Method for decolorizing essential oils

Abstract

To provide a method for decolorizing an essential oil which causes little change in the flavor of the essential oil even after decolorization.SOLUTION: A first embodiment of the present invention is a method for decolorizing an essential oil, including an oxidation step of oxidizing the essential oil, wherein the oxidation step includes a ventilation step of passing air or oxygen through the essential oil under light-shielding conditions.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a method for decolorizing essential oils. The present invention also relates to decolorized oils, perfume compositions, food and drink products, oral care products, or cosmetics.

Background Art

[0002] Conventionally, from the viewpoint of improving product value and the like, decolorization has been performed in the process of purifying oils such as essential oils. Various methods are used for decolorizing oils. For example, Patent Document 1 discloses a technique for decolorization using activated carbon as an adsorbent.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, according to the studies by the present inventors, it has been found that when the technique described in Patent Document 1 is applied to essential oils, the flavor of the essential oil may change significantly after decolorization.

[0005] An object of the present invention is to provide a method for decolorizing essential oils, in which the change in the flavor of the essential oil is small even after decolorization.

Means for Solving the Problems

[0006] As a result of intensive studies to achieve the above object, the present inventors have found that the above problems can be solved by the following method, and have completed the present invention.

[0007] <1>A method for decolorizing essential oils having an oxidation step of oxidizing essential oils, The oxidation step comprises adding water and phenol oxidase to the essential oil. A method for decolorizing essential oil, wherein the amount of water added is 0.1 to 1000 parts by mass per 100 parts by mass of essential oil. <2> The phenol oxidase is at least one selected from the group consisting of laccase, peroxidase, and tyrosinase. <1> The method for decolorizing essential oils as described. <3> The phenol oxidase is laccase. <1> or <2> The method for decolorizing essential oils as described. <4> A method for decolorizing essential oils, comprising an oxidation step for oxidizing the essential oils, A method for decolorizing an essential oil, wherein the oxidation step comprises a ventilation step of passing air or oxygen through the essential oil under light shielding. <5> The aforementioned ventilation process is carried out under conditions of 100°C or lower. <4> The method for decolorizing essential oils as described. <6> The amount of air or oxygen to be passed through in the aeration process is 0.01 to 10 liters per minute per liter of essential oil. <4> or <5> The method for decolorizing essential oils as described. <7> The process includes a stirring step of stirring the essential oil, <4> ~ <6> The decolorization method for essential oils described in any one of the following. <8> <1> ~ <7> A decolorized oil obtained by the decolorization method of essential oil described in any one of the following. <9> <8> A fragrance composition containing the decolorizing oil described above. <10> <9> Food and beverages, oral care products, or cosmetics containing the fragrance composition described above. [Effects of the Invention]

[0008] The essential oil decolorized by the decolorization method of the present invention exhibits less change in flavor compared to the essential oil before decolorization. Furthermore, the decolorization method of the present invention can be performed easily. [Modes for carrying out the invention]

[0009] The present invention will be described in detail below, but these are merely examples of preferred embodiments, and the present invention is not limited to these.

[0010] The present invention provides a method for decolorizing essential oils, which includes an oxidation step of oxidizing the essential oil. In the first embodiment of the present invention, the oxidation step includes adding water and phenol oxidase to the essential oil, wherein the amount of water added is 0.1 to 1000 parts by mass per 100 parts by mass of the essential oil.

[0011] It is believed that adding water and phenol oxidase to essential oils oxidizes the pigment components, thereby decolorizing the essential oils. In this process, the flavor of the essential oils does not change significantly even after decolorization.

[0012] In this invention, "small change in essential oil flavor" means that there is no significant change in the quality of the aroma and the amount of aroma components in the essential oil, and that there is no significant sensory impact on the overall flavor.

[0013] Furthermore, if the amount of water added is 0.1 parts by mass or more per 100 parts by mass of essential oil, the phenol oxidase can come into sufficient contact with the essential oil. On the other hand, if the amount of water added exceeds 1000 parts by mass per 100 parts by mass of essential oil, the flavor of the essential oil after decolorization will change significantly.

[0014] The amount of water added is preferably 0.5 to 200 parts by mass, and more preferably 1 to 50 parts by mass, per 100 parts by mass of essential oil. A smaller amount of water added is preferable because it not only minimizes changes in flavor but also makes the subsequent water removal process easier.

[0015] From the viewpoint of obtaining a sufficient decolorizing effect, the amount of phenol oxidase added is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, and even more preferably 0.01 parts by mass or more, per 100 parts by mass of water. Furthermore, from the viewpoint of solubility in water, the amount of phenol oxidase added is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, and even more preferably 12 parts by mass or less, per 100 parts by mass of water.

[0016] The method of adding water and phenol oxidase to essential oil is not particularly limited, and water and phenol oxidase may be added simultaneously or separately. It is preferable to perform a stirring treatment on the mixture obtained by adding water and phenol oxidase to essential oil.

[0017] The stirring time may be, for example, 1 to 240 hours, preferably 24 to 120 hours. At that time, the temperature of the above mixture may be, for example, 15 to 55°C, preferably 30 to 45°C. In addition, the above mixture may be allowed to stand for, for example, 5 to 240 minutes, preferably 30 to 120 minutes, under the conditions of, for example, 15 to 55°C after stirring.

[0018] The essential oil and phenol oxidase can be reacted as described above. In the present invention, it is preferable not to use a mediator and a coenzyme. When a mediator and a coenzyme are used, the phenol oxidase activity may become too high, and there is a risk that the flavor change of the essential oil after decolorization will be large.

[0019] After the reaction, it is preferable to remove the aqueous layer from the above mixture and heat the oil layer to inactivate the phenol oxidase. The method of removing the aqueous layer is not particularly limited, and examples include separation using a separatory funnel, filtration such as natural filtration, vacuum filtration, pressure filtration, and centrifugal filtration, and methods using a dehydrating agent such as anhydrous magnesium sulfate, sodium sulfate, calcium carbonate, and molecular sieves. The heating temperature of the oil layer may be, for example, 80 to 100°C, preferably 85 to 90°C, and the heating time may be, for example, 15 to 60 minutes, preferably 20 to 40 minutes.

[0020] After inactivating the phenol oxidase, it is preferable to perform a dehydration treatment on the oil layer with a dehydrating agent and filter the remaining oil layer. The method of filtering the oil layer is not particularly limited, and examples include diatomaceous earth filtration, natural filtration, vacuum filtration, pressure filtration, and centrifugal filtration. As described above, the essential oil can be decolorized to obtain the decolorized oil of the present invention. The above operations performed after the reaction may be in any order.

[0021] The essential oil used in the present invention may be a natural essential oil or a synthetic essential oil, and can be obtained by a conventionally known method. Examples of the essential oil include citrus oils (such as grapefruit oil, orange oil, lemon oil, tangerine oil, lime oil, yuzu oil, etc.), mint oils (such as peppermint oil, spearmint oil, perilla oil, etc.), ginger oil, lavender oil, eucalyptus oil, rosemary oil, and the like.

[0022] The essential oil used in the present invention may be one obtained by distilling and concentrating a natural essential oil or a synthetic essential oil, for example, under reduced pressure.

[0023] The water used in the present invention is not particularly limited, and examples thereof include ion-exchanged water, distilled water, ultrapure water, tap water, and the like.

[0024] The phenol oxidase used in the present invention may be a commercially available one or a microorganism-derived one. When using a microorganism-derived phenol oxidase, a culture solution of the microorganism that produces the phenol oxidase may be added to the essential oil. Examples of the microorganism that produces the phenol oxidase include white rot fungi, specifically Lentinula edodes, Trametes versicolor, etc. Other microorganisms include Bacillus subtilis, Bacillus licheniformis, Pseudomonas extremorientalis, Pseudomonas aeruginosa, Pseudomonas putida, Streptomyces bikiniensis, Streptomyces cyaneus, Azospirillum lipoferum, etc.

[0025] Examples of the phenol oxidase include laccase, peroxidase, tyrosinase, etc. Among these, laccase is preferable from the viewpoint of the decolorization effect.

[0026] Furthermore, in the second embodiment of the present invention, the above-described oxidation step includes a ventilation step in which air or oxygen is passed through the essential oil under light shielding.

[0027] It is believed that exposing essential oils to air or oxygen under light-blocking conditions oxidizes the pigment components, thus decolorizing the essential oils. In this case, the flavor of the essential oils does not change significantly even after decolorization.

[0028] The aeration process is preferably carried out under conditions of 100°C or lower, more preferably under conditions of 0 to 100°C, and even more preferably under conditions of 20 to 80°C, from the viewpoint of obtaining a sufficient decolorization effect.

[0029] From the viewpoint of obtaining a sufficient decolorization effect, the amount of air or oxygen to be supplied in the aeration process is preferably 0.01 to 10 L per minute, more preferably 0.05 to 5 L per minute, and even more preferably 0.1 to 3 L per minute, per liter of essential oil.

[0030] Furthermore, it is preferable to stir the essential oil before, after, or simultaneously with the aeration process. The stirring time can be, for example, 1 to 1500 hours, preferably 1 to 750 hours.

[0031] The fragrance composition of the present invention contains the decolorizing oil of the present invention. The content of the decolorizing oil in the fragrance composition of the present invention is not strictly limited and can be varied depending on the use of the fragrance composition, but it is preferably 0.001 to 100% by mass, and more preferably 0.01 to 100% by mass.

[0032] The fragrance composition of the present invention may contain known fragrance components in addition to decolorizing oil. Known fragrance components include, for example, hydrocarbons such as α-pinene, β-pinene, limonene, p-cymene, and thujone; aliphatic alcohols such as octanol and p-tert-butylcyclohexanol; terpene alcohols such as menthol, citronellol, and geraniol; aromatic alcohols such as benzyl alcohol and phenylethyl alcohol; aliphatic aldehydes; terpene aldehydes; aromatic aldehydes; acetals; chain ketones; damascone; cyclic ketones such as β-ionone and methylionone. Examples include terpene ketones such as carvone, menthone, isomentone, and camphor; aromatic ketones such as acetophenone and raspberry ketone; ethers such as dibenzyl ether; oxides such as linalool oxide and rose oxide; musks such as cyclopentadecanolide and cyclohexadecanolide; lactones such as γ-nonalactone, γ-undecalactone, and coumarin; aliphatic esters such as acetate and propionic acid; and aromatic esters such as benzoic acid and phenyl acetate.

[0033] The fragrance composition of the present invention may further contain ethanol, isopropyl alcohol, ethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, polyethylene glycol, diethyl phthalate, isopropyl myristate, triethyl citrate, benzyl benzoate, glycerin, triacetin, benzyl alcohol, paraffin, isoparaffin, rosin ester derivatives such as Harcolin, 3-methoxy-3-methyl-1-butanol, ethyl carbitol (diethylene glycol monoethyl ether), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol propyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol butyl ether, and other glycol ethers, terpene resins such as pinene polymers, silicones such as cyclic silicones, and solvents and fixatives such as water.

[0034] Furthermore, the fragrance composition of the present invention may optionally further contain known components such as higher alcohols, surfactants, antioxidants, ultraviolet absorbers, chelating agents, solubilizers, stabilizers, cooling agents, preservatives, antibacterial agents, disinfectants, fungicides, insecticides, and pigments.

[0035] The fragrance composition of the present invention can be obtained, for example, by mixing and stirring the components, and heating may be performed as desired. The content of each component can be adjusted as appropriate.

[0036] The food and beverage products, oral care products, or cosmetics of the present invention contain the fragrance composition of the present invention. The content of the fragrance composition in the food and beverage products, oral care products, or cosmetics of the present invention is not strictly limited and can be varied depending on the use of the food and beverage products, oral care products, or cosmetics, but it is preferably 0.0001 to 10% by mass, and more preferably 0.001 to 1% by mass.

[0037] The form of the food, beverage, oral care product, or cosmetic product of the present invention is not limited and may be a liquid, solid, semi-solid, or fluid.

[0038] Examples of food and beverages include liquid products such as fruit drinks, vegetable drinks, carbonated drinks, sports drinks, coffee drinks, tea, black tea, yogurt drinks, lactic acid bacteria drinks, nutritional drinks, soups, noodle soups, etc.; solid products such as candy, gum, gummies, jelly, chocolate, ice cream, ham, sausages, snacks, etc.; and liquid products such as curry, stew, Hayashi rice, sauces, dressings, fresh cream, etc.

[0039] Examples of oral care products include toothpaste, toothpaste paste, liquid toothpaste, mouthwash, gum massage cream, topical ointments, lozenges, and chewing gum.

[0040] Cosmetics include, for example, fragrance products (perfumes, eau de parfums, eau de toilettes, eau de colognes, etc.), basic cosmetics (cleansing creams, vanishing creams, cleansing creams, cold creams, massage creams, lotions, toners, serums, face masks, makeup removers, etc.), and finishing cosmetics (foundations, loose powders, solid powders, talcum powder, lipsticks, lip balms, blushes, eyeliners, mascaras, eyeshadows, eyebrow pencils, eye masks, nail polish, and nail polish removers). Examples include hair care products (pomade, brillanthin, setting lotion, hair stick, hair solid, hair oil, hair treatment, hair cream, hair tonic, hair liquid, hair spray, bandolin, hair tonic, hair dye, etc.), sun tanning products (suntan products, sunscreen products, etc.), and medicated cosmetics (antiperspirants, aftershave lotion, aftershave gel, permanent wave agents, medicated soap, medicated shampoo, medicated skin cosmetics, etc.). [Examples]

[0041] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

[0042] [Test Example 1] <Example 1-1> 17g of Gardner color number 18 grapefruit oil 5x concentrate was mixed with 3g of deionized water and 0.34g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 48 hours, and then allowed to stand at 25°C for 30 minutes.

[0043] In this specification, "5x concentrated grapefruit oil" refers to grapefruit oil from which unwanted terpenes have been removed, resulting in a five-fold increase in the content of useful oxygen-containing compounds. 5x concentrated grapefruit oil can be obtained by heating grapefruit oil and distilling it under reduced pressure.

[0044] After standing, the aqueous layer was removed using a separatory funnel, and the oil layer was heated at 85°C for 30 minutes to inactivate the enzymes. After enzyme inactivation, the oil layer was filtered through filter paper to obtain 14.5 g of 5x concentrated grapefruit oil.

[0045] <Comparative Example 1-1> A column was packed with 160g of "Activated Carbon GAC1240" (manufactured by CABOT NORIT), and 1000g of grapefruit oil with a Gardner color number of 15 was passed through it. The column was circulated at 25°C for 6 hours. After circulation, the grapefruit oil was filtered through filter paper, and 190g of a 5x concentrated grapefruit oil was obtained by distillation.

[0046] (Oil analysis) The 5x concentrated grapefruit oil obtained in Example 1-1 and Comparative Example 1-1, as well as the untreated 5x concentrated grapefruit oil, were measured for Gardner color number, specific gravity, refractive index, and flavor component concentrations (concentrations of nootkatone and auraptene). The results are shown in Table 1.

[0047] The Gardner color number was measured by comparing grapefruit oil to Gardner samples. If the oil's color fell between two Gardner samples, the closest Gardner color number was determined, and a "+" was added if the oil was darker than that number, and a "-" if it was lighter. Specific gravity was measured using a hydrometer (Anton Paar, "DMA 4500M"). Refractive index was measured using a refractometer (ATAGO, "RX-5000i"). Flavor component concentrations were calculated using GC-FID after peak assignment was performed by GC-MS analysis.

[0048] (Sensory evaluation) The 5x concentrated grapefruit oil obtained in Example 1-1 and Comparative Example 1-1 were subjected to sensory evaluation by five expert panelists as follows. First, an ethanol solution containing 5% by mass of the 5x concentrated grapefruit oil was prepared. This solution was then mixed with water at a concentration of 0.1% by mass and flavored. The untreated product was used as a control and evaluated according to the following criteria. Table 1 shows the average score, comments, and overall evaluation from the five panelists. An average score of 4 or higher was considered a passing grade in the sensory evaluation.

[0049] 5 points: The scent was comparable to the control. 4 points: The scent was slightly different compared to the control version. 3 points: The scent was slightly different compared to the control version. Points 2: The scent was significantly different compared to the control version. 1 point: The scent was completely different compared to the control.

[0050] [Table 1]

[0051] The results in Table 1 show that in Example 1-1, the grapefruit oil was decolorized while maintaining almost no change in specific gravity, refractive index, or flavor component concentration compared to the untreated product. Furthermore, in sensory evaluation, Example 1-1 was equivalent to the untreated product.

[0052] [Test Example 2] <Example 2-1> 17g of Gardner color number 15 grapefruit oil 5x concentrate was mixed with 3g of deionized water and 0.085g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 30°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0053] After standing, the same procedure as in Example 1-1 was performed to obtain 14.1 g of 5x concentrated grapefruit oil.

[0054] <Example 2-2> Except for using 0.085g of "Peroxidase" (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) instead of 0.085g of "Laccase Y-120", the same procedure as in Example 2-1 was followed to obtain 13.9g of a 5x concentrated grapefruit oil.

[0055] The grapefruit oils obtained in Examples 2-1 to 2-2, as well as untreated grapefruit oil, were measured for Gardner color number, specific gravity, refractive index, and flavor component concentrations (concentrations of nootkatone and auraptene) in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Table 2.

[0056] [Table 2]

[0057] The results in Table 2 show that in Examples 2-1 to 2-2, the grapefruit oil was decolorized while maintaining almost no change in specific gravity, refractive index, or flavor component concentration compared to the untreated product. Furthermore, in sensory evaluation, Examples 2-1 to 2-2 were equivalent to the untreated product.

[0058] [Test Example 3] <Example 3-1> 17g of Gardner color 9 orange oil was mixed with 3g of deionized water and 0.34g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0059] After standing, the same procedure as in Example 1-1 was performed to obtain 13.4 g of orange oil.

[0060] The orange oil obtained in Example 3-1, as well as the untreated orange oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Table 3.

[0061] [Table 3]

[0062] Table 3 shows that in Example 3-1, the orange oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Example 3-1 was equivalent to the untreated product.

[0063] [Test Example 4] <Example 4-1> 17g of Gardner color 15 grapefruit oil was mixed with 3g of deionized water and 0.17g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0064] After standing, the same procedure as in Example 1-1 was performed to obtain 13.6 g of grapefruit oil.

[0065] The grapefruit oil obtained in Example 4-1, as well as untreated grapefruit oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Table 4.

[0066] [Table 4]

[0067] The results in Table 4 show that in Example 4-1, the grapefruit oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Example 4-1 was equivalent to the untreated product.

[0068] [Test Example 5] <Example 5-1> 291.7g of Gardner color 14+ grapefruit oil was mixed with 58.3g of deionized water and 2.935g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0069] After standing, the same procedure as in Example 1-1 was performed to obtain 273.7 g of grapefruit oil.

[0070] <Example 5-2> Except for using 175g of grapefruit oil and adding 175g of deionized water, the same procedure as in Example 5-1 was followed to obtain 156.3g of grapefruit oil.

[0071] <Example 5-3> Except for using 50g of grapefruit oil and adding 300g of deionized water, the same procedure as in Example 5-1 was followed to obtain 42.5g of grapefruit oil.

[0072] <Example 5-4> Except for using 35g of grapefruit oil and adding 315g of deionized water, the same procedure as in Example 5-1 was followed to obtain 28.3g of grapefruit oil.

[0073] <Comparative Example 5-1> Except for using 14g of grapefruit oil and adding 336g of deionized water, the same procedure as in Example 5-1 was followed to obtain 11.5g of grapefruit oil.

[0074] The grapefruit oils obtained in Examples 5-1 to 5-4 and Comparative Example 5-1, as well as untreated grapefruit oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Table 5.

[0075] [Table 5]

[0076] The results in Table 5 show that in Examples 5-1 to 5-4, the grapefruit oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Examples 5-1 to 5-4 were equivalent to the untreated product.

[0077] [Test Example 6] <Example 6-1> 1089g of Gardner color 15 grapefruit oil was mixed with 11g of deionized water and 0.0011g of Lacase Y-120 (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0078] After standing, the same procedure as in Example 1-1 was performed to obtain 1001.9g of grapefruit oil.

[0079] <Example 6-2> Except for adding 0.11g of "Lacase Y-120", the same procedure as in Example 6-1 was followed to obtain 999.3g of grapefruit oil.

[0080] <Example 6-3> Except for adding 1.1g of "Laccase Y-120", the same procedure as in Example 6-1 was followed to obtain 997.1g of grapefruit oil.

[0081] <Example 6-4> 1000g of Gardner color 15 grapefruit oil was mixed with 100g of deionized water and 0.01g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0082] After standing, the same procedure as in Example 1-1 was performed to obtain 951.2 g of grapefruit oil.

[0083] <Example 6-5> Except for adding 1 g of "Lacase Y-120", the same procedure as in Example 6-4 was followed to obtain 949 g of grapefruit oil.

[0084] <Example 6-6> Except for adding 10g of "Lacase Y-120", the same procedure as in Example 6-4 was followed to obtain 948.5g of grapefruit oil.

[0085] <Examples 6-7> 550g of Gardner color 15 grapefruit oil was mixed with 550g of deionized water and 0.055g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.). The mixture was stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0086] After standing, the same procedure as in Example 1-1 was performed to obtain 511.5 g of grapefruit oil.

[0087] <Examples 6 and 8> Except for adding 5.5g of "Lacase Y-120", the same procedure as in Examples 6-7 was followed to obtain 510g of grapefruit oil.

[0088] <Examples 6 and 9> Except for adding 55g of "Lacase Y-120", the same procedure as in Example 6-7 was followed to obtain 508.2g of grapefruit oil.

[0089] <Examples 6-10> 100g of Gardner color 15 grapefruit oil was mixed with 1000g of deionized water and 0.1g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0090] After standing, the same procedure as in Example 1-1 was performed to obtain 88.4 g of grapefruit oil.

[0091] <Example 6-11> Except for adding 10g of "Lacase Y-120", the same procedure as in Example 6-10 was followed to obtain 87.5g of grapefruit oil.

[0092] <Example 6-12> Except for adding 100g of "Lacase Y-120", the same procedure as in Example 6-10 was followed to obtain 87g of grapefruit oil.

[0093] <Comparative Example 6-1> 50g of Gardner color 15 grapefruit oil was mixed with 1050g of deionized water and 0.105g of "Laccase Y-120" (manufactured by Amano Enzyme Co., Ltd.), stirred at 45°C for 24 hours, and then allowed to stand at 25°C for 30 minutes.

[0094] After standing, the same procedure as in Example 1-1 was performed to obtain 42.6 g of grapefruit oil.

[0095] <Comparative Example 6-2> Except for adding 10.5g of "Lacase Y-120", the same procedure as in Comparative Example 6-1 was performed to obtain 41.5g of grapefruit oil.

[0096] <Comparative Example 6-3> Except for adding 105g of "Laccase Y-120," the same procedure as in Comparative Example 6-1 was followed to obtain 40.1g of grapefruit oil.

[0097] The grapefruit oils obtained in Examples 6-1 to 6-12 and Comparative Examples 6-1 to 6-3, as well as untreated grapefruit oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Tables 6 and 7.

[0098] [Table 6]

[0099] [Table 7]

[0100] The results in Tables 6 and 7 show that in Examples 6-1 to 6-12, the grapefruit oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Examples 6-1 to 6-12 were equivalent to the untreated product.

[0101] [Test Example 7] <Example 7-1> 1000g of Gardner color number 14- grapefruit oil was stirred for 72 hours under light-shielding conditions, with an air permeability of 0.01 vvm, at 37°C to obtain grapefruit oil.

[0102] In this specification, the airflow rate vvm refers to the number of times the volume of oil that air is passed through per minute. In Test Example 7, air was used for aeration, and the aeration and stirring treatments were performed simultaneously.

[0103] <Example 7-2> 1000g of Gardner color number 14- grapefruit oil was stirred for 72 hours under light-shielding conditions, with an air permeability of 0.1 vvm, at 37°C, to obtain grapefruit oil.

[0104] <Example 7-3> 1000g of grapefruit oil with Gardner color number 14 was stirred for 72 hours under light-shielding conditions, with an air permeability of 1 vvm, at 37°C, to obtain grapefruit oil.

[0105] <Example 7-4> 1000g of grapefruit oil with Gardner color number 14 was stirred for 72 hours under light-shielding conditions, with an air permeability of 2vvm and at 37°C to obtain grapefruit oil.

[0106] <Example 7-5> 1000g of Gardner color number 14- grapefruit oil was stirred for 72 hours under light-shielding conditions with an air permeability of 5vvm and at 37°C to obtain grapefruit oil.

[0107] <Example 7-6> 1000g of grapefruit oil with Gardner color number 14 was stirred for 72 hours under light shielding, with an air permeability of 10 vvm and at 37°C to obtain grapefruit oil.

[0108] <Example 7-7> 1000g of Gardner color number 14- grapefruit oil was stirred for 144 hours under light shielding, with an air permeability of 0.1 vvm, at 37°C to obtain grapefruit oil.

[0109] <Examples 7 and 8> 1000g of Gardner color number 14- grapefruit oil was stirred for 24 hours under light shielding, with an air permeability of 0.1 vvm, at 50°C to obtain grapefruit oil.

[0110] <Examples 7 and 9> 1000g of Gardner color number 14- grapefruit oil was stirred for 240 hours under light shielding, with an air permeability of 0.1 vvm, at 25°C to obtain grapefruit oil.

[0111] <Example 7-10> 1000g of grapefruit oil with Gardner color number 14 was stirred for 720 hours under light shielding, with an air permeability of 0.1 vvm, and at 10°C to obtain grapefruit oil.

[0112] <Example 7-11> 1000g of Gardner color number 14- grapefruit oil was stirred for 10 hours under light shielding, with an air permeability of 0.1 vvm, at 75°C to obtain grapefruit oil.

[0113] <Example 7-12> 1000g of grapefruit oil with Gardner color number 14 was stirred under light-shielding conditions, with an air permeability of 0.1 vvm, at 100°C for 5 hours to obtain grapefruit oil.

[0114] <Comparative Example 7-1> 1000g of grapefruit oil with Gardner color number 14 was subjected to a light-shielding treatment, where the container was sealed after nitrogen purging and stirred at 37°C for 72 hours to obtain grapefruit oil.

[0115] <Comparative Example 7-2> 1000g of grapefruit oil with Gardner color number 14 was stirred for 72 hours under light-shielding conditions, with an air permeability of 15 vvm and a temperature of 37°C to obtain grapefruit oil.

[0116] <Comparative Example 7-3> 1000g of grapefruit oil with a Gardner color number of 14 was stirred under light-shielding conditions, with an air permeability of 0.1 vvm, at 120°C for 2 hours to obtain grapefruit oil.

[0117] <Comparative Example 7-4> 1000g of Gardner color number 14- grapefruit oil was stirred for 72 hours at 37°C without shading (1000 lux) and with an air permeability of 0.1 vvm to obtain grapefruit oil.

[0118] <Comparative Example 7-5> 1000g of Gardner color number 14- grapefruit oil was left to stand for 72 hours under light shielding, with an air permeability of 0.1 vvm, and at 37°C to obtain grapefruit oil.

[0119] The grapefruit oils obtained in Examples 7-1 to 7-12 and Comparative Examples 7-1 to 7-5, as well as untreated grapefruit oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Tables 8 and 9.

[0120] [Table 8]

[0121] [Table 9]

[0122] The results in Tables 8 and 9 show that in Examples 7-1 to 7-12, the grapefruit oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Examples 7-1 to 7-12 were equivalent to the untreated product.

[0123] [Test Example 8] <Example 8-1> 1000g of Gardner color number 16- grapefruit oil 5x concentrate was stirred for 64 hours at 50°C under light shielding with an air permeability of 0.1 vvm to obtain grapefruit oil 5x concentrate.

[0124] Air was used for ventilation, and the ventilation and stirring processes were carried out simultaneously.

[0125] The 5x concentrated grapefruit oil obtained in Example 8-1, as well as the untreated 5x concentrated grapefruit oil, were measured for Gardner color number in the same manner as in Test Example 1. Sensory evaluation was also performed in the same manner as in Test Example 1. The results are shown in Table 10.

[0126] [Table 10]

[0127] The results in Table 10 show that in Example 8-1, the grapefruit oil was decolorized compared to the untreated product. Furthermore, in sensory evaluation, Example 8-1 was equivalent to the untreated product.

[0128] Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention. This application is based on Japanese Patent Application No. 2020-052999, filed on 24 March 2020, the contents of which are incorporated herein by reference.

Claims

1. A method for decolorizing essential oils, comprising an oxidation step for oxidizing the essential oils, The aforementioned essential oil is grapefruit oil. The oxidation step includes an aeration step in which, while stirring the essential oil, air or oxygen is passed through the essential oil at a rate of 0.01 to 10 liters per minute per liter of essential oil under light shielding conditions. The aeration step is carried out under conditions of 100°C or lower in a method for decolorizing essential oils.

2. A decolorized oil obtained by the decolorization method for essential oils described in claim 1.

3. A fragrance composition containing the decolorizing oil described in claim 2.

4. A food or beverage, oral care product, or cosmetic product containing the fragrance composition described in claim 3.

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