Supercritical CO2 as a reaction medium for synthesis of capsaicin analogues by lipase-catalyzed transacylation of capsaicin.
Capsaicin analogues having different acyl moiety were synthesized by lipase-catalyzed transacylation of capsaicin with a corresponding acyl donor in supercritical CO2 as a reaction medium. Transacylation with methyl tetradecanoate using Novozym 435 as a catalyst gave vanillyl tetradecanamide in a 54% yield at 80 degrees C and 19 MPa over 72 h. Vanillyl (Z)-9-octadecenamide, olvanil, was synthesized from triolein in a 21% yield over 7 d.
School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan.
Kenji
K
Kobata
Mamiko
M
Kobayashi
Sachiyo
S
Kinpara
Tatsuo
T
Watanabe
D000123:Acetyltransferases / Q000737:chemistry*; D000215:Acylation; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry*; D012996:Solutions; D013379:Substrate Specificity; D013696:Temperature
D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D012996:Solutions; D002245:Carbon Dioxide; C054256:olvanil; D000123:Acetyltransferases; C093667:Novozyme 435; D008049:Lipase; D002211:Capsaicin