Preparation method of 6,8,11,13-tetra-abietic olefine acid

A technology of abietic acid and rosin, which is applied in the preparation of carboxylates, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of no discovery, extraction, preparation, and difficulty in activity research, and achieve rapid reaction, avoidance of The effect of organic solvent purification and fewer by-products

Inactive Publication Date: 2013-09-25
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, this has caused serious difficulties for the extraction, preparation and activity research of 6,8,11,13-abietonic acid
So far, except for some articles related to the existence of 6,8,11,13-arbitronic acid in natural pine resin, no commercially available 6,8,11,13-arietonic acid products have been found

Method used

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  • Preparation method of 6,8,11,13-tetra-abietic olefine acid
  • Preparation method of 6,8,11,13-tetra-abietic olefine acid
  • Preparation method of 6,8,11,13-tetra-abietic olefine acid

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Experimental program
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Embodiment 1

[0027] A kind of preparation method step of 6,8,11,13-abietonic acid is:

[0028] Step 1: Add 10 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.

[0029] Step 2: Add the rosin solution dissolved in the previous step into a fixed-bed reactor equipped with an oxidizing agent and a dehydrating agent. The fixed-bed reactor maintains a temperature of 30-70°C and a reaction time of ≤120min. Obtain 6,8,11,13-abietonic acid solution; the oxidizing agent is any one of dichlorodicyanoquinone, selenium dioxide, and manganese dioxide; the dehydrating agent is 4A molecular sieve, 5A Molecular sieve, any one of p-toluenesulfonic acid.

[0030] Step 3: filter the 6,8,11,13-arbitronic acid solution in the above step, distill, recrystallize, and then vacuum dry to obtai...

Embodiment 2

[0032] Put 10 parts of rosin into 20 parts of dichloromethane solvent, heat to 50° C., and dissolve them all under stirring. Add the dissolved rosin solution into the fixed-bed reactor equipped with dichlorodicyanoquinone and 4A molecular sieve. The reaction was heated for 10 minutes to obtain a 6,8,11,13-arbitronic acid solution; the content of 6,8,11,13-arbitronic acid in the solution was analyzed by gas chromatography, and its content was 78%. The reaction solution was filtered, distilled, and recrystallized from acetone to obtain the target product, and the content of 6,8,11,13-abietonic acid was more than 95% according to liquid chromatography (HPLC).

Embodiment 3

[0034] Put 10 parts of rosin into 20 parts of 1,4-dioxane solvent, heat to 50° C., and dissolve it completely under stirring. Add the dissolved rosin to the MnO 2 and 4A molecular sieve in a fixed bed reactor. The reaction was heated for 20 minutes to obtain a 6,8,11,13-arbitronic acid solution; the content of 6,8,11,13-arbitronic acid in the solution was analyzed by gas chromatography, and its content was 80%. The reaction solution was filtered, distilled, and recrystallized from acetic acid to obtain the target product, and the content of 6,8,11,13-arbitronic acid was more than 97% according to liquid chromatography (HPLC).

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Abstract

The invention discloses a preparation method of 6,8,11,13-tetra-abietic olefine acid. The method comprises the following steps: step 1: adding rosin to an organic solvent containing 2-6 carbon, and heating for dissolving; step 2: adding the dissolved rosin solution obtained in step 1 to a fixed bed reactor filled with an oxidizer at the temperature of 30-70 DEG C, thus obtaining 6,8,11,13-tetra-abietic olefine acid solution; and step 3: filtering, distilling, recrystallizing and vacuum-drying the 6,8,11,13-tetra-abietic olefine acid solution obtained in step 2 to finally obtain the pure product of the 6,8,11,13-tetra-abietic olefine acid. In the method, the rosin is directly taken as a raw material to obtain abietic acid, namely the 6,8,11,13-tetra-abietic olefine acid through purification, and the content of the 6,8,11,13-tetra-abietic olefine acid reaches over 95% through high performance liquid chromatography (HPLC) analysis. The preparation method has the advantages of mild reaction conditions, rapid and short-time reaction, good repeatability and high 6,8,11,13-tetra-abietic olefine acid yield up to over 80%, thus being very beneficial to industrial production.

Description

technical field [0001] The invention belongs to the preparation of pharmaceutical intermediate chemicals, in particular to a method for separating and preparing abietic acid derivative 6,8,11,13-tetraenoabietic acid from rosin through oxidation reaction. Background technique [0002] Resin acid is the main component of rosin, and it is a mixture of a series of tricyclic diterpene monocarboxylic acids with hydrophenanthrene structure, with multiple chiral centers [He Jinke, Li Qiji. Complete Book of Forest Products Chemical Industry. Beijing: China Forestry Press, 1997 , 1096, 1102-1103], have a wide range of biological activities, and resin acids and their derivatives have important uses in the fields of anti-inflammation, anti-tumor, lowering blood cholesterol, and inhibiting bacterial growth [Rao Xiaoping, Song Zhanqian, Gao Hong. Chemistry Bulletin, 2006, 2, 168-172]. Moreover, the tricyclic skeleton and carboxyl group of rosin resin acid can undergo a series of chemical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C61/39C07C51/377C07C51/487
Inventor 周永红杨晓慧刘红军刘承果
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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