The crystal properties of cyclic nigerosyl-(1-6)-nigerose (CNN) and powdering of alpha-tocopherol, cholecalciferol and EPA using CNN

Cyclic nigerosyl-(1-6)-nigerose (CNN) has a unique structure consisting of four glucose residues connected by alternate alpha-(1-3)- and alpha-(1-6)-linkages. We investigated the crystal properties of CNN and the stability of powdered functional oils using CNN. As a result of thermal analysis, we found that CNN takes 3 crystal forms, 5H2O, 1H2O and anhydrous crystals. The alcohol retention capacity of variously cyclic saccharides, such as alpha-, beta- and gamma-cyclodextrin (CD), was also examined. Ethanol and propanol retention capacities were observed in the order beta-CD CNN beta-CD gamma-CD. We then examined the stability of powdered fat-soluble vitamins, vitamin Dsub(3), vitamin E and eicosapentaenoic acid, by using anhydrous CNN; CNN- functional oil powders showed the highest residual values. These results indicate that CNN is useful for powdering easily oxidized fat-soluble substances.