Enzymatic synthesis of geranyl acetate by transesterification with acetic anhydride as acyl donor

1996 ◽  
Vol 73 (11) ◽  
pp. 1379-1384 ◽  
Author(s):  
Lisa N. Yee ◽  
Casimir C. Akoh
Keyword(s):  
Acetic Anhydride ◽  
Enzymatic Synthesis ◽  
Geranyl Acetate ◽  
Acyl Donor

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 Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives

Catalysts ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 739
Author(s):  
Zhiqiang Zou ◽  
Lingmei Dai ◽  
Dehua Liu ◽  
Wei Du
Keyword(s):  
Vitamin E ◽  
Enzymatic Synthesis ◽  
Catalytic Efficiency ◽  
Research Progress ◽  
Acyl Donor ◽  
Environmental Friendliness ◽  
Donor And Acceptor ◽  
Improved Stability ◽  
Enzymatic Acylation ◽  
Reaction Media

Vitamin E is easily oxidized by light, air, oxidizing agents and heat, limiting its application in many ways. Compared to vitamin E, vitamin E ester derivatives exhibit improved stability and a stronger antioxidant capacity, and even gain new biological functions. In recent years, enzymatic synthesis of vitamin E ester derivatives has received increasing attention due to its environmental friendliness, high catalytic efficiency, and inherent selectivity. This paper reviews the related progress of lipase-mediated preparation of vitamin E ester derivatives. The function of different vitamin E ester derivatives, and the main factors influencing the enzymatic acylation process, including enzyme species, acyl donor and acceptor, reaction media and water activity, are summarized in this paper. Finally, the perspective of lipase-catalyzed synthesis of vitamin E ester derivatives is also discussed.

The reaction of amines with conjugated dienes in the presence of alkali naphthalenide. A new synthesis of geranyl acetate

1974 ◽  
Vol 27 (3) ◽  
pp. 531 ◽  
Author(s):  
T Fujita ◽  
K Suga ◽  
S Watanabe
Keyword(s):  
Acetic Anhydride ◽  
Conjugated Dienes ◽  
Geranyl Acetate ◽  
Conjugated Diene ◽  
New Synthesis ◽  
Sodium Naphthalenide

Reaction of a conjugated diene with diethylamine using sodium naphthalenide in tetrahydrofuran gives a mixture of β,γ-unsaturated amines. From myrcene, N,N-diethyl-2-ethylidene-6-methylhept-5-enylamine, N,N-diethylnerylamine and N,N-diethylgeranylamine are obtained. Reaction of β,γ-unsaturated amines with acetic anhydride gives a mixture of β,γ-unsaturated acetates. From N,N-diethylgeranylamine, a mixture of neryl acetate and geranyl acetate is obtained.

Application of partially concentrated Candida rugosa lipase in the enzymatic synthesis of geranyl acetate in organic solvent

2017 ◽  
Vol 12 ◽  
pp. 90-95 ◽  
Author(s):  
B.H. Rosa ◽  
G.S. Silva ◽  
G.J.A. Conceição ◽  
R.A. Carvalho ◽  
E. Aguiar-Oliveira ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Enzymatic Synthesis ◽  
Candida Rugosa ◽  
Candida Rugosa Lipase ◽  
Geranyl Acetate

scholarly journals Enzymatic synthesis of ampicillin in precipitated medium with different acyl donor derivatives: perspectives for industrial application

2009 ◽  
Vol 25 ◽  
pp. S165
Author(s):  
R. Giordano ◽  
M. Ribeiro ◽  
R. Giordano ◽  
F. Batigalhia ◽  
G. Leite
Keyword(s):  
Industrial Application ◽  
Enzymatic Synthesis ◽  
Acyl Donor

New findings about the lipase acetylation of nanofibrillated cellulose using acetic anhydride as acyl donor

2015 ◽  
Vol 125 ◽  
pp. 340-351 ◽  
Author(s):  
Mojca Božič ◽  
Vera Vivod ◽  
Sabina Kavčič ◽  
Maja Leitgeb ◽  
Vanja Kokol
Keyword(s):  
Acetic Anhydride ◽  
Nanofibrillated Cellulose ◽  
Acyl Donor ◽  
New Findings

Effects of acyl donor type, catalyst type, and reaction conditions on the activity and selectivity of Friedel-Crafts acylation

2009 ◽  
Vol 63 (3) ◽  
Author(s):  
Adi Wolfson ◽  
Rao Madhusudhan ◽  
Ayelet Shapira-Tchelet ◽  
Miron Landau
Keyword(s):  
Acetic Anhydride ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Acyl Donor ◽  
Reaction Conditions ◽  
Acidic Catalysts ◽  
Catalyst Type ◽  
Anisole Acylation ◽  
Full Conversion

AbstractAcylation of anisole and 3-methylanisole was performed with several acylating reagents (acetylation by AcCl and Ac2O and bromoacetylation by BrAcCl and (BrAc)2O) over different solid acid catalysts. The reaction conditions were optimized with respect to the acylation reagent, overall yield, solid acid catalyst, and the products selectivities. While acylation of anisole with acetyl chloride or acetic anhydride resulted in its full conversion to para-substituted acetophenone, the use of bromoacetyl bromide or bromoacetic anhydride yielded also the ortho-substituted product. Acylation of 3-methylanisole also yielded both para- and ortho-substitutions, and the products distribution was affected by the reaction conditions and catalyst type. It was found that while more acidic catalysts (caesium salt of heteropolyacid and zeolites) were the most active towards anisole acylation, the most active catalysts for the acylation of 3-methylanisole were ion-exchange catalysts. Employing HY-740 zeolite resulted in the highest ortho-selectivity in the acylation of anisole with bromoacetyl bromide and bromoacetic anhydride and in the acylation of 3-methylanisole with acetic anhydride.

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