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Method for synthesizing glabridin

A synthetic method, the technology of glabridin, is applied in the direction of organic chemistry, which can solve the problems that are not suitable for large-scale production, and achieve the effects of high yield, short route, and simple operation and separation

Active Publication Date: 2013-04-10
山东济清科技服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Glabridin was prepared by this route through ten steps of reaction, with a yield of 6.2%, in which the condensation reaction of compounds 1 and 2 in the key step needs to be carried out at -78°C, which is not suitable for large-scale production

Method used

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  • Method for synthesizing glabridin

Examples

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Embodiment 1

[0033] (1) Synthesis of 2,4-dimethoxyphenylacetic acid (compound 2)

[0034] Put the compound 2,4-dimethoxyacetophenone (0.1mol), sulfur powder (0.2mol), and morpholine (0.2mol) in a reaction flask, stir and heat to reflux for 7h, cool to room temperature, add 200mL dichloromethane Dissolve, wash with 6N hydrochloric acid (100mL×2), collect the organic phase and distill off the solvent under reduced pressure to obtain a brown oil. Add 20wt% sodium hydroxide solution, stir and reflux for 7 hours, cool to room temperature, adjust the pH to 1-2 with concentrated hydrochloric acid, collect the obtained solid by filtration, and obtain compound 2 with a yield of 85%.

[0035] (2) Synthesis of 7-hydroxy-2′,4′-dimethoxyisoflavone (compound 3)

[0036] Compound 2 (0.1mol) was mixed with resorcinol (0.1mol), and reacted at 85°C for 3h under the catalysis of fresh boron trifluoride diethyl ether (60mL) to generate a coupling product. After cooling to room temperature, add dry N,N-dimet...

Embodiment 2

[0046] The synthesis of compounds 2, 3, 4, 6 and glabridin is the same as that in Example 1, except that the preparation of compound 5 is different.

[0047] Preparation of Compound 5: Compound 4 (0.02mol) and 3-methyl-2-enbutanal (0.024mol) were mixed in anhydrous picoline (80mL), refluxed for 10h, cooled to room temperature, washed with 6N hydrochloric acid , extracted with ethyl acetate, dried over anhydrous sodium sulfate, and removed the solvent with steam to obtain a brown oil, which was dissolved in n-hexane and then frozen and crystallized for 12 hours to obtain a light yellow solid, namely compound 5, with a yield of 77%.

Embodiment 3

[0049] The synthesis of compounds 2, 3, 4, 6 and glabridin is the same as that in Example 1, except that the preparation of compound 5 is different.

[0050] Preparation of compound 5: under nitrogen protection, compound 4 (0.01mol), 3-methyl-2-enbutyraldehyde (0.012mol), phenylboronic acid (0.012mol), and 50mL of acetic acid were mixed in 250mL of toluene, and refluxed for 7h , The solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain compound 5 with a yield of 71%.

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Abstract

The invention relates to a method for synthesizing glabridin. The method comprises the following steps: using acetophenone protected by phenol hydroxy as a raw material, carrying out a Willgerodt-Kindler reaction to obtain aryl phenylacetic acid, and carrying out a Friedel-Crafts reaction to obtain an isoflavones compound; causing the isoflavones compound to carry out Pd / C catalytic hydrogenation to obtain a isoflavanone compound; and causing the isoflavanone compound to carrying out a crclizationreaction, a conyl reduction reaction and a removing phenolic hydroxyl group protection group reaction to obtain the glabridin. The operation and the serparation of the steps of the method are simple, the yield is higher, the used reagents are common reagents, are cheap and are easily obtained, the path is shorter, and the tptal yield is not lower than 20 percent.

Description

technical field [0001] The invention relates to a synthesis method of glabridin, which belongs to the technical field of fine chemicals. Background technique [0002] Glabridin is the most important isoflavone component in Glycyrrhiza glabra, which only exists in the cork layer and rotten roots of Glycyrrhiza glabra, accounting for 11% of the isoflavones in Glycyrrhiza glabra. Glabridin is stable at room temperature, has whitening, antibacterial, anti-oxidant, anti-cancer, anti-spasmodic, anti-inflammatory, anti-allergic, liver-protecting, free radical scavenging effects, and has a certain effect of lowering blood fat and blood pressure. It also shows good prospects for pharmaceutical development in the prevention and treatment of sclerosis and cardiovascular diseases. [0003] Currently reported chemical synthesis of glabridin has two routes. In the patent JP2006008604A, glabridin was prepared from 2,4-dimethylsulfonyloxyphenylacetic acid as a raw material, and the synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
Inventor 纪文华高乾善王晓耿岩玲林云良高红梅
Owner 山东济清科技服务有限公司
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