TY - JOUR
T1 - The synthesis of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase
AU - Haraldsson, Gudmundur G.
AU - Gudmundsson, Birgir Ö
AU - Almarsson, Örn
N1 - Funding Information: The authors would like to express their gratitude to Lysi Ltd of Iceland and Novo Nordisk A/S in Denmark for financial support, to Baldur Hjaltason at Lysi, Tomas T. Hansen and Hanne Svanholm at Novo Nordisk for useful discussions, Dr. Sigridur J6nsd6ttir at the Science Institute who ran the NMR analysis and, f'mally, Dr. Philip Page at the University of Liverpool, U.K., for mass spectrometry analysis.
PY - 1995/1/16
Y1 - 1995/1/16
N2 - A highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described. Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99 % EPA or DHA as ethyl esters and free fatty acids, respectively. Both processes were performed under vacuum at 65°C in the absence of any solvent. The volatile co-products were condensed into a cooled trap, thus shifting the equilibrium toward completion. Complete incorporation was reached in less than 72 h for all cases, but the direct esterification was found to proceed considerably faster than the transesterification as were both processes involving EPA as compared to DHA. High-field 1H NMR spectroscopy analysis offered detailed investigation of the intermediate glycerides during the direct esterification reaction. The purity of the resulting crude products which were afforded in excellent yields was very high.
AB - A highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described. Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99 % EPA or DHA as ethyl esters and free fatty acids, respectively. Both processes were performed under vacuum at 65°C in the absence of any solvent. The volatile co-products were condensed into a cooled trap, thus shifting the equilibrium toward completion. Complete incorporation was reached in less than 72 h for all cases, but the direct esterification was found to proceed considerably faster than the transesterification as were both processes involving EPA as compared to DHA. High-field 1H NMR spectroscopy analysis offered detailed investigation of the intermediate glycerides during the direct esterification reaction. The purity of the resulting crude products which were afforded in excellent yields was very high.
UR - https://www.scopus.com/pages/publications/0028837959
U2 - 10.1016/0040-4020(94)00983-2
DO - 10.1016/0040-4020(94)00983-2
M3 - Article
SN - 0040-4020
VL - 51
SP - 941
EP - 952
JO - Tetrahedron
JF - Tetrahedron
IS - 3
ER -