TW202312989A - Method for producing galangal extract containing 1'-acetoxychavicol acetate - Google Patents

Abstract

The purpose of the present invention is to provide a method that enables efficient production of a galangal extract having a high 1'-acetoxychavicol acetate content. The present invention pertains to a method for producing a galangal extract containing 1'-acetoxychavicol acetate, the method comprising an extraction step for performing extraction on a galangal starting material by using supercritical carbon dioxide or liquid carbon dioxide.

Description

Preparation method of galangal extract containing 1'-acetyloxy gamol acetate

The present invention relates to the manufacture method of the galanga extract containing 1'-acetyloxy gamol acetate.

1'-Acetyloxygaymol acetate has been reported to show physiological activities such as tumor cell proliferation inhibition and NF-κβ inhibition, and is a useful compound in food and beverages and pharmaceuticals. As a method of obtaining 1'-acetyloxygaymol acetate, there is known a method of synthesizing by chemical synthesis (for example, non-patent document 1), and extracting from galangal (scientific name: Alpinia galanga) of Zingiberaceae plant method (Patent Document 1).

However, in the chemical synthesis method, since steps such as column purification are required in the manufacturing steps, the steps are complicated, and there are also problems in terms of manufacturing efficiency and cost. On the other hand, 1'-acetyloxygamrol acetate extracted from natural galangal is better in terms of efficiency and cost than chemical synthesis. In Patent Document 1, it is described that galanga is chopped, and after a water treatment step including mixing the finely divided matter with water to obtain a slurry in order to remove impurities, the slurry is subjected to solid-liquid separation to obtain a solid (solid-liquid separation step ), a method for producing a substance containing 1-acetyloxycaymol acetate (ACA) which is extracted and separated from the aforementioned solid matter with an organic solvent such as ethanol or ethyl acetate. [Prior Art Literature] [Patent Document]

Patent Document 1: Japanese Patent Laid-Open No. 2019-94282 [Non-patent literature]

Non-Patent Document 1: Mitsui et al., Chem. Pharm. Bull. Vol. 24(10) 2377-2382(1976)

[Problem to be solved by the invention]

In the method described in Patent Document 1, a water treatment step and a solid-liquid separation step must be performed before extracting galangal with an organic solvent. With regard to the method for extracting 1'-acetyloxygaymol acetate from galanga, it is desired to develop an extract that can more efficiently obtain an extract containing a large amount of 1'-acetyloxygaymol acetate. method.

The object of the present invention is to provide a method for more efficiently obtaining a galangal extract with a higher content of 1'-acetyloxygamicol acetate. [Means to solve the problem]

The present inventors found that by extracting galanga with supercritical carbon dioxide or liquid carbon dioxide, a galanga extract with a high content of 1'-acetyloxygaymol acetate can be efficiently produced.

That is, without being limited thereto, the present invention includes the following method for producing a galangal extract containing 1'-acetyloxygamicol acetate. [1] A production method of galanga extract containing 1'-acetyloxy galangal acetate, which comprises an extraction step of extracting galanga raw material with supercritical carbon dioxide or liquid carbon dioxide. [2] The production method as in [1] above, wherein the temperature of the supercritical carbon dioxide system is 32~80°C, and the pressure is 8~40MPa. [3] The production method of [1] or [2] above, wherein the supercritical carbon dioxide system has a temperature of 35-60°C and a pressure of 20-40MPa, or a temperature of 35°C or higher but less than 60°C and a pressure of 10MPa or higher. Up to 20MPa. [4] The production method according to any one of the above-mentioned [1] to [3], wherein the temperature of the liquid carbon dioxide system is 5~30°C, and the pressure is 8~40MPa. [5] The production method according to any one of the above-mentioned [1] to [4], wherein the liquid carbon dioxide system has a temperature of 10-30°C and a pressure of 10-40 MPa. [6] The production method according to any one of the above-mentioned [1] to [5], wherein the raw material of galanga is the rhizome of galanga. [Invention effect]

According to the present invention, it is possible to provide a method for producing a galanga extract that can more efficiently obtain a galangal extract with a high content of 1'-acetyloxygamicol acetate.

The production method of the present invention is the production method of the galanga extract containing 1'-acetyloxy gaymol acetate. The manufacturing method of the galanga extract containing 1'-acetyloxy galangol acetate of the present invention comprises the extraction step of extracting the galanga raw material with supercritical carbon dioxide or liquid carbon dioxide. The production method of the present invention may also include steps other than the extraction step.

The raw material of galangal is the galangal used for extraction. In the present invention, galangal refers to galanga (scientific name Alpinia galanga) of Zingiberaceae plant. Galangal is a plant native to Southeast Asia, also known as Nanjiang (Japanese name) and Ka (Thai).

The raw material of galangal can be any part of galangal, such as rhizome, root, stem, leaf, flower, fruit, seed, whole plant, etc., or a combination of two or more of them. Among them, at least one species selected from the group consisting of rhizomes, roots and leaves of galangal is preferred. It is because the content of 1'-acetyloxygamrol acetate in these parts is relatively high. As the raw material of galangal, more preferably the rhizome and/or root of galangal, and more preferably the rhizome.

As the galangal raw material, any part of the above-mentioned galangal (raw state) may be used as it is, a dried product may be used, or a ground or cut one may be used. It is preferably a dry product, and more preferably a dried product that has been pulverized or cut. Use crushed or cut galangal because of its high extraction efficiency. The method of crushing or cutting is not particularly limited, and general methods can be used. In one aspect, the production method of the present invention may include a step of preparing galangal raw materials (raw material preparation step). The method of the present invention may include, for example, the step of preparing a crushed or cut galangal (preferably rhizome) dried product. The step of preparing the galangal raw material is preferably, for example, crushing or cutting off any part (preferably rhizome) of the above-mentioned galangal. The obtained pulverized or cut galangal dried product can be used in the extraction step as a galangal raw material.

In one aspect, in the above-mentioned extraction step, it is preferable to extract the pulverized or cut dry matter of galanga (preferably rhizome) with supercritical carbon dioxide or liquid carbon dioxide.

In the present invention, supercritical carbon dioxide (carbon dioxide in a supercritical state) or liquid carbon dioxide (carbon dioxide in a liquid state) is used as an extraction solvent to extract galanga raw material. By using supercritical carbon dioxide or liquid carbon dioxide for extraction, a galanga extract containing more 1'-acetyloxygamicol acetate can be efficiently obtained. Carbon dioxide is non-flammable, harmless and cheap, and will liquefy under the conditions of temperature and pressure above the triple point (-56.6°C, 0.52MPa). Moreover, the critical temperature of carbon dioxide is 31.1° C., and the critical pressure is 7.38 MPa, which is easy to treat as a supercritical state. Supercritical carbon dioxide or liquid carbon dioxide can separate the extract from the extraction solvent by slightly changing the pressure and temperature. Therefore, even without complicated solvent removal operations after extraction, a galanga extract containing more 1'-acetyloxycaymol acetate can be obtained. In addition, as a unique advantage of carbon dioxide, antibacterial or bactericidal effects can be expected, and it can be said that it is not only harmless to the human body, but also hygienic, and it is particularly suitable for use in food and beverages and pharmaceuticals. In one aspect, supercritical carbon dioxide is preferably used in the extraction step. The fluid in the supercritical state has a density close to that of a liquid and a large diffusion coefficient close to that of a gas, which can rapidly extract 1’-acetyloxygamicol acetate from galanga raw material.

In the extraction step, the galangal raw material is contacted with supercritical carbon dioxide or liquid carbon dioxide, and the target substance (extract) is extracted from the galangal raw material to supercritical carbon dioxide or liquid carbon dioxide. Extraction is usually performed in a vessel (extraction vessel). For example, the galangal raw material is filled in a container, and the pressure and/or temperature is raised to a specific pressure and temperature to contact with carbon dioxide in a supercritical or liquid state, so that the galangal raw material can be extracted with supercritical carbon dioxide or liquid carbon dioxide.

When supercritical carbon dioxide is used for extraction in the extraction step, the preferred temperature of supercritical carbon dioxide is 32-80° C., and the pressure is 8-40 MPa. If the temperature and pressure of the supercritical carbon dioxide are in the above-mentioned ranges, a galanga extract containing a large amount of 1'-acetyloxycaymol acetate can be obtained. In this specification, the pressure of carbon dioxide is gauge pressure. The temperature of supercritical carbon dioxide is more preferably above 35°C. The pressure of supercritical carbon dioxide is more preferably 10 MPa or more. In one aspect, the optimum temperature of supercritical carbon dioxide is 35~60°C, and the pressure is 20~40 MPa. In another aspect, the more preferable temperature of supercritical carbon dioxide is not less than 35°C and not more than 60°C, and the pressure is not less than 10MPa and not more than 20MPa. If the temperature of supercritical carbon dioxide is 35~60°C, the pressure is 20~40MPa, or the temperature is above 35°C but not 60°C, and the pressure is above 10MPa but below 20MPa, then 1'-acetyloxygamiphenol can be extracted rapidly Acetate. Furthermore, the yield of 1'-acetyloxygamrol acetate became higher. The optimum temperature of supercritical carbon dioxide is 35-60°C and the pressure is 20-40MPa, and the optimum temperature is 35-60°C and the pressure is 20-35MPa. The yield (recovery rate) of 1'-acetyloxygayrol acetate is the amount of 1'-acetyloxygayrol acetate contained in the obtained galanga extract relative to the The ratio (% by weight) of the amount (100% by weight) of 1'-acetyloxygaymol acetate contained in the galangal raw material.

In one aspect, the ratio of supercritical carbon dioxide pressure (MPa) to temperature (°C) (pressure (MPa)/temperature (°C)) is more than 0.2 and less than 1. Using supercritical carbon dioxide with a pressure-to-temperature ratio within this range, 1'-acetyloxygamrol acetate can be extracted rapidly. And there is a tendency that the yield of 1'-acetyloxygamrol acetate becomes higher.

When using liquid carbon dioxide for extraction, the optimum temperature of liquid carbon dioxide is 5~30°C and the pressure is 8~40MPa. When the temperature and pressure of the liquid carbon dioxide are within the above range, the galangal extract with high content of 1'-acetyloxy galangol acetate can be obtained. The best temperature of liquid carbon dioxide is 10~30°C, the pressure is 10~40MPa, the more preferable temperature is 15~30°C, the pressure is 10~35MPa, the most preferable temperature is 18~25°C, and the pressure is 10~35MPa. When the temperature and pressure of the liquid carbon dioxide are in the above-mentioned range, 1'-acetyloxygamrol acetate can be extracted rapidly. And, the yield of 1'-acetyloxy gaymol acetate is improved.

In the extraction step, the amount of supercritical carbon dioxide or liquid carbon dioxide used is preferably 1-100 mL, more preferably 1.5-80 mL, relative to 1 g of galangal raw material (dry weight conversion). If necessary, additives such as polar solvents may be added to carbon dioxide at about 1 to 10% by weight relative to carbon dioxide as an entrainer. The polar solvent is not particularly limited, but examples thereof include polar organic solvents such as ethanol, water, and the like, and one type or a combination of two or more types can be used. In one aspect, the polar solvent is preferably ethanol, water or a mixture thereof, preferably ethanol or an aqueous ethanol solution. This is because they can be widely used in the manufacture of food and beverages. In one aspect, the carbon dioxide used for extraction preferably does not contain solvents other than carbon dioxide such as polar solvents. This is because the content of 1'-acetyloxy gamol acetate in the obtained extract tends to increase.

The extraction time of the extraction step is preferably more than 5 minutes. In the production method of the present invention, the longer the extraction time is, the higher the yield of 1'-acetyloxygamrol acetate tends to be. On the other hand, if the extraction time is too long, the content of components other than 1'-acetyloxygaymol acetate in the galanga extract may increase. In one aspect, the extraction time is preferably less than 300 minutes, more preferably 5-240 minutes, more preferably 5-120 minutes, more preferably 5-70 minutes, particularly preferably 10-60 minutes. The above extraction time refers to the time when the galangal raw material is in contact with supercritical carbon dioxide or liquid carbon dioxide.

The production method of the present invention preferably includes a step of separating supercritical carbon dioxide or liquid carbon dioxide from the galanga extract (separation step) after the extraction step. The above separation can be carried out by reducing the pressure and/or increasing the temperature of the supercritical carbon dioxide or liquid carbon dioxide containing the galanga extract. Carbon dioxide is preferably separated from the galangal extract by reducing the pressure. Extraction of the target substance (galanga extract) is carried out by contacting galanga raw material with supercritical carbon dioxide or liquid carbon dioxide, and then by reducing the pressure of supercritical carbon dioxide or liquid carbon dioxide, it can be extracted from supercritical carbon dioxide containing galanga extract. Or liquid carbon dioxide to separate the target (galangal extract). In the present invention, the extraction step and the separation step can be carried out in different containers or in the same container. When the extraction step and the separation step can be carried out in different containers, for example, the galanga raw material is contacted with supercritical carbon dioxide or liquid carbon dioxide in an extraction container (extraction tank) for extraction, and then the supercritical carbon dioxide or liquid The carbon dioxide is introduced into the separation container (separation tank), and the pressure of the carbon dioxide is reduced in the separation tank to separate the galangal extract from the carbon dioxide. When separating supercritical carbon dioxide or liquid carbon dioxide from the galangal extract, the pressure of carbon dioxide is preferably below 7MPa, more preferably 0.1~1MPa.

In the production method of the present invention, for example, a step of removing the extracted galanga raw material (extraction residue) from the galanga extract (residue removal step) may be performed as necessary. Removal of extraction residues from the extract can be performed by known methods such as filtration.

In the production method of the present invention, when an organic solvent such as ethanol is mixed with carbon dioxide, a step of removing the organic solvent from the obtained extract (organic solvent removal step) may be performed. The method for removing the organic solvent is not particularly limited, and a generally performed method can be used. For example, drying methods such as vacuum distillation, atmospheric distillation, vacuum drying, and freeze drying can be used. When water is mixed with carbon dioxide, a step of removing water from the obtained extract (water removal step) may also be performed. Examples of methods for removing water from the extract include freeze-drying and the like.

The galangal extract obtained by the production method of the present invention contains 1'-acetyloxygamrol acetate. In the present invention, 1'-acetyloxygamrol acetate can be any one of D-form, L-form or a mixture thereof. In the production method of the present invention, since supercritical carbon dioxide or liquid carbon dioxide is used for extraction, it is estimated that the water-soluble components or water content derived from galanga can be obtained compared with the extract obtained by extraction using an organic solvent such as ethanol. Less, galanga extract with higher content of 1'-acetyloxygamrol acetate. In the production method of the present invention, for example, before extracting the galanga raw material, 1'-acetyloxygamiphenol B can be obtained even without performing the treatment of mixing the galangal raw material with water to obtain a slurry for the purpose of removing impurities. Galangal extract with high ester content.

The galangal extract obtained by the production method of the present invention is a composition containing components dissolved in supercritical carbon dioxide or liquid carbon dioxide in addition to 1'-acetyloxy galangal acetate. The galangal extract obtained by the production method of the present invention is usually liquid. In one aspect of the present invention, a galanga extract having a 1'-acetyloxygamrol acetate content of 57% by weight or more can be obtained. It is possible to obtain Gao Liang with a content of 1'-acetyloxygaymol acetate of preferably more than 60% by weight, more preferably more than 65% by weight, more preferably more than 70% by weight, and especially preferably more than 75% by weight. Ginger extract. In one aspect, the production method of the present invention can be used as a 1'-acetyloxy gaymol acetate content of 57% by weight or more (preferably 60% by weight or more, more preferably 65% by weight or more, and More preferably more than 70% by weight, especially preferably more than 75% by weight) of galangal extract. The content of 1'-acetyloxygaymol acetate in the galangal extract obtained by the production method of the present invention may be 95% by weight or less, and may be 92% by weight or less. The content of 1'-acetyloxygamrol acetate can be determined by high-speed liquid chromatography (HPLC method).

According to one aspect of the present invention, the yield (recovery rate) of 1'-acetyloxygaymol acetate from the galanga raw material can be increased. In one aspect, the amount of 1'-acetyloxygaymol acetate contained in the galangal extract obtained by the production method of the present invention is preferably the amount contained in the galanga raw material before the extraction step. More than 30% of the amount of 1'-acetyloxygaymol acetate (that is, the yield of 1'-acetyloxygaymol acetate is more than 30%). In one aspect of the present invention, the yield of 1'-acetyloxygamrol acetate is more preferably 40% or more, 50% or more, 60% or more, 70% or more or 80% or more, more preferably More than 85%, especially good is more than 90%.

The galanga extract obtained by the production method of the present invention has a high content of 1'-acetyloxy gaymol acetate, and can be used in the production of food and beverages, pharmaceuticals, and the like. The galangal extract containing 1'-acetyloxy gamol acetate produced by the production method of the present invention is also included in the present invention. And by further purifying the galanga extract obtained by the production method of the present invention by column chromatography and the like, the purity of 1'-acetyloxy gamol acetate can be further improved. The numerical range represented by the lower limit and the upper limit in this specification, that is, "lower limit ~ upper limit" includes the lower limit and the upper limit. For example, the range represented by "1~2" means 1 to 2, including 1 and 2. In this specification, any combination of the upper limit and the lower limit may be used. [Example]

The following examples illustrate the present invention in more detail, but the scope of the present invention is not limited thereto. In an embodiment, the pressure is gauge pressure.

＜Galangal ingredients＞ The dried rhizome of galangal (commercially available) containing about 3% by weight of 1'-acetyloxygamicol acetate (ACA) was pulverized to obtain a pulverized rhizome of galanga. This galanga rhizome ground material was used in the following examples and comparative examples.

<Determination method of 1’-acetyloxycaymol acetate (ACA)> (1) Determination of ACA in dried galangal rhizome (solid) 500 mL of methanol (MeOH) was added to 5 g of ground galanga rhizomes, and extracted while stirring for 30 minutes. Then, it separates into an extract liquid and a solid content by solid-liquid separation. Furthermore, 500 mL of MeOH was added to the solid content, it extracted again, stirring for 30 minutes, and the extract was obtained by solid-liquid separation. The capacity of each extract was measured, and the ACA concentration was analyzed by HPLC to determine the amount of ACA in the dried galangal.

(2) Determination method of ACA in galangal extract (supercritical or liquid carbon dioxide extract) Pre-measure the bag weight of the container where the extract is to be recovered, and compare it with the weight after extraction to calculate the weight of the extract. A specific amount of ethanol (EtOH) was added to the extract, and the extract was completely dissolved in EtOH by ultrasonic waves. Subsequently, by acetonitrile, adjusted to the range of the calibration line, the concentration of ACA was determined by HPLC.

(3) Determination of ACA in the ethanol extract (EtOH extract) of galangal A specific amount of EtOH was added to the extract, and the extract was completely dissolved in EtOH by ultrasonic waves. Subsequently, by acetonitrile, adjusted to the range of the calibration line, the concentration of ACA was determined by HPLC.

(4) Analysis conditions The content of ACA was measured using high-speed liquid chromatography (HPLC method) under the following conditions. High-speed liquid chromatography: LC-2030C (manufactured by Shimadzu Corporation) PDA detector: SPD-M30A (manufactured by Shimadzu Corporation) Detection wavelength: 220nm String: 5C18-AR-II (manufactured by Nacalai Tesque, inner diameter 4.6 mm, length 150 mm) Mobile phase (liquid A): water Mobile phase (solution B): acetonitrile Flow rate: 1.0mL/min Oven temperature: 40°C Detection: 220nm Gradient condition: B liquid concentration 10min 30vol% 30min 50vol% 31min 100vol% 40min 100vol% 41min 30vol% 50min 30vol%

<Example 1> (Sample preparation) The crushed galanga rhizome (30 g) was put into a pressure vessel, and the vessel was preheated in a water bath set at the temperature (20°C, 40°C or 60°C) shown in Table 1 . Start to introduce carbon dioxide (CO ₂ ) into the pressure vessel, raise the pressure to 30MPa, and let it stand for 10 minutes until the vessel and the preheating tube are stabilized at the same temperature. Under the pressure of 30MPa, carbon dioxide is liquid at 20°C, and is in a supercritical state at 40°C and 60°C. Samples were taken 10 minutes after the above standing for 10 minutes, and the CO ₂ (supercritical CO ₂ or liquid CO ₂ ) extract (liquid) released from the back pressure valve was recovered by the 2-stage trap. The recovered _CO2 extract was used as a sample. The weight of the _CO2 extract and the ACA content (ACA concentration) (% by weight) were determined. The capacity of the pressure vessel used in the examples and comparative examples was 106 mL.

<Example 2> The crushed galanga rhizome (30 g) was fed into a pressure vessel, and the vessel was preheated in a water bath set at the temperature shown in Table 1. Start to introduce carbon dioxide into the pressure vessel, increase the pressure to the pressure shown in Table 1, and let it stand for 10 minutes until the vessel and the preheating tube are stabilized at the same temperature. After standing for 10 minutes, the sample was taken 10 minutes later, and the CO ₂ (supercritical CO ₂ ) extract (liquid) released from the back pressure valve was recovered by the 2-stage trap. Determine the weight of the _CO2 extract and the ACA content.

<Examples 3-8> The crushed galangal rhizome (30 g or 15 g) was fed into a pressure vessel, and the vessel was preheated in a water bath set at the temperature shown in Table 1. Start to introduce carbon dioxide into the pressure vessel, increase the pressure to the pressure shown in Table 1, and let it stand for 10 minutes until the vessel and the preheating tube are stabilized at the same temperature. After standing for 10 minutes, time-lapse samples were taken at specific time intervals, and the CO ₂ (supercritical CO ₂ or liquid CO ₂ ) extract (in liquid form) released from the back pressure valve was recovered by the 2-stage trap. Determine the weight of the _CO2 extract and the ACA content.

<Example 9> The crushed galangal rhizome (30 g) was fed into a pressure vessel, and the vessel was preheated in a water bath set at the temperature shown in Table 2. Start to introduce carbon dioxide into the pressure vessel, increase the pressure to the pressure shown in Table 2, and let it stand for 10 minutes until the vessel and the preheating tube are stabilized at the same temperature. After standing for 10 minutes, samples were taken after 60 minutes, and the CO ₂ (supercritical CO ₂ ) extract (in liquid form) released from the back pressure valve was recovered by the 2-stage trap. Determine the weight of the _CO2 extract and the ACA content.

<Example 10> The crushed galanga rhizome (30 g) was fed into a pressure vessel, and the vessel was preheated in a water bath set at the temperature shown in Table 2. Start to introduce carbon dioxide and EtOH (carbon dioxide: EtOH (flow ratio) = 9:1) into the pressure vessel, increase the pressure to the pressure shown in Table 2, and let it stand for 10 minutes until the container and the preheating tube stabilize at the same temperature. After standing for 10 minutes, samples were taken after 60 minutes, and the EtOH-containing CO ₂ (supercritical CO ₂ or liquid CO ₂ ) extract (liquid) released from the back pressure valve was recovered by the second-stage trap. The weight and ACA content of the obtained extract were measured.

Tables 1 to 2 show the amount (g) of ground galangal rhizome (raw material) fed into the container in Examples 1 to 10. Table 1~2 shows the extraction conditions (temperature and pressure of CO ₂ , time, flow rate of CO ₂ ) using supercritical CO ₂ or liquid CO ₂ . The time (extraction time) shown in Tables 1 to 2 is the time from the above-mentioned standing for 10 minutes after the introduction of carbon dioxide to sampling. scCO ₂ in the "Extraction" column in the table means extraction with supercritical carbon dioxide, liquid CO ₂ means extraction with liquid carbon dioxide, scCO ₂ (or liquid CO ₂ )+EtOH means supercritical (or liquid) carbon dioxide containing EtOH Do the extraction.

＜Comparative examples 1~7＞ Feed 5 g of ground galangal rhizome into a container, add 100 mL of EtOH aqueous solution with the concentration shown in Table 3, and stir at room temperature and normal pressure for 30 minutes for extraction. Subsequently, solid-liquid separation was carried out with a Nuche suction filter to obtain an extract. Furthermore, extraction and solid-liquid separation by addition of EtOH aqueous solution were repeated 2 times for the solid residue, and a total of 3 extracts were obtained. The extract was concentrated by an evaporator, and then freeze-dried to obtain an EtOH extract. The EtOH extract was used as a sample of the comparative example. The weight and ACA content (ACA concentration) of the EtOH extract were determined.

<Evaluation of samples> The total amount (mg) of 1'-acetyloxygamicol acetate (ACA) contained in the fed galanga raw material (galanga rhizome crushed product) was set as 100%, The ratio of the ACA amount (mg) contained in the galangal extract (supercritical _CO2 extract, liquid _CO2 extract, EtOH-containing _CO2 extract, or EtOH extract) was defined as the ACA yield (%) . The ACA content rate in the galangal raw material is the ratio (% by weight) of ACA contained in 100% by weight of the galangal raw material. Yield (%)=100×(weight of galanga extract×ACA content (concentration) in galanga extract)/((amount of galanga raw material fed in)×(ACA content rate in galanga raw material)) Regarding the _CO2 extracts (samples 1-25) obtained in Examples 1-8, the ACA yield and ACA content are shown in Table 1. Regarding the extracts (samples 26-30) obtained in Examples 9-10, the ACA yield and ACA content are shown in Table 2. Regarding the EtOH extracts (samples 1'-7') obtained in Comparative Examples 1-7, the ACA yield and ACA content are shown in Table 3.

By extracting galanga raw materials with supercritical carbon dioxide or liquid carbon dioxide, it is possible to effectively obtain a galanga extract with a higher content of 1'-acetylcariamol acetate than that extracted with ethanol. [Industrial availability]

The present invention is useful in the fields of food and drink, pharmaceuticals, and the like.

Claims (6)

A method for producing a galangal extract containing 1'-acetyloxy galangol acetate, which comprises an extraction step of extracting a galanga raw material with supercritical carbon dioxide or liquid carbon dioxide. Such as the production method of claim 1, wherein the temperature of the supercritical carbon dioxide system is 32~80°C, and the pressure is 8~40MPa. The manufacturing method of claim 1 or 2, wherein the supercritical carbon dioxide system has a temperature of 35-60°C and a pressure of 20-40MPa, or a temperature of 35°C to 60°C and a pressure of 10MPa to 20MPa. The manufacturing method of Claim 1 or 2, wherein the temperature of the liquid carbon dioxide system is 5-30°C, and the pressure is 8-40MPa. The manufacturing method of Claim 1 or 2, wherein the temperature of the liquid carbon dioxide system is 10~30°C, and the pressure is 10~40MPa. The manufacturing method of claim 1 or 2, wherein the raw material of galangal is the rhizome of galangal.