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Method for preparing 7-hydroxydehydroabietic acid

The technology of dehydroabietic acid and hydroxyl group is applied in the field of preparation of pharmaceutical intermediate compounds, which can solve the problems of complex oxidation products, cumbersome reaction steps, low reaction selectivity, etc., and achieves good reproducibility, reduction of reaction steps and cost reduction. Effect

Inactive Publication Date: 2013-04-03
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the methods are oxidized from abietic acid to dehydroabietic acid and then oxidized to prepare 7-hydroxydehydroabietic acid, and the reaction steps are relatively cumbersome.
Han Chunrui et al. [Han Chunrui, Separation of Abietic Acid-Type Resin Acid and its Derivative Synthesis and Bioactivity Research, 2008] conducted in-depth research on the oxidation of abietic acid with hydrogen peroxide, chromium oxide and potassium permanganate, but the reaction selectivity is not high , the oxidation products are more complex

Method used

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  • Method for preparing 7-hydroxydehydroabietic acid
  • Method for preparing 7-hydroxydehydroabietic acid
  • Method for preparing 7-hydroxydehydroabietic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A kind of preparation method step of 7-hydroxydehydroabietic acid is:

[0027] Step 1: Add 2 parts by mass of rosin to 5 to 100 parts by mass of an organic solvent with 2 to 6 carbons, stir evenly, and heat to completely dissolve the rosin; the organic solvent with 2 to 6 carbons used is dichloromethane, 1, Any one or more of 4-dioxane, tetrahydrofuran or acetone.

[0028] Step 2: Add the rosin solution dissolved in the previous step into a fixed-bed reactor equipped with an oxidant. The fixed-bed reactor is kept at a temperature of 30-70°C, and the reaction time is ≤60 min. A solution of 7-hydroxydehydroabietic acid is obtained; the oxidizing agent is any one of dichlorodicyanoquinone, selenium dioxide and manganese dioxide.

[0029] Step 3: Filter the 7-hydroxydehydroabietic acid solution in the previous step, distill, recrystallize, and dry in vacuum to obtain pure 7-hydroxydehydroabietic acid. For recrystallization, any one of acetone, ethanol, and acetic acid is ...

Embodiment 2

[0031] Put 2 parts of rosin into 10 parts of dichloromethane solvent, heat to 50°C, and dissolve them all under stirring. The dissolved abietic acid is added to the fixed-bed reactor equipped with dichlorodicyanoquinone. The reaction was heated for 5 min to obtain a 7-hydroxydehydroabietic acid solution; the content of 7-hydroxydehydroabietic acid in the solution was analyzed by gas chromatography, and its content was 76%. The reaction solution was filtered, distilled, and recrystallized from acetone to obtain the target product, and the content of 7-hydroxydehydroabietic acid was more than 95% according to liquid chromatography (HPLC).

Embodiment 3

[0033] Put 2 parts of rosin into 10 parts of 1,4-dioxane solvent, heat to 50°C, and dissolve them all under stirring. Add the dissolved rosin to the MnO 2 in a fixed bed reactor. The reaction was heated for 20 min to obtain a 7-hydroxydehydroabietic acid solution; the content of 7-hydroxydehydroabietic acid in the solution was analyzed by gas chromatography, and its content was 78%. The reaction solution was filtered, distilled, and recrystallized from acetic acid to obtain the target product, and the content of 7-hydroxydehydroabietic acid was more than 96% according to liquid chromatography (HPLC).

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Abstract

The invention discloses a method for preparing 7-hydroxydehydroabietic acid, which comprises the following steps of: 1, adding 2 mass parts of rosin into 5 to 100 mass parts of organic carbon having 2 to 6 carbon atoms, stirring the mixture uniformly, and heating the mixture to fully dissolve the rosin; 2, adding the dissolved rosin solution into a fixed bed reactor filled with oxidant, keeping the temperature of the fixed bed reactor at 30 to 70 DEG C, and obtaining 7-hydroxydehydroabietic acid solution; and 3, filtering the 7-hydroxydehydroabietic acid solution, and performing distillation,re-crystallization and vacuum drying to obtain a pure 7-hydroxydehydroabietic acid product. The rosin is directly used as a raw material, so the steps are simplified, and the cost is saved; and the low-cost oxidant is used, the reaction is quick, and the yield of the 7-hydroxydehydroabietic acid reaches over 75 percent.

Description

technical field [0001] The invention belongs to the preparation of pharmaceutical intermediate compounds, in particular to a method for separating and preparing 7-hydroxydehydroabietic acid, a derivative of abietic acid, from rosin through oxidation reaction. Background technique [0002] Natural rosin contains dehydroabietic acid, but its content is relatively small. At present, it is mainly obtained through disproportionation reaction using palladium carbon catalyst under the high temperature condition of 270 ℃, and then separated and prepared by amine salt method. Dehydroabietic acid derivatives have various biological activities such as antibacterial, antiviral, antitumor, and antiulcer [Han Chunrui et al., Progress in Chemical Industry, 2007, 26, 490; Ulusu N N et al, Phytother. Res. 2002, 16, 88; Roberto A Set al, Molecular and Cellular Endocrinology. 2003, 212, 41], and it also has a wide range of applications in the fields of cosmetics and biopesticides. Due to the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C62/32C07C51/367C07C51/347
Inventor 周永红杨晓慧刘红军
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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