JP7753602B2 - Hop oxidation reaction product polyol aqueous solution - Google Patents

Description

The present invention relates to an aqueous polyol solution of a hop oxidation reaction product, in which an aqueous extract of a hop oxidation reaction product is dissolved in a polyol and water.

Hops (Humulus lupulus) are one of the main ingredients in beer and are involved in the bitterness, aroma, shelf life, etc. of beer. Hops have also been used as a folk medicine since ancient times and are known to have effects such as sedative, diuretic, anti-hair loss, and anti-allergic properties. Hops contain a variety of components that contribute to these effects.
The functional effects derived from hop-containing components are being studied and utilized in the fields of medicine, food, cosmetics, etc. For example, Patent Document 1 (JP 2003-183171 A) proposes a composition for treating sleep disorders containing hops, Patent Document 2 (JP 2003-238383 A) proposes a skin formulation containing hops, and Patent Document 3 (JP 2016-147917 A) proposes an autonomic nervous system regulator containing hops.

Hops have an extremely strong bitter taste, making them difficult to use as is in oral medications or foods. Patent Document 4 (Japanese Patent No. 5980687) and Non-Patent Document 1 report that, as a way to reduce this bitterness, hops are oxidized (aged) to convert the bitter acids that make up hops' bitter components, such as iso-α acids, α acids, and β acids, into oxidized matured hop bitter acids (MHBA), and that these hop oxidation reaction products, including matured hop bitter acids, have reduced bitterness and possess health functionality, such as an effect of improving lipid metabolism.

Japanese Patent Application Laid-Open No. 2003-183171 Japanese Patent Application Laid-Open No. 2003-238383 Japanese Patent Application Laid-Open No. 2016-147917 Patent No. 5980687

Morimoto-Kobayashi, Y., Ohara, K., Ashigai, H. et al. Matured hop extract reduces body fat in healthy overweight humans: a randomized, double-blind, placebo-controlled parallel group study. Nutr J 15, 25 (2015).

By extracting the hop oxidation reaction product using an aqueous solvent, an aqueous extract of the hop oxidation reaction product containing various active ingredients can be obtained.
However, the present inventors have discovered for the first time a problem in this aqueous extract: components that were dissolved at high temperatures immediately after extraction precipitate and form a suspension when cooled to room temperature, and when this aqueous extract is redissolved in a solvent such as water, it is difficult to handle, particularly at high concentrations.
Another object of the present invention is to solve this problem and to provide an aqueous polyol solution of a hop oxidation reaction product that is less likely to produce precipitates and has excellent storage stability.

The main means for solving the problems of the present invention are as follows.
1. An aqueous extract of hop oxidation products is
An aqueous polyol solution containing one or more polyols selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate), and a hop oxidation reaction product dissolved in water.
2. The aqueous polyol solution of a hop oxidation reaction product according to 1., wherein the hop oxidation reaction product contains mature hop-derived bitter acid (MHBA).
3. The aqueous polyol solution of a hop oxidation reaction product according to 1. or 2., characterized in that it contains pentylene glycol as the polyol.
4. The aqueous polyol solution of a hop oxidation reaction product according to any one of 1. to 3., characterized in that it contains 8% by mass or more and 22% by mass or less of pentylene glycol.
5. The aqueous polyol solution of a hop oxidation reaction product according to any one of 1. to 4., wherein the content of matured hop-derived bitter acids (MHBA) is 0.01% by mass or more and 3.0% by mass or less.
6. An aqueous extract of hop oxidation products is added.
A method for producing an aqueous polyol solution of a hop oxidation reaction product, comprising adding water and one or more polyols selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate).

The aqueous polyol solution of the hop oxidation reaction product of the present invention can dissolve a larger amount of components derived from the hop oxidation reaction product in a more stable manner than an aqueous solution containing only water as a solvent or a polyol solution containing only a polyol as a solvent. The aqueous polyol solution of the present invention is highly stable, is less likely to produce precipitates, and can be stored for a long period of time.
The aqueous polyol solution of the present invention is expected to have various higher effects due to the active ingredients that could not be fully utilized because it is a suspension containing solids.

Graph showing the height of precipitates in Example 2. Graph showing the height of precipitates in Example 3. Graph showing the height of precipitates in Example 4.

The present invention provides an aqueous extract of hop oxidation reaction products, comprising:
The present invention relates to an aqueous polyol solution containing one or more polyols selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate), and a hop oxidation reaction product dissolved in water.

Hop oxidation reaction product: A hop oxidation reaction product is a product obtained by oxidizing hops or processed hops (hop pellets, etc.). The hop oxidation reaction product of the present invention can be obtained by oxidizing hops by contacting them with oxygen in the air. The oxidation method of the present invention is not particularly limited, but it is preferable to heat hops in air.

The heating temperature in the oxidation treatment method of the present invention is not particularly limited, but a preferred upper limit is 100°C, and a more preferred upper limit is 80°C. Heating temperatures of 100°C or lower are advantageous in that oxidation proceeds preferentially over isomerization. The preferred lower limit for the heating temperature is 40°C, but oxidation can also be carried out at room temperature or at lower temperatures. A more preferred lower limit for the heating temperature is 60°C, and an especially preferred lower limit for the heating temperature is 65°C. Heating temperatures of 60°C or higher are advantageous in that the oxidation reaction proceeds efficiently. The reaction time is also not particularly limited and can be determined appropriately depending on the hop variety and reaction temperature. The oxidation treatment can be carried out, for example, at 60-80°C for 8-120 hours, with 48-120 hours at 60°C and 8-24 hours at 80°C being preferred. The form of the hops is not particularly limited as long as they can come into contact with oxygen in the air, but powdered form is preferred to shorten the reaction time. They may also be stored in a high-humidity environment.

In addition, in the present invention, hops (Humulus lupulus L.) may be in any form as long as they contain lupulin, including those harvested and yet to be dried, harvested and dried, compressed, crushed, or processed into pellets, but are preferably in the form of hop pellets. Hop pellets may be commercially available, such as hop cones compressed into pellets (Type 90 pellets), pellets with selectively concentrated lupulin (Type 45 pellets), or isomerized hop pellets (e.g., Isomerized Pellets (Hopsteiner)).

Hop varieties are not particularly limited, but examples include Galaxy, Saaz, Cascade, Hallertau Tradition, Bullion, Brewers Gold, Chinook, Cluster, East Kent Golding, Fuggles, Hallertau, Mount Hood, and Northern Brewer. Brewer, Perle, Styrian, Target, Tettnanger, Willamette, Hersbrucker, Bravo, Columbus, Herkules, Magnum, Millennium, Nugget, Summit, Tomahawk, Warrior, Zeus, Hallertau Examples include Bravo, Columbus, Hercules, Magnum, Millennium, Nugget, Summit, Tomahawk, Warrior, Zeus, etc., and from the perspective of a stable supply of raw materials, relatively inexpensive bitter varieties are preferable. Specific examples include Bravo, Columbus, Hercules, Magnum, Millennium, Nugget, Summit, Tomahawk, Warrior, Zeus, etc.

Hops contain bitter components derived from resins, such as alpha acids (humulones), beta acids (lupulones), and iso-alpha acids (isohumulones). In the present invention, "alpha acids (humulones)" is used to include humulone, adhumulone, cohumulone, posthumulone, and prehumulone. In addition, in the present invention, "beta acids (lupulones)" is used to include lupulone, adlupulone, colupulone, postlupulone, and prelupulone. Furthermore, in the present invention, "iso-α acids (isohumulones)" is used to include isohumulone, isoadhumulone, isocohumulone, isoposthumulone, isoprehumulone, Rho-isohumulone, Rho-isoadhumulone, Rho-isocohumulone, Rho-isoposthumulone, Rho-isoprehumulone, tetrahydroisohumulone, tetrahydroisoadhumulone, tetrahydroisocohumulone, tetrahydroisoprehumulone, tetrahydroisoposthumulone, hexahydroisohumulone, hexahydroisoadhumulone, hexahydroisocohumulone, hexahydroisoposthumulone, and hexahydroisoprehumulone. It should be noted that iso-α acids exist as cis and trans stereoisomers, and unless otherwise specified, the term includes both.

By subjecting hops or their processed products (such as hop pellets) to oxidation treatment, the content of alpha acids, beta acids, and iso-alpha acids is reduced, and a "hop oxidation reaction product" is obtained in which the content of other components is increased.
The hop oxidation reaction product of the present invention preferably contains a high level of matured hop bitter acids (MHBA), which are oxidation products of bitter components such as α acids, β acids, and iso-α acids. MHBA has a significantly lower bitterness than α acids, β acids, iso-α acids, and the like, and has health functional effects (Patent Document 4, Biosci. Biotech. Biochem. 2015; 79:1684-1694), making it advantageous for imparting health functions to the hop oxidation reaction product. Suitable examples of components constituting such MHBA include the compounds represented by the following formulas (1a-c) to (8a-c). Therefore, the hop oxidation reaction product of the present invention preferably contains at least one compound selected from the following formulas (1a-c) to (8a-c), and more preferably contains two or more or all of the compounds. MHBA can be quantified according to the method described in Test Example 1 of JP-A-2018-199639.

Hop oxidation reaction products preferably contain "tricyclooxyisohumulones." "Tricyclooxyisohumulones" include tricyclooxyisocohumulone A (TCOIcoH A: formula (5a), IUPAC name: (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2-(2-methylpropanoyl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione), tricyclooxyisohumulone A (TCOIcoH A: formula (5a), IUPAC name: (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2-(2-methylpropanoyl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione), A: Formula (5b), IUPAC name: (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2-(3 -methylbutyryl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione), tricyclooxyisoadhumulone A (tricyclooxyisoadhumulone A) (TCOIadH A: Formula (5c), IUPAC name: (3aS,5aS,7S,8aS)-3,3a-dihydroxy-7-(1-hydroxy-1-methylethyl)-6,6-dimethyl-2- (2-methylbutanoyl)-5a,6,7,8-tetrahydro-3aH,5H-cyclopenta[c]pentalene-1,4-dione).

The MHBA content in the hop oxidation reaction product of the present invention, based on the dry mass of the entire hop oxidation reaction product, can be suitably set at a lower limit of 0.1%, 0.5%, or 1% by mass, and at a higher limit of 15%, 20%, 30%, 50%, 70%, 90%, 96%, or 98% by mass. The MHBA content in the hop oxidation reaction product of the present invention can be, for example, 0.1 to 98% by mass, more preferably 0.1 to 90% by mass, even more preferably 0.1 to 70% by mass, even more preferably 0.1 to 30% by mass, and even more preferably 1 to 20% by mass.

Furthermore, in the hop oxidation reaction product of the present invention, the content of α acids, β acids, and iso-α acids is reduced by subjecting the hops to an oxidation treatment. The range of the bitter component content of the hop oxidation reaction product of the present invention, when converted into the total content of α acids, β acids, and iso-α acids relative to the dry mass of the entire hops, can have a preferred lower limit of 0.01%, 0.02%, 0.05%, or 0.1% by mass, and a preferred upper limit of 0.5%, 1%, 5%, or 10% by mass. The range of the bitter component content of the hop oxidation reaction product of the present invention, as converted into the total content of α acids, β acids, and iso-α acids, is, for example, 0.01 to 5% by mass, preferably 0.05 to 5% by mass, and more preferably 0.1 to 1% by mass. The content of such bitter components can be determined by converting it into the total content of α acids, β acids, and iso-α acids according to, for example, the method described in Test Example 1 of JP 2018-199639 A.

Furthermore, from the perspective of achieving both reduced bitterness and imparting health benefits, the content of MHBA in the hop oxidation reaction product is preferably equal to or greater than the bitter components (total amount of alpha acids, beta acids, and iso-alpha acids), more preferably four times or greater, even more preferably 50 times or greater, even more preferably 90 times or greater, and even more preferably 100 times or greater.

Aqueous Extract of Hop Oxidation Reaction Product The aqueous extract of the hop oxidation reaction product of the present invention is an extract obtained by subjecting the above-described hop oxidation reaction product to extraction with an aqueous solvent. Examples of the aqueous solvent include water, water-miscible lower alcohols such as methanol and ethanol, glycols such as ethylene glycol, acetone, acetic acid, and polar solvents such as mixtures thereof. The extraction method is not particularly limited, and for example, the method described in Non-Patent Document 1 (Nutr J. 2016;15:25.) can be used. Aqueous extraction can reduce the bitterness of the hop oxidation reaction product. The extraction temperature is not particularly limited, but is preferably 60°C or lower, and more preferably 50 to 60°C in consideration of extraction efficiency.

In the present invention, the aqueous extract of hop oxidation reaction products can be used as a dried solid, a concentrated liquid, or an aqueous extract as is. However, from the viewpoint of ease of handling, it is preferable to use water as the extract and use the aqueous extract as is. In addition to the drying or concentration described above, heat sterilization treatment, etc., can also be performed. Specifically, boiling, degassing under reduced pressure, concentration under reduced pressure, spray drying, freeze drying, high-temperature short-time heat treatment, high-temperature short-time sterilization, or a combination thereof can also be used.
The aqueous extract of a hop oxidation reaction product is a transparent solution at high temperatures immediately after extraction, but typically takes the form of a suspension when cooled to low temperatures, due to the precipitation of dissolved components. In the present invention, the aqueous extract of a hop oxidation reaction product may remain in the form of a suspension, or may be subjected to filtration, treatment with an adsorbent such as activated carbon or polyvinylpolypyrrolidone (PVPP), a filter aid, a clarifier, or a suspending agent, as necessary. However, since the aqueous polyol solution of the present invention is capable of dissolving much of the insoluble matter in the aqueous extract of a hop oxidation reaction product, it is preferable to use the aqueous extract as a suspension in order to utilize the active ingredients contained in the insoluble matter.

The content of the aqueous extract of hop oxidation reaction products in the aqueous extract of hop oxidation reaction products is 1 to 30% by mass, and the content of MHBA is preferably 0.1 to 10% by mass, more preferably 0.5 to 8% by mass, and particularly preferably 1 to 5% by mass, from the perspective of functional effects. Furthermore, the Brix value of the aqueous extract of hop oxidation reaction products is preferably 5 to 30°Bx, more preferably 10 to 20°Bx, from the perspective of ease of handling.

Polyols The polyol can be one or more selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate), and two or more can be mixed and used as long as the effects of the present invention are not impaired. Of these, pentylene glycol is preferred due to its solubility in solids, ease of handling, and minimal change in odor. Furthermore, aqueous solvents other than the above-mentioned polyols can also be included as long as the effects of the present invention are not impaired.

When pentylene glycol is used as the polyol in the aqueous polyol solution of the present invention, the amount of pentylene glycol is preferably 8% by mass or more and 22% by mass or less, and more preferably 8% by mass or more and 20% by mass or less. When the amount of pentylene glycol is within this range, the solubility is excellent, the amount of insoluble matter can be reduced, and in some cases, complete dissolution can be achieved.

In the aqueous polyol solution of the present invention, the ratio of the aqueous extract of the hop oxidation reaction product to the polyol is not particularly limited as long as it does not interfere with the effects of the present invention. However, when the amount of the aqueous extract of the hop oxidation reaction product is 30% by mass or less, the ratio of the amount of the polyol to the amount of the aqueous extract of the hop oxidation reaction product is preferably 0.1 to 4.5, more preferably 0.2 to 4.0, and even more preferably 0.3 to 3.8.

Water In the aqueous polyol solution of the present invention, the ratio of polyol to water is not particularly limited as long as it does not impede the effects of the present invention. However, the weight ratio of polyol to water (polyol:water) is preferably within the range of 5:95 to 40:60, more preferably within the range of 10:90 to 30:70, and even more preferably within the range of 10:90 to 25:75.

Aqueous Polyol Solution The aqueous polyol solution of the hop oxidation reaction product of the present invention contains both polyol and water as solvents. The insoluble components of the aqueous extract (which may be a suspension) of the hop oxidation reaction product are not completely soluble in either polyol or water alone. By adding polyol and water to the aqueous extract (which may be a suspension) of the hop oxidation reaction product and heating as necessary, it is possible to dissolve and reduce much of the insoluble components in water at room temperature, and in some cases even completely dissolve them. The heating temperature is not particularly limited as long as it is below the boiling point of the aqueous polyol solution used, but is preferably below 100°C. To improve solubility, it is preferable to add the polyol and then the water. Furthermore, to improve solubility, it is preferable to heat the mixture after adding the polyol and water.

In the aqueous polyol solution of the present invention, the concentration of the aqueous extract of the hop oxidation reaction product is preferably 3% by mass or less. If the concentration of the aqueous extract of the hop oxidation reaction product exceeds 3% by mass, insoluble matter is likely to remain, and storage stability may decrease, making precipitation more likely to occur over time. The concentration of the aqueous extract of the hop oxidation reaction product is more preferably 2% by mass or less, and even more preferably 1.5% by mass or less. The lower limit of the concentration of the aqueous extract of the hop oxidation reaction product is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and even more preferably 0.5% by mass or more.

In the aqueous polyol solution of the present invention, from the viewpoint of functionality, the content of MHBA is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.1% by mass or more, and is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and even more preferably 0.5% by mass or less.

The aqueous polyol solution of the present invention may or may not contain insoluble matter. Insoluble matter in the aqueous polyol solution can be removed by filtration or centrifugation. By removing insoluble matter that acts as agglomeration nuclei, the aqueous polyol solution of the present invention can be made less susceptible to precipitation over time, improving storage stability. If the aqueous polyol solution of the present invention contains insoluble matter, the proportion of insoluble matter is preferably 0.3% by mass or less, more preferably 0.2% by mass or less, and even more preferably 0.15% by mass or less, based on the aqueous polyol solution.

The aqueous polyol solution of the present invention may contain other components as long as the aqueous extract of hop oxidation reaction products is dissolved in a specific polyol and water. Examples of other components that may be contained in the aqueous polyol solution of the present invention include surfactants, thickeners, flavorings, pH adjusters, etc.

The present invention will be described in detail below based on examples, but the present invention is not limited to these examples.
Aqueous extract of hop oxidation reaction products Matured hop extract (Kirin Holdings Co., Ltd., solid content 11% by mass, MHBA 2.65% by mass)

・Polyol

"Example 1"
1 g of matured hop extract and 2 g of polyol were weighed into a 15 mL centrifuge tube (Sumitomo Bakelite Co., Ltd.) and dissolved by stirring. 7 g of purified water was added to the mixture to make a total of 10 g, and the mixture was mixed and dissolved to obtain an aqueous polyol solution with a concentration (% by mass) of an aqueous extract of hop oxidation products of approximately 1%. A similar procedure was also performed, except that purified water was used instead of the polyol, to obtain an approximately 1% aqueous solution.
The transparency immediately after preparation and the height of the precipitate after standing for 4 days were measured, and the stability was evaluated according to the following criteria. The results are shown in Table 2.
Unless otherwise specified in the examples, all operations such as preparation of aqueous polyol solutions and stability evaluation were carried out at room temperature.

Transparency: Good: No visible precipitates, transparent.
×: Precipitates are visible and suspended.
Stability: Good: The height of the precipitates is 2.0 mm or less.
Δ: The height of the precipitate exceeds 2.0 mm and is 3.0 mm or less.
×: The height of the precipitate exceeds 3.0 mm.
Overall evaluation: Clearness of supernatant and stability are both good.
△: Supernatant transparency is ◯, stability is △.
×: Either one or more of the supernatant transparency and stability was ×.

Pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, and cyclohexylglycerin did not dissolve after adding 20% polyol, and the suspension appeared fluffy and swollen, but when water was added to make an approximately 1% polyol aqueous solution, the suspension dissolved to some extent and decreased in size. Of these, pentylene glycol and cyclohexylglycerin in particular produced little precipitate and were excellent in stability.
The mixture of polyglyceryl-10 (eicosanedioic acid/tetradecanedioic acid) and glycerin was dissolved and transparent both after the addition of polyol alone and after the addition of water. There was also little precipitate, and the mixture was excellent in stability.
Glycerin and diglycerin were soluble in polyol solutions to some extent, but when water was added to make an approximately 1% aqueous polyol solution, precipitates formed and became suspended.
The other polyols were poorly soluble in both the polyol and the aqueous polyol solution.

"Example 2"
The samples shown in Table 3 below were weighed out into 15 mL centrifuge tubes so that the total amount was 10 g, and the samples were dissolved by stirring at room temperature. Immediately after preparation, the aqueous polyol solutions were all transparent, and no precipitate was visible. After leaving the solution for one week, the height of the precipitated solids was measured. The results are shown in Figure 1.

It was confirmed that when the pentylene glycol was 20% by mass, the amount of precipitate was significantly reduced when the matured hop extract was 30% by mass or less.

"Example 3"
Among Nos. 1 to 5, No. 3, which contained a high concentration of matured hop extract, was used as the center concentration for examining the concentration of pentylene glycol. The samples shown in Table 4 below were weighed out to a total weight of 10 g in a 15 mL centrifuge tube and dissolved by stirring at room temperature. The height of the precipitate was measured after standing for four days. The results are shown in Figure 2.

Particularly large amounts of precipitates were formed when the pentylene glycol content was 5% by mass and 25% by mass. The height of the precipitates was 6 mm or less when the content was 8% by mass to 22% by mass, and the amount of precipitates was particularly small when the content was 8% by mass to 20% by mass. This suggests that stability is not improved with increasing polyol content, but is excellent within an appropriate range. The aqueous solution No. 20, which does not contain pentylene glycol, had a clearly suspended supernatant compared to the aqueous polyol solutions Nos. 11 to 19.

"Example 4"
A total of 10 g of the No. 5 formulation was weighed into a 15 mL centrifuge tube and dissolved by stirring at room temperature.
In addition, a similar mixture of matured hop extract and pentylene glycol was added, heated at 90°C for 1 hour, and then purified water was added. Another mixture was added in its entirety and then heated at 90°C for 1 hour. Both aqueous polyol solutions were transparent immediately after preparation, with no visible precipitates.
After leaving the mixture at room temperature for one week, the height of the precipitated solid was measured, and the results are shown in FIG.

It was confirmed that the amount of precipitates was significantly reduced by heating after adding polyol and water.
When the solution was heated with only the polyol added, a large amount of precipitates were formed upon heating, and the precipitates did not dissolve even when water was further added, resulting in a larger amount of precipitates than when the solution was dissolved at room temperature. Therefore, it was confirmed that when heating is performed during the production of the aqueous polyol solution of the present invention, it is preferable to heat after all the polyol has been added.

Claims (4)

An aqueous extract of hop oxidation products,
an aqueous polyol solution containing one or more polyols selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate), and a hop oxidation reaction product dissolved in water ;
a concentration of the aqueous extract of hop oxidation reaction products of 0.1% by mass or more and 3% by mass or less;
The weight ratio of polyol to water is 5:95 to 40:60,
An aqueous polyol solution of a hop oxidation reaction product, comprising 8% by mass or more and 22% by mass or less of pentylene glycol . The aqueous polyol solution of a hop oxidation reaction product according to claim 1, characterized in that the hop oxidation reaction product contains mature hop-derived bitter acid (MHBA). 3. The aqueous polyol solution of hop oxidation reaction products according to claim 1 , wherein the content of matured hop-derived bitter acids (MHBA) is 0.01% by mass or more and 3.0% by mass or less. An aqueous extract of hop oxidation products,
adding water and one or more polyols selected from the group consisting of pentylene glycol, 1,3-butylene glycol, dipropylene glycol, methyl gluceth-10, cyclohexylglycerin, and polyglyceryl-10 (eicosanedioate/tetradecanedioate);
a concentration of the aqueous extract of hop oxidation reaction products of 0.1% by mass or more and 3% by mass or less;
The weight ratio of polyol to water is 5:95 to 40:60,
A method for producing an aqueous polyol solution of a hop oxidation reaction product, the aqueous solution containing 8% by mass or more and 22% by mass or less of pentylene glycol .