Enzymatic Synthesis of Eugenyl Acetate from Essential Oil of Clove Using Lipases in Liquid Formulation as Biocatalyst

2021 ◽  
Author(s):  
Leandro Santolin ◽  
Karina G. Fiametti ◽  
Viviane da Silva Lobo ◽  
João H. C. Wancura ◽  
J. Vladimir Oliveira
Keyword(s):  
Essential Oil ◽  
Enzymatic Synthesis ◽  
Liquid Formulation ◽  
Eugenyl Acetate

Enzymatic Synthesis of Eugenyl Acetate from Essential Oil of Clove Using Lipases in Liquid Formulation as Biocatalyst

2021 ◽  
Author(s):  
Leandro Santolin ◽  
Karina G. Fiametti ◽  
Viviane da Silva Lobo ◽  
João H. C. Wancura ◽  
José Vladimir Oliveira
Keyword(s):  
Essential Oil ◽  
Acetic Anhydride ◽  
Enzymatic Synthesis ◽  
Molar Ratio ◽  
Syzygium Aromaticum ◽  
Liquid Formulation ◽  
Promising Alternative ◽  
Eugenyl Acetate ◽  
Extensive Evaluation ◽  
Pharmaceutical Industries

Abstract In this research, eugenyl acetate, a compound with flavoring, antioxidant and antimicrobial properties, was obtained from essential oil of clove (Syzygium aromaticum) via liquid lipase-mediated acetylation. Clove essential oil was extracted by drag water vapor from dry flower buds and its physic-chemical characteristics were analyzed. For the enzymatic synthesis, an extensive evaluation of reaction parameters was accomplished through employment of distinct reaction temperatures, acetic anhydride to eugenol molar ratios, enzyme loads and three different lipases (a lyophilized enzyme produced by solid-state fermentation of sunflower seed with Penicillium sumatrense microorganism and others two commercial lipases – Lipozyme TL 100L and CALB L). Characterization by Infrared Spectroscopy and Nuclear Magnetic Resonance (1H NMR and 13C) was used to confirm the presence of eugenyl acetate in the samples. Through optimized conditions (55 °C, acetic anhydride to eugenol molar ratio of 1:1, 10 wt% of Lipozyme TL 100L), 91.80 % of conversion after 2 h was achieved to the eugenyl acetate production. With the results obtained, it was possible to conclude that the use of lipases in liquid formulation is a promising alternative for the synthesis of essential esters largely applied on food, cosmetic and pharmaceutical industries.

scholarly journals Chemical composition and content of essential oil from the bud of cultivated Turkish clove (Syzygium aromaticum L.)

BioResources ◽  
2007 ◽  
Vol 2 (2) ◽  
pp. 265-269 ◽  
Author(s):  
M. Hakki Alma ◽  
Murat Ertaş ◽  
Siegfrie Nitz ◽  
Hubert Kollmannsberger
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
Mediterranean Region ◽  
Steam Distillation ◽  
Syzygium Aromaticum ◽  
Distillation Method ◽  
Eugenyl Acetate ◽  
Clove Bud Oil ◽  
Oil Company

In this study, clove bud oil, which was cultivated in the Mediterranean region of Turkey, was provided from a private essential oil company in Turkey. Essential oil from clove (Syzygium aromaticum L.) was obtained from steam-distillation method, and its chemical composition was analyzed by GC and GC-MS. The results showed that the essential oils mainly contained about 87.00% eugenol, 8.01% eugenyl acetate and 3.56% β-Caryophyllene. The chemical composition of the Turkish clove bud oil was comparable to those of trees naturally grown in their native regions.

Supercritical CO2 Extraction of Essential Oil from Clove Bud: Effect of Operation Conditions on the Selective Isolation of Eugenol and Eugenyl Acetate

2005 ◽  
Vol 60 (11) ◽  
pp. 1197-1201 ◽  
Author(s):  
Farshad Yazdani ◽  
Morteza Mafi ◽  
Fathollah Farhadi ◽  
Kourosh Tabar-Heidar ◽  
Kioumars Aghapoor ◽  
...  
Keyword(s):  
Essential Oil ◽  
Supercritical Fluid Extraction ◽  
Supercritical Fluid ◽  
Steam Distillation ◽  
Fluid Extraction ◽  
Operation Conditions ◽  
Eugenyl Acetate ◽  
Assisted Extraction ◽  
Series Of Experiments

The supercritical fluid extraction (SFE) of clove bud essential oil was studied using CO2 as solvent. The effect of operation conditions was analyzed in a series of experiments at temperatures between 325 and 416 K and pressures between 110 and 190 bar. The collected extracts were analyzed and the relative composition of the essential oil was determined. The optimum condition was found in a temperature of 353 K and at a pressure of 190 bar, minimizing the number of extracts to two compounds (eugenol and eugenyl acetate). The extract obtained from clove bud by using supercritical fluid extraction was compared with the essential oil obtained by steam distillation and microwave-assisted extraction by considering both quantity and quality of the product. The oil yield was higher in steam distillation and microwave oven extraction. In contrast, oil extracted by using SFE contained higher amount of eugenol and eugenyl acetate.

scholarly journals ACTIVITY LARVICIDE OF THE ESSENTIAL OIL SYZYGIUM AROMATICUM (CARNIVAL-OF-INDIA) IN FRONT OF THE MOSQUITO AEDES AEGYPTI (LINNAEUS, 1762)

2018 ◽  
Vol 15 (29) ◽  
pp. 184-195
Author(s):  
P. R. B. GOMES ◽  
R. W. S. De OLIVEIRA ◽  
V. E. MOUCHREK FILHO ◽  
A. A. Do NASCIMENTO ◽  
A. P. EVERTON ◽  
...  
Keyword(s):  
Essential Oil ◽  
Aedes Aegypti ◽  
Water Contamination ◽  
Public Health Problem ◽  
Syzygium Aromaticum ◽  
Eugenyl Acetate ◽  
Frequent Use ◽  
Third Stage ◽  
Oil Density ◽  
Main Component

Dengue, zika virus and chicungunya are diseases transmitted by the bite of the female mosquito Aedes aegypti Linn. Because of this, these diseases pose a public health problem, especially in tropical countries. To date, there are no specific vaccines that act against the different serotypes of the disease. In this way, the measures adopted to combat it are restricted in the control of the mosquito. This is done using larvicide chemicals and insecticides, whose main component are organophosphorus, such as Temephos and pyrethroids. However, frequent use of these products has brought over the years some disadvantages: mosquito resistance, water contamination and attack on non-target living beings. Therefore, this work evaluated the larvicidal potential of the flower buds of the Syzygium aromaticum species against larvae in the third stage of the Aedes aegypti mosquito (Linnaeus, 1762). For this, the essential oil was quantitated by hydrodistillation. The physicochemical properties of the essential oil (density, refractive index, solubility, color and appearance) were determined. In addition, the oil was characterized chemically, quantifying its components and identifying its major component by gas chromatography coupled to mass spectrometry. The oil LC50 was calculated, in addition to the confidence limit at 95% probability, from the methods of Reed-Muench (1938) and Pizzi (1950), respectively. The yield of oil was 3.54% m / m and 3.63% v / m. Using the method used, it was possible to identify and quantify eugenol (52.53%), caryophyllene (37.25%), humulene (4.11%), eugenyl acetate (4.05%) and copaene %), With eugenol being the major component of the oil. The oil exhibited larvicidal activity being totally lethal at a concentration of 120 μg/mL.

Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification

2014 ◽  
Vol 174 (4) ◽  
pp. 1286-1298 ◽  
Author(s):  
Adriana B. Vanin ◽  
Tainara Orlando ◽  
Suelen P. Piazza ◽  
Bruna M. S. Puton ◽  
Rogério L. Cansian ◽  
...  
Keyword(s):  
Essential Oil ◽  
Antioxidant Activities ◽  
Enzymatic Esterification ◽  
Eugenyl Acetate ◽  
Clove Essential Oil

scholarly journals Toxicity of clove essential oil and its ester eugenyl acetate against Artemia salina

2017 ◽  
Vol 77 (1) ◽  
pp. 155-161 ◽  
Author(s):  
R. L. Cansian ◽  
A. B. Vanin ◽  
T. Orlando ◽  
S. P. Piazza ◽  
B. M. S. Puton ◽  
...  
Keyword(s):  
Essential Oil ◽  
Artemia Salina ◽  
Insect Vector ◽  
Enzymatic Esterification ◽  
Clove Oil ◽  
Eugenyl Acetate ◽  
Biological Potential ◽  
Insecticide Activity ◽  
Clove Essential Oil ◽  
High Doses

Abstract The production of compounds via enzymatic esterification has great scientific and technological interest due to the several inconveniences related to acid catalysis, mainly by these systems do not fit to the concept of “green chemistry”. Besides, natural products as clove oil present compounds with excellent biological potential. Bioactives compounds are often toxic at high doses. The evaluation of lethality in a less complex animal organism can be used to a monitoring simple and rapid, helping the identification of compounds with potential insecticide activity against larvae of insect vector of diseases. In this sense, the toxicity against Artemia salina of clove essential oil and its derivative eugenyl acetate obtained by enzymatic esterification using Novozym 435 as biocatalyst was evaluated. The conversion of eugenyl acetate synthesis was 95.6%. The results about the evaluation of toxicity against the microcrustacean Artemia salina demonstrated that both oil (LC50= 0.5993 µg.mL–1) and ester (LC50= 0.1178 µg.mL–1) presented high toxic potential, being the eugenyl acetate almost 5 times more toxic than clove essential oil. The results reported here shows the potential of employing clove oil and eugenyl acetate in insecticide formulations.

scholarly journals Variations in yield and composition of leaf essential oil from Syzygium aromaticum at various phases of development

2016 ◽  
Vol 5 (1) ◽  
pp. 90 ◽  
Author(s):  
Razafimamonjison Gaylor ◽  
Boulanger Renaud ◽  
Jahiel Michel ◽  
Ramanoelina Panja ◽  
Fawbush Fanja ◽  
...  
Keyword(s):  
Essential Oil ◽  
Essential Oils ◽  
Divergent Evolution ◽  
Syzygium Aromaticum ◽  
Maximum Percentage ◽  
Mature Leaves ◽  
Green Leaves ◽  
Eugenyl Acetate ◽  
Young Leaves ◽  
Phases Of Development

<p>The changes in the essential oil yield and composition from <em>Syzygium aromaticum</em> leaf harvested at different phases of development from young leaves to mature leaves were studied. Separation of the essential oils was conducted by steam distillation in a Clevenger apparatus for about 4h. Essential oils analyses were performed by GC/MS. The yield of essential oil (ml per 100 g of DM) of the leaf following the four phases of development was in order of: young leaves (5.1%) &gt; expanded leaves 1 (4.5%) &gt; expanded leaves 2 (4.1%) &gt; mature leaves (3.8%). Sixteen compounds were detected by GC/MS. Eugenol and eugenyl acetate were the dominant components. Eugenol and eugenyl acetate amount had a divergent evolution during the four expansions of leaves. When eugenol reached its highest percentages at expanded leaves 2 (84.00 - 90.48%) and mature leaves stage (88.32 - 90.22%), eugenyl acetate reached the lowest ones with, respectively, 0.96 - 7.16% and 0.36 - 1.64%, but when the eugenyl acetate reached a maximum percentage at young leaves stage with 61.44 - 65.52%, eugenol reached a minimum of 25.43 - 30.38%. It is judicious to collect and extract <em>S. aromaticum</em> leaf in expended leaves 2 (pale green leaves) and mature leaves stage (dark green leaves) in order to obtain the optimal yield and maximum percentage of eugenol.</p>

scholarly journals Essential oil composition from fresh and dried leaves of C. tamala

2013 ◽  
Vol 48 (2) ◽  
pp. 151-154 ◽  
Author(s):  
JU Chowdhury ◽  
GC Shaha ◽  
F Begum ◽  
MNH Bhuiyan ◽  
M Rahim
Keyword(s):  
Essential Oil ◽  
Essential Oil Composition ◽  
Methyl Eugenol ◽  
Oil Composition ◽  
Fresh Leaf ◽  
Eugenyl Acetate ◽  
Cinnamomum Tamala ◽  
Leaf Oil

The essential oil of Cinnamomum tamala Nees grown at laboratory campus of BCSIR, Dhaka was obtained from its fresh and dried leaves by hydrodistillation. The oils were analyzed by GC-MS. The major components in the fresh leaf oil were eugenol (75.28%) followed by spathulenol (10.06%), eugenyl acetate (9.82%) and in the dried leaf oil were eugenol (68.02%), spathulenol (12.73%), methyl eugenol(6.42%), ?-humulene (4.35%) & caryophyllene (3.58%). Bangladesh J. Sci. Ind. Res. 48(2), 151-154, 2013 DOI: http://dx.doi.org/10.3329/bjsir.v48i2.15747

scholarly journals Syzygium aromaticum L. (Clove): A vital herbal drug used in periodontal disease

2017 ◽  
Vol 5 (02) ◽  
pp. 45-51 ◽  
Author(s):  
Deepanjeet Kaur ◽  
Kaushal K. Chandrul
Keyword(s):  
Essential Oil ◽  
Periodontal Disease ◽  
Essential Oils ◽  
Geographic Origin ◽  
Major Constituent ◽  
Lower Amount ◽  
Syzygium Aromaticum ◽  
Great Opportunity ◽  
Eugenyl Acetate ◽  
Main Component

Cloves are widely used in dental care, and are effective against a large number of bacteria. The main component of clove oil is eugenol, with β-caryophyllene and eugenyl acetate. The review of published results reveals a great opportunity to treat periodontal disease. The purpose of this study is to compare the bud, leaf and stem essential oil compositions from S. aromaticum and then to evaluate the correlation of the results with anatomic and geographical origins of the essential oil. Many commercial essential oils isolated from bud, leaf and stem were used in this work. The oils were analyzed by GC and then constituents were identified from the whole. The major constituent in oils was eugenol, with increasing percentages from bud (72.08 - 82.36%) to leaf (75.04 - 83.58%) and stem (87.52 - 96.65%). In the clove bud essential oil eugenyl acetate is the second major component (8.6 - 21.3%) while detected in considerably lower amount in the leaf (0 - 1.45%) and stem (0.07 - 2.53%). In leaf essential oil, the second main compounds were β-caryophyllene (11.65 - 19.53%) and α-humulene (1.38 - 2.17%), less represented in bud essential oils (2.76 - 8.64% and 0.34 - 1.04% respectively) and in stem essential oils (1.66 - 9.7% and 0.22 - 1.31% respectively). For each plant material, variation in the percentage of the main constituents was observed according to the sample geographic origin.

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