L-ascorbic acid octoate and preparation method thereof

A technology of octanoic acid ester and ascorbic acid, which is applied in the field of L-ascorbyl octanoate and its preparation, can solve the problems of low oil solubility and easy crystallization of L-ascorbic acid long-chain fatty acid ester, and achieve high product purity and recovery rate, The effect of easy product and stability improvement

Inactive Publication Date: 2015-08-12
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at providing L-ascorbic acid octanoate and its preparation method in view of the problems of low oil solubility of L-ascorbic acid long-chain fatty acid esters and easy crystallization at low temperature

Method used

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  • L-ascorbic acid octoate and preparation method thereof
  • L-ascorbic acid octoate and preparation method thereof
  • L-ascorbic acid octoate and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] The specific operation steps of preparing L-ascorbyl octanoate are as follows:

[0032] (1) Enzymatic synthesis of L-ascorbyl octanoate

[0033] Take a clean 150mL Erlenmeyer flask with a stopper, put 0.704g L-ascorbic acid, 3.456g n-octanoic acid and 0.141g Novozym 435 immobilized lipase in the bottle, add 20mL tert-butanol and 1.2g 4? Molecular sieve , Tighten the stopper, wrap the mouth of the bottle with plastic wrap, supplemented by a rubber band to ensure that the system is sealed. The Erlenmeyer flask was placed in a constant temperature water bath shaking shaker at 55°C and 150r / min for 10 hours to obtain a reaction solution containing L-ascorbyl caprylate, and the conversion rate of L-ascorbic acid esterification reached 87.5%.

[0034] (2) Separation and purification of L-ascorbyl octanoate in the reaction liquid

[0035] After the reaction was completed, the reaction solution was suction filtered to remove 4? molecular sieves, lipase and unreacted L-ascorbi...

Embodiment 2

[0041] The operation steps are the same as in Example 1, except that the reaction mixture is separated by silica gel column chromatography after being washed with water. Soak 24g of silica gel with a specification of 200~300 mesh in the eluent, the eluent is a mixed solvent of ethyl acetate:petroleum ether with a volume ratio of 1:1, swell for 30min, wet-pack the column (16×500mm), and wash with Load the sample after 30 minutes of equilibration with the solvent removal. The sample loaded is a reaction mixture containing L-ascorbyl octanoate. The sample volume is 2.1g, and the sample concentration is 0.5g / mL (diluted with eluent). Elution, the flow rate is 1mL / min, the collection starts after about 1 column volume, and stops after 2 column volumes, and the collected solution is vacuum rotary evaporated to obtain L-ascorbyl caprylate, repeat twice. 0.827g of L-ascorbyl octanoate with a purity of 97.5% was obtained, and the product recovery rate was 76.3%.

[0042] Table 2 The s...

Embodiment 3

[0046] The specific operation steps of preparing L-ascorbyl octanoate are as follows:

[0047] (1) Enzymatic synthesis of L-ascorbyl octanoate

[0048] Take a clean 250mL round bottom flask, add 4.225g L-ascorbic acid, 20.735g n-octanoic acid and 0.81g Novozym 435 immobilized lipase from Novozymes, add 100mL tert-amyl alcohol and 6g 4? Seal the mouth of the bottle. The round bottom flask was placed on a constant temperature water bath evaporator at 55.3°C and 150r / min to react for 11.5h to obtain a reaction solution containing L-ascorbyl caprylate, and the conversion rate of L-ascorbic acid esterification reached 90.3%.

[0049] (2) Separation and purification of L-ascorbyl octanoate in the reaction solution

[0050] After the reaction was completed, the reaction solution was suction filtered to remove 4? molecular sieves, lipase and unreacted L-ascorbic acid, and the obtained filtrate was subjected to vacuum rotary evaporation to remove the solvent, dissolved in 100 mL of e...

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Abstract

The invention relates to a L-ascorbic acid octoate and a preparation method thereof. According to the invention, L-ascorbic acid octoate is dissolved in water, and has oil solubility, anti-oxidizability, emulsibility and bacteriostatic activity. The preparation method is characterized in that n-caprylic acid and L-ascorbic acid octoate are taken as raw materials, immobilized lipase in an organic phase system is used for a catalyzed esterification to synthesize L-ascorbic acid octoate, after the reaction is complete, a reaction solution is performed with steps of filtering, extracting, crystallizing or silica gel column chromatography, and drying under vacuum to obtain L-ascorbic acid octoate. The preparation method takes medium-chain fatty acid n-caprylic acid as a acyl donor, conversion rate being 80-90% can be obtained in a short reaction time, separating purifying is relatively simple, products purity is 95-98%, recovery rate is 75-85%, lipase reuse enables large frequency, enzyme activity can be kept by original 60-75% after 50-80 times of usage, production cost is reduced, and industrial production can be realized.

Description

technical field [0001] The invention belongs to the technical field of biocatalysis, separation and purification of multifunctional natural antioxidants, and specifically relates to L-ascorbyl octanoate and a preparation method thereof. Background technique [0002] With the rapid development of the food industry and the continuous improvement of people's living standards, the safety of food and food additives has been paid more and more attention. Fat is one of the seven major nutrients for human beings. It is an important source of heat energy for the human body. It provides essential fatty acids and fat-soluble components for the human body. It has important physiological functions, and can also improve the taste of food, provide food flavor and production functions. As one of the important raw materials of food industry, oil and fat directly affect the quality of food. However, unsaturated fatty acids in oils are easily affected by factors such as air, light, and moistu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/62C12P17/04
CPCC07D307/62C12P17/04
Inventor 潘丽军张淑青姜绍通操丽丽莫玉稳
Owner HEFEI UNIV OF TECH
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