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Method for preparing phosphatidic acid phospholipid compound by two-step method

A technology for polyenoic acid phospholipids and compounds is applied in the field of preparation of polyenoic acid phospholipids, can solve problems such as unfavorable large-scale production, and achieve the effects of low synthesis cost, simple preparation process and mild reaction conditions

Inactive Publication Date: 2017-06-23
THIRD INST OF OCEANOGRAPHY STATE OCEANIC ADMINISTATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the synthesis methods of the above two polyenoic acid phospholipids require the use of highly hydrolyzed P 2 o 5 or oxalyl chloride, and the operation requires strict anhydrous, otherwise the reaction cannot be carried out. At the same time, catalysts and some toxic organic solvents need to be added, which is not conducive to large-scale industrial production

Method used

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  • Method for preparing phosphatidic acid phospholipid compound by two-step method
  • Method for preparing phosphatidic acid phospholipid compound by two-step method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] In a 200mL three-necked flask, add 0.1mol (7.5g) of 3-amino-1-propanol and 0.1mol (13.8g) of diethyl phosphite and place it in a low-temperature cooling pump at 0°C. While stirring, Slowly add 1.25mol (92.5g) sodium hypochlorite aqueous solution dropwise (the density is calculated as 1.0g / mL, and the NaClO content is calculated as 8%). After the reaction is completed, extract once with ethyl acetate, dry, and concentrate to obtain 8.6g (O, O) -Diethylphosphorylated-3-amino-1-propanol intermediate, ready to use. In another 100mL round bottom flask, add 0.03mol (10g) polyenoic acid (i.e. fatty acid mixture containing n-3 unsaturated hydrocarbon groups with 20 to 22 carbon atoms) and 0.03mol (6.33g) of the above-mentioned intermediate product, place At room temperature, under the condition of stirring, 0.036mol (7.42g) N,N-dicyclohexylcarbodiimide (DCC) solution dissolved in 30mL ethyl acetate was slowly added dropwise. After the reaction was completed, the solid N was rem...

Embodiment 2

[0026] In a 200mL three-necked flask, add 0.1mol (7.5g) 3-amino-1-propanol and 0.1mol (13.8g) diethyl phosphite and place it in a low-temperature cooling pump at 5°C, while stirring, Slowly add 1.0mol (74g) sodium hypochlorite aqueous solution dropwise (the density is calculated as 1.0g / mL, and the NaClO content is calculated as 8%). After the reaction is completed, extract once with ethyl acetate, dry, and concentrate to obtain 7.2g (O, O)- Diethylphosphorylated-3-amino-1-propanol intermediate, ready to use. In another 100mL round bottom flask, add 0.03mol (10g) polyenoic acid (i.e. fatty acid mixture containing n-3 unsaturated hydrocarbon groups with 20 to 22 carbon atoms) and 0.03mol (6.33g) of the above-mentioned intermediate product, place At room temperature, under the condition of stirring, slowly add 0.033mol (6.80g) DCC solution dissolved in 30mL ethyl acetate dropwise, after the reaction, remove the solid N,N-dicyclohexyl urea to obtain the target product polyenoic a...

Embodiment 3

[0028] In a 20L glass reactor bottle, add 10mol (750g) 3-amino-1-propanol and 10mol (1380g) diethyl phosphite, adjust the temperature of the low-temperature cooling circulation pump to make the temperature of the reaction solution in the kettle lower than 5°C, and Under the situation of stirring, slowly add dropwise 120mol (8.9kg) sodium hypochlorite aqueous solution (density is calculated by 1.0g / mL, and NaClO content is calculated by 8%), after the reaction finishes, ethyl acetate extracts once, is dried, concentrates and obtains 703g (O , O)-diethylphosphorylated-3-amino-1-propanol intermediate product for use. In another 5L Erlenmeyer flask, add 3mol (1kg) polyenoic acid (i.e. fatty acid mixture containing n-3 unsaturated hydrocarbon groups of 20 to 22 carbon atoms) and 3mol (633g) of the above-mentioned intermediate product, place at room temperature, Under the situation of stirring, slowly add dropwise the 4.2mol (865g) DCC solution that is dissolved in 1200mL ethyl acet...

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Abstract

The invention provides a method for preparing a phosphatidic acid phospholipid compound by a two-step method. The method comprises the following two steps: step 1, preparing 3-amino-1-propanol and diethyl phosphate into (O,O)-diethylphosphorylation-3-amino-1-propanol under the action of NaClO; step 2, preparing phosphatidic acid and diethylphosphorylation-3-amino-1-propanol into a target product under the action of DCC, namely the phosphatidic acid phospholipid compound. The method provided by the invention has the advantages of being simple in preparation process, mild in reaction conditions and low in synthesis cost, and the use of harmful CCl4, triethylamine and other organic reagents is avoided; meanwhile, a technical route for reaction can be suitable for preparation of kilogram-scale pilot test, which is the efficient, convenient and rapid method for preparing the phosphatidic acid phospholipid compound.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a method for preparing polyenoic acid phospholipid compounds using a two-step method, in particular to a method for preparing polyenoic acid phospholipid compounds with simple preparation process, mild reaction conditions and low synthesis cost. Background technique [0002] Phospholipids widely exist in animal and plant tissues and microorganisms, and are the main components of cell membranes and nerve tissues. Phospholipids are divided into animal sources, plant sources and microbial sources according to their sources. At present, soybean phospholipids and egg yolk phospholipids are two main products in the domestic phospholipid market, but the unsaturated fatty acids contained in them are mainly oleic acid (C18:1), linoleic acid (C18:2) and linolenic acid (C18: 3) and so on, the degree of unsaturation is relatively low, and the content of n–3 polyenoic acids (PUFAs) ...

Claims

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Application Information

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IPC IPC(8): C07F9/24
CPCC07F9/2408C07F9/2458
Inventor 方华黄晓燕张怡评晋文慧洪专
Owner THIRD INST OF OCEANOGRAPHY STATE OCEANIC ADMINISTATION
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