Method for stabilizing nerol and food and beverage composition

Stabilizing nerol in acidic food compositions through a β-cyclodextrin inclusion complex addresses decomposition issues, enhancing stability and sensory qualities.

JP7888844B1Active Publication Date: 2026-07-13ASAHI GRP HLDG LTD
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Patent Information

Application Number
JP2025200829
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2025-07-25
Filing Date
2025-11-20
Publication Date
2026-07-13
Estimated Expiration
2045-11-20

AI Technical Summary

Technical Problem

Nerol decomposes with reduced stability in acidic aqueous solutions, posing challenges for its application in food compositions.

Method used

A food or drink composition containing nerol and β-cyclodextrin with a pH of 5 or less, where the molar content ratio of β-cyclodextrin to nerol is between 1 and 20, and the nerol content is 1 to 75 mg, stabilizes nerol by forming an inclusion complex.

Benefits of technology

The stability of nerol is enhanced in acidic environments, improving the flavor, aroma, and refreshing sensation of food and beverage compositions, allowing for broader applications.

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Abstract

The present invention provides a method for stabilizing nerol and a food and beverage composition containing stabilized nerol. [Solution] The method for stabilizing nerol involves contacting a composition containing nerol and having a pH of 5 or less with β-cyclodextrin. The molar ratio of β-cyclodextrin to nerol may be between 1 and 20. The food and beverage composition contains nerol and β-cyclodextrin and has a pH of 5 or less.
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Description

Technical Field

[0001] The present invention relates to a method for stabilizing nerol and a food or drink composition.

Background Art

[0002] Neroli essential oil extracted from the flowers of bitter orange, an evergreen tree of the Rutaceae family, is said to calm anxiety, soothe the mind, and provide a deep sense of relaxation. Nerol, a component of neroli essential oil, is a colorless liquid with a sweet fragrance like that of roses and is used as a fragrance. Nerol is also collected from lemongrass, hops, etc. in addition to neroli essential oil. For example, Patent Document 1 describes an activity enhancer containing nerol as an active ingredient.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, it has been found that nerol decomposes with reduced stability in an acidic aqueous solution, and there are problems in its application to food compositions. One aspect of the present invention aims to provide a method for stabilizing nerol and a food or drink composition containing stabilized nerol.

Means for Solving the Problems

[0005] A first aspect is a food or drink composition containing nerol and β-cyclodextrin and having a pH of 5 or less. In the food or drink composition, the molar content ratio of β-cyclodextrin to nerol may be 1 or more and 20 or less. Also, the content of nerol in the food or drink composition may be 1 mg or more and 75 mg or less. Further, in the food or drink composition, nerol may be included in β-cyclodextrin.

[0006] The second embodiment is an inclusion body containing nerol and β-cyclodextrin.

[0007] The third embodiment is a method for stabilizing nerol, comprising contacting a composition containing nerol and having a pH of 5 or less with β-cyclodextrin. In the stabilization method, the molar ratio of the β-cyclodextrin to the nerol may be between 1 and 20. The composition may also contain 1 mg to 75 mg of nerol.

[0008] A fourth aspect is a method for producing the food and beverage composition of the first aspect, comprising contacting nerol with β-cyclodextrin. [Effects of the Invention]

[0009] According to one aspect of the present invention, a method for stabilizing nerol and a food and beverage composition containing stabilized nerol can be provided. [Brief explanation of the drawing]

[0010] [Figure 1] This figure shows the relationship between pH and the remaining percentage of nerol. [Figure 2] This figure shows the relationship between the type of cyclodextrin and the remaining nerol content. [Figure 3] This figure shows the relationship between the remaining percentages of cluster dextrin and nerol. [Figure 4] This figure shows the stabilizing effect of β-cyclodextrin on nerol. [Figure 5] This figure shows the relationship between the amount of β-cyclodextrin added and the remaining percentage of nerol. [Modes for carrying out the invention]

[0011] In this specification, the content of each component in a composition refers to the total amount of multiple substances present in the composition, unless otherwise specified, if multiple substances corresponding to each component are present in the composition. Furthermore, the upper and lower limits of the numerical ranges described herein can be arbitrarily selected and combined from the numerical values ​​exemplified as numerical ranges. Embodiments of the present invention will now be described in detail. However, the embodiments shown below are illustrative of a method for stabilizing nerol and a food and beverage composition for realizing the technical concept of the present invention, and the present invention is not limited to the method for stabilizing nerol and the food and beverage composition shown below.

[0012] Stabilization method for nerol The method for stabilizing nerol involves contacting a composition containing nerol and having a pH of 5 or less with β-cyclodextrin. It has been found that nerol's stability decreases and it decomposes in an acidic environment with a pH of 5 or less. However, the presence of β-cyclodextrin suppresses decomposition and improves the stability of nerol in an acidic environment. This can be attributed, for example, to the formation of an inclusion complex between nerol and β-cyclodextrin.

[0013] β-cyclodextrin is a type of cyclic oligosaccharide in which seven D-glucose molecules are linked together by α-1,4-glycosidic bonds to form a cyclic structure. The interior of the cyclic structure of β-cyclodextrin is a void, with an inner diameter of 0.6 nm to 0.8 nm. Since the hydroxyl groups of the D-glucose that make up β-cyclodextrin are located outside this void, the interior of the void is hydrophobic and can encapsulate hydrophobic molecules.

[0014] Nerol is a monoterpene found in essential oils extracted from lemongrass, hops, and other plants. Its IUPAC name is (Z)-3,7-dimethyl-2,6-octadien-1-ol (CAS number 106-25-2). Nerol is the cis isomer of geraniol. Nerol is said to have a weaker rose scent than geraniol and possesses a fresh, seaside aroma. Nerol is used in combination with geraniol in floral fragrance blends and as a food flavoring.

[0015] In Japan, nerol is treated as a food product, not a pharmaceutical, and is classified as a designated food additive (No. 1923) in the category of aliphatic higher alcohols (Category 7). The lowest no-observed-adverse-effect level (NOAEL) obtained from animal studies of nerol is 191 mg / kg / day, which is the result of repeated toxicity studies in rats. The acceptable daily intake (ADI) of nerol is calculated to be, for example, 1.91 mg / kg / day, which, assuming an adult weighing 50 kg, is calculated to be 95.5 mg / person / day. Furthermore, there is currently no known information regarding health damage to humans. From the above, it can be said that nerol is a compound whose safety as a food additive is guaranteed.

[0016] For example, as described in International Publication No. 2025 / 023322, nerol has an effect of improving activity, and when included in food and beverage compositions, an improvement in activity can be expected in those who ingest it. Here, an improvement in activity means, for example, that a state of psychological arousal is promoted in the subject. Psychological arousal (hereinafter sometimes simply referred to as arousal) refers to a state of excitement or energy expenditure linked to emotion. Typically, psychological arousal is closely related to a person's evaluation of the importance of an event and the physical intensity of the stimulus. This psychological arousal is also shown by Russell's circumflex model, which posits that emotions are arranged on a two-dimensional plane between the "pleasure-displeasure" axis and the "arousal-sedation" (or "activation-inactivation") axis. It is said that the ascending reticular activating system, which extends from the midbrain reticular formation to the cerebrum, is involved in maintaining a state of psychological arousal. Subjective evaluation results of the promotion of a state of psychological arousal include, for example, the suppression of lethargy and the promotion of mood elevation. Improving the stability of nerol in food and beverage compositions makes it easier to expand the range of applications for nerol in food and beverage compositions.

[0017] In the method for stabilizing nerol, the nerol contained in the composition can be stabilized by contacting a composition containing nerol and having a pH of, for example, 5 or less, with β-cyclodextrin. The method of contacting the nerol-containing composition with β-cyclodextrin is not particularly limited as long as it allows nerol and β-cyclodextrin to come into contact. For example, β-cyclodextrin may be added to the nerol-containing composition and brought into contact, or the nerol-containing composition and the β-cyclodextrin-containing composition may be mixed and brought into contact, or nerol may be added to a composition containing β-cyclodextrin and having a pH of 5 or less and brought into contact.

[0018] The pH of the composition containing nerol may be, for example, 2 or more and 5 or less, preferably 2.5 or more and 4.8 or less, more preferably 2.8 or more and 4.6 or less, still more preferably 3 or more and 4.5 or less, 3.3 or more, 3.4 or more, or 3.6 or more, or 4.3 or less, 4.2 or less, or 4.0 or less. The content of nerol contained in the composition may be, for example, 1 mg or more and 75 mg or less, preferably 2 mg or more, 5 mg or more, or 10 mg or more, and may be 50 mg or less, 40 mg or less, 30 mg or less, 25 mg or less, or 20 mg or less. Further, the content ratio of nerol in the composition may be, for example, 1 ppm or more and 200 ppm or less, 5 ppm or more and 125 ppm or less, or 5 ppm or more and 100 ppm or less, based on the total amount of the composition, preferably 10 ppm or more, or 20 ppm or more, and preferably 60 ppm or less, 50 ppm or less, 40 ppm or less, 35 ppm or less, or 25 ppm or less. Note that the content ratio of nerol in the composition is a value based on mass.

[0019] In the method for stabilizing nerol, by contacting nerol with β-cyclodextrin, it is considered that, for example, nerol is encapsulated by β-cyclodextrin and stabilized. Also, it is considered that by encapsulating nerol with β-cyclodextrin, the aroma, flavor, etc. of nerol can be masked or partially masked. In the method for stabilizing nerol, the amount of β-cyclodextrin to be contacted with nerol may be, as the molar ratio of β-cyclodextrin to nerol, for example, an amount that is 1 or more and 20 or less, preferably 2 or more, or 3 or more, and also preferably 15 or less, or 10 or less. The contact temperature of nerol and β-cyclodextrin may be, for example, 0°C or more and 30°C or less, preferably 0°C or more and 25°C or less, or 5°C or more and 20°C or less.

[0020] Compositions containing nerol may contain at least water and may also contain other components in addition to nerol. Compositions containing nerol may, for example, contain edible components to constitute food and beverage compositions. That is, the method for stabilizing nerol may be a method for stabilizing nerol in food and beverage compositions containing nerol, or may be a method for producing food and beverage compositions containing stabilized nerol.

[0021] Food and beverage composition The food and beverage composition contains nerol and β-cyclodextrin in addition to edible components. The pH of the food and beverage composition may be 5 or less. In food and beverage compositions with a low pH, the stability of the contained nerol decreases and the decomposition reaction of nerol proceeds. However, by containing β-cyclodextrin, the stability of nerol in the food and beverage composition is improved and the decomposition reaction of nerol is suppressed. Also, by containing β-cyclodextrin, the aroma, flavor, etc. of nerol in the food and beverage composition can be masked or partially masked. As a result, compared to the case where β-cyclodextrin is not contained, the flavor, taste, aftertaste, residual taste, refreshing feeling, etc. are improved, and a food and beverage composition with a good flavor can be obtained as a comprehensive evaluation. In the food and beverage composition, the stabilized nerol may be encapsulated in β-cyclodextrin.

[0022] The pH of the food and beverage composition may be, for example, 2 to 5, preferably 2.5 to 4.8, more preferably 2.8 to 4.6, even more preferably 3 to 4.5, 3.3 or higher, 3.4 or higher, or 3.6 or higher, or 4.3 or lower, 4.2 or lower, or 4.0 or lower. The nerol content in the food and beverage composition may be, for example, 1 mg to 75 mg per serving, preferably 2 mg or higher, 5 mg or higher, or 10 mg or higher, or 50 mg or lower, 40 mg or lower, 30 mg or lower, 25 mg or lower, or 20 mg or lower. Furthermore, the nerol content in the food and beverage composition may be, for example, 1 ppm to 200 ppm, 5 ppm to 125 ppm, or 5 ppm to 100 ppm relative to the total amount of the food and beverage composition, preferably 10 ppm or more, or 20 ppm or more, preferably 60 ppm or less, 50 ppm or less, 40 ppm or less, 35 ppm or less, or 25 ppm or less. Note that the nerol content in the food and beverage composition is a value based on mass.

[0023] The content of β-cyclodextrin in the food and beverage composition may be, for example, 1 to 20 as a molar ratio to the content of nerol, preferably 2 or more, or 3 or more, and preferably 15 or less, or 10 or less. Furthermore, the content of β-cyclodextrin in the food and beverage composition may be, for example, 0.005% by mass or more and 1% by mass or less, preferably 0.01% by mass or more, 0.04% by mass or more, 0.06% by mass or more, or 0.08% by mass or more, preferably 0.8% by mass or less, 0.6% by mass or less, 0.4% by mass or less, 0.3% by mass or less, 0.2% by mass or less, 0.15% by mass or less, or 0.1% by mass or less, based on the total amount of the food and beverage composition.

[0024] Food and beverage compositions containing nerol may preferably be functional foods and beverages. "Functional foods and beverages" means foods and beverages that have a certain function on living organisms, and include, for example, health functional foods and beverages including Foods for Specified Health Uses (including conditionally designated FOSHU [Foods for Specified Health Uses]) and Foods for Nutrient Function, foods for special uses, nutritional supplements, health supplements, supplements (in various dosage forms such as tablets, coated tablets, sugar-coated tablets, capsules and liquids), and beauty foods and beverages (e.g., diet foods and beverages), and all so-called health foods and beverages. Functional foods and beverages also include health foods to which health claims based on Codex Alimentarius (FAO / WHO Joint Food Standards Committee) food standards apply.

[0025] Examples of food and beverage compositions are not particularly limited, but include health foods and beverages in the form of tablets, chewable tablets, powders, capsules, granules, and drinks (supplements, nutritional supplements, health foods, nutritional adjustment foods, etc.), soft drinks, tea drinks, jelly drinks, sports drinks, coffee drinks, carbonated drinks, vegetable drinks, fruit juice drinks, fermented vegetable drinks, fermented fruit juice drinks, fermented milk drinks (yogurt, etc.), lactic acid bacteria drinks, milk drinks, powdered drinks, cocoa drinks, confectionery (e.g., biscuits and cookies, chocolate, candy, chewing gum, gummies, tablets), and jelly.

[0026] The food and beverage composition may be a fluid beverage or a soft drink. If the food and beverage composition is a beverage, the nerol concentration in the beverage may be, for example, 1 ppm to 200 ppm, 5 ppm to 125 ppm, or 5 ppm to 100 ppm, preferably 10 ppm or more, 15 ppm or more, or 20 ppm or more, preferably 60 ppm or less, 50 ppm or less, 40 ppm or less, 35 ppm or less, or 25 ppm or less.

[0027] The beverage is composed of, for example, nerol and a liquid medium such as water or fruit juice. The beverage may be, for example, tea beverages such as green tea, oolong tea and black tea, soft drinks, jelly drinks, sports drinks, milk drinks, carbonated drinks, vegetable drinks, fruit juice drinks, fermented vegetable drinks, fermented fruit juice drinks, fermented milk drinks (such as yogurt), lactic acid bacteria drinks, milk drinks (such as coffee milk and fruit milk), powdered drinks, cocoa drinks, alcoholic beverages, non-alcoholic beverages (for example, non-alcoholic beer and non-alcoholic sours), and may be a beverage containing the composition and using milk, purified water, etc. as the liquid medium.

[0028] Food and beverage compositions may contain sweeteners. The inclusion of sweeteners allows for easy adjustment to the desired level of sweetness. The sweetener may be sugar, and is not particularly limited to commonly used sugars, such as sucrose, glucose, fructose, fructooligosaccharides, and galactooligosaccharides. Alternatively, commonly used synthetic sweeteners such as aspartame and saccharin may be added instead of sugar. These may be used individually or in combination of two or more.

[0029] Food and beverage compositions may contain acidulants. The acidulants are not particularly limited as long as they are commonly used, and examples include citric acid, malic acid, acetic acid, tartaric acid, glucono delta-lactone, gluconic acid, phosphoric acid, succinic acid, ascorbic acid, phytic acid, lactic acid, carbonic acid, or their salts (sodium salt, calcium salt, or magnesium salt, etc.). These may be used individually or in combination of two or more.

[0030] When a food and beverage composition contains an acidulant, the amount of acidulant in the food and beverage composition may be, for example, 0.01% by mass or more and 1% by mass or less, preferably 0.02% by mass or more, 0.04% by mass or more, 0.06% by mass or more, or 0.08% by mass or more, preferably 0.8% by mass or less, 0.6% by mass or less, 0.4% by mass or less, 0.2% by mass or less, or 0.15% by mass or less, based on the total amount of the food and beverage composition.

[0031] Food and beverage compositions may contain flavorings. The flavorings are not particularly limited as long as they are commonly used, and examples include citrus oils such as lemon, lime, and orange, orange oil, and herbal extracts. The flavorings may be natural or synthetic. Natural flavorings are not particularly limited as long as they are commonly used, and examples include anise oil, angelica oil, allspice oil, orange oil, cassia oil, capsicum oil, guarana extract, cardamom oil, caraway oil, cumin oil, clary sage oil, grapefruit oil, clove oil, coriander oil, coffee oil, cognac oil, cola nut extract, cinnamon oil, ginger oil, thyme oil, nutmeg oil, peppermint oil, vanilla extract, bitter almond oil, fenugreek oil, fennel oil, pepper oil, peppermint oil, perilla oil, bergamot oil, mandarin oil, eucalyptus oil, lemon oil, and rosemary oil. You may use only one of these, or you may use two or more in combination.

[0032] The synthetic fragrances are not particularly limited as long as they are commonly used synthetic fragrances, and examples include allyl caproate, γ-undecalactone, ethyl vanillin, ethyl butyrate, ethylphenylglycidate, eugenol, geraniol, diacetyl, cyclotene, cinnamic aldehyde, terpineol, δ-decalactone, decanal, nonanal, γ-nonalactone, furaneol, furfuryl mercaptan, 2-hexenal, 3-hexenol, heliotropin, perillaldehyde, benzaldehyde, maltol, methyl anthranilate, methyl salicylate, menthol, α-ionone, linalool, etc.

[0033] Food and beverage compositions may contain coloring agents. The coloring agents are not particularly limited to those commonly used, such as caramel coloring. One type of coloring agent may be used, or two or more may be used in combination.

[0034] Food and beverage compositions may contain antioxidants. The antioxidants used are not particularly limited to those commonly used, and examples include L-ascorbic acid and tocopherol. These may be used individually or in combination of two or more.

[0035] Food and beverage compositions may contain pH adjusters. The pH adjuster is not particularly limited to any commonly used pH adjuster, such as phosphoric acid or lactic acid. These may be used individually or in combination of two or more.

[0036] Method for manufacturing food and beverage compositions A food and beverage composition containing nerol and β-cyclodextrin, with a pH of 5 or less, can be produced by, for example, the following manufacturing method. The manufacturing method of the food and beverage composition may include contacting nerol and β-cyclodextrin. Contact between nerol and β-cyclodextrin in the manufacturing method of the food and beverage composition may be included in any step of the manufacturing process of the food and beverage composition. Furthermore, the method of contacting nerol and β-cyclodextrin is not particularly limited as long as it allows nerol and β-cyclodextrin to interact. For example, β-cyclodextrin may be added to a composition containing nerol (e.g., a food and beverage ingredient) and brought into contact; nerol may be added to a composition containing β-cyclodextrin (e.g., a food and beverage ingredient) and brought into contact; a composition containing nerol and a composition containing β-cyclodextrin may be mixed and brought into contact; or nerol and β-cyclodextrin may be brought into contact directly or in a suitable liquid medium. After contacting nerol and β-cyclodextrin, the mixture may be powdered by freeze-drying or the like. Furthermore, the contact temperature may be low, for example, between 0°C and 10°C, or near room temperature (for example, between 15°C and 25°C). The contact time may be, for example, between 5 minutes and 24 hours, or between 0.5 hours and 24 hours.

[0037] The pH of the food and beverage composition may be adjusted to pH 5 or below after contact between nerol and β-cyclodextrin, or it may be adjusted to pH 5 or below by contacting nerol and β-cyclodextrin in a food and beverage ingredient with a pH of 5 or below.

[0038] The invention relating to this disclosure may encompass, for example, the following embodiments: [1] A food or beverage composition comprising nerol and β-cyclodextrin, with a pH of 5 or less. [2] The food and beverage composition according to [1], wherein the molar content ratio of β-cyclodextrin to nerol is 1 or more and 20 or less. [3] The food and beverage composition according to [1] or [2], wherein the nerol content is 1 mg or more and 75 mg or less. [4] A food and beverage composition according to any one of [1] to [3], wherein nerol is encapsulated in β-cyclodextrin. [5] A food and beverage composition according to any one of [1] to [4], further comprising an acidulant. [6] A food or beverage composition according to any one of [1] to [5] having an improved flavor. [7] A food or beverage composition according to any one of [1] to [6] that has a refreshing sensation. [8] Inclusion bodies containing nerol and β-cyclodextrin. [9] A method for stabilizing nerol, comprising contacting a composition containing nerol and having a pH of 5 or less with β-cyclodextrin.

[10] The stabilization method according to [9], wherein the molar ratio of β-cyclodextrin to nerol is 1 or more and 20 or less.

[11] The stabilization method according to [9] or

[10] , wherein the composition contains 1 mg or more and 75 mg or less of nerol.

[12] A method for producing a food or beverage composition according to any one of [1] to [7], comprising contacting nerol with β-cyclodextrin. [Examples]

[0039] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "%" is based on mass.

[0040] Reference example 1 Acidic sugar solutions (final concentration of sucralose 0.03% (w / v), final concentration of citric acid 0.1% to 0.3% (w / v)) were prepared by adjusting the pH to various levels using trisodium citrate, and evaluation samples were prepared by adding a predetermined amount of nerol. After the prepared evaluation samples were kept at 37°C for two weeks, the remaining nerol percentage was evaluated by the following analytical method. The results are shown in Figure 1.

[0041] <Analysis method> The nerol content was measured using a gas chromatograph-tandem mass spectrometer (GC-MS / MS) under the following conditions: Dichloromethane extraction was performed as a pretreatment. Cyclohexanol was used as an internal standard, and quantification was performed using a standard calibration curve.

[0042] (Analysis conditions for GC-MS / MS) • Equipment: GCMS-TQ8040 (Shimadzu Corporation) • Column: DB-WAX UI (30m x 0.25mm, film thickness 0.25μm) (manufactured by Agilent Technologies) • Injection method: Splitless Carrier gas: He (1.2 mL / min) • Temperature increase program: 40°C (held for 5 minutes) → 10°C / min → 250°C (held for 7 minutes) • Ionization method: EI Ion source temperature: 200℃

[0043] Figure 1 shows that the residual rate of nerol decreases at pH 5 and below, indicating that the stability of nerol decreases as the pH decreases.

[0044] Test Example 1 Powders were obtained by freeze-drying aqueous mixtures of α-cyclodextrin (manufactured by Nippon Shokuhin Kako Co., Ltd.; αCD), β-cyclodextrin (manufactured by Nippon Shokuhin Kako Co., Ltd.; βCD), or γ-cyclodextrin (manufactured by Nippon Shokuhin Kako Co., Ltd.; γCD) and nerol (manufactured by Sigma-Aldrich). Evaluation samples were prepared by adding each powder to an acid-sugar solution adjusted to pH 2.8 so that the nerol concentration reached approximately 30 ppm. The prepared evaluation samples were kept at 37°C for two weeks, and the remaining nerol percentage was evaluated. Cyclodextrins were not added to the control. The results are shown in Figure 2.

[0045] As shown in Figure 2, α-cyclodextrin and γ-cyclodextrin did not show a nerol-stabilizing effect, while only β-cyclodextrin showed a nerol-stabilizing effect.

[0046] Test Example 2 To an acid-sugar solution adjusted to pH 2.8, nerol (final concentration 30 ppm) and either β-cyclodextrin (manufactured by Nippon Shokuhin Kako Co., Ltd.; βCD) or cluster dextrin (manufactured by Glico Nutrition Foods Co., Ltd.; KD) at a concentration of 2% (w / v) each were added to prepare evaluation samples. After holding the prepared evaluation samples at 60°C for 18 hours, the residual rate of nerol was evaluated. Dextrins were not added to the control. The results are shown in Figure 3.

[0047] As shown in Figure 3, cluster dextrin did not exhibit any nerol stabilizing effect.

[0048] Test Example 3 200 mL of acid-sugar solutions adjusted to various pH levels were prepared, and evaluation samples were created by adding nerol (final concentration 30 ppm) and 0.066% (w / v) β-cyclodextrin. The prepared evaluation samples were stored at 37°C for 1.5 months, and the residual rate of nerol was evaluated. β-cyclodextrin was not added to the control. The results are shown in Figure 4.

[0049] As shown in Figure 4, under acidic conditions with a pH of 5 or lower, the addition of β-cyclodextrin improved the retention rate of nerol.

[0050] Test Example 4 To 200 mL of an acid-sugar solution adjusted to pH 3.85, nerol (final concentration 30 ppm) and various amounts (%(w / v)) of β-cyclodextrin (manufactured by Nippon Shokuhin Kako Co., Ltd.; βCD) were added to prepare evaluation samples. After the prepared evaluation samples were held at 60°C for 3 days, the remaining percentage of nerol was evaluated. The results are shown in Figure 5.

[0051] As shown in Figure 5, the residual rate of nerol improved with increasing amounts of βCD added (from 0% (w / v) to approximately 0.45% (w / v)).

[0052] Example 1 To 200 mL of water to which 0.1% (w / v) citric acid was added, nerol (final concentration 30 ppm) and β-cyclodextrin (βCD; final concentration 0.1% (w / v)) were added and dissolved. The pH was then adjusted to 3.8 with trisodium citrate to prepare the test beverage of Example 1. The specific gravity of the prepared test beverage was 1 g / cm³. 3 That was the case.

[0053] Comparative Example 1 Comparative Example 1 was prepared in the same manner as in Example 1, except that β-cyclodextrin was not added.

[0054] Comparative Example 2 Comparative Example 2's test beverage was prepared in the same manner as in Example 1, except that nerol was not added.

[0055] Example 2 The test beverage for Example 2 was prepared in the same manner as in Example 1, except that the final concentration of β-cyclodextrin was set to 0.2% (w / v).

[0056] Example 3 The test beverage for Example 3 was prepared in the same manner as in Example 1, except that the final concentration of β-cyclodextrin was set to 0.05% (w / v).

[0057] evaluation The sensory evaluation of the test beverages manufactured as described above was conducted by four professional evaluators with more than three years of experience in sensory evaluation. Prior testing was conducted with the professional evaluators to ensure there were no significant discrepancies in their scores. The evaluation items, based on JIS Z8144:2004, included flavor, mouthfeel, body, acidity, bitterness, saltiness, sweetness, astringency, aftertaste, freshness, aroma (before drinking), and aroma (immediately after drinking). A comprehensive evaluation was also conducted. The professional evaluators tasted each test beverage and scored them based on the following evaluation criteria, with the score for each evaluation item in Comparative Example 1 (also called the standard product) being set at 3. The arithmetic mean of the scores was calculated for each evaluation item. Furthermore, a paired t-test was conducted between the standard product and each test beverage other than the standard product. The evaluation results are shown in Table 1. In Table 1, "-" indicates no additives were added. In the overall evaluation, the balance of taste and aroma was compared to a standard product, and a score was assigned. For "pleasant mouthfeel" and "pleasant aftertaste / lingering flavor," a higher score indicated that the product was better than the standard product.

[0058] Evaluation Criteria 1: Much weaker than the standard product. 2: Slightly weaker than the standard product. 3: Equivalent to standard products. 4: Slightly stronger than the standard product. 5: Much stronger than the standard product.

[0059] [Table 1]

[0060] As shown in Table 1, food and beverage compositions containing nerol and β-cyclodextrin showed improved flavor, mouthfeel, aftertaste, and refreshing sensation in sensory evaluation, and were superior in overall flavor evaluation.

Claims

1. It contains nerol and β-cyclodextrin, and has a pH of 5 or less. The nerol content is between 5 ppm and 100 ppm. A beverage composition having a molar content ratio of β-cyclodextrin to nerol of 1 to 20.

2. The beverage composition according to claim 1, wherein the molar content ratio of β-cyclodextrin to nerol is 2 or more and 10 or less.

3. The beverage composition according to claim 1, wherein the nerol content is 1 mg or more and 75 mg or less.

4. The beverage composition according to claim 1, wherein nerol is encapsulated in β-cyclodextrin.

5. The beverage composition according to claim 1, further comprising an acidulant.

6. The beverage composition according to claim 1, having an improved flavor.

7. A beverage composition according to claim 1, having a refreshing sensation.

8. The beverage composition according to claim 1, wherein the nerol content is 10 ppm or more and 60 ppm or less.

9. The beverage composition according to claim 1, which contains nerol as an active ingredient and is used to improve activity.

10. The method involves contacting a composition containing nerol and having a pH of 5 or less with β-cyclodextrin. The above composition has a nerol content of 5 ppm or more and 100 ppm or less. A method for stabilizing nerol, wherein the molar ratio of β-cyclodextrin to nerol in contact with nerol is between 1 and 20.

11. The stabilization method according to claim 10, wherein the molar ratio of the β-cyclodextrin to nerol that is brought into contact is 2 or more and 10 or less.

12. The stabilization method according to claim 10, wherein the composition contains 1 mg or more and 75 mg or less of nerol.

13. The stabilization method according to claim 10, wherein the composition has a nerol content of 10 ppm or more and 60 ppm or less.

14. A method for producing a beverage composition according to any one of claims 1 to 9, comprising contacting nerol with β-cyclodextrin.

Citation Information

Patent Citations

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  • Lemon-grass oil clathrate compound and production thereof

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  • Health food

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  • Solid consumer product composition containing cyclodextrin complex having small particle diameter

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  • Perfume powder and method of producing the same

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