WO2024134960A1 - 酸味が抑制された非アルコールビールテイスト飲料 - Google Patents
酸味が抑制された非アルコールビールテイスト飲料 Download PDFInfo
- Publication number
- WO2024134960A1 WO2024134960A1 PCT/JP2023/027920 JP2023027920W WO2024134960A1 WO 2024134960 A1 WO2024134960 A1 WO 2024134960A1 JP 2023027920 W JP2023027920 W JP 2023027920W WO 2024134960 A1 WO2024134960 A1 WO 2024134960A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alcoholic beer
- beverage
- beer
- present
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/38—Other non-alcoholic beverages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/06—Function of food ingredients pH modification agent
Definitions
- the present invention relates to a non-alcoholic beer-flavored beverage and a method for producing the same.
- non-alcoholic beer-flavored beverages have various flavor balance issues.
- the inventors discovered a problem with non-alcoholic beer-flavored beverages: the balance of flavors that is normally harmonised by the alcohol is lost, resulting in a prominent sour taste.
- the inventors have investigated the above problems and found that the sourness of non-alcoholic beer-flavored beverages can be reduced by adjusting the concentration of 5-methyl-2-furfural (CAS: 67-47-0).
- the present invention is based on this finding.
- the present invention therefore provides a non-alcoholic beer-flavored beverage with reduced sourness and a method for producing the same.
- a non-alcoholic beer-flavored beverage having a 5-methyl-2-furfural content of 10 ppb or more (2) A non-alcoholic beer-flavored beverage as described in (1) above, in which the alcohol (ethanol) concentration is less than 0.005 v/v%.
- a non-alcoholic beer-flavored beverage according to (1) or (2) above having a caprylic acid content of 0.3 ppm or more.
- a non-alcoholic beer-flavored beverage according to (1) or (2) above having a capric acid content of 0.03 ppm or more.
- a method for producing a non-alcoholic beer-taste beverage comprising a step of adjusting the 5-methyl-2-furfural content in the non-alcoholic beer-taste beverage to 10 ppb or more.
- a method for reducing the sourness of a non-alcoholic beer-taste beverage the method comprising a step of adjusting the content of 5-methyl-2-furfural in the non-alcoholic beer-taste beverage to 10 ppb or more.
- a "beer-taste beverage” refers to a beverage that has a beer-like flavor.
- "Beer-like flavor” means that the beverage exhibits the unique taste and aroma of beer that can be obtained when beer is produced in the usual way, i.e., when beer is produced based on fermentation by yeast, etc.
- a "non-alcoholic beer-taste beverage” refers to a beer-taste beverage with an alcohol (ethanol) concentration of less than 1% (v/v).
- the alcohol concentration of the non-alcoholic beer-taste beverage of the present invention is less than 0.75% (v/v), more preferably less than 0.5% (v/v), even more preferably less than 0.05% (v/v), even more preferably less than 0.01% (v/v), even more preferably less than 0.009% (v/v), even more preferably less than 0.008% (v/v), even more preferably less than 0.007% (v/v), even more preferably less than 0.006% (v/v), and even more preferably less than 0.005% (v/v).
- ppm is synonymous with “mg/L” and the unit “ppb” is synonymous with “ ⁇ g/L”.
- the non-alcoholic beer-flavored beverage of the present invention contains 5-methyl-2-furfural in a specified concentration range.
- the non-alcoholic beer-flavored beverage of the present invention further contains caprylic acid (CAS: 124-07-2) and/or capric acid (CAS: 334-48-5) in specified concentrations.
- the non-alcoholic beer-flavored beverage of the present invention can be produced by adjusting the content of 5-methyl-2-furfural during the production process of the non-alcoholic beer-flavored beverage. Furthermore, according to a preferred embodiment of the present invention, the content of caprylic acid and/or capric acid is also adjusted during the production process of the non-alcoholic beer-flavored beverage of the present invention.
- the contents of 5-methyl-2-furfural, caprylic acid and capric acid may be adjusted, for example, by adding these substances during the production process of the non-alcoholic beer-flavored beverage, by increasing or decreasing the amount of raw materials that provide these substances to the non-alcoholic beer-flavored beverage, or by adjusting various conditions during production (for example, conditions during the brewing process, saccharification process, fermentation process, etc.).
- the lower limit of the 5-methyl-2-furfural content in the non-alcoholic beer-flavored beverage of the present invention is 10 ppb, preferably 25 ppb, more preferably 50 ppb, even more preferably 75 ppb, even more preferably 100 ppb, even more preferably 250 ppb, and even more preferably 500 ppb.
- the upper limit of the 5-methyl-2-furfural content in the non-alcoholic beer-flavored beverage of the present invention is not particularly limited.
- an upper limit of the 5-methyl-2-furfural content may be, for example, 100,000 ppb, preferably 10,000 ppb, more preferably 1,000 ppb, and even more preferably 500 ppb.
- the 5-methyl-2-furfural content in the non-alcoholic beer-taste beverage of the present invention is 10 ppb or more, preferably 10 to 100,000 ppb, more preferably 10 to 10,000 ppb, even more preferably 10 to 1,000 ppb, and even more preferably 10 to 500 ppb.
- the amount of 5-methyl-2-furfural in a beverage can be quantified by GC/MS analysis. Specifically, first, the aroma components in the beverage are separated using a C18 solid-phase extraction column, and the resulting analytical sample is subjected to GC/MS. In addition, borneol can be used as an internal standard substance.
- the conditions for GC/MS analysis can be, for example, those shown in the examples. For more accurate concentration measurement, it is desirable to use a calibration curve created based on the measured values of several control samples with known concentrations.
- the caprylic acid content in the non-alcoholic beer-flavored beverage of the present invention is 0.3 ppm or more, more preferably 0.5 ppm or more, even more preferably 0.7 ppm or more, even more preferably 1.0 ppm or more, and preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less, and even more preferably 5.0 ppm or less.
- the capric acid content in the non-alcoholic beer-flavored beverage of the present invention is 0.03 ppm or more, preferably 0.06 ppm or more, more preferably 0.1 ppm or more, and preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less, and even more preferably 5.0 ppm or less.
- Caprylic acid and capric acid in beverages can be quantified by gas chromatography (GC) with an FID detector. Specifically, the aroma components in the beverage are extracted using a hydroxylated polystyrene divinylbenzene copolymer solid-phase column, and the resulting extract is subjected to GC/FID. Trans-2-hexanoic acid and methyl caprylate can be used as internal standards.
- the analytical conditions for GC can be, for example, those shown in the Examples. For more accurate concentration measurements, it is desirable to use a calibration curve created based on the measured values of several control samples with known concentrations.
- the non-alcoholic beer-flavored beverage of the present invention may contain other ingredients as long as the effects of the present invention are not impaired.
- the non-alcoholic beer-flavored beverage of the present invention may contain colorants (e.g., caramel color), sweeteners (e.g., high-intensity sweeteners), seasoning ingredients (e.g., amino acids), flavorings (e.g., commercially available beer flavors containing ethyl acetate, isoamyl acetate, isoamyl alcohol, etc., which are typical aroma components of beer), bitter components such as isomerized hop extract, yeast extract, etc. as ingredients.
- colorants e.g., caramel color
- sweeteners e.g., high-intensity sweeteners
- seasoning ingredients e.g., amino acids
- flavorings e.g., commercially available beer flavors containing ethyl acetate, isoamyl acetate, isoamyl alcohol, etc., which are typical aroma components
- the pH of the non-alcoholic beer-taste beverage of the present invention (measured at 25°C) is preferably 3.5 or higher and 4.5 or lower, more preferably 3.7 or higher and 4.5 or lower, even more preferably 3.8 or higher and 4.5 or lower, and most preferably 3.8 or higher and 4.2 or lower.
- the pH of the non-alcoholic beer-taste beverage of the present invention can be adjusted using a pH adjuster.
- the non-alcoholic beer-tasted beverage of the present invention is a non-alcoholic beer-tasted beverage made from malt, more preferably a non-alcoholic beer-tasted beverage made from barley malt.
- the non-alcoholic beer-tasted beverage of the present invention is a non-alcoholic beer-tasted beverage made from wort.
- the non-alcoholic beer-tasted beverage of the present invention is a non-alcoholic beer-tasted beverage made from hops.
- the non-alcoholic beer-tasted beverage of the present invention is a beverage in which carbon dioxide gas is dissolved, that is, a non-alcoholic beer-tasted carbonated beverage.
- the non-alcoholic beer-taste beverage of the present invention can be produced by adjusting the content of 5-methyl-2-furfural at any stage in a general method well known in the art.
- a general method includes, for example, a method including a wort preparation step and a filtration step, and this method can be carried out, for example, by sequentially carrying out the steps of (a) saccharifying a mixture of malt powder and water, filtering the mixture to obtain wort, (b) adding hops to the obtained wort, followed by boiling, (c) cooling the boiled wort, and (d) filtering the cooled wort.
- a general method includes a method of producing a fermented malt beverage such as beer, and then removing alcohol from the obtained fermented malt beverage.
- Methods for removing alcohol from beverages include (i) a method of removing alcohol and low-boiling point components by distillation at reduced pressure or normal pressure, (ii) a method of removing alcohol and low-molecular components using a reverse osmosis (RO) membrane, and (iii) a method of removing volatile components by adsorbing them to steam using centrifugal force.
- a method of removing alcohol and low-boiling point components by distillation at reduced pressure or normal pressure a method of removing alcohol and low-molecular components using a reverse osmosis (RO) membrane
- RO reverse osmosis
- a method for reducing the sourness of a non-alcoholic beer-flavored beverage comprising the step of adjusting the content of 5-methyl-2-furfural in the non-alcoholic beer-flavored beverage to 10 ppb or more.
- Example 1 Effect on flavor of adjusting the concentration of 5-methyl-2-furfural, caprylic acid, and capric acid in a non-alcoholic beer-flavored beverage
- Sample preparation 1 kg of malt was crushed to an appropriate particle size and placed in a brewing tank, to which 3 L of warm water was added. After holding at 65°C for 20 minutes, the temperature was gradually raised and saccharification was performed at 76°C for 15 minutes. After saccharification was completed, the temperature was raised to 78°C, and then filtration was performed using filter paper to obtain a filtrate. About 0.1 g of hops was added to 1 L of this filtrate, and the mixture was boiled at 100°C for 60 minutes. The boiled liquid was filtered using filter paper and cooled to about 5°C.
- Hot water was added to the obtained liquid as appropriate so that the sugar content was 3.0°P to adjust the wort.
- Carbonated water and carbon dioxide gas were added to this wort, and the mixture was stored at 2 to 4°C for 24 hours, and then filtered.
- a beer flavoring was added to the filtered liquid, and the obtained liquid was designated as base beverage sample A.
- the alcohol (ethanol) concentration of base beverage sample A was less than 0.005 v/v %.
- this beverage was subjected to an alcohol removal process, and the resulting liquid was designated as base beverage sample B.
- crushed malt, enzymes, and warm water were placed in a brewing tank, and saccharification was performed at a temperature of 60°C to 78°C.
- This saccharified liquid was filtered, transferred to a boiling kettle, hops were added, and boiled for 70 minutes. After boiling, the evaporated warm water was added to the resulting mixture, and the heat trub was removed in a whirlpool tank, and then cooled to 10°C to obtain cold wort. Beer yeast was added to this wort, and fermented at around 10°C for 7 days, after which the beer yeast was removed.
- the resulting mixture was transferred to another tank and aged for 7 days, after which it was cooled to around -1°C and stabilized for 14 days.
- the resulting mixture was then diluted with degassed water and filtered to obtain a wort fermentation liquid.
- it was sprayed into a degassing tank to remove carbon dioxide, and then heated to around 50°C.
- the mixture was then brought into contact with steam heated to around 50°C in a vacuum column at around 60 mbar, causing the volatile components to be adsorbed by the steam, and the alcohol and volatile components were removed to obtain a dealcoholized wort fermentation liquid with an alcohol concentration of less than 0.005 v/v%.
- This dealcoholized wort fermentation liquid was used as base beverage sample B (alcohol (ethanol) concentration less than 0.005 v/v%).
- 5-methyl-2-furfural 5-methyl-2-furfural
- caprylic acid 5-methyl-2-furfural
- capric acid was added to the base beverage samples to the concentrations shown in the table below.
- the concentration of 5-methyl-2-furfural (5MF) in each beverage sample in the examples was measured by GC/MS analysis under the following conditions. Specifically, the aroma components in the beverage samples were separated using a C18 solid phase column, and the resulting analytical sample was subjected to GC/MS. Quantitation was performed using the internal standard method, with borneol used as the internal standard, added to the analytical sample at 50 ppb. The GC/MS analysis conditions were as shown in the table below.
- the concentrations of caprylic acid and caproic acid in each beverage in the examples were measured using gas chromatography (GC) with an FID detector. Specifically, the aroma components in the beverages were extracted using a hydroxide polystyrene divinylbenzene copolymer solid-phase column, and the resulting extract was subjected to GC/FID. Trans-2-hexanoic acid and methyl caprylate were used as internal standards.
- the GC analysis conditions were as shown in the table below.
- the evaluation score of the blended base beverage sample that did not contain 5-methyl-2-furfural (5MF), caprylic acid, or capric acid was fixed at 10
- the evaluation score of the beverage sample that contained 10 ppb of 5-methyl-2-furfural (5MF), 0.3 ppm of caprylic acid, and 0.03 ppm of capric acid was fixed at 1.
- Results The results of the sensory evaluation are shown in the table below. The results of the sensory evaluation are shown as the average score and standard deviation of the scores of the seven panelists.
- the results of Test 1 in Table 3 make it clear that 5-methyl-2-furfural has the effect of reducing sourness, and that this effect is particularly pronounced at concentrations of 10 ppb or more.
- the results of Test 2 show that the effect of reducing sourness becomes more pronounced when the concentration of caprylic acid is adjusted to 0.3 ppm or more in addition to 5-methyl-2-furfural.
- the results of Test 3 show that the effect of reducing sourness becomes more pronounced when the concentration of capric acid is adjusted to 0.03 ppm or more in addition to 5-methyl-2-furfural.
- the results of Test 4 show that an excellent effect of reducing sourness can be obtained by adjusting the concentrations of the combination of 5-methyl-2-furfural, caprylic acid, and capric acid.
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- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Non-Alcoholic Beverages (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202380079728.5A CN120187306A (zh) | 2022-12-23 | 2023-07-31 | 酸味得到了抑制的无酒精啤酒味饮料 |
| KR1020257024206A KR20250123206A (ko) | 2022-12-23 | 2023-07-31 | 산미가 억제된 비알코올 맥주 테이스트 음료 |
| AU2023409446A AU2023409446A1 (en) | 2022-12-23 | 2023-07-31 | Non-alcoholic beer-taste beverage having suppressed sourness |
| JP2023547399A JP7608626B2 (ja) | 2022-12-23 | 2023-07-31 | 酸味が抑制された非アルコールビールテイスト飲料 |
| JP2024217613A JP2025038065A (ja) | 2022-12-23 | 2024-12-12 | 酸味が抑制された非アルコールビールテイスト飲料 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022207319 | 2022-12-23 | ||
| JP2022-207319 | 2022-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024134960A1 true WO2024134960A1 (ja) | 2024-06-27 |
Family
ID=91588038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2023/027920 Ceased WO2024134960A1 (ja) | 2022-12-23 | 2023-07-31 | 酸味が抑制された非アルコールビールテイスト飲料 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7608626B2 (https=) |
| KR (1) | KR20250123206A (https=) |
| CN (1) | CN120187306A (https=) |
| AU (1) | AU2023409446A1 (https=) |
| WO (1) | WO2024134960A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2026004996A1 (ja) * | 2024-06-28 | 2026-01-02 | キリンホールディングス株式会社 | ビールテイスト発酵飲料およびその製造方法 |
| JP7812977B1 (ja) * | 2024-08-30 | 2026-02-10 | キリンホールディングス株式会社 | ビールテイストノンアルコール飲料およびその製造方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015027309A (ja) * | 2014-09-30 | 2015-02-12 | 太一 染谷 | ビール風味付与剤およびビール風味飲料 |
| JP2015053877A (ja) * | 2013-09-11 | 2015-03-23 | 株式会社カネカ | 麦由来の風味改良剤を含有する飲料 |
| JP2017023017A (ja) * | 2015-07-17 | 2017-02-02 | 長谷川香料株式会社 | 高甘味度甘味料の呈味改善剤 |
-
2023
- 2023-07-31 CN CN202380079728.5A patent/CN120187306A/zh active Pending
- 2023-07-31 JP JP2023547399A patent/JP7608626B2/ja active Active
- 2023-07-31 AU AU2023409446A patent/AU2023409446A1/en active Pending
- 2023-07-31 WO PCT/JP2023/027920 patent/WO2024134960A1/ja not_active Ceased
- 2023-07-31 KR KR1020257024206A patent/KR20250123206A/ko active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015053877A (ja) * | 2013-09-11 | 2015-03-23 | 株式会社カネカ | 麦由来の風味改良剤を含有する飲料 |
| JP2015027309A (ja) * | 2014-09-30 | 2015-02-12 | 太一 染谷 | ビール風味付与剤およびビール風味飲料 |
| JP2017023017A (ja) * | 2015-07-17 | 2017-02-02 | 長谷川香料株式会社 | 高甘味度甘味料の呈味改善剤 |
Non-Patent Citations (1)
| Title |
|---|
| RIU-AUMATELL, M. ET AL.: "Assessment of the aroma profiles of low-alcohol beers using HS- SPME-GC-MS", FOOD RESEARCH INTERNATIONA L., vol. 57, 2014, pages 196 - 202, XP028614096, DOI: 10.1016/j.foodres.2014.01.016 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2026004996A1 (ja) * | 2024-06-28 | 2026-01-02 | キリンホールディングス株式会社 | ビールテイスト発酵飲料およびその製造方法 |
| JP7812977B1 (ja) * | 2024-08-30 | 2026-02-10 | キリンホールディングス株式会社 | ビールテイストノンアルコール飲料およびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP7608626B2 (ja) | 2025-01-06 |
| AU2023409446A1 (en) | 2025-07-03 |
| KR20250123206A (ko) | 2025-08-14 |
| JPWO2024134960A1 (https=) | 2024-06-27 |
| CN120187306A (zh) | 2025-06-20 |
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