Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material

A vitamin and stigmasterol technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of high cost, environmental protection, and low cholesterol yield, and achieve the effect of mild reaction conditions, strong operability, and easy operation

Active Publication Date: 2021-05-04
AKTIN CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006]Cholesterol is the most critical raw material for the production of vitamin D3, but there are few sources of cholesterol. The production rate is too low, and the fermentation conditions are too difficult to control, and industrial...

Method used

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  • Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material
  • Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1 stigmasterol acetate (IX)

[0036] 10Kg stigmasterol was added to a 1000L enamel reaction kettle, 200g pyridine and 3.2Kg powdered potassium carbonate were added. Close the enamel kettle, vacuum inhale 200L n-hexane. The stirring was started, and the jacket was heated to an internal temperature of 60°C. 2.96Kg of acetic anhydride was added dropwise while maintaining the temperature. After the dropwise addition was completed, the temperature was maintained to continue the reaction for 3 hours. After the reaction was judged to be complete by thin layer chromatography. Filter while hot with a stainless steel plate frame, rinse the filter cake with 40 L of fresh n-hexane, and concentrate the combined n-hexane solution to dryness in vacuo to obtain a white solid. The white solid was added with 100L of ethanol, refluxed at 80°C, dissolved and cleared, cooled to crystallize, and 10.8Kg of compound IX was precipitated as a white needle produc...

Embodiment 2

[0037] The preparation of embodiment 2 side chain oxide compound (VIII)

[0038] Add 10Kg of compound IX to 500L of ethanol, use a cold tank machine to cool down to -50°C, and pass through oxygen (containing 1% ozone, which is freshly produced by an ozone machine) under stirring conditions for oxidation; TLC tracking until the oxidation is complete; oxidation After completion, replace oxygen with nitrogen; let the system slowly heat up to 0°C;

[0039] Add 2000g of thiourea to 20L of 90% ethanol water, dissolve and clear, then slowly add to the oxidation reaction system; slowly rise to room temperature and stir for 16 hours; after the reaction is complete, filter to remove the precipitate; wash the precipitate with 2000ml of 90% ethanol water ; The combined filtrates were concentrated at 60°C until the volume reached 50 L, and cooled to crystallize; 6.4Kg of white solid compound VIII was obtained by filtration, with a yield of 78%.

[0040] If an additional 5 Kg of silica gel...

Embodiment 3

[0041] Preparation of Embodiment 3 Side Chain Isopentyl Reductant (VII)

[0042] Add 5.85Kg of triphenylphosphine to 120L of toluene and dissolve it clearly; dissolve 3.39Kg of 1-bromoisopentane in 4.5L of toluene; Add to the triphenylphosphine solution; heat up and stir until reflux reaction; after the reaction is complete, cool down to room temperature; add 2.85Kg sodium tert-butoxide, and continue to stir;

[0043] Dissolve 5.58Kg of compound VIII in 6L of toluene and add it dropwise into the above reaction system; reflux the reaction again, monitor by TLC until the reaction of the raw materials is completed; cool in an ice-water bath, add 10% phosphoric acid water dropwise after cooling, and adjust the pH value to neutral Properties; liquid separation, the toluene layer was concentrated to dryness, refluxed with 75L of methanol to dissolve, left to cool and crystallized naturally to obtain 5.61Kg of compound VII, with a yield of 88%.

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Abstract

The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing vitamin D by using stigmasterol as raw material 3 The new method for industrialization belongs to the field of chemical drug preparation. Background technique [0002] Vitamin D 3 (vitamin D 3 ), also known as cholecalciferol, is a drug with antirickets activity, which is widely considered as an important substance regulating calcium and phosphorus metabolism. Vitamin D deficiency in the body 3 When overweight, it will lead to insufficient absorption of calcium and phosphorus, affect the normal development of bones, make the bones soft, and eventually lead to the formation of rickets. It can be seen that an appropriate amount of vitamin D 3 Supplementation is essential to human health. [0003] Vitamin D 3 It is not active by itself, it needs to be metabolized by the human body into its active form to function. active vitamin D 3 There are mainly three types of derivatives: 1α-hydroxyvitamin D 3 ...

Claims

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Application Information

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IPC IPC(8): C07C401/00C07J9/00
CPCC07C401/00C07J9/00
Inventor 付书清张林徐敏曹怀塘
Owner AKTIN CHEM INC
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