Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation

被引:20
|
作者
Silva, Maria Jose A. [1 ]
Loss, Raquel A. [1 ,2 ]
Laroque, Denise A. [1 ]
Lerin, Lindomar A. [1 ]
Pereira, Gabriela N. [1 ]
Thon, Elise [3 ]
Vladimir Oliveira, J. [1 ]
Ninow, Jorge L. [1 ]
Hense, Haiko [1 ]
Oliveira, Debora [1 ]
机构
[1] Univ Fed Santa Catarina, BR-88040900 Florianopolis, SC, Brazil
[2] Univ Estadual Estado Mato Grosso, UNEMAT, BR-78390000 Barra Do Bugres, MT, Brazil
[3] Oniris Nantes, Ecole Natl Vet Agroalimentaire & Alimentat, F-44322 Nantes 3, France
关键词
Lipozyme TL IM; Antimicrobial activity; Eugenyl acetate; Acetylation; FREE SYSTEM; ESTERIFICATION; LIPASE; ACID; CLOVES;
D O I
10.1007/s12010-015-1611-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The ability of commercial immobilized lipase from Thermomyces lanuginosus (Lipozyme TL IM) to catalyze the acetylation of essential clove oil with acetic anhydride in a solvent-free system was studied, and the antimicrobial activity of the ester formed was evaluated as well. Experimental design based on two variables (eugenol to acetic anhydride molar ratio and temperature) was employed to evaluate the experimental conditions of eugenyl acetate ester production. The maximum conversion yield (92.86 %) was obtained using Lipozyme TL IM (5 wt%, based on the total amount of substrates), with eugenol to acetic anhydride molar ratio of 1:5 at 70 A degrees C. The chemical structure of the eugenyl acetate ester obtained at the optimized condition, and purified, was confirmed by the proton nuclear magnetic resonance (H-1-NMR) analysis. The antimicrobial activity of eugenyl acetate ester was proven effective on Gram-positive and Gram-negative bacteria, with means of 16.62 and 17.55 mm of inhibition halo.
引用
收藏
页码:782 / 795
页数:14
相关论文
共 50 条
  • [21] Highly Atom-Economic, Catalyst-Free, and Solvent-Free Synthesis of Phthalazinones
    Lu, Bowei
    Xie, Zhiqiang
    Lu, Junrui
    Liu, Jinbiao
    Cui, Siqian
    Ma, Yao
    Hu, Xinlong
    Liu, Yue
    Zhong, Kaikai
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (01) : 134 - 138
  • [22] Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
    Abdol Reza Hajipour
    Hirbod Karimi
    Morteza Karimzadeh
    Monatshefte für Chemie - Chemical Monthly, 2014, 145 : 1461 - 1472
  • [23] Phosphomolybdic acid: Mild and efficient catalyst for acetylation of alcohols, phenols, and amines under solvent-free conditions
    Kadam, Santosh T.
    Kim, Sung Soo
    SYNTHESIS-STUTTGART, 2008, (02): : 267 - 271
  • [24] Cinnamyl acetate synthesis by lipase-catalyzed transesterification in a solvent-free system
    Geng, Bo
    Wang, Mengfan
    Qi, Wei
    Su, Rongxin
    He, Zhimin
    BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY, 2012, 59 (04) : 270 - 275
  • [25] Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
    Hajipour, Abdol Reza
    Karimi, Hirbod
    Karimzadeh, Morteza
    MONATSHEFTE FUR CHEMIE, 2014, 145 (09): : 1461 - 1472
  • [26] Acetylation of Bacterial Cellulose Using N-Methylimidazole as a Catalyst Under Solvent-free and N,N-dimethylacetamide/Lithium Chloride Solvent Systems
    Wu, Jian
    Tao, Yanlei
    Geng, Alei
    Xie, Rongrong
    Zhu, Daochen
    Wang, Qianqian
    Sun, Lushan
    Sun, Jianzhong
    BIORESOURCES, 2020, 15 (02) : 3688 - 3706
  • [27] Efficient Solvent-Free Synthesis of Phytostanyl Esters in the Presence of Acid-Surfactant-Combined Catalyst
    He, Wen-Sen
    Ma, Yuan
    Pan, Xiao-Xia
    Li, Jing-Jing
    Wang, Mei-Gui
    Yang, Ye-Bo
    Jia, Cheng-Sheng
    Zhang, Xiao-Ming
    Feng, Biao
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (38) : 9763 - 9769
  • [28] Modified Silico-Tungstate: An Easy and Efficient Catalyst for the Acetylation of Amines Under Solvent-Free Condition
    R. K. Sharma
    Deepti Rawat
    Journal of Inorganic and Organometallic Polymers and Materials, 2010, 20 : 698 - 705
  • [29] Synthesis and Properties of Ascorbyl Esters Catalyzed by Lipozyme TL IM using Triglycerides as Acyl Donors
    Reyes-Duarte, D.
    Lopez-Cortes, N.
    Torres, P.
    Comelles, F.
    Parra, J. L.
    Pena, S.
    Ugidos, A. V.
    Ballesteros, A.
    Plou, F. J.
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2011, 88 (01) : 57 - 64
  • [30] Solvent-free acetylation of cellulose nanofibers for improving compatibility and dispersion
    Ashori, Alireza
    Babaee, Mehran
    Jonoobi, Mehdi
    Hamzeh, Yahya
    CARBOHYDRATE POLYMERS, 2014, 102 : 369 - 375