TY - JOUR
T1 - Chemoenzymatic solvent-free synthesis of 1-monopalmitin using a microwave reactor
AU - Torregrosa, Rubén
AU - Balcells, Mercé
AU - Torres, Mercé
AU - Canela-Garayoa, Ramon
PY - 2014/8
Y1 - 2014/8
N2 - An environmentally friendly method for the synthesis of 1-monopalmitin has been developed. The procedure consists of a two-step, solvent-free chemoenzymatic reaction. In the first step, palmitic acid is esterified with solketal (4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane) using Novozym 435 by both conventional heating and microwave irradiation. The use of a microwave reactor allows the enzymatic synthesis of the intermediate compound with a similar yield as that achieved using conventional heating. In the second step, 1,2-acetonide-3-palmitoyl glycerol is cleaved to yield 1-monopalmitin by means of a cation-exchange resin and water or aliphatic alcohols as hydrolytic reagent in solvent-free conditions. The hydrolysis was accomplished in 15 min at 85°C. The best yield was obtained using 1-pentanol. We conclude that the yield achieved depends on the batch and nature of the cation-exchange resin used as catalyst.
AB - An environmentally friendly method for the synthesis of 1-monopalmitin has been developed. The procedure consists of a two-step, solvent-free chemoenzymatic reaction. In the first step, palmitic acid is esterified with solketal (4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane) using Novozym 435 by both conventional heating and microwave irradiation. The use of a microwave reactor allows the enzymatic synthesis of the intermediate compound with a similar yield as that achieved using conventional heating. In the second step, 1,2-acetonide-3-palmitoyl glycerol is cleaved to yield 1-monopalmitin by means of a cation-exchange resin and water or aliphatic alcohols as hydrolytic reagent in solvent-free conditions. The hydrolysis was accomplished in 15 min at 85°C. The best yield was obtained using 1-pentanol. We conclude that the yield achieved depends on the batch and nature of the cation-exchange resin used as catalyst.
KW - 1-Monopalmitin
KW - Cation-exchange resin
KW - MAG
KW - Microwave
KW - Solvent-free reaction
UR - http://www.scopus.com/inward/record.url?scp=84906655205&partnerID=8YFLogxK
U2 - 10.1177/1934578x1400900809
DO - 10.1177/1934578x1400900809
M3 - Article
C2 - 25233581
AN - SCOPUS:84906655205
SN - 1934-578X
VL - 9
SP - 1095
EP - 1098
JO - Natural Product Communications
JF - Natural Product Communications
IS - 8
ER -