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Amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine and preparation method thereof

A surfactant and phosphorylcholine technology, applied in chemical instruments and methods, transportation and packaging, dissolution, etc., can solve the problems of high cytotoxicity, inability to be used, unfavorable use, etc., and achieve simple preparation process, easy acquisition, easy-to-handle effects

Active Publication Date: 2012-07-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common amphiphilic small molecule surfactants widely used at present, such as sodium dodecylbenzene sulfonate, n-tetraoctyl ammonium bromide, etc., have many disadvantages: First, the hydrophobic part often uses straight-chain alkyl
This makes the electrostatic repulsion between the aggregates in the aqueous solution easy to be shielded by other ions in the solution, causing the surfactant to precipitate out of the solution, so it is not conducive to use in water with high salinity
In addition, low-molecular-weight oligoethylene glycol-based nonionic surfactants were reported to be too cytotoxic to be used in biomedical applications

Method used

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  • Amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine and preparation method thereof
  • Amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine and preparation method thereof
  • Amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0044] The preparation method of the amphiphilic small molecule surfactant based on cholesterol and phosphorylcholine comprises the following steps:

[0045] 1) Add 1mol cholesterol to 1mL~5×10 4 In a mixed solvent of methylene chloride and pyridine, the volume ratio of methylene chloride and pyridine is 100 / 1 to 1 / 100, 1 to 20 mol of p-toluenesulfonyl chloride is added, and 0.01 mol to 1 mol of 4-dimethylaminopyridine is added as a catalyst, Stir the reaction at 0°C to 100°C for 0.5h to 100h, remove the solvent by vacuum distillation, and recrystallize the obtained solid twice in acetone to obtain cholesterol p-toluenesulfonate. The reaction formula is:

[0046]

[0047] 2) Dissolve 1mol cholesterol p-toluenesulfonate in 1mL~6×10 4 To mL dioxane, add 1mol~50mol aliphatic straight-chain double-terminated diol, under the protection of argon or nitrogen, react at 50℃~200℃ for 4h~100h, remove the solvent by vacuum distillation, add 1mL ~6×10 4 mL dichloromethane, followed b...

Embodiment 1

[0063] Example 1: The product molecule obtained in this example has the following structure

[0064]

[0065] m=6, n=2

[0066] 1) Add 100g of cholesterol to a mixed solvent of 500mL of dichloromethane and 500mL of pyridine, then add 117g of p-toluenesulfonyl chloride, and then add 4.3g of 4-dimethylaminopyridine as a catalyst, and stir the solution at 25°C for 72 hour, the solvent was removed by vacuum distillation, and the resulting solid was recrystallized twice in acetone to obtain cholesterol p-toluenesulfonate, whose reaction formula is:

[0067]

[0068] 2) Dissolve 21.63g of cholesterol p-toluenesulfonate in 300mL of dioxane, then add 23.63g of 1,6-hexanediol, make the reaction solution under the protection of argon or nitrogen, and react at 120°C for 72 hours, the solvent was distilled off in vacuo, and 200 mL of dichloromethane was added to dissolve the resulting solid, followed by saturated NaHCO 3 aqueous solution and saturated brine for 2 washes respective...

Embodiment 2

[0078] Embodiment 2: The product molecule that this embodiment obtains is following structure

[0079]

[0080] m=10, n=2

[0081] Step 1) is identical with step 1) in embodiment 1;

[0082] 2) 26g of cholesterol p-toluenesulfonate was dissolved in 300mL of dioxane, then 36g of 1,10-decanediol was added, and the reaction solution was reacted at 120°C for 72 hours under the protection of argon or nitrogen, The solvent was then vacuum distilled off, 200 mL of dichloromethane was added to dissolve the resulting solid, and saturated NaHCO 3 aqueous solution and saturated brine for 3 times respectively, and then anhydrous Na was added to the dichloromethane solution 2 SO 4 Remove water, remove the dichloromethane solvent by rotary evaporation, and use silica gel column chromatography to separate and purify the obtained solid. The developing solvent is a mixed solvent of dichloromethane / ethyl acetate, and the volume ratio is 15 / 1. In addition to obtaining a white solid, its r...

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Abstract

The invention discloses an amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine and a preparation method thereof. The amphiphilic small molecular surfactant has the following advantages that the prepared small molecular surfactant utilizes biomolecules cholesterol and phosphorylcholine as the structural elements and has good biocompatibility; in the preparation process, the properties of the amphiphilic small molecule can be adjusted by changing the length of linear alkyl between the hydrophilic and hydrophobic parts and the distances between centers of charges in phosphorylcholine groups; the small molecular surfactant has good hydrophilicity, the formed aqueous solution has stable properties, is not easy to damage due to impacts of change of the pH value in the water environment and change of ionic strength and can be used under wide conditions; and the small molecular surfactant has cheap preparation raw materials, simple and convenient technology and higher yield; therefore the amphiphilic small molecule has very broad application prospects in the biomedical field and in the aspect of cosmetic, food, nano particle preparation and the like. The amphiphilic small molecular surfactant based on cholesterol and phosphorylcholine has the molecule structural formula shown in the specification, wherein in the formula, m is equal to 2-20 and n is equal to 2-8.

Description

technical field [0001] The invention relates to an amphiphilic small molecule surfactant and a preparation method thereof, in particular to an amphiphilic small molecule surfactant based on cholesterol and phosphorylcholine and a preparation method thereof. Background technique [0002] There are many kinds of amphiphilic small molecule surfactants. They can form certain forms of aggregates in water, such as micelles, vesicles, etc., and can solubilize many hydrophobic substances in them. They are used in biomedical materials, cosmetics, food, etc. , nanoparticle preparation and other fields have a very wide range of applications. Common amphiphilic small molecule surfactants widely used at present, such as sodium dodecylbenzenesulfonate, n-tetraoctylammonium bromide, etc., have many disadvantages: First, straight-chain alkyl groups are often used for the hydrophobic part. It is well known that the stability of aggregates in solution is closely related to the strength of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/18B01F17/20C07J9/00C09K23/18C09K23/20
Inventor 计剑徐方明王海波沈家骢
Owner ZHEJIANG UNIV
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