Premium
Lipase‐Catalyzed Esterification of Triterpene Alcohols and Phytosterols with Oleic Acid
Author(s) -
Kobayashi Takashi,
Ogino Akane,
Miyake Yasuhito,
Mori Hajime,
Hosoda Asao,
Fujita Muneki,
Tsuno Takuo,
Adachi Shuji
Publication year - 2014
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/s11746-014-2531-1
Subject(s) - chemistry , oleic acid , substrate (aquarium) , triterpene , yield (engineering) , catalysis , organic chemistry , chromatography , candida rugosa , lipase , high performance liquid chromatography , biochemistry , enzyme , medicine , oceanography , alternative medicine , materials science , pathology , metallurgy , geology
Oleic acid esters of phytosterols (PSs) and triterpene alcohols (TAs), derived from rice bran, were synthesized using lipases under mild conditions. Some lipases, especially from Candida rugosa , type VII, showed very high substrate specificity towards both PSs and TAs, when a mixture of PS and TA (PS/TA mixture) was used as the substrate source. The maximum yield of PS esters was ca. 80 % in each case; however, the maximum yield of TA esters was much lower when the reaction was continued for 7 days. Due to the difficulty in purifying the esters obtained when the PS/TA mixture was used as source of substrate, free PSs and TAs were separated from the PS/TA mixture by silica‐gel and reverse‐phase chromatography prior to esterification. The pure PSs or TAs were esterified with oleic acid to obtain the corresponding esters with high purity. Differential scanning calorimetric analysis of the resulting esters revealed that their melting points ranged from 7.0 to 42 °C. These values were at least 100 °C lower than those of the free PSs and TAs.