Physicochemical properties of selectively oxidized 1-monolaurin from 2,2,6,6-tetramethyl-1-piperidinyl oxoammonium ion/sodium hypochlorite-mediated reaction.
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 degrees C and 32.2 mmol of NaOCl than at 25 degrees 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 (13)C 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.
Ahn
Seon Min
SM
Technical Research Institute, Dong Suh Foods Co., Incheon 411-1, Korea.
Lee
Hyong Joo
HJ
Kim
Sang Woo
SW
Lee
Jaehwan
J
Chang
Pahn-Shick
PS
D055598:Chemical Phenomena; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004655:Emulsions / Q000737:chemistry; D007848:Laurates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D050178:Monoglycerides / Q000737:chemistry*; D010084:Oxidation-Reduction; D012973:Sodium Hypochlorite / Q000737:chemistry*; D012995:Solubility; D013055:Spectrophotometry, Infrared; D014867:Water
D003497:Cyclic N-Oxides; D004655:Emulsions; D007848:Laurates; D050178:Monoglycerides; D014867:Water; C020777:monolaurin; D012973:Sodium Hypochlorite; C003959:TEMPO