Fragrance composition and method for preparing same

Abstract

To provide an aroma composition that has overall flavor / balance and ease of drinking / ease of eating, etc., and to provide a food / beverage containing the same.SOLUTION: By quickly freezing a plant or a plant water extract with a cryogen, pulverizing the frozen product while still frozen, and extracting the pulverized product with an organic solvent, the aroma component is not changed and the aroma originally possessed by plants such as fruits can be obtained.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a fragrance composition and a method for preparing the same, which is prepared by subjecting a plant or a water extract of the plant to quick-freezing treatment with a cryogen and then extracting the plant with an organic solvent. [Background technology]

[0002] Extraction and distillation are commonly used to separate aromas, which are volatile components, from plants or plant aqueous extracts. Extraction and distillation techniques include Soxhlet extraction, simultaneous distillation extraction (SDE), continuous liquid-liquid extraction, and solvent extraction (Non-Patent Documents 1 and 2). When these techniques are applied to plants or plant aqueous extracts, the aroma of the sample can change during the process. This is due to the effects of heat applied during the process, enzymes and oils contained in the sample, and oxygen in the air. For this reason, it is difficult to extract aromas from plants or plant aqueous extracts while maintaining their inherent aroma. However, there are many products out there that claim to be fresh and authentic, suggesting there is a demand for them. Inventions involving low-temperature extraction to overcome heat-induced changes have been reported (Patent Documents 1 and 2). However, these documents are aimed at the production of foods and beverages, and are not method inventions for exploring the original aroma composition of plants or plant water extracts. There is also a known method of crushing plants and food by lowering the temperature with a cryogen (Non-Patent Document 3). However, the method in this document is intended for use in analyzing pesticide residues in food. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. WO2006 / 009252 [Patent Document 2] International Publication No. WO2007 / 083812 [Non-patent literature]

[0004] [Non-Patent Document 1] Food Analysis (Sample Analysis Course), Japan Society for Analytical Chemistry (ed.), Maruzen Publishing, pp. 32-45, September 2011 [Non-patent document 2] C. Wu, F. Wang, J. Liu, Y. Zou, X. Chen, Integr. Med. Res., 4, 171-177, 2015 [Non-patent document 3] "Dry ice freezing and crushing equipment", [online], [searched February 5, 2021], Internet<URL: http: / / www.aisti.co.jp / product / dryice_set / > Summary of the Invention [Problem to be solved by the invention]

[0005] The object of the present invention is to provide a flavor composition that has a well-balanced overall flavor, is easy to drink, is easy to eat, etc., and to provide foods and beverages containing the same. [Means for solving the problem]

[0006] As a result of investigations aimed at solving the above-mentioned problems, the inventors have found that aroma components can be extracted without being altered by flash-freezing a plant or a water extract of a plant with a cryogen, pulverizing the frozen product while it is still frozen, and then extracting the pulverized product with an organic solvent.

[0007] The present invention includes the following [1] to [8]. [1] A method for extracting aroma components, in which a plant or a water extract of a plant is frozen by adding a refrigerant, crushed, and then the crushed product is extracted with an organic solvent while maintaining the temperature low. [2] The method according to [1] above, wherein the cryogen is liquid nitrogen or dry ice. [3] The method according to [1] or [2] above, wherein the temperature during extraction is -5°C or lower. [4] The method according to any one of [1] to [3] above, wherein the organic solvent is one or a mixture of two or more selected from dichloromethane, chloroform, dimethyl ether, diethyl ether, ethyl acetate, pentane, hexane, methanol, ethanol, propanol, and isopropanol. [5] The method according to any one of [1] to [4], wherein the plant part is a fruit or a flower. [6] The method according to any one of [1] to [4] above, wherein the aqueous extract of a plant is an aqueous extract of roasted coffee beans. [7] A method for preparing a fragrance composition using information on the fragrance components extracted by the method according to any one of [1] to [6] above. [8] A fragrance composition obtained by the preparation method of [7] above. [Effects of the Invention]

[0008] The present invention enables the extraction of aroma components without impairing the plant's inherent aroma. Furthermore, the extract obtained by the present invention can be used as a fragrance, or detailed analysis of the extract can enable the development of fragrances that have the plant's inherent aroma. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention is described in detail below. The present invention comprises a step of quick-freezing, a step of pulverizing the frozen product, and a step of extracting the pulverized frozen product with an organic solvent at low temperature to obtain an extract of aroma components. The plant parts used in the present invention include mainly fruit, flower and seed parts.Specific plant parts include akebia, acerola, avocado, apricot, strawberry, fig, plum, yellow peach, orange, persimmon, quince, citrus fruits, kiwi fruit, kiwano, chestnut, guava, grapefruit, citrus fruits, pepper, cherry, pomegranate, Japanese pepper, ginger, watermelon, star fruit, plum, pear, cherimoya, Chinese pear, dragon fruit, durian, Japanese pear, nectarine, pineapple, passion fruit, banana, vanilla, papaya, loquat, grape, blueberry, prune, berries, muscat, quince, mangosteen, mango, mandarin orange, melon, peach, lychee, apple, lemon, Examples of essential oils include teas (green tea, black tea, etc.), coffee beans (green beans, roasted beans, etc.), ambrette seed, immortelle, ylang-ylang, chamomile, osmanthus, camphor tree, clary sage, umbellata, cypress, sandalwood, cedarwood, Siberian fir, jasmine, juniper berry, sweet marjoram, sage, geranium, tea tree, neroli, patchouli, mint, palmarosa, cypress, Japanese cypress, fennel, petitgrain, frankincense, vetiver, holy leaf, myrrh, mint, eucalyptus, ravensara, lavender, litsea cubeba, lemongrass, lemon balm, rose, and rosemary. Preferred examples include, but are not limited to, watermelon, grapes, peaches, apples, coffee, etc. In the case of tea and coffee, water extracts thereof are preferred, and the temperature of water used to obtain the water extract is preferably 20 to 100°C.

[0010] In the method for extracting aroma components of the present invention, first, a plant or a water extract of a plant is rapidly frozen using a freezing agent. Examples of freezing agents that can be used include dry ice and liquid nitrogen, with dry ice being preferred. The freezing time is 5 seconds to 5 minutes, preferably 10 seconds to 1 minute. The next step, pulverizing the frozen material, involves placing the frozen material in a blender equipped with insulating materials and pulverizing it. The presence of dry ice during pulverization can prevent the temperature from rising. The pulverization time is 5 seconds to 1 minute, preferably 10 to 30 seconds, and the pulverization temperature is -78°C to -55°C.

[0011] The crushed product obtained by freeze-pulverization is then extracted with an organic solvent. Examples of the organic solvent used for extraction include aliphatic hydrocarbons such as pentane, hexane, heptane, and octane, lower alcohols such as methanol, ethanol, propanol, and isopropanol, dialkyl ethers such as dimethyl ether, diethyl ether, dipropyl ether, and diisopropyl ether, halogenated aliphatic hydrocarbons such as dichloromethane, chloroform, and dichloroethane, and aliphatic carboxylic acid esters such as methyl acetate, ethyl acetate, methyl formate, and ethyl formate. Diethyl ether, methylene chloride, and pentane are preferred. The extraction temperature with an organic solvent is −55° C. to 5° C., preferably −20° C. to −5° C. The extraction time is 1 to 3 hours.

[0012] The aroma extract obtained by the method of the present invention can be subjected to component analysis using an analytical instrument such as gas chromatography, and the results can be used to prepare a flavor composition.Furthermore, by adding the flavor composition to various foods and beverages, foods and beverages with rich flavors can be obtained. [Example]

[0013] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples. [Measuring equipment] The analytical instruments used in the examples are as follows: <gc fid> Instrument: 7890A GC (Agilent) Column: BC-WAX (GL Sciences) Column dimension: 50 m × 0.25 mm I.D., 0.15 μm df Oven program: 70℃(0 min) → 230℃, 4℃ / min <gc ms> Instrument: GCMS-QP2010 Ultra (Shimadzu) Column: BC-WAX (GL Sciences) Column dimension: 50 m × 0.25 mm ID, 0.15 μm df Oven program: 70℃(0 min) → 230℃, 4℃ / min

[0014] (Example 1) Kyoho grapes Approximately 2 kg of seedless Kyoho grapes (with skin) were mixed with approximately 2.4 kg of powdered dry ice and frozen. After freezing, the grapes and powdered dry ice were crushed in a blender until completely powdered. 3 L of methylene chloride at -20°C and the internal standard nonan-5-one were added and stirred for 3 hours for extraction. From the resulting approximately 1.5 L of extract, nonvolatile components were removed using SAFE (Solvent-Assisted Flavor Evaporation) and dehydrated with sodium sulfate. The dehydrated solution was placed in a 47°C water bath and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further removed to approximately 100 μL under a nitrogen stream to obtain the concentrate.

[0015] (Example 2) Concord Approximately 2 kg of Concord apples (seedless, with skin) were mixed with approximately 2.4 kg of powdered dry ice and frozen. After freezing, the fruit and powdered dry ice were crushed in a blender until completely powdered. 3 L of methylene chloride at -20°C and the internal standard nonan-5-one were added and stirred for 3 hours for extraction. The resulting approximately 1.5 L of extract was distilled to remove nonvolatile components using a SAFE and dehydrated with sodium sulfate. The dehydrated solution was placed in a 47°C water bath and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further evaporated to approximately 100 μL under a nitrogen stream to obtain the concentrate.

[0016] Example 3: Delaware Approximately 2 kg of seedless Delaware berries (with skin) were mixed with approximately 2.4 kg of powdered dry ice and frozen. After freezing, the berries and powdered dry ice were crushed in a blender until completely powdered. 2.5 L of methylene chloride at -20°C and the internal standard nonan-5-one were added and stirred for 3 hours for extraction. The resulting approximately 1 L of extract was distilled to remove nonvolatile components using a SAFE and dehydrated with sodium sulfate. The dehydrated solution was placed in a 47°C water bath and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further evaporated to approximately 100 μL under a nitrogen stream to obtain the concentrate.

[0017] (Comparative Example 1) Kyoho grapes For comparison with Example 1, a Kyoho grape concentrate was prepared using a conventional method as follows. 900 g of salt was added to 3.4 kg of seedless Kyoho grapes (with skin) and blended into a juice. 3 L of methylene chloride and the internal standard nonan-5-one were added to the juice sample and stirred for 2 hours. After extraction, the organic and aqueous layers (including the solid layer) were separated using a centrifuge. The resulting organic layer was dehydrated with sodium sulfate and then concentrated to approximately 200 mL using a Kuderna-Danish concentrator in a water bath at 47 °C. Nonvolatile components were removed from the concentrate using a SAFE and then dehydrated with sodium sulfate. The dehydrated recovered solution was concentrated to approximately 1 mL using a Kuderna-Danish concentrator in a water bath at 47 °C. The solvent was then further evaporated under a nitrogen stream to approximately 100 μL, yielding a concentrate.

[0018] (Comparative Example 2) Concord For comparison with Example 2, a Concord concentrate was prepared using conventional methods as follows. Approximately 900 g of salt was added to 3 kg of Concord apples (seedless, with skin) and blended into a juice. 3 L of methylene chloride and the internal standard nonan-5-one were added to the juice sample and stirred for 2 hours. After extraction, the organic and aqueous layers (including the solid layer) were separated using a centrifuge. The resulting organic layer was dehydrated with sodium sulfate and then concentrated to approximately 200 mL using a Kuderna-Danish concentrator in a water bath at 47°C. Nonvolatile components were removed from the concentrate using a SAFE and then dehydrated with sodium sulfate. The dehydrated recovered solution was concentrated to approximately 1 mL using a Kuderna-Danish concentrator in a water bath at 47°C. The solvent was then further evaporated under a nitrogen stream to approximately 100 μL, yielding a concentrate.

[0019] (Comparative Example 3) Delaware For comparison with Example 3, a Delaware concentrate was prepared using conventional techniques as follows. Approximately 600 g of salt was added to 2.2 kg of seedless Delaware berries (with skin) and blended to a juice-like consistency. 2 L of methylene chloride and the internal standard nonan-5-one were added to the juice-like sample and stirred for 2 hours. After extraction, the organic and aqueous layers (including the solid layer) were separated using a centrifuge. The resulting organic layer was dehydrated over sodium sulfate and then concentrated to approximately 200 mL using a Kuderna-Danish concentrator in a water bath at 47°C. Nonvolatile components were removed from the concentrate using a SAFE and then dehydrated over sodium sulfate. The dehydrated recovered solution was concentrated to approximately 1 mL using a Kuderna-Danish concentrator in a water bath at 47°C. The solvent was then further evaporated under a nitrogen stream to approximately 100 μL, yielding a concentrate.

[0020] (Comparison result 1) The aroma of the extracts obtained in Examples 1 to 3, which are the method of the present invention, was evaluated by a panel of five people. As a result, it was confirmed that all three grape varieties retained the pleasant aroma of eating fresh grapes. The aroma evaluation results of each extract obtained in Examples 1 to 3 and Comparative Examples 1 to 3 are shown in Table 1. Table 2 also shows the area values ​​of C6 compounds in each concentrate, assuming the area values ​​of the internal standards obtained in Examples 1 to 3 and Comparative Examples 1 to 3 to be 10. The amount of C6 compounds, such as hexanal, cis-3-hexenal, trans-2-hexenal, and trans-2-hexenol, extracted in large amounts in Comparative Examples 1 to 3, was reduced by the methods of Examples 1 to 3. This suggests that the secondary production of these C6 compounds was suppressed, allowing the original grape aroma to be extracted.

[0021] [Table 1]

[0022] [Table 2]

[0023] (Example 4) Preparation of a fragrance with a low C6 component content that reflects the results of the method of the present invention and evaluation of the fragrance The effect of the C6 component in the grape-like fragrance on the fragrance was confirmed. A grape-like fragrance composition was prepared according to the formulation of the example in Table 3. The prepared fragrance composition was added to water at 0.1% by mass, and a seven-person panel evaluated the fragrance. All of them responded that it was a pleasant fragrance reminiscent of the natural fragrance of grapes.

[0024] (Comparative Example 4) Preparation of a high C6 content fragrance that reflects the results of conventional methods and evaluation of its fragrance The effect of the C6 component in grape-like fragrance on aroma was confirmed. In the results for Kyoho grapes (Comparative Results 1, Table 2), trans-2-hexenal was detected 67 times more in Comparative Example 1 than in Example 1, and cis-3-hexenol was detected 5 times more in Comparative Example 1 than in Example 1. These results were reflected in the formulation of the comparative example in Table 3, and the comparative example formulation in Table 3 was created, with 67 times more trans-2-hexenal and 5 times more cis-3-hexenol than in the example in Table 3. A grape-like fragrance composition was prepared according to the comparative example formulation. The prepared fragrance composition was added to water at 0.1% by mass, and a seven-person panel evaluated the aroma. All participants found that the original grape aroma was impaired and the flavor was unpalatable.

[0025] [Table 3]

[0026] Example 5: Watermelon Approximately 570 g of watermelon pulp from Obanazawa, Yamagata Prefecture, was mixed with 660 g of powdered dry ice and frozen. After freezing, the pulp and powdered dry ice were crushed in a blender until completely powdered. 1.5 L of methylene chloride at -20°C was added and the mixture was stirred for 3 hours for extraction. The resulting extract was distilled to remove nonvolatile components using a SAFE and then dehydrated with sodium sulfate. The dehydrated liquid was placed in a water bath at 47°C and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further evaporated to approximately 100 μL under a nitrogen stream to obtain the concentrate. The aroma of the extract was evaluated by a panel of five people, and it was confirmed that it had a pleasant aroma reminiscent of the natural aroma of watermelon.

[0027] (Example 6) Peach 500 g of Kawanakajima white peach pulp was mixed with 600 g of powdered dry ice and frozen. After freezing, the pulp and powdered dry ice were crushed in a blender until completely powdered. 1 L of diethyl ether at -20°C was added and the mixture was stirred for 3 hours for extraction. Nonvolatile components were removed from the resulting extract using a SAFE and then dehydrated with sodium sulfate. The recovered solution after dehydration was placed in a 47°C water bath and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further removed to approximately 100 μL under a nitrogen stream to obtain the concentrate. The aroma of the extract was evaluated by a panel of five people, and it was confirmed that it had a fresh, juicy, and pleasant aroma reminiscent of the natural aroma of peaches.

[0028] (Example 7) Coffee 300 g of coffee extract, extracted from roasted and ground Arabica beans with hot water at approximately 95°C, was mixed with 900 g of powdered dry ice and frozen. After freezing, the coffee extract and powdered dry ice were crushed in a blender until completely powdered. 1.5 L of methylene chloride at -20°C was added and the mixture was stirred for 3 hours. The resulting extract was distilled to remove nonvolatile components using a SAFE and dehydrated with sodium sulfate. The dehydrated solution was placed in a water bath at 47°C and concentrated to approximately 1 mL in a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then further evaporated to approximately 100 μL under a nitrogen stream to obtain the concentrate. The aroma of the extract was evaluated by a panel of five people, and it was confirmed that it had a pleasant aroma reminiscent of the aroma of freshly brewed coffee.

[0029] (Example 8) Apple 2 kg of San Fuji fruit pulp was mixed with 2.4 kg of powdered dry ice and frozen. After freezing, the fruit pulp and powdered dry ice were crushed in a blender until everything was powdered. 3 L of methylene chloride at -20°C was added and the mixture was extracted with stirring for 3 hours. The resulting extract was placed in a 47°C water bath and concentrated to approximately 1 mL using a Kuderna-Danish concentrator under a nitrogen atmosphere. The solvent was then distilled off under a nitrogen stream to approximately 100 μL to obtain a concentrate. The aroma of the extract was evaluated by a panel of four people, and it was confirmed that it had a fresh and pleasant aroma reminiscent of the natural scent of apples.< / gc> < / gc>

Claims

1. A method for preparing a fragrance composition by extracting aroma components from a plant or an aqueous extract of the plant using an organic solvent and using gas chromatographic information of the extract, the method comprising: Dry ice is added to freeze the plant or the water extract of the plant, and the plant is then crushed at -78°C to -55°C. While maintaining a temperature of -20℃ to -5℃, A method of extracting with an organic solvent. Method for preparing a fragrance composition.

2. The method according to claim 1, wherein the plant part is a fruit or flower, and the aqueous extract of the plant is an aqueous extract of roasted coffee beans.

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