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Process for semi-synthesizing of apiolin

A synthesis method and technology of apigenin, applied in directions such as organic chemistry, can solve problems such as unfriendly odor to human body, increase production cost, unfavorable industrial production, etc., and achieve the effects of easy control of reaction conditions, easy control, and reduction of synthesis cost.

Active Publication Date: 2006-06-28
ZHEJIANG TIANCAO BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that this method has also lost the value of industrialized production, and the process is extremely complicated and the production cost is relatively high
It is also reported that naringenin and iodine are dissolved in pyridine to react, and the yield of apigenin is better and the purity is higher, but the price of pyridine is higher, which increases the production cost, and its unfriendly smell to the human body is not conducive to industrial production. carry out

Method used

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  • Process for semi-synthesizing of apiolin
  • Process for semi-synthesizing of apiolin

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Example 1 40g naringenin, 0.5g sodium hydroxide and 30.48g iodine were dissolved in 400ml 1,4-dioxane and refluxed for 6 hours (120°C). Concentrate the reaction solution to 100ml, add 700ml of water, let stand, and filter with suction. The obtained crude product apigenin was fully dissolved with 600ml of 5% NaOH solution, then methanol was added, and the pH value was adjusted to 6 with hydrochloric acid, a large amount of crystals were precipitated, and then suction filtered. The apigenin obtained above was purified by reflux with 150 ml of acetone, filtered and dried to obtain 24 g of apigenin with a purity of 98.2%, and a yield of 60%.

Embodiment 2

[0017] Dissolve 40g of naringenin, 0.7g of potassium hydroxide and 38.10g of iodine in 500ml of 1,4-dioxane, and react in a constant temperature water bath at 100°C for 8 hours. Concentrate the reaction solution to 120ml, add 700ml of water, let stand, and filter with suction. The obtained crude product apigenin was fully dissolved with 500ml of 10% KOH solution, then 800ml of glycerin was added, and the pH value was adjusted to about 5 with hydrochloric acid, a large amount of crystals were precipitated, and then suction filtered. Wash until neutral, dry. Dissolve with 150ml dimethylformamide, add water, and precipitate. After drying, 28 g of apigenin with a purity of 98.5% were obtained, and the yield was 65.4%.

Embodiment 3

[0019] Dissolve 40g of naringenin, 0.5g of potassium hydroxide and 38.10g of iodine in 300ml of 1,4-dioxane in a constant temperature water bath of 50°C. Concentrate the reaction solution to 100ml, add 600ml of water, let stand, and filter with suction. The obtained crude product apigenin was fully dissolved with 800ml of 3% NaOH solution, then 800ml of ethanol was added, and the pH value was adjusted to 6 with hydrochloric acid, a large amount of crystals were precipitated, and then suction filtered. Wash until neutral, dry. Dissolve with 150ml dimethyl sulfoxide, filter, add water, and precipitate. Obtain 20g apigenin, its purity is 97.8%, yield 50%.

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Abstract

The invention discloses a semi compounding method for apium celery element that uses natural extract as basic raw material. It uses pomelo peel element as raw material, 1, 4-dioxy cyclohexane as reaction solvent, taking oxidative dehydrogenation reaction with iodine to form raw apium celery element. Taking multi-steps recrystallizing, the refined apium celery element would be gained. The invention is easy to operate, stable reacting condition, easy to control. The yield would be 60-70% and the purity could be over 97%. And it is low cost, no harmful to the environment.

Description

technical field [0001] The invention relates to a semi-synthetic method of apigenin using natural extracts as basic raw materials. Background technique [0002] Apigenin (apigenin) belongs to flavonoids, and is abundant in the leaves of Apium graveolens var. dulce; the whole herb of Selaginella tamariscina; and the leaves of Sabinachinensis. [0003] Apigenin exists in many plants in the form of plant yellow pigment. The pure product is yellow powder, odorless and tasteless. Is a natural antioxidant. The chemical name is 5,7,4'-trihydroxyflavone, the molecular formula and molecular weight are C 15 h 10 o 5 And 270.25, melting point 347.5 ° C, almost insoluble in water, slightly soluble in hot alcohol, soluble in dilute KOH solution. [0004] Its structure is as follows: [0005] [0006] It has been reported in the literature that apigenin has the effect of protecting the heart and treating Parkinson's disease, and can lower blood pressure and affect the central ner...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
Inventor 闫卫东曹丹邵云东
Owner ZHEJIANG TIANCAO BIOTECHNOLOGY CO LTD
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