Pyrroloquinoline quinone in free form

A compound and manufacturing method technology, applied in the direction of organic chemistry, can solve the problems of poor solubility, inefficiency, and cost of PQQ, and achieve the effect of good crystallinity and low alkali metal content

Inactive Publication Date: 2012-07-18
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the case of ion exchange resins, the free form of PQQ is poorly soluble and requires a large amount of extraction liquid, which in turn requires a subsequent concentration step, making the process inefficient
Also, when extracting with an organic solvent, the extraction device is made suitable for the organic solvent, so it is expensive

Method used

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  • Pyrroloquinoline quinone in free form
  • Pyrroloquinoline quinone in free form
  • Pyrroloquinoline quinone in free form

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] A reagent (trade name: BioPQQ) of MITSUBISHI GAS CHEMICAL COMPANY, INC. was used as a raw material PQQ disodium salt. The purity of PQQ disodium salt was 99.0% as determined by UV absorption on high performance liquid chromatography.

[0118] 2 g of the above disodium salt were added to 198 g of water to obtain an aqueous disodium salt solution. NaOH was added to the resulting solution to adjust the pH to 9. To this solution, 7.7 g of a solution obtained by diluting concentrated hydrochloric acid (from Wako Pure Chemical Industries, Ltd.) by 50% with water was added to adjust the pH to 0.9. After stirring for 30 minutes, the precipitated solid was filtered, washed with water and isopropanol. The material was dried overnight at 50°C under reduced pressure. The collected red crystals weighed 1.6 g. Na analysis showed that PQQ in free form with a Na content of 0 and thus no sodium was obtained by this simple method. The powder X-ray diffraction result of the free form...

Embodiment 2

[0120] The raw material (PQQ disodium salt) in Example 1 was dissolved in water. Sodium hydroxide was added to the solution to adjust the pH to 8, after which sodium chloride was added to precipitate PQQ trisodium salt. The precipitated PQQ trisodium salt was then washed with ethanol and dried. This salt was used in subsequent experiments.

[0121] 0.9 g of PQQ trisodium salt was dissolved in water (60 g). While stirring, about 2 g of concentrated hydrochloric acid was added thereto. The resulting solution had a pH of 0.6. After stirring overnight, the solution was filtered, the residue was washed with isopropanol and dried under reduced pressure to yield 0.35 g of a red solid. The results of powder X-ray diffraction and Na analysis of the resulting red solid were similar to those of Example 1, showing no residual Na in the red solid. It is shown as crystals of pyrroloquinoline quinone in free form.

Embodiment 3

[0123] To a mixed solution of 3.5 g of concentrated hydrochloric acid and 3.5 g of water was added 1 g of the same PQQ disodium salt solid as in Example 1 to adjust the pH of the solution to 1. After stirring at room temperature for 1 hour, the solution was filtered. The residue was washed with water and dried under reduced pressure to obtain 0.79 g of a red solid. The molar ratio of Na to PQQ in the resulting red solid was 0.06, indicating a small amount of sodium remained in the solid.

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Abstract

Disclosed are: a method for easily producing pyrroloquinoline quinone in the free form without using an organic solvent or an ion-exchange resin; and high-purity crystals of the pyrroloquinoline quinone in the free form. Specifically disclosed are: a method for producing pyrroloquinoline quinone in the free form, which comprises a process wherein a solution obtained by dissolving an alkali metal salt of pyrroloquinoline quinone and having a pH of 1.5 or less is prepared so as to obtain a precipitate; and high-purity crystals of the pyrroloquinoline quinone in the free form.

Description

[0001] Cross References to Related Applications [0002] This application benefits from Japanese Patent Application No. 2009-255056 filed on November 6, 2009. The disclosures of the aforementioned applications are incorporated herein by reference. field of invention [0003] The present invention relates to a method for producing pyrroloquinoline quinone in free form and high-purity crystals obtained therefrom. Background technique [0004] Pyrroloquinoline quinone (hereinafter sometimes referred to as "PQQ") has been proposed as a possible new vitamin (eg, Nature, vol. 422, April 24, 2003, p832) as a useful dietary supplement , cosmetics, etc. have attracted a lot of attention. PQQ exists not only in bacteria but also in eukaryotic molds and yeasts, and plays an important role as a coenzyme. In addition, PQQ has been found to have many physiological activities, for example, cell growth-promoting activity, anti-cataract (anti-cataract) activity, activity of preventing an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 池本一人枝广纯一
Owner MITSUBISHI GAS CHEM CO INC
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