Synthesis of acyl alanine methyl ester gelator and assessment of its gelation factors

叶连宝; 秦凌浩; 王晓明; 胡巧红

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Synthesis of acyl alanine methyl ester gelator and assessment of its gelation factors

更新时间：2026-01-09

- Synthesis of acyl alanine methyl ester gelator and assessment of its gelation factors
- Journal of Army Medical University Vol. 34, Issue 14, Pages: 1397-1400(2012)
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  CLC： R914.5;R917;R961
- Published：2012
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叶连宝,秦凌浩,王晓明,胡巧红.脂酰丙氨酸酯同系凝胶因子的合成与成胶因素的评价[J].陆军军医大学学报(原第三军医大学学报),2012,34(14):1397-1400.

　Ye Lianbao,Qin Linghao,Wang Xiaoming,Hu Qiaohong.Synthesis of acyl alanine methyl ester gelator and assessment of its gelation factors[J].J Amry Med Univ (J Third Mil Med Univ),2012,34(14):1397-1400.
叶连宝,秦凌浩,王晓明,胡巧红.脂酰丙氨酸酯同系凝胶因子的合成与成胶因素的评价[J].陆军军医大学学报(原第三军医大学学报),2012,34(14):1397-1400. DOI：

　Ye Lianbao,Qin Linghao,Wang Xiaoming,Hu Qiaohong.Synthesis of acyl alanine methyl ester gelator and assessment of its gelation factors[J].J Amry Med Univ (J Third Mil Med Univ),2012,34(14):1397-1400. DOI：

摘要

目的合成十四、十六、十八酰丙氨酸甲酯，并对其胶凝能力进行考察。方法以丙氨酸甲酯，十四、十六、十八酰氯为原料，合成十四、十六、十八酰丙氨酸甲酯，采用IR、

H-NMR、MS确证其结构，对不同溶剂、不同温度及不同链长的胶凝能力进行研究。结果该类凝胶因子可以在大多数的有机溶剂中形成凝胶，十四、十六、十八酰丙氨酸甲酯在注射用大豆油和中链脂肪酸三甘酯（medium chain triglycerides

MCT）中的最低成胶浓度分别为11.9、7.2、8.5 mg/ml和18.7、12.3、13.4 mg/ml；3种凝胶因子在大豆油中的胶凝焓变分别为74.74、51.70 kJ/mol和61.61 kJ/mol。结论合成得到目标化合物具有较好的胶凝能力，可以作为局部给药的长效药物载体。

Abstract

Objective To synthesize the N-tetradecanoyl

N-hexadecanoyl and N-octadecanoyl alanine methyl ester gelators and investigate their gelation ability. Methods N-tetradecanoyl

N-hexadecanoyl and N-octadecanoyl alanine methyl ester gelators were synthesized using alanine methyl ester

N-tetradecanoyl chloride

N-hexadecanoyl chloride and N-octadecanoyl chloride. Chemical structures of the gelators were confirmed by MS

and

H-NMR

respectively. Gelation ability of different solvents，temperatures and chain lengths was studied. Results The synthesized N-tetradecanoyl

N-hexadecanoyl and N-octadecanoyl alanine methyl ester gelators could produce gel in many organic solvents.

Their minimum gel concentration in soybean oil and medium chain triglycerides(MCT) was 11.9

7.2

8.5 mg/ml and 18.7

12.3

13.4 mg/ml

respectively

and their enthalpy (ΔH) in soybean oil was 74.741

51.70 kJ/mol and 61.61 kJ/mol

respectively. Conclusion The synthesized N-tetradecanoyl

N-hexadecanoyl and N-octadecanoyl alanine methyl ester gelators have a good gelation ability

and can thus be used as a local long-acting drug carrier.

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