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One-pot method for preparing hydrophilic phytosterol/stanol derivative

A technology of phytostanols and phytosterols, which is applied in the field of preparation of hydrophilic phytosterols/stanols derivatives, can solve the problems of long reaction time and low product conversion rate, achieve low cost, high product purity, and improve Effects on Industrial Production Levels

Active Publication Date: 2017-05-31
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the only few methods involve cumbersome steps such as intermediate product separation and solvent removal, and have disadvantages such as long reaction time and low product conversion rate.

Method used

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  • One-pot method for preparing hydrophilic phytosterol/stanol derivative
  • One-pot method for preparing hydrophilic phytosterol/stanol derivative
  • One-pot method for preparing hydrophilic phytosterol/stanol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 Phytosterol polyethylene glycol succinate diester

[0039] 1. Preparation of phytosterol succinate monoester

[0040] Preparation method: Add 12.4g phytosterols, 3.0g succinic anhydride, and 0.25g ionic liquid 1-butylsulfonic acid-3-methylimidazolium bisulfate, respectively, into a reflux reaction device equipped with stirring and oil bath temperature control , add 100mL of petroleum ether, start stirring and adjust the temperature to 100-110°C, and react for 1-1.5h. The conversion rate of phytosterol succinate monoester can reach 98.7% as detected by HPLC. Add 10 mL of distilled water to the reaction solution, extract, collect the organic phase layer and remove the solvent by rotary evaporation to obtain 14.9 g of phytosterol succinate monoester.

[0041] Structural Identification: Phytosterol Succinate FT-IR: 2370-3700cm -1 The broad peak between them is the stretching vibration absorption of hydroxyl-OH in carboxyl-COOH (ν O-H ), 3030cm -1 Absorptio...

Embodiment 2

[0056] Embodiment 2 Phytostanol tea polyphenol adipate diester

[0057] 12.5g of phytostanol, 21.9g of adipic acid, and 1.0g of ionic liquid 1-propylsulfonic acid-3-methylimidazolium p-toluenesulfonate were respectively added to a reflux reaction equipped with stirring and oil bath temperature control. device, add 200mL of tert-butanol, start stirring and adjust the temperature to 80°C-85°C, and react for 2.5h-3h. Heating was stopped and 100 μL was sampled for HPLC analysis. The conversion rate of the intermediate product phytostanol adipate monoester can reach 95.3%.

[0058] After sampling, add 41.2g of hydrophilic modifier tea polyphenol, add 0g of ionic liquid 1-propylsulfonic acid-3-methylimidazolium p-toluenesulfonate, adjust the temperature to 80°C-85°C, and continue the reaction for 5h-6h. Heating was stopped and 100 μL was sampled for HPLC analysis. The conversion rate of the final product phytostanol tea polyphenol adipate diester can reach 92.9%.

[0059] After ...

Embodiment 3

[0060] Embodiment 3 Phytosterol maltitol suberate diester

[0061] Add 12.4g phytosterols, 7.8g suberic acid, and 0.36g ionic liquid 1-butylsulfonic acid-3-methylimidazolium trifluoromethanesulfonate, respectively, into the reflux reaction device equipped with stirring and oil bath temperature control , add 100mL of tert-amyl alcohol, start stirring and adjust the temperature to 100°C-105°C, and react for 1h-1.5h. Heating was stopped and 100 μL was sampled for HPLC analysis. The conversion rate of the intermediate product phytosterol suberate can reach 97.1%.

[0062] After sampling, add 20.6g of hydrophilic modifier maltitol, and add 0.24g of ionic liquid 1-butylsulfonic acid-3-methylimidazole trifluoromethanesulfonate, adjust the temperature to 100℃~105℃, and continue the reaction for 2h~ 3h. Heating was stopped and 100 μL was sampled for HPLC analysis. The conversion rate of the final product phytosterol maltitol suberate can reach 98.2%.

[0063] After stopping the he...

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Abstract

The invention discloses a one-pot method for preparing a hydrophilic phytosterol / stanol derivative, and belongs to the technical fields of food, cosmetics, medicine and chemical engineering. Phytosterol / stanol and diacid or diacid anhydride react for a period of time under the action of ionic liquid to generate the high-purity intermediate product phytosterol / stanol diacid monoester; a hydrophilic modifier is directly added to the reaction system for further reaction without separating the intermediate product, so that a high-purity hydrophilic phytosterol / stanol derivative is prepared. The hydrophilic phytosterol / stanol derivative with purity over 95% can be obtained through extraction separation. The two phases of esterification reaction are conducted in one pot, technological operation is simple, usage and separation of a solvent are reduced, the technological process is short, and energy consumption is reduced. The obtained hydrophilic phytosterol / stanol derivative is high in purity, high in yield and low in cost, and the method is good for industrial production.

Description

technical field [0001] The invention relates to a one-pot method for preparing hydrophilic phytosterol / stanol derivatives, and belongs to the technical fields of food, cosmetics, medicine, chemical industry and the like. Background technique [0002] Phytosterols are a class of steroidal compounds with cyclopentaneperhydrophenanthrene as the main skeleton, which widely exist in various plant tissues. Phytosterols mainly include β-sitosterol, stigmasterol, brassicasterol, and campesterol. At present, phytosterols are mainly obtained from the deodorized distillate produced in the vegetable oil refining process. The carbon-carbon double bonds in phytosterols are hydrogenated and saturated to form phytostanols, mainly including sitostanol and brassicostanol. [0003] Since the 1950s, researchers have conducted extensive research on the physiological activities and applications of phytosterols / stanols. Studies have confirmed that phytosterols / stanols have many functions such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P33/00
CPCC12P33/00Y02P20/54
Inventor 何文森崔丹丹王慧慧刘宇张艺露
Owner JIANGSU UNIV
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