A kind of preparation method of hydroxytyrosol

A technology of hydroxytyrosol and ethanol, which is applied in the field of chemical synthesis of natural product hydroxytyrosol, can solve the problems of poor product quality, low yield, and unsuitability for industrial production, and achieve good color, high demethylation activity, and increased Effect of demethylation activity

Active Publication Date: 2020-11-06
陕西嘉禾药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a preparation method of hydroxytyrosol, which mainly solves the problems of low yield, poor product quality and unsuitability for industrialized production in the prior art

Method used

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  • A kind of preparation method of hydroxytyrosol
  • A kind of preparation method of hydroxytyrosol

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Experimental program
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Effect test

Embodiment 1

[0024] The preparation of embodiment 1 hydroxytyrosol

[0025] At room temperature, put 115g of acetonitrile, 45.5g of 3,4-dimethoxyphenethyl alcohol, and 204g of aluminum triiodide into a dry 1000ml four-necked reaction flask, stir well, control the temperature at 10-15°C, drop Add 4 g of boron trifluoride tetrahydrofuran, drop it off, raise the temperature to reflux, and check the liquid phase after 6 hours, the reaction is complete. Cool down to room temperature, filter, add 10 g of activated carbon to the filtrate, reflux for 0.5 h, filter, recover the filtrate to dryness, and obtain a light yellow oily residue. Add 80g of dichloromethane, reflux for 2h, and slowly lower to room temperature for beating for 2h. Filter and dry to obtain 36.6g of white powdery solid, melting point 80-82°C, content above 98%, yield 95.5%.

[0026] The conditions for liquid phase detection are: Instrument: Shimadzu CTO-15C

[0027] Column: LunaC18, 4.6mm×250mm, 5μm

[0028] Mobile phase: wa...

Embodiment 2

[0032] The preparation of embodiment 2 hydroxytyrosol

[0033] At room temperature, put 140g of acetonitrile, 45.5g of 3,4-dimethoxyphenethyl alcohol, and 234g of aluminum triiodide into a dry 1000ml four-necked reaction flask, stir well, control the temperature at 10-15°C, drop Add 4.6 g of boron trifluoride tetrahydrofuran, drop it off, raise the temperature to reflux, and check the liquid phase after 5 hours, the reaction is complete. Cool down to room temperature, filter, add 10 g of activated carbon to the filtrate, reflux for 0.5 h, filter, and recover the filtrate to dryness to obtain a light yellow oily residue. Add 80g of dichloromethane, reflux for 2h, and slowly lower to room temperature for beating for 2h. Filtrate and dry to obtain 37.2 g of white powdery solid, with a melting point of 80-82° C., a content of more than 98%, and a yield of 96.8%.

[0034] (liquid phase detection condition is the same as embodiment 1)

Embodiment 3

[0035] The preparation of embodiment 3 hydroxytyrosol

[0036] At room temperature, put 180g of acetonitrile, 45.5g of 3,4-dimethoxyphenethyl alcohol, and 285g of aluminum triiodide into a dry 1000ml four-necked reaction flask, stir well, control the temperature at 10-15°C, drop Add 5.7 g of boron trifluoride diethyl ether, drop it off, raise the temperature to reflux, and check the liquid phase after 4 hours, the reaction is complete. Cool down to room temperature, filter, and recover the solvent from the filtrate to dryness, add 150g of ethanol and 10g of activated carbon to the residue, reflux for 0.5h, filter, recover the filtrate to dryness, add 70g of dichloromethane to the residue, reflux for 2h, slowly lower to room temperature and beat for 2h . Filter and dry to obtain 36g of white powdery solid, melting point 80-82°C, content above 98%, yield 93.5%. (liquid phase detection condition is the same as embodiment 1)

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Abstract

The invention provides a preparation method of hydroxytyrosol. The preparation method comprises the following steps: uniformly stirring a solvent, 3,4-dimethoxyphenethyl alcohol and aluminum triiodide, adding boron trifluoride tetrahydrofuran or boron trifluoride diethyl etherate, carrying out heating and refluxing, cooling the mixture to room temperature after the reaction is completed, filtering, adding active carbon into filtrate, filtering again, recycling filtrate till all the filtrate is recycled, obtaining a light yellow oil residue, then adding methylene dichloride, carrying out refluxing, cooling to room temperature, pulping, and filtering the material, thus obtaining white powdered solid hydroxytyrosol. According to the preparation method, complicated operation of multiple extractions in a water phase in a conventional method is avoided; the content of a product is 98 percent or above, and the quality of the hydroxytyrosol is much higher than the product quality in the prior art.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a chemical synthesis method of natural product hydroxytyrosol. Background technique [0002] Hydroxytyrosol, the chemical name is 2-(3,4-dihydroxyphenyl)ethanol. Hydroxytyrosol has a catechol structure and has strong oxidative properties. It has been applied to food and cosmetics in foreign countries for a long time. With continuous research, more medicinal values ​​of hydroxytyrosol have been discovered, such as anti-cancer , antibacterial, anti-inflammatory, and have significant effects on the prevention and treatment of arteriosclerosis, hypertension, heart disease, cerebral hemorrhage and other diseases. It is also widely used in the fields of health care products, food and cosmetics. [0003] [0004] In the prior art, the preparation of hydroxytyrosol mainly includes extraction and chemical synthesis from olive leaves, as follows: [0005] Plant extraction is obtained fro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/11C07C37/055C07C37/68
CPCC07C37/055C07C37/685C07C39/11
Inventor 肖金霞郭文华靳莎杨雪峰
Owner 陕西嘉禾药业有限公司
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