WO2016121186A1 - Huile essentielle d'agrumes soluble de manière transparente dans un solvant hydrophile et procédé de production d'huile essentielle d'agrumes - Google Patents

Huile essentielle d'agrumes soluble de manière transparente dans un solvant hydrophile et procédé de production d'huile essentielle d'agrumes Download PDF

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WO2016121186A1
WO2016121186A1 PCT/JP2015/080879 JP2015080879W WO2016121186A1 WO 2016121186 A1 WO2016121186 A1 WO 2016121186A1 JP 2015080879 W JP2015080879 W JP 2015080879W WO 2016121186 A1 WO2016121186 A1 WO 2016121186A1
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Prior art keywords
essential oil
citrus essential
distillation
citrus
mass
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PCT/JP2015/080879
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English (en)
Japanese (ja)
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康隆 大久保
尚子 田中
哲朗 西沢
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長谷川香料株式会社
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Priority to JP2016571679A priority Critical patent/JP6371863B2/ja
Publication of WO2016121186A1 publication Critical patent/WO2016121186A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials

Definitions

  • the present invention relates to a method for producing a purified citrus oil that is transparently dissolved in a hydrophilic solvent, a refined citrus oil produced by the production method, and a fragrance composition containing the refined citrus oil.
  • Citrus has a fresh and fruity aroma and is popular with many people, so it is widely used in food and drink.
  • citrus essential oil such as peel oil pronounced of citrus fragrance can be collected from the peel.
  • Citrus essential oil is an important material for citrus-like flavoring and flavoring of foods and drinks. When used for flavoring and flavoring, it is diluted with a solvent that is easily dissolved in the foods and drinks used. Has been. When used for foods and drinks with a high water content, hydrophilic solvents, specifically hydrous alcohol, propylene glycol, glycerin, etc., can be mentioned, but it is generally diluted with these solvents and used. Is. However, it is known that citrus essential oil contains many components that are difficult to dissolve in these hydrophilic solvents and is difficult to dissolve transparently. Thus, in order to improve solubility, citrus essential oil is widely processed to remove components that are difficult to dissolve in hydrophilic solvents. Since many of the components that are difficult to dissolve in the hydrophilic solvent are terpene hydrocarbons, these operations are generally referred to as terpeneless.
  • washing As a terpeneless method, industrially widely performed are a step called washing, a step of extracting citrus essential oil with hydrous alcohol, and a step called folding, which is a step of removing monoterpene hydrocarbons by vacuum distillation.
  • washing has the disadvantage that the solvent is limited to hydrous alcohol, and most of the fragrance component is distributed to the terpene hydrocarbon layer rather than the hydrous alcohol layer, so that extraction efficiency is poor and the fragrance intensity is limited.
  • folding when the removal rate of the terpene hydrocarbon is increased, the heating temperature is increased, and the fragrance is deteriorated due to thermal damage.
  • Non-Patent Document 1 Non-Patent Document 1
  • the terpeneless oil prepared by such a method is a transparent suspension in a hydrophilic solvent. Does not dissolve. Therefore, it must be combined with other terpene-less methods.
  • terpene hydrocarbon-containing natural essential oil especially citrus essential oil
  • the hydrous alcohol layer is hardly miscible or immiscible with the hydrous alcohol layer.
  • Patent Document 1 A method for obtaining a deterpened essential oil by further extracting with a low-boiling point hydrocarbon solvent, collecting the low-boiling point hydrocarbon solvent layer, and removing the solvent from the obtained solvent layer
  • Patent Document 2 Method of obtaining terpeneless essential oil by solvent extraction of cyclodextrin inclusion compound of natural essential oil
  • Patent Document 3 Method of treating citrus oil with a mixture of propylene glycol and alkanol having 1 to 4 hydrocarbons
  • Patent Document 4 a method of thin-film distillation of a distillation residue after removing a part of low boiling point aroma components from lemon peel oil by distillation is disclosed (Patent Document 4).
  • this method has the disadvantage that the fresh aroma of lemon is impaired because the oxygen-containing volatile components having a low boiling point are removed.
  • Patent Document 5 a manufacturing method in which thin film distillation or a similar technique such as short-step distillation or molecular distillation is applied to citrus essential oil is disclosed as a method for removing contaminants such as agricultural chemicals.
  • Patent Document 5 it has not been known so far that combining such a distillation method with precision distillation provides a means for improving the solubility of citrus essential oil in a hydrophilic solvent.
  • An object of the present invention is to provide a purification method for transparently dissolving citrus essential oil in a hydrophilic solvent by a method that can be easily carried out on an industrial scale.
  • the present inventors have conducted a thin film distillation of a non-volatile component that is difficult to dissolve in a hydrophilic solvent in citrus essential oil at a constant pressure, thereby reducing the aroma component.
  • the distillate obtained by thin-film distillation is made terpene-less by precision distillation, the loss during heating can be surprisingly different from conventional knowledge. It has been found that even if the temperature is low, it is possible to obtain a purified product of citrus essential oil having a monoterpene hydrocarbon content of 5% by mass or less.
  • the citrus essential oil refined product obtained by the production method of the present invention has been found to exhibit good solubility in hydrophilic solvents, specifically ethanol aqueous solution, isopropanol aqueous solution, propylene glycol, and completed the present invention. It came to do.
  • the present invention can provide the following purified citrus essential oil and a method for producing the purified citrus essential oil.
  • a fragrance composition comprising the purified citrus essential oil according to any one of [1] to [3] and one or more selected from the group consisting of an ethanol aqueous solution, an isopropanol aqueous solution, and propylene glycol.
  • a method for producing a purified product of citrus essential oil comprising the following steps (1) and (2): (1) A step of obtaining a distillate obtained by thin-film distillation of citrus essential oil or an essential oil having a reduced content of monoterpene hydrocarbon by distillation under reduced pressure at a pressure of 100 to 1000 Pa and a temperature of 10 to 100 ° C., (2) A step of obtaining a distillation residue by subjecting the distillate to at least one precision distillation at a pressure of 200 to 2000 Pa, a heating temperature of 20 to 125 ° C., and a distillation temperature of 20 to 90 ° C.
  • the method for producing a refined citrus essential oil according to [6] which does not contain a non-volatile component and has a monoterpene hydrocarbon content of 5% or less.
  • the refined citrus essential oil produced according to the present invention does not contain a non-volatile component and has a monoterpene hydrocarbon content of 5% by mass or less, and therefore has good solubility in an ethanol aqueous solution, an isopropanol aqueous solution, and propylene glycol. Can be dissolved transparently.
  • the citrus essential oil used in the present invention is mainly used by extracting the essential oil from the citrus peel by squeezing the peel with a roller called a squeezing method or a centrifugal method at a low temperature.
  • the essential oil collected by the pressing method is also called cold press oil.
  • the kind of citrus essential oil used by this invention will not be specifically limited if it is citrus, For example, lemon essential oil, lime essential oil, mandarin essential oil, grapefruit essential oil, orange essential oil etc. can be mentioned. Further, commercially available citrus essential oils may be used.
  • the citrus essential oil used in the present invention may be terpeneless.
  • Examples of the terpeneless method include the above-described methods such as washing and folding, and methods using a combination thereof.
  • thin film distillation is performed using the citrus essential oil to remove non-volatile components to obtain a distillate.
  • the conditions for the thin film distillation are monoterpene hydrocarbon compounds in which the distillation apparatus pressure is set to 100 to 1000 Pa, preferably 200 to 900 Pa, and the distillation apparatus temperature is 10 to 100 ° C., preferably at the distillation apparatus pressure. It is desirable to set the boiling point of limonene to 90 ° C. Note that the boiling point of limonene at 100 Pa is 11 ° C., and that at 1000 Pa is 47 ° C.
  • thin film distillation refers to continuously supplying a product to be distilled on a surface heated to a certain temperature to form a uniform thin film, and heating the product to be distilled only on the surface.
  • the distillation method separates a volatile component and a non-volatile component by evaporating the volatile component.
  • the thin film distillation apparatus used in the present invention is not particularly limited as long as the uniform thin film is formed, but a rotating thin film distillation apparatus, a falling film distillation apparatus, a centrifugal thin film distillation apparatus, a molecular distillation apparatus, etc. Can be mentioned.
  • Thin film distillation can remove non-volatile components with a single operation, but by repeatedly performing thin film distillation on the distillation residue, the recovery rate of volatile components can be increased.
  • the distillate obtained by thin film distillation is then subjected to precision distillation to distill off the terpene hydrocarbons contained in the citrus essential oil and to make terpenes less.
  • the precision distillation conditions are that the distillation apparatus pressure is set to 200 to 2000 Pa, preferably 400 to 1800 Pa, and the heating temperature of the distillation apparatus is set to 20 to 125 ° C., preferably the boiling point of limonene at the distillation apparatus pressure to 110 ° C.
  • Distillation temperature is 20 to 90 ° C., preferably 20 to boiling off limonene at the pressure of the distillation apparatus + 20 ° C. to distill off terpene hydrocarbons, particularly monoterpene hydrocarbons efficiently.
  • the boiling point of limonene at 200 Pa is 20 ° C., and at 2000 Pa, it is 62 ° C.
  • the precision distillation pressure and temperature are set so that monoterpene hydrocarbons can be distilled off from a distillate obtained by thin-film distillation of citrus essential oil, etc., and oxygen content that is an important aroma component of citrus essential oil
  • the condition that the compound remains and the oxygen-containing compound is not changed by heating is preferable. When heating temperature is set more than the said temperature, an oxygen-containing compound will change and the fresh fragrance derived from citrus essential oil will be lost.
  • terpene hydrocarbons can be distilled off by one operation, but terpene hydrocarbons can be surely distilled off by performing precision distillation twice or more.
  • the purified citrus essential oil of the present invention thus obtained contains no non-volatile components, and monoterpene hydrocarbons are 5% or less, preferably 4% or less, more preferably 3.5% or less.
  • the loss of oxygen-containing volatile components, which are characteristic components of citrus essential oil is minimized, and a fresh aroma is maintained.
  • the citrus essential oil refined product of the present invention is an orange essential oil refined product obtained by the method of the present invention
  • the proportion of the oxygen-containing volatile component that is a component unique to the citrus essential oil in the purified citrus essential oil of the present invention is 50% or more. It is preferably 60% or more, more preferably 70% or more, and particularly preferably 80% or more.
  • the proportion of the oxygen-containing volatile component which is a component unique to the citrus essential oil in the purified citrus essential oil of the present invention, is 50% or more. Preferably, it is 60% or more, more preferably 65% or more.
  • the refined citrus essential oil obtained in the present invention is easily dissolved in an aqueous ethanol solution, an isopropanol aqueous solution and / or propylene glycol.
  • a general orange essential oil obtained by squeezing orange peel can be dissolved completely in an aqueous solution of 80 to 100% by mass of ethanol, but completely transparent, but 60% by mass of ethanol.
  • 1% by mass of the orange essential oil was dissolved in a 1% aqueous solution, it became cloudy.
  • the purified orange essential oil obtained by the method of the present invention was dissolved in an aqueous solution of 60 to 100% by mass of ethanol in an amount of 1% by mass, it could be dissolved substantially completely transparently.
  • the absorbance at 680 nm when dissolved in 1% by mass in propylene glycol is preferably 0.1 or less, and preferably 0.05 or less. More preferred is 0.01 or less.
  • the purified citrus essential oil of the present invention preferably has an absorbance at 680 nm of 0.5% or less (using ion-exchanged water as a blank) when 1% by mass is dissolved in a 50% by mass aqueous solution of ethanol.
  • the purified citrus essential oil of the present invention is a purified orange essential oil obtained by the method of the present invention
  • the purified citrus essential oil of the present invention is 680 nm when dissolved in an aqueous solution of 50% by mass of ethanol at 1% by mass. Is preferably 0.5 or less (with ion-exchanged water as a blank), more preferably 0.3 or less, particularly preferably 0.15 or less, and 0.05 or less. Is more particularly preferable, and it is even more particularly preferable that it is 0.01 or less.
  • the refined citrus essential oil of the present invention is a refined lemon essential oil obtained by the method of the present invention
  • the refined citrus essential oil of the present invention has a 680 nm of 1% by mass dissolved in a 50% by mass aqueous solution of ethanol.
  • the absorbance is preferably 0.5 or less (using ion-exchanged water as a blank), more preferably 0.4 or less, particularly preferably 0.35 or less, and 0.05 or less. More particularly preferred is 0.01 or less, even more particularly preferred.
  • the refined citrus essential oil of the present invention is a refined refined grapefruit oil obtained by the method of the present invention
  • the refined citrus essential oil of the present invention is 680 nm when dissolved in an ethanol concentration of 50% by mass in an aqueous solution of 1% by mass. Is preferably 0.5 or less (using ion-exchanged water as a blank), more preferably 0.45 or less, and particularly preferably 0.4 or less.
  • the refined citrus essential oil of the present invention is a refined lime essential oil obtained by the method of the present invention
  • the refined citrus essential oil of the present invention is 680 nm when dissolved in an aqueous solution of 50% by mass of ethanol at 1% by mass. Is preferably 0.5 or less (using ion-exchanged water as a blank), more preferably 0.4 or less, and particularly preferably 0.35 or less.
  • the citrus essential oil refined product obtained in the present invention is less susceptible to thermal degradation and photodegradation of specific flavor components such as citral essential citrus components, compared to conventional purification methods, and Since it is difficult to produce an off-flavor that contributes to the fragrance, the fragrance derived from the citrus essential oil is hardly damaged over time.
  • the purified citrus essential oil obtained in the present invention can be added to foods and beverages and cosmetics as it is, but is easily dissolved in an ethanol aqueous solution, an isopropanol aqueous solution and / or propylene glycol.
  • a fragrance composition is obtained by blending a small amount of the citrus essential oil refined product of the present invention into a citrus fragrance composition such as orange-like, lemon-like, lime-like, grapefruit-like, or yuzu-like, and the resulting fragrance composition is used in foods or cosmetics.
  • fragrances such as natural citrus original peel, freshness, and freshness.
  • the amount of the refined citrus essential oil obtained in the present invention varies depending on the purpose or the type of the citrus fragrance composition, but for example, 1 ppm to 50%, preferably 10 ppm relative to the total weight of the citrus fragrance composition. A range of ⁇ 10% can be exemplified. Within these ranges, the citrus fragrance composition has an excellent effect of imparting a citrus original peel feeling, a fresh feeling, a freshness, and the like.
  • the present invention relates to a food or drink or cosmetic comprising an effective amount of a citrus fragrance composition containing a citrus flavor enhancer containing the citrus essential oil refined product obtained in the present invention as an active ingredient.
  • the original fragrance can be imparted.
  • Examples of foods and drinks include carbonated beverages such as cola beverages, carbonated beverages containing fruit juice, carbonated beverages containing milk; fruit juice beverages, vegetable beverages, sports drinks, honey beverages, soy milk, vitamin supplemented beverages, mineral supplemented beverages, nutritional drinks , Nourishment drinks, lactic acid bacteria drinks, milk drinks and other food drinks; green tea, black tea, oolong tea, herbal tea, coffee drinks and other favorite drinks; Chu-hi, cocktail drinks, sparkling liquor, fruit liquor, condiment drinks Desserts such as ice cream, lacto ice, ice confectionery, yogurt, pudding, jelly, daily desserts and mixes for producing them; caramel, candy, tablet confectionery, crackers, biscuits, cookies, pie, chocolate, snacks, etc.
  • carbonated beverages such as cola beverages, carbonated beverages containing fruit juice, carbonated beverages containing milk
  • Cosmetics include, for example, perfumes; hair care products such as shampoos, rinses, hair creams, pomades; cosmetics such as oscillating and lipsticks; facial soaps, body soaps, laundry soaps, laundry detergents, disinfectants Health and hygiene detergents such as detergents and deodorants; Health and hygiene materials such as toothpaste, tissue paper, and toilet paper; Fragrance products such as indoor fragrances and carcolon;
  • Example 1 Production of purified orange essential oil 1072.0 g of a commercially available Valencia orange essential oil (Comparative product 1) was subjected to thin-film distillation using a molecular distillation apparatus at a pressure of 500 Pa, a heating temperature of 80 ° C., and a wiper rotation speed of 300 rpm. And 1030.8 g of distillate and 32.7 g of residue were obtained. The residue was again subjected to thin-film distillation under the same conditions to obtain 5.1 g of a distillate and 27.9 g of a residue. A total of 1035.9 g of the distillate obtained by the thin-film distillation treatment is 1.5 kPa at a distillation temperature of 55 to 65 ° C.
  • Reference Example 1 Manufacture of orange terpeneless essential oil 450.8 g of Comparative Product 1 was depressurized using a McMahon packing packed distillation column at 1.5 kPa, distillation temperature 50-60 ° C, heating temperature 55-65 ° C. Distillation and distilling terpene hydrocarbons yielded 131.4 g of orange terpeneless essential oil (Comparative Product 2).
  • Example 2 GC-MS Measurement of Orange Essential Oil Invention Product 1, Comparative Products 1-2, Commercial Orange Oil Liquid Extract (Comparative Product 3), and Commercial Orange Oil Liquid Extract Terpen Free Product (Comparative Product) 4)
  • the volatile components were measured using GC-MS for the above five products.
  • the proportion of the compound was calculated by calculating the ratio of the total ion chromatogram area value of the compound to the total ion chromatogram area value of the entire mass spectrum.
  • the results of the existence ratio were classified into monoterpene hydrocarbons, oxygen-containing volatile components, sesquiterpene hydrocarbons, and other volatile components.
  • GC-MS measurement conditions GC conditions, column: InertCapWAX (60 m ⁇ 0.25 mm, film thickness 0.25 ⁇ m), temperature rise conditions: 40 ° C. to 230 ° C., 5.0 ° C./min temperature rise, hold at 230 ° C. for 30 minutes , Carrier gas: helium, linear velocity: 25 cm / sec MS conditions, measurement mode: EI / SCAN, 70 eV, MS temperature: 230 ° C. (ion source), 150 ° C. (quadrupole), scan range: 35-350 amu Table 1 shows the result of the existence ratio in each classification.
  • Comparative product 4 is a product generally called a terpene-free product from which hydrocarbons have been removed by liquid-liquid extraction. Since hydrocarbons have been removed, the proportion of monoterpene hydrocarbons and sesquiterpene hydrocarbons is low.
  • Example 3 Ratio of non-volatile components of orange essential oil Residue and thin film distillation treatment of orange essential oil of a total of three products of the present invention product 1 and comparative products 1 and 4 under the conditions shown in Example 1 The ratio with the orange essential oil subjected to was calculated, and this was defined as the ratio of the nonvolatile component.
  • Table 2 shows the ratio of nonvolatile components of the present invention product 1 and comparative products 1 and 4.
  • Example 4 Orange essential oil solubility test
  • the solubility test of the product 1 of the present invention and the comparative product 1 in an organic solvent was conducted.
  • the solvent used was an aqueous solution of 50 to 100% by mass of propylene glycol and ethanol, 1% by mass of orange essential oil was dissolved in the solvent, and the absorbance of the orange essential oil solution was evaluated according to the following turbidity measurement method.
  • Turbidity measurement method Absorbance at 680 nm when 1% of the sample of the product 1 of the present invention and the comparative product 1 was dissolved in each solvent shown in Table 3 using ion-exchanged water as a blank was measured by JASCO V- Measurements are made at 25 ° C. using a 560 UV-Vis spectrophotometer.
  • the aqueous solution with an ethanol concentration of 50 to 100% by mass is an aqueous solution in which 50 to 100% by mass of ethanol is mixed with 100% by mass of water. The results are shown in Table 3.
  • the product 1 of the present invention was transparently dissolved in an aqueous solution having an ethanol concentration of 60 to 90% by mass, but the absorbance was slightly increased in an aqueous solution having an ethanol concentration of 50% by mass.
  • Comparative Product 1 was transparently dissolved in an aqueous solution having an ethanol concentration of 80 to 90% by mass, but the aqueous solution having an ethanol concentration of 70% by mass or less was not transparently dissolved and the absorbance was increased. .
  • Example 5 Orange Essential Oil Abuse Test
  • the inventive product 1 and comparative products 1 to 4 were subjected to heat abuse and light abuse tests.
  • the product 1 of the present invention and the comparative products 1 to 4 were dissolved in an aqueous solution of 70% by mass of ethanol.
  • the present invention product 1 was dissolved in an ethanol aqueous solution by 0.4 mass%
  • the comparative product 1 was 20 mass%
  • the comparative product 2 was 6 mass%
  • the comparative product 3 was 5 mass%
  • the comparative product 4 was 0.5 mass%.
  • Comparative products 1 to 3 had a high proportion of hydrocarbons and did not dissolve the hydrocarbons, so the insoluble portion was removed to obtain an aqueous ethanol solution.
  • the dissolved product of this ethanol aqueous solution was flavored to beverages according to the formulation shown in Table 4.
  • Comparative product 1 is an orange essential oil that has not been subjected to terpene-less treatment, but terpene hydrocarbons are dissolved in the ethanol aqueous solution, and non-volatile components also exist, so that a lot of off-flavor was generated when abused. It is considered a thing. Moreover, it was shown that the comparative product 4 has a slightly deteriorated odor.
  • Example 6 Manufacture of purified lemon essential oil 1991.6 g of commercially available lemon essential oil (Comparative Product 5) was subjected to thin-film distillation using a molecular distillation apparatus at a pressure of 500 Pa, a heating temperature of 80 ° C., and a wiper rotation speed of 300 rpm. , 1857.3 g of distillate and 122.5 g of residue were obtained. The residue was again subjected to thin-film distillation treatment under the same conditions to obtain 64.7 g of a distillate and 58.4 g of a residue.
  • a total of 1922.0 g of the distillate obtained by the thin-film distillation treatment was used at 1.5 kPa, a distillation temperature of 43 to 65 ° C., and a heating temperature of 65 to 101 ° C. using a sulzer packing packed distillation column.
  • a distillation column packed with a sulzer packing was used and precision distillation was again performed under the conditions of 500 Pa, a distillation temperature of 40 to 55 ° C., and a heating temperature of 70 to 110 ° C.
  • 106.2 g of a refined lemon essential oil (Product 2 of the present invention) was obtained.
  • Reference Example 2 Manufacture of lemon terpeneless essential oil 400.2 g of Comparative Product 5 was depressurized using a McMahon packing packed distillation column at 1.5 kPa, distillation temperature 52-60 ° C, heating temperature 57-65 ° C. Distillation and distilling terpene hydrocarbons yielded 100.1 g of lemon terpeneless essential oil (Comparative Product 6).
  • Example 7 GC-MS Measurement of Lemon Essential Oil Invention Product 2, Comparative Products 5-6, Commercial Lemon Oil Liquid Extract (Comparative Product 7) and Commercial Lemon Oil Liquid Extract Extract Terpen Free Product (Comparative Product) 8)
  • the volatile components were measured using GC-MS for the above five products.
  • the proportion of the compound was calculated by calculating the ratio of the total ion chromatogram area value of the compound to the total ion chromatogram area value of the entire mass spectrum.
  • the results of the existence ratio were classified into monoterpene hydrocarbons, oxygen-containing volatile components, sesquiterpene hydrocarbons, and other volatile components.
  • the GC-MS measurement was performed under the same conditions as in the examples.
  • Table 6 shows the results of the existence ratio in each classification.
  • Comparative product 8 is a product generally called a terpene-free product from which hydrocarbons have been removed by liquid-liquid extraction. Since hydrocarbons have been removed, the proportion of monoterpene hydrocarbons and sesquiterpene hydrocarbons is low.
  • Example 8 Ratio of non-volatile components of lemon essential oil The residue and thin film distillation treatment of the lemon essential oil of a total of three products of the present invention product 2 and comparative products 5 and 8 under the conditions shown in Example 6 The ratio with the lemon essential oil subjected to 1 was calculated, and this was defined as the ratio of the nonvolatile component.
  • Table 7 shows the ratio of non-volatile components of the product 2 of the present invention and the comparative products 5 and 8.
  • Example 9 Lemon Essential Oil Solubility Test
  • the solubility test of the present invention product 2 and comparative product 5 in an organic solvent was conducted.
  • the solvent used was an aqueous solution of 50 to 100% by mass of propylene glycol and ethanol, 1% by mass of lemon essential oil was dissolved in the solvent, and the absorbance of the lemon essential oil solution was evaluated according to the same turbidity measurement method as in Example 4. .
  • the results are shown in Table 8.
  • the product 2 of the present invention was transparently dissolved in an aqueous solution having an ethanol concentration of 70 to 90% by mass, but the absorbance was slightly increased in an aqueous solution having an ethanol concentration of 60% by mass.
  • Comparative Product 5 was transparently dissolved in an aqueous solution having an ethanol concentration of 80 to 90% by mass, but an aqueous solution having an ethanol concentration of 70% by mass or less was not transparently dissolved, resulting in an increase in absorbance. .
  • a light absorbency will also become high in a propylene glycol solution.
  • Example 10 Lemon Essential Oil Abuse Test
  • the inventive product 2 and comparative products 5-8 were subjected to heat abuse and light abuse tests.
  • the product 2 of the present invention and the comparative products 5 to 8 were dissolved in an aqueous solution of 70% by mass of ethanol.
  • 1% by mass of the product 2 of the present invention, 20% by mass of the comparative product 5, 5% by mass of the comparative product 6, 5% by mass of the comparative product 7 and 1% by mass of the comparative product 8 were dissolved in the ethanol aqueous solution.
  • Comparative products 5 to 7 had a high proportion of hydrocarbons and the hydrocarbons were not dissolved. Therefore, insoluble portions were removed to obtain an ethanol aqueous solution.
  • the dissolved product of this ethanol aqueous solution was flavored to a beverage according to the formulation shown in Table 4 of Example 5.
  • Comparative product 5 is a lemon essential oil that has not been treated with terpene, but terpene hydrocarbons are dissolved in the aqueous ethanol solution, and there are also non-volatile components, so a lot of off-flavor was produced when abused. It is considered a thing.
  • the terpene free product of the comparative product 8 has a deteriorated odor of oil.
  • the products 1 and 2 of the present invention which do not contain a non-volatile component and have a monoterpene hydrocarbon content of 5% or less can be easily dissolved in propylene glycol or an aqueous ethanol solution, It was shown that the aroma is hardly impaired even under irradiation conditions.

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Abstract

La présente invention permet d'obtenir un produit purifié d'huile essentielle d'agrumes, présentant une teneur en hydrocarbures monoterpéniques de 5 % en masse ou moins, même si la température de chauffage pendant la distillation est basse, grâce aux fait suivants : une aptitude à l'élimination des constituants non volatils tout en réduisant au minimum la perte de constituants aromatiques, par une distillation à pression constante, en film mince, des constituants non volatils qui sont résistants à la dissolution dans un solvant hydrophile de l'huile essentielle d'agrumes ; et une distillation des hydrocarbures terpéniques par superfractionnement d'un distillat obtenu par la distillation en film mince. L'invention concerne un procédé de purification d'huile essentielle d'agrumes se dissolvant de manière transparente dans le solvant hydrophile par un procédé qui peut être facilement réalisé à l'échelle industrielle.
PCT/JP2015/080879 2015-01-30 2015-11-02 Huile essentielle d'agrumes soluble de manière transparente dans un solvant hydrophile et procédé de production d'huile essentielle d'agrumes WO2016121186A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018083032A1 (fr) 2016-11-07 2018-05-11 Arcelik Anonim Sirketi Dispositif d'extraction d'arôme
WO2018103956A1 (fr) 2016-12-07 2018-06-14 Arcelik Anonim Sirketi Dispositif d'extraction d'arôme
CN110200310A (zh) * 2019-03-20 2019-09-06 福建绿色黄金生物科技有限公司 一种用于电子烟的乌龙茶和柠檬的组合物及其应用
CN110200311A (zh) * 2019-03-20 2019-09-06 福建绿色黄金生物科技有限公司 一种用于电子烟的乌龙茶和柠檬的组合物及其应用
CN112457918A (zh) * 2020-11-17 2021-03-09 哈工大机器人南昌智能制造研究院 一种柑橘香精油系列产品的制备方法及应用
CN113201401A (zh) * 2021-04-08 2021-08-03 华南理工大学 一种柑橘类果皮精油及其制备方法与应用
WO2022101424A1 (fr) 2020-11-16 2022-05-19 Firmenich Sa Extrait d'huile d'agrumes
CN115558003A (zh) * 2022-09-30 2023-01-03 台州学院 柑橘皮中提取柑橘精油及橙皮苷的方法
WO2023063193A1 (fr) * 2021-10-13 2023-04-20 高砂香料工業株式会社 Produit purifié d'essence d'agrumes et procédé de production du produit purifié d'essence d'agrumes

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JP2008079558A (ja) * 2006-09-28 2008-04-10 Shiono Koryo Kk 超臨界向流抽出により製造される呈味改善剤

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JPS63118399A (ja) * 1986-11-07 1988-05-23 株式会社資生堂 テルペンレス精油
JPH06108088A (ja) * 1992-09-30 1994-04-19 Ogawa Koryo Kk テルペンレスオイルの製造法
JP2002146385A (ja) * 2000-11-06 2002-05-22 Japan Tobacco Inc タバコ臭気消臭用香料組成物
JP2008079558A (ja) * 2006-09-28 2008-04-10 Shiono Koryo Kk 超臨界向流抽出により製造される呈味改善剤

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018083032A1 (fr) 2016-11-07 2018-05-11 Arcelik Anonim Sirketi Dispositif d'extraction d'arôme
WO2018103956A1 (fr) 2016-12-07 2018-06-14 Arcelik Anonim Sirketi Dispositif d'extraction d'arôme
CN110200310A (zh) * 2019-03-20 2019-09-06 福建绿色黄金生物科技有限公司 一种用于电子烟的乌龙茶和柠檬的组合物及其应用
CN110200311A (zh) * 2019-03-20 2019-09-06 福建绿色黄金生物科技有限公司 一种用于电子烟的乌龙茶和柠檬的组合物及其应用
WO2022101424A1 (fr) 2020-11-16 2022-05-19 Firmenich Sa Extrait d'huile d'agrumes
CN112457918A (zh) * 2020-11-17 2021-03-09 哈工大机器人南昌智能制造研究院 一种柑橘香精油系列产品的制备方法及应用
CN113201401A (zh) * 2021-04-08 2021-08-03 华南理工大学 一种柑橘类果皮精油及其制备方法与应用
WO2023063193A1 (fr) * 2021-10-13 2023-04-20 高砂香料工業株式会社 Produit purifié d'essence d'agrumes et procédé de production du produit purifié d'essence d'agrumes
CN115558003A (zh) * 2022-09-30 2023-01-03 台州学院 柑橘皮中提取柑橘精油及橙皮苷的方法

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