JP2018161108A - Method for producing fatty ester-containing hop composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a hop-derived product capable of effectively imparting a fruit-like aroma to foods and drinks. A method for producing a fatty acid ester-containing hop composition, which comprises a step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with a hop, is used. [Selection diagram] None

Description

  The present invention relates to a method for producing a fatty acid ester-containing hop composition.

  Hops are an important ingredient in beer-taste beverages and contain a variety of ingredients. Among them, the resin component imparts a bitter taste to a beer-taste beverage, and the essential oil component imparts a fragrance. The composition of these ingredients varies depending on the variety of hops, and in recent years, aroma varieties having a fruit-like aroma have attracted attention in order to increase the taste of beverages, and new flavor-type beverages have been developed. However, the essential oil component has a larger compositional variation than the resin component, and there are cases where restrictions such as a rise in the price of rare varieties may occur, and it is often difficult to stably supply a raw material of a certain quality. In addition, even if hops are used for aroma imparting purposes, resin-derived alpha acids, beta acids and iso alpha acids are added at the same time, so the use of hops is restricted to maintain a balance between aroma and bitterness. May occur.

  On the other hand, the fruity and gorgeous fragrance peculiar to effervescent alcoholic beverages such as beer can also be imparted by esters. Examples of the esters include ethyl isobutyrate, ethyl isovalerate, and ethyl 2-methylbutyrate. These esters are produced from hop-derived fatty acids during yeast fermentation, but their production is limited (Non-Patent Document 1). In Patent Document 1, a citrus and gorgeous ester is obtained by extracting hops with ethanol, esterifying short-chain fatty acids contained in the extract using an acid catalyst, and adding the extract after the wort boiling step. A method for producing a sparkling alcoholic beverage having a scent is disclosed. However, in this method, ethanol and acid catalyst used for extraction remain in the final product, and bitterness components such as α acid, β acid, and iso α acid contained in the ethanol extract are simultaneously added. In some cases, restrictions may be imposed on applicable beverages and added amounts.

JP 2008-263838 A

J. Brew. Soc. Japan. Vol. 104, No. 3, p157-169, 2009

  This invention makes it the subject to provide the hop origin product which can provide fruit-like aroma effectively to food-drinks including a drink. Furthermore, this invention makes it a subject to reduce the bitterness derived from a hop in the hop origin product which has the above fruit-like aromas.

  The present inventors have now found that, when alcohol is used as an entrainer and hops are extracted with supercritical carbon dioxide, fatty acids in the hop composition corresponding to the extraction residue can be efficiently converted into fatty acid esters. Furthermore, the present inventors have found that the content of the bitter component in the hop composition can be effectively reduced in the supercritical extraction process using the alcohol together. The present invention is based on these findings.

According to the present invention, the following is provided.
(1) A method for producing a fatty acid ester-containing hop composition comprising a step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with a hop.
(2) The method according to (1), wherein the content of the fatty acid ester in the hop composition is 1 × 10 ⁻⁴ mass% or more.
(3) The production method according to (1) or (2), wherein the total content of α-acid and iso-α-acid in the hop composition is 2% by mass or less.
(4) The production according to any one of (1) to (3), wherein the content of the aged hop bitter acid (MHBA) in the hop composition is equal to or greater than the total content of α acid and iso α acid. Method.
(5) The production method according to any one of (1) to (4), wherein the alcohol is ethanol.
(6) The production method according to any one of (1) to (5), wherein the fatty acid ester is at least one selected from ethyl isobutyrate, ethyl isovalerate, and ethyl 2-methylbutyrate.
(7) Fatty acid ester containing hop composition whose content of fatty acid ester is 1 × 10 ⁻⁴ mass% or more.
(8) The hop composition according to (7), wherein the total content of α acid and iso α acid is 2% by mass or less.
(9) The hop composition according to (7) or (8), which is obtained by the method according to any one of (1) to (6).
(10) A hop-derived food or drink that uses or contains the hop composition according to any one of (7) to (9).
(11) The food or drink according to (10), which is a beverage.
(12) A method for imparting a fatty acid ester to a hop, comprising a step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with the hop.

  According to the present invention, it is possible to provide a hop composition containing a fatty acid ester at a high level using a mixed fluid containing supercritical carbon dioxide and alcohol. Moreover, since this invention does not perform yeast fermentation and uses a supercritical fluid process, it is advantageous when providing a fatty acid ester to a hop in a short time. Moreover, according to this invention, content of the bitterness component in a hop can be reduced. Further, according to the present invention, since the supercritical extraction treatment is used without using an additive such as a catalyst, it is possible to effectively prevent subcomponents such as alcohol and catalyst from remaining in the hop composition. Can be suppressed. Furthermore, according to the present invention, a hop composition having a fruit-like aroma can be efficiently provided from an inexpensive bitter variety without using a rare aroma variety, which is particularly advantageous in industrial production.

The manufacturing method of the fatty acid ester containing hop composition The manufacturing method of the fatty acid ester containing hop composition of this invention comprises the process which the mixed fluid containing a supercritical carbon dioxide and alcohol and a hop are made to contact.

Preparation of hops In the present invention, hops (Humulus lupulus L.) may be in any form as long as it contains a lupulin part, before harvesting and drying, harvested and dried, compressed A pulverized product, a pulverized product, or a pulverized product may be used, but a hop pellet is preferable. Commercially available hop pellets may be used, for example, hop spikelets compressed into pellets (Type 90 pellets), pellets with selectively enriched lupurin (Type 45 pellets), or isomerization treatment Hop pellets (for example, Isomerized Pellets (Hopsteiner)) and the like.

  The variety of hops is not particularly limited. For example, Galaxy, Saaz, Cascade, Halertau Tradition, Bullion, Brewers Gold ), Chinook, Cluster, East Kent Golding, Fuggles, Hallertau, Mount Hood, Northern Brewer, Perle , Styrian, Target, Tettnanger, Willamette, Healthbrucker, Bravo, Columbus, Herkules, Magnum, Millennium ( Millennium, Nugget, Summit t), Tomahawk, Warrior, Zeus and the like, and from the viewpoint of stable supply of raw materials, it is preferable to be a relatively inexpensive bitter variety, and as a specific example, Bravo, Columbus, Herkules, Magnum, Millennium, Nugget, Summit, Tomahawk, Warrior, Zeus, etc. Is mentioned.

  In addition, as the hop of the present invention, a fresh hop may be used as it is, or a hop that has undergone oxidation may be used. From the viewpoint of increasing the content of fatty acid corresponding to the fatty acid ester precursor, an oxidized hop is used. It is preferable to use it. Therefore, according to a preferred embodiment, the production method of the present invention comprises a step of oxidizing hops. Oxidized hops can be produced by contacting the hops with oxygen in the air. In order to promote oxidation, it is preferable to heat the hop in air. Although heating temperature is not specifically limited, A preferable upper limit is 100 degreeC and a more preferable upper limit is 80 degreeC. When the heating temperature is set to 100 ° C. or lower, it is advantageous in promoting oxidation preferentially over isomerization. Moreover, although the minimum of preferable heating temperature is 40 degreeC, you may oxidize at room temperature and low temperature. Further, the reaction period is not particularly limited, and can be appropriately determined depending on the type of hop and the reaction temperature. For example, it is preferably 48 to 120 hours at 60 ° C and 8 to 24 hours at 80 ° C. The form of the hop when it is subjected to the oxidation reaction is not particularly limited as long as it can come into contact with oxygen in the air, but it is preferably in a powder form.

  Hops contain resin-derived bitter components such as α acids (humulones), β acids (luprons), and iso α acids (isohumulones). In the present invention, “α acid (humulones)” is used in the meaning including humulone, adhumulone, cohumulone, posthumulone, and prehumulone. Further, in the present invention, “β acid (Luprons)” is used in the meaning including lupron, adolpron, colpron, postlupron and prelupron. Furthermore, in the present invention, “isoα acid (isohumulones)” is isohumulone, isoadhumulone, isocohumulone, isoposthumulone, isoprehumulone, Rho-isohumulone, Rho-isoadhumulone, Rho-isocohumulone, Rho-isoposthumulone, Rho- Isoprehumulone, Tetrahydroisohumulone, Tetrahydroisoadhumulone, Tetrahydroisocohumulone, Tetrahydroisoprehumulone, Tetrahydroisoposthumulone, Hexahydroisohumulone, Hexahydroisoadhumulone, Hexahydroisocohumulone, Hexa It is used in the meaning including hydroisoposthumulone and hexahydroisoprehumulone. In addition, iso α acid has cis and trans stereoisomers, and unless otherwise specified, it is used to include both.

  The content of the bitter component in the hop is not particularly limited and can be adjusted depending on the presence or absence of oxidation, conditions, etc. The preferred lower limit can be 0.05% by weight, 0.1% by weight, 1% by weight, 5% by weight, or 10% by weight, and the preferred upper limit is 0.5% by weight, 1% by weight. It can be 5 mass%, 10 mass%, 15 mass%, or 20 mass%. In the case of hops that are not subjected to oxidation, the content range of the bitter component is preferably 1 to 20% by mass, more preferably 5 to 20% by mass, as the converted value. Moreover, in the case of an oxidation hop, the range of content of a bitterness component is 0.05-5 mass% preferably as said conversion value, More preferably, it is 0.1-1 mass%. The content of the bitter component can be determined by converting to the total content of α acid and iso α acid according to the method described in Test Example 2 described later.

  Moreover, the fatty acid used as the raw material of fatty acid ester is contained suitably in the hop. Such fatty acid is preferably isobutyric acid, isovaleric acid, 2-methylbutyric acid or a combination thereof, and more preferably a combination of isobutyric acid, isovaleric acid and 2-methylbutyric acid.

  The content of fatty acid in hops can be appropriately adjusted depending on the hop oxidation conditions and the like. The upper limit may be 0.1% by weight, 0.5% by weight, 1% by weight, or 2% by weight. In the case of hops that are not subjected to oxidation, the range of the fatty acid content is preferably 0.001 to 0.05% by mass, more preferably 0.005 to 0.02% by mass, as the converted value. It is. In the case of oxidized hops, the range of the fatty acid content is preferably 0.01 to 2% by mass, more preferably 0.05 to 0.2% by mass, as the converted value. The content of the fatty acid can be determined based on the total amount of isobutyric acid, isovaleric acid and 2-methylbutyric acid according to the method described in Test Example 2 described later.

Step of contacting supercritical fluid and hop In the production method of the present invention, the raw material hop as described above is brought into contact with a mixed fluid containing supercritical carbon dioxide and alcohol. As long as the effect of the present invention is not hindered, such a contacting step can be carried out according to a known supercritical extraction method using a combination of supercritical carbon dioxide and alcohol as an entrainer (another solvent).

  The mixed fluid in the present invention is obtained by adding alcohol as an entrainer to carbon dioxide (supercritical carbon dioxide) under conditions of a critical temperature or higher and a critical pressure or higher.

  The temperature and pressure in the mixed fluid are about 31 ° C. to 100 ° C., the pressure is about 7.4 MPa to 100 MPa, preferably the temperature is about 31 ° C. to 50 ° C., considering the critical temperature and critical pressure of carbon dioxide. The pressure is about 7.4 MPa to 40 MPa.

  Examples of the alcohol in the present invention include methanol, ethanol, propanol, butanol and the like, and ethanol is preferably used from the viewpoint of food use.

  The concentration of alcohol in the mixed fluid is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass.

  The supercritical carbon dioxide used in combination with alcohol can be brought into contact with 1 g of raw material hops at a flow rate of, for example, 0.25 to 1.25 g / min, preferably 0.375 to 0.625 g / min. . Such contact time may be, for example, about 1 minute to 30 hours, preferably about 10 minutes to 5 hours.

  The contact step can be performed using a known supercritical extraction apparatus. Such a supercritical extraction apparatus can be configured by connecting a high-pressure pump, a pressure vessel, and a separator with a gas line. In the case of using a supercritical extraction apparatus, first, hops are sealed in a pressure vessel, and then carbon dioxide is fed by a high-pressure pump and pressurized. At the same time, the pressure vessel is heated and maintained at a predetermined pressure and temperature. After holding for a certain period of time, carbon dioxide is released from the pressure vessel through a separator while maintaining the pressure and temperature of the system. And in a separator, an extract and a carbon dioxide are isolate | separated and the hop composition can be obtained as an extraction residue in this case.

Fatty acid ester-containing hop composition According to the production method of the present invention, a hop composition containing a fatty acid ester having a fruit-like aroma at a high level can be provided through the contact step.

The content of the fatty acid ester in the hop composition of the present invention is preferably 1 × 10 ⁻⁴ mass% or more, more preferably 1 × 10 ⁻³ mass% or more with respect to the dry mass of the entire hop composition. Yes, more preferably 2 × 10 ⁻³ mass% or more, and even more preferably 3 × 10 ⁻³ mass% or more. Moreover, the upper limit of the content of the fatty acid ester in the hop composition is not particularly limited, and can be appropriately adjusted according to each condition of the contact step, but as an example, with respect to the dry mass of the entire hop composition It can be about 1 × 10 ⁻¹ mass%.

  The fatty acid ester is preferably isobutyric acid ester, isovaleric acid ester, 2-methylbutyric acid ester or a combination thereof, more preferably ethyl isobutyrate, ethyl isovalerate and ethyl 2-methylbutyrate. .

  The content of the bitter component in the hop composition of the present invention can be adjusted depending on the conditions of the contact process, but is low from the viewpoint of both imparting fruit-like aroma and suppressing hop-derived bitterness. Is preferred. About content of the bitterness component in a hop composition, when converting into the total content of alpha acid and iso alpha acid with respect to the dry mass of the whole hop composition, a suitable minimum shall be 0 mass% or 0.01 mass%. The preferred upper limit can be 2%, 0.2%, 0.1% or 0.05% by weight. Moreover, the suitable range of content of the bitterness component in a hop composition becomes like this. Preferably it is 0-2 mass%, More preferably, it is 0-0.5 mass%.

  The hop composition of the present invention preferably contains a high level of mature hop bitter acids (MHBA), which are oxides of bitter acids such as α acids, β acids, and iso α acids. MHBA has very low bitter taste and has health functional effects such as lipid metabolism function improving action as compared with α acid, β acid, iso α acid and the like (Patent No. 5980687, Biosci. Biotech. Biochem). 2015; 79: 1684-1694., PLoS One. 2015; 10: e0131042 / 1-e0131042 / 14., Nutr J. 2016; 15: 25.), Which is advantageous for imparting health functions to hop compositions. is there. Preferable examples of the components constituting such MHBA include compounds described in the following formulas (1a-c) to (8a-c). The MHBA can be quantified according to the method described in Test Example 2 described later.

  For the content of MHBA in the hop composition of the present invention, the preferred lower limit can be 0.1% by mass, 0.5% by mass or 1% by mass with respect to the dry mass of the entire hop composition, A suitable upper limit can be 5 mass%, 10 mass%, or 20 mass%. Moreover, the range of the content of MHBA in the hop composition of the present invention is preferably 0.1 to 20% by mass, more preferably 1 to 20% by mass.

  In addition, from the standpoint of reducing bitterness and imparting health function, the content of MHBA in the hop composition is preferably equal to or greater than the bitterness component (total amount of α acid and iso α acid). More preferably, it is 4 times or more, more preferably 50 times or more, and still more preferably 90 times or more.

Food / Beverage Use / Fatty Acid Ester Application Method The hop composition of the present invention may be added directly or indirectly to the food / beverage product as an extract to give a fruit-like aroma while reducing the bitterness derived from hops. Can do. Moreover, the hop composition of this invention is good also as food-drinks as it is. Therefore, according to this invention, the hop origin food-drinks which use the hop composition of this invention as a raw material or contain it are provided.

The hop origin food / beverage products of this invention can be manufactured by mixing a hop composition or its extract, and another raw material in arbitrary ratios. For example, when the hop composition and other raw materials are mixed at a ratio of 1: 100, the content of the fatty acid ester in the hop-derived food or drink of the present invention is preferably 1 × 10 ^{− based on} the mass of the whole food or drink. ^{It is 6} % by mass or more, more preferably 1 × 10 ⁻⁵ % by mass or more, further preferably 2 × 10 ⁻⁵ % by mass or more, and further preferably 3 × 10 ⁻⁵ % by mass or more. Moreover, the suitable range of content of the bitterness component ((alpha) acid and iso (alpha) acid) in the hop origin food / beverage products of this invention, Preferably it is 0-0.0005 mass% with respect to the mass of the whole food / beverage products, More preferably, it is 0-0.001 mass%.

  The hop-derived food or drink is particularly preferably a beverage having a fruit-like aroma by adding a hop composition, a pulverized product or an extract thereof to an aqueous medium such as water or alcohol. Suitable examples of such beverages include soft drinks, alcoholic beverages, and beer-taste beverages.

  According to another aspect, according to the present invention, there is provided a method for imparting a fatty acid ester to a hop, comprising the step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with the hop. Is done. This method can be carried out by those skilled in the art according to the description of the method for producing the fatty acid ester-containing hop composition of the present invention.

  The present invention will be specifically described based on the following examples, but the present invention is not limited to these examples. Unless otherwise specified in the present specification, the details of the implementation of the invention follow the provisions of the Japanese Industrial Standard (JIS).

Test example 1
Hop pellets (hopsteiner, Mainburg, Germany) used cheap bitter varieties compared to aroma varieties. The hop pellets were pulverized by a mill, and the hop pulverized product was heated at 60 ° C. for 120 hours in the atmosphere. The obtained oxidized hop was used as a processing raw material, and extraction was performed according to the conditions described below.

Extraction condition 1 (supercritical carbon dioxide extraction-no entrainer)
40 g of oxidized hop was extracted with supercritical carbon dioxide under the following conditions to obtain an oxidized hop carbon dioxide extraction residue.
Temperature: 40 ° C
Pressure: 30 MPa
CO2 consumption: 4000 g (20 g / min)
Carbon dioxide distribution time: 200 min

Extraction condition 2 (supercritical carbon dioxide extraction-with entrainer)
40 g of oxidized hop was extracted with supercritical carbon dioxide under the following conditions to obtain an oxidized hop carbon dioxide extraction residue.
Temperature: 40 ° C
Pressure: 30 MPa
CO2 consumption: 4000 g (20 g / min)
Carbon dioxide distribution time: 200 min
Entrainer: Ethanol (20% vs carbon dioxide, 4 mL / min)

Determination of fatty acid ester in hops 1.5 g of hop, oxidized hop or oxidized hop carbon dioxide extraction residue not subjected to oxidation treatment was weighed, 60 mL of milli-Q water was added, and extracted at room temperature for 1 hour. The obtained extract was centrifuged at 2000 rpm for 10 min, and the supernatant was collected and analyzed by SPME-GCMS under the conditions shown below. Determination of fatty acid esters (ethyl isobutyrate, ethyl isovalerate and ethyl 2-methylbutyrate) was carried out by the standard addition method.

[SPME-GCMS]
Column: InertCap AQUATIC-2 0.25 mm x 60 m, film thickness 1.40 μm
Inlet: Splitless inlet temperature: 260 ° C
Column flow rate: 1.5 mL / min
Oven temperature: 50 ℃ (5 min) → 8 ℃ / min → 260 ℃ (15 min)
MSD transfer line temperature: 260 ° C
Scan range: m / z 29-450
SPME fiber: 50 / 30μm DVB / CAR / PDMS Stableflex (2 cm)
Incbation temp & time ： 60 ℃, 10 min
Extraction time: 25 min
Desorption time: 300 s

The results of fatty acid ester determination are shown in Table 1. Fatty acid esters were not detected in hops that were not subjected to oxidation treatment and in oxidized hops. No fatty acid ester was detected in the oxidized hop carbon dioxide extraction residue (extraction condition 1: supercritical carbon dioxide extraction-without entrainer) as well.
On the other hand, fatty acid esters were detected in the oxidized hop carbon dioxide extraction residue (extraction condition 2: supercritical carbon dioxide extraction-with entrainer). Also, only this sample had a refreshing fruit-like aroma due to the fatty acid ester.

  As described above, by adding ethanol as an entrainer during supercritical carbon dioxide extraction treatment of hops, it was possible to efficiently produce fatty acid esters in the hops and to give refreshing fruit-like aromas to the hops. .

Test example 2
The precursor of the fatty acid ester produced in Test Example 1 is a fatty acid (isobutyric acid, isovaleric acid and 2-methylbutyric acid) produced by oxidative decomposition of a bitter acid such as α acid, β acid or isoα acid contained in hops. ). Therefore, the α acid and iso α acid, their oxides MHBA, and fatty acid were used in the sample used in Test Example 1 [extracted hop, oxidized hop, or oxidized hop carbon dioxide extraction residue (extracted from oxidation treatment) Condition 2: Supercritical carbon dioxide extraction-with entrainer)] was measured.

Quantitative determination of alpha acid, iso alpha acid, MHBA hop, oxidized hop or oxidized hop carbon dioxide extraction residue (extraction condition 2: supercritical carbon dioxide extraction-with entrainer) 10 g of ethanol was added to 1.0 g In addition, extraction was performed at room temperature for 1 hour. The obtained extract was centrifuged at 2000 rpm for 10 min, the supernatant was diluted 10-fold with ethanol, passed through a 0.22 μm filter, and used as an HPLC analysis sample. In addition, the quantification of α acid and iso α acid by HPLC is in accordance with the method described in J. Agric. Food. Chem. 2013; 61: 3121-3130. The MHBA is quantified in Biosci. Biotech. Biochem. 2015; 79: 1684-1694. The HPLC measurement conditions for α acid, iso α acid, and MHBA were as follows. Here, as described in Biosci. Biotech. Biochem. 2015; 79: 1684-1694, MHBA is used for the retention time of caffeine and trans-isocohumulone (approximately 3 minutes to 25 minutes from the start of measurement) under the following HPLC measurement conditions. Corresponds to the peak present during

[HPLC conditions]
Column: Alltima C18 2.1mm ID x 100mm Particle size 3μm
Flow rate: 0.6mL / min
Mobile phase A: water / phosphoric acid, 1000 / 0.2, (v / v) + EDTA (free) 0.02% (w / v)
Mobile phase B: Acetonitrile mobile phase C: Water injection volume: 3 μL
Column temperature: 40 ° C
Photodiode array detector: SPD-M20A (SHIMADZU)
Detection wavelength: 270nm (α acid, iso α acid, MHBA)
Waveform analysis software: LCSolution (SHIMADZU)
Gradient program:

Determination of fatty acid 1.0 g of hop, oxidized hop or oxidized hop carbon dioxide extraction residue not subjected to oxidation treatment was weighed, 10 mL of milli-Q water was added, and extracted at room temperature for 1 hour. The obtained extract was centrifuged at 2000 rpm for 10 min, and the supernatant was collected, applied to a 0.22 μm filter, and analyzed by HPLC.

[Fatty acid quantitative HPLC conditions]
Column: Shim-pak SPR-H (250 x 7.8 mm) Double connecting guard column: Shim-pak SPR-H (G) (50 x 7.8 mm)
Column oven: 40 ° C
Mobile phase: 4 mM p-toluenesulfonic acid post-column detection solution: 16 mM Bis-Tris containing 4 mM p-toluenesulfonic acid, 100 μM EDTA-2Na
Mobile phase flow rate: 0.8 mL / min
Post-column detection solution flow rate: 0.8 mL / min
Detection: Electrical conductivity detector polarity (+), 43 ℃
Injection volume: 15 μL

A calibration curve was prepared using three commercially available reagents for the three fatty acids isobutyric acid, isovaleric acid and 2-methylbutyric acid, and the concentration in the sample was quantified. In addition, isovaleric acid and 2-methylbutyric acid were confirmed to have the same elution time and that there was no difference in the detection sensitivity of both in the analysis using isovaleric acid and 2-methylbutyric acid, These were quantified as the total amount of the two compounds. The results are shown in Table 3.

Oxidation of hops increased the fatty acid content as a precursor of fatty acid esters. From this, in order to efficiently produce a fatty acid ester, it is considered preferable to perform supercritical carbon dioxide extraction treatment using an entrainer in combination with an oxidized hop having a high fatty acid content as a precursor.
In addition, the oxidized hop carbon dioxide extraction residue after the supercritical carbon dioxide extraction treatment using alcohol as an entrainer is substantially free from the amount of alpha acid and iso alpha acid that are bitter components, while MHBA It remained. Since MHBA has very low bitterness, the supercritical carbon dioxide extraction residue corresponding to the hop composition of the present invention has no fear of imparting excessive bitterness to the beverage, and is suitable as a material for imparting fruit-like aroma to the beverage. Conceivable.

Claims (12)

  A method for producing a fatty acid ester-containing hop composition comprising a step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with a hop. The method according to claim 1, wherein the content of the fatty acid ester in the hop composition is 1 × 10 ⁻⁴ mass% or more.    The method according to claim 1, wherein the total content of α-acid and iso-α-acid in the hop composition is 2% by mass or less.    The production method according to any one of claims 1 to 3, wherein the content of ripened hop bitter acid (MHBA) in the hop composition is equal to or greater than the total content of α acid and iso α acid. .    The manufacturing method as described in any one of Claims 1-4 whose said alcohol is ethanol.   The manufacturing method according to any one of claims 1 to 5, wherein the fatty acid ester is at least one selected from ethyl isobutyrate, ethyl isovalerate, and ethyl 2-methylbutyrate. The fatty acid ester containing hop composition whose content of fatty acid ester is 1 × 10 ⁻⁴ mass% or more.   The hop composition according to claim 7, wherein the total content of α-acid and iso-α-acid is 2% by mass or less.   The hop composition according to claim 7 or 8, which is obtained by the method according to any one of claims 1 to 6.   The hop origin food-drinks which use the hop composition as described in any one of Claims 7-9 as a raw material, or contain it.   The food / beverage products of Claim 10 which is a drink.   A method for imparting a fatty acid ester to a hop, comprising a step of bringing a mixed fluid containing supercritical carbon dioxide and alcohol into contact with the hop.