Abstract
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.
Similar content being viewed by others
References
Baldioli, M., Servili, M., Perretti, G. and Montedoro, G.F. (1996), J. Am. Oil Chem. Soc., 73, 1589-1593
Baraldi, P.G., Simoni, D., Mantredini F. and Menziani, E. (1983), Liebigs Ann. Chem. 684-686
Bierman, C.J., McGinnis, G.D. (1989). Analysis of Carbohydrates by GLC and MS, CRC Press, Florida, pp 88-92
Chen, Q., Huang, S. and Ho, C.-T., (1992), J. Am. Oil Chem. Soc., 69, 999
Guyot, B., Bosquette, B., Pina, M. and Graille, J. (1997), Biotech. Lett. 19, 529-532
Habulin, M., Krmelj, V. and Knez, Z. (1996), J. Agric. Food Chem., 44, 338-342
Laane, C., Boeren, S., Vos, K. and Veeger, C. (1987), Biotechnol. Bioeng. 30:81-87
Macrae, A.R., Bosley, J.A. and Peilow, A.D. (1988), European Patent EP 0322213
McMurry, J. (1984). In Organic Chemistry, Brooks/Cole Publishing Company, Chapter 29, Arylamines and Phenols pp 980-986
Packer, L. (1996). In: Proceedings of the International Symposium on Natural Antioxidants: Molecular Mechanisms and Health Effects(Packer, L., Traber, M.G. and Xin, W., eds.), AOCS Press Champaign, IL, pp 9-23
Papadopoulos, G. and Boskou, D. (1991), J. Am. Oil Chem. Soc., 68, 669-671
Shahidi, F. (1997) In: Natural Antioxidants: Chemistry, Health and Applications, Ed. AOCS Press, Champaign, Illinois and references cited therein
Uppenberg, J., O[:]hrner, N., Norin, M., Hult, K., Kleytwegt, G.J., Patkar, S., Waagen, V., Anthonsen, T. and Jones, T.A. (1995), Biochemistry, 34, 16838-16851
Valivety, R.H., Johnson, G.A., Suckling, C.J. and Halling (1991), Biotechnol. Bioeng. 38:1137-1143
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Buisman, G., van Helteren, C., Kramer, G. et al. Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants. Biotechnology Letters 20, 131–136 (1998). https://doi.org/10.1023/A:1005368222340
Issue Date:
DOI: https://doi.org/10.1023/A:1005368222340