Gp. Mcneill et Pe. Sonnet, LOW-CALORIE TRIGLYCERIDE SYNTHESIS BY LIPASE-CATALYZED ESTERIFICATIONOF MONOGLYCERIDES, Journal of the American Oil Chemists' Society, 72(11), 1995, pp. 1301-1307
Monoglycerides of erucic acid (C-22:1, Delta 13), prepared by conventi
onal methods were reacted with caprylic acid (octanoic acid, C-8:0) by
using lipases as catalysts with the intention of synthesizing a trigl
yceride that contains two molecules of caprylic acid and one molecule
of erucic acid (caprucin). The reaction was carried out by mixing lipa
se powder, a small quantity of water, and the reactants in a temperatu
re-controlled stirred batch reactor. Organic solvents or emulsifying a
gents were not required. When the nonspecific lipase from Pseudomonas
cepacia was used, a yield of approximately 37% caprucin was obtained,
together with a complex mixture of di- and triglycerides that resulted
from the random transesterification of the erucic acid. The fatty aci
d-specific lipase from Geotrichum candidum promoted minimal transester
ification of erucic acid and resulted ina yield of 75% caprucin and ap
prox approximately 10% interesterification products. Lipase from Candi
da rugosa exhibited a similar, although less pronounced, specificity t
o that from G. candidum and promoted more transesterification of eruci
c acid. Optimum conditions for G. candidum lipase were at 50 degrees C
and an initial water content of 5.5%. After the reaction, erucic acid
was converted to behenic acid by hydrogenation, thereby converting ca
prucin into caprenin, a commercially available low-calorie triglycerid
e.