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Preparation method of D-pantoic acid lactone

A technology of pantolactone and pantoate, which is applied in the field of biochemical industry, and can solve the problems of product chiral separation, cyclization, crystallization and refining process without specific elaboration, product purity that is difficult to meet the requirements, and hydrolysis that is difficult to complete, etc. problem, to avoid the increase of impurities, low cost, and reduce the effect of reaction steps

Pending Publication Date: 2021-04-20
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional method is to use the method of chemical resolution to resolve the racemized pantoacidolactone. The resolution is expensive, the process is complicated, the resolution is difficult, and the separation is difficult.
It is also reported that L-pantolactone hydrolase is used to hydrolyze L ester and remove L ester, but the hydrolysis is difficult to complete, and the product purity is difficult to meet the requirements
At the same time, there are also documents about the hydrolysis of D ester by D-pantolactone hydrolase, but there is no specific elaboration on the chiral separation, cyclization, crystallization and refining process of the hydrolyzed product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] This example provides a preparation method of D-pantolactone.

[0039] (1) Add 150g of DL-pantolactone in a 500mL three-necked bottle, add 150g of water to dissolve, add 150mL of immobilized D-pantolactone hydrolase, control the temperature at 25°C, and drop ammonia water to control the pH at 6.5- 7.5 range until the reaction stops, then extract and separate with ethyl acetate 300g 4 times, collect the water phase, take a sample after each extraction, and see Table 1 for the lactone peak area in the water phase detected by HPLC;

[0040] Table 1

[0041] sample Relative residual amount of lactone / % Before extraction 100 after one extraction 26.73 after secondary extraction 7.46 after three extractions 0.18 After four extractions not detected

[0042] (2) Adjust the pH value of the obtained D-pantoate aqueous solution to 1.0 with sulfuric acid, heat up to 75°C, carry out the cyclization reaction for 2 hours, adjust the pH to...

Embodiment 2

[0045] This example provides a preparation method of D-pantolactone.

[0046] (1) Add 200g of DL-pantolactone in a 500mL three-necked bottle, add 190g of water to dissolve, add 250mL of immobilized D-pantolactone hydrolase, control the temperature at 20°C, and drop ammonia water to control the pH at 6.5- 7.5 until the reaction stops, then extract and separate with ethyl acetate 450g for 3 times, and collect the aqueous phase;

[0047] (2) Adjust the pH value of the obtained D-pantoate aqueous solution to 3.0 with sulfuric acid, heat up to 60°C, carry out the cyclization reaction for 3 hours, adjust the pH to 4.5-5.0 after cooling down, and then extract with 400 g of ethyl acetate for 3 Second, concentrated and removed the solvent to obtain D-pantolactone solid, added a small amount of anhydrous methanol to stir and dissolve, and cooled down to crystallize to obtain 69.5g of D-pantolactone crude product, with a specific rotation of 45.30°;

[0048] (3) The obtained crude cryst...

Embodiment 3

[0050] This example provides a preparation method of D-pantolactone.

[0051] (1) Add 100g of DL-pantolactone into a 500mL three-necked bottle, add 100g of water to dissolve, add 150mL of immobilized D-pantolactone hydrolase, control the temperature at 30°C, add ammonia water dropwise to control the pH at 6.5- 7.5 until the reaction stops, then extract and separate with ethyl acetate 300g for 3 times, and collect the aqueous phase;

[0052] (2) Adjust the pH value of the obtained D-pantoate aqueous solution to 3.0 with sulfuric acid, heat up to 90°C, carry out the cyclization reaction for 2 hours, adjust the pH to 4.5-5.0 after cooling down, and then extract with 200 g of ethyl acetate for 3 Second, concentrate and remove solvent to obtain D-pantolactone solid, add a small amount of anhydrous methanol to stir and dissolve, then cool down and crystallize to obtain D-pantolactone crude product 36.7g, specific rotation 45.72 °;

[0053] (3) The obtained crude crystals were dissolv...

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Abstract

The invention provides a preparation method of D-pantoic acid lactone, which comprises the following steps: (1) carrying out ring-opening reaction on DL-pantoic acid lactone under the action of D-pantoic acid lactone hydrolase, reacting with ammonia water to form salt, and then carrying out post-treatment to obtain D-pantoic acid salt; and (2) carrying out cyclization on the D-pantoic acid salt under an acidic condition to obtain a reaction solution containing the D-pantoic acid lactone. The preparation method provided by the invention is simple and convenient, the solvent can be recycled, the cost is low, the product purity is higher, and the yield is higher.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and relates to a preparation method of D-pantoolactone, in particular to a method for preparing D-pantoolactone by using DL-pantoolactone as a raw material. Background technique [0002] D-pantothenic acid lactone is the precursor of D-calcium pantothenate, D-calcium pantothenate is a vitamin B drug, which is a component of coenzyme A, participates in the metabolism of protein, fat and sugar in the body, and can also be used for vitamin B Deficiency and peripheral neuritis, as well as intestinal colic after surgery; it can be used in combination with vitamin C to treat disseminated lupus erythematosus; it is also widely used in the food industry and livestock and poultry farming. [0003] At present, the main technology for producing D-pantolactone lies in the chiral resolution of the racemate. The traditional method is to use the method of chemical resolution to resolve the racemized panto...

Claims

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Application Information

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IPC IPC(8): C07D307/33C12P7/42C12P41/00
Inventor 林文龙徐新丁亚梅陈昀李立标郑爱王清清
Owner BENGBU BBCA MEDICINE SCI DEV