Physicochemical Properties of Selectively Oxidized 1-Monolaurin from 2,2,6,6-Tetramethyl-1-Piperidinyl Oxoammonium Ion/Sodium Hypochlorite-Mediated Reaction
2009
Ahn, Seon Min | Lee, Hyong Joo | Kim, S-W (Sang-Woo) | Lee, JaeHwan | Chang, Pahn-Shick
The primary alcohol group of 1-monolaurin (1-ML) was selectively oxidized using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion/sodium hypochlorite (NaOCl) without NaBr at two different conditions. The selective oxidation occurred more efficiently at 35 °C and 32.2 mmol of NaOCl than at 25 °C and 18.7 mmol of NaOCl. Regioselective oxidation of the primary alcohol without oxidation of a secondary alcohol was confirmed by a chemical shift at 175 ppm and no resonance between 198 and 205 ppm in 13C NMR and the presence of a peak at 1560-1570 cm-1 in IR spectra. The water solubility of oxidized 1-monolaurin (OML) was remarkably increased by 33.2 times as compared to that of 1-ML. Creaming velocities resulting from fat flocculation in a 0.2% level of OML and 1-ML were 0.16 and 1.13 mm/h, respectively, implying that OML showed higher efficiency and emulsion stability in preventing fat flocculation than 1-ML due to the selective oxidation of primary alcohol.
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