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A kind of preparation method of (r)-3-hydroxybutyric acid and oligomer thereof

A technology of hydroxybutyric acid and hydroxybutyrate, which is applied in the biological field, can solve the problems of short action time and acidosis, etc., reduce the risk of acidosis and metal ion overload, and prolong the action time. Effect

Active Publication Date: 2021-02-26
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 3-Hydroxybutyrate may cause acidosis following rapid absorption from the gastrointestinal tract when administered directly
However, it does not improve the problem of short duration of action

Method used

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  • A kind of preparation method of (r)-3-hydroxybutyric acid and oligomer thereof
  • A kind of preparation method of (r)-3-hydroxybutyric acid and oligomer thereof
  • A kind of preparation method of (r)-3-hydroxybutyric acid and oligomer thereof

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Experimental program
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preparation example Construction

[0046] The preparation method of the present invention comprises the following steps:

[0047] When R is methyl, ethyl, n-propyl, isopropyl and other groups, it can be prepared by the following steps:

[0048] a) Alcoholysis: Poly(R)-3-hydroxybutyric acid alcoholysis to prepare (R)-3-hydroxybutyrate monomer

[0049] The chemical reaction equation is shown in formula II

[0050]

[0051] Poly(R)-3-hydroxybutyric acid (R)-3-hydroxybutyrate can be prepared in step a) using any alcohol, such as methanol, ethanol, n-propanol, ethylene glycol, glycerol, etc., if As food, medicine or nutritional supplement, ethanol is preferred.

[0052] Suitably, the molar ratio of alcohol to poly(R)-3-hydroxybutyric acid is greater than 1:1, preferably 2:1-10:1, more preferably 3:1-6:1.

[0053] The alcoholysis in step a) is suitably carried out under the catalysis of a catalyst, which may be a Lewis acid or an organic base, preferably an inorganic acid, more preferably sulfuric acid or p-tol...

Embodiment 1

[0077] Embodiment 1 poly(R)-3-hydroxybutyric acid alcoholysis

[0078] Add 1.5L 1,2-dichloroethane and 1L absolute ethanol to a 5L three-necked flask, turn on the stirring at a speed of 150r / min, add 500g of poly(R)-3-hydroxybutyric acid after stirring for 1 minute, and stir for 3 Mix evenly for -5 minutes, then slowly add 100mL of concentrated sulfuric acid to the mixture, then slowly raise the temperature to 78°C, stop heating after 24 hours of heat preservation reaction, wait until the temperature drops below 40°C, slowly add 1L of distilled water to the reaction system, After stirring for 30 minutes, stop stirring, let stand for 30 minutes, separate layers, extract the upper aqueous phase with 500mL dichloromethane three times, combine all organic phases, wash once with 500mL saturated aqueous sodium bicarbonate solution, and then wash twice with 500mL distilled water After adding 20 g of anhydrous magnesium sulfate and drying for 2 hours, it was filtered and washed with 1...

Embodiment 2

[0079] Embodiment 2 poly(R)-3-hydroxybutyric acid alcoholysis

[0080] Add 1.5L chloroform and 1.5L methanol to a 5L three-necked flask, turn on the stirring at a speed of 150 r / min, add 500g poly(R)-3-hydroxybutyric acid after stirring for 1 minute, and stir for 3-5 minutes to mix well , then slowly add 150mL of concentrated sulfuric acid to the mixture, then slowly raise the temperature to 90°C, stop heating after 24 hours of heat preservation reaction, wait until the temperature drops below 40°C, slowly add 1L of distilled water to the reaction system, and stop after stirring for 30 minutes Stir, stand for 30 minutes, separate layers, extract the upper aqueous phase with 500mL dichloromethane three times, combine all organic phases, wash once with 500mL saturated aqueous sodium bicarbonate solution, then wash twice with 500mL distilled water, then add 20g of anhydrous sulfuric acid The magnesium was dried for 2 hours, filtered and washed with 100 mL of dichloromethane. The...

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Abstract

The invention belongs to the field of biotechnology, in particular to a preparation method and application of (R)-3-hydroxybutyric acid and oligomers thereof, including: oligomers shown in formula I wherein n=3-10, preferably n= 3-8; R can be H, straight-chain alkyl such as methyl and ethyl, branched-chain alkyl such as n-propyl and isopropyl, aralkyl such as benzyl and phenethyl, or Na, K, Ca, Metal ions such as Mg; more preferably ethyl. The (R)-3-hydroxybutyric acid oligomer in the present invention has the effect of increasing the level of ketone bodies in the body, not only can prolong the action time to achieve the effect of sustained release, but also can reduce the risk of acidosis and metal ion overload . It has the characteristics of high safety, small side effects and long acting time.

Description

technical field [0001] The invention belongs to the field of biotechnology, in particular to a preparation method and application of (R)-3-hydroxybutyric acid and its oligomers. Background technique [0002] In the liver, the intermediate products of fatty acid oxidation and decomposition are acetoacetate, (R)-3-hydroxybutyrate and acetone, which are collectively referred to as ketone bodies. Ketone bodies are a source of energy for many tissues, including the brain, during starvation and are therefore of physiological importance. The latest research shows that the presence of ketone bodies has good preventive and therapeutic effects on many diseases. These include enhanced cognitive performance, improved exercise capacity, improvements in cardiovascular conditions, diabetes, neurodegenerative diseases, and epilepsy, among others. [0003] Patent Document 1 discloses that ketone bodies can be directly administered in order to increase the level of ketone bodies in a subjec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/67C07C67/08A61P25/28A61P9/00A61P3/10A61P25/08A23L33/10
CPCA23V2002/00A23L33/10A61P3/10A61P9/00A61P25/08A61P25/28C07C69/67A23V2200/30A23V2200/322A23V2200/326A23V2200/328
Inventor 陆文超陈超
Owner TSINGHUA UNIV
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