AU2016206336B2 - A beverage containing isobutanol and/or isoamyl alcohol - Google Patents

Abstract

A BEVERAGE CONTAINING ISOBUTANOL AND/OR ISOAMYL ALCOHOL ABSTRACT The present invention provides a beverage that contains isobutanol and/or isoamyl alcohol and which yet has their pungent odor masked and is free from any oily smell so that it can be drunk with a refreshing sensation. In a beverage containing (A) isobutanol and/or isoamyl alcohol and (B) limonene and/or nootkatone, the sum of the contents of isobutanol and isoamyl alcohol is adjusted to 60 to 1000 ppm, the content of limonene is adjusted to 0.25 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of limonene is adjusted to 30 to 1000. In addition or alternatively, the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone is adjusted to 100 to 2500.

Description

A BEVERAGE CONTAINING ISOBUTANOL AND/OR ISOAMYL ALCOHOL

This application claims priority from Japanese Application No. 147267/2015 filed on 24 July 2015 and Japanese Application No. 064766/2016 filed on 28 March 2016, the contents of which are to be taken as incorporated herein by this reference.

The present invention relates to a packaged beverage containing isobutanol and/or isoamyl alcohol.

It is known that in addition to ethanol, by-products such as isobutanol and isoamyl alcohol are produced in alcohol fermentation. Generally, these volatile components that have higher boiling points than ethanol are called fusel oils. While fusel oils are among ingredients that provide various alcoholic liquors and non-alcoholic beverages with their characteristic, complex, and profound flavors, they also present a pungent and oily odor and therefore may act in an unfavorable way on the balance of the whole of the flavors and tastes of the alcoholic liquors depending on their composition and amount. As a way to reduce the content of fusel oils in alcoholic liquors, Patent Document 1 discloses a method of using yeast cells having no or reduced activity of one or both of the branched-chain amino acid aminotransferase (BCAT) isoenzymes in the fermentation-based production of alcoholic beverages having low concentrations of fusel oils, and the document also states that this method suppresses the formation of fusel oils during the fermentation process in the production of alcoholic beverages.

Patent Document 1: JP 2002-509726 A

Although fusel oils such as isobutanol and isoamyl alcohol present the pungent and somewhat oily odor, removing these oils as described in Patent Document 1 may result in the loss of the individual characteristics of the treated beverages, i.e. the profound flavors and complex tastes that are unique to them.

As a method of masking the pungent and somewhat oily odor of beverages containing fusel oils such as isobutanol and isoamyl alcohol, the present inventors conceived of adding citrus fruit derived flavoring components. However, it was found that simply incorporating the citrus fruit derived flavoring components led to the combination of the oily odor of fusel oils with the oily smell and slight bitterness of such citrus fruit derived flavoring components, thereby making the beverage rather oily and difficult to drink. The inventors further conducted intensive studies on the aforementioned problems and found that when specific amounts of limonene and/or nootkatone were contained at a specific ratio in a beverage containing specific amounts of isobutanol and/or isoamyl alcohol, the pungent odor of isobutanol and/or isoamyl alcohol was masked while their profound flavor and complex taste were maintained in the beverage that was also free from the oily smell and could therefore be drunk with a refreshing sensation. Thus, the present invention includes but is not limited to the following embodiments: (1) A packaged beverage containing: (A) isobutanol and/or isoamyl alcohol; and (B) limonene and/or nootkatone, wherein the sum of the contents of isobutanol and isoamyl alcohol is 60 to 1000 ppm, and the packaged beverage satisfies either or both of the following conditions i) and ii): i) when the beverage contains limonene, the content of limonene is 0.25 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of limonene is 30 to 1000; and ii) when the beverage contains nootkatone, the content of nootkatone is 0.05 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone is 100 to 2500. (2) The packaged beverage according to (1), wherein the alcohol content is 0 to 40 v/v%. (3) The packaged beverage according to (1), wherein the alcohol content is 3 to 9 v/v%. (4) The packaged beverage according to any one of (1) to (3), wherein the fruit juice percentage of the beverage is 0.1 w/w% to 40 w/w%. (5) The packaged beverage according to any one of (1) to (4), which contains carbon dioxide gas. (6) The packaged beverage according to (5), wherein the pressure of the carbon dioxide gas is no less than 1.5 kgf/cm 2 .

(7) The packaged beverage according to any one of (1) to (6), wherein the sum of the contents of sucrose, glucose, and fructose is no more than 1.7 g/100 ml.

13418201_1 (GHMatters) P109255.AU

- 2a

The present invention as claimed herein is described in the following items 1 to 5: 1. A packaged beverage containing: (A) isobutanol and/or isoamyl alcohol; and (B) limonene and/or nootkatone, wherein the sum of the contents of isobutanol and isoamyl alcohol is 60 to 1000 ppm, the packaged beverage contains carbon dioxide gas, and the pressure of the carbon dioxide gas is in the range of 1.5 kgf/cm 2 to 3.0 kgf/cm 2

, and the packaged beverage satisfies either or both of the following conditions (i) and (ii): i) when the beverage contains limonene, the content of limonene is 0.25 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of limonene is 30 to 1000; and ii) when the beverage contains nootkatone, the content of nootkatone is 0.05 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone is 100 to 2500. 2. The packaged beverage according to item 1, wherein the alcohol content is 0 to 40 v/v%. 3. The packaged beverage according to item 1, wherein the alcohol content is 3 to 9 v/v%. 4. The packaged beverage according to any one of items 1-3, wherein the fruit juice percentage of the beverage is 0.1 w/w% to 40 w/w%. 5. The packaged beverage according to any one of items 1-4, wherein the sum of the contents of sucrose, glucose, and fructose is no more than 1.7 g/100 ml.

The present invention can provide a beverage that contains isobutanol and/or isoamyl alcohol and which yet has their pungent odor masked and can be drunk with a refreshing sensation in the absence of an oily smell.

In the present invention, specific amounts of limonene and/or nootkatone are

13418201_1 (GHMatters) P109255.AU incorporated at a specific ratio in a beverage containing isobutanol and/or isoamyl alcohol known as fusel oils in a total amount of 60 tol000 ppm, thereby providing a beverage that has the pungent odor of isobutanol and/or isoamyl alcohol masked and can be drunk with a refreshing sensation in the absence of any oily smell. (Isobutanol and isoamyl alcohol) Isobutanol (isobutyl alcohol) and isoamyl alcohol (3-methyl-1-butanol) are among fusel oils that are produced as by-products in alcohol fermentation. Each alcohol is an ingredient that provides various alcohols with their characteristic flavors but which itself has the pungent odor. The beverage of the present invention contains either or both of isobutanol and/or isoamyl alcohol. The beverage of the present invention contains isobutanol and/or isoamyl alcohol in such amounts that the sum of their contents is 60 to 1000 ppm, preferably 80 to 500 ppm, more preferably 100 to 200 ppm. When the sum of the contents of isobutanol and isoamyl alcohol is less than 60 ppm, their pungent odor is hardly perceptible in the first place and the addition of limonene and/or nootkatone to be explained below will not provide any observable effect for masking the pungent odor. On the other hand, if the sum of the contents of isobutanol and isoamyl alcohol is greater than 1000 ppm, the pungent odor becomes so strong that it is difficult to suppress even if limonene and/or nootkatone are added. It should be noted that in the present specification, ppm as a unit is based on ratio by weight and synonymous with mg/L as a unit. The amounts of isobutanol and/or isoamyl alcohol contained in the beverage can be measured by the following method. <Analysis conditions for isobutanol and isoamyl alcohol> Equipment to be used: GC: 6890N of Agilent Technologies Columns to be used: SUPELCO 5% CARBOWAX 20Mon80/120 Carbopack BAW 8FT x 1/41N x 2mm IDGLASS Packed Column Carrier gas: Nitrogen gas Flow: 18.8 mL/min Inlet temperature: 200°C Column temperature: 70°C (0 minutes retention) to 154°C (10 minutes retention), Rising at a speed of 4°C/min Loading amount: 1.0 [L Detector: FID (Limonene) Limonene (d-limonene, C 1 0 H 1 6) is one of monocyclic monoterpenes that are contained as in the skin of citrus fruits and is an ingredient that presents a so-called citrus-like flavor. The beverage of the present invention contains limonene in addition to the above-mentioned isobutanol and/or isoamyl alcohol. The content of limonene in the beverage of the present invention is 0.25 to 1.60 ppm, preferably 0.35 to 1.50 ppm, more preferably 0.45 to 1.40 ppm. If the content of limonene is less than 0.25 ppm, the effect for masking the pungent odor of isobutanol and/or isoamyl alcohol cannot be sufficiently obtained; if the content of limonene is greater than 1.60 ppm, the oily smell of limonene itself is synergistically combined with the oily smell of isobutanol and isoamyl alcohol as fusel oils, causing damage to the refreshing aftertaste of the beverage. (Nootkatone) Nootkatone (d-Nootkatone, C 1 5 H22 0) is one of sesquiterpene ketones. Nootkatone is a compound having the characteristic flavor of grape fruits (especially white grape fruits) and contained in an especially large amount in Citrus maxima. The beverage of the present invention contains nootkatone in addition to the above mentioned isobutanol and/or isoamyl alcohol. The content of nootkatone in the beverage of the present invention is 0.05 to 1.60 ppm, preferably 0.08 to 1.50 ppm, more preferably 0.09 to 1.40 ppm. If the content of nootkatone is less than 0.05 ppm, the effect for masking the pungent odor of isobutanol and/or isoamyl alcohol cannot be sufficiently obtained; if the content of nootkatone is greater than 1.60 ppm, the oily smell of nootkatone itself is synergistically combined with the oily smell of isobutanol and isoamyl alcohol as fusel oils, causing damage to the refreshing aftertaste of the beverage. The ratio of the sum of the contents of isobutanol and isoamyl alcohol in the beverage of the present invention to its content of limonene ((isobutanol + isoamyl alcohol) / limonene) (ratio by weight) is 30 to 1000, preferably 100 to 800, and more preferably 150 to 500. In addition or alternatively, the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone ((isobutanol + isoamyl alcohol/ nootkatone) (ratio by weight) is 100 to 2500, preferably 500 to 2500. If the above-noted ratios are within the above-specified ranges, the effect for masking the pungent odor of isobutanol and/or isoamyl alcohol is obtained. The contents of limonene and/or nootkatone in the beverage may be adjusted by, for example, adding to the beverage an essential oil, a natural flavoring agent, or a synthetic flavoring agent, etc. which contains limonene and/or nootkatone; alternatively, adjustment may be effected by adding to the beverage the juice of a citrus fruit, a distilled alcoholic liquor using a citrus fruit, and/or an immersion liquor using a citrus fruit, wherein the citrus fruit contains limonene and/or nootkatone, or by adding to the beverage an extract of citrus petals or citrus buds, a herb extract, or a non-citrus flavoring agent. Limonene and/or nootkatone are ingredients that are contained in the skin in larger amounts than in other parts of a citrus fruit, so when a citrus fruit is used, it is preferable to select a form that contains fruit skin or fruit skin oil, e.g., a comminuted fruit juice. When a citrus fruit is used, the type of the fruit is not particularly limited, but preferred are citrus fruits that taste sourish such as grapefruits, lemons, limes, oranges, Citrusjunos, Citrus sudachi, Citrus sphaerocarpa,Citrus hassaku, Chinese orange, Citrus depressa, Citrus maxima, kawachi bankan pomelo, and Citrus unshu which are classified into Citrus, Fortunella, or Poncirus, because they enhance the refreshing sensation of the beverage. When other fruits or food ingredients are used for the beverage, fruits other than citrus fruits, their flowers or buds, or herbs, each containing limonene and/or nootkatone, may be used, and these materials may be combined with fruits or food ingredients that do not contain limonene and/or nootkatone. When fruit juice is used in the beverage, its content depends on how much limonene it contains and is preferably in a range from about 0.1 w/w% to no more than about 40 w/w%, preferably from about 0.5 w/w% to about 30.0 w/w%, and more preferably from 1.0 w/w% to 10.0 w/w%, as calculated for the fruit juice percentage in the total amount of the beverage. If the fruit juice percentage is greater than 40 w/w%, the sourness and sweetness originating from the fruit juice become so prominent that the flavor balance with isobutanol and/or isoamyl alcohol is impaired and the resulting beverage, with its profound flavor and complex taste being impaired, lacks rather than features a refreshing sensation. It should be noted that the "fruit juice percentage" refers to a relative concentration, and straight juice that is obtained by squeezing a fruit is taken as 100%. This percentage can be determined by, for example, carrying out calculation based on the standard for sugar refractometer index or acidity of the straight juice of various fruits that are presented in JAS standards (Japanese Agricultural Standards of fruit beverages). The contents of limonene and/or nootkatone in the beverage can be measured by the following method.

[Measurements of limonene and/or nootkatone] Liquid compositions as samples are subjected to gas chromatography mass spectroscopy analysis (GC-FID) under the following conditions. The analysis conditions are as follows: Pre-analysis treatment; samples are loaded into Extrelut NT-1 columns and extracted with ether. Analyzer; GC 6890N (Agilent Technologies) Columns; HP-ULTRA2, inside diameter: 0.32 mm, length: 50 m, film thickness: 0.52 [m Carrier gas; Helium Flow rate; 2.2 mL/min Inlet; Splitless Inlet temperature; 250°C Oven temperature; 45°C (1.5 min) -+ 5°C/min -+ 230°C (11.5 min)

Detector; FID Detector temperature; 260°C Injection amount; 1.0 1 Standard materials; limonene and/or nootkatone (The content of alcohol) The content of alcohol in the beverage of the present invention is preferably 0 to 40 v/v%, more preferably 0 to 30 v/v%, even more preferably 3 to 25 v/v%, most preferably 3 to 9 v/v%. It should be noted that in the present invention, "alcohol" refers to ethanol unless otherwise stated. That is, the content of alcohol refers to the content of ethanol (v/v%). The content of alcohol in the beverage can be measured by known methods. For example, measurements can be carried out by the methods that are described in the National Tax Agency's Official Methods of Analysis (Heisei 19 Instructions from National Tax Agency, volume 6, revised on June 22, 2007). When the beverage of the present invention contains an alcohol, the type of the alcohol source is not particularly limited and examples include spirits (such as gin, vodka, flavored vodka, rum, tequila, triple sec, as well as material alcohols), liqueurs and cocktails, Japanese distilled spirits (shouchu), whiskey, brandy, cognac, calvados, and the like. Also included are fermented or brewed beverages such as refined sake, wine, sweet fruit liquor, beer, beer cocktails, and cider. One or more of these beverages can be used independently or in combination. The beverage of the present invention may contain carbon dioxide gas. Beverages containing carbon dioxide gas are generally of such a nature that due to the popping feel the carbon dioxide gas produces in the mouth, their unique flavor is easily enhanced and the pungent odor of isobutanol or isoamyl alcohol tends to be augmented excessively. Therefore, it may well be said that beverages in which carbon dioxide gas is responsible for a pungent odor that has become more easily perceptible can preferably be treated by the present invention to suppress the pungent odor to a drinkable level. Carbon dioxide gas also helps increase the refreshing aftertaste of the beverage. Methods for adding carbon dioxide gas to the beverage are not particularly limited and examples include: dissolving carbon dioxide in the beverage under pressure; mixing carbon dioxide with the beverage in piping using a mixer such as a carbonator available from GEA Tuchen hagen Gmbh; spraying the beverage into a carbon dioxide filled tank so that the carbon dioxide is absorbed by the beverage; or mixing the beverage with carbonated water. For incorporating carbon dioxide gas in the beverage, a relatively high pressure is preferable because the refreshing sensation of the beverage is improved; for example, it is preferable to incorporate carbon dioxide gas in the beverage at a carbon dioxide gas pressure of atleast 1.5 kgf/cm2, more preferably 1.5 to 3.5 kgf/cm 2 , even more

2 2 preferably 1.5 to 3.0 kgf/cm2, and most preferably 1.8 to 3.0 kgf/cm2. It should be noted that in the present specification, "gas pressure" refers to the gas pressure for the case where the sample temperature is 20°C unless otherwise stated. The carbon dioxide gas pressure in the beverage can be measured using the gas volume analyzer GVA-500A from Kyoto Electronics Manufacturing Co., Ltd. With the sample temperature kept at 20°C, the air in the chamber of the above-mentioned gas volume analyzer is degassed (snifted) and after shaking, the carbon dioxide gas pressure is measured. As with ordinary beverages, various additives and the like may be further incorporated in the beverage of the present invention to an extent that will not interfere with the effect of the present invention. Examples of such various additives include sweeteners such as sugars and high intensity sweeteners, acidulants, flavoring agents, vitamins, pigments, antioxidants, emulsifiers, preservatives, extracts, dietary fibers, pH adjusters, thickening agents, and quality stabilizers. As regards the sugars, the sum of the contents of sucrose, glucose, and fructose in the beverage of the present invention is preferably no more than 1.7 g/100 ml. Within this range, the beverage is not only satisfactory in masking the pungent odor while reducing the oily smell but it also features a not too strong sweetness and can be drunk with a refreshing aftertaste. The above-noted sum of the contents of the sugars is more preferably 0.1 to 1.7 g/100 ml, even more preferably 0.2 to 1.5 g /100 ml. The sum of the contents of the above mentioned sugars is such that when only one of these three sugars is present in the beverage, the term refers to the content of that sugar; when two of these three sugars are present in the beverage, the term refers to the sum of the contents of the two sugars, and when all of these sugars are present in the beverage, the term refers to the sum of the contents of the three sugars. The content of each sugar can be measured by the biosensor method using a flow-injection apparatus (BF-7, Oji Scientific Instruments). The beverage of the present invention is then packed into a container after it is optionally sterilized and otherwise processed. The sterilized packed beverage can be produced by various methods such as, for example, a method wherein heat sterilization as with a hot water shower is performed after the beverage is filled into a container, or a method wherein the beverage is first sterilized and then filled into a container. The present invention can provide a beverage that contains isobutanol and/or isoamyl alcohol and which yet can be drunk with a refreshing sensation while keeping the profound flavor and complex taste of these alcohols; this type of beverage has never been accomplished by the prior art. Furthermore, the present invention can provide a beverage in which any pungent and oily odor is masked.

The present invention is explained below based on working examples, to which the present invention is in no way limited.

(Example 1) Samples were prepared as follows: material alcohol was added to water to make solutions with their alcohol content adjusted to 0 to 40 v/v%, and isobutanol, isoamyl alcohol, limonene, and/or nootkatone were then added in the amounts shown in the following table. For each sample, the pungent odor masking effect, oily smell, and overall rating were assessed by a panel of three trained experts according to the following criteria. The pungent odor masking effect: The degree by which the pungent odor of isobutanol and/or isoamyl alcohol could be masked by limonene and/or nootkatone was evaluated for each sample on a 5-point scale, with the case of containing isobutanol and/or isoamyl alcohol but not containing limonene and/or nootkatone being used as a control: 4, a strong masking effect is perceived; 3, a rather strong masking effect is perceived; 2, a masking effect is perceived; 1, a masking effect is scarcely perceived; 0, no masking effect is perceived. Oily smell: Each sample was assessed for the oily smell perceived when drunk, on a 5-point scale: 4, no oily smell is perceived; 3, an oily smell is scarcely perceived; 2, an oily smell is perceived; 1, a rather strong oily smell is perceived; 0, a strong oily smell is perceived. Overall rating: Each sample was assessed as to whether it would produce no perceivable pungent odor and could be drunk with a refreshing sensation, on a 5-point scale: 4, the sample was extremely favorable; 3, the sample was favorable; 2, the sample was acceptable; 1, the sample was not acceptable; 0, the sample was poor. It should be noted that in the following tables, "Alc." refers to the alcohol content, "Isobut." refers to the content of isobutanol, "Isoam." refers to the content of isoamyl alcohol, and "Total" refers to the sum of the contents of isobutanol and isoamyl alcohol.

[Table 1] Alc. Isobut. Isoam. Total Limonene Total/ Pungent Oily Overall Limonene odor smell rating masking effect v/v/. ppm ppm ppm ppmT Comparative sample 1 5 30 0 30 0.25 120 1 4 1 Comparative sample 2 5 0 30 30 0.25 120 1 4 1 Invention sample 1 5 30 30 60 0.25 240 3 4 3 Invention sample 2 5 100 0 100 0.25 400 2 4 2 Invention sample 3 5 200 0 200 0.25 800 3 4 3 Comparative sample 3 5 500 0 500 0.25 2000 1 4 1 Invention sample 4 5 0 100 100 0.25 400 3 4 3 Invention sample 5 5 0 200 200 0.25 800 4 4 4 Comparative sample 4 5 0 500 500 0.25 2000 1 4 1 Invention sample 6 5 100 50 150 0.25 600 3 4 3 Invention sample 7 5 50 100 150 0.25 600 3 4 3 Invention sample 8 5 100 100 200 0.25 800 3 4 3 Comparative sample 5 5 250 250 500 0.25 2000 1 4 1 Comparative sample 6 5 500 500 1000 0.25 4000 0 4 0 Comparative sample 7 5 30 0 30 0.5 60 1 4 1 Comparative sample 8 5 0 30 30 0.5 60 1 4 1 Invention sample 9 5 30 30 60 0.5 120 3 4 3 Invention sample 10 5 100 0 100 0.5 200 2 4 2 Invention sample 11 5 200 0 200 0.5 400 3 4 3 Invention sample 12 5 500 0 500 0.5 1000 2 4 2 Invention sample 13 5 0 100 100 0.5 200 3 4 3 Invention sample 14 5 0 200 200 0.5 400 4 4 4 Invention sample 15 5 0 500 500 0.5 1000 2 4 2 Invention sample 16 5 100 50 150 0.5 300 3 4 3 Invention sample 17 5 50 100 150 0.5 300 3 4 3 Invention sample 18 5 100 100 200 0.5 400 3 4 3 Invention sample 19 5 250 250 500 0.5 1000 2 4 2 Comparative sample 9 5 500 500 1000 0.5 2000 0 4 0 Comparative sample 10 5 30 0 30 0.8 38 1 4 1 Comparative sample 11 5 0 30 30 0.8 38 1 4 1 Invention sample 20 5 30 30 60 0.8 75 3 4 3 Invention sample 21 5 100 0 100 0.8 125 2 4 2 Invention sample 22 5 200 0 200 0.8 250 3 4 3 Invention sample 23 5 500 0 500 0.8 625 2 4 2 Invention sample 24 5 0 100 100 0.8 125 3 4 3 Invention sample 25 5 0 200 200 0.8 250 4 4 4 Invention sample 26 5 0 500 500 0.8 625 2 4 2 Invention sample 27 5 100 50 150 0.8 188 3 4 3 Invention sample 28 5 50 100 150 0.8 188 3 4 3 Invention sample 29 5 100 100 200 0.8 250 3 4 3 Invention sample 30 5 250 250 500 0.8 625 2 4 2 Comparative sample 12 5 500 500 1000 0.8 1250 0 4 0 As understood from the Example, when ((isobutanol + isoamyl alcohol)/ limonene) (ratio by weight) was 100 to 800, the profound flavor and complex taste of the fusel oils were maintained while their unpleasant odor was sufficiently masked to provide a condition that would assure an especially fine and refreshing sensation.

[Table 2] Alc. Isobut. Isoam. Total Limonene Total/ Pungent Oily Overall Limonene odor smell rating masking effect v/v/. ppm ppm ppm ppmT Comparative sample 13 5 30 0 30 1.6 19 1 4 1 Comparative sample 14 5 0 30 30 1.6 19 1 4 1 Invention sample 31 5 30 30 60 1.6 38 3 4 3 Invention sample 32 5 100 0 100 1.6 63 2 4 2 Invention sample 33 5 200 0 200 1.6 125 3 4 3 Invention sample 34 5 500 0 500 1.6 313 2 4 2 Invention sample 35 5 0 100 100 1.6 63 3 4 3 Invention sample 36 5 0 200 200 1.6 125 4 4 4 Invention sample 37 5 0 500 500 1.6 313 2 4 2 Invention sample 38 5 100 50 150 1.6 94 3 4 3 Invention sample 39 5 50 100 150 1.6 94 3 4 3 Invention sample 40 5 100 100 200 1.6 125 3 4 3 Invention sample 41 5 250 250 500 1.6 313 2 4 2 Invention sample 42 5 500 500 1000 1.6 625 2 4 2 Comparative sample 15 5 30 0 30 2.0 15 1 4 1 Comparative sample 16 5 0 30 30 2.0 15 1 4 1 Comparative sample 17 5 30 30 60 2.0 30 3 2 1 Comparative sample 18 5 100 0 100 2.0 50 2 2 0 Comparative sample 19 5 200 0 200 2.0 100 3 2 1 Comparative sample 20 5 500 0 500 2.0 250 2 1 0 Comparative sample 21 5 0 100 100 2.0 50 3 2 1 Comparative sample 22 5 0 200 200 2.0 100 3 2 1 Comparative sample 23 5 0 500 500 2.0 250 2 1 0 Comparative sample 24 5 100 50 150 2.0 75 3 2 1 Comparative sample 25 5 50 100 150 2.0 75 3 2 1 Comparative sample 26 5 100 100 200 2.0 100 3 2 1 Comparative sample 27 5 250 250 500 2.0 250 2 1 0 Comparative sample 28 5 500 500 1000 2.0 500 2 1 0 Invention sample 43 0 100 100 200 0.8 250 3 4 3 Invention sample 44 3 100 100 200 0.8 250 4 4 4 Invention sample 45 10 100 100 200 0.8 250 4 4 4 Invention sample 46 25 100 100 200 0.8 250 4 4 4 Invention sample 47 30 100 100 200 0.8 250 4 3 3 Invention sample 48 40 100 100 200 0.8 250 3 3 2 As understood from the Example, when isobutanol + isoamyl alcohol was greater than 60 ppm, the increasing content of limonene rendered its oily smell so prominent that the sample could not be drunk with a refreshing sensation. When ((isobutanol + isoamyl alcohol) / limonene) (ratio by weight) was 100 to 800, the profound flavor and complex taste of the fusel oils were maintained while their unpleasant odor was sufficiently masked to provide a condition that would assure an especially fine and refreshing sensation.

[Table 3] Nootkatone Alc. Gas Isobut. Isoam. Total Nootkatone Total/ Pungent Oily Overall Comments pressure Nootkatone odor smell rating masking effect 2 ppm ppm| v/v%| kgf/cm ppm ppm Comparative 5.0 1.5 30 30 60 0.01 6000 0 4 0 There was not a sample 29 substantial masking effect and a pungent odor was sensed. Invention 0.0 1.5 30 30 60 0.05 1200 3 4 3 A masking effect was sample 49 perceived and the sample having a refreshing sensation was easy to drink. Invention 3.0 2.0 100 100 200 0.08 2500 3.5 4 4 A strong masking effect sample 50 was perceived and a refreshing taste was sensed. Invention 5.0 2.0 100 100 200 0.10 2000 4 4 4 A strong masking effect sample 51 was perceived and a refreshing taste was sensed. Comparative 5.0 2.0 200 200 400 0.10 4000 0 4 0 The unpleasant and sample 30 pungent odor of the fusel oils was perceived. Invention 9.0 2.0 100 50 150 0.30 500 4 4 4 A strong masking effect sample 60 was perceived and a refreshing taste was sensed. Invention 10.0 0.0 100 50 150 0.30 500 3.5 4 3.5 The absence of carbon sample 52 dioxide gas was responsible for a somewhat weak masking effect. Invention 30.0 0.0 100 100 200 1.60 125 4 3 3 Having only slightly sample 53 perceivable pungent and unpleasant odor, the sample could be drunk with a refreshing sensation. Invention 40.0 0.0 500 500 1000 1.60 625 4 3 3 Having only slightly sample 54 perceivable pungent and unpleasant odor, the sample could be drunk with a refreshing sensation. Comparative 5.0 2.0 500 500 1000 2.00 500 4 1 1 Because of the fusel sample 31 oils and nootkatone, a somewhat prominent oily smell was perceived. As understood from the results above, when the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone was 500 to 2500, the profound flavor and complex taste of the fusel oils were remained while their unpleasant odor was sufficiently masked to provide a condition that would assure an especially fine, refreshing sensation. It was also found that even when limonene and nootkatone were used in combination, the masking effect was still functional. Although Invention samples 43 and 49 were beverages with an alcohol content of 0 v/v%, i.e. non-alcoholic beverages, the same effect was achieved. (Example 2) Samples were prepared as follows: water, material alcohol, and carbonated water were mixed to make solutions with an alcohol content of 5 v/v% and with their carbon dioxide gas pressure being adjusted to the values indicated in Table 4 below; to the resulting solutions, isobutanol, isoamyl alcohol, and limonene were added in the amounts also indicated in Table 4. As in Example 1, each sample was assessed for the pungent odor masking effect, oily smell, and overall rating.

[Table 4] Gas Isobut. Isoam. Total Limonene Total/ Pungent Oily Overall Comments pressure Limonene odor smell rating masking effect kgf/cm 2 ppm ppm ppm ppm Invention 0.0 100 100 200 1.0 200.0 3 4 3 Having only slightly sample perceivable pungent and 55 unpleasant odor, the sample could be drunk with a refreshing sensation. Invention 1.5 100 100 200 1.0 200.0 4 4 4 Because of carbon sample dioxide gas, the masking 56 effectwasenhanced to provide an increased refreshing feel. Invention 2.0 100 100 200 1.0 200.0 4 4 4 Because of carbon sample dioxide gas, the masking 57 effectwasenhanced to provide an increased refreshing feel. Invention 3.0 100 100 200 1.0 200.0 4 4 4 Because of carbon sample dioxide gas, the masking 58 effectwasenhanced to provide an increased refreshing feel. Invention 3.5 100 100 200 1.0 200.0 3 4 3 Because of carbon sample dioxide gas, a stronger 59 pungentodorwas perceived but the sample could be drunk with a refreshing sensation. As understood from the Example, when the carbon dioxide gas pressure was equal to or greater than 1.5 kgf/cm2 , the masking effect was further enhanced. However, it was verified that when the carbon dioxide gas pressure was equal to or greater than 2 3.5 kgf/cm2, the masking effect became rather weak. (Example 3) Samples were prepared as follows: material alcohol was added to water to make solutions with their alcohol content adjusted to 5 v/v%, and to the resulting solutions, isobutanol, isoamyl alcohol, and limonene were added in the amounts shown in the following table, followed by further addition of high-fructose corn syrup. The "Total sugar" cited in the following table refers to the total amount of sucrose, glucose, and fructose. Each sample was evaluated for the pungent odor masking effect, oily smell, and sweetness by a panel consisting of three trained experts who also performed an overall rating assessment. Criteria for evaluating the pungent odor masking effect and oily smell were the same as those in Example 1. Criteria for sweetness evaluation and overall rating assessment are described below. The results are shown in Table 5. <Sweetness> 4: not sweet, with a strong, fine refreshing flavor perceived. 3: not sweet, can be drunk with a refreshing sensation that that persists until it becomes an aftertaste. 2: feels slightly sweet but can be drunk with a refreshing sensation that persists until it becomes an aftertaste. 1: feels slightly syrupy and does not provide a refreshing sensation. 0: quite syrupy, with an unpleasant aftertaste. <Overall rating> 5: extremely favorable 4: more favorable 3: favorable 2: acceptable 1: not acceptable 0: poor

[Table 5] Total Isobut. Isoam. Total Limonene Total/ Pungent Oily Sweetness Overall Comments sugar Limonene odor smell rating masking effect g109ml ppm ppm ppm ppm Invention 0 250 250 500 0.8 625.00 2 4 3 2 Having a masked sample pungent odor, the 30 sample could be drunk with a refreshing sensation. Invention 0.1 250 250 500 0.8 625.00 3 4 3 4 With a more sample perceivable masking 60 effect, the sample had a refreshing taste. Invention 0.2 250 250 500 0.8 625.00 4 4 4 5 An even stronger sample masking effect was 61 perceived, with the result that a strong fine, refreshing flavor was perceived. Invention 1.5 250 250 500 0.8 625.00 4 4 4 5 An even stronger sample masking effect was 62 perceived, with the result that a strong fine, refreshing flavor was perceived. Invention 1.7 250 250 500 0.8 625.00 4 4 3 4 With a strongly sample perceivable masking 63 effect, the sample was not sweet and could be drunk with a refreshing sensation that persisted until it became an aftertaste. Invention 2.0 250 250 500 0.8 625.00 4 4 2 2 A perceivable sample masking effect was 64 accompanied bya slightly sensed sweetness. Invention 8.0 250 250 500 0.8 625.00 4 4 2 2 A perceivable sample masking effect was 65 accompanied bya slightly sensed I__ I I I I sweetness. When the sugars were incorporated as additional ingredients in the specified amounts, particularly marked effects were obtained in terms of the pungent odor masking effect, oily smell, and sweetness.

- 14a

It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or any other country. In the claims which follow and in the preceding description of the invention, except where the context requires otherwise due to express language or necessary implication, the word "comprise" or variations such as "comprises" or "comprising" is used in an inclusive sense, i.e. to specify the presence of the stated features but not to preclude the presence or addition of further features in various embodiments of the invention.

13418201_1 (GHMatters) P109255.AU

Claims (5)

Claims:

1. A packaged beverage containing: (A) isobutanol and/or isoamyl alcohol; and (B) limonene and/or nootkatone, wherein the sum of the contents of isobutanol and isoamyl alcohol is 60 to 1000 ppm, the packaged beverage contains carbon dioxide gas, and the pressure of the carbon dioxide gas is in the range of 1.5 kgf/cm 2 to 3.0 kgf/cm 2

, and the packaged beverage satisfies either or both of the following conditions (i) and (ii): i) when the beverage contains limonene, the content of limonene is 0.25 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of limonene is 30 to 1000; and ii) when the beverage contains nootkatone, the content of nootkatone is 0.05 to 1.60 ppm, and the ratio of the sum of the contents of isobutanol and isoamyl alcohol to the content of nootkatone is 100 to 2500.

2. The packaged beverage according to claim 1, wherein the alcohol content is 0 to 40 v/v%.

3. The packaged beverage according to claim 1, wherein the alcohol content is 3 to 9 v/v%.

4. The packaged beverage according to any one of claims 1-3, wherein the fruit juice percentage of the beverage is 0.1 w/w% to 40 w/w%.

5. The packaged beverage according to any one of claims 1-4, wherein the sum of the contents of sucrose, glucose, and fructose is no more than 1.7 g/100 ml.

13418201_1 (GHMatters) P109255.AU