Synthesis method of hydroxytyrosol

A technology for the synthesis of hydroxytyrosol, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high cost, unsuitability for industrial production, poor stability of raw materials, etc., and achieve low cost and good production conditions And the effect of low equipment requirements and easy operation

Inactive Publication Date: 2012-02-08
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above routes have poor raw material stability and high cost, and are not suitable for industrial production.

Method used

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  • Synthesis method of hydroxytyrosol
  • Synthesis method of hydroxytyrosol
  • Synthesis method of hydroxytyrosol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Under the protection of argon, 0.55g (23.9mmol) of sodium chips was added to the pre-dried three-necked flask, and 1.0g (4.7mmol) of 3,4-dimethoxyphenylacetic acid methyl ester was dissolved in 20mL of anhydrous The ethanol solution was slowly dropped into the three-necked flask, and after the reaction was stable, it was heated and refluxed for 1 hour. After cooling, the product solution was acidified with hydrochloric acid, and insoluble substances were precipitated, which were removed by suction filtration under reduced pressure. ×10mL ) extraction and column separation (chloroform) to obtain hydroxytyrosol. The product is light yellow oily liquid, and the yield is 50%. 1 H NMR (400MHz, CDCl 3 ): δ= 6.60 (d, 1H), 6.58 (d, 1H), 6.43 (d, 1H), 3.47 (t, 2H), 2.52 (t, 2H); Ms m / z: 154(M + ); IR (KBr) υ: 3337, 2953, 1708, 1607, 1523, 1446, 1363, 1283, 1044, 955, 920, 855, 811, 753.cm -1 . ( figure 2 )

Embodiment 2

[0019] Under the protection of argon, add 0.27g (12mmol) of sodium chips into the pre-dried three-necked flask, and slowly dissolve 1.0g (4.2mmol) of 3,4-diethoxyphenylacetic acid methyl ester in 30mL of methanol solution under stirring Drop it into a three-neck flask, and after the reaction is stable, heat and reflux for 1 hour. After cooling, the product solution is acidified with hydrochloric acid, and insoluble substances are precipitated, which are removed by suction filtration under reduced pressure. Hydroxytyrosol can be obtained by extraction and column separation (chloroform). The product is a pale yellow oily liquid with a yield of 47%, and the NMR, mass spectrometry, and infrared data are the same as in Example 1.

Embodiment 3

[0021] Under the protection of argon, 0.55g (23.9mmol) of sodium chips was added to the pre-dried three-necked flask, and 1.0g (4.0mmol) of ethyl 3,4-diethoxyphenylacetate in 20mL of isopropyl The alcohol solution was slowly dropped into the three-necked flask, and after the reaction was stable, it was heated and refluxed for 1 hour. After cooling, the product solution was acidified with hydrochloric acid, and insoluble substances were precipitated, which were removed by suction filtration under reduced pressure. Then the clear liquid was concentrated and washed with chloroform (3 ×10mL) extraction and column separation (chloroform) to obtain hydroxytyrosol. The product is a light yellow oily liquid with a yield of 43%, and the NMR, mass spectrometry, and infrared data are the same as in Example 1.

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Abstract

The invention discloses a method for synthesizing hydroxytyrosol. With 3,4-dialkoxy alkyl phenylacetate shown as the structural general formula (I) as raw material, sodium / alcohol is used for carrying out reduction to obtain the hydroxytyrosol, and R1, R2 and R3 are respectively selected from C1-C6 alkyl or C6H5CH2. Compared with a method reported by literature, the method disclosed by the invention has the advantages that raw materials are available, cost is low, operation is simple, requirement to production condition and equipment is low, and industrialization is easy to realize.

Description

technical field [0001] The invention relates to a method for synthesizing hydroxytyrosol. Background technique [0002] Hydroxytyrosol (English name: hydroxytyrosol, chemical name: 3,4-dihydroxyphenylethanol) is a free radical-scavenging polyphenol found in pure olive oil that promotes smooth, flawless skin and has been shown to be A safe and excellent beauty product and health care product, which can promote human body function and bone growth and development, and also has outstanding effects in anti-cancer and anti-cancer, reducing and inhibiting the harm of smoking to the human body and curing cardiovascular diseases. [0003] At present, hydroxytyrosol is mainly obtained by the following methods: (1) Extracting hydroxytyrosol from waste water produced by pressing olive oil. The advantage of this method is the waste utilization of the waste water produced in the production of olive oil and the reduction of environmental pollution. However, this method consumes a large a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/11C07C37/56C07C37/055
Inventor 郭媛延永
Owner NORTHWEST UNIV(CN)
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