Synthesis and surface properties of monoeicosapentaenoyl trehalose

European Food Research and Technology (Impact Factor: 1.39). 229(3):403-408. DOI: 10.1007/s00217-009-1049-5

ABSTRACT Eicosapentaenoyl trehalose was transesterified with eicosapentaenoic acid ethyl ester and trehalose in tert-butanol using microbial lipase. Reversed phase high-performance liquid chromatography coupled with diode array detection
and electrospray ionization mass spectrometry (RPHPLC-DAD–ESI-MS) analysis showed that the monoester and diester existed in
the reaction mixture. Silica gel column chromatography was adopted to pretreat the reactive mixture then the eluted monoeicosapentaenoyl
trehalose was further purified using semi-preparative HPLC. The structure of the compound was confirmed by ESI-MS and nuclear
magnetic resonance (NMR) as 6-O-monoeicosapentaenoyl trehalose. Subsequently, the surface properties of monoeicosapentaenoyl trehalose were investigated.
The results indicated that the surface tension, CMC, γCMC and ΔG
mico decreased with increasing temperature, however, the area occupied per molecule increased very little.

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