Flavor deterioration suppressant

Abstract

The present invention relates to a flavor deterioration suppressant that contains a coffee silverskin extract. The present invention also relates to: a perfume composition (flavor / fragrance composition) or a food or beverage product that contains citral and the flavor deterioration suppressant; and a method for suppressing flavor deterioration in a citral-containing composition, said method comprising adding or blending a flavor deterioration suppressant. According to a preferable aspect of the present invention, it is possible to suppress the generation of a flavor deterioration component contained in a fragrance composition or a food or beverage product, in particular, a flavor deterioration component derived from citral, and to reduce discomfort due to off-taste and off-flavor.

Description

Flavor deterioration inhibitor

[0001] The present invention relates to a flavor deterioration inhibitor, a flavor composition and food and beverage containing the same, and a method for inhibiting flavor deterioration.

[0002] Citral has a fresh, citrusy aroma and is a major flavor component of lemon. Due to its properties, it is often used in acidic beverages and foods, but it is known that under acidic conditions, it easily degrades due to light and heat, producing unpleasant off-flavors and odors (also called "off-flavors") (Non-Patent Documents 1 and 2). Among these, p-cresol, which has a medicinal flavor, and p-methylacetophenone, which has an apricot kernel-like flavor, have low thresholds and are considered to be the main causes of off-flavors and odors. In particular, p-cresol is easily recognized as an off-flavor or odor because its properties differ significantly from citrus flavors. Various technologies have been proposed to counteract the off-flavors and odors caused by citral degradation. For example, Patent Document 1 proposes a degradation odor inhibitor which is a mixture of lemon myrtle extract and a plant extract of the Myricaceae family Myrica genus in a certain proportion. Patent Document 2 also proposes a flavor composition which suppresses the production of p-methylacetophenone by containing tea polyphenols. Furthermore, Patent Document 3 proposes a technique for suppressing the production of p-cymene or p-methylacetophenone by including an extract from rubus or olive fruit. However, these have not shown any inhibitory effect on p-cresol. On the other hand, Patent Document 4 proposes a method for suppressing the production of degradation odor in p-cresol by utilizing the interaction between antioxidant components and transition metal ions. Furthermore, Patent Document 5 proposes a degradation inhibitor for p-cresol or p-methylacetophenone containing theanaphthoquinones as an active ingredient.

[0003] Japanese Patent Publication No. 2017-55760, Japanese Patent Publication No. 2003-096486, Japanese Patent Publication No. 2016-189768, Japanese Patent Publication No. 2004-123788, International Publication No. 2021 / 019763

[0004] Monthana Weerawatanakorn, et al., Journal of Food and Drug Analysis, 2015, 23, 176-190; Masanori Sawada, et al., Nippon Shokuhin Kagaku Kaishi, 1999, vol.46, No. 3, 181-186; E. O. Owe, et al., Biocatalysis and Agricultural Biotechnology, 2021, March, 32, 101949

[0005] Technologies for suppressing off-flavors and off-odors generated by flavor deterioration are still desired. For example, among the off-flavors and off-odors generated from citral, p-cresol and p-methylacetophenone have particularly strong unpleasant odors, and thus the development of technologies showing a production suppressing effect is eagerly desired. Although technologies for suppressing off-flavors and off-odors have been developed so far, in terms of free product design, there is a strong demand for more effective technologies and, further, for the search for substances that suppress the generation of off-flavors derived from raw materials and have a weak aroma. In this specification, "flavor" means aroma, taste or both. Also, "off-flavors and off-odors" means off-flavors, off-odors or both.

[0006] Under such circumstances, the present inventors have conducted intensive studies and found that an extract obtained from a by-product separated during the roasting of coffee beans has a high off-flavor suppressing effect. This by-product is called "chaff" and is known to mainly contain the silver skin, which is the thin skin of coffee beans (Non-Patent Document 3). In this specification, coffee silver skin and chaff are treated as the same thing. The present inventors have found that by adding this coffee silver skin extract to the target food, beverage or fragrance composition, the generation of flavor deterioration components can be suppressed and the discomfort caused by off-flavors and off-odors can be reduced, thus completing the present invention.

[0007] The present invention includes the following embodiments: [1] A flavor deterioration inhibitor containing coffee silverskin extract. [2] The flavor deterioration inhibitor according to [1], which suppresses the generation of flavor deterioration components derived from citral. [3] The flavor deterioration inhibitor according to [2], wherein the flavor deterioration components derived from citral are one or more selected from p-cresol and p-methylacetophenone. [4] The flavor deterioration inhibitor according to [3], wherein the flavor deterioration components derived from citral are p-cresol and p-methylacetophenone. [5] The flavor deterioration inhibitor according to [2], wherein the flavor deterioration components derived from citral are one or more selected from photocitral A, photocitral B, epiphotocitral A, and 2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropanal. [6] A fragrance composition containing citral and the flavor deterioration inhibitor according to any one of [1] to [5]. [7] A food or beverage containing citral and a flavor deterioration inhibitor according to any one of [1] to [5] above. [8] A method for inhibiting flavor deterioration, comprising adding or blending a flavor deterioration inhibitor according to any one of [1] to [5] above into a flavor composition or food or beverage.

[0008] By adding or incorporating the flavor degradation inhibitor of the present invention into food and beverages or flavor compositions, off-flavors and off-odors generated due to flavor degradation can be suppressed. The flavor degradation inhibitor of the present invention can be particularly suitably used in food and beverages or flavor compositions containing citral, suppressing the generation of flavor degradation components derived from citral and reducing unpleasantness caused by off-flavors and off-odors.

[0009] The following describes in detail each aspect of the present invention.

[0010] 1. Flavor deterioration inhibitor A flavor deterioration inhibitor according to one aspect of the present invention is characterized by containing coffee silverskin extract. Coffee cherries, which are coffee fruits, consist from the outside in: the outer skin, the flesh, the mucilage, the parchment, the silverskin, and the seed (coffee bean or green bean). Coffee silverskin (also simply called "silverskin") is the thin seed coat that surrounds the coffee bean inside the coffee fruit, and is also called "chaff."

[0011] Coffee silverskin originates from coffee beans and therefore comes in various varieties. In this embodiment, any variety of coffee silverskin can be used. Arabica and Canephora are the most commonly consumed varieties of coffee beans, but it is preferable to use Canephora coffee silverskin because it has a better effect in suppressing flavor deterioration. Coffee silverskin is obtained during the refining and roasting processes of coffee beans. Some of the coffee silverskin is removed during the refining process when green beans are extracted from the coffee fruit. On the other hand, most of the silverskin that remains attached peels off during roasting, but some may remain in the center cut of the coffee bean. This silverskin can be separated and recovered when the roasted beans are ground. The coffee silverskin that can be used in this embodiment is not particularly limited; it may be that which has been removed during the refining process, that which has peeled off during roasting, or that which has been extracted from the center cut.

[0012] In one embodiment of this invention, coffee silver skin sterilized and ground by known means may be used. Furthermore, when coffee silver skin is collected during coffee bean roasting or grinding, bean fragments and other particles may be mixed into the coffee silver skin. If there are many bean fragments, not only will the color of the silver skin extract become darker, but the coffee-like aroma will also become more prominent. Therefore, since this may affect the appearance and flavor of food and beverages or flavor compositions to which the flavor deterioration inhibitor according to this embodiment is added or blended, it is preferable that the amount of bean fragments mixed in be below a certain amount. Specifically, it is preferable that it be 20% by mass or less, and more preferably 10% by mass or less, relative to the total amount of coffee silver skin collected during coffee bean roasting and the mixed bean fragments.

[0013] In this embodiment, "coffee silver skin extract" refers to solvent-soluble components in coffee silver skin extracted using a solvent. There are no particular restrictions on the method for obtaining the coffee silver skin extract; for example, it may be extracted by stirring in a solvent, or by immersion in a solvent.

[0014] As the extraction solvent, it is preferable to use water or an aqueous organic solvent. The water content of the aqueous organic solvent is usually preferably 20% by mass or more, and more preferably 30% by mass or more. Examples of organic solvents include ethanol, propylene glycol, glycerin, and isopropyl alcohol. The water content of the aqueous organic solvent also varies depending on the type of organic solvent used. For example, when the organic solvent used is ethanol, the water content of the aqueous organic solvent is preferably 70% by mass or more; for propylene glycol, 50% by mass or more; for glycerin, 30% by mass or more; and for isopropyl alcohol, 50% by mass or more.

[0015] The mixing ratio of coffee silverskin to water or aqueous organic solvent is preferably 100 to 5000 parts by mass of water or aqueous organic solvent per 100 parts by mass of coffee silverskin, more preferably 300 to 3000 parts by mass, and even more preferably 700 to 1500 parts by mass.

[0016] The extraction temperature is not particularly limited, but is preferably 0°C or higher, more preferably 50°C or higher, and even more preferably 75°C or higher. The extraction time is not particularly limited, but is preferably 1 to 600 minutes, more preferably 10 to 180 minutes, and even more preferably 30 to 120 minutes.

[0017] The method of solid-liquid separation after extraction is not particularly limited, and known separation methods such as decantation, centrifugation, natural filtration using filter paper or filter cloth, filter press, screw press, centrifugal filtration, closed-type pressure filtration, vacuum filtration, and press can be used. These separation methods may be combined as needed, and filter aids may also be used. Furthermore, filtration may be made more efficient by filtration under pressure.

[0018] In the extraction process of the present invention, the pH of the extract and the extraction solvent may be adjusted as appropriate. pH adjustment can be performed by adding an acid or base, and the type and concentration are not particularly limited. This adjustment may be performed before, during, or after the extraction operation.

[0019] The pH of the extract is not particularly limited, but is preferably 4 or higher, more preferably 5 or higher, and even more preferably 5.5 or higher. The pH of the extract is preferably in the acidic or neutral range, and is usually preferably 4 to 7, more preferably 5 to 7, and even more preferably 5.5 to 7.

[0020] The liquid phase obtained by solid-liquid separation may be concentrated as needed. The concentration method is not particularly limited, and known concentration methods such as evaporation concentration, membrane concentration, and freeze concentration can be used. These concentration methods may be combined as appropriate as needed. In addition, a solvent may be added and diluted as needed. Fractionation may be performed depending on the purpose, specifically, a fraction with a high molecular weight of 10 kDa or more is preferred, a fraction with a high molecular weight of 30 kDa or more is more preferred, and a fraction with a high molecular weight of 50 kDa or more is even more preferred to be fractionated and recovered.

[0021] The content (by mass) of coffee silver skin extract in the aforementioned flavor deterioration inhibitor is preferably 0.1 to 400 ppm as solid content, more preferably 1 to 100 ppm, and even more preferably 10 to 30 ppm.

[0022] The flavor degradation inhibitor according to this embodiment is particularly effective in suppressing the generation of flavor degradation components derived from citral, and can be suitably used in food and beverages or flavor compositions containing citral, especially in acidic beverages and acidic foods. According to the preferred embodiment of this feature, it is possible to suppress the degradation of citral, particularly due to light and heat, which generates unpleasant off-flavors, and to prolong the fresh, citrusy flavor of citral.

[0023] Flavor degradation components derived from citral include one or more selected from p-cresol and p-methylacetophenone, which may be either p-cresol or p-methylacetophenone, or a combination of p-cresol and p-methylacetophenone. These compounds are known to be produced by an acid-catalyzed cyclization reaction of citral, followed by an oxidation reaction. Furthermore, it is known that this reaction is accelerated under heating conditions. In a preferred embodiment, the flavor degradation inhibitor according to this embodiment can suppress the production of both p-cresol and p-methylacetophenone, which have particularly strong unpleasant odors, and is therefore useful for freely designing products in food and beverages or flavor compositions. In addition, one or more flavor degradation components derived from citral include one or more selected from photocitral A, photocitral B, epiphotocitral A, and 2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropanal. These compounds are known to be produced by an acid-catalyzed photocyclization reaction of citral and the subsequent photooxidation reaction.

[0024] 2. Flavor Composition The flavor composition according to this embodiment contains citral and the above-mentioned flavor deterioration inhibitor. According to this embodiment, by including citral and the flavor deterioration inhibitor, the generation of flavor deterioration components derived from citral can be suppressed, and the fresh citrus flavor of citral can be preserved for a longer period of time. The amount of flavor deterioration inhibitor varies depending on, for example, the amount of citral in the flavor composition, and is not particularly limited, but it is preferable that the solid content of the coffee silverskin extract contained in the flavor deterioration inhibitor is in the range of 5 to 300% by mass relative to the citral content, more preferably 10 to 200% by mass, and even more preferably 50 to 200% by mass. Furthermore, the amount of solid added coffee silverskin extract (by mass) in food and beverages containing citral is preferably in the range of 0.1 to 100 ppm, more preferably 1 to 50 ppm, and even more preferably 5 to 30 ppm. The citral content can be appropriately selected depending on the type or purpose of the food or beverage to which the flavor composition according to this embodiment is added or blended, and is not particularly limited, but is generally preferred to be 0.01 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the mass of the flavor composition.

[0025] The fragrance composition of the present invention may optionally contain known fragrances and / or conventional additives, within a quantitative or qualitative range that does not impair the effects of the present invention.

[0026] Examples of fragrances include various synthetic fragrances, natural fragrances, natural essential oils, and plant extracts. For example, natural essential oils, natural fragrances, and synthetic fragrances are listed in "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Technologies (Fragrances), Part II: Food Fragrances, P88-131, published January 14, 2000."

[0027] The additives may include conventional additives used in fragrance compositions, such as water and solvents like ethanol; and fixatives such as ethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium-chain triglyceride, medium-chain diglyceride, and animal and vegetable oils and fats.

[0028] The fragrance composition according to this embodiment may be a flavor composition for food and beverages, or a fragrance composition for adding scent to cosmetics, hygiene products, etc. Of these fragrance compositions, a flavor / fragrance composition having a citrus flavor is particularly preferred. The fragrance composition according to this embodiment can be manufactured by mixing citral, a flavor deterioration inhibitor, a fragrance, and one or more conventional additives.

[0029] 3. Food and beverages The food and beverages according to this embodiment contain citral and the flavor deterioration inhibitor described above. According to this embodiment, by including citral and a flavor deterioration inhibitor, the generation of flavor deterioration components derived from citral can be suppressed, and the fresh citrus-like flavor of citral can be preserved for a longer period of time.

[0030] The amount of flavor deterioration inhibitor is not particularly limited and varies depending on, for example, the citral content in the food and beverage. However, it is preferable that the solid content of the coffee silverskin extract contained in the flavor deterioration inhibitor is in the range of 0.5 to 300% by mass relative to the citral content, more preferably 10 to 200% by mass, and even more preferably 50 to 200% by mass. Furthermore, the amount of solid coffee silverskin extract added (by mass) in the food and beverage containing citral is preferably in the range of 0.1 to 100 ppm, more preferably 1 to 50 ppm, and even more preferably 5 to 30 ppm. The citral content is not particularly limited and can be appropriately selected depending on the type or purpose of the food and beverage to which the flavor deterioration inhibitor according to this embodiment is added or blended. However, the amount added (by mass) in the food and beverage is usually preferably 0.01 to 300 ppm, more preferably 0.01 to 100 ppm, and even more preferably 0.01 to 15 ppm. Food and beverages according to this embodiment can be manufactured by adding citral and a flavor degradation inhibitor, or by blending citral and a flavor degradation inhibitor together with other raw materials during the manufacturing process of the food and beverage. If citral is included as an ingredient in the food and beverage, the amount of citral added or blended should be adjusted so that the citral content falls within a predetermined range. Alternatively, citral and a flavor degradation inhibitor may be included in the food and beverage by adding or blending the aforementioned flavor composition.

[0031] The foods and beverages described in this embodiment are not particularly limited and include beverages such as alcoholic beverages, non-alcoholic beverages, carbonated beverages, fruit juices, dairy beverages, sports drinks, and tea beverages; frozen desserts such as yogurt, jelly, and ice cream; confectionery such as candy, corn syrup, and gum; processed fruit and vegetable foods such as jam and marmalade; and seasoning liquids such as dressings. Among these, liquid foods such as beverages are particularly preferred.

[0032] 4. Method for Suppressing Flavor Degradation The method for suppressing flavor degradation according to this embodiment includes adding or blending the above-described flavor degradation inhibitor into a flavor composition or food or beverage. By adding or blending the flavor degradation inhibitor into a flavor composition or food or beverage, the degradation of flavor components due to light and heat can be suppressed, and the generation of unpleasant off-flavors and off-odors can be suppressed. In particular, since the flavor degradation inhibitor is excellent in suppressing the generation of flavor degradation components derived from citral, the method for suppressing flavor degradation according to this embodiment can be suitably used in food or beverage or flavor compositions containing citral.

[0033] The flavor compositions or food and beverages for which flavor deterioration is suppressed by this embodiment are as described above. The amount of flavor deterioration inhibitor added or blended can be appropriately selected according to the type and purpose of the flavor composition or food and beverage, and is not particularly limited.

[0034] The method of adding or incorporating the flavor deterioration inhibitor into a flavor composition or food or beverage is not particularly limited. The flavor deterioration inhibitor may be added to the finished product of the flavor composition or food or beverage, or it may be included in the flavor composition or food or beverage by adding or incorporating it during the manufacturing process of the flavor composition or food or beverage.

[0035] The present invention will be described in more detail below with reference to examples, but the present invention is not limited in any way to these examples. In this application, the quantitative determination of p-cresol, p-methylacetophenone, and citral was performed using a high-performance liquid chromatography system (Agilent Technologies, Agilent 1260 Infinity II LC). The analytical conditions were as follows. Column: inertsil ODS-3, particle size 3 μm, inner diameter 2.1 x length 150 mm (GL Sciences Co., Ltd.) Column temperature: 35°C Mobile phase: (water (containing 0.1 vol% formic acid): acetonitrile) = 60:40 (0-15 min), 10:90 (15-30 min), 60:40 (30-40 min) Flow rate: 0.17 ml / min Detection: <p-cresol> fluorescence detector: excitation wavelength 284 nm, fluorescence wavelength 310 nm <p-methylacetophenone> UV spectrophotometer: 254 nm <Citral> UV spectrophotometer: 254 nm

[0036] [Example 1] Using a 300 mL four-necked flask, 20 g of 14% by mass ethanol aqueous solution was added to 20 g of coffee silver skin (derived from Canephora species, with a content of bean fragments of 7-8% by mass). The mixture was stirred using a stirring blade, and extraction was carried out for 1 hour after reaching 88°C. Subsequently, coarse filtration was performed using a 48 mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 2.1% by mass, pH 5.7).

[0037] [Comparative Example 1] 5 g of lemon myrtle was mixed with 50 g of 18.5% by mass ethanol aqueous solution, stirred with a magnetic stirrer, and heated to 40°C for 30 minutes to extract. Then, coarse filtration was performed using a 48-mesh stainless steel mesh, followed by filtration using filter paper (ADVANTEC, No. 2) to obtain an extract (solid concentration 2.1% by mass, pH 5.2).

[0038] [Test Example 1] HPLC Measurement 80 g of fructose-glucose liquid sugar (Nippon Shokuhin Kako Co., Ltd.), 2.5 g of anhydrous citric acid (Junsei Kagaku Co., Ltd.), and 0.6 g of trisodium citrate (Junsei Kagaku Co., Ltd.) were dissolved per 1 kg to prepare a pH 3.0 sugar-acid solution. 7.5 ppm of citral (Tokyo Chemical Industry Co., Ltd.) was added to this solution, and 100 g portions were dispensed into retort pouches. To the dispensed solutions, 0.06% by mass (Example 1-1), 0.10% by mass (Example 1-2), and 0.06% by mass (Comparative Example 1-1), or 0.10% by mass (Comparative Example 1-2) of the extract from Comparative Example 1 were added. The pouches were sealed with a heat sealer while removing air, and sterilized by immersion at 80°C for 10 minutes. After sterilization, each sample was subjected to heat torture at 60°C for 3 days under light shielding. As controls, samples were prepared by dispensing the substance into retort pouches and storing them refrigerated at 4°C or below without any additives (No Additive 1), and by storing the substance at 60°C for 3 days without any additives (No Additive 2). Each sample after abuse was used directly for HPLC measurement. The measurement results are shown as relative values ​​with the measurement value of No Additive 2 set to 100 (Table 1).

[0039]

[0040] [Example 2] 200 g of coffee silver skin (derived from Canephora species, with a content of bean fragments of 7-8% by mass) was placed in a glass column with an inner diameter of 7.5 cm and a height of 20 cm, and a 14% by mass ethanol aqueous solution at approximately 70°C was pumped from below at a rate of 9 ml / min. The glass column was heated by circulating 80°C antifreeze through the jacket. The effluent was collected and mixed up to 800 ml, and then filtered using a filter aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 3.8% by mass, pH 5.8).

[0041] [Example 3] 150 g of coffee silver skin (derived from Arabica beans, with a content of 7-8% by mass of bean fragments) was placed in a glass column with an inner diameter of 7.5 cm and a height of 20 cm, and a 14% by mass ethanol aqueous solution at approximately 70°C was pumped from below at a rate of 9 ml / min. The glass column was heated by circulating 80°C antifreeze through the jacket. The effluent was collected and mixed up to 600 ml, and then filtered using a filter aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 2.5% by mass, pH 5.1).

[0042] [Test Example 2] HPLC Measurement 80 g of fructose glucose liquid sugar, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate were dissolved per 1 kg to prepare a sugar acid solution with a pH of 3.0. 7.5 ppm of citral was added thereto, and 100 g portions were dispensed into retort pouches. To the dispensed liquid, 0.034% by mass of the extract of Example 2 (Example 2-1) or 0.053% by mass of the extract of Example 3 (Example 3-1) was added, and while removing air, it was sealed with a heat sealer and subjected to immersion sterilization at 80°C for 10 minutes. Each sample was subjected to heat treatment at 60°C for 3 days under light shielding after sterilization. As in Test Example 1, No addition 1 and No addition 2 were prepared as controls. Each sample after the abuse was used as it was for HPLC measurement. The measurement results showed relative values with the measured value of No addition 2 set to 100 (Table 2).

[0043] As shown in Table 2, by adding the coffee silver skin extract, the generation of p-cresol and p-methylacetophenone could be suppressed. Also, Example 2-1 using the coffee silver skin extract of the Canephora species had a higher inhibitory effect on the generation of p-cresol and p-methylacetophenone than Example 3-1 using the coffee silver skin extract of the Arabica species.

[0044] [Comparative Example 2] L-ascorbic acid (Junsei Chemical Co., Ltd.) was dissolved in pure water to a concentration of 20 mg / ml.

[0045] 〔Test Example 3〕 HPLC Measurement 80 g of fructose glucose liquid sugar, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate were dissolved per 1 kg to prepare a sugar acid solution with a pH of 3.0. Citral was added thereto (7.5 ppm), and 100 g portions were dispensed into retort pouches. The dispensed solutions were added with the extract of Example 2 at 0.0026% by mass (Example 2-2), 0.026% by mass (Example 2-3), 0.26% by mass (Example 2-4), the solution of Comparative Example 2 at 0.005% by mass (Comparative Example 2-1), 0.05% by mass (Comparative Example 2-2), or 0.5% by mass (Comparative Example 2-3), sealed with a heat sealer while removing air, and subjected to immersion sterilization at 80°C for 10 minutes. Each sample was subjected to heat abuse at 60°C for 3 days under light shielding after sterilization. As in Test Example 1, Additive-free 1 and Additive-free 2 were prepared as controls. Each sample after abuse was used as it was for HPLC measurement. The measurement results showed relative values with the measured value of Additive-free 2 taken as 100 (Table 3).

[0046]

[0047] 〔Comparative Example 3〕 Chlorogenic acid hemihydrate (Nacalai Tesque, Inc.) was dissolved in 95 vol% ethanol to a concentration of 20 mg / ml.

[0048] [Test Example 4] Sensory Evaluation A pH 3.0 sugar-acid solution was prepared by dissolving 80 g of fructose-glucose syrup, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate per 1 kg. 7.5 ppm of citral was added to this solution, and 100 g portions were dispensed into retort pouches. To the dispensed solutions, 0.04% by mass of the extract from Example 2 (Example 2-5) or 0.075% by mass of the solution from Comparative Example 3 (Comparative Example 3-1) was added, and the pouches were sealed with a heat sealer while removing air, and sterilized by immersion at 80°C for 10 minutes. After sterilization, each sample was subjected to heat abuse at 60°C for 3 days under light shielding. As in Test Example 1, two control samples, no additives 1 and no additives 2, were prepared. For each sample after abuse, an orthonasal aroma (scent at the tip of the nose) was evaluated before drinking, followed by a retronasal aroma (scent in the mouth) after swallowing, by a panel of 10 experienced individuals. The evaluation criteria were as follows, with "no additives 1" (score: 1 point) and "no additives 2" (score: 5 points) as the baseline, and the deterioration odor of the flavor of each sample was evaluated (Table 4). 1 point - No deterioration odor detected 2 points - Slight deterioration odor detected 3 points - Deterioration odor detected 4 points - Strong deterioration odor detected 5 points - Very strong deterioration odor detected

[0049]

[0050] [Example 4] Using a 300 mL four-necked flask, 20 g of 15% by mass propylene glycol solution was added to 20 g of coffee silver skin (derived from Canephora species, with a content of bean fragments of 7-8% by mass). The mixture was stirred using a stirring blade, and extraction was carried out for 1 hour after reaching 95°C. Subsequently, coarse filtration was performed using a 48-mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Super Light No. 1) to obtain the extract. Furthermore, the extract was concentrated using an evaporator until its mass was halved.

[0051] [Test Example 5] GC-MS Measurement 80 g of fructose-glucose syrup, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate were dissolved per 1 kg to prepare a pH 3.0 sugar-acid solution. 7.5 ppm of citral was added to this solution, and 200 g was dispensed into heat-resistant transparent PET bottles. 0.1% by mass of the extract from Example 2 (Example 2-6) and 0.1% by mass of the extract from Example 4 (Example 4-1) were added to the dispensed solution, and the bottles were sealed and sterilized by immersion at 80°C for 10 minutes. After sterilization, the bottles were subjected to a 2-week photoabuse test under conditions of 8,000-10,000 lux and 10°C. As controls, samples were prepared by dispensing into PET bottles, wrapping them twice with aluminum foil, completely covering the caps to ensure no gaps were left, and storing them at 10°C for two weeks under light-shielding conditions (no additives 3), and by storing them at 8,000-10,000 lux and 10°C for two weeks (no additives 4). After two weeks of storage or after abuse, 5 g of each sample was taken, and 5-nonanone was added as an internal standard at a final concentration of 0.1 ppm. The aroma in the equilibrated headspace was adsorbed onto solid-phase microextraction (SPME) fibers, and GC / MS measurements were performed. The measurement results were compared using relative intensity relative to the internal standard, with the measured value of no additive 4 set to 100 (Table 5). The analytical conditions were as follows.

[0052] Headspace SPME-GC / MS Instrument: MPS (GERSTEL K.K.) + 8890GC / 5977BMSD (Agilent Technologies, Inc.) Fiber: PDMS / DVB Equilibrium temperature: 60°C Equilibrium time: 10 min Adsorption time: 20 min Column: BC-WAX, inner diameter 0.18 mm x length 20 m, film thickness 0.18 μm (GL Sciences Co., Ltd.) Injection mode: Splitless injection Temperature: 250°C Oven temperature: 45°C (1 min) → 230°C, 20°C / min Carrier gas, flow rate: Helium, 1 mL / min

[0053]

[0054] [Example 5] 775 g (solid concentration 3.8% by mass) of the extract obtained in Example 2 was placed in an evaporator, the bath temperature was set to 50°C, and the concentrate was concentrated under reduced pressure of 130 mmHg or less. 103 g of the resulting concentrate was pre-frozen with dry ice / acetone at approximately -78°C, and freeze-dried overnight in a freeze-dryer (Tokyo Rikakikai Co., Ltd.) under vacuum conditions of 60 Pa or less to obtain 29.3 g of dried solids.

[0055] [Test Example 6] Per 100g, 95.4g of sorbitol (Merck KGaA), 2.0g of sugar ester (Mitsubishi Chemical Corporation), 0.5g of aspartame (Ajinomoto Co., Inc.), 0.5g of fine silicon dioxide (Fuji Silysia Chemical Co., Ltd.), 1.2g of anhydrous citric acid (Iwata Chemical Industry Co., Ltd.), and 0.4g of 10% by mass citral solution (diluted with propylene glycol) were mixed, and tablets with a diameter of 13mm, an average hardness of 190N, and weighing approximately 1g per tablet were produced using a manual hydraulic tablet press (Fuji Pharmaceutical Machinery Co., Ltd.) (Additive-free 5, Additive-free 6). Furthermore, per 100g, 95.1g of sorbitol, 2.0g of sugar ester, 0.5g of aspartame, 0.5g of fine silicon dioxide, 1.2g of anhydrous citric acid, 0.4g of 10% by mass citral solution (diluted with propylene glycol), and 0.3g of the dried solids from Example 5 were mixed, and tablets with a diameter of 13mm, an average hardness of 190N, and a weight of approximately 1g per tablet were prepared using a manual hydraulic tablet press (Example 5-1). Each tablet was placed in a resealable polyethylene bag and then placed in an aluminum pouch. The additive-free tablet 5 was stored in the dark at 4°C or below for 7 days, while the additive-free tablet 6 and the tablets from Example 5-1 were subjected to heat torture at 60°C for 7 days in the dark. 19g of pure water was added to each tablet, stirred and dissolved, and then filtered through a filter (GVS Japan Co., Ltd., PVDF, 0.45μm) for HPLC measurement. The measurement results are shown as relative values, with the measurement value for sample 6 (no additive) set to 100 (Table 6).

[0056] As shown in Table 6, the amount of citral remaining was improved by adding coffee silverskin extract.

[0057] [Example 6] Using a 300 mL four-necked flask, 20 g of coffee silver skin (derived from Canephora species, with a content of 7-8% by mass of bean fragments) was mixed with 200 g of 14% by mass ethanol aqueous solution. The mixture was stirred using a stirring blade and extracted for 1 hour after reaching 85°C. After that, coarse filtration was performed using a 48 mesh stainless steel mesh to obtain the extract. To the obtained extract, 10% by mass of the above coffee silver skin was added again, and extraction was performed again for 1 hour, followed by coarse filtration. Finally, auxiliary filtration was performed using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain the extract (solid concentration 3.8% by mass, pH 5.5).

[0058] [Test Example 7] 80 g of fructose-glucose syrup, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate were dissolved per 1 kg to prepare a pH 3.0 sugar-acid solution. Citral was added to this solution (7.5 ppm), and 100 g portions were dispensed into retort pouches. 0.03% by mass of the extract from Example 6 (Example 6-1) was added to the dispensed solution, and the pouches were sealed with a heat sealer while removing air. Sterilization was performed by immersion at 80°C for 10 minutes. After sterilization, each sample was subjected to heat torture at 60°C for 16 hours under light protection. As controls, samples were prepared that were stored refrigerated at 4°C or below without any additives after dispensing into retort pouches (No Additive 7), and samples that were stored at 60°C for 16 hours without any additives (No Additive 8). Each sample after torture was used directly for HPLC measurement. The measurement results are shown as relative values ​​with the measurement value of No Additive 8 set to 100 (Table 7).

[0059]

[0060] [Example 7] A portion of the extract obtained in Example 2 (solid concentration 3.8% by mass) was diluted with water to make 1000 g of an aqueous solution with a solid concentration of 0.1% by mass, and this was placed in an ultrafilter (ADVANTEC) equipped with an ultrafilter (ADVANTEC) with a fractional molecular weight cutoff of 50 kDa. The mixture was pressurized to approximately 0.2 MPa using nitrogen, and filtration was performed while stirring with a magnetic stirrer to obtain membrane residue and membrane-passed fraction. The membrane residue was diluted with deionized water to a total of 50 g and collected as the membrane residue fraction. The membrane-passed fraction was concentrated to about 100 g using an evaporator, and then liquid-liquid extraction was performed twice using 100 ml of ethyl acetate (Nacalai Tesque Co., Ltd.), and the aqueous layer and ethyl acetate layer were collected separately. After concentration with the evaporator, deionized water was added to the aqueous layer to a total of 50 g and collected as the aqueous layer fraction. The ethyl acetate layer was collected by adding a 20% by mass aqueous ethanol solution until the total amount reached 50 g, and this was designated as the ethyl acetate fraction.

[0061] [Test Example 8] HPLC Measurement A pH 3.0 sugar-acid solution was prepared by dissolving 80 g of fructose-glucose syrup, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate per 1 kg. 7.5 ppm of citral was added to this solution, and 100 g portions were dispensed into retort pouches. To the dispensed solution, 0.06% by mass of the membrane residue fraction from Example 7 (Example 7-1), 0.06% by mass of the aqueous layer fraction from Example 7 (Example 7-2), or 0.06% by mass of the ethyl acetate fraction from Example 7 (Example 7-3) was added. The pouches were sealed with a heat sealer while removing air, and sterilized by immersion at 80°C for 10 minutes. After sterilization, each sample was subjected to heat torture at 60°C for 3 days under light protection. As in Test Example 1, control samples 1 (no additives) and 2 (no additives) were prepared. Each sample after torture was used directly for HPLC measurement. The measurement results are shown as relative values, with the measurement value for sample 2 (no additive) set to 100 (Table 8).

[0062] As shown in Table 8, a high level of odor suppression was observed in the film residue fraction of the coffee silver skin extract, where high molecular weight components migrate.

[0063] [Example 8] Using a 300 mL four-necked flask, 20 g of 14% by mass ethanol aqueous solution was added to 20 g of coffee silver skin (derived from Canephora species, with a content of bean fragments of 7-8% by mass). The mixture was stirred using a stirring blade, and extraction was carried out for 1 hour after reaching 85°C. Subsequently, coarse filtration was performed using a 48 mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 1.9% by mass, pH 5.9).

[0064] [Example 9] Using a 300 mL four-necked flask, 20 g of coffee silver skin (derived from Canephora species, with a content of bean fragments of 7-8% by mass) was mixed with 200 g of 14% by mass ethanol aqueous solution and 0.20 g of sodium bicarbonate (Junsei Chemical Co., Ltd.). The mixture was stirred using a stirring blade and extracted for 1 hour after reaching 85°C. Subsequently, coarse filtration was performed using a 48 mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 2.2% by mass, pH 6.6).

[0065] [Example 10] Using a 300 mL four-necked flask, 20 g of 14% by mass ethanol aqueous solution was added to 20 g of coffee silver skin (derived from Arabica variety, with a content of bean fragments of 7-8% by mass). The mixture was stirred using a stirring blade, and extraction was carried out for 1 hour after reaching 85°C. Subsequently, coarse filtration was performed using a 48 mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 1.5% by mass, pH 5.2).

[0066] [Example 11] Using a 300 mL four-necked flask, 20 g of coffee silver skin (derived from Arabica beans, with a content of 7-8% by mass of bean fragments) was mixed with 200 g of 14% by mass ethanol aqueous solution and 0.20 g of sodium bicarbonate (Junsei Chemical Co., Ltd.). The mixture was stirred using a stirring blade, and extraction was carried out for 1 hour after reaching 85°C. Subsequently, coarse filtration was performed using a 48 mesh stainless steel mesh, followed by auxiliary filtration using filter paper (ADVANTEC, No. 2) and a filtration aid (Tokyo Konno Co., Ltd., Super Light No. 1) to obtain an extract (solid concentration 1.7% by mass, pH 5.9).

[0067] [Test Example 9] HPLC Measurement A pH 3.0 sugar-acid solution was prepared by dissolving 80 g of fructose-glucose syrup, 2.5 g of anhydrous citric acid, and 0.6 g of trisodium citrate per 1 kg. 7.5 ppm of citral was added to this solution, and 100 g portions were dispensed into retort pouches. To the dispensed solutions, 0.06% by mass of Example 8 (Example 8-1), 0.06% by mass of Example 9 (Example 9-1), 0.06% by mass of Example 10 (Example 10-1), or 0.06% by mass of Example 11 (Example 11-1) was added. The pouches were sealed with a heat sealer while removing air, and sterilized by immersion at 80°C for 10 minutes. After sterilization, each sample was subjected to heat torture at 60°C for 3 days under light shielding. As in Test Example 1, control samples 1 (no additives) and 2 (no additives) were prepared. Each sample after torture was used directly for HPLC measurement. The measurement results are shown as relative values, with the measurement value for sample 2 (no additive) set to 100 (Table 9).

[0068]

[0069] These results demonstrate that coffee silverskin extract is effective in suppressing flavor deterioration, particularly in suppressing the generation of flavor deterioration components derived from citral. By adding or incorporating the flavor deterioration inhibitor of the present invention into food and beverages or flavor compositions, flavor deterioration can be suppressed, and unpleasant sensations caused by off-flavors and off-odors can be reduced.

Claims

1. A flavor degradation inhibitor containing coffee silver skin extract.

2. The flavor degradation inhibitor according to claim 1, which suppresses the generation of flavor degradation components derived from citral.

3. The flavor degradation inhibitor according to claim 2, wherein the flavor degradation component derived from citral is one or more selected from p-cresol and p-methylacetophenone.

4. The flavor degradation inhibitor according to claim 3, wherein the flavor degradation components derived from citral are p-cresol and p-methylacetophenone.

5. The flavor degradation inhibitor according to claim 2, wherein the flavor degradation component derived from citral is one or more selected from photocitral A, photocitral B, epiphotocitral A, and 2-(3-methyl-2-cyclopenten-1-yl)-2-methylpropanal.

6. A fragrance composition containing citral and a flavor deterioration inhibitor according to any one of claims 1 to 5.

7. A food or beverage containing citral and a flavor deterioration inhibitor according to any one of claims 1 to 5.

8. A method for suppressing flavor deterioration, comprising adding or blending a flavor deterioration inhibitor according to any one of claims 1 to 5 into a flavor composition or food or beverage.

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