Composition including plant-derived beta-caryophyllene and method for producing the same

Abstract

The purpose of the present invention is to provide a plant-derived beta-caryophyllene composition that includes plant-derived beta-caryophyllene and has excellent palatability, and from which a variety of safe products can be obtained, as well as a method for producing the same. In this composition including plant-derived beta-caryophyllene, the plant-derived beta-caryophyllene content is 80 wt% or greater, the eugenol content is 0.0455 wt% or less, and the methyl eugenol content is 0.005 wt% or less.

Description

Composition containing plant-derived β-caryophyllene and method for producing the same

[0001] The present invention relates to a composition containing plant-derived β-caryophyllene and a method for producing the same.

[0002] β-Caryophyllene has antibacterial, antioxidant, anti-inflammatory, and other effects, and in recent years has also been used as a food additive (see, for example, the claims of Japanese Patent No. 7056048). Therefore, many products that take advantage of the effectiveness of β-caryophyllene have been put on the market.

[0003] β-Caryophyllene is an essential oil component that is widely found in nature, and is found in large amounts in plants such as cloves, copaiba, pepper, rosemary, and hemp. Therefore, the majority of β-caryophyllene sources are plant-derived. However, it is difficult to isolate β-caryophyllene from plant-derived sources, and β-caryophyllene compositions purified from plant-derived sources contain impurities. These impurities have a strong smell, and as a result, products using plant-derived β-caryophyllene compositions have the problem of being less palatable.

[0004] Furthermore, carcinogenic methyl eugenol could not be completely removed during the purification of plant-derived raw materials. Regarding this issue, IFRA (International Fragrance Association) has evaluated the systemic toxicity of methyl eugenol, and its use standards have become stricter year by year. Currently, methyl eugenol is subject to extremely strict standards requiring residual amounts in final products to be 0.69 ppm or less in multiple categories. However, caryophyllene commercially available worldwide is not standardized for impurity contents of less than 0.1%. Furthermore, products containing less than 0.1% are not usually listed on safety data sheets. Given this background, there are no highly safe β-caryophyllene compositions, and it has been extremely difficult to obtain various products with an increased β-caryophyllene content sufficient to demonstrate the effectiveness of β-caryophyllene.

[0005] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a plant-derived β-caryophyllene composition that contains plant-derived β-caryophyllene and enables the production of various safe and highly palatable products, as well as a method for producing the same.

[0006] To achieve the above object, first, the present inventors investigated the substance causing the strong odor of contaminants in a plant-derived β-caryophyllene composition obtained by purification and identified it as eugenol. Then, they investigated the allowable content of eugenol in a plant-derived β-caryophyllene composition obtained by purification.

[0007] Second, the present inventors investigated the allowable content of methyleugenol in a plant-derived β-caryophyllene composition obtained by purification.

[0008] Third, the present inventors have revealed that clove-derived β-caryophyllene is a suitable source of plant-derived β-caryophyllene.

[0009] The present disclosure has been conceived based on the above research, and includes the following aspects:

[0010] [1] A composition containing plant-derived β-caryophyllene, the composition having a plant-derived β-caryophyllene content of 80% by weight or more, a eugenol content of 0.0455% by weight or less, and a methyleugenol content of 0.005% by weight or less. Here, the "content of plant-derived β-caryophyllene, eugenol, or methyleugenol" refers to the amount of plant-derived β-caryophyllene, eugenol, or methyleugenol contained in the composition.

[0011] [2] The composition according to [1], wherein the plant-derived β-caryophyllene is β-caryophyllene derived from cloves (Cloves).

[0012] [3] A pharmaceutical product, quasi-drug, food or drink, health food, cosmetic, fragrance, air freshener, or daily necessities containing a composition containing β-caryophyllene derived from the plant according to [1] or [2].

[0013] [4] An inhalation liquid for an inhaler or an inhalation assisting device, containing a composition containing β-caryophyllene derived from the plant according to [1] or [2].

[0014] [5] An aroma solution for an aroma diffuser, containing a composition containing β-caryophyllene derived from the plant according to [1] or [2].

[0015] [6] An electronic cigarette liquid containing a composition containing β-caryophyllene derived from the plant according to [1] or [2].

[0016] [7] A method for producing a composition containing plant-derived β-caryophyllene, comprising: filtering a liquid raw material having a plant-derived β-caryophyllene content of 80% by weight or more through a filter, thereby obtaining a filtered liquid composition; adding activated carbon to the filtered liquid composition so that the activated carbon accounts for 3 to 15% by weight of the filtered liquid composition; stirring the activated carbon-added liquid composition for a predetermined period of time, thereby obtaining a stirred liquid composition; and filtering the stirred liquid composition through a filter, thereby obtaining a composition containing plant-derived β-caryophyllene, wherein the plant-derived β-caryophyllene content is 80% by weight or more, the eugenol content is 0.0455% by weight or less, and the methyleugenol content is 0.005% by weight or less. Effect of disclosure

[0017] The present disclosure has the effect of providing a plant-derived β-caryophyllene composition that contains plant-derived β-caryophyllene and enables the production of various safe products that are highly palatable, and a method for producing the same.

[0018] FIG. 1 is a graph showing the changes in the methyleugenol content, the eugenol content, and the total content of methyleugenol and eugenol with respect to the change in the amount (wt %) of activated carbon added in Table 1.

[0019] FIG. 2 is a graph showing the changes in the methyleugenol content, the eugenol content, and the total content of methyleugenol and eugenol with respect to the changes in the amount of activated carbon added (wt %) in Table 1. MODES FOR CARRYING OUT THE DISCLOSURE

[0020] Hereinafter, modes for implementing the above-mentioned aspects [1] to [7] of the present disclosure will be described.

[0021] (Embodiment 1) A composition containing plant-derived β-caryophyllene according to embodiment 1 of the present disclosure is a composition containing 80 wt% or more of plant-derived β-caryophyllene, 0.0455 wt% or less of eugenol, and 0.005 wt% or less of methyleugenol. Here, in a composition containing plant-derived β-caryophyllene, the "content of plant-derived β-caryophyllene, eugenol, or methyleugenol" refers to the amount of plant-derived β-caryophyllene, eugenol, or methyleugenol contained in the composition. In addition, in the composition containing plant-derived β-caryophyllene, plant-derived β-caryophyllene is an active ingredient, and eugenol and methyleugenol are contaminants that are particularly desired to be removed (hereinafter, sometimes referred to as "predetermined components to be removed").

[0022] <Plant-derived β-caryophyllene> Since plant-derived β-caryophyllene is an active ingredient, the higher the content, the greater its effect. The content of plant-derived β-caryophyllene is preferably 80 wt % or more, more preferably 85 wt % or more, and most preferably 97 wt % or more.

[0023] Examples of plants containing β-caryophyllene include cloves (Cloves), cannabis, hemp, cannabis, hops, basil, oregano, pepper, lavender, rosemary, Cinnamon, black caraway, etc. Raw materials containing β-caryophyllene derived from these plants are commercially available as refined oils from those plants.

[0024] <Eugenol> Eugenol is a predetermined target component for removal, and is an odor component that is desired to be removed from raw materials containing plant-derived β-caryophyllene. Therefore, the content of eugenol is preferably 0.0455% by weight or less, more preferably 0.02% by weight or less, and most preferably 0.01% by weight or less.

[0025] <Methyleugenol> Methyleugenol is a predetermined target component for removal and a carcinogen that is desired to be removed from raw materials containing plant-derived β-caryophyllene. Therefore, the content of methyleugenol is preferably 0.005% by weight or less, more preferably 0.002% by weight or less, and most preferably 0.0005% by weight or less.

[0026] The composition containing plant-derived β-caryophyllene according to the first embodiment contains a high amount of the active ingredient β-caryophyllene, a low amount (or no amount) of eugenol, which has a strong odor and adversely affects palatability, and an extremely low amount (or no amount) of methyleugenol, which is carcinogenic. This allows various products to contain a large amount of the active ingredient β-caryophyllene at a level that allows the active ingredient to be effective. As a result, various safe products containing plant-derived β-caryophyllene and having excellent palatability can be obtained.

[0027] Embodiment 2 A composition comprising plant-derived β-caryophyllene according to embodiment 2 of the present disclosure is the composition of embodiment 1, wherein the plant-derived β-caryophyllene is β-caryophyllene derived from cloves (Cloves).

[0028] Clove-derived raw materials can improve the purity of β-caryophyllene and reduce the content of contaminants such as eugenol or methyleugenol at a reduced cost compared to raw materials derived from other plants.

[0029] Plants contain a variety of compounds, and the types and amounts of compounds contained vary depending on the type of plant. The difficulty of separating and purifying compounds varies depending on differences in boiling point, melting point, structural formula, functional group, etc. Compared to other plants, it is easier to separate (remove) β-caryophyllene from impurities in cloves, making it easier to improve the purity of β-caryophyllene.

[0030] (Embodiment 3) A pharmaceutical product, a quasi-drug, a food or drink product, a health food product, a cosmetic product, a flavoring agent, an air freshener, or a daily necessities according to Embodiment 3 of the present disclosure is a product containing a composition comprising β-caryophyllene derived from the plant of Embodiment 1 or Embodiment 2.

[0031] <Pharmaceuticals> Examples of pharmaceuticals include various tablets, powders (powders), granules, pills, capsules, films, drinks, lozenges, and mouthwashes.

[0032] <Quasi-drugs> Examples of quasi-drugs include nutritional supplements, various supplements, oral fresheners, anti-halitosis agents, oral care products, hair care agents, hair growth agents, skin moisturizers, etc. Examples of oral care products include toothpaste (dental paste), liquid toothpaste (dental rinse), mouthwash, chewing gum (containing an anti-cavity ingredient: for example, xylitol), sprays (mouth sprays), etc.

[0033] <Food and Beverage> Examples of foods and beverages include liquid products such as fruit juice, fruit juice drinks, non-fruit juice drinks, vegetable drinks, carbonated drinks, sports drinks, coffee drinks, tea, black tea, oolong tea, mineral drinks, yogurt drinks, dairy drinks, lactic acid bacteria drinks, energy drinks, alcoholic drinks, non-alcoholic drinks, soup, and noodle soup; candy, chewing gum, tablets, gummies, jelly, chocolate, baked goods such as cookies and cakes, cotton candy, bread, ice cream, frozen desserts, ham, sausages, snacks, seasonings such as powdered sauces; oils and fats such as butter and margarine; solid products such as edible sheet foods; and semi-solid and fluid products such as curry, stew, hayashi rice, sauces, dressings, fresh cream, cream, jam, and liquid foods.

[0034] <Health foods> Examples of health foods include foods for specified health uses, foods with efficacy claims, and foods with nutrient functions, which are classified as health functional foods. Other so-called health foods are also included. Here, so-called health foods refer to "foods that are not legally defined, are taken orally other than pharmaceuticals, are sold with the claim that they are particularly useful for maintaining or improving health, or are consumed in the hope of achieving such effects."

[0035] <Cosmetics> Examples of cosmetics include basic cosmetics such as face washes, cleansing agents, lotions, serums, emulsions, and creams, makeup cosmetics such as foundations, eyebrow products, mascara, eyeliners, lipsticks, glosses, blushes, and nail polishes, and sunscreen cosmetics.

[0036] <Fragrance> The composition containing plant-derived β-caryophyllene of Embodiment 1 or Embodiment 2 may be used alone as a fragrance, or may be used together with other fragrance components. Examples of other fragrance components include limonene, α-pinene, β-pinene, α-terpinene, linalool, cedrene, longifolene, and valencene, but other natural fragrances or synthetic fragrances may also be used. The composition containing plant-derived β-caryophyllene of Embodiment 1 or Embodiment 2 may be used together with one or more fragrance components selected from the group of fragrance components described above, or may be used together with one or more fragrance components other than those described above.

[0037] <Air Freshener> Examples of the air freshener include liquid type, jelly / gel type, spray type, and candle type.

[0038] <Daily Necessities> Examples of daily necessities include soap, detergent, shampoo, conditioner, hair treatment, bath additives, and the like.

[0039] The composition containing plant-derived β-caryophyllene according to Embodiment 1 or 2 has a high content of the active ingredient β-caryophyllene, a low content (or no content at all) of eugenol, which has a negative effect on palatability, and an extremely low content (or no content at all) of methyleugenol, which is carcinogenic. This allows pharmaceuticals, quasi-drugs, foods and beverages, health foods, cosmetics, flavors, fragrances, or daily necessities to contain a large amount of the active ingredient plant-derived β-caryophyllene at a level sufficient to demonstrate its effectiveness. As a result, pharmaceuticals and other products containing plant-derived β-caryophyllene that are highly palatable and safe can be obtained.

[0040] (Embodiment 4) An inhalation liquid for an inhaler or an inhalation assisting device according to embodiment 4 of the present disclosure is an inhalation liquid containing a composition comprising β-caryophyllene derived from the plant of embodiment 1 or embodiment 2.

[0041] <Inhalation Liquid> Inhalers using an inhalation liquid include, for example, pressurized spray metered dose inhalers and soft mist metered dose inhalers, and inhalation aids using an inhalation liquid include, for example, spacers and nebulizers.

[0042] The plant-derived β-caryophyllene-containing composition of Embodiment 1 or 2 has a high content of the active ingredient β-caryophyllene, a low content (or no content) of eugenol, which adversely affects palatability, and an extremely low content (or no content) of carcinogenic methyleugenol, thereby enabling an inhalation solution for an inhaler or an inhalation assist device to contain a large amount of the active ingredient β-caryophyllene at a level sufficient to exert its efficacy. As a result, an inhalation solution for an inhaler or an inhalation assist device containing plant-derived β-caryophyllene can be obtained that is safe and has excellent palatability.

[0043] (Embodiment 5) An aroma solution for an aroma diffuser according to embodiment 5 of the present disclosure is an aroma solution containing a composition containing β-caryophyllene derived from the plant of embodiment 1 or embodiment 2.

[0044] <Aroma Solution> Diffusers that use aroma solutions include, for example, reed diffusers, heating diffusers, humidifier-type diffusers, and spray-type diffusers.

[0045] The composition containing plant-derived β-caryophyllene according to Embodiment 1 or 2 contains a high amount of the active ingredient β-caryophyllene, a low amount (or no amount) of eugenol, which has a negative effect on palatability, and an extremely low amount (or no amount) of carcinogenic methyleugenol, making it possible to incorporate a large amount of the active ingredient β-caryophyllene into an aroma solution for an aroma diffuser, sufficient to ensure its effectiveness. As a result, an aroma solution for an aroma diffuser containing plant-derived β-caryophyllene can be obtained that is palatable and safe.

[0046] (Embodiment 6) An electronic cigarette liquid according to embodiment 6 of the present disclosure is a liquid containing a composition comprising β-caryophyllene derived from the plant of embodiment 1 or embodiment 2.

[0047] <Liquid for Electronic Cigarettes> Examples of liquid for electronic cigarettes include liquids that are heated and are used in electronic cigarettes of various types, such as liquid-type, cartridge-type, and disposable types.

[0048] The composition containing plant-derived β-caryophyllene according to Embodiment 1 or 2 has a high content of the active ingredient β-caryophyllene, a low content (or no content) of eugenol, which adversely affects palatability, and an extremely low content (or no content) of carcinogenic methyleugenol, thereby enabling the active ingredient β-caryophyllene to be incorporated into an electronic cigarette liquid in a large amount sufficient to exhibit its efficacy. As a result, an electronic cigarette liquid containing plant-derived β-caryophyllene can be obtained that is both palatable and safe.

[0049] Seventh Embodiment A seventh embodiment of the present disclosure provides a method for producing a composition containing plant-derived β-caryophyllene, comprising: filtering a liquid raw material having a plant-derived β-caryophyllene content of 80% by weight or more through a filter, thereby obtaining a filtered liquid composition; adding activated carbon to the filtered liquid composition so that the activated carbon accounts for 3 to 15% by weight of the filtered liquid composition; stirring the activated carbon-added liquid composition for a predetermined period of time, thereby obtaining a stirred liquid composition; and filtering the stirred liquid composition through a filter, thereby obtaining a composition containing plant-derived β-caryophyllene, wherein the plant-derived β-caryophyllene content is 80% by weight or more, the eugenol content is 0.0455% by weight or less, and the methyleugenol content is 0.005% by weight or less.

[0050] According to this method for producing a composition containing plant-derived β-caryophyllene, a liquid raw material containing 80% or more plant-derived β-caryophyllene is first filtered through a filter selective for the size of suspended solids in essential oil to remove impurities, then an appropriate amount of polar-selective activated carbon is added to remove eugenol and methyleugenol, and the mixture is stirred to promote the removal of eugenol and methyleugenol by the addition of activated carbon. As a result, the β-caryophyllene content of the liquid raw material containing 80% or more plant-derived β-caryophyllene is maintained at 80% or more by weight, the eugenol content is reduced to 0.0455% or less by weight, and the methyleugenol content is reduced to 0.005% or less by weight.

[0051] <Raw Material Study 1> In Raw Material Study 1, Raw Material 1 (80% caryophyllene (raw material: cloves) manufactured by INDESSO) containing 85.7% by weight of clove-derived β-caryophyllene was used as the starting composition. Activated carbon was used as a remover for eugenol and methyleugenol, which are the specified target components for removal.

[0052] [Preparation of Comparative Examples] The sample of Comparative Example 1 was obtained from Raw Material 1 without any treatment.

[0053] The sample of Comparative Example 2 was obtained by filtering the sample of Comparative Example 1 through a 0.5 μm PTFE filter (manufactured by ADVANTEC).

[0054] [Preparation of Examples] For Examples 1 to 3, activated carbon (manufactured by Osaka Gas Chemicals Co., Ltd.) was first added to the sample of Comparative Example 1. The amount of activated carbon added to each sample was 5 wt%, 10 wt%, and 15 wt%. Next, each sample after the activated carbon addition was stirred for 1 hour, for example, using a stirrer (stirring bar). Next, each stirred sample was filtered through a 0.5 μm PTFE filter to obtain the samples of Examples 1 to 3.

[0055] Comparative Example 1: Untreated Comparative Example 2: Filter filtration Example 1: 5% by weight activated carbon + stirring for 1 hour + filter filtration Example 2: 10% by weight activated carbon + stirring for 1 hour + filter filtration Example 3: 15% by weight activated carbon + stirring for 1 hour + filter filtration

[0056] [Evaluation of Preference] 0.1 ml of each sample from each Comparative Example and Example was impregnated into a scent paper (scent test paper (mouette)) about 3 mm wide and about 100 mm long, and a sensory evaluation was carried out by a total of five panelists.

[0057] The odor of Comparative Example 1 was used as the standard (intensity 5) and the odor of each sample was compared with the standard odor to evaluate the odor intensity of each sample.

[0058] [Evaluation Criteria] Intensity 5: Smell of Comparative Example 1 (untreated) Intensity 4: Slightly weak Intensity 3: Weak Intensity 2: Very weak Intensity 1: Almost no smell.

[0059] The final evaluation was based on the average strength values ​​evaluated by the five panelists, and was rated on the following four-point scale.

[0060] [Final evaluation] ◎: 2.0 ≧ average value ≧ 0.0 ○: 2.5 ≧ average value > 2.0 △: 3.5 ≧ average value > 2.5 ×: 5.0 ≧ average value > 3.5 △ or higher indicates a palatability evaluation result

[0061] [Safety Evaluation] The content of each sample was measured as follows: The content of each sample was determined by comparison with the respective standard products using GCMS. GCMS: 7890B-5977B MSD (Agilent Technologies) Column: Inertcap WAX column (length: 60 m, film thickness: 0.25 μm, inner diameter: 0.25 mm (GL Sciences)) Temperature conditions: 240°C for 5 minutes Carrier gas: He Carrier gas flow rate: 1 ml / min Injection method: 1 μl, split 1 / 80 Detection limit: 0.5 ppm Safety evaluation was performed based on the methyleugenol content in the sample, using the following three-level scale: Methyleugenol content (wt%) ◎: 0.00005 or more content ○: 0.005 or more content > 0.00005 ×: content > 0.005 ○ or above indicates passing the safety evaluation. The results of the content measurement, palatability evaluation, and safety evaluation for each sample are shown in Table 1 below.

[0062] The numerical values ​​in Table 1 are in weight percent.

[0063] {Analysis 1} When the raw materials were used as they were, the contents of methyleugenol and eugenol were at levels insufficient for safety and palatability. As the amount of activated carbon added, which is a remover of the specified target components, increased, the contents of methyleugenol and eugenol decreased. When the amount of activated carbon added was 10 wt%, safety and palatability were satisfied. In this case, the methyleugenol content was 0.0048 wt%, the eugenol content was 0.0254 wt%, and the total content of methyleugenol and eugenol was 0.0302 wt%. The β-caryophyllene content did not change even with increasing amounts of activated carbon added. This is presumably because the contents of methyleugenol and eugenol are significantly lower than the β-caryophyllene content, and therefore the effect of this decrease is unlikely to be apparent in the β-caryophyllene content.

[0064] <Raw Material Study 2> In Raw Material Study 2, Raw Material 2 (VAN AROMA's 95% caryophyllene (raw material: cloves)) containing 97.3% by weight of clove-derived β-caryophyllene was used as the starting composition. Activated carbon was used as a remover for eugenol and methyleugenol, which are the target components for removal.

[0065] [Preparation of Comparative Examples] The sample of Comparative Example 3 was obtained from Raw Material 2 without any treatment.

[0066] The sample of Comparative Example 4 was obtained by filtering the sample of Comparative Example 3 through a 0.5 μm PTFE filter.

[0067] [Preparation of Examples] For Examples 4 to 7, activated carbon (manufactured by Osaka Gas Chemicals Co., Ltd.) was first added to the sample of Comparative Example 3. The amount of activated carbon added to each sample was 1 wt%, 3 wt%, 5 wt%, and 15 wt%. Next, each sample after the activated carbon addition was stirred for 1 hour. Next, each stirred sample was filtered through a 0.5 μm PTFE filter to obtain the samples of Examples 4 to 7.

[0068] Comparative Example 3: Untreated Comparative Example 4: Filter filtration Example 4: 1% by weight activated carbon + stirring for 1 hour + filter filtration Example 5: 3% by weight activated carbon + stirring for 1 hour + filter filtration Example 6: 5% by weight activated carbon + stirring for 1 hour + filter filtration Example 7: 15% by weight activated carbon + stirring for 1 hour + filter filtration The results are shown in Table 2 below.

[0069] [Evaluation of Preference] The evaluation criteria were the odor of Comparative Example 3 as the standard (intensity 5), and the odor of each sample was compared with the standard odor to evaluate the odor intensity. Other than that, the conditions were the same as in Raw Material Study 1.

[0070] [Safety Evaluation] The method for measuring the content of the sample and the method for safety evaluation were the same as those in Raw Material Study 1.

[0071] The results of the content measurement, palatability evaluation, and safety evaluation for each sample are shown in Table 2 below.

[0072] The units of values ​​in Table 2 are weight percent. "nd" indicates "below the detection limit (0.00005 or less)."

[0073] {Analysis 2} When the raw materials were used as they were, the contents of methyleugenol and eugenol were at levels insufficient for safety and palatability. As the amount of activated carbon added, which is a remover of the specified target components, increased, the contents of methyleugenol and eugenol decreased. When the amount of activated carbon added was 1 wt%, safety and palatability were satisfied. In this case, the methyleugenol content was 0.0045 wt%, the eugenol content was 0.0373 wt%, and the total content of methyleugenol and eugenol was 0.0418 wt%. The β-caryophyllene content did not change even when the amount of activated carbon added increased.

[0074] <Removal Agent Study 1> In removal agent study 1, raw material 2 was used as the starting composition. Activated clay was used as a removal agent to remove methyleugenol and eugenol, which are the target substances to be removed.

[0075] [Preparation of Comparative Example] As a comparative example, the above-mentioned Comparative Example 3 obtained without processing from Raw Material 2 was used. The results of the palatability evaluation and safety evaluation of Comparative Example 3 are shown in Table 2 above.

[0076] [Preparation of Examples] The palatability evaluation method, content measurement method, and safety evaluation method for Remover Study 1 were the same as those for Raw Material Study 2. The test results for Comparative Example 3 are shown in Table 2. For Examples 9 and 10, the sample of Comparative Example 3 was used as the starting composition, and activated clay (manufactured by Mizusawa Industrial Chemicals) was first added to the sample of Comparative Example 3. The amounts of activated clay added were 5 wt % and 10 wt %. Next, each sample was stirred for 1 hour, and then each stirred sample was filtered through a 0.5 μm PTFE filter to obtain the respective samples.

[0077] Example 9: 5% by weight of activated clay + stirring for 1 hour + filtering Example 10: 10% by weight of activated clay + stirring for 1 hour + filtering The results of content measurement, palatability evaluation, and safety evaluation for each sample are shown in Table 3 below.

[0078] The numerical values ​​in Table 3 are in weight percent.

[0079] {Analysis 3} In this study, the addition of activated clay as a remover hardly reduced the contents of methyleugenol and eugenol, and safety and palatability were not satisfied. In other words, it was found that activated clay has almost no ability to remove eugenol and methyleugenol.

[0080] <Removal Agent Study 2> In removal agent study 2, raw material 2 was used as the starting composition. Furthermore, ethanol was used as a removal agent for methyleugenol and eugenol, which are the target substances to be removed.

[0081] [Preparation of Comparative Example] As a comparative example, the above-mentioned Comparative Example 3 obtained without processing from Raw Material 2 was used. The results of the palatability evaluation and safety evaluation of Comparative Example 3 are shown in Table 2 above.

[0082] [Preparation of Example] The palatability evaluation method, content measurement method, and safety evaluation method for Remover Study 2 were the same as those for Raw Material Study 2. The measurement results for Comparative Example 3 are as shown in Table 2.

[0083] In Example 11, 60% by weight ethanol (twice the weight of the sample) was added to the sample of Comparative Example 3, followed by stirring and washing for 1 hour, and then allowing to stand for 30 minutes. The caryophyllene layer (upper layer) that separated from the ethanol layer (lower layer) was collected and used as a sample.

[0084] In Example 12, twice the weight of the sample of Example 11 was added to 60% by weight of ethanol, and the mixture was stirred and washed for 1 hour, and then allowed to stand for 30 minutes. The caryophyllene layer (upper layer) separated from the ethanol layer (lower layer) was collected and used as a sample.

[0085] In Example 13, 80% ethanol (twice the weight of the sample in Comparative Example 3) was added, and the mixture was stirred and washed for 1 hour, and then allowed to stand for 30 minutes. The caryophyllene layer (upper layer) that separated from the ethanol layer (lower layer) was collected and used as a sample.

[0086] In Example 14, twice the weight of the sample in Example 13 was added to 80% ethanol, and the mixture was stirred and washed for 1 hour, and then allowed to stand for 30 minutes. The caryophyllene layer (upper layer) that separated from the ethanol layer (lower layer) was collected and used as a sample.

[0087] In Example 15, 60% by weight ethanol was added in an amount 10 times by weight to the sample of Comparative Example 3, and the mixture was stirred and washed for 1 hour, and then allowed to stand for 30 minutes. The caryophyllene layer (upper layer) that separated from the ethanol layer (lower layer) was collected and used as a sample.

[0088] In Example 16, 80% by weight ethanol was added in an amount 10 times by weight to the sample of Comparative Example 3, and the mixture was stirred and washed for 1 hour, and then allowed to stand for 30 minutes. The caryophyllene layer (upper layer) that separated from the ethanol layer (lower layer) was collected and used as a sample.

[0089] Example 11: Sample of Comparative Example 3 + 2 times the weight of 60% ethanol by weight + 1 hour of stirring and washing Example 12: Sample of Example 11 + 2 times the weight of 60% ethanol by weight + 1 hour of stirring and washing Example 13: Sample of Comparative Example 3 + 2 times the weight of 80% ethanol by weight + 1 hour of stirring and washing Example 14: Sample of Example 13 + 2 times the weight of 80% ethanol by weight + 1 hour of stirring and washing Example 15: Sample of Comparative Example 3 + 10 times the weight of 60% ethanol by weight + 1 hour of stirring and washing Example 16: Sample of Comparative Example 3 + 10 times the weight of 80% ethanol by weight + 1 hour of stirring and washing The results of content measurement, palatability evaluation, and safety evaluation of each sample are shown in Table 4 below.

[0090] The numerical values ​​in Table 4 are in weight percent.

[0091] {Analysis 4} In this study, the contents of methyleugenol and eugenol decreased as the amount of ethanol added, which is a remover of the specified target components, increased. In this case, palatability was satisfied first, and then safety was satisfied. When palatability was satisfied first, the eugenol content was 0.0455 wt %, when safety was satisfied first, the methyleugenol content was 0.0049 wt %, and when both safety and palatability were satisfied first, the total content of methyleugenol and eugenol was 0.0249 wt %. The β-caryophyllene content did not change even when the amount of ethanol added increased.

[0092] {Conclusion} i) According to the above study, a clove-derived β-caryophyllene composition that is safe and satisfies palatability requirements can be obtained by using a clove-derived β-caryophyllene raw material with a purity of 85.7% by weight or more. The clove-derived β-caryophyllene content in the obtained clove-derived β-caryophyllene composition was 85.7% by weight or more (Tables 1, 2, and 4).

[0093] ii) The eugenol content that satisfied palatability was 0.0455 wt % or less (Table 4).

[0094] iii) The content of methyl eugenol that satisfies safety standards was assumed to be 0.005% by weight or less.

[0095] iv) Two methods for producing a clove-derived β-caryophyllene composition that is safe and palatable were identified. The essential processing elements in these two methods were the removers for the target components, methyleugenol and eugenol, which were activated carbon and ethanol, respectively.

[0096] v) Of the two production methods, the method using activated carbon was able to reduce the methyleugenol content more (Tables 2 and 4).

[0097] vi) It is estimated that even if a clove-derived β-caryophyllene raw material with a purity of 80% by weight is used, a clove-derived β-caryophyllene composition that satisfies safety and palatability requirements can be obtained. The reasons for this are as follows.

[0098] Figure 1 is a graph showing the changes in the methyleugenol content, the eugenol content, and the total content of methyleugenol and eugenol versus the amount (wt%) of activated carbon added in Table 1. Figure 2 is a graph showing the changes in the methyleugenol content, the eugenol content, and the total content of methyleugenol and eugenol versus the amount (wt%) of activated carbon added in Table 2. In the graphs of Figure 1 and Figure 2, the solid line, dashed line, and dotted line represent the methyleugenol content, the eugenol content, and the total content of methyleugenol and eugenol, respectively.

[0099] 1 and 2 , the eugenol content and the total eugenol content change in a curve that gradually approaches a final value as the amount of activated carbon added increases, whereas the methyleugenol content decreases almost linearly with a gentle slope as the amount of activated carbon added increases. Furthermore, the purity of the clove-derived β-caryophyllene raw material, 80 wt%, differs by only about 7% from the purity of Feedstock 1, 85.7 wt%. Therefore, using the purities of Feedstock 1 and Feedstock 2 and the methyleugenol contents in Feedstock 1 and Feedstock 2, an approximate value of the methyleugenol content when 15 wt% activated carbon is added to a clove-derived β-caryophyllene raw material with a purity of 80 wt% can be extrapolated.

[0100] According to this extrapolation method, the approximate value of the methyleugenol content of a clove-derived β-caryophyllene raw material with a purity of 80% by weight is 0.0080−(0.0066−0.0080)×(85.7−80.0) / (97.3−85.7)≈0.00869 (wt %).

[0101] Therefore, when 15% by weight of activated carbon is added to a clove-derived β-caryophyllene raw material with a purity of 80% by weight, the approximate value of the methyleugenol content is 0.0044 × 0.00869 / 0.0080 ≒ 0.00478 (% by weight).

[0102] Therefore, it is estimated that even if a clove-derived β-caryophyllene raw material with a purity of 80% by weight is used, a clove-derived β-caryophyllene composition that satisfies safety and palatability requirements can be obtained.

[0103] Many modifications and alternative embodiments will be apparent to those skilled in the art in light of the above description, and therefore the above description should be construed as illustrative only.

[0104] The composition containing plant-derived β-caryophyllene and the method for producing the same according to the present disclosure are useful as a plant-derived β-caryophyllene composition and a method for producing the same that contain plant-derived β-caryophyllene and enable the production of various safe and highly palatable products.

Claims

1. A composition containing plant-derived β-caryophyllene, the composition having a plant-derived β-caryophyllene content of 80% by weight or more, a eugenol content of 0.0455% by weight or less, and a methyleugenol content of 0.005% by weight or less.

2. A composition comprising plant-derived β-caryophyllene according to claim 1, wherein the plant-derived β-caryophyllene is β-caryophyllene derived from cloves (Cloves).

3. A pharmaceutical, quasi-drug, food or drink, health food, cosmetic, fragrance, air freshener or daily necessities containing a composition containing β-caryophyllene derived from a plant according to claim 1 or 2.

4. An inhalation liquid for an inhaler or an inhalation assisting device, comprising a composition containing β-caryophyllene derived from a plant according to claim 1 or 2.

5. An aroma solution for an aroma diffuser, comprising a composition containing β-caryophyllene derived from a plant according to claim 1 or 2.

6. An electronic cigarette liquid containing a composition containing β-caryophyllene derived from the plant according to claim 1 or 2.

7. A method for producing a composition containing plant-derived β-caryophyllene, comprising: filtering a liquid raw material having a plant-derived β-caryophyllene content of 80% by weight or more through a filter, thereby obtaining a filtered liquid composition; adding activated carbon to the filtered liquid composition so that the activated carbon accounts for 3 to 15% by weight of the filtered liquid composition, thereby obtaining the activated carbon-added liquid composition; stirring the activated carbon-added liquid composition for a predetermined period of time, thereby obtaining a stirred liquid composition; and filtering the stirred liquid composition through a filter, thereby obtaining a composition containing plant-derived β-caryophyllene, wherein the plant-derived β-caryophyllene content is 80% by weight or more, the eugenol content is 0.0455% by weight or less, and the methyleugenol content is 0.005% by weight or less.

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