Eriodictyol synthesis method

A synthesis method and technology for eriodictyol, applied in the biological field, can solve the problems of complex process, no technical documents for the total synthesis of eriodictyol, and high cost, and achieve the effect of high yield

Inactive Publication Date: 2016-02-24
SHAANXI JIAHE PHYTOCHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Eriodictyol can be isolated from plants, and can also be directly synthesized or semi-synthesized from hesperidin. The semi-synthesized eriodictyol is obtained by hydrolysis and demethylation of hesperidin. The publication number is CN103145670A patent introduction A new semi-synthetic process for the preparation of luteolin, which involves the preparation of the intermediate product eriodictyol, the method uses hesperidin as raw material, hydrolyzed by acidic glycolic acid aqueous solution, adding anhydrous aluminum chloride for demethylation The disadvant

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Effect test

Embodiment 1

[0026] Step 1 Add 15.2 g of isovanillin, 0.54 g of sodium methoxide, and 100 mL of acetone into a 1000 mL round bottom flask, stir at room temperature for 1 h, then add 18 g of dimethyl carbonate, and continue stirring for 4 h. Add 100 mL of water, extract three times with 300 mL of ethyl acetate, combine the organic layers, anhydrous Na 2 SO 4 After drying for 30 minutes, the ethyl acetate was distilled off under reduced pressure to obtain crude 3-methoxymethoxy-4-methoxybenzaldehyde as a yellow-green solid with a yield of 86.4%.

[0027] Step 2 Add 2,4,6-trihydroxyacetophenone 18.2g in a 1000ml round bottom flask, K 2 CO 3 82.8g, acetone 100mL, stirred at room temperature for 1h, then added MOMCl22.8ml, continued stirring for 4h, added water 100mL, extracted with ethyl acetate 300ml, combined organic layers, anhydrous Na 2 SO 4 After drying for 30 min, ethyl acetate was distilled off under reduced pressure to obtain crude 2-hydroxy-4-methoxymethoxy-6-ethoxyacetophenone a...

Embodiment 2

[0032] Step 1 Add 30.4g of isovanillin, 1.08g of sodium methoxide and 200mL of acetone into a 1000mL round bottom flask, stir at room temperature for 1h, then add 36g of dimethyl carbonate, and continue stirring for 4h. Add 200mL of water, extract three times with 600ml of ethyl acetate, and combine Organic layer, anhydrous Na 2 SO 4 After drying for 30 min, the ethyl acetate was distilled off under reduced pressure to obtain the crude product 3-methoxymethoxy-4-methoxybenzaldehyde as a yellow-green solid with a yield of 87%.

[0033]Step 2 Add 2,4,6-trihydroxyacetophenone 36.4g in a 1000ml round bottom flask, K 2 CO 3 165g, acetone 100mL, stirred at room temperature for 1h, then added MOMCl46ml, continued to stir for 4h, added water 200mL, extracted with ethyl acetate 500ml, combined organic layers, anhydrous Na 2 SO 4 After drying for 30 minutes, ethyl acetate was distilled off under reduced pressure to obtain 28 g of crude 2-hydroxy-4-methoxymethoxy-6-ethoxyacetophenone...

Embodiment 3

[0038] Step 1: Add 45g of isovanillin, 1.5g of sodium methoxide and 300mL of acetone into a 2000mL round bottom flask, stir at room temperature for 1h, then add 54g of dimethyl carbonate, and continue stirring for 4h. Add 300mL of water, extract three times with 900ml of ethyl acetate, combine organic layer, anhydrous Na 2 SO 4 Dry for 30 minutes, distill off the ethyl acetate under reduced pressure to obtain 40 g of the crude product 3-methoxymethoxy-4-methoxybenzaldehyde as a yellow-green solid, with a yield of 85%.

[0039] Step 2 Add 2,4,6-trihydroxyacetophenone 54g in a 2000ml round bottom flask, K 2 CO 3 250g, acetone 300mL, stirred at room temperature for 1h, then added MOMCl70ml, continued to stir for 4h, added water 300mL, extracted with ethyl acetate 900ml, combined organic layers, anhydrous Na 2 SO 4 After drying for 30 minutes, the ethyl acetate was distilled off under reduced pressure to obtain 38.34 g of crude 2-hydroxy-4-methoxymethoxy-6-ethoxyacetophenone a...

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Abstract

The invention provides an eriodictyol synthesis method. According to the eriodictyol synthesis method, isovanillin and 2,4,6-trihydroxyacetophenone are selected as starting materials, and eriodictyol is obtained through the following five steps: firstly, performing MOMCl protection on a hydroxyl of isovanillin; secondly, performing MOMCl protection on a hydroxyl of 2,4,6-trihydroxyacetophenone; thirdly, performing an aldol condensation reaction to generate chalcone; fourthly, performing Michael addition and cyclization; finally, carrying out MOM deprotection to obtain eriodictyol of which the total yield is 50-65%. As isovanillin and 2,4,6-trihydroxyacetophenone are selected as the starting materials, the eriodictyol synthesis method is high in yield and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a method for synthesizing erioclidinium. Background technique [0002] The CAS number of North American eriodictine is 552-58-9 molecular formula C 15 h 12 o 6 , molecular weight 288.25, molecular structure formula: [0003] [0004] Eriodictyol, also known as eriodictyol (eriodictyol), is a flavonoid widely distributed in fruits and vegetables, mainly in lemons and peanuts. Flavonoids, as free radical receptors and chain terminators, can exert antioxidant activity. The hydroxyl position and degree of hydroxylation are closely related to the antioxidant capacity of flavonoids. Flavonoids with ortho-diphenolic hydroxyl groups on the B ring have the highest antioxidant activity. powerful. According to the chemical structure of eriodictylen, eriodictyol is a flavonoid with an ortho-diphenolic hydroxyl group on the B ring, and it is speculated that eriodictyol is a na...

Claims

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Application Information

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IPC IPC(8): C07D311/32
CPCC07D311/32
Inventor 郭文华肖金霞张瑜肖红王晓莹赵景辉
Owner SHAANXI JIAHE PHYTOCHEM
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