JP6948212B2 - Packaged coffee beverage containing chlorogenic acid lactones - Google Patents

Description

The present invention relates to a packaged coffee beverage. More specifically, the present invention relates to a packaged coffee beverage having an improved aftertaste that occurs over time after opening, a method for producing the packaged coffee beverage, and the like.

Coffee beverages are widely loved as a luxury item, and their demand is increasing and their needs are diversifying. For example, while there is a need for a coffee beverage having a bitterness or a profound taste peculiar to coffee, there is also a need for a coffee beverage having a suppressed bitterness peculiar to coffee and a good aftertaste. In addition, there are a wide variety of coffee beverage products, from refrigerated types to products that can be stored at room temperature. Under these circumstances, consumers can select coffee in a commercial form according to their taste and consumption mode such as drinking place.

Unlike regular coffee, packaged coffee beverages, especially refillable packaged beverages, are widely used to drink coffee beverages while walking, or to drink coffee beverages little by little over a long period of time during work or breaks. Be done. However, after a long time has passed since the cap was opened, the aftertaste was deteriorated due to the change in the components due to the effects of oxidation and volatilization. Although changes in flavor due to the effects of oxidation during storage have been taken into consideration, the idea of producing packaged coffee beverages in consideration of the increase in bad aftertaste due to changes over time after opening is not known.

It has been reported that some aroma components of coffee beverages decrease with the passage of time after production, and the aroma balance of coffee beverages changes (Non-Patent Document 1). Attempts have also been reported to suppress changes in the aroma balance of coffee beverages over time by adding them. For example, in Patent Document 1, by controlling the content mass ratio of pyrazines and guaiacols in a coffee beverage within a specific range, a coffee extract having a rich sweet aroma and a good aftertaste can be obtained. In Cited Document 2, the ratio of the highly volatile coffee aroma compound (methanethiol, etc.) to the low volatile coffee aroma compound (guaiacol, etc.) is increased to increase the ratio of the coffee beverage to the opening and consumption of the coffee beverage. It has been reported that the aroma of coffee is easily perceived. Further, Patent Document 3 discloses a method for producing a roasted bean coffee extract in which chlorogenic acid lactones are selectively reduced to suppress bitterness.

Japanese Unexamined Patent Publication No. 2011-125289 Special Table 2016-540512 Japanese Unexamined Patent Publication No. 2013-046641

European Food Research and Technology, 211, 272-276 (2000)

However, neither document describes taking into account the increase in aftertaste due to aging of the packaged coffee beverage. An object of the present invention is to provide a packaged coffee beverage in which the bad aftertaste that occurs over time after opening is improved.

As a result of diligent studies to solve the above problems, the present inventors have determined that the content of chlorogenic acid lactones (b) (mg / L) and the content of guaiacol (a) (μg / L). By adjusting the contents of (b) and (a) in the coffee beverage so that the content ratio [(b) / (a)] is within a specific range, the time has passed since the bottled coffee beverage was opened. We have found that it is possible to improve the bad aftertaste that occurs, and have completed the present invention.

That is, the present invention relates to the following, but is not limited thereto.
(1) Contains chlorogenic acid lactones (b) and guaiacol (a), and satisfies [(b) content (mg / L) / (a) content (μg / L)]> 0.020. , Bottling coffee beverages.
(2) Further, it contains phenol (c) and satisfies [(b) content (mg / L) / {(a) + (c)} content (μg / L)]> 0.0080. , (1). The packaged coffee beverage according to (1).
(3) Further, p-ethylphenol (d), p-cresol (e) and 2-acetylpyrrole (f) are contained, and the content of [(b) (mg / L) / {(a) + ( c) + (d) + (e) + (f)} content (μg / L)] ≧ 0.0050, according to (2).
(4) The packaged coffee beverage according to any one of (1) to (3), wherein the content of guaiacol (a) is 100 μg / L to 500 μg / L.
(5) The packaged coffee beverage according to any one of (1) to (4), which is black coffee.
(6) The packaged coffee beverage according to any one of (1) to (5), wherein the Brix value of the beverage is 0.4 or more.
(7) The containerized coffee beverage according to any one of (1) to (6), which is filled in a container with a recapable lid.
(8) A method for producing a packaged coffee beverage.
(I) [Content of chlorogenic acid lactones (b) (mg / L) / Content of guaiacol (a) (μg / L)]> 0.020 so as to satisfy (a) and (b). The process of adjusting the content and
(Ii) Container filling process,
The production method.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a packaged coffee beverage in which the bad aftertaste that occurs over time after opening is improved.

FIG. 1 shows LC-MS chromatograms of standard chlorogenic acid lactones. FIG. 2 shows an LC-MS chromatogram of chlorogenic acid lactones in a sample coffee beverage (Example 1).

1. 1. Packaged Coffee Beverage The packaged coffee beverage of the present invention contains chlorogenic acid lactones (b) and guaiacol (a), and contains [(b) (mg / L) / (a) (μg). / L)]> 0.020. This makes it possible to improve the bad aftertaste that occurs over time after opening the bottled coffee beverage. In addition, in this specification, "bad aftertaste" means that the bitterness of coffee is persistently left on the tongue after drinking, and it is also referred to as postponement. On the other hand, even if it is the bitterness of coffee, the sharp bitterness is different from the "bad aftertaste".

1-1. Chlorogenic Acid Lactones Chlorogenic acid lactones are a general term for compounds in which a cyclic structure is formed in a part of quinic acid residues of chlorogenic acids, and 5-cafe oil-1,3-quinolactone, 3-. Café oil-1,5-quinolactone, 4-cafe oil-1,3-quinolactone, 4-cafe oil-1,5-quinolactone, 5-cafe oil-1,4-quinolactone and the like are included. The content of chlorogenic acid lactones of the present invention refers to a value measured by the method described in Examples. Chlorogenic acid lactones are components that contribute to the bitterness of coffee, are hardly contained in green coffee beans, and are known to be produced from chlorogenic acids by roasting. In this specification, chlorogenic acid lactones may be represented by (b).

The content of chlorogenic acid lactones in the coffee beverage of the present invention is not particularly limited, but is preferably 3.0 mg / L to 15.0 mg / L, more preferably 4.0 mg / L from the viewpoint of improving the bad aftertaste. It is L to 13.5 mg / L, more preferably 4.5 mg / L to 12.5 mg / L. In the present specification, the content of chlorogenic acid lactones is 5-cafe oil-1,3-quinolactone, 3-cafe oil-1,5-quinolactone, 4-cafe oil-1,3-quinolactone, 4-. It means the total content of caffe oil-1,5-quinolactone and 5-cafe oil-1,4-quinolactone.

1-2. Guaiacol In the present invention, guaiacol is a component that contributes to the lingering bitterness peculiar to coffee. In this specification, guaiacol may be referred to as (a).

The coffee beverage of the present invention contains guaiacol, but the content thereof is not particularly limited. For example, the content of guaiacol in the coffee beverage of the present invention is preferably 100 μg / L to 500 μg / L, more preferably 150 μg / L to 470 μg / L, and even more preferably 210 μg / L to 370 μg / L. If the content of guaiacol in the coffee beverage is high, the effect of improving the bad aftertaste that occurs over time after opening the bottled coffee beverage may not be sufficiently obtained.

The content of guaiacol can be measured by the GC-MS method.
1-3. Content ratio of chlorogenic acid lactones and guaiacol The coffee beverage of the present invention has the content of chlorogenic acid lactones (b) and guaiacol (from the viewpoint of further improving the bad aftertaste that occurs over time after opening the cap. The content ratio [(b) / (a)] to the content of a) is [(b) / (a)]> 0.020, preferably 0.100> [(b) / (a). )]> 0.020, more preferably 0.050> [(b) / (a)]> 0.020.

1-4. Phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole In the present invention, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole are all components that contribute to the lingering bitterness peculiar to coffee. be. The coffee beverage of the present invention is further selected from the group consisting of phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole from the viewpoint of effectively suppressing the bad aftertaste that occurs over time after opening. It is also possible to adjust the content of one or more components. In this specification, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole may be referred to as (c), (d), (e) and (f), respectively.

The content of phenol in the coffee beverage of the present invention is not particularly limited, but is preferably 50 μg / L to 700 μg / L, more preferably 100 μg / L to 500 μg / L, and even more preferably 120 μg / L to 370 μg / L. .. The content of p-ethylphenol in the coffee beverage of the present invention is preferably 0.5 μg / L to 15.0 μg / L, more preferably 1.0 μg / L to 10.0 μg / L, and even more preferably 1.0 μg / L to 10.0 μg / L. It is 2.0 μg / L to 6.5 μg / L. The content of p-cresol in the coffee beverage of the present invention is preferably 3.0 μg / L to 19.0 μg / L, more preferably 5.0 μg / L to 16.0 μg / L, and even more preferably 7. It is 0.0 μg / L to 13.0 μg / L. The content of 2-acetylpyrrole in the coffee beverage of the present invention is preferably 200 μg / L to 1450 μg / L, more preferably 400 μg / L to 1250 μg / L, and further preferably 600 μg / L to 1100 μg / L. be.

The contents of phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole can be measured by the GC-MS method, respectively.
1-5. Ratio of chlorogenic acid lactones to the total content of guaiacol and phenol The coffee beverage of the present invention has chlorogenic acid lactones (b) from the viewpoint of further improving the bad aftertaste that occurs over time after opening. The ratio [(b) / {(a) + (c)}] of the content of guaiacol (a) and the total content of phenol (c) is [(b) / {(a) + ( c)}]> 0.0080, more preferably 0.050> [(b) / {(a) + (c)}]> 0.008, 0.025> [( b) / {(a) + (c)}]> 0.012 is even more preferable.

1-6. Ratio of chlorogenic acid lactones to the total content of guaiacol, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole The coffee beverage of the present invention has a bad aftertaste that occurs over time after opening. From the viewpoint of more effective improvement, the content of chlorogenic acid lactones (b) and guaiacol (a), phenol (c), p-ethylphenol (d), p-cresol (e) and 2-acetyl The ratio [(b) / {(a) + (c) + (d) + (e) + (f)}] to the total content of pyrrol (f) is [(b) / {(a)). + (C) + (d) + (e) + (f)}] ≧ 0.0050, preferably 0.050> [(b) / {(a) + (c) + (d) + (E) + (f)}] ≧ 0.0050, more preferably 0.010> [(b) / {(a) + (c) + (d) + (e) + (f)} ] ≧ 0.0050 is even more preferred.

1-7. Coffee Beverages As used herein, the term "coffee beverages" refers to beverage products that have been heat-sterilized using coffee as a raw material. The type of product is not particularly limited, but mainly includes "coffee", "coffee drink", and "soft drink with coffee", which are the definitions of the "fair competition rules for labeling of coffee drinks, etc." approved in 1977. Be done. In addition, even among beverages made from coffee, those with a milk solid content of 3.0% by weight or more are treated as "milk beverages" under the application of the "Fair Competition Code for Labeling of Drinking Milk". Also referred to as the coffee beverage in the present invention. Here, the coffee content refers to one containing a component derived from coffee beans, and examples thereof include a coffee extract, that is, a solution obtained by extracting roasted and crushed coffee beans with water, warm water, or the like. .. Further, a solution obtained by adjusting an appropriate amount of coffee extract obtained by concentrating the coffee extract, instant coffee obtained by drying the coffee extract, or the like with water or warm water is also mentioned as the coffee content.

The cultivated tree species of coffee beans used in the coffee beverage of the present invention is not particularly limited, and examples thereof include arabica species, Robusta species, and Coffea liberica species, but it is preferable to use arabica species. The variety name is not particularly limited, and examples thereof include Mocha, Brazil, Colombia, Guatemala, Blue Mountain, Kona, Mandelin, and Kilimanjaro. One type of coffee beans may be used, or a plurality of types may be blended and used. Regarding the roasting method of coffee beans, the roasting temperature and the roasting environment are not particularly limited, and a normal method can be adopted. Furthermore, there are no restrictions on the extraction method from the roasted coffee beans. For example, water or warm water (0 to 200 ° C.) is used from a crushed product obtained by coarsely grinding roasted coffee beans, medium grinding, fine grinding, or the like. There is a method of extracting. Extraction methods include drip type, siphon type, boiling type, jet type, continuous type and the like.

Milk such as milk, milk and dairy products may be added to the coffee beverage of the present invention as needed, but black coffee containing no milk is preferable.
Further, the coffee beverage of the present invention is a packaged coffee beverage filled in an arbitrary container. The container filled with the coffee beverage of the present invention may be appropriately selected according to the sterilization method and storage method, and any commonly used container such as an aluminum can, a steel can, a PET bottle, a glass bottle, or a paper container is used. be able to. Further, since the coffee beverage of the present invention is suitable for drinking over a long period of time, a container with a recapable lid, that is, a bottle can or a PET bottle is preferable. The capacity of the coffee beverage of the present invention is not particularly limited, but is preferably 160 to 600 g, and 250 g or more is preferable in terms of drinking over a long period of time. When the coffee beverage of the present invention is packed in a container, either a hot pack filling method or an aseptic filling method can be used, but it is preferable to use the aseptic filling method. The hot pack filling method generally refers to a method in which a beverage heated to 60 ° C. or higher is filled in a container and then immediately sealed. The aseptic filling device generally refers to a device that fills a sterilized container with contents sterilized at a high temperature for a short time in a sterile environment and seals the contents.

The method for heat sterilization of the coffee beverage of the present invention is not particularly limited. For example, heat sterilization can be performed in accordance with local regulations (Food Sanitation Law in Japan). Specifically, a method of sterilizing at a high temperature for a short time and then filling the storage container that has been sterilized under sterile conditions (UHT sterilization method), and a method of filling the preparation solution in a storage container such as a can and then performing retort treatment. Examples include the retort sterilization method to be performed. In the case of the UHT sterilization method, the conditions are usually about 1 to 120 seconds at 120 to 150 ° C., preferably about 30 to 120 seconds at 130 to 145 ° C., and in the case of the retort sterilization method, it is usually 10 to 30 at 110 to 130 ° C. The condition is about minutes, preferably about 120 to 125 ° C. for about 10 to 20 minutes.

1-8. Brix value The Brix value is the refractive index measured at 20 ° C using a sugar content meter or refractometer, and is converted to the mass / mass percent of the sucrose solution based on the conversion table of ICUMSA (International Sugar Analysis Method Unification Committee). It is a converted value and represents the soluble solid content content in the beverage. The unit may be expressed as "Bx", "%" or "degree". If the Brix value of the beverage is low, the content of soluble solids in the beverage including sugar is low.

The Brix value of the coffee beverage of the present invention is not particularly limited, but is preferably 0.4 or more, more preferably 0.4 to 3.0, and more preferably 0.4 to 1.8. preferable.

1-9. Other Ingredients In the coffee beverage of the present invention, in addition to the above ingredients, sweeteners (saccharin, isomerized sugar, glucose, fructose, lactose, malt sugar, xylitol, isomerized lactose, fructo-oligo) are used as long as the effects of the present invention are not impaired. Sugar, maltooligosaccharide, high fructose corn syrup, galactooligosaccharide, coupling sugar, palatinose, martitol, sorbitol, erythritol, xylitol, lactitol, palatinit, reduced starch saccharified product, stevia, glycyrrhizin, taumatin, monerin, aspartame, ariteme, saccharin, Aspartame K, sucralose, zultin, etc.), antioxidants (vitamin C, sodium erythorbinate, etc.), emulsifiers (saccharin fatty acid ester, sorbitan fatty acid ester, polyglycerin fatty acid ester, etc.), casein Na, fragrance (coffee flavor, milk flavor, etc.) Etc.) etc. can be appropriately blended. In the coffee beverage of the present invention, it is particularly preferable to add a flavor from the viewpoint of adjusting the content ratio of chlorogenic acid lactones and guaiacol to a specific range. Moreover, since the effect of the present invention may be impaired by the sweetener in the beverage of the present invention, a coffee beverage containing no sweetener is preferable.

1-10. pH
The coffee beverage of the present invention preferably has a pH within a predetermined range. A general pH adjuster can be used to adjust the pH, and such pH adjusters include bases such as sodium hydroxide and potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, potassium hydrogencarbonate, and carbonic acid. Sodium or potassium salts of organic acids such as potassium, disodium hydrogen phosphate, sodium citrate, potassium citrate, sodium acetate, potassium acetate, sodium L-ascorbate, and other pH regulators that can be used under food hygiene law. Alternatively, an acidity agent may be mentioned. It is also possible to adjust the pH to a predetermined value by mixing coffee extracts having different pH.

In the invention according to the present embodiment, the pH is preferably in the range of 4.0 to 7.0, more preferably in the range of 5.0 to 6.5, and even more preferably in the range of 5.2 to 6.2.
2. Method for Producing a Packaged Coffee Beverage In some embodiments, the present invention is a method for producing a packaged coffee beverage. More specifically, one aspect of the present invention is a method for producing a packaged coffee beverage, wherein (i) [content of chlorogenic acid lactones (b) (mg / L) / content of guaiacol (a)). (Μg / L)] The production method includes a step of adjusting the contents of (a) and (b) so as to satisfy> 0.020, and (ii) a step of bottling.

The method further comprises one or more components selected from the group consisting of phenol (c), p-ethylphenol (d), p-cresol (e) and 2-acetylpyrrole (f), and the content thereof. It is also possible to include a step of adjusting. Further, a step of adjusting the ratio between the content of (b) and the content of (a) + (c), and the content of (b) and (a) + (c) + (d) + ( It is also possible to include a step of adjusting the ratio with the content of e) + (f). Further, the method can also include a step of blending components that can be used in ordinary coffee beverages, a step of adjusting pH, and a step of heat sterilization treatment.

In the above method, each of the above steps may be performed in any order, and the content in the finally obtained coffee beverage may be within the required range.
The varieties and production areas of coffee beverages and coffee beans used as raw materials are as described above. Further, the content range of (b) to (f), the range of the ratio of the content of (b) to the content of (a), the content of (b) and the content of (a) + (c). Range of ratio to amount, range of ratio of content of (b) to content of (a) + (c) + (d) + (e) + (f), range of pH, and other components Etc. are also as described above. Further, the method for measuring various components is also as described above.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.
1. 1. Production of sample coffee beverage In this example, sample beverages having different contents of guaiacol, chlorogenic acid lactones, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole (Examples 1 to 7 and Comparative Examples 1 to 1). 3) was prepared. Specific preparation methods for each sample beverage are described below. Standard products of each component were also prepared and added as needed.
<Example 1>
Coffee beans roasted in medium roast (Guatemala species: L value 20) were crushed, and hot water with a mass 9 times the amount of coffee beans was used as the extraction hot water, and extraction was performed at 50 ° C. with an extractor. .. In addition, a steaming time of 3 minutes was provided in the middle of the extraction step. Then, the extraction was completed when the amount of hot water to be collected became about three times the mass of the amount of coffee beans. Then, the extract was centrifuged and membrane-filtered. Then, the obtained extract was diluted about 3 times, and baking soda was further added to obtain a formulation for Example 1. The base beverage was filled in a can and retort sterilized at F0 = 4 or higher to obtain the coffee beverage of Example 1 .
<Example 2>
The formulation for Example 1 was diluted 10/12 times to prepare the formulation for Example 2. Then, the preparation liquid for Example 2 was filled in a bottle can having a capacity of 400 g, and retort sterilization was carried out at F0 = 4 or more to obtain a coffee beverage of Example 2.
<Example 3, Example 4, Comparative Example 2>
Guaiacol was blended with the preparation of Example 2 so as to have a predetermined content to prepare preparations for Examples 3 and 4 and Comparative Example 2. Then, the preparations for Examples 3 and 4 and Comparative Example 2 were filled in a can, and retort sterilization was carried out at F0 = 4 or higher to obtain coffee beverages of Examples 3 and 4 and Comparative Example 2.
<Example 5>
The formulation for Example 3 was diluted 7/10 times to prepare the formulation for Example 5. Then, the preparation liquid for Example 5 was filled in a can, and retort sterilization was carried out at F0 = 4 or more to obtain a coffee beverage of Example 5.
<Example 6>
Guaiacol was blended with the formulation for Example 5 so as to have a predetermined content to prepare a formulation for Example 6. Then, the preparation liquid for Example 6 was filled in a can, and retort sterilization was carried out at F0 = 4 or more to obtain the coffee beverage of Example 6.
<Example 7>
The formulation for Example 6 was diluted 4.7 / 8 times to prepare the formulation for Example 7. Then, the preparation liquid for Example 7 was filled in a can, and retort sterilization was carried out at F0 = 4 or more to obtain a coffee beverage of Example 7.
<Comparative example 3>
Guaiacol was added to the formulation for Example 7 so as to have a predetermined content to prepare a formulation for Comparative Example 3. Then, the preparation liquid for Comparative Example 3 was filled in a can, and retort sterilization was carried out at F0 = 4 or higher to obtain a coffee beverage of Comparative Example 3.
<Comparative example 1>
Coffee beans roasted in ultra-deep roast (Guatemala species: L value 16) are crushed, and 9 times the mass of water as the amount of coffee beans is used as extraction water, and extraction is performed at a low temperature of 20 ° C with an extractor. went. In addition, a steaming time of 3 minutes was provided in the middle of the extraction step. Then, the extraction was completed when the amount of hot water to be collected became about three times the mass of the amount of coffee beans. Then, the obtained extract was diluted about 3 times, and baking soda was further added to obtain a mixed solution. The preparation was filled in a can and retort sterilized at F0 = 4 or higher to obtain a coffee beverage of Comparative Example 1.

2. Measurement of chlorogenic acid lactones, guaiacol, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole content Samples of packaged coffee beverage after retort sterilization prepared in 1 above (Examples 1 to 7 and Comparative Examples) The caps 1 to 3) were opened, and the contents of chlorogenic acid lactones, guaiacol, phenol, p-ethylphenol, p-cresol and 2-acetylpyrrole in each coffee beverage were measured under the following analytical conditions. In addition, the content of each component in commercially available canned coffees 1 to 3 (commercial product 1: Coca-Cola emerald mountain coffee, commercial product 2: Wonda coffee, and commercial product 3: KIRIN Fire smoked coffee Black) was also analyzed in the same manner. The results are shown in Table 1.
<Analytical conditions for chlorogenic acid lactones (LC / MS)>
Chlorogenic acid lactones were analyzed using LC / MS.
(LC separation condition)
HPLC device: Agilent 1290 series (manufactured by Agilent Technologies)
Liquid transfer pump: G4220A
Autosampler: G4226A (with thermostat G1330B)
Column oven: G1316C
DAD detector: G4212A
Column: Cortecs UPLC T3 (particle size 1.6 μm, inner diameter 2.1 mm × 150 mm, manufactured by Waters)
Mobile phase A: 0.1% aqueous solution of formic acid Mobile phase B: Acetonitrile Flow rate: 0.4 mL / min
Concentration gradient conditions: 0.0 to 2.0 minutes (10% B) → 8.0 minutes (25% B) → 8.5 to 10.0 minutes (100% B), equilibration by initial mobile phase 5. 0 minute Column temperature: 40 ° C
Sample injection: Injection volume 2.0 μL
Sample introduction into mass spectrometer: 1.35 to 8.49 minutes (mass spectrometry conditions)
Mass spectrometer: Q Active (manufactured by Thermo Fisher Scientific)
Ionization method: HESI, negative mode Ionization section Conditions:
Sheath gas flow rate: 50
Aux gas flow rate: 10
Sweep gas flow rate: 0
SpRay voltage: 2.50kV
Capillary temper: 350 ° C
Aux gas heater emp: 300 ° C
Detection condition:
Resolution: 140000
AGC Target: 1e6
Maximum IT: 100ms
Scan Range: 200 to 500 m / z
(Preparation of standard products)
Standard products of chlorogenic acid lactones are Tetrahedron Letter. , Vol. It was synthesized with reference to the method described in 52, 2011, 7175-7177. The method is as follows. Chlorogenic acid (manufactured by Sigma Aldrich, 0.9 g) and p-toluenesulfonic acid (manufactured by Nakaraitesk, 0.05 g) were measured in a reflux flask, and anhydrous N, N-dimethylformamide (manufactured by Wako Pure Chemical Industries, Ltd., 5 mL) and toluene (manufactured by Nakaraitesk, 18 mL) were added, shaken well, and heated under reflux with a Dean-Stark apparatus for 12 hours. This was cooled to room temperature, the solvent was distilled off with a rotary evaporator, and the residue was heated under reflux with ethyl acetate (manufactured by Wako Pure Chemical Industries, Ltd., 20 mL) for 4 hours. The obtained liquid was distilled off with a rotary evaporator, and the residue was dissolved in methanol for HPLC. A 1/20 amount of this solution was taken and passed through an anion exchange column (Sep-Pak Vac QMA 6 cc, manufactured by Waters) previously equilibrated with methanol.

When this was analyzed using the above LC separation conditions and mass spectrometric conditions, as shown in FIG. 1, 5.4 minutes to 6.6 minutes in an extracted ion chromatogram of 335.07556 to 335.07892 m / z. Multiple peaks were detected in. These components were considered to be chlorogenic acid lactones based on their precise mass and references (Eur. Food Res. Technol., Vol. 222, 2006, 492-508). Since both chlorogenic acid and chlorogenic acid lactones have caffeic acid in the molecule, they have the same molar extinction coefficient at an absorbance of 280 nm. Therefore, the peak area was compared with the chlorogenic acid standard solution having a known concentration at an absorbance of 280 nm (DAD detector G4212A) under the same analytical conditions, and the content of chlorogenic acid lactones in the obtained preparation solution was calculated. That is, in a chromatogram having an absorbance of 280 nm, a peak area (eluting time of about 3.2 minutes) obtained by analysis of a 1 mmol / L chlorogenic acid standard solution and a peak area obtained by analysis of a solution containing chlorogenic acid lactones (election time: about 3.2 minutes). If the dissolution time (5.4 to 6.6 minutes) is the same, it means that the concentration of chlorogenic acid lactones is 1 mmol / L.
(Sample preparation)
Analytical samples were prepared by the following methods. First, the coffee sample was diluted exactly 10-fold with distilled water for chromatography. This was filtered with a PTFE filter (manufactured by Toyo Filter Paper Co., Ltd., ADVANTEC DISMIC-25HP 25HP020AN, pore size 0.20 μm, diameter 25 mm) that had been washed with distilled water in advance, and used as an analysis sample.
(Quantitative analysis conditions)
Using the sum of the area values of multiple peaks detected between 5.4 and 6.6 minutes on an extracted ion chromatogram of 335.07556 to 335.0792 m / z, the analytical sample and the standard product were compared. Quantitative values were calculated. A chromatogram of an analytical sample prepared from a sample coffee beverage (Example 1) is shown in FIG. Multiple peaks of 5.4 to 6.6 minutes in the chromatogram of each sample coffee beverage are the chlorogenic acid lactones in the present invention, namely 5-cafe oil-1,3-quinolactone, 3-cafe oil-1. , 5-Kinolactone, 4-Café Oil-1,3-Kinolactone, 4-Café Oil-1,5-Kinolactone, and 5-Café Oil-1,4-Kinolactone. Is shown as the content of chlorogenic acid lactones in each sample coffee beverage.

The number of peaks and the peak height differ between the standard chlorogenic acid lactone chromatogram (Fig. 1) and the chlorogenic acid lactone chromatogram in the sample coffee beverage (Fig. 2). This is because the abundance ratios of the five types of components are different from those of coffee beverages. However, as described above, in the present invention, the total content of the five components in the beverage is the chlorogenic acid lactone content in the beverage, and the content of the chlorogenic acid lactones is calculated from the peak area. Therefore, the difference in the number of peaks and the peak height does not substantially affect the accuracy of the content measurement in this example.
<Analytical conditions for guaiacol, phenol, p-ethylphenol, p-cresol, and 2-acetylpyrrole (GC / MS)>
Put 5 ml of the sample solution in a 20 ml glass bottle with a screw (diameter 18 mm, manufactured by Gestel), seal it with a metal lid with a PTFE septum (manufactured by Gestel), and extract the aroma component by solid phase microextraction (SPME). Was done. The quantification was performed by the standard addition method using the peak area detected in the EIC mode of GC / MS. The equipment and conditions used are shown below.

SPME fiber: TableFlex / SS, 50/30 μm DVB / CAR / PDMS, (manufactured by Spellco)
Fully automatic volatile component extraction and introduction device: MultiPurposeSampler MPS2XL (manufactured by Gestel)
Preliminary heating: 40 ° C for 5 minutes Stirring: None Volatile component extraction: 40 ° C for 30 minutes Desorption time of volatile components: 3 minutes GC oven: GC7890A (manufactured by Agilent Technologies)
Column: VF-WAXms, 60 m × 0.25 mmi. d. df = 0.50 μm (manufactured by Agilent Technologies)
GC temperature condition: 40 ° C (5 minutes) → 5 ° C / min → 260 ° C (11 minutes)
Carrier gas: Helium, 1.2 ml / min, constant flow rate mode Injection: Splitless method Inlet temperature: 250 ° C
Mass spectrometer: GC / MS Triple Audio 7000 (manufactured by Agilent Technologies)
Ionization method: EI (70eV)
Measurement method: Scan measurement or simultaneous scan & SIM measurement Scan parameters: m / z 35-350
Quantitative ions can be selected from the ions shown below with good detection sensitivity, peak shape and peak separation: guaiacol m / z 109, 124 or 81 (81 in this example); p-ethylphenol m / z 107, 122 or 77 (107 in this example); p-cresol m / z 107, 108, 77 or 79 (107 in this example); phenol m / z 94, 66 or 65 (94 in this example); 2-Acetylpyrrole m / z 94, 109 or 66 (94 in this example).

If the peak shape or sensitivity is not good with any of the above ions, the sample solution can be diluted with distilled water to an appropriate ratio, or the SIM mode can be used.
3. 3. Sensory evaluation Among three trained professional panelists, use the sensory evaluation result (when the commercially available product 1 is opened at room temperature) to confirm the relationship with the corresponding score, and make the score as common as possible. After that, the sensory evaluation of the coffee beverage prepared in 1 above and the commercial products 1 to 3 was performed by three specialized panelists to evaluate the bad aftertaste of the coffee beverage. Specifically, each specialized panelist was scored in increments of 0.1 points based on the following criteria, and the average score is shown in Table 1. In the sensory evaluation, it is preferable that the average score exceeds 4.0 points based on the sensory evaluation result (sensory evaluation score: 4.0 points) of the commercially available product 1 having a somewhat low guaicol content at room temperature opening. It was determined to be a coffee drink.

<Criteria for evaluation points>
5.0 points: No bad aftertaste.
4.0 points: There is almost no bad aftertaste.

3.0 points: There is a little bad aftertaste.
2.0 points: There is a bad aftertaste.
1.0 point: The aftertaste is too strong and it is not suitable as a beverage.

The results are shown in Table 1.

As shown in Table 1, coffee in which the content ratio ((b) / (a)) of the content of chlorogenic acid lactones (b) to the content of guaiacol (a) is within the predetermined range of the present invention. In the beverages (Examples 1 to 7), the sensory evaluation points after 2 hours at room temperature all exceeded 4.0 points, indicating that the backing bitterness was suppressed and the bad aftertaste was also improved. rice field. Therefore, according to the present invention, the content ratio ((b) / () of the content (mg / L) of chlorogenic acid lactones (b) and the content (μg / L) of guaiacol (a) in the coffee beverage. By adjusting the contents of chlorogenic acid lactones and guaiacol so that a)) is within a specific range, the backing bitterness peculiar to coffee is suppressed regardless of the liquid temperature, and the container is packed with a good aftertaste. It became clear that coffee drinks could be realized.

Since the present invention provides a packaged coffee beverage in which the bad aftertaste generated after opening is improved, it has high industrial applicability.

Claims (9)

It contains chlorogenic acid lactones (b) and guaiacol (a), meets the content (μg / L) of the content of (b) (mg / L) / (a)]> 0.020, guaiacol A packaged coffee beverage having a content of (a) of 500 μg / L or less. Further, claim that it contains phenol (c) and satisfies [(b) content (mg / L) / {(a) + (c)} content (μg / L)]> 0.0080. The packaged coffee beverage according to 1. Further, it contains p-ethylphenol (d), p-cresol (e) and 2-acetylpyrrole (f), and the content of [(b) (mg / L) / {(a) + (c) + The packaged coffee beverage according to claim 2, wherein the content (μg / L) of (d) + (e) + (f)}] ≥ 0.0050 is satisfied. The packaged coffee beverage according to any one of claims 1 to 3, wherein the content of guaiacol (a) is 100 μg / L to 500 μg / L. The packaged coffee beverage according to any one of claims 1 to 4, wherein the content of the chlorogenic acid lactones (b) is 3.0 mg / L to 15.0 mg / L. The packaged coffee beverage according to any one of claims 1 to 5 , which is black coffee. The packaged coffee beverage according to any one of claims 1 to 6 , wherein the beverage has a Brix value of 0.4 or more. The packaged coffee beverage according to any one of claims 1 to 7 , which is filled in a container with a recapable lid. A method for manufacturing packaged coffee beverages
(I) [Content of chlorogenic acid lactones (b) (mg / L) / Content of guaiacol (a) (μg / L)]> 0.020 , and content of guaiacol (a) is 500 μg / L. The steps of adjusting the contents of (a) and (b) so as to satisfy the following requirements, and
(Ii) Container filling process,
The production method.

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