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Preparation method for high-purity tocopherol succinate salt

A technology of tocopheryl succinate and tocopherol, which is applied in the direction of organic chemistry, can solve the problems of difficult purification of impurities and low purity, and achieve the effects of reducing content, improving purity, and easy purification

Inactive Publication Date: 2018-08-17
SHANGHAI BETTERSYN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the research found that the purity of the products on the market is not high, and several major impurities are very difficult to purify out
All the methods disclosed in CN1182132 and CN1199966 cannot obtain the product with a purity higher than 99.9%.

Method used

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  • Preparation method for high-purity tocopherol succinate salt
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  • Preparation method for high-purity tocopherol succinate salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of isophytol:

[0052] Dissolve 15g of farnesyl acetone in 90mL of isopropanol, add 3g of palladium carbon, hydrogen pressure 70kg / cm 3 , 100°C for 3 hours to obtain an intermediate (hexahydrofarnesylacetone).

[0053] In a 500mL round-bottomed three-neck flask with a thermometer inserted, add 230mL (0.23mol, 1.0mol / L) of newly prepared vinyl chloride magnesium Grignard reagent under nitrogen protection, and cool the reaction solution to about 0°C in an ice bath. Stir, slowly add hexahydrofarnesylacetone (40.2g, 0.15mol) dropwise, control the temperature of the reaction solution below 5°C, complete the dropwise addition in 2 hours, continue the reaction for 2 hours, and check that the reaction is complete by gas phase detection, keep adding 40mL in an ice bath Concentrated hydrochloric acid quenched the reaction, adjusted the pH value of the reaction solution to 6-7 with saturated aqueous ammonium chloride solution, precipitated a large amount of solid, fil...

Embodiment 2

[0055] Preparation of dl-alpha-tocopherol:

[0056] In a 2L reaction flask, add 325 mL of butyl acetate, 1 mol of trimethylhydroquinone, 0.2 mol of anhydrous zinc chloride and raise the temperature to 110°C to dissolve completely, then add 0.97 mol of isophytol in batches (prepared in Example 1) , divide water at 110°C, and raise the temperature to 129°C to complete the reaction. Drop to 30°C and add 200mL of water, extract and remove zinc chloride, add 200mL of 0.1% hydrochloric acid to the butyl acetate phase for extraction and washing, concentrate and remove the solvent to obtain dl-α-tocopherol, GC99.4%; refractive index n20 / D: 1.506 ; Specific optical rotation (20°C) -0.03°.

Embodiment 3

[0058] Preparation of tocopheryl succinate and calcium salt thereof:

[0059] Take dl-α-tocopherol (10g, 23.22mmol, prepared in Example 2), dissolve it in 100ml of anhydrous methanol, add palladium carbon (0.2g, palladium content 5wt%), and react under 0.3MPa hydrogen pressure for 10h. Filter with celite, wash with 10ml of methanol, and concentrate to obtain 10g of the product. The hydrogenated tocopherol (10g, 23.22mmol) was dissolved in toluene (50mL), and succinic anhydride (4.2g, 41.80mmol) and triethylamine (0.82g, 8.13mmol) were added to react at 60°C for 6h. At room temperature, filter, add 100mL hydrochloric acid (1M), 25mL hydrochloric acid (1M) successively to extract, 25mL water to extract and wash, the organic phase is dried (Na2SO4) and concentrated to give crude product 12.2g, purity 98.2478%, product map as follows figure 1 shown. Dissolve calcium acetate (15.56 g, 0.098 mol) in 106 ml of water, and then add 185 ml of anhydrous methanol to the system to prepar...

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Abstract

The invention relates to the field of organic synthesis, specifically to a preparation method for tocopherol succinate salt. The preparation method for the tocopherol succinate salt provided by the invention comprises the following steps: hydrogenating dl-alpha-tocopherol in the presence of a precious metal catalyst, subjecting a hydrogenated product and succinic anhydride to an esterification reaction in the presence of alkali so as to prepare a tocopherol succinate intermediate; and subjecting the tocopherol succinate intermediate to salt-forming. The preparation method for the tocopherol succinate salt provided by the invention can effectively improve the purity of a target product, can effectively reduce the content of a single impurity, and can prepare a calcium salt product with a purity capable of reaching 99.9% or above.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of tocopherol succinate. Background technique [0002] Tocopherol succinate calcium salt is widely used at present, and has the following outstanding effects: 1. Promote the absorption of VA and fat, improve the nutrient supply of the body, and enhance the absorption and utilization of nutrients by muscle cells and other biological characteristics. 2. It can effectively delay aging. At the same time, due to its promoting effect on nucleic acid metabolism, it can effectively eliminate oxygen free radicals in the body, maintain the vigorous function of various organs, and play the role of delaying aging and prolonging life. 3. It can prevent and treat muscle atrophy, cardiovascular disease, infertility and miscarriage caused by VE deficiency. 4. Natural VE has a very good effect on menopausal disorders, autonomic disorders and high cholesterol, and can prevent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/72
CPCC07D311/72
Inventor 何其中罗光顺黄浩
Owner SHANGHAI BETTERSYN BIOTECH
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