Premium
Lipase‐catalyzed synthesis of triolein‐based sunscreens in supercritical CO 2
Author(s) -
Compton David L.,
King Jerry W.
Publication year - 2001
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-001-0217-z
Subject(s) - triolein , transesterification , supercritical fluid , chemistry , yield (engineering) , toluene , glycerol , organic chemistry , lipase , catalysis , nuclear chemistry , chromatography , materials science , enzyme , metallurgy
Novozym ® 435‐catalyzed transesterification of ethyl 4‐hydroxy‐3‐methoxy cinnamate (ethyl ferulate, EF) with triolein to form the ultraviolet (UV)‐absorbing lipids monoferuloylmonooleoyl‐glycerol (FMO) and feruloyl‐dioleoyl‐glycerol (FDO) has been conducted using supercritical CO 2 (SC−CO 2 ) batch reactions. The alcoholysis of 0.1 M EF with 0.1 M 1‐octanol in SC−CO 2 to form octyl ferulate was used as a model reaction to optimize pressure and temperature conditions. Conditions ranging from 45 to 80°C and 10.3 to 34.5 MPa (1,500 to 5,000 psi) were tested with a maximal conversion of 53% of the EF being achieved at 13.8 MPa (2,000 psi) and 80°C after 24 h. These optimized conditions applied to the transesterification of EF with triolein effected a combined FMO and FDO yield of 69%. Triolein exhibits higher solubilities in SC−CO 2 at higher pressures; therefore, the transesterification was performed at 80°C over a range of pressures from 13.8 to 34.5 MPa (2,000 to 5,000 psi). Results showed that a maximal yield of 74% of FMO and FDO was reached at 80°C and 24.1 MPa (3,500 psi) after 48 h. Compared to the FMO and FDO synthesis conducted neat or in toluene, the synthesis of the UV‐absorbing lipids in SC−CO 2 affords higher yields within a shorter amount of time. Therefore, the transesterification of EF with triolein in a SC−CO 2 batch reaction is a viable route to UV‐absorbing lipids that could be used as active ingredients in sunscreen formulations.