5-aminolevulinic acid hydrochloride crystal form and preparation method thereof

A technology of aminolevulinic acid hydrochloride crystal and aminolevulinic acid hydrochloride, applied in the field of 5-aminolevulinic acid hydrochloride crystal form and its preparation, can solve the problem of not paying attention to product crystal form and product quality Instability, neglect of important influences and other issues, to achieve the effect of favorable storage and transportation, mild conditions, uniform particle size and luster

CN113149854AInactive Publication Date: 2021-07-23海安艾拉新材料有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2021-07-23
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to the technical field of industrial crystallization, in particular to a 5-aminolevulinic acid hydrochloride crystal form and a preparation method thereof, and the preparation method comprises the following steps: adding a 5-aminolevulinic acid hydrochloride crude product into a specific solvent with the concentration of 0.3-0.8 g / ml, conducting dissolving and clarifying at room temperature, and conducting filtering to remove mechanical impurities so as to avoid interference on crystallization, then dropwise adding another specific solvent at room temperature, stopping dropwise adding after turbidity is generated, maintaining stirring and growing the crystal for 30 minutes or more, continuously dropwise adding a solvent with a specific multiple, separating out a large amount of crystals, conducting filtering, washing a filter cake, and conducting drying in vacuum to obtain the crystal of the 5-aminolevulinic acid hydrochloride crystal form. The product prepared by the method is a white crystal, has good solubility, short melting range and high purity, subsequent preparation of various preparations is facilitated, and a new crystal and a preparation method are provided for efficient utilization of 5-aminolevulinic acid hydrochloride.
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Description

technical field

[0001] The invention belongs to the technical field of industrial crystallization, and in particular relates to a crystal form of 5-aminolevulinic acid hydrochloride and a preparation method thereof. Background technique

[0002] 5-Aminolevulinic acid hydrochloride (English name: 5-Aminolevulinic acid hydrochloride); CAS number: 5451-09-2; Molecular formula: C 5 h 9 NO 3 .HCl; molecular weight: 167.59; chemical structure as follows:

[0003]

[0004] 5-Aminolevulinic acid hydrochloride (5-Aminolevulinic acid, 5-ALA) is an important natural amino acid ubiquitous in nature, and it is the synthetic precursor of compounds such as chlorophyll and blood red. It can be used as a plant production regulator in agriculture to increase crop yield and enhance stress resistance. It can also be used as an insecticide and herbicide. It can be used to treat acne and keratosis in medicine. It can be used as a new generation of photodynamic drugs. The treatment and diag...

Examples

Embodiment 1

[0027] Dissolve 10 grams of crude 5-aminolevulinic acid hydrochloride in 20 grams of pure water at room temperature, filter to remove mechanical impurities, slowly add 200 ml of methanol dropwise to the solution, wait until turbidity appears, suspend the dropwise addition, and continue stirring for 30 Minutes to grow the crystal, and then continue to drop the remaining methanol. After the dropwise addition is completed, filter, wash the filter cake with an appropriate amount of methanol, put the solid into a vacuum drying oven, the vacuum degree is -0.095--0.098Mpa, the temperature is 20-40°C, and the drying time is 6-8 hours to obtain the 5 -Aminolevulinic acid hydrochloride crystal form β, the X-RD powder diffraction pattern of the product has characteristic peaks at 2θ=21.0±0.5°, 23.7±0.5°, 29.7±0.5°, 30.9±0.5°, 36.2±0.5° , Solubility (25°C in water) can reach 0.60g / ml, excellent solubility.

Embodiment 2

[0029] Dissolve 10 grams of crude 5-aminolevulinic acid hydrochloride in 10 grams of pure water at room temperature, filter to remove mechanical impurities, slowly add 200 ml of ethanol dropwise to the solution, wait until turbidity appears, suspend the dropwise addition, and continue stirring for 30 Minutes to grow the crystal, and then continue to drop the remaining ethanol. After the dropwise addition is completed, filter, wash the filter cake with an appropriate amount of ethanol, put the solid into a vacuum drying oven, the vacuum degree is -0.095--0.098Mpa, the temperature is 20-40°C, and the drying time is 6-8 hours to obtain the 5 -Aminolevulinic acid hydrochloride crystal form β, the X-RD powder diffraction pattern of the product has characteristic peaks at 2θ=21.0±0.5°, 23.7±0.5°, 29.7±0.5°, 30.9±0.5°, 36.2±0.5° , Solubility (25°C in water) can reach 0.62g / ml, excellent solubility.

Embodiment 3

[0031] Dissolve 10 grams of crude 5-aminolevulinic acid hydrochloride in 10 grams of pure water at room temperature, filter to remove mechanical impurities, mix 100ml of ethanol and 100ml of isopropanol, and slowly add it dropwise to the solution until it becomes turbid , suspend the dropwise addition, continue to stir for 30 minutes to grow the crystal, and then continue to dropwise add the remaining mixed alcohol solution. After the dropwise addition is completed, filter, wash the filter cake with an appropriate amount of mixed alcohol, put the solid into a vacuum drying oven, the vacuum degree is -0.095--0.098Mpa, the temperature is 20-40°C, and the drying time is 6-8 hours to obtain the described 5-Aminolevulinic acid hydrochloride crystal form β, the X-RD powder diffraction pattern of the product has a characteristic peak at [A1], the solubility (25°C in water) can reach 0.61g / ml, and the solubility is excellent.