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Synthesis of N-stearyl tyrosine salts and measurement of its critical micelle concentration

TANG Shuang-qi, YIN Sha, LU Yang   

  1. Laboratory of Chemical Biology, Basic Medicine Faculty of Shanghai Jiao Tong University, Shanghai 200025, China
  • Online:2014-06-28 Published:2014-06-30
  • Supported by:

    National Natural Science Foundation of China, 30873057, 81171245; Key Basic Research Project of Science and Technology Commission of Shanghai Municipality, 11JC1406600; Scientific and Technological Support Project of Science and Technology Commission of Shanghai Municipality, 12431900604

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Abstract:

Objective To synthesize N-stearyl tyrosine disodium (NST-2Na) and dipotassium (NST-2K) and to determine their critical micelle concentration (CMC). Methods N-stearyl tyrosine (NST) was synthesized from stearic acid via two step reactions and then basified by NaOH or KOH to obtain the target compounds. The feasibility of UV spectrophotometry for measuring the CMC was determined by the CMC trial of sodium dodecyl sulfate (SDS) and N,N-diethyl aniline (DEA) was used as the probe. The CMC of two NST salts was measured by the UV spectrophotometry. Results The results of high performance liquid chromatography (HPLC) showed that the purity of NST-2Na and NST-2K was 98.35% and 92.65%, respectively. The CMC values of SDS determined by the UV spectrophotometry were consistent with those of literatures. The CMC was 27.5 mg/100 mL for NST-2Na and 25.0 mg/100 mL for NST-2K. Conclusion The UV spectrophotometry is a simple and reliable method for measuring the CMC of NST salts.

Key words: sodium dodecyl sulfate, N-stearyl tyrosine salts, N,N-diethyl aniline, UV spectrophotometry, critical micelle concentration