JP3560302B2 - Method for producing alcoholic beverage - Google Patents

Description

【００３０】
【表２】

【００３１】
表１及び表２において、
第１工程の使用量：脱脂ごま種子１００部に対する部
Ｓ_１：アルコール性飲料中の固形分濃度（％）
Ｃ_１：アルコール性飲料中のリグナン配糖体濃度（％）
Ｃ_３：アルコール性飲料に含まれる固形分中のリグナン配糖体濃度（％）
Ｃ_４：アルコール性飲料に含まれる固形分中のセサミノールトリグルコシド濃度（％）
Ａ−１：ＢＥＴ表面積が３００ｍ^２／ｇであり且つ気孔率が０．７０ｍｌ／ｇであるスチレン−ジビニルベンゼン共重合体製の高分子系吸着剤
Ａ−２：ＢＥＴ表面積が７８０ｍ^２／ｇであり且つ気孔率が１．００ｍｌ／ｇであるスチレン−ジビニルベンゼン共重合体製の高分子系吸着剤
ａ−１：ＢＥＴ表面積が５００ｍ^２／ｇであり且つ気孔率が０．７５ｍｌ／ｇであるシリカゲル
ａ−２：ＢＥＴ表面積が３３０ｍ^２／ｇであり且つ気孔率が０．７６ｍｌ／ｇである活性アルミナ
ａ−３：ＢＥＴ表面積が３５０ｍ^２／ｇであり且つ気孔率が１．００ｍｌ／ｇであるＯＤＳシリカゲル
【００３２】
【発明の効果】
既に明らかなように、以上説明した本発明には、ごま種子由来の優れた生理活性を有するリグナン配糖体が溶解したアルコール性飲料を手軽に製造することができるという効果がある。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a method for producing an alcoholic beverage, and more particularly to a method for producing an alcoholic beverage in which lignan glycosides derived from sesame seeds are dissolved. Sesame seeds include, in addition to oil-soluble lignans such as sesamin, sesamolin, sesaminol, and sesamolinol, non-oil-soluble lignans having a structure in which saccharides having phenolic hydroxyl groups such as sesaminol and pinoresinol and saccharides are glucoside-bonded. It is known that glycosides are contained, and it is known that the lignan glycosides have various physiological activities in addition to excellent antioxidant activity against biological lipids. The present invention relates to a method for producing an alcoholic beverage in which sesame seed-derived lignan glycoside having excellent physiological activity is dissolved.
[0002]
[Prior art]
2. Description of the Related Art It has been widely practiced to immerse dried vegetation, fruits, nuts, and the like containing Japanese and Chinese herbal components in alcoholic beverages, extract the components contained therein, and obtain alcoholic beverages in which the components are dissolved. Therefore, it is conceivable to immerse sesame seeds or crushed or ground sesame seeds in alcoholic beverages, extract lignan glycosides contained therein, and obtain an alcoholic beverage in which the lignan glycosides are dissolved.
[0003]
However, when sesame seed is used as it is as a material to be extracted for alcoholic beverages, lignan glycosides contained therein are not extracted into alcoholic beverages at all. In addition, when crushed or ground sesame seeds are used as the material to be extracted, the lignan glycosides contained therein are only slightly extracted in alcoholic beverages, and the oils and fats contained in the sesame seeds elute. As a result, the obtained alcoholic beverage becomes cloudy or has an oily odor separated into layers. As the material to be extracted, there is an oil residue obtained as a residue when the sesame seed is pressed and oiled. The oil residue includes those obtained from roasted sesame seeds (roasted sesame seeds) and those obtained from unroasted sesame seeds (non-roasted sesame seeds). However, oil slag obtained from roasted sesame seeds is subject to the extraction of alcoholic beverages because most of the lignan glycosides are thermally decomposed and have a roasting smell and marked coloring depending on the roasting conditions. Not suitable as a material. The oil residue obtained from non-roasted sesame seeds has a high water content because it is subjected to steaming treatment prior to oil extraction, so that a few days after oil extraction, the proteins and the like contained in the oil residue have been altered and have an off-flavor. Therefore, even if such an oil residue is immersed in liquor as it is, the resulting alcoholic beverage has an unpleasant flavor.
[0004]
It is known that an extract containing lignan glycosides of high purity can be obtained from the oily residue of sesame seeds or non-roasted sesame seeds by solvent extraction and various separation or purification operations (JP-A-6-116282, JP-A-6-116282). 6-306093). However, obtaining an extract containing such a lignan glycoside with high purity requires complicated operations such as extraction, separation, and purification, resulting in extremely high costs, and in the process of food use, It is not suitable to use such an extract as it is as a material to be extracted for alcoholic beverages, for example, due to the use of an organic solvent that cannot be provided to the alcoholic beverage. The solvent-soluble components including lignan glycosides are directly extracted from the oil residue of sesame seeds and non-roasted sesame seeds using an aqueous solvent, and the lignan glycosides are extracted by a simple operation such that the solvent is separated from the extract. It is also known that an extract containing the same can be obtained (Japanese Patent Publication No. 26342/1986). However, since this extract has high hygroscopicity and easily deteriorates, it is very poor in handleability as a material to be extracted for alcoholic beverages.
[0005]
[Problems to be solved by the invention]
The problem to be solved by the present invention is to provide a method for easily producing an alcoholic beverage in which a lignan glycoside derived from sesame seed and having excellent physiological activity as described above is dissolved.
[0006]
[Means for Solving the Problems]
Thus, the present inventors have studied to solve the above-mentioned problems, and as a result, using non-roasted defatted sesame seed as a material to be extracted, a specific extraction treatment, a specific adsorption treatment and a specific desorption / elution treatment are applied to this. It has been found that a method in which lignan glycosides derived from sesame seeds are dissolved in an alcoholic beverage by combining them in this order is correct and suitable.
[0007]
That is, the present invention relates to a method for producing an alcoholic beverage, which includes the following first step, second step, and third step.
First step: extracting hot water-soluble components from non-roasted defatted sesame seeds using hot water of 50 ° C. or higher to obtain an extract in which the hot water-soluble components are dissolved. Second step: obtained in the first step The resulting extract is brought into contact with a polymer-based adsorbent made of a vinyl aromatic hydrocarbon-based polymer to adsorb the adsorptive component contained in the hot water-soluble component in the extract to the polymer-based adsorbent, Step of obtaining a polymer-based adsorbent to which the adsorptive component has been adsorbed Third step: The polymer-based adsorbent obtained in the second step was adsorbed to the polymer-based adsorbent using alcoholic beverages having an alcohol content of 35 degrees or more. A step of desorbing and eluting the lignan glycoside contained in the adsorptive component to obtain an alcoholic beverage in which the lignan glycoside is dissolved.
In the present invention, the non-roasted defatted sesame seeds to be subjected to the first step include: 1) non-roasted defatted sesame seeds after mechanically squeezing oil from sesame seeds; 2) crushing the sesame seeds with a mill or the like. , Non-roasted defatted sesame seeds after extracting oil with an organic solvent such as hexane, etc. In any case, non-roasted defatted sesame seeds having a residual oil content of 10% by weight or less are preferably used. preferable.
[0009]
In the first step of the present invention, hot water-soluble components are extracted from non-roasted defatted sesame seeds using hot water. The temperature of the hot water used for the extraction is 50 ° C. or higher, preferably 80 ° C. or higher. The present invention does not particularly limit the usage ratio of the hot water to the non-roasted defatted sesame seeds. Usually, the hot water is 500 to 1200 parts by weight per 100 parts by weight of the non-roasted defatted sesame seeds. It is preferable that the hot water is 700 to 1000 parts by weight per 100 parts by weight of the defatted sesame seeds. A known extraction device such as a batch-type extraction device, a semi-counterflow multistage extraction device, or a countercurrent continuous extraction device can be used for the extraction.
[0010]
When impurities such as sesame are contained in the obtained extract, such impurities can be removed by a known method such as centrifugation, pressure filtration, and vacuum filtration. The extract from which contaminants have been removed has the hot water-soluble component contained in the non-roasted defatted sesame seeds dissolved therein.
[0011]
In the second step of the present invention, the extract obtained in the first step is brought into contact with a polymer adsorbent made of a vinyl aromatic hydrocarbon-based polymer so that the adsorptive component contained in the extract is converted into the polymer. Adsorb to the system adsorbent. The present invention does not particularly limit the polymer-based adsorbent made of a vinyl aromatic hydrocarbon-based polymer used for adsorption. Examples thereof include: 1) a polymer-based adsorbent made of a styrene-divinylbenzene copolymer 2) a high molecular weight adsorbent made of an alkylstyrene-styrene-divinylbenzene terpolymer substituted with an alkyl group having 4 to 18 carbon atoms; Molecular adsorbents can be advantageously applied. When a polymer-based adsorbent made of a styrene-divinylbenzene copolymer is used, the present invention does not particularly limit the particle shape, particle size, etc., but the BET surface area is 50 m ² / g or more and the porosity is (Helium porosity, the same applies hereinafter) is preferably 0.1 ml / g or more, particularly preferably a BET surface area of 80 to 1000 m ² / g and a porosity of 0.3 to 1.5 ml / g. preferable. The present invention does not particularly limit the usage ratio of the polymer-based adsorbent, and is usually 1/5 to 1/50 times that of the extract, but 1/10 to 1/30 times that of the extract. Is preferred.
[0012]
The present invention does not particularly limit the method of bringing the extract into contact with the polymer adsorbent. Examples of the method include: 1) a method of passing the extract through a column filled with the polymer adsorbent; ) A method in which a polymer-based adsorbent is added to the extract and agitated, etc., may be mentioned. Of these, the method 2) is preferable. The temperature at which the extract is brought into contact with the polymer adsorbent is usually 100 ° C. or lower, but is preferably 30 to 70 ° C. Thus, by bringing the extract into contact with the polymer-based adsorbent, the adsorptive component contained in the hot water-soluble component in the extract is adsorbed to the polymer-based adsorbent. When the two are brought into contact with each other by the method 2), the polymer adsorbent having the adsorbable component adsorbed thereon is removed by a known method such as decantation, centrifugation, or filtration.
[0013]
In the third step of the present invention, lignan glycosides contained in the adsorptive component adsorbed on the high molecular weight adsorbent are desorbed and eluted from the high molecular weight adsorbent obtained in the second step using liquor. Alcohol used for desorption and elution has an alcohol content of 35 degrees or more, but preferably has an alcohol content of 40 degrees or more. As such liquors, various synthetic liquors or mixed liquors called recycled liquors can be applied in addition to distilled liquors such as whiskey, brandy, vodka, shochu, and awamori. The temperature at which the lignan glycoside is desorbed and eluted is usually about room temperature, but preferably 5 to 25 ° C. The present invention does not particularly limit the use ratio of liquors to the polymer-based adsorbent. Usually, alcohol is used in an amount of 0.5 to 6 times the amount of the polymer-based adsorbent. It is preferred to use up to 4 times the amount of alcohol. The present invention does not particularly limit the method of desorbing and eluting lignan glycosides from the polymer-based adsorbent. Examples of the method include: 1) Alcoholic liquor in a column packed with a polymer-based adsorbent having adsorbable components adsorbed thereon. , And 2) a method in which a high molecular weight adsorbent to which an adsorbent component is adsorbed is added to liquor and stirred. When the lignan glycoside is desorbed and eluted by the method 2), the polymer adsorbent after the desorption and elution is separated by a known method such as decantation, centrifugation, or filtration.
[0014]
Thus, the lignan glycoside is desorbed and eluted from the polymer adsorbent to obtain an alcoholic beverage in which the lignan glycoside is dissolved. This alcoholic beverage usually contains lignan glycosides derived from sesame seed at a ratio of about 0.5 to 10% by weight. The lignan glycoside contained here is a lignan glycoside having a phenolic hydroxyl group in the molecule and glucose, such as 1) 1 molecule of sesaminol per 1 molecule of glucose. Sesaminol glucoside in which 3 molecules are glucoside-linked, 2) pinoresinol glucoside in which 1 to 3 molecules of glucose are glucoside-linked to 1 molecule of pinoresinol, 3) sesamolinol glucoside in which glucose is glucoside-linked to sesamolinol, Among them, sesaminol glucoside, especially sesaminol triglucoside is included as a main component.
[0015]
The alcoholic beverage of the present invention can appropriately contain various additives approved for food additives such as flavors, fruit extracts, coloring agents, sweeteners, stabilizers and the like. The alcoholic beverage of the present invention can be used by adding it to various soft drinks, or mixing it with solid foods such as cakes, kneaded products such as sausages, and gel foods such as puddings.
[0016]
BEST MODE FOR CARRYING OUT THE INVENTION
Preferred embodiments of the present invention include the following 1) to 5).
1) First, 900 parts by weight of hot water at 100 ° C. was added to 100 parts by weight of non-roasted defatted sesame seeds containing 0.990% by weight of a lignan glycoside, and the mixture was stirred. Obtain parts by weight (first step). Next, 35 parts by weight of a dry particulate polymer adsorbent (BET surface area: 300 m ² / g, porosity: 0.70 ml / g) made of a styrene-divinylbenzene copolymer was added to the above extract, After stirring for a time, the solution is separated to obtain 40 parts by weight of a wet polymer-based adsorbent (second step). Finally, 100 parts by weight of a liqueur having an alcohol content of 60 ° C. was passed at 20 ° C. through a glass column filled with the polymer adsorbent in a wet state, and the alcohol in which 0.921% by weight of the lignan glycoside was dissolved was dissolved. Obtain 100 parts by weight of an alcoholic beverage having a temperature of 57 degrees (third step).
[0017]
2) Into a glass column filled with 40 parts by weight of a wet polymer adsorbent obtained through the first and second steps similar to the above 1), 100 parts by weight of a liqueur having an alcohol content of 45 ° C at 20 ° C. The mixture is passed to obtain 100 parts by weight of an alcoholic beverage having an alcohol content of 43 degrees in which lignan glycoside is dissolved at 0.869% by weight.
[0018]
3) A glass column filled with 40 parts by weight of a wet polymer adsorbent obtained through the first and second steps similar to the above 1) was charged with 20 parts by weight of 100 parts by weight of a liqueur having an alcohol content of 75 ° C at 20 ° C. The mixture is passed through to obtain 100 parts by weight of an alcoholic beverage having an alcohol content of 71 degrees in which lignan glycoside is dissolved at 0.831% by weight.
[0019]
4) First, 700 parts by weight of hot water at 85 ° C. was added to 100 parts by weight of non-roasted defatted sesame seeds containing 0.990% by weight of lignan glycoside, and the mixture was stirred to separate solids. Obtain parts by weight (first step). Next, 20 parts by weight of a dry particulate polymer adsorbent (BET surface area: 780 m ² / g, porosity: 1.00 ml / g) made of a styrene-divinylbenzene copolymer was added to the above-mentioned extract, After stirring for a time, the solution is separated to obtain 25 parts by weight of a wet polymer-based adsorbent (second step). Finally, 100 parts by weight of a liqueur having an alcohol content of 60 ° C. was passed at 20 ° C. through a glass column filled with the above-mentioned wet polymer adsorbent, and the alcohol in which the lignan glycoside was dissolved at 0.869% by weight was passed. Obtain 100 parts by weight of an alcoholic beverage having a temperature of 57 degrees (third step).
[0020]
5) In the first step of the above 1), hot water of 60 ° C. was used in place of the hot water of 100 ° C., and in the same manner as in the above 1), the alcohol content in which the lignan glycoside was dissolved at 0.851% by weight was used. Obtain 100 parts by weight of a 57 degree alcoholic beverage.
[0021]
Hereinafter, the configuration and effects of the present invention will be specifically described with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following examples and comparative examples, parts mean parts by weight, and% means% by weight.
[0022]
【Example】
Test Category 1 (Manufacture of alcoholic beverages)
-Example 1
First, 100 parts of non-roasted defatted sesame seeds containing 0.990% of lignan glycosides (non-roasted defatted sesame seeds having a residual oil content of 8.6% after pressing and squeezing sesame seeds) were added to 100 parts of hot water at 100 ° C. After adding 900 parts and stirring for 5 minutes, the mixture was filtered under reduced pressure to obtain 700 parts of an extract (first step). Next, 35 parts of a polymer-based adsorbent made of a styrene-divinylbenzene copolymer having a BET surface area of 300 m ² / g and a porosity of 0.70 ml / g was added to 700 parts of the extract (1 part of the extract). / 20 times), stirred at 60 ° C. for 3 hours, and then decanted to obtain 40 parts of a wet polymer adsorbent (second step). Finally, 40 parts of the wet polymer adsorbent is packed in a glass column, and 100 parts of a liqueur having an alcohol content of 60 degrees (2.9 times the amount of the polymer adsorbent) is added to the column at 20 ° C. The solution was passed to obtain 100 parts of an alcoholic beverage having an alcohol content of 57 degrees in which 0.921% of lignan glycoside was dissolved (third step).
[0023]
-Examples 2 to 5, Comparative Examples 1 to 4
Using the same non-roasted defatted sesame seeds as in Example 1, operations were performed under the conditions of the first to third steps shown in Table 1 to obtain alcoholic beverages in which lignan glycosides were dissolved.
[0024]
Comparative example 5
900 parts of 80% ethanol water at 60 ° C. was added to 100 parts of the non-roasted defatted sesame seeds as in Example 1, and the mixture was stirred for 1 hour, and then filtered under reduced pressure to obtain 700 parts of an extract. The solvent was distilled off from this extract under reduced pressure to obtain 16.4 parts of a paste having a solid content of 50%. 16.4 parts of this paste was dissolved in 83.6 parts of Shochu having an alcohol content of 35 degrees to obtain 100 parts of an alcoholic beverage.
[0025]
Test Category 2 (Analysis of manufactured alcoholic beverages)
For the alcoholic beverages obtained in Examples 1 to 5 and Comparative Examples 1 to 5, the solid content concentration in the alcoholic beverage, the lignan glycoside concentration in the solid content, The sesaminol triglucoside concentration and the lignan glycoside concentration in the alcoholic beverage were determined. The results are summarized in Table 2.
[0026]
-Solid content concentration in alcoholic beverage Take ₁ part of alcoholic beverage W of each example, distill water and ethanol under reduced pressure, and use freeze dryer (Tokyo Rikakiki FDU-540). After freeze-drying, the weight W ₂ of the obtained solid content was measured, and the solid content concentration S ₁ (%) in the alcoholic beverage was calculated by the following formula 1.
(Equation 1)
Solid content concentration S ₁ (%) = (W ₂ / W ₁ ) × 100
[0027]
・ The lignan glycoside concentration and sesaminol triglucoside concentration in the solid content, and the lignan glycoside concentration in alcoholic beverages For each of the alcoholic beverages in each example, the filtrate filtered through a Millipore filter was rapidly processed under the following conditions. It was subjected to liquid chromatography, and analyzed the lignan glycoside concentrations C ₁ and sesaminol tri glucoside concentration C ₂ in alcoholic beverages. From these analytical values, the lignan glycoside concentration C ₃ (%) and the sesaminol triglucoside concentration C ₄ (%) in the solid content were calculated by the following equations 2 and 3. The results are summarized in Table 2.
[Equation 2]
Lignan glycoside concentration C ₃ (%) = (C ₁ / S ₁ ) × 100
[Equation 3]
Sesaminol triglucoside concentration C ₄ (%) = (C ₂ / S ₁ ) × 100
Here, the lignan glycoside concentration was represented by the total amount of sesaminol mono, di, triglucoside and pinoresinol di, triglucoside. Sesaminol mono, di and triglucosides as standard samples were obtained by the method described in Phytochemistry, Vol. 35, 773-776 (1994). Pinoresinol diglucoside was obtained from Biosci, Biotech, Biochem. 56, 2087-2088 (1992), and pinoresinol triglucoside obtained by the method described in JP-A-6-116282 were used.
[0028]
..High-performance liquid chromatography conditions Stationary phase: Develosil ODS-10 (manufactured by Nomura Chemical Co., Ltd.)
Column diameter: 6 mm, column length: 250 mm
Developing solvent: 30% methyl alcohol aqueous solution to 80% methyl alcohol aqueous solution, linear gradient for 40 minutes Developing solvent flow rate: 1 ml / min Detector: UV (290 nm)
[0029]
[Table 1]

[0030]
[Table 2]

[0031]
In Tables 1 and 2,
Amount used in the first step: part S _{1 based on} 100 parts of defatted sesame seeds: solid content concentration (%) in alcoholic beverage
C ₁ : Lignan glycoside concentration in alcoholic beverage (%)
C ₃ : Lignan glycoside concentration (%) in solid content contained in alcoholic beverage
C ₄ : Sesaminol triglucoside concentration (%) in solid content contained in alcoholic beverage
A-1: A polymer-based adsorbent made of a styrene-divinylbenzene copolymer having a BET surface area of 300 m ² / g and a porosity of 0.70 ml / g A-2: a BET surface area of 780 m ² / g Polymeric adsorbent a-1 made of a styrene-divinylbenzene copolymer having a porosity of 1.00 ml / g: a BET surface area of 500 m ² / g and a porosity of 0.75 ml / g Silica gel a-2: an activated alumina having a BET surface area of 330 m ² / g and a porosity of 0.76 ml / g a-3: an activated alumina having a BET surface area of 350 m ² / g and a porosity of 1.00 ml / g A certain ODS silica gel
【The invention's effect】
As already clear, the present invention described above has an effect that an alcoholic beverage in which a lignan glycoside having excellent physiological activity derived from sesame seed is dissolved can be easily produced.

Claims (4)

A method for producing an alcoholic beverage, comprising the following first step, second step, and third step.
First step: extracting hot water-soluble components from non-roasted defatted sesame seeds using hot water of 50 ° C. or higher to obtain an extract in which the hot water-soluble components are dissolved. Second step: obtained in the first step The resulting extract is brought into contact with a polymer-based adsorbent made of a vinyl aromatic hydrocarbon-based polymer to adsorb the adsorptive component contained in the hot water-soluble component in the extract to the polymer-based adsorbent, Step of obtaining a polymer-based adsorbent to which the adsorptive component has been adsorbed Third step: The polymer-based adsorbent obtained in the second step was adsorbed to the polymer-based adsorbent using alcoholic beverages having an alcohol content of 35 degrees or more. A step of desorbing and eluting the lignan glycoside contained in the adsorptive component to obtain an alcoholic beverage in which the lignan glycoside is dissolved The method for producing an alcoholic beverage according to claim 1, wherein in the first step, hot water of 80 to 100C is used. 2. A high-molecular-weight adsorbent made of a styrene-divinylbenzene copolymer having a BET surface area of 80 to 1000 m ² / g and a porosity of 0.3 to 1.5 ml / g in the second step. Or the method for producing an alcoholic beverage according to 2. 4. The method for producing an alcoholic beverage according to claim 1, wherein the third step uses alcoholic beverages having an alcohol content of 40 degrees or more.