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One-pot method for preparing hydrophilic phytosterol/stanol derivatives

A technology for phytostanols and phytosterols is applied in the field of preparing hydrophilic phytosterol/stanol derivatives, which can solve the problems of long reaction time and low product conversion rate, and achieves low cost, high product purity and high yield. high rate effect

Active Publication Date: 2019-09-17
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 derivatives
  • One-pot method for preparing hydrophilic phytosterol/stanol derivatives
  • One-pot method for preparing hydrophilic phytosterol/stanol derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Phytosterol polyethylene glycol succinate diester

[0039] 1. Preparation of phytosterol succinic acid monoester

[0040] Preparation method: 12.4g of phytosterol, 3.0g of succinic anhydride, and 0.25g of ionic liquid 1-butylsulfonic acid-3-methylimidazole hydrogen sulfate were respectively added to a reflux reaction device equipped with stirring and oil bath temperature control. , add 100 mL of petroleum ether, turn on stirring to adjust the temperature to 100-110 °C, and react for 1-1.5 h. The conversion rate of phytosterol succinic acid monoester detected by HPLC can reach 98.7%. 10 mL of distilled water was added to the reaction solution, extracted, the organic phase layer was collected, and the solvent was removed by rotary evaporation to obtain 14.9 g of phytosterol succinic acid monoester.

[0041] Structural identification: Phytosterol succinate monoester FT-IR: 2370-3700cm -1 The broad peak between is the stretching vibration absorption of hydroxyl...

Embodiment 2

[0056] Example 2 Phytostanol tea polyphenol adipate diester

[0057] 12.5g of phytostanol, 21.9g of adipic acid, 1.0g of ionic liquid 1-propylsulfonic acid-3-methylimidazole p-toluenesulfonate were respectively added to the reflux reaction equipped with stirring and oil bath temperature control. device, add 200 mL of tert-butanol, turn on stirring to adjust the temperature to 80°C to 85°C, and react for 2.5h to 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, supplement 0g of ionic liquid 1-propylsulfonic acid-3-methylimidazole p-toluenesulfonate, adjust the temperature to 80℃~85℃, 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] Af...

Embodiment 3

[0060] Example 3 Phytosterol maltitol suberic acid diester

[0061] 12.4g of phytosterol, 7.8g of suberic acid, and 0.36g of ionic liquid 1-butylsulfonic acid-3-methylimidazole trifluoromethanesulfonate were respectively added to the reflux reaction device equipped with stirring and oil bath temperature control. , add 100 mL of tert-amyl alcohol, turn on stirring to adjust the temperature to 100 ℃ ~ 105 ℃, and react for 1 h to 1.5 h. Heating was stopped and 100 μL was sampled for HPLC analysis. The conversion rate of the intermediate product phytosterol suberic acid monoester can reach 97.1%.

[0062] After sampling, add 20.6g of hydrophilic modifier maltitol, and supplement 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 suberic acid die...

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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, belonging to the technical fields of food, cosmetics, medicine and chemical industry. Background technique [0002] Phytosterols are a class of steroid compounds with cyclopentane perhydrophenanthrene as the main skeleton, which are widely present in various plant tissues. Phytosterols mainly include β-sitosterol, stigmasterol, rapeseed sterol, and campesterol. Currently, phytosterols are mainly obtained from the deodorized distillate produced in the refining process of vegetable oil. The carbon-carbon double bonds in phytosterols are hydrogenated and saturated, which are phytostanols, mainly including sitostanol and rapeseed stanol. [0003] Since the 1950s, researchers have carried out extensive research on the physiological activities and applications of phytosterols / stanols. Studies have confirmed that phytosterols / stanols have many effects such as...

Claims

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Application Information

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Patent Type & Authority Patents(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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