JPS5934710B2 - Method for producing a molecular compound of allantoin and ornithine - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel allantoin derivative, and more particularly to a method for producing a novel molecular compound of allantoin and ornithine.

This molecular compound of allantoin and ornithine is a new compound in which 1 mole of each is bonded to each other. This new compound can be obtained by subjecting allantoin and ornithine to a heating reaction in a solvent, and then distilling off the solvent from the reaction product.

The solvent used in the reaction is water, methyl alcohol,
Examples include lower alcohols such as ethyl alcohol and isopropyl alcohol, polyhydric alcohols such as ethylene glycol, glycerin, and sorbitol, lower ketones such as acetone, hydrophilic organic solvents such as dioxane, and mixtures of two or more of these. Water or a solvent containing water is preferred from the viewpoint of speed and amount of solvent used.

The type of solvent varies depending on the amount of solvent used, but in order to know when the reaction is complete, it is important to know that after the reaction is complete, there is an amount that can dissolve at least the molecular compound of allantoin and ornithine produced in the reaction product. preferable.

The reaction temperature is not limited until the solvent used in the reaction boils, but the reaction rate is slow at room temperature, so it is preferably 50°C or higher.

In addition to the method of reacting allantoin and ornithine in a solvent, the present invention includes a method in which a compound obtained by adding an acid such as hydrochloric acid or sulfuric acid to ornithine is dissolved in a solvent in which ornithine is dissolved but an alkali metal salt of the acid is not dissolved; For example, it is added to ethyl alcohol, an alkali metal hydroxide or an alkali metal carbonate is added to the mixed composition, and a heating reaction is carried out to liberate ornithine and convert the acid into an alkali metal salt, and then the alkali metal salt is converted into an alkali metal salt. Either allantoin is added to the ornithine solution obtained by filtration and heated to react, and the resulting new compound is precipitated, or the solvent is distilled off from the ornithine solution, allantoin and a solvent are added to the resulting syrupy ornithine, and the resulting new compound is precipitated. The desired new compound can be obtained by heating the mixed composition to cause ornithine and allantoin to react, and by distilling off the solvent from the reaction product.

' Still another embodiment of the invention is an addition compound of ornithine with an acid, such as ornithine hydrochloride or sulfate, and an alkali metal hydroxide or alkali metal carbonate that converts the acid into an alkali metal salt. and allantoin are added to a solvent, the mixed composition is heated to react allantoin and ornithine, and the solvent is distilled off from the resulting reaction product to obtain a mixture of the new compound and the alkali metal salt. This can be used as it is depending on the purpose, or the salt can be separated to obtain a new compound.

The properties of this new compound are as follows.

The solubility of allantoin alone at room temperature is 0 in water.
．． 6wt%, 1.0wt% to glycerin, 50v
0.3Wt01 for 01% ethyl alcohol! On the other hand, as shown in Table 1, this new compound has a solubility of 40.5 wt (f) in water and 12.3 wt (f) in 50% ethyl alcohol. The solubility in water is 22.1 wt% in water and 6.7 wt% in 50v01(f) ethyl alcohol, which is 22-37 times higher than the solubility of allantoin alone.

In addition, the infrared absorption spectra of allantoin and ornithine, a new compound of the present invention, ornithine and allantoin, were determined. Figure 1 shows the spectrum of allantoin, and Figure 2 shows the spectrum of the new compound of the present invention. In comparison, Figure 2 shows 1780CTL-1 and 1720CTL-1 (1780CTL-1 and 1720CTL-1 (
It was observed that the two peaks of -CO-NH9-CO-) disappeared, and no cyclic imide was present, while a new peak that appeared to be due to a tertiary hydroxyl group appeared at 1150 and 1. In addition, the X-ray spectrum of the new compound is that of allantoin.
No peaks shown in the line spectra are found.

From the above, it seems that the new compound was obtained by the reaction between the hydroxyl group of allantoin in the enol form and the α-amino group of ornithine in a solvent.

Therefore, this new compound is not simply a mixture of allantoin and ornithine, but a combination of both at a ratio of 1 mole each. Allantoin has a calming effect on allergic skin, cell proliferation, lysis of the corneal cortex, and removal of necrotic tissue, while ornithine has the effect of detoxifying ammonia and promoting liver function, and is used in pharmaceuticals and cosmetics. It will be done.

However, as mentioned above, allantoin has a low solubility in solvents, so its function is minute and its range of application is limited. On the other hand, the solubility of the new compound of the present invention in a solvent is several tens of times higher than that of allantoin, and about 20 to 40 times higher than that of pure allantoin. It has the efficacy of allantoin and ornithine, and has no side effects, so it can be used as a medicine and can also be added to cosmetics, creams, ointments, etc. to sufficiently increase their efficacy.

Next, the present invention will be explained with reference to Examples, but the present invention is not limited thereto.

Example 1 In a four-bottle flask equipped with a stirrer, a thermometer, and a reflux condenser, 1,609 parts of ethyl alcohol, 16,89 parts of ornithine hydrochloride, and 5 parts of potassium hydroxide were added.

6 g was added, and the solvent was refluxed while stirring, and the reaction was allowed to proceed for 3 hours.

After the reaction was completed, the mixture was cooled to room temperature, the by-produced potassium chloride was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain syrupy ornithine 13.09. This ornithine, 15.89 g of allantoin, and 150 ml of water were charged into the reactor again and reacted at 80° C. for 2 hours with stirring. After the reaction was completed, water was distilled off under reduced pressure to obtain 27.59 pale yellow powder (theoretical yield: 95%). When this material was subjected to infrared spectroscopy and X-ray analysis, it was found to be a molecular compound of allantoin and ornithine. Example 2 Isopropyl alcohol 809, ornithine hydrochloride 8.
49, a mixture of 2.09% sodium hydroxide was reacted for 3 hours according to Example 1, and then cooled to room temperature, the by-produced sodium chloride was filtered, and the filtrate 87.39% and allantoin 7.99% were returned to the reactor. The reactor was charged and reacted for 5 hours while the solvent was refluxed.

After the reaction was completed, the mixture was cooled to room temperature and filtered to obtain 13.39 pale yellow powder (theoretical yield: 92%). When this material was subjected to infrared spectroscopy and X-ray analysis, it was found to be a molecular compound of allantoin and ornithine.
Example 3 Water 150TILI1 Ornithine Hydrochloride 16.8f! , allantoin 15.89 and sodium hydroxide 4.09 were charged into a reactor and reacted at 80° C. for 2 hours.

After the reaction, water was distilled off under reduced pressure to obtain a pale yellow powder of 34.7%. When this material was subjected to infrared spectroscopy and X-ray analysis, it was confirmed that it was a mixture of molecular compounds of allantoin and ornithine and sodium chloride.

[Brief explanation of the drawing]

FIG. 1 shows an infrared absorption spectrum of allantoin, and FIG. 2 shows an infrared absorption spectrum of a molecular compound of allantoin and ornithine obtained by the KBr method.

Claims (1)

[Claims] 1. A method for producing a molecular compound of allantoin and ornithine, which comprises subjecting allantoin and ornithine to a heating reaction in a solvent.