JP2000236843A - Production of curcumins - Google Patents

Abstract

PROBLEM TO BE SOLVED: To suppress the deterioration of curcumin, reduce the amount of an extracting solvent and produce high-purity curcumins useful for medicines, foods, colorants, or the like, by dispersing a curcumin-containing extract solution in a solvent having a polarity different from that of the extracting solvent and then fractionating the curcumin. SOLUTION: For example, Curcuma longa L. is pulverized to 250-500 μm size to thereby provide a curcumin-containing extract solution according to a solid-liquid extracting method or a Soxhlet method, or the like, using an extracting solvent such as acetone. The resultant extract solution is then dispersed in a solvent having a polarity different from that of the extracting solvent and having high safety such as hydrous ethanol, hydrous denatured ethanol or water and the curcumin is subsequently fractionated to afford curcumins. For example, a deposition fractionating method by regulation of hydrogen ions of a solution, temperature regulation or polarity regulation is used as the method for fractionating the curcumins.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing curcumins with reduced residual extraction solvent.

[0002]

2. Description of the Related Art Curcumin is included in a group of tropical and subtropical plants represented by turmeric (Curcuma longa L.), which is a perennial ginger. Turmeric is used as a coloring agent for edible spices, food and clothing, and is also used as a medicinal product in the Asian region in particular. Its pharmacological actions include bile secretion promoting action (biliary action) and internal organs (liver, pancreas). ) Function-enhancing action, anti-inflammatory action, hemostatic action, and stomachic action are known.

In addition, curcumin has recently been reported to have an effect of improving lipid metabolism in addition to an antioxidant effect and a carcinogenesis-suppressing effect.

[0004] Curcumin is generally produced by extracting an organic solvent from turmeric. For example, after turmeric is crushed to 250-500 μm, an organic solvent, specifically, a hydrophilic solvent such as ethanol, methanol, isopropyl alcohol, propylene glycol, or acetone, or a hydrophobic solvent such as hexane or ethyl acetate, etc. An extract is obtained by a solid-liquid extraction method or a Soxhlet method using a combination solvent with a solvent,
The extract is desolvated by a method such as drying under reduced pressure, and then, if necessary, purified by using a silica column.

[0005] Among them, as a method of removing the solvent, various methods such as simple distillation, fractional distillation, rectification, steam distillation, reduced pressure distillation, precision distillation, molecular distillation, heat drying, reduced pressure drying, and ventilation drying are exemplified. However, any method has a problem that several steps such as a heating step and a long processing time are required to reduce the amount of the residual solvent. Further, in the above-mentioned solvent reduction step, there is a problem in that curcumin undergoes modification and deterioration such as decomposition and polymerization during a long treatment step.

[0006] On the other hand, organic solvents include many substances having carcinogenicity, toxicity, and irritating odor, and those having low irritating properties such as water and ethyl alcohol and whose safety has been confirmed. It is preferred that it be removed as much as possible. Actually, Japanese Patent Application Laid-Open No. 3-65235 discloses a method for extracting a supercritical fluid of an organic solvent and a gas near the criticality as a method for extracting a residual solvent from a molded product such as a tablet. JP-A-292216 discloses a method for desolvating pharmaceuticals such as glycyrrhizic acid and salts thereof by supercritical carbon dioxide extraction.
No. 2 discloses a solvent extraction method for removing a solvent by bringing a pharmaceutical composition into contact with a pressurized gas, and Japanese Patent Application Laid-Open No. 6-9479 discloses a method of contacting a turmeric powder with a supercritical carbon dioxide gas. There is disclosed a method of extracting curcumin by causing the curcumin to be extracted, and a method of producing a curcumin-cyclodextrin complex or the like by adsorbing and including the extracted curcumin with cyclodextrin. However, as described above, these extraction methods and the like remove residual solvents and the like using a supercritical fluid or a pressurized gas close thereto, but require a very large-scale apparatus, and require equipment installation. The problem is that excessive initial investment is required for the purpose.

Further, Japanese Patent Application Laid-Open No. 57-8739 discloses that
As a method for reducing the organic solvent in the protein extracted from fats and oils from soybeans and rapeseed, a method in which the solvent is brought into contact with the solvent at an extraction temperature of 35 ° C. or lower in as short a time as possible is disclosed. In the case of the target, a problem arises in that the extraction efficiency is reduced in low-temperature, short-time extraction processing. Furthermore, Japanese Patent Application Laid-Open No. 5-255241 discloses a method of removing carotene as a target solvent, in which a carotene crystal is dissolved and then an inert gas is ventilated. Has a problem in that it requires heating at a high temperature, and as a result, curcumin is subject to denaturation and degradation such as decomposition and polymerization. Furthermore, adding a new residual solvent reduction step after preparing the turmeric extract dry matter when considering the actual curcumin production is expected to cause an increase in the production cost, and during the extraction step, It is desired that a residual solvent reduction step is performed.

[0008]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned conventional problems and the like, and is intended to solve the problem. The present invention provides a method for producing curcumins, which suppresses curcumin deterioration and reduces a residual extraction solvent. The aim is to provide a method.

[0009]

Means for Solving the Problems As a result of studying the above conventional problems, the present inventors disperse a curcumin-containing extract in a specific solvent different from the extraction solvent and then separate the curcumin to obtain the above object. It has been found that a method for producing curcumins can be obtained, and the present invention has been completed. That is, the method for producing curcumin of the present invention is characterized in that curcumin-containing extract is dispersed in a solvent having a different polarity from the extraction solvent, and then curcumin is separated.

[0010]

Embodiments of the present invention will be described below in detail. The method for producing curcumins of the present invention is characterized in that a curcumin-containing extract is dispersed in a solvent having a different polarity from the extraction solvent, and then curcumin is fractionated.

The curcumins to be produced in the present invention include:
Curcumin and its derivatives, for example, curcumin, demethoxycurcumin, bisdemethoxycurcumin and the like, but also semi-purified or crude curcumin as long as they do not contain impurities that are unsuitable for pharmaceuticals and foods in their purity. In addition, if necessary, a mixed composition with another compound can be a target.

The curcumin extraction raw material of the present invention can be of any origin. For example, in addition to turmeric (Curcuma longa L.), it can be extracted from plants such as mangoshjija, Indian arrow root, gajutsu, yellow gejutsu, black gejutsu, and galangard.

The curcumin-containing extract used in the present invention (hereinafter referred to as "extraction solution") is not particularly limited as long as it is a curcumin-containing extract obtained by extracting an organic solvent from the above raw materials and the like. 250-500μ
After being pulverized to m, a curcumin-containing extract obtained by a solid-liquid extraction method or a Soxhlet method using an extraction solvent, specifically, ethanol, methanol, isopropyl alcohol, propylene glycol, acetone, ethylene dichloride or the like can be used.

As the solvent for dispersing the extraction solution in the present invention, any solvent can be used as long as it has a polarity different from that of the extraction solvent.
A highly safe solvent such as hydrous denatured ethanol, water, glycerin, medium-chain fatty acid triglyceride, and edible oil is used.

The method of dispersing the extraction solution is not particularly limited, but is preferably a method of dropping in order to quickly generate a precipitate. Further, in the present invention, the temperature at the time of dispersion can be carried out at any temperature according to the solvent to be used. For a solvent such as hydrated ethanol, hydrated denatured ethanol, and water, the temperature is -20C to 100C, preferably 5C. ~ 7
It can be carried out at a temperature of 5 ° C., and any amount of solvent can be used depending on the amount of curcumin or the like to be treated and the target amount of residual extraction solvent.

The present invention can also be carried out under the conditions of distilling off the extraction solvent when dispersing the extraction solution. As the extraction solvent distillation conditions, specifically, conditions such as heating distillation conditions, aeration conditions, and reduced pressure conditions are used. By performing the process under the above-mentioned extraction solvent distillation conditions, the removal amount of the residual extraction solvent is expected to be improved, and the amount of the solvent for dropping the extraction solution is reduced, so that the entire apparatus can be reduced in size. Furthermore, the extraction solvent can be recovered at the same time, and the economics of the entire process can be improved.

In the present invention, as a method for separating curcumin after dispersion of the extraction solution, for example, a separation separation method by adjusting the hydrogen ion concentration of the solution, adjusting the temperature, adjusting the polarity, simple distillation, fractionation, rectification, steam distillation Solvent distillation methods such as vacuum distillation, precision distillation, molecular distillation, heat drying, and vacuum drying, adsorption and desorption with an ion exchange resin, etc., chromatography using a silica column, an ODS column, ion exchange chromatography, gel filtration chromatography, and the like. Can be

In the present invention thus constituted, the curcumin-containing extraction solution is dispersed in a solvent having a polarity different from that of the extraction solvent, particularly a highly safe solvent such as aqueous ethanol, aqueous denatured ethanol, and water, and then curcumin is separated. By doing so, it is possible to reduce the amount of the extraction solvent in which the residue becomes a problem,
And since it can be performed in a simple step in parallel with the extraction step, it can be performed while further suppressing the deterioration of curcumin.

[0019]

Next, the present invention will be further described with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples.

Example 1 1 g of turmeric powder of 40 g
20 mL of acetone was added, the mixture was stirred at 40 ° C. for 30 minutes, and filtered to obtain a turmeric extract. The obtained extract was slowly dropped into 15 L of water at 20 ° C. while stirring,
After continuing stirring for 30 minutes, the obtained precipitate was separated by filtration and dried overnight in a constant temperature bath at 80 ° C. to obtain 1.0 g of crude curcumin. The amount of residual acetone in the crude curcumin was 81 ppm as shown in Table 1 below.

Comparative Example 1 The extract obtained in the same manner as in Example 1 was concentrated under reduced pressure at 40 ° C. using a rotary evaporator, and then dried under reduced pressure at 65 ° C. overnight to obtain crude curcumin. Then, the obtained crude curcumin 1.1
The amount of residual acetone in g was shown in Table 1 below as a comparative example, and the amount of residual acetone was 850 ppm.

Example 2 2 L of a 10% ethanol solution was placed in a vessel equipped with a rectification tower filled with Dixon packing in a glass tube having a diameter of 1 cm and a length of 40 cm. Then, the extract obtained in the same manner as in Example 1 was slowly dropped, and after the dropping was completed, 30 minutes.
It was kept stirring for minutes. Then, the obtained precipitate was filtered off,
It was dried in a constant temperature bath at 80 ° C. overnight to obtain 1.0 g of crude curcumin. The amount of residual acetone in the crude curcumin was 190 ppm as shown in Table 1 below. Further, 60 ml of acetone containing 6% of water was recovered under the above conditions.

[Embodiment 3] 2 L of water was added to the apparatus of Embodiment 2 above.
And the extract obtained in the same manner as in Example 1 above was slowly added dropwise under reduced pressure while stirring at 65 ° C.,
After completion of the dropping, the mixture was stirred and held for 30 minutes. Next, the obtained precipitate was separated by filtration and dried in a constant temperature bath at 80 ° C. overnight to obtain 1.1 g of crude curcumin. The amount of residual acetone in the crude curcumin was 94 ppm as shown in Table 1 below. Also, under these conditions, acetone containing 11% water was 65 m
1 was collected.

[0024]

[Table 1]

As is clear from the results shown in Table 1 above, the curcumin-containing extract used in the method of the present invention was dispersed in a solvent having a different polarity from the extraction solvent, and then curcumin was separated.
In Comparative Examples Nos. 1 to 3, it was found that the amount of residual acetone was extremely reduced as compared with Comparative Example 1 out of the range of the present invention.

[0026]

According to the present invention, after the curcumin-containing extraction solution is dispersed in a solvent having a polarity different from that of the extraction solvent, the curcumin is separated to reduce the amount of the extraction solvent in which the residue becomes a problem. Provided is a method for producing curcumin, which can be carried out in a simple step parallel to the step while further suppressing the deterioration of curcumin.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Masahiko Furue 1-37, Honjo, Sumida-ku, Tokyo F-term in Lion Corporation (reference) 4B047 LB03 LG43 LP01 LP07 4C088 AB81 BA08 BA10 BA11 BA31 BA32 ZA53 ZA66 ZA69 ZA76 ZB11 ZB26 ZC21 ZC33

Claims (1)

[Claims] 1. A method for producing curcumins, comprising: dispersing a curcumin-containing extract in a solvent having a polarity different from that of an extraction solvent, and then separating curcumin.