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Synthetic method of hydroxytyrosol

A synthetic method, the technology of hydroxytyrosol, which is applied in the field of chemical synthesis of hydroxytyrosol, can solve the problems of high cost and poor stability of raw materials, and achieve the effects of reduced reaction cost, mild reaction conditions, and good industrial application prospects

Inactive Publication Date: 2014-03-26
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, the raw material stability of the above route is relatively poor, and the cost is relatively high
DSM has also applied for a patent on the method for preparing hydroxytyrosol using catechol as a raw material, but expensive chemical reagents such as palladium carbon are used in the route, so it is necessary to study a more economical method for synthesizing hydroxytyrosol

Method used

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  • Synthetic method of hydroxytyrosol
  • Synthetic method of hydroxytyrosol
  • Synthetic method of hydroxytyrosol

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Embodiment one: according to figure 1 Synthesis of hydroxytyrosol by the synthetic route shown

[0028] 1. Preparation of 1,2-methylenedioxybenzene (3)

[0029] Add DMSO (80ml), dichloromethane (20ml), and TBAB (1.9g, 6mmol) to a 250ml three-necked flask, and slowly heat up to 110°C. When reflux is seen, slowly add catechol ( 11g, 0.1mol) of DMSO (60mL) solution, add dropwise 50% sodium hydroxide aqueous solution (sodium hydroxide 8g, 0.2mol, water 8mL) at the same time, add dropwise for about 2h, continue to react for about 1h, and monitor the reaction by TLC Finish.

[0030] Add 100mL of water to the reaction flask, continue heating, and collect the fraction at 99-104°C. This distillate is an azeotrope of water and 1,2-methylenedioxybenzene, which is white and turbid. When the distillate is clear, it does not contain 1,2-methylenedioxybenzene. The distillate was treated to obtain a colorless transparent liquid (9.97 g, 81.7%).

[0031] NMR analysis was carried ou...

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Abstract

The invention belongs to the technical field of medicament synthesis, and in particular relates to a chemical synthetic method of hydroxytyrosol. The chemical synthetic method comprises the steps of (1) protecting two phenolic hydroxyl groups of catechol by using dichloromethane, and enabling catechol to react with dichloromethane to prepare 1,2-methylenedioxybenzene; (2) enabling 1,2-methylenedioxybenzene to react with various monoesters of oxalyl chloride to prepare 3,4-methylenedioxy phenylglyoxylic acid ester; (3) preparing 3,4-methylenedioxy phenylacetic acid by using 3,4-methylenedioxy phenylglyoxylic acid ester through a Wollff-kishner-Huang Minglong reduction reaction; and (4) reducing the 3,4-methylenedioxy phenylacetic acid by using lithium aluminum hydride, lithium borohydride or sodium borohydride to prepare 3,4-methylenedioxy phenethyl alcohol, and then removing methylene protection of the 3,4-methylenedioxy phenethyl alcohol by using boron tribromide or palladium on activated carbon to prepare hydroxytyrosol. A reactive reagent used in the synthetic method disclosed by the invention is easy to obtain and low in price, the reaction condition is mild, and the final yield of the whole reaction is 23%.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a chemical synthesis method of hydroxytyrosol. Background technique [0002] Hydroxytyrosol, also known as 3,4 dihydroxyphenylethanol, mainly exists in various parts of olives in the form of esterified oleuropein, and free hydroxytyrosol can be obtained after oleuropein is hydrolyzed. It is a natural polyphenolic compound with strong antioxidant properties. In recent years, a large number of studies at home and abroad have confirmed that hydroxytyrosol has many biopharmacological activities beneficial to human health (1) hydroxytyrosol has a positive effect on lowering blood pressure and preventing cardiovascular diseases; (2) hydroxytyrosol has a positive effect on bone (3) Hydroxytyrosol is also used in anti-cancer and anti-cancer; (4) Hydroxytyrosol has antibacterial effect; (5) Hydroxytyrosol can effectively reduce and inhibit the harm of smoking to the hu...

Claims

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Application Information

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IPC IPC(8): C07C39/11C07C37/055
CPCC07C37/055C07D317/50C07D317/54C07D317/60C07C39/11
Inventor 花尔并高英豪郁彭冀娜
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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