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Preparation method for 5-methyltetrahydrofolate basic amino acid salt compound, 5-methyltetrahydrofolate basic amino acid salt compound and application thereof

An amino acid salt compound, methyltetrahydrofolate technology, applied in the preparation of organic compounds, cyanide reaction preparation, chemical instruments and methods, etc., can solve the problems of low solubility, inconvenient use, inconvenient, etc., and achieve bioavailability High precision, easy to use, good stability

Inactive Publication Date: 2015-02-18
GUANGDONG WEILUO BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, two methods are mainly used. One is to add vitamin C and other antioxidants to 5-methyltetrahydrofolate, but it is very inconvenient in actual use, and the antioxidant effect is not very obvious.
The second is to react 5-methyltetrahydrofolate with basic metal salts such as calcium chloride to make crystalline 5-methyltetrahydrofolate (such as Chinese patent CN 1277197A, U.S. patent US 6,441,168), and make Although the chemical stability of crystal 5-methyltetrahydrofolate has been solved to a certain extent, its solubility in water is low and it is inconvenient to use (such as L-5-methyltetrahydrofolate calcium, 20 ℃ Under certain conditions, the solubility in water is only 1.07%
In addition, the formation of crystalline calcium L-5-methyltetrahydrofolate is expensive to produce

Method used

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  • Preparation method for 5-methyltetrahydrofolate basic amino acid salt compound, 5-methyltetrahydrofolate basic amino acid salt compound and application thereof
  • Preparation method for 5-methyltetrahydrofolate basic amino acid salt compound, 5-methyltetrahydrofolate basic amino acid salt compound and application thereof
  • Preparation method for 5-methyltetrahydrofolate basic amino acid salt compound, 5-methyltetrahydrofolate basic amino acid salt compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 9.2g (20mmol) L-5-methyltetrahydrofolate in batches to 6.96g (40mmol) L-arginine solution dissolved in 100mL of water, stir at room temperature for half an hour, at this time the pH is about 6.3, The solution was concentrated to dryness in vacuo to obtain 15.8 g of L-5-methyltetrahydrofolate L-arginine salt. Among them, L-5-methyltetrahydrofolate can be synthesized by using commercially available products or referring to literature (Author Zhang Yue et al., "Fine and Specialty Chemicals", Issue 22, 2005).

[0031] HPLC detection, detection conditions:

[0032] Chromatographic column: Hypersil-ODS, 5μm; 250x4mm

[0033] Mobile phase: methanol / water (2:1, pH=8.0)

[0034] Flow rate: 1.1ml / min

[0035] Detector: UV (280nm)

[0036] Column temperature: room temperature

[0037] The content of L-5-methyltetrahydrofolate in the L-arginine salt of L-5-methyltetrahydrofolate accounts for 56.0%, and the theoretical calculation value of calcium L-5-methyltetrahydrofolate...

Embodiment 2

[0039] 9.2 grams (20 mmol) of (D, L)-5-methyltetrahydrofolate were added in batches to a solution of 5.84 grams (40 mmol) of L-lysine dissolved in 100 mL of water, and stirred at room temperature for half an hour. At this time, the pH was 6.4, and the obtained solution was spray-dried to obtain 14.4 g of (D,L)-5-methyltetrahydrofolate L-lysine salt. HPLC detection condition is the same as embodiment 1. Wherein (D, L)-5-methyltetrahydrofolate is the racemate of 5-methyltetrahydrofolate, reference can be made to the literature (Author Zhang Yue et al., "Fine and Specialty Chemicals", Issue 22, 2005) etc. The method in is synthesized, and commercially available products can also be used.

[0040] The content of (D,L)-5-methyltetrahydrofolate in (D,L)-5-methyltetrahydrofolate L-lysine salt accounts for 59.1%, and the theoretical calculation value is 60.0%. Its HPLC spectrum is shown in image 3 , the compound's 1 See HNMR Figure 4 .

Embodiment 3

[0042]Add 9.2 g (20 mmol) (D, L)-5-methyltetrahydrofolate in batches to a solution of 6.2 g (40 mmol) L-histidine dissolved in 100 mL of water, and stir at room temperature for half an hour. At this time, the pH was 6.3, and the resulting solution was spray-dried to obtain 15.1 g of (D, L)-5-methyltetrahydrofolate L-histidine salt. The HPLC detection conditions were the same as in Example 1. Wherein (D, L)-5-methyltetrahydrofolate is the racemate of 5-methyltetrahydrofolate, reference can be made to the literature (Author Zhang Yue et al., "Fine and Specialty Chemicals", Issue 22, 2005) etc. The method in is synthesized, and commercially available products can also be used.

[0043] The content of L-5-methyltetrahydrofolate in (D, L)-5-methyltetrahydrofolate L-histidine salt accounts for 58.8%, and the theoretical calculation value is 59.7%. Its HPLC spectrogram is shown in Figure 5 ,. The compound's 1 See HNMR Figure 6 .

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Abstract

The invention discloses a preparation method for a 5-methyltetrahydrofolate basic amino acid salt compound. The method comprises the following step of stirring basic amino acid and 5-methyltetrahydrofolate to prepare the 5-methyltetrahydrofolate basic amino acid salt compound under the action of a solvent. The invention also discloses the 5-methyltetrahydrofolate basic amino acid salt compound prepared by the preparation method and the application of the compound as a food additive, a nutritional supplement and a medicament. The 5-methyltetrahydrofolate basic amino acid salt compound has stable chemical properties at room temperature, and the solubility of the 5-methyltetrahydrofolate basic amino acid salt compound in water is over 50 percent.

Description

technical field [0001] The invention relates to a preparation method of a 5-methyltetrahydrofolate basic amino acid salt compound, a 5-methyltetrahydrofolate basic amino acid salt compound and applications. Background technique [0002] Calcium tetrahydrofolate is mainly used as 5-formyltetrahydrofolate and its salts or 5-methyltetrahydrofolate and its salts for the treatment of macrocytic anemia caused by folic acid deficiency, and as an antidote for enhancing folic acid resistance compatibility. 5-Methyltetrahydrofolate can be used especially in pharmaceuticals and food additives, as a vitamin supplement, for the prevention of neural tube defects, and for the treatment of depression. [0003] However, 5-methyltetrahydrofolate and its salts are unstable, especially highly sensitive to oxidation, so the research on the stability of 5-methyltetrahydrofolate has always been a research hotspot. At present, two methods are mainly used. One is to add antioxidants such as vitami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07C279/14C07C277/08C07C229/26C07C227/18C07D233/64A23L1/29A61K31/519A61P7/06A61P25/00A61P25/24A23L33/00
CPCC07D487/04A23V2002/00C07D233/64A23V2200/30
Inventor 胡雅辉
Owner GUANGDONG WEILUO BIOTECH
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