An efficient countercurrent distribution method for the large-scale isolation of dimorphecolic acid methyl ester

Add time:07/22/2019    Source:sciencedirect.com

Effective procedures are reported for isolating and producing dimorphecolic acid (1) and its methyl ester (2) from Dimorphotheca pluvialis seed oil. The methods are suitable even for kilogram-scale production. The acid 1 was prepared by enzymatic hydrolysis of the oil and isolated by crystallization at low temperature. The ester (2) was obtained by methoxide-catalyzed transesterification of the glycerides followed by a countercurrent separation using four vessels and fourteen transfers with the two-phase system 90% aq. methanol-hexane. Methyl 9-oxo-10,12-E,E-octadecadienoate (3) (0.5 to 4%) was observed by GC and GC-MS and characterized by its reduction with sodium borohydride to racemic 2 and by its formation from 2 by Oppenauer oxidation. The complete assignment of the 1H and 13C-NMR signals of 1 and 3 has been carried out using 2D homonuclear and heteronuclear NMR experiments.

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