A method for enzymatically catalyzing the synthesis of ascorbate

A technology of ascorbic acid ester and ascorbic acid, which is applied in the field of enzyme-catalyzed synthesis of ascorbic acid ester, can solve the problems of low solubility of ascorbic acid, low solvent recovery rate, and poor stability, and achieve a simple and easy-to-control reaction process, not easy to degrade and oxidize, and produce products high quality effect

Inactive Publication Date: 2015-10-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, enzymes usually have low activity, slow reaction speed, and poor stability in these more polar solvents; on the other hand, tert-butanol and tert-amyl alcohol are derived from petrochemical resources and are not renewable
Although acetone is a food-safe and renewable solvent, the solubility of ascorbic acid in acetone is still low (only 16mmol / L at 50°C), and the boiling point of acetone is low (56°C), making it easy to Volatility not only leads to low solvent recovery rate, but also easily leads to serious air pollution problems in large-scale application

Method used

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  • A method for enzymatically catalyzing the synthesis of ascorbate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Ascorbic acid (100mg, 0.57mmol), vinyl palmitate (1.71mmol), 0.1g Molecular sieves and 10 mL of anhydrous 2-methyltetrahydrofuran-tert-butanol (4:1, v / v) were added into a stoppered Erlenmeyer flask, and then 16 mg of immobilized lipase derived from Candida antarctica B (purchased from Novozymes ), placed in a constant temperature oscillator at 50°C and 200 rpm under normal pressure, and monitored the reaction by TLC. After the reaction was completed, filter, concentrate the filtrate under vacuum, and separate by column chromatography to obtain 212 mg of ascorbic acid 6-palmitate, with a yield of 90%.

Embodiment 2

[0024] Ascorbic acid (100mg, 0.57mmol), methyl oleate (3.99mmol), 0.2g Molecular sieves, 10 mL of anhydrous 2-methyltetrahydrofuran-tert-butanol (4:1, v / v) were added to a stoppered Erlenmeyer flask, and then 100 mg of immobilized lipase from Thermomyces lanuginosus (purchased from Novozymes) was added , placed in a constant temperature oscillator at 50° C. and 200 rpm under normal pressure, and the reaction was monitored by TLC. After the reaction was completed, filter, concentrate the filtrate under vacuum, and separate by column chromatography to obtain 201 mg of ascorbic acid 6-oleate with a yield of 80%.

Embodiment 3

[0026] Ascorbic acid (100mg, 0.57mmol), vinyl undecylenate (1.71mmol), 0.3g Molecular sieves and 10 mL of anhydrous 2-methyltetrahydrofuran-tert-butanol (4:1, v / v) were added into a stoppered Erlenmeyer flask, and then 16 mg of immobilized lipase derived from Candida antarctica B (purchased from Novozymes ), placed in a constant temperature oscillator at 50°C and 200 rpm under normal pressure, and monitored the reaction by TLC. After the reaction was completed, filter, concentrate the filtrate under vacuum, and separate by column chromatography to obtain 179 mg of ascorbic acid 6-undecylenate with a yield of 92%.

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Abstract

The invention discloses a method for synthesis of ascorbic acid ester through enzyme catalysis. The method comprises the following specific steps: adding ascorbic acid, an acyl donor and molecular sieve into a mixed solvent containing 2-methyl tetrahydrofuran, mixing evenly, then adding lipase, carrying out an esterification or transesterification reaction with the reaction temperature of 40-60 DEG C and the oscillation speed of 150-300 rpm, and after the reaction, separating to obtain ascorbic acid ester. The method has the advantages of mild reaction conditions, high reaction region selectivity, easy separation of the products, fast reaction speed, good enzyme stability and the like, and is friendly to the environmental.

Description

technical field [0001] The invention belongs to the fields of biocatalysis and food biotechnology, and relates to an enzyme-catalyzed ascorbate synthesis method. Background technique [0002] Ascorbic acid is a natural antioxidant that is widely used in food, cosmetics and other fields. However, due to its strong hydrophilicity, the application of this compound in fat-soluble materials such as oil or fat-soluble cosmetics is greatly limited. Therefore, people use chemical modification to introduce long-chain fatty acids into ascorbic acid to enhance its fat solubility. Currently, ascorbyl palmitate and stearate have been approved by the European Union as food or cosmetic additives to improve the antioxidant properties of products. However, ascorbic acid esters are mainly synthesized industrially by acid- or base-catalyzed chemical methods. Due to the poor regioselectivity of chemical catalysts, many by-products and low yields, complex downstream separation and purificatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/04
Inventor 李宁宗敏华胡莹丹
Owner SOUTH CHINA UNIV OF TECH
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