the present work a simple enzymatic approach (Novozym 435) for transesterification to synthesize pyrrole esters was reported. To generate the best reaction conditions, which resulted in the optimum yield of 92%, the effects of lipase type, solvent, lipase load, molecular sieves, substrate molar ratio of esters to alcohol, reaction temperature, reaction duration, and speed of agitation were evaluated. The range of alcohols was assessed under optimal circumstances. The spectrum observations conclusively demonstrated that the compounds could be generated with high yield under the circumstances utilized for synthesis. The odor characteristics of the pyrrolyl esters obtained were examined by gas chromatography-mass spectrometry-olfactometry (GC-MS-O). Among them, compounds of benzhydryl 1H-pyrrole-2-carboxylate (3h), butyl 1H-pyrrole-2-carboxylate (3i) and pentyl 1H-pyrrole-2-carboxylate (3j) present sweet and acid aroma. In addition, the thermal degradation process was further studied using the Py-GC/MS (pyrolysis-gas chromatography/mass spectrometry), TG (thermogravimetry), and DSC (differential scanning calorimeter) techniques. The outcomes of the Py-GC/MS, TG, and DSC techniques show that they have excellent thermal stability.

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“…However, biocatalytic synthesis of flavor esters is becoming more and more popular in the flavor and fragrance industries, due to the advantages of selectivity and specificity, reusability, mild conditions and much purer products [ 11 – 15 ]. Esterification, interesterification, thioesterification, and transesterification processes are produced by enzymes such lipases and esterases and are catalyzed by the ping-pong bibi mechanism, ternary complex ordered bibi mechanism, or ternary complex random bibi mechanism [ 16 – 19 ]. A variety of functional groups, halides, and linear as well as cyclic alkyl alcohols are allowed under this procedure.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of novel pyrrole esters and their thermal stability

Hu,

Zhou,

Zhang

et al. 2023

BMC Chemistry

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In the present work a simple enzymatic approach (Novozym 435) for transesterification to synthesize pyrrole esters was reported. To generate the best reaction conditions, which resulted in the optimum yield of 92%, the effects of lipase type, solvent, lipase load, molecular sieves, substrate molar ratio of esters to alcohol, reaction temperature, reaction duration, and speed of agitation were evaluated. The range of alcohols was assessed under optimal circumstances. The spectrum observations conclusively demonstrated that the compounds could be generated with high yield under the circumstances utilized for synthesis. The odor characteristics of the pyrrolyl esters obtained were examined by gas chromatography–mass spectrometry-olfactometry (GC–MS–O). Among them, compounds of benzhydryl 1H-pyrrole-2-carboxylate (3j), butyl 1H-pyrrole-2-carboxylate (3k) and pentyl 1H-pyrrole-2-carboxylate (3l) present sweet and acid aroma. In addition, the thermal degradation process was further studied using the Py–GC/MS (pyrolysis–gas chromatography/mass spectrometry), TG (thermogravimetry), and DSC (differential scanning calorimeter) techniques. The outcomes of the Py–GC/MS, TG, and DSC techniques show that they have excellent thermal stability.

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Enzymatic synthesis of geranyl acetate in batch and fed-batch reactors and evaluation of its larvicidal activity against Rhipicephalus (Boophilus) microplus

Cited by 10 publications

References 123 publications

Solvent-Free Enzymatic Synthesis of Dietary Triacylglycerols from Cottonseed Oil in a Fluidized Bed Reactor

Solvent-Free Enzymatic Synthesis of Dietary Triacylglycerols from Cottonseed Oil in a Fluidized Bed Reactor

Enzymatic synthesis of novel pyrrole esters and their thermal stability

Enzymatic synthesis of novel pyrrole esters and their thermal stability

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