Preparation method and application of compound 3-hydroxy-3',4'-dihydroxy-butyric acid phenethyl ester

A compound, the technology of phenethyl ester, which is applied in the fields of biology and medicine, can solve problems such as no research reports on brain fatigue, and achieve the effect of improving learning and memory decline and manic mood

Active Publication Date: 2021-12-28
XI AN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no research report on brain fatigue related to this drug
There is no research report on brain fatigue related to this drug

Method used

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  • Preparation method and application of compound 3-hydroxy-3',4'-dihydroxy-butyric acid phenethyl ester
  • Preparation method and application of compound 3-hydroxy-3',4'-dihydroxy-butyric acid phenethyl ester
  • Preparation method and application of compound 3-hydroxy-3',4'-dihydroxy-butyric acid phenethyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 3-Hydroxy-3', 4'-dihydroxy-butyric acid phenethyl ester (hydroxytyrosol hydroxybutyrate), its structure is shown in formula I:

[0061]

[0062] Preparation method one:

[0063]

[0064] Synthesis of S1, β-benzyloxybutyric acid (5)

[0065] Weigh crotonic acid (1) (2.55g, 29.7mmol) in a 150ml round bottom flask, add benzyl alcohol (3) (30ml), then add mercury acetate (9.63g, 30mmol), stir overnight at room temperature, put the flask into Cool the low-temperature condensation tank to 0°C, add 30ml of 3N sodium hydroxide within 5-10min, then add 30ml of 0.5M (0.57g) sodium borohydride in 3N sodium hydroxide aqueous solution, and keep the solution at 0°C for 3-10min. Take out and stir at room temperature for 1-2h, filter the filtrate, and extract with 75ml ether 3-4 times to remove excess benzyl alcohol. The aqueous layer was acidified to pH 2 with 10% hydrochloric acid, a large amount of white solids were precipitated, and β-benzyloxybutyric acid (5) was obtained ...

Embodiment 2

[0085] 1. Experimental materials

[0086] Hydroxytyrosol acetate was purchased from Santa Company of the United States, CAS No. 69039-02-7; ethyl β-hydroxybutyrate was purchased from Aladdin Company of the United States, CAS No. 24915-95-5.

[0087] 2. Experimental animal feeding and model establishment

[0088] In this experiment, 8-week-old adult male SD rats of 250 g were purchased from the Animal Center of Shanghai Naval Military Medical University. The rats were kept in an animal room with controllable temperature (22°C to 28°C) and humidity (60%). The lights in the room were maintained in a 12-hour day and 12-hour night cycle, and the rats were free to eat during the experiment. and water ingress. In this experiment, a sleep deprivation method was used to establish a rat model of brain fatigue. The experimental rats were divided into five groups, 10 in each group. The five groups were: (1) the normal feeding group was fed normal saline every day at the same time (her...

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PUM

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Abstract

The invention discloses a preparation method and application of a compound 3-hydroxy-3', 4'-dihydroxy-butyric acid phenethyl ester represented by formula I. Specifically, it discloses a compound whose structure is as follows: It is shown in I; it discloses that the compound shown in formula I, the optically pure isomer of the compound, the mixture of enantiomers in any ratio or the pharmaceutically acceptable salt thereof is used in the preparation of alleviating brain fatigue, improving learning and memory ability and manic symptoms application in health food and medicine.

Description

technical field [0001] The present invention relates to the fields of biology and medicine, in particular to a new compound 3-hydroxy-3',4'-dihydroxy-butyric acid phenylethyl ester and its preparation method and in the preparation of health food and medicine for improving brain fatigue Applications. Background technique [0002] In a modern society with increasingly busy lifestyles, more and more people are subjected to long-term high-intensity continuous work, or working in a high-stress environment, which leads to brain fatigue. Brain fatigue of varying degrees can impair memory acquisition and consolidation, lead to decreased attention and alertness, and trigger psychiatric symptoms such as mania and depression. Studies have shown that sleep can regulate the neuron function of the brain during memory storage, and sleep deprivation can have a significant negative impact on various functions of the body of humans and animals, especially cognition, memory, emotion, etc., us...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/675C07C67/08C07C67/31C07C51/367C07C59/125C07C41/16C07C43/23A61K31/22A61P25/28A61P25/18A23L33/10
CPCC07C69/675C07C67/08C07C67/31C07C51/367C07C41/16A61P25/28A61P25/18A23L33/10A23V2002/00C07B2200/07C07C59/125C07C43/23A23V2200/322A23V2200/30C07C51/353C07C51/09C07C69/708C07C59/195C07C69/72C07C69/612C07C43/2055C07C41/09C07C67/03A61K31/222
Inventor 龙建纲胡亚冲王永耀王珍马庆庆张豫霞蒋庆林许小红张婷华刘健康
Owner XI AN JIAOTONG UNIV
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