JP6009160B2 - Fragrance imparting agent having natural herbal-like hop fragrance, beverage comprising the same, and method for producing the same - Google Patents

Description

  The present invention relates to an aroma imparting agent having a natural herbal-like hop aroma, a beverage to which a natural herbal-like hop aroma is imparted, and a method for producing the same.

  It is known that the scent imparted to beverages has a great influence on the character formation of beverage products. For example, hops are known to impart a refreshing bitterness and aroma to beer, and the aroma derived from hops has a great influence on the character formation of beer-taste beverages such as beer and sparkling liquor. Hop flavor is expressed as "floral-like", "herbal-like", "fruit-like" or "citrus-like", and expresses various aromas depending on the choice of hop varieties and how hops are used in the brewing process. There have been various reports on the control method of the scent.

  A hop aroma can be imparted to various beverages using a hop essential oil extract or the like, and there are commercially available products. For example, Hopsteiner's Hop oil type dry. However, since this is a processed product of hop essential oil existing in hop itself, it is quite different from the natural hop fragrance felt in beer drinks, and it is somewhat close to the fragrance of hop itself. As far as the present inventors know, there have been no reports or materials on materials that give a more natural and beer-like hop aroma.

  On the other hand, the unique “Fukumika” that you feel when you drink beer and the aroma after drinking are attracting attention in recent years. The hop aroma is composed of hop essential oil contained in hop lupulin grains. When a specific material example is given about hop essential oil, linalool is a typical terpene compound contained in hop essential oil, and is a substance which gives a floral feeling. In addition, about 300 or more kinds of compounds constituting essential oils such as myrcene and α-, β-pinene as monoterpenes, α-humulene and β-caryophyllene as sesquiterpenes have been identified to date.

  Thus, although existence of various aroma components derived from hops is known, studies on aroma and chemical components in beverages have been limited (see Non-Patent Documents 1 to 5). That is, the correspondence between specific fragrances and chemical components is not clear, and there are few known chemical components particularly related to fragmented fragrance characteristics.

  In Japanese Patent Publication No. 11-506604 (WO96 / 39480, Patent Document 1), an aqueous residue obtained by fermenting an extraction residue obtained by extracting alpha acid or hop oil from hops, “Hop Flavor” It is disclosed that it is used as a “medicine to be given to a beverage”. However, what is used here is an extraction residue of hop oil, not hop itself, and chemical components related to flavor in the water extract are not studied at all.

Special table hei 11-506604

T. Kishimoto et al., J. Agric. Food Chem., 54, 8855-8861, 2006 G. T. Eyres et al., J. Agric. Food Chem., 55, 6252-6261, 2007 V. E. Peacock, et al., J. Agric. Food Chem., 28, 774-777, 1980 K. C. Lam et al., J. Agric. Food Chem, 34, 763-770, 1986 V. E. Peacock et al., J. Agric. Food Chem., 29, 1265-1269, 1981

  An object of the present invention is to provide an aroma imparting agent having a natural herbal-like hop aroma, a beer-taste beverage imparted with a natural herbal-like hop aroma, and a method for producing the same.

The present inventors have found that a more natural herbal-like hop fragrance can be imparted to beverages and the like by using a hop-derived component obtained by subjecting the components in the hop to substance conversion by yeast, not simply the hop itself. It was. And in the obtained hop origin component, it succeeded in specifying the component related to natural herbal-like hop aroma. In the process, not only substances that move from hops into solution and remain relatively stable, but also substances that are identified for the first time as a result of the action by yeast, that is, substances that are produced by substance conversion by yeast, are naturally It was found to be important for showing a good herbal-like hop flavor. From these results, the present inventors feel a natural and high-quality hop fragrance, specifically, a natural herbal-like hop fragrance, by controlling the content of the specific component in the beverage within a predetermined range. It was found that a beer-taste beverage can be produced.
The present invention is based on these findings.

  That is, according to the present invention, the following inventions are provided.

(1) Two or more components selected from G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol;
3-methyl-1-pentanol, hop component D, hop component E, Octanoic acid 2-phenylethyl ester, and methyl 2-methoxy-6-pentane An aromatizing agent having a natural herbal-like hop fragrance, comprising a component of group G2 consisting of Methyl 2-methoxy-6-pentadecenoate.
[here,
The hop components A, B, C, D and E are respectively described below with respect to the retention time of the internal standard substance borneol when measured by gas chromatography / mass spectrometry (GC / MS) under the following analysis conditions. In the spectrum data having the difference in appearance time (minutes) of the retention time in Table 1 and indicating the response amount with respect to the m / z value detected at the retention time, the m / z value is 50 or more and the response amount Among the 15 peaks selected from the order of increasing number, at least the peaks of the m / z values shown in Table 1 are included:

[GC / MS analysis conditions]
Capillary column: HP-INNOWAX (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm)
Oven temperature: 40 ° C., 0.3 min-3 ° C./min→240° C., 20 min Carrier gas: He, 10 psi Air transfer Line temperature: 240 ° C.
MS ion source temperature: 230 ° C
MSQ pole temperature: 150 ° C
Front inlet temperature: 200 ° C

(2) The fragrance imparting agent according to the above (1), which is obtained by adding hops to a medium containing sugar and a nitrogen source and bringing the hops into contact with yeast.
(3) A beverage having a natural herbal-like hop fragrance comprising the fragrance imparting agent of (1) or (2).
(4) A beer-taste beverage provided with a natural herbal-like hop fragrance, comprising the fragrance imparting agent of (1) or (2),
When the beverage is extracted with a C18 solid phase column and measured by gas chromatography / mass spectrometry (GC / MS) under the following analysis conditions, the concentration of β-eudesmol is 0.5 ppb to 7 ppb, and A beer-taste beverage in which the component concentration specified as the response ratio (%) of the quantitative ion to the ion 110 m / z of the internal standard substance borneol added so as to be 25 ppb in the sample satisfies the conditions of Table 2 described later :
[GC / MS analysis conditions]
Capillary column: HP-INNOWAX (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm)
Oven temperature: 40 ° C., 0.3 min-3 ° C./min→240° C., 20 min Carrier gas: He, 10 psi Air transfer Line temperature: 240 ° C.
MS ion source temperature: 230 ° C
MSQ pole temperature: 150 ° C
Front inlet temperature: 200 ° C
Monitoring ions: m / z = 69, 85, 87, 104, 110, 126, 128, 137
Ions used for quantification:
Borneol (internal standard) m / z = 110
β-Udesmol m / z = 149.

(5) The beer-taste beverage according to (3) or (4), which is a malt beverage.
(6) The beer-taste beverage according to any one of (3) to (5), which is a fermented beverage.
(7) The beer-taste beverage according to any one of (3) to (5), which is a non-fermented beverage.
(8) The beer-taste beverage according to any one of (3) to (7), comprising the fragrance imparting agent of (2) and a pre-solution of a beverage not containing a hop-derived component.
(9) The beer-taste beverage according to (8) above, wherein the pre-beverage solution containing no hop-derived component is obtained by fermenting a pre-fermentation solution without adding hops.
(10) The beer-taste beverage according to any one of (3) to (7), comprising the fragrance imparting agent of (2) and a pre-solution of a beverage containing a hop-derived component.
(11) The beer-taste beverage according to (10), wherein the beverage containing a hop-derived component is obtained by fermenting a pre-fermentation solution containing hops.
(12) Add hops to a medium containing sugar and a nitrogen source, and contact with yeast to obtain the fragrance imparting agent of (1) or (2),
The manufacturing method of the drink in which the natural herbal-like hop fragrance | flavor in any one of said (3)-(11) including adding the obtained aroma imparting agent to the pre-solution of a drink was provided.
(12) The method according to (12), wherein the beverage pre-solution does not contain a hop-derived component.

  ADVANTAGE OF THE INVENTION According to this invention, the fragrance | flavor imparting agent which has a natural herbal-like hop fragrance | flavor, and the beer taste drink provided with the natural herbal-like hop fragrance are provided. In the present invention, hops are not added to the pre-fermentation liquid of the beer-taste beverage and fermented, but by adding an aromatizing agent prepared in advance separately from the pre-beverage liquid, to the pre-beverage liquid, A beer-taste beverage to which a desired natural herbal-like hop incense is imparted can be obtained. For this reason, by adjusting the addition amount of the fragrance imparting agent to the beverage prior to the beverage, the strength of the herbal-like hop fragrance in the beverage can be easily adjusted according to the demands of consumers and the like.

  Therefore, by adding a fragrance imparting agent according to the present invention to a pre-solution of a beverage that does not contain hop-derived components, a beverage that is originally free of hop-derived components can be obtained with the characteristic and natural desired in the present invention. A hop aroma can be imparted. On the other hand, by adding the fragrance imparting agent according to the present invention to the pre-beverage solution containing the hop-derived component, the beverage is prepared, and in addition to the fragrance inherent in the beverage, the desired fragrance is enhanced instead of the fragrance , Emphasis or change the type of fragrance. For this reason, this invention is advantageous at the point which can provide the new type of drink calculated | required by a consumer. In addition, there has been no known fragrance imparting agent having such a natural and high-quality hop fragrance, and the ability to easily adjust the strength of the herbal-like hop fragrance in beverages shortens the development time of new products and reduces costs. It is also advantageous from the viewpoint.

The spectrum data regarding the hop component A obtained in Test Example 2 are shown. The spectrum data regarding the hop component B obtained in Test Example 2 are shown. The spectrum data regarding the hop component C obtained in Test Example 2 are shown. The spectrum data regarding the hop component D obtained in Test Example 2 are shown. The spectrum data regarding the hop component E obtained in Test Example 2 are shown.

Detailed description of the invention

Aroma imparting agent The aroma imparting agent according to the present invention has a natural herbal-like hop aroma,
Two or more components selected from G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol;
G2-group components consisting of 3-methyl-1-pentanol, hop component D, hop component E, 2-phenylethyl octoate, and methyl 2-methoxy-6-pentadecenoate. The more types of ingredients in Group G1 used for the fragrance imparting agent, the more advantageous for clarifying the natural herbal-like hop aroma.

  Preferably, the fragrance imparting agent contains 3 or more components selected from the G1 group having 5 components, more preferably 4 or more types, and still more preferably all 5 types of the G1 group.

Among the components contained in the fragrance imparting agent, hop components A, B, C, D and E are components specified by the following.
That is, the hop components A, B, C, D and E are each retention time of the internal standard substance borneol when measured by gas chromatography / mass spectrometry (GC / MS) under the above-mentioned GC / MS analysis conditions. Each of them has a feature of having an appearance time difference (minutes) of the retention times shown in Table 1 below. Further, the hop components A, B, C, D, and E have spectral response values corresponding to m / z values detected at the respective retention times, and the m / z values are 50 or more and the response amounts are Among the 15 peaks selected in descending order (preferably in 10 peaks, more preferably in 8 peaks, and even more preferably in 5 peaks), at least the peaks of the m / z values shown in Table 1 are included It is what More preferably, the hop components A, B, C, D, and E have a m / z value of 50 or more in the spectrum data indicating the amount of response to the m / z value detected at the retention time indicated by each of the hop components A, B, C, D, and E. Three peaks out of the five peaks selected in descending order of quantity are the m / z value peaks shown below.

According to a more preferred aspect of the present invention, the hop components A, B, C, D, and E are the retention time appearance time difference (minutes) and spectral data detected at each retention time as shown in Table 1. Among the 15 peaks selected in descending order of response amount, the m / z values of the molecular weight spectra of the three peaks and the magnitude relationship between the response amounts in the m / z values are as follows: It can be specified by the relational expression.
(Relational expression)
・ Hop component A: 69 m / z ≧ 55 m / z> 97 m / z
・ Hop component B: 83 m / z> 57 m / z> 71 m / z
Hop component C: 79 m / z> 107 m / z> 122 m / z
Hop component D: 57 m / z≈85 m / z> 73 m / z
・ Hop component E: 87 m / z> 60 m / z> 74 m / z
(Here, the magnitude relationship in the case of “≈” indicates that there is no difference in the response amounts of the peaks, and even if there is a difference, the range of the difference is 10% or less of the total response amount, preferably Means less than 5%).

Furthermore, when specifying the hop components A, B, C, D, and E, in addition to the peak values of each m / z value based on the spectrum data shown in Table 1, as required, FIGS. By referring to each of them, the peak of the m / z value that should be additionally referred to specify each hop component can be appropriately selected. For example, the following can be additionally exemplified for each hop component, but the present invention is not limited thereto.
-Hop component A: 109, 128
-Hop component B: 55, 111, 126
-Hop component C: 91, 137
-Hop component D: 55, 97, 106
Hop component E: 56, 90, 102

  The hop components A, B, C, D and E are identified as described above because component identification based on known information such as literature was impossible as a result of mass spectrometry. If there is, it is easy to understand what each of the hop components A, B, C, D and E is by a specific method as described above, and refer to the description of the embodiments described below as necessary. Thus, each component can be easily obtained.

  As described above, the fragrance imparting agent according to the present invention has a natural herbal-like hop fragrance, and by adding this fragrance imparting agent to a desired pre-beverage liquid, the natural herbal-like hop fragrance is added to the beverage. Can be granted. In order to make a natural herbal-like hop fragrance feel more clearly in a beverage, each indicator component of the fragrance has a concentration shown in Table 2 to be described later in the beverage added with the fragrance imparting agent. It is desirable. In the case where the fragrance imparting agent includes, for example, two types of components of the G1 group, the concentration conditions in Table 2 may be satisfied for the two types included. Therefore, the fragrance imparting agent according to the present invention preferably contains each component in a ratio such that each indicator component of the fragrance shows the concentration shown in Table 2 in the beverage when it is added.

  According to a more preferred embodiment of the present invention, the fragrance imparting agent according to the present invention contains each component at a ratio based on the concentration shown in Table 2 described later.

  The fragrance imparting agent according to the present invention can be produced by using two or more selected from the G1 group and components of the G2 group, for example, by mixing them. In that case, it can adjust so that the component to be used may be preferably included in the ratio based on the density | concentration shown by Table 2 mentioned later.

  The aroma imparting agent according to the present invention can be produced by individually obtaining individual components without undergoing a step of contacting with yeast. In this case, the acquisition source of these aromatic components is not particularly limited, and any commercially available product, one obtained by synthesis, or one isolated and purified from a natural product may be used.

  The fragrance imparting agent according to the present invention is preferably obtained by adding hops to a medium containing sugar and a nitrogen source and bringing them into contact with yeast. As the sugar that can be used in the medium, liquid sugar, starch, etc. can be used. As the nitrogen source, protein degradation products, dried yeast extract, pea protein, soybean protein, etc. can be used. is there.

  Here, “contact with yeast” may be any state in which the hop aroma component is converted by yeast, and may be in a state where yeast is fermented or not fermented.

As hops used in the production of the fragrance imparting agent according to the present invention,
Comprising two or more components selected from G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol;
G2 consisting of 3-methyl-1-pentanol, hop component D, hop component E, 2-phenylethyl octoate, and methyl 2-methoxy-6-pentadecenoate after contact of the medium containing hops with yeast Those comprising precursors thereof which can give rise to a group of components. Such hops include, but are not limited to, health brooker species (country of origin: Germany).

  The addition amount of the fragrance imparting agent according to the present invention may vary depending on the production conditions and the like, but a typical example is 5% to 30% (volume%), preferably 10% to 20%.

  According to another preferred embodiment of the present invention, the fragrance imparting agent according to the present invention is obtained by adding hops to a medium containing a sugar and a nitrogen source and contacting with yeast. As long as it does not affect the herbal-like hop aroma that it has, it can be further processed in a form suitable for practical use, such as distillation, concentration, and emulsification, as necessary. It may be used as a fragrance imparting agent.

Beer-taste beverage The beverage according to the present invention comprises the fragrance imparting agent according to the present invention, and is provided with a natural herbal-like hop fragrance.
That is, the beverage according to the present invention is selected from the G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol so that the natural herbal-like hop aroma is clearly felt. A group of G2 consisting of two or more components selected from the group consisting of 3-methyl-1-pentanol, hop component D, hop component E, 2-phenylethyl octoate, and methyl 2-methoxy-6-pentadecenoate And an ingredient.

Preferably, in the beverage according to the present invention, the content (concentration) of the ingredients actually contained in the beverage satisfies the following conditions so that a natural herbal-like hop fragrance can be clearly felt. Is.
That is, when the target beverage is extracted by a C18 solid phase column and detected by gas chromatography / mass spectrometry (GC / MS), the concentration of β-eudesmol is 0.5 ppb to 7 ppb, and the sample The concentration of other components specified as the response ratio (%) of the quantitative ion to the ion 110 m / z of the internal standard substance borneol added so as to be 25 ppb in the middle satisfies the conditions in Table 2 below. When the ingredients contained in the beverage include, for example, two kinds of ingredients of the G1 group, the concentration conditions in Table 2 may be satisfied for the two kinds contained therein.

The concentration of each component shown in Table 2 can more preferably be as follows:
β-eudesmol is more preferably 1.0 ppb to 6.0 ppb, still more preferably 1.0 ppb to 4.0 ppb.
The hop component A is more preferably 1.0% to 8.0%, still more preferably 1.0% to 6.0%,
Hop component B is more preferably 0.5% to 5.0%, still more preferably 1.0% to 4.0%,
The hop component C is more preferably 1.0% to 10.0%, further preferably 3.0% to 6.0%,
Limonene oxide is more preferably 2% to 12%, still more preferably 3.0% to 8.0%,
3-methyl-1-pentanol is more preferably 2.0% to 13.0%, still more preferably 4.0% to 9.0%,
The hop component D is more preferably 0.5% to 6.0%, still more preferably 1.0% to 4.0%,
The hop component E is more preferably 2.0% to 16.0%, still more preferably 5.0% to 11.0%,
2-phenylethyl octoate is more preferably 8.0% -52.0%, still more preferably 17.0% -35.0%,
Methyl 2-methoxy-6-pentadecenoate is more preferably 11.0% to 69%, and further preferably 22.0% to 46.0%.

  More specifically, the beverage according to the present invention comprises the fragrance imparting agent according to the present invention and a beverage pre-beverage.

According to one preferable aspect of the present invention, the beverage according to the present invention comprises the fragrance imparting agent according to the present invention and a pre-solution of the beverage not containing the hop-derived component. The beverage thus obtained can be a beverage having a desired hop aroma in the present invention as a beverage while using a pre-beverage solution containing no hop-derived component. Here, the fragrance imparting agent is preferably obtained by adding hops to a medium containing sugar and a nitrogen source and bringing them into contact with yeast. In addition, the pre-beverage beverage containing no hop-derived component is obtained regardless of fermentation or non-fermentation, and does not contain hop itself or its components, or ferment wort containing hop. Refers to a pre-solution for beverage production that does not contain hop-derived components. Preferably, the pre-solution of the beverage not containing hop-derived components is obtained by fermenting a pre-fermentation solution without adding hops.
Therefore, in the production of beverages such as malt beverages and fermented malt beverages, those produced without the use of hops can be used as a suitable pre-beverage solution here.

  Moreover, according to another preferable aspect of this invention, the drink by this invention comprises the fragrance | flavor imparting agent by this invention, and the pre-solution of the drink containing a hop origin component. More specifically, the beverage according to the present invention may comprise the fragrance imparting agent according to the present invention and the beverage before obtained by fermenting the fluid before fermentation added with hops. . The beverage obtained in this manner is a beverage with a desired hop aroma enhanced and a hop aroma emphasized in the present invention, while using a pre-beverage beverage containing a hop-derived component. it can.

  In the present invention, the term “beverage” refers to a beer-taste beverage, a soft drink that does not necessarily have a beer taste, a carbonated beverage, a juice-containing beverage, a vegetable juice-containing beverage, a fruit juice and a vegetable juice-containing beverage, a fruit juice-containing beverage, a tea Beverages, milk, soy milk, milk beverages, drink-type yogurt, coffee, cocoa, nutritional drinks, sports drinks, and drinking water (mineral water, etc.) are also used. The beverage here is preferably a beer-taste beverage.

  In the present invention, “beer-taste beverage” refers to a beverage having a taste and aroma peculiar to beer obtained when beer is usually produced, that is, when beer is produced based on fermentation by yeast or the like. Examples include fermented malt beverages such as beer, happoshu, and liqueurs, and non-fermented malt beverages such as completely alcohol-free malt beverages.

  The beverage according to the invention can be provided in the form of a fermented beverage or a non-fermented beverage. In the present invention, “fermented beverage” means a beverage fermented with yeast. The “non-fermented beverage” means a beverage obtained without performing a fermentation process in the course of production.

  The beverage according to the present invention can be provided in the form of an alcohol-containing beverage containing alcohol. In the present invention, the “alcohol-containing beverage” includes, naturally, those containing alcohols produced in the fermentation process such as yeast or beverages obtained by separately adding alcohol, and fermentation obtained by fermentation with yeast. Used to include beverages and beverages with added alcohol. Moreover, the drink by this invention can also be provided with the form of the non-alcoholic drink which does not contain alcohol.

  The beverage according to the present invention can be provided in the form of a malt beverage. In the present invention, the “malt beverage” means a beverage mainly composed of wheat and / or wort obtained from malt, and includes a malt soft drink imparted with a refreshing feeling by carbon dioxide gas or the like. Examples of the malt beverage include non-fermented malt beverages such as a completely alcohol-free malt beverage having an alcohol content of 0% by weight, and alcohol-containing malt beverages containing alcohol. Examples of the alcohol-containing malt beverage include a fermented malt beverage obtained by fermentation and a malt beverage to which alcohol has been added. Examples of malt beverages include non-alcohol fermented malt beverages obtained by removing alcohol, other low-boiling components and low-molecular components from fermented malt beverages obtained by fermentation.

In the present invention, the “fermented malt beverage” means a beverage fermented by yeast using a carbon source, a nitrogen source, water and the like as raw materials, and using at least malt as a raw material.
Examples of such fermented malt beverages include beer, sparkling liquor, liqueur (for example, beverages classified as “liqueur (foaming) (1)” under the liquor tax law) and the like. The beverage according to the present invention can be preferably provided in the form of a fermented malt beverage containing the fragrance imparting agent according to the present invention and using at least water and malt as raw materials.

The beer-taste beverage according to the present invention is not particularly limited to a malt beverage as long as it is a beer taste, and can also be provided in the form of a non-wheat beverage that does not use wheat or malt. In the present invention, the “non-wheat beverage” includes a soft drink imparted with a refreshing feeling by carbon dioxide gas or the like. Non-wheat beverages include non-fermented beverages such as completely alcohol-free beverages having an alcohol content of 0% by weight, and alcohol-containing beverages containing alcohol. Examples of the alcohol-containing non-wheat beverage include fermented beverages obtained by fermentation and beverages to which alcohol is added.
Examples of non-wheat beverages include non-alcoholic fermented beverages obtained by removing alcohol, other low-boiling components and low-molecular components from fermented beverages obtained by fermentation.

Production of Beverage The beverage according to the present invention can be produced by adding the fragrance imparting agent according to the present invention to a beverage prior to the beverage (preferably a beverage prior to the beverage containing no hop-derived component). Specifically, the beverage of the present invention comprises two or more components selected from G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol, and 3-methyl- Manufactured by adding these to include G2-group components consisting of 1-pentanol, hop component D, hop component E, 2-phenylethyl octoate, and methyl 2-methoxy-6-pentadecenoate can do. Preferably, it can manufacture by adding each component contained so that it may become the predetermined | prescribed density | concentration shown by Table 2. For example, a beverage obtained without undergoing a fermentation process with yeast can be made into a beverage according to the present invention by adding the above-mentioned aroma components of G1 group and G2 group.

  According to one preferred embodiment of the present invention, the pre-beverage liquid used in the beverage according to the present invention is produced without using hops or hop-derived components as raw materials. When producing a beer-taste beverage, the pre-beverage solution can be prepared by fermenting, for example, malt, an auxiliary material (such as barley), and a fermentation stock solution using liquid sugar as a raw material without using hops. it can. Moreover, the beer-taste drink can also be used by adding the fragrance | flavor imparting agent by this invention to this using the thing prepared without passing through a fermentation process as a pre-liquid of a drink.

  When the beverage according to the present invention is a fermented malt beverage, for example, the pre-fermentation solution of the beverage can be produced by fermenting the pre-fermentation solution comprising at least water and malt without using hops. . In other words, fermenting beer yeast is added to wort (pre-fermentation liquid) prepared from brewing raw materials such as malt, which does not contain hops, and fermentation is performed. If desired, the fermentation liquid is stored at a low temperature, followed by a filtration step. By removing yeast, a pre-beverage solution that can be used for the fermented malt beverage according to the present invention can be produced.

  According to another preferred embodiment of the present invention, the pre-beverage liquid used in the beverage according to the present invention is produced using hops or hop-derived components as raw materials. In the case of producing a beer-taste beverage, for example, a pre-beverage solution can be prepared by fermenting a fermentation stock solution using hops, malt, auxiliary materials (such as barley) and liquid sugar as raw materials. Moreover, it can also be set as a beer-taste drink by using what was adjusted without passing through a fermentation process as a pre-liquid of a drink, and adding the fragrance | flavor imparting agent by this invention to this.

  In the above production procedure, wort can be produced according to a conventional method. For example, wort can be prepared by saccharifying a mixture of brewing raw materials and water, filtering to obtain wort, boiling the wort, and cooling the boiled wort. In the present invention, when hops may be added to the previous solution, typically, hops may be added at any stage.

  In the method for producing the pre-solution of the fermented malt beverage according to the present invention, in addition to malt, auxiliary materials specified by the liquor tax law such as rice, corn, corn, potato, starch, saccharides (for example, liquid sugar), protein degradation products, Other additives such as nitrogen sources such as yeast extract, fragrances, pigments, foaming / foaming improvers, water quality modifiers, and fermentation aids can be used as brewing materials. Further, ungerminated barley (for example, ungerminated barley (including an extracted one), ungerminated wheat (including an extracted one)) may be used as a brewing raw material. The obtained pre-fermented fermented malt beverage is either (i) distilled under reduced pressure or atmospheric pressure to remove alcohol and low-boiling components, or (ii) alcohol and low-molecular components are removed with a reverse osmosis (RO) membrane. By removing, it can also be set as the pre-solution of a non-alcohol fermented malt beverage.

  When the beverage according to the present invention is a beer-taste fermented beverage that does not use wheat or malt, the beverage is fermented with a pre-fermentation solution containing or not containing hops according to the procedure for producing the pre-solution of the fermented malt beverage. A pre-solution can be produced. For example, in addition to water, a carbon source (for example, sugars such as liquid sugar) and a nitrogen source (for example, amino acid sources such as protein degradation products and yeast extract) are added to the pre-fermentation solution without using hops. Other additives such as a fragrance, a pigment, a foaming / foam retention improver, a water quality modifier, a fermentation aid, and the like can be added as necessary. The pre-solution of the obtained beer-taste fermented beverage is either (i) distilled under reduced pressure or atmospheric pressure to remove alcohol and low-boiling components, or (ii) alcohol and low-molecular components in a reverse osmosis (RO) membrane. It can also be set as the pre-solution of a non-alcohol beer-taste fermented beverage.

  According to another aspect of the present invention, two or more components selected from G1 group consisting of hop component A, hop component B, hop component C, limonene oxide and β-eudesmol, and 3-methyl G2-group components consisting of -1-pentanol, hop component D, hop component E, 2-phenylethyl octoate, and methyl 2-methoxy-6-pentadecenoate have a predetermined concentration in the beverage A method for preparing a natural herbal-like hop-scented beverage is provided. The concentration of the fragrance component in the beverage may be adjusted by adding these fragrance components or selecting a variety of hops as a raw material.

  The present invention will be specifically described based on the following examples, but the present invention is not limited to these examples.

Experimental Method 1: Sample Preparation (1) Aromatizing Agent German health brooker species (available from Barth) were used as a hop variety. 15 g of hops were added to 1 L of a simple medium (sugar 7 ° P) containing sugar and nitrogen source, and heated at 80 ° C for 30 minutes. Here, brewer's yeast was added and allowed to stand for 4 days (96 hours) to prepare an additive solution as an aroma imparting agent.
(2) Happoshu liquor Happoshu (raw wort extract 12 ° P) made from malt, barley, and liquid sugar without using hops as a liquor liquor liquor for liquor samples for sensory evaluation Alcohol 5.5%).
Specifically, the happoshu pre-solution was prepared using a 1.5 L scale apparatus. Charged wort adjusted to 12 degrees was used in the brewing test (the ratio of malt used at the time of charging was 49%, the amount of auxiliary materials (barley, liquid sugar) used was 51%). More specifically, the charged wort was heated and boiled with an electric heater while adjusting the boiling strength to be constant and the evaporation rate to be 10% in 60 minutes. After boiling, the same amount of water as the amount of evaporation was added to the sample, and the wort was allowed to stand at 95 ° C. for 60 minutes. After filtering the filter paper, brewer's yeast was added to wort that had been cooled with ice water and subjected to main fermentation for 1 week and post-fermentation for 4 days.

Experimental Method 2: Method for Analyzing Aroma Component and Searching for Concentration of Indicator Component Gas chromatography with a mass spectrometer (GC / MS) was used for analyzing the aroma component and searching for the concentration of the indicator component of the aroma. Specifically, the fragrance component was extracted from the test sample with a C18 solid phase column and subjected to GC / MS. The internal standard method was used for quantification. Borneol was used as an internal standard substance, and added to 25 ppb in the sample. The analysis conditions of the hop aroma component in GC / MS were as follows.
In addition, the density | concentration of (beta) eudesmol was represented by ppb, and the density | concentration of each substance other than (beta) -eudesmol was quantified as response ratio (%) of each fixed_quantity | quantitative_ion with respect to ion 110m / z of internal standard substance borneol.

[GC / MS analysis conditions]
Capillary column: Product name: HP-INNOWAX (manufactured by Agilent, PEG column) (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm)
Oven temperature: 40 ° C., 0.3 min-3 ° C./min→240° C., 20 min Carrier gas: He, 10 psi low-pressure air supply Transfer line temperature: 240 ° C.
MS ion source temperature: 230 ° C
MSQ pole temperature: 150 ° C
Front inlet temperature: 200 ° C
Monitoring ion: Same as quantitative ion, ion used for quantitative determination:
Borneol (internal standard) m / z = 110
β-Udesmol m / z = 149
Others are as shown in Table B described later.

Test Example 1: Preparation of happoshu and evaluation test of fragrance (i) Test method 1 (additional liquid (fragrance imparting agent) prepared and adjusted in Test method 1 (1) was adjusted to 10% (volume%). The sample was added to the previous liquor prepared in 2) to obtain a happoshu sample. The resulting sparkling liquor sample has a spicy and cool herbal hop fragrance, and by adding the additive liquid to the pre-foam liquor, foaming with a desired natural herbal hop fragrance is imparted. It was confirmed that liquor could be prepared.

(Ii) Next, in the same manner, the additive liquid (fragrance imparting agent) prepared in Experimental Method 1 (1) was prepared in Experimental Method 1 (2) so that the addition concentration was in each condition described in Table A. The sample was added to the previous solution of happoshu to obtain each happoshu sample.
Sensory evaluation was performed about the obtained sample. The sensory evaluation was conducted by three trained panelists. The characteristics of the fragrance are as follows: “hop herbal incense” (natural herbal-like hop incense), “hop off-flavor” and “overall balance” (preference). As evaluated.

(Evaluation criteria for sensory tests)
“Hop herbal incense” was expressed as strength and evaluated according to the following criteria.
3: Has a good hop herbal incense and feels strong and clear 2: Has a hop herbal incense (feels)
1: Hop herbal incense is weak but feels 0: Does not feel

The “hop odor” was evaluated according to the following criteria.
3: Strong feeling of hop odor like "Aokusa", "matsukushi" and "oil" 2: Feeling hop odor like "Aokusa", "matsukusa" and "oil" 1: Feel a little hop odor 0: Feel Absent

The overall balance (preference) of the scent of the happoshu sample was evaluated according to the following criteria.
3: There is no hop odor, there is a hop herbal incense, and there is a good hop feeling as a whole 2: A good hop feeling as a whole is maintained 1: The hop feeling as a whole is maintained 0: Hop odor Is strong and the overall balance is not good

  The results were as shown in Table A.

As is clear from the results, a beverage (sample) having a firm hop herbal fragrance could be obtained at an addition ratio of the additive liquid (fragrance imparting agent) of 10% or more. The hop herbal incense became stronger as the additive ratio was increased. However, in the test plots with added concentrations of 30% and 40%, hop odors such as “green grass”, “pine oil” and “oil” came to be felt.
Therefore, it became clear that the suitable addition ratio of the additive liquid here is 5% to 30%, preferably 10% to 20%.

Test Example 2: Analysis of fragrance component and search for index component The fragrance component in the sample of Table A was exhaustively searched, and the substances considered to contribute to the characteristics of the hop herbal feeling were narrowed down.
Specifically, dozens of components were listed as candidates in the search process. The behaviors of these components were compared before and after hop addition and classified as follows.
Group G1: Components present in hops before addition of yeast Group G2: Components that are not detected as peaks before addition but are detected at least 24 hours after addition

Samples of these ingredients that have different aroma characteristics such as “fruit aroma” and “floral aroma” are prepared in the same manner, and the results are compared with the analysis results. Ingredients, that is, ingredients contributing to herbal incense were narrowed down.
Finally, it was judged that the fragrance components shown in Table B are highly likely to be suitable as the target fragrance index of the present invention.

  In addition, as a result of mass spectrometry, components (hop components A to E) that could not be identified based on known information such as literatures are analyzed on the analysis chart when analyzed under the analysis conditions of “Experiment Method 2”. Appearance time, that is, retention time, and each spectrum data (indicating the amount of response to the m / z value) are shown in Table B. These components were identified by these information.

In Table B, the spectral data includes three molecular weights of characteristic fragments in the detected molecular weight spectrum and some of their response amounts, in order of the fragments with the most responses, and these relationships are expressed with equal or inequality signs. did. At this time, the peak having a molecular weight of less than 50 was often affected by dichloromethane as a solvent, and it was difficult to find a characteristic peak.
Actual spectrum data were as shown in FIGS.

  In addition, the retention time (min) is shown as the number of minutes before and after the appearance time of the internal standard substance borneol (that is, ± number of minutes), and the difference in appearance time is also shown (value in parentheses in the retention time section of Table B). . For example, while the retention time of borneol is 42 minutes, the retention time of hop component A is 22 minutes, so the difference from the internal standard (difference in appearance time) was “−20 minutes”.

Test Example 3 Measurement of Concentration of Aroma Index Component The concentration of an index component related to a high-quality hop herbal fragrance in each sample of Table A was measured. The component concentration was calculated as ppb for β-eudesmol and the response ratio (%) of quantitative ions determined for each component with respect to 110 m / z of the internal standard substance borneol for other substances.

  The results were as shown in Table C.

From the results of Table A and Table C, it was considered that the preferable ranges of the respective aroma component values were as follows.
Component G1 group:
Hop component A: 0.5% to 10%
Hop component B: 0.1% to 7%
Hop component C: 0.5% to 12%
Limonene oxide: 1% to 14%
β-eudesmol: 0.5 ppb to 7 ppb
Component G2 group:
3-methyl-1-pentanol: 1% to 14%
Hop component D: 0.1% to 7%
Hop component E: 1% to 19%
Octanoic acid 2-phenylethyl ester: 4% to 62%
Methyl 2-methoxy-6-pentadecenoate: 6% to 82%

Moreover, it was thought that the more desirable range of each fragrance component value is as follows.
Ingredient G1 group:
Hop component A: 1.0% to 8.0%
Hop component B: 0.5% to 5.0%
Hop component C: 1.0% to 10.0%
Limonene oxide: 2% to 12%
β-eudesmol: 1 ppb to 6 ppb
Component G2 group:
3-methyl-1-pentanol: 2.0% to 13.0%
Hop component D: 0.5% to 6.0%
Hop component E: 2.0% to 16.0%
Octanoic acid 2-phenylethyl ester: 8.0% to 52.0%
Methyl 2-methoxy-6-pentadecenoate: 11.0% -69%

  On the other hand, in Test Example 1, since a high-quality fragrance was obtained for the first time after contact with yeast, in order to obtain the fragrance targeted by the present invention, two or more components selected from the components of the G1 group, and G2 All components of the group were considered necessary.

Claims (4)

A G1 group of components comprising hop component A, hop component B, hop component C, limonene oxide and β-eudesmol;
3-methyl-1-pentanol, hop component D, hop component E, Octanoic acid 2-phenylethyl ester, and methyl 2-methoxy-6-pentane An aromatizing agent having a natural herbal-like hop fragrance comprising a G2 group component consisting of Methyl 2-methoxy-6-pentadecenoate:
[here,
The hop components A, B, C, D and E are as follows with respect to the retention time of the internal standard substance borneol when measured by gas chromatography / mass spectrometry (GC / MS) under the following analysis conditions. In the spectral data indicating the response time with respect to the m / z value detected by the retention time, the m / z value is 50 or more and the response amount is large in order. Among the 15 peaks selected from the above, at least the following m / z value peaks are included:

[GC / MS analysis conditions]
Capillary column: HP-INNOWAX (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm)
Oven temperature: 40 ° C., 0.3 min-3 ° C./min→240° C., 20 min Carrier gas: He, 10 psi Air transfer Line temperature: 240 ° C.
MS ion source temperature: 230 ° C
MSQ pole temperature: 150 ° C
Front inlet temperature: 200 ° C. A G1 group of components comprising hop component A, hop component B, hop component C, limonene oxide and β-eudesmol;
3-methyl-1-pentanol, hop component D, hop component E, Octanoic acid 2-phenylethyl ester, and methyl 2-methoxy-6-pentane It is obtained by adding HealthBrucker seed hops to a medium containing sugar and nitrogen source, and contacting with yeast, comprising G2 group constituents consisting of Methyl 2-methoxy-6-pentadecenoate An aromatizing agent with natural herbal-like hop incense:
[here,
The hop components A, B, C, D and E are as follows with respect to the retention time of the internal standard substance borneol when measured by gas chromatography / mass spectrometry (GC / MS) under the following analysis conditions. In the spectral data indicating the response time with respect to the m / z value detected by the retention time, the m / z value is 50 or more and the response amount is large in order. Among the 15 peaks selected from the above, at least the following m / z value peaks are included:

[GC / MS analysis conditions]
Capillary column: HP-INNOWAX (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm)
Oven temperature: 40 ° C., 0.3 min-3 ° C./min→240° C., 20 min Carrier gas: He, 10 psi Air transfer Line temperature: 240 ° C.
MS ion source temperature: 230 ° C
MSQ pole temperature: 150 ° C
Front inlet temperature: 200 ° C. The health brewer seed hop is added to a medium containing sugar and a nitrogen source, and contacted with yeast to obtain the fragrance imparting agent according to claim 1 or 2,
The manufacturing method of the drink by which the natural herbal-like hop fragrance | flavor was provided including adding the obtained aroma imparting agent to the pre-solution of a drink.   The production method according to claim 3, wherein the beverage pre-solution does not contain a hop-derived component.

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