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Composition containing L-carnitine and beta-hydroxybutyric acid compounds

A technology of hydroxybutyric acid histidine and hydroxybutyric acid, applied in the field of medicine, can solve the problems of expensive, ineffective, mineral balance imbalance and the like

Pending Publication Date: 2019-03-01
BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] While pursuing weight loss through a ketogenic diet has many advantages, however, there are significant barriers to pursuing and maintaining a ketogenic lifestyle, such as difficulty transitioning into a ketogenic state, and most people are limited by their ability to enter ketosis ;The quickest way to deplete the glucose stores in the body is through fasting combined with exercise, and for people who get their pleasure from eating cakes, candy, bread, etc., this dietary adjustment, which is emotionally harsh on the body industry, And it's extremely challenging; there are uncomfortable physical and mental states such as lethargy and dizziness when transitioning into ketosis
[0011] Although it has been reported that ketogenic medical foods or exogenous ketone supplements can aid in the transition to ketosis, ketogenic fats such as medium-chain triglycerides (MCT oil) are usually not absorbed by the gastrointestinal system to help induce ketosis. well-tolerated doses; whereas beta-hydroxybutyrate (βHB) and acetoacetate taken orally in their free acid forms are expensive and ineffective in producing long-lasting ketosis
Sodium salts are used to buffer the free acid form of βHB, but this creates a potentially harmful sodium overload and imbalance in mineral balance at therapeutic levels of ketosis

Method used

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  • Composition containing L-carnitine and beta-hydroxybutyric acid compounds
  • Composition containing L-carnitine and beta-hydroxybutyric acid compounds
  • Composition containing L-carnitine and beta-hydroxybutyric acid compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation method of embodiment 1, compound (Iaa):

[0065]

[0066] 1.04 g (10 mmol) of 3-hydroxybutyric acid, 8 mL of acetone were added to a 100 mL round bottom flask. Dissolve 1.61g (10mmol) of L-carnitine in 3mL of pure water, and add 1mL of 10N (10mmol) aqueous sodium hydroxide solution into the solution. Slowly drop the prepared L-carnitine solution into the reaction flask, and react for 5 minutes after the dripping is completed, remove the solvent from the reaction solution in a water bath at 40°C under reduced pressure to obtain a colorless oil, add 80 mL of acetone to the flask, Stir and crystallize, filter, and wash the filter cake with acetone and vacuum-dry to obtain 2.58 g of a white solid, with a yield of 90%.

[0067] Chemical Formula: C 11 h 22 NO 6Na; 1H NMR (D 2 O): δ1.12(3H,d),2.12~2.41(4H,m),3.14(9H,s),3.34(2H,dd),4.04~4.09(1H,m),4.47~4.50(1H, m).

Embodiment 2

[0068] Embodiment 2: the preparation of following formula compound (IIaa)

[0069]

[0070] 1.04 g (10 mmol) of 3-hydroxybutyric acid, 16 mL of acetone were added to a 100 mL round bottom flask. Dissolve 1.61g (10mmol) L-carnitine in 16mL pure water, add 0.37g (5mmol) calcium hydroxide powder to the solution, stir and heat to 80°C for 2 hours, then drop the suspended L-carnitine solution Put it into a reaction flask, heat it to 60°C and stir for 2 hours, and then dissolve it. Remove the solvent under reduced pressure in a water bath at 40°C to obtain a milky white oil. Add 80 mL of acetone to the flask, stir and crystallize, filter, and filter cake After washing with acetone and vacuum drying, 1.76 g of white product was obtained, with a yield of 86%.

[0071] Chemical Formula: C 22 h 44 N 2 o 12 Ca; 1 HNMR (D 2 O): δ1.13(3H,d),2.11~2.40(8H,m),3.15(18H,s),3.36(4H,dd),4.05~4.13(2H,m),4.47~4.51(2H, m).

Embodiment 3

[0072] Example 3 Preparation of L-carnitine-β-hydroxybutyrate arginine (wherein the molar ratio of L-carnitine to β-hydroxybutyrate arginine is 1:1): add 2.78g to a 100mL round bottom flask (11 mmol) β-hydroxybutyrate arginine, add 10 mL of acetone and 3 mL of purified water. Dissolve 1.61g (10mmol) of L-carnitine in 3mL of pure water, and add 1mL of 10N (10mmol) sodium hydroxide solution into the solution. Slowly drip the prepared L-carnitine solution into the reaction flask. After the dripping, react for 5 minutes. Remove the solvent from the reaction solution in a water bath at 40°C under reduced pressure to obtain a colorless oil. Add 80 mL of acetone to the flask. After stirring for 20 minutes, a white solid precipitated out, which was filtered, and the filter cake was washed with acetone and then vacuum-dried to obtain 3.92 g of a white product, with a yield of 89%.

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Abstract

The invention provides a composition containing L-carnitine and a beta-hydroxybutyric acid compound, and specifically provides a composition containing the L-carnitine and at least one beta-hydroxybutyric acid compound. The beta-hydroxybutyric acid compound comprises beta-hydroxybutyrate, a beta-hydroxybutyric acid precursor or a combination thereof; and preferably, the L-carnitine and beta-hydroxybutyric acid amino acid exist in the composition in a form of intramolecular salt. The invention furthermore provides a preparation method of the L-carnitine-beta-hydroxybutyrate. The composition provided by the invention is high in stability, high in bioavailability and significant in weight loss effect and ketogenic effect; and the preparation method provided by the invention is easy and convenient to operate.

Description

technical field [0001] The invention belongs to the technical field of medicine, specifically the invention relates to a composition comprising L-carnitine and β-hydroxybutyrate compound, and the invention also relates to the preparation of L-carnitine-β-hydroxybutyrate in medicine and food additives application in technology. Background technique [0002] Obesity has become a serious public health problem. In recent years, the number of obese patients in the world has increased day by day. The number of deaths due to obesity is second only to smoking. The International Obesity Conference released a report on the number of deaths from related diseases caused by obesity in the world More than the number of people who died of starvation worldwide during the same period. Obesity can also induce serious diseases such as diabetes and cardiovascular disease, which is the enemy of human health and longevity. [0003] Drugs for the treatment of obesity include: appetite suppressan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/205A61K31/19A61P3/04A61P3/00A61P5/50A61P39/06
CPCA23K20/105A23K20/142A23L33/10A23L33/175A61K31/19A61K31/205A61K9/16A61K9/20A61P3/00A61P3/04A61P5/50A61P39/06
Inventor 袁建栋孙占莉丁海峰
Owner BRIGHTGENE BIO MEDICAL TECH (SUZHOU) CO LTD
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