Photochemical synthesis method of 25-hydroxy vitamin D3

A technology for hydroxyvitamin and photochemical synthesis, which is applied in the field of photochemical synthesis of 25-hydroxyvitamin D3, can solve the problems of difficult separation, low total yield, many by-products, etc., and achieves the improvement of reactant concentration, utilization efficiency, and simple production process. Effect

Active Publication Date: 2013-04-17
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

[0005] 25-Hydroxyvitamin D 3 The synthetic method usually has total synthesis method and semi-synthesis method, and the total synthesis method is not suitable for industrialized production because of long synthesis steps, low total yield and difficult separation.
Y.Mazur et al proposed a VD 3 A general method of hydroxylation modification at position 25 of the side chain to prepare 25-hydroxyvitamin D 3 and its analogues, but the method requires the VD 3 After breaking the skeleton, modify the side chain, the reaction steps are complicated, there are many by-products, and VD 3 25-Hydroxyvitamin D as raw material 3 High cost, not suitable for industrialization (J.Org.Chem.1979, 44, 3077-3080)
R.H.Hesse and L.Castedo et al. respectively with vitamin D 2 or analogues as raw materials to prepare 25-hydroxyvitamin D through a series of thermochemical reactions 3 , the total yield is all less than 10%, and the product is difficult to separate, and the raw material cost and preparation cost are all very high, so it is difficult to realize industrialization (J.Org.Chem.1986,51,4819-4828; J.Org.Chem.1986 , 51, 1272-1276)
Although vitamin D is produced photochemically 3 There are a large number of literature and related patent reports, but using this method to directly prepare active vitamin D 3 , especially 25-hydroxyvitamin D 3 but no report
At the same time, because many secondary reactions usually occur in photochemical reactions, the product selectivity is poor, and the product is difficult to control. The introduction of the hydroxyl group at the 25th position also has a great impact on the amphiphilicity of the raw material and product molecules, thus affecting its ability to react in different solvents. The solubility and the kinetics of its photochemical ring-opening reaction also increase the research difficulty of the synthetic method in some aspects

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  • Photochemical synthesis method of 25-hydroxy vitamin D3
  • Photochemical synthesis method of 25-hydroxy vitamin D3
  • Photochemical synthesis method of 25-hydroxy vitamin D3

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Experimental program
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Effect test

Embodiment 1

[0045] Photochemical synthesis of 25-hydroxyvitamin D 3 method, including the following steps:

[0046] 1) Light reaction of 25-hydroxy-7 dehydrocholesterol

[0047] In a 500 ml round bottom flask, dissolve 10 g of 25-hydroxy-7 dehydrocholesterol in 280 ml of ethanol / n-pentane (6:1, V / V) mixed solvent at room temperature, add 20 mg of 2,6 -Di-tert-butyl-p-methoxyphenol, mixed evenly, configured into a photochemical reaction solution; the reaction solution was placed in a built-in photochemical reactor with a 500W high-pressure mercury lamp and nitrogen gas; adjust the flow rate of nitrogen and Condensed water flow; start the mercury lamp, and time; the entire photochemical reaction device is placed in a light-proof fume hood, and a small fan is used to promote the dispersion of radiant heat to ensure that the temperature of the photochemical reaction liquid does not exceed 25 ° C to avoid premature generation 25-Hydroxyvitamin D 3 ; Monitor the reaction with high performanc...

Embodiment 2

[0053] Photochemical synthesis of 25-hydroxyvitamin D 3 method, including the following steps:

[0054] 1) Light reaction of 25-hydroxy-7 dehydrocholesterol

[0055] In a 500 ml round bottom flask, 10 g of 25-hydroxy-7 dehydrocholesterol was dissolved in 280 ml of isopropanol / n-octane (9:1, V / V) mixed solvent at room temperature, and 20 mg of 2 , 6-di-tert-butyl-p-methoxyphenol, mixed evenly, and configured as a photochemical reaction solution; put the reaction solution into a built-in photochemical reactor with a 500W high-pressure mercury lamp and nitrogen gas; adjust the nitrogen gas The flow rate and condensed water flow rate; start the mercury lamp, and time; the entire photochemical reaction device is placed in a light-proof fume hood, and a small fan is used to promote the dispersion of radiant heat to ensure that the temperature of the photochemical reaction solution does not exceed 25 ° C, avoid Premature production of 25-hydroxyvitamin D 3 ; Monitor the reaction w...

Embodiment 3

[0061] Photochemical synthesis of 25-hydroxyvitamin D 3 method, including the following steps:

[0062] 1) Light reaction of 25-hydroxy-7 dehydrocholesterol

[0063] In a 500 ml round bottom flask, 10 g of 25-hydroxyl-7 dehydrocholesterol was dissolved in 280 ml of methanol / n-hexane (4:1, V / V) mixed solvent at room temperature, and 20 mg of 2,6- Di-tert-butyl-p-methoxyphenol, mixed evenly, and configured as a photochemical reaction solution; the reaction solution was placed in a built-in photochemical reactor with a 500W high-pressure mercury lamp and nitrogen gas flow. Adjust the flow rate of nitrogen and condensed water; start the mercury lamp, and time; place the entire photochemical reaction device in a light-proof fume hood, and use a small fan to promote the dispersion of radiant heat to ensure that the temperature of the photochemical reaction solution does not exceed 25 ℃, to avoid premature formation of 25-hydroxyvitamin D 3 ; Monitor the reaction with high-perform...

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Abstract

The invention discloses a photochemical synthesis method of 25-hydroxy vitamin D3. The photochemical synthesis method comprises the following steps of: dissolving 25-hydroxy-7-dehydrocholesterol in a mixed solvent system containing a polar solvent and a non-polar solvent, and adding an antioxidant to react under the illumination; separating and recovering the 25-hydroxy-7-dehydrocholesterol after reacting; and heating to isomerize reactants retained after the 25-hydroxy-7-dehydrocholesterol is separated, and then freezing the isomerized reactants to recrystalize to obtain 25-hydroxy vitamin D3 crystals. The photochemical synthesis method disclosed by the invention has the main advantages that the conversion rate of 25-hydroxy-7-dehydrocholesterol open-loop under each time of illumination is below 40 percent through controlling the reactant concentration and the illumination time, and the 25-hydroxy vitamin D3 crystals with the purity of being more than 99 percent can be obtained without column chromatography isolation in the purifying process; and the photochemical synthesis method disclosed by the invention is simple in production process, improved in utilization efficiency of raw materials, saved in cost and suitable for large-scale production.

Description

technical field [0001] The invention relates to the synthesis of active vitamin D by organic photochemical method 3 technical field, specifically related to the photochemical synthesis of 25-hydroxyvitamin D 3 Methods. Background technique [0002] Vitamin D (hereinafter referred to as: VD) is a derivative of steroids, which exists in more than 10 forms in nature, among which vitamin D 3 (hereinafter referred to as: VD 3 ) has the most nutritional significance for humans and animals. VD 3 It is an essential fat-soluble vitamin for the growth, development, reproduction, maintenance of life and health of humans and animals. Its main physiological function is to promote the absorption of calcium and phosphorus in the intestine and bone calcification, increase the concentration of blood calcium and phosphorus, regulate Calcium and phosphorus metabolism and balance in the body. But studies have shown that vitamin D 3 It has no activity in the living body and cannot directl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C401/00
Inventor 李嫕陈金平曾毅李迎迎
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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