Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants

被引:100
|
作者
Buisman, GJH [1 ]
van Helteren, CTW [1 ]
Kramer, GFH [1 ]
Veldsink, JW [1 ]
Derksen, JTP [1 ]
Cuperus, FP [1 ]
机构
[1] DLO, Agrotechnol Res Inst, ATO, NL-6700 AA Wageningen, Netherlands
关键词
D O I
10.1023/A:1005368222340
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Of seven lipases used to esterify functionalized phenols and fatty acids to synthesize lipophilic antioxidants, that from Candida antarctica lipase B (CAL-B) had the highest catalytic activity. Esterification yields of benzoic acid derivatives catalyzed by CAL-B are below 2% after 7 days. In contrast, relatively high yields were obstained for the esterification of (poly) phenols bearing primary hydroxy groups and aliphatic acids (85% yield within 15 hours). Crude products were purified and used as lipophilic antioxidants in sunflower oil.
引用
收藏
页码:131 / 136
页数:6
相关论文
共 50 条
  • [1] Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants
    G.J.H. Buisman
    C.T.W. van Helteren
    G.F.H. Kramer
    J.W. Veldsink
    J.T.P Derksen
    F.P. Cuperus
    [J]. Biotechnology Letters, 1998, 20 : 131 - 136
  • [2] Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants
    Stamatis, H
    Sereti, V
    Kolisis, FN
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1999, 76 (12) : 1505 - 1510
  • [3] Selective Enzymatic Esterification of Lignin-Derived Phenolics for the Synthesis of Lipophilic Antioxidants
    Martinez-Garcia, Marta
    Gracia-Vitoria, Jaime
    Vanbroekhoven, Karolien
    Dejonghe, Winnie
    Satyawali, Yamini
    [J]. ANTIOXIDANTS, 2023, 12 (03)
  • [4] Chemo-enzymatic synthesis and evaluation of novel structured phenolic lipids as potential lipophilic antioxidants
    Reddy, Kunduru Konda
    Shenker, Kaki Shiva
    Ravinder, Thumu
    Prasad, Rachapudi Badari Narayana
    Kanjilal, Sanjit
    [J]. EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2010, 112 (05) : 600 - 608
  • [5] The selective enzymatic synthesis of lipophilic esters of swainsonine
    Perrone, GG
    Barrow, KD
    McFarlane, IJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) : 831 - 835
  • [6] Novel methodologies for the synthesis of functionalized lipophilic carboranes
    Jonnalagadda, Subash C.
    Verga, Steven R.
    Patel, Parth D.
    Reddy, A. V.
    Srinivas, T.
    Scott, Patricia M.
    Mereddy, Venkatram R.
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (04) : 294 - 300
  • [7] Selective esterifications of alcohols and phenols through carbodiimide couplings
    Shelkov, R
    Nahmany, M
    Melman, A
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (03) : 397 - 401
  • [8] ALKYL PHENOLS AS ANTIOXIDANTS
    ROSENWALD, RH
    HOATSON, JR
    CHENICEK, JA
    [J]. INDUSTRIAL AND ENGINEERING CHEMISTRY, 1950, 42 (01): : 162 - 165
  • [9] Lipophilic antioxidants in patients with phenylketonuria
    Colomé, C
    Artuch, R
    Vilaseca, MA
    Sierra, C
    Brandi, N
    Lambruschini, N
    Cambra, FJ
    Campistol, J
    [J]. AMERICAN JOURNAL OF CLINICAL NUTRITION, 2003, 77 (01): : 185 - 188
  • [10] Lipophilic antioxidants in neurodegenerative diseases
    Chang, Kuo-Hsuan
    Cheng, Mei-Ling
    Chiang, Mu-Chun
    Chen, Chiung-Mei
    [J]. CLINICA CHIMICA ACTA, 2018, 485 : 79 - 87