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KMID : 1007520040130020225
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Food Science and Biotechnology
2004 Volume.13 No. 2 p.225 ~ p.229
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Selective Oxidation of Primary Alcohol Group in 1-Monostearoyl Glycerol Mediated by 2,2,6,6-Tetramethyl-1-Piperidine Oxoammonium Ion
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Chang, Pahn-Shick
Seo, Hyun-Mi/Kwon, Oh-Taek/Lee, Hyeon-Gyu/Kim, Young-Suk
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Abstract
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Primary alcohol group of 1-monostearoyl glycerol (1-MS) was oxidized using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO)/sodium hypochlorite/sodium bromide at 25℃ and pH 10.8. Regio-selective oxidation of primary alcohol without oxidation of secondary alcohol group was confirmed by chemical shift at 175 ppm and no chemical shifts between 198-205 ppm in ^(13)C-NMR spectra, and a sharp peak at 1,600 cm^(-1) an IR spectra. Water solubility and dispersibility of the oxidized 1-MS increased from 0.5 to 7.3 ㎎/mL and from 42 to 90%, respectively. Emulsion formed by oxidized 1-MS had higher emulsion stability. Results revealed that oxidized 1-MS is more suitable for preparation of emulsion containing high concentration of water than for that containing oil.
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