Classifications

• • 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
  • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
  • A23L2/38—Other non-alcoholic beverages
• • 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
  • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
• • 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
• • 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

Definitions

• the present invention relates to an oil-in-water emulsified fragrance composition containing a high amount of a terpene hydrocarbon fragrance compound (excluding limonene) and a food or drink containing the same. Furthermore, the present invention relates to a food or drink containing the oil-in-water emulsified fragrance composition and a water-soluble fragrance.
• Non-Patent Document 1 A perfume compound having relatively low polarity and are difficult to dissolve in water or other aqueous solvents (that is, exhibit oil solubility).
• food and drink are easy to eat in a form containing a lot of water, and many foods and drinks contain a large amount of water. Therefore, in order to stably blend a desired amount of a fragrance compound into a food or drink containing a large amount of water, water-soluble fragrances and emulsified fragrances having improved solubility or dispersibility in the aqueous solvent of the fragrance compounds have been proposed ( For example, Non-Patent Document 1).
• Water-soluble fragrance refers to a liquid obtained by dissolving an oil-soluble liquid containing essential oils, natural fragrances, synthetic fragrances, etc. with water-containing ethanol or non-alcohol solvents such as propylene glycol (those using water-containing ethanol are essence fragrances). Also called). Water-soluble fragrances are commonly used in foods and drinks that require transparency, such as beverages, because they usually dissolve transparently in an aqueous solvent such as water and express a top-flavored flavor.
• a method using a solvent having a relatively low polarity is known as a method for incorporating a fragrance compound as much as possible into a water-soluble fragrance.
• a method for obtaining a water-soluble fragrance containing a large amount of a fragrance compound by extracting citrus oil with a specific alcohol and propylene glycol (Patent Document 1), and a high-concentration hydrous ethanol from an essential oil obtained from an edible material
• Patent Document 2 A method for obtaining a low-alcoholic beverage by blending an extract obtained by extraction in (Patent Document 2) has been proposed.
• the type or amount of the fragrance compound that can be contained in the water-soluble fragrance is limited to some extent, it is difficult to give the water-soluble fragrance a sufficient titer and various flavors alone, and it is constant.
• the water-soluble fragrance containing the fragrance compound in an amount greater than the amount cannot guarantee the stability of the fragrance compound and the transparency of the food or drink when blended in the food or drink.
• terpene hydrocarbon fragrance compounds which are contained in citrus peels and have isoprene as a structural unit, have low polarity and very low water solubility, do not contribute to flavor, and are more susceptible to deterioration.
• an oil obtained by removing or reducing terpenes containing a terpene hydrocarbon fragrance compound from citrus essential oil, that is, a terpene-less treated oil is used as a fragrance or a fragrance raw material (Patent Document 3).
• the emulsified fragrance is obtained by mixing an oil-soluble liquid containing a fragrance compound such as essential oil, natural fragrance, and synthetic fragrance into a mixed liquid such as an emulsifier, a water-soluble polysaccharide, a sugar alcohol, and water, followed by stirring. It refers to a liquid containing emulsified particles that contain a fragrance compound.
• the emulsified flavor can stably disperse a flavor compound having low water solubility in food and drink.
• the emulsified fragrance can give the food and drink a rich taste such as a body feeling, but due to the decrease in the volatility of the fragrance compound due to emulsification, the flavor development is slower than the water-soluble fragrance, and the light fragrance does not appear. weak. Some perfume compounds are difficult to emulsify (acids, esters, etc.), and the range of flavors that can be imparted is limited.
• the problem to be solved by the present invention is a versatile fragrance composition that contributes to the improvement or enhancement of a balanced flavor for various foods and drinks that could not be achieved by conventional water-soluble fragrances and emulsified fragrances.
• flavor composition which is stable in a fragrance
• the present inventors have conducted intensive research in view of the above problems.
• a product obtained by removing or reducing a terpene hydrocarbon fragrance compound from the essential oil is often used.
• terpene hydrocarbon fragrance compounds other than limonene are not so much contained in citrus essential oil, but there was no idea of adding them in a large amount to fragrances and foods and drinks.
• an oil-in-water emulsified fragrance composition containing a high content of terpene hydrocarbon fragrance compounds (excluding limonene) is prepared and blended in various foods and drinks alone or in combination with fruit juice and water-soluble fragrances.
• flavor and / or taste (hereinafter also referred to as “flavor”) was imparted to, improved and / or enhanced, and a completely surprising result was obtained in which a well-balanced flavor and natural feeling were obtained.
• the present invention is based on a completely new idea of selectively containing a terpene hydrocarbon fragrance compound in an oil-in-water emulsified fragrance composition.
• An oil-in-water emulsified fragrance composition containing the following (A), (B), and (C).
• (A) Fragrance The following fragrance compounds of (a) and (b) are contained in the following ratio with respect to the total amount of fragrance: (a) Terpene hydrocarbon fragrance compound (excluding limonene): 10% by mass or more (b) Limonene : 0% by mass or more and less than 50% by mass (B) Emulsifier (C) One or more selected from the group consisting of saccharides, ethanol and polyhydric alcohol [2]
• (A) A fragrance is further (c) oxygen-containing The oil-in-water emulsified fragrance composition according to [1] above, wherein the fragrance compound is contained in an amount less than 90% by mass based on the total amount of the fragrance (A).
• the terpene hydrocarbon fragrance compound of (a) is alloocimene, ocimene, myrcene, dihydromyrcene, ⁇ -farnesene, ⁇ -farnesene, ⁇ -pinene, ⁇ -pinene, camphene, ⁇ -ferrandrene, ⁇ - Terpinene, ⁇ -terpinene, ⁇ -terpinene, 3-carene, p-cymene, ⁇ -bisabolen, ⁇ -bisabolen, ⁇ -bisabolen, ⁇ -cedrene, ⁇ -cedrene, ⁇ -caryophyllene, ⁇ -caryophyllene, ⁇ -caryophyllene, ⁇ -
• the oil-in-water emulsified fragrance composition of the present invention can be used as a flavor and / or taste imparting, improving and / or enhancing agent for foods and beverages.
• the emulsified fragrance composition of the present invention can be used in combination with various water-soluble fragrances, and can impart flavors and natural feelings that have a much better balance compared to single use of water-soluble fragrances to various flavored foods and drinks.
• a specific emulsifier is used, even if it is blended with a food or drink that does not substantially contain alcohol (that is, has a high polarity) such as a non-alcoholic beverage, the transparency can be maintained without causing turbidity or neck ring. Therefore, the emulsified fragrance composition of the present invention is very versatile.
• a fragrance compound having a low emulsification stability together with the terpene hydrocarbon fragrance compound (for example, , Esters) can also be stably encapsulated in the emulsified particles. Therefore, the range of flavors that can be imparted to food and drinks is greatly expanded.
• the oil-in-water emulsified fragrance composition of the present invention (hereinafter also simply referred to as an emulsified fragrance composition) contains the following components (A), (B), and (C).
• fragrance compounds of (a) and (b) are contained in the following ratio with respect to the total amount of fragrance: (a) Terpene hydrocarbon fragrance compound (excluding limonene): 10% by mass or more (b) Limonene : 0% by mass or more and less than 50% by mass (B) Emulsifier (C) One or more selected from the group consisting of saccharides, ethanol and polyhydric alcohols The components (A) to (C) and Other compounds that may be contained in the emulsified fragrance composition will be described.
• the emulsified fragrance composition of the present invention contains a fragrance as the component (A).
• Component (A) contains component (a), which is a terpene hydrocarbon fragrance compound excluding limonene, as an essential component.
• the component (A) may further contain limonene as the component (b), and may further contain other perfume compounds and / or compositions.
• terpene hydrocarbon fragrance compound that can be used in the component (a) of the emulsified fragrance composition of the present invention (hereinafter also simply referred to as “terpene hydrocarbon”) is a hydrocarbon compound having isoprene as a structural unit, It is highly contained in the emulsified fragrance composition of the present invention, and one or more kinds excluding limonene can be used.
• the ratio of the component (a) to the total amount of the component (A) is preferably 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 40% by mass or more, 50 It may be at least mass%, at least 60 mass%, at least 70 mass%, at least 80 mass%, at least 90 mass%, or at least 95 mass%.
• the amount of each terpene hydrocarbon is arbitrary if the proportion of component (a) in the total amount of component (A) is 10% by mass or more. Can do.
• component (A) can contain limonene as component (b).
• the proportion of component (b), that is, limonene, relative to the total amount of component (A) is usually less than 50% by mass.
• limonene is a terpene hydrocarbon that is very abundant (for example, about 90% by mass) in citrus peels and is considered to be contained in large amounts in citrus essential oils and emulsified fragrance compositions thereof.
• the ratio of limonene to the total amount of component (A) in the emulsified fragrance composition is less than 50% by mass, and terpene hydrocarbons other than limonene, that is, not necessarily rich in the skin like limonene.
• a compound that is not included is selectively contained in the emulsified fragrance composition in a high amount so that it can be highly blended in food and drink in an unprecedented amount.
• the proportion of limonene relative to the total amount of component (A) is preferably less than 50% by weight and may be less than 40% by weight, less than 30% by weight, less than 20% by weight, less than 10% by weight, or less than 5% by weight.
• the component (A) may not contain limonene (that is, the ratio of limonene to the total amount of the component (A) may be 0% by mass).
• Component (A) may further contain an oxygen-containing fragrance compound as component (c).
• the oxygen-containing fragrance compound means a fragrance compound containing an oxygen atom in the molecule.
• the oxygen-containing fragrance compound that can be used in the present invention is not particularly limited.
• a fragrance compound containing oxygen in the molecule described in “Synthetic fragrance chemistry and product knowledge” described above, Fragrances Part II Food Fragrances, P88-131, issued on Jan. 14, 2000 contains fragrance compounds, natural fragrances, and synthetic fragrances contained in natural essential oils that contain oxygen atoms in their molecules.
• Specific examples of the oxygen-containing fragrance compound that can be used as the component (c) are given below.
• the compound which can be used for the component (c) of this invention is not limited to the following exemplary compounds.
• Aldehyde compounds that can be used as the component (c) of the present invention include acetaldehyde, n-hexanal, n-heptanal, n-octanal, n-nonanal, 2-methyloctanal, 3,5,5-trimethylhexanal, Decanal, undecanal, 2-methyldecanal, dodecanal, tridecanal, tetradecanal, trans-2-hexenal, trans-4-decenal, cis-4-decenal, trans-2-decenal, 10-undecenal, trans- 2-undecenal, trans-2-dodecenal, 3-dodecenal, trans-2-tridecenal, 2,4-hexadienal, 2,4-decadienal, 2,4-dodecadienal, 5,9-dimethyl-4,8- Decajienar, Sitler , Dimethyloctanal, ⁇ -methylene citron
• lactone compounds include ⁇ -decalactone, jasmolactone, propylidenephthalide, ⁇ -hexalactone, ⁇ -2-decenolactone, ⁇ -dodecalactone, dihydrocoumarin, and coumarin.
• acids that can be used as component (c) of the present invention include dodecanoic acid, 2-decenoic acid, gellanic acid, 2-methylbutyric acid, 2-ethylbutyric acid, benzoic acid, phenylacetic acid, cinnamic acid, isobutyric acid, Isovaleric acid, 3-methylvaleric acid, 2-hexenoic acid, 2-methyl-2-pentenoic acid, 2-methylheptanoic acid, myristic acid, stearic acid, lactic acid, phenylacetic acid, pyruvic acid, myristic acid, stearic acid, And cyclohexanecarboxylic acid.
• the emulsified fragrance composition of the present invention may further contain a fragrance compound that is neither a terpene hydrocarbon fragrance compound nor an oxygen-containing fragrance compound, and examples thereof include nitrogen-containing and / or sulfur-containing compounds. It is done. Specifically, methyl anthranilate, ethyl anthranilate, methyl N-methylanthranilate, methyl N-2′-methylpentylidene anthranilate, ligantoral, dodecanenitrile, 2-tridecenenitrile, geranylnitrile, citronellilnitrile, 3,7-dimethyl-2,6-nonadienonitrile, indole, 5-methyl-3-heptanone oxime, thiogeraniol, limonenethiol, butyl anthranilate, cis-3-hexenyl anthranilate, phenylethyl anthranilate, Examples include, but are not limited to, c
• the ratio of the component (A) of the emulsified fragrance composition to the total amount of the component (A) of the fragrance compound or composition other than the essential component (that is, the component (a)) is not particularly limited. ) To 0% by mass or more and less than 99% by mass.
• the ratio of component (A) to the total amount of the emulsified fragrance composition is not particularly limited, but is 50% by mass, 40% by mass, 30% by mass, 20% by mass with respect to the total amount of the emulsified fragrance composition. Or more, 10% by weight or more, 5% by weight or more, 1% by weight or more, 0.5% by weight or more, 0.1% by weight or more, or 0.05% by weight or more. It is in the range of mass%.
• the emulsified fragrance composition of the present invention contains an emulsifier as component (B).
• the kind of emulsifier that can be used in the emulsified fragrance composition of the present invention is not particularly limited. Examples include one or more selected from glycerin fatty acid ester, gum arabic, quilla extract, modified starch, sucrose fatty acid ester, polysorbate, and lecithin.
• Examples of the glycerin fatty acid ester include monoglycerin fatty acid ester, diglycerin fatty acid ester, polyglycerin fatty acid ester, and the like, and the fatty acid portion includes palmitic acid, lauric acid, stearic acid, oleic acid, myristic acid, arachidic acid, and behenic acid. Is exemplified.
• Specific examples of the polyglycerin fatty acid ester include decaglycerin laurate, decaglycerin stearate, decaglycerin oleate, and decaglycerin myristate.
• Examples of sucrose fatty acid esters include those in which the fatty acid moiety is palmitic acid, stearic acid, arachidic acid, or behenic acid.
• the polyglycerol fatty acid ester used in the present invention may be a purified polyglycerol fatty acid ester.
• the degree of esterification of the purified polyglycerol fatty acid ester is less than 2.5, more preferably less than 2.3, even more preferably less than 2, and the unreacted polyglycerol content is less than 5% by weight, preferably 1% by weight. What was refine
• the degree of esterification for example, the methods described in Japanese Patent No. 4512022, Japanese Patent Application Laid-Open No. 2007-116930, Japanese Patent Application Laid-Open No.
• 2008-07955, etc. may be adopted. it can.
• purified polyglycerin fatty acid ester Even when blended in various beverages, it dissolves transparently (clear emulsion described later), and is subjected to severe conditions such as storage at high temperature and heating for sterilization. , Can maintain a sufficiently transparent state over a long period of time.
• emulsifiers may be used alone or in combination of several kinds.
• the ratio of component (B), that is, the emulsifier to the total amount of the emulsified fragrance composition of the present invention is not particularly limited. For example, it is usually 0.1 to 30% by mass, 0.2 to 25% by mass, or 1 to 6% by mass. It's okay.
• the emulsified fragrance composition of the present invention contains one or more selected from saccharides, ethanol, and polyhydric alcohols as component (C). These can exert an effect as an emulsification aid for stabilizing the emulsified particles.
• the saccharide and the polyhydric alcohol are not particularly limited and any conventionally known compound may be used.
• saccharides such as diglycerin, triglycerin, trimethylolpropane, sorbitol, maltitol, reduced starch, glucose, sucrose, maltose and the like, and mixtures of two or more thereof.
• the sugar may be liquid sugar, and examples of the liquid sugar include sucrose liquid sugar, glucose fructose liquid sugar, inverted liquid sugar, and reduced syrup.
• the ratio of component (C) to the total amount of the emulsified fragrance composition of the present invention is not particularly limited, and may be, for example, usually 30 to 90% by mass, preferably 45 to 89% by mass, and more preferably 64 to 88% by mass. However, it is not limited to these.
• the emulsified fragrance composition of the present invention may further contain any component other than the above components (A) to (C) as long as the effects of the present invention are not lost.
• any component other than the above components (A) to (C) as long as the effects of the present invention are not lost.
• such components are exemplified.
• the emulsified fragrance composition of the present invention may contain animal and vegetable oils and fats.
• Animal and vegetable oils and fats are not particularly limited, but vegetable oils such as soybean oil, rapeseed oil, corn oil, olive oil, palm oil, safflower oil, sunflower oil, rice oil, rice salad oil, sesame oil, palm oil, peanut oil and the like Hardened oil; animal fats such as beef tallow, pork fat, chicken oil, fish oil and the like, and hardened oil thereof; medium chain fatty acid triglyceride (MCT) and the like can be mentioned, and these can be used alone or in combination of two or more.
• the proportion of the animal and vegetable oils and fats in the emulsified fragrance composition of the present invention is not particularly limited. For example, 0.4 to 4 parts by mass or 1 part by mass of the component (A) of the emulsified fragrance composition, or It may be within the range of 0.8 to 2 parts by mass.
• the emulsified fragrance composition of the present invention may contain water.
• the emulsified fragrance composition containing water is highly miscible with water and can easily exist stably in an aqueous solvent.
• the proportion of water in the emulsified fragrance composition of the present invention is not particularly limited, but may be, for example, 2 to 20% by mass relative to the total amount of the emulsified fragrance composition.
• the emulsified fragrance composition of the present invention may contain an oil-soluble antioxidant.
• the oil-soluble antioxidant is not particularly limited.
• a conventionally known oil-soluble antioxidant can be used. Specific examples include tocopherol, rosemary extract, vitamin C palmitate, ascorbyl palmitate, sezamol, ⁇ -Oryzanol and the like.
• One of these oil-soluble antioxidants can be used, or two or more can be used in combination.
• the amount of the oil-soluble antioxidant used is not particularly limited and can be arbitrarily set. Examples thereof include 2 to 30% by weight, preferably 5 to 20% by weight, based on the total amount of component (A).
• the terpene hydrocarbon fragrance compound is susceptible to oxidative degradation, but is effective in preventing oxidative degradation by containing an oil-soluble antioxidant.
• the emulsified fragrance composition of the present invention may further contain a specific gravity adjusting agent.
• the specific gravity adjusting agent is used for adjusting the specific gravity of the emulsified fragrance composition to match the specific gravity of the beverage to be added.
• the type of the specific gravity adjusting agent is not particularly limited, and one or more conventionally known arbitrary ones may be used, and examples thereof include sucrose diacetate hexaisobutyrate (also called SAIB).
• the emulsified fragrance composition of the present invention may further contain other water-soluble or oil-soluble various components as long as the effects of the present invention are not hindered.
• Other components include, for example, water-soluble pigments (for example, food red No. 2, No. 3, No. 102, No. 104, No. 105 and No. 106; Food Yellow No. 4 and No. 5; Edible Green No. 3; synthetic tar dyes such as food blue No. 1 and No.
• cacao dye gardenia yellow pigment, gardenia blue pigment, gardenia green pigment, grape skin pigment, cochineal pigment, purple corn pigment, purple cabbage pigment, perilla pigment
• Natural pigments such as hibiscus pigment, red beet pigment, safflower pigment, lac pigment, turmeric pigment, caramel pigment
• oil-soluble pigment eg paprika pigment, anato pigment, tomato pigment, marigold pigment, Dunaliella carotene, carrot carotene , Palm oil carotene, ⁇ -carotene, astaxanthin, canthaxanthin, lycopene, chlorofu
• Water-soluble vitamins eg, vitamin C, vitamin B1, vitamin B2, vitamin B12, niacin, pantothenic acid, folic acid
• oil-soluble vitamins eg, vitamin A, vitamin D, vitamin E, vitamin K
• Perfume retention agent for example, ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl
• ⁇ Particle size of the emulsified fragrance composition of the present invention is not particularly limited, the particle size described below can be used.
• the average particle size of the emulsified particles may be measured using an arbitrary particle size measuring device, such as a dynamic light scattering particle size distribution meter or a laser diffraction particle size distribution measuring device, more specifically, a laser zeta electrometer ELS. It can be measured using -8000 (product name) (manufactured by Otsuka Electronics Co., Ltd.).
• the average particle size of the emulsified fragrance composition of the present invention may be 0.2 ⁇ m or less, 0.1 ⁇ m or less, or 0.08 ⁇ m or less, but is not limited thereto. If the particle size is small, it becomes a clear emulsion, which is preferable from the viewpoint of being able to be blended in transparent foods and drinks without impairing the transparency.
• the clear emulsion means an emulsified composition that is transparently dispersed even when added to a transparent food or drink, and the transparent means that the turbidity of the added food or drink is kept below a certain value.
• Any method and apparatus may be used to measure turbidity.
• the emulsified fragrance composition of the present invention is added to water (purified water such as pure water or ion-exchanged water) at a concentration of 0.1% by mass. It can be determined by diluting and measuring the absorbance (Abs.) At a measurement wavelength of 680 nm.
• the upper limit of the turbidity value is 0.10, 0.08, 0.06, 0.04, 0.02, 0.01. Or 0.008, preferably 0.02 or less, more preferably 0.01 or less, it can be called a clear emulsion, but it is not necessarily limited to these values.
• the turbidity of the food or drink to which the composition is added, particularly the beverage is constant even after standing for a certain period of time, for example, 24 hours, 3 days, or 1 week. For example, it is preferable to be not more than the above-described upper limit value.
• Examples of a method of making the emulsified fragrance composition of the present invention a clear emulsion include a method of using the above-described purified polyglycerin fatty acid ester as the emulsifier of the component (B).
• the emulsified fragrance composition of the present invention includes an oil phase part (oil-soluble component containing component (A)) containing a terpene hydrocarbon and an optional water phase part (water-soluble component containing components (B) and (C)). ) Can be produced by stirring and mixing in any known method.
• a water phase part and an oil phase part are mixed, and T.M. K.
• an emulsifier such as Robomix (registered trademark) (manufactured by Primics)
• the mixture is emulsified by stirring at a rotational speed of about 5000 rpm to about 10,000 rpm for about 5 minutes to about 20 minutes.
• any emulsifier such as a conventionally known high-pressure homogenizer or colloid mill may be used as long as it has an equal or higher emulsifying capacity.
• the water phase part and the oil phase part are mixed with a stirrer and pre-emulsified, and the resulting pre-emulsified liquid is emulsified with high-speed stirring using an emulsifier such as a homomixer or a homogenizer, the emulsification temperature
• an emulsified fragrance composition having an arbitrary average particle size (about 50 to 800 nm) can be obtained.
• the emulsified fragrance composition of the present invention is useful as a preparation material for a fragrance composition used in foods and drinks, cosmetics, hygiene products, pharmaceuticals, and the like.
• fragrance compounds for example, the fragrance compounds described in “Survey of food fragrance compounds in Japan” and “Synthetic fragrance chemistry and product knowledge” above
• essential oils and fruit juices. You may mix
• the perfume compound, perfume composition, essential oil, and fruit juice to be used in combination are not particularly limited.
• the water-soluble fragrance may be an essence fragrance using hydrous ethanol, an organic solvent such as propylene glycol, or both. As the water-soluble fragrance, any commercially available product may be used.
• Examples of essential oils that can be used in combination with the emulsified fragrance composition of the present invention include essential oils such as orange oil, lemon oil, and grapefruit oil.
• Examples of fruit juice that can be used in combination with the emulsified fragrance composition of the present invention include, but are not limited to, orange juice, lemon juice, grape juice, grapefruit juice, apple juice, peach juice, and pineapple juice.
• Examples of foods and drinks that can impart, improve, or enhance a natural or balanced flavor with the emulsified fragrance composition of the present invention include, for example, beverages, seasonings, dressings, frozen desserts, desserts, retort foods, processed meat products Examples include, but are not limited to, processed fishery products.
• the amount of the emulsified fragrance composition blended in these foods and drinks varies depending on the type and form of the food and drinks, but in general, the range of 0.005 to 2% by mass with respect to the total amount of food and drinks may be exemplified. it can.
• these foods and drinks include carbonated drinks such as cola drinks, carbonated drinks with fruit juice, carbonated drinks with milk; fruit juice drinks, vegetable drinks, sports drinks, honey drinks, soy milk, vitamin supplement drinks, mineral supplement drinks, nutrition Soft drinks such as drinks, nourishment drinks, lactic acid bacteria drinks, milk drinks; favorite drinks such as green tea, black tea, oolong tea, herbal tea, milk tea, coffee drinks; Chuhai, cocktail drinks, sparkling liquor, fruit liquor, condiment liquor, etc.
• Alcoholic beverages such as butter, cheese, milk, yogurt; desserts such as ice cream, lacto ice, ice confectionery, yogurt, pudding, jelly, daily desserts and mixes for producing them; caramel, candy, Tablets, crackers, biscuits, cookies, pies, Examples include confections such as chocolate and snacks, and mixes such as cake mixes for producing them; general foods such as breads, soups and various instant foods; and oral compositions such as toothpastes. It is not limited.
• fruit juice can be obtained by adding about 0.005 to 2% by mass of the emulsified fragrance composition of the present invention to a syrup such as fruit flavored food or drink or sugar acid water in combination with a water-soluble fragrance as appropriate. It can enhance so-called richness such as feeling, fruitiness, taste thickness, body feeling, improve the flavor balance of food and drink, and give a natural feeling.
• fruit juice sensation or fruit sensation is a sensation that forms a unique taste of fruit, and when added, it makes you feel that you have used more fruit juice or fruit than the amount of fruit juice or fruit you actually used.
• the thickness of the taste is a sensation that when the food or drink is contained in the mouth or when swallowed, the taste lasts for a while from the whole mouth to the back of the throat, and the taste is deep.
• the body feeling is a sense that the skeleton of the taste is solid, mellow and bulging, and brings strength to the overall taste (in this specification, the thickness of the taste and the body feeling are In addition, there is also a rich taste).
• the balance means the taste balance of the fruit, and means the sense that the above-mentioned taste thickness / body feeling, fruit juice feeling, fruit feeling, skin feeling, etc. are well harmonized in addition to the sourness and sweetness.
• the emulsified fragrance composition of the present invention is a blended fragrance blended in cosmetics, hygiene products, pharmaceuticals, etc., such as bergamot, geranium, rose, bouquet, hyacinth, orchid, floral, etc.
• a blended fragrance By blending with a blended fragrance, the characteristics of the fragrance can be more emphasized, and a well-balanced fragrance full of natural feeling can also be reproduced.
• Example 1 The stability of the water-soluble fragrance and emulsified fragrance composition containing the terpene hydrocarbon fragrance compound in an aqueous solvent was confirmed.
• a water phase part and an oil phase part were prepared according to the formulation shown in Table 1 below. K.
• the mixture was stirred for 10 minutes at 8000 rpm with Robomix (manufactured by Primics) to prepare an oil-in-water emulsified fragrance composition (Invention product 1, containing 3.7% by mass of ⁇ -caryophyllene).
• the average particle size of the obtained emulsified fragrance composition was 0.07 ⁇ m.
• the purified decaglycerin monostearate (degree of esterification 1.7) was prepared by the method described in Japanese Patent Publication 4512022.
• the present product 1 or the comparative product 1 is added to 0.1% by mass of pure water and then stirred, and a mixed solution containing 0.1% by mass of the present product 1 or the comparative product 1 (hereinafter referred to as a mixed solution, respectively).
• a mixed solution containing 0.1% by mass of the present product 1 or the comparative product 1
• Comparative Mixture 1 a mixed solution containing 0.1% by mass of the present product 1 or the comparative product 1
• Comparative Mixture 1 1 and referred to as Comparative Mixture 1
• each mixture was filled in a 200 ml clear glass bottle for beverage, stoppered, sterilized at 85 ° C. for 15 minutes, and then cooled.
• the obtained comparative mixed solution 1 was cloudy, but the mixed solution 1 was clear.
• the turbidity of the mixed liquid 1 and the comparative mixed liquid 1 was obtained as absorbance at a measurement wavelength of 680 nm, the turbidity was 0.008 and turbidity 0.10, respectively.
• each sterilized mixed solution was allowed to stand at a temperature of 20 ° C. for 1 week, and then visually checked for turbidity and occurrence of neck ring. Although the neck ring was formed in the comparative mixed liquid 1, the neck ring was not confirmed in the mixed liquid 1.
• the turbidity of mixture 1 and comparative mixture 1 after standing for 1 week was obtained as the absorbance at a measurement wavelength of 680 nm, which was 0.008 and 0.05, respectively.
• the emulsified fragrance composition of the present invention does not impair the transparency of the terpene hydrocarbon fragrance compound having low water solubility into a transparent liquid (pure water in this example) that does not substantially contain alcohol. It was confirmed that a large amount could be blended as it was.
• Example 2 Preparation of fragrance composition with high content of terpene hydrocarbon fragrance compound and effect on flavor (1) Effect on flavor by high blending of terpene hydrocarbons According to the two types of formulations shown in Table 3 below Apple flavors (Formulation A and Formula B) were prepared.
• Apple Flavor A Apple Flavor of Formula A
• Apple Flavor B Apple Flavor of Formula B containing a high amount of farnesene as a terpene hydrocarbon fragrance compound 0.071% by mass ethanol solution
• the sensory evaluation was carried out for each scent solution contained in a 30 ml sample bottle, and the scent of the bottle mouth and the scent smelled by smelling the odor paper impregnated with the solution.
• emulsified fragrance composition was carried out in the same manner as in Example 1.
• Table 4 shows the formulation.
• the one containing apple flavor A was designated as emulsified fragrance composition A (comparative product 2)
• the one containing apple flavor B was designated as emulsified fragrance composition B (present product 2).
• the measure of storage stability was the degree of change in the average particle size of each emulsified fragrance composition under high temperature storage conditions.
• the average particle diameters of emulsified flavors A and B were confirmed using a particle size distribution meter (manufactured by Malvern, Zetasizer Nano ZSP), and were 0.09 ⁇ m and 0.13 ⁇ m, respectively.
• the beverages A and B were allowed to stand in a constant temperature bath at 40 ° C., and the average particle diameters of the emulsified flavors A and B were observed on the 1st and 5th days after the start of the standing as in the case of the standing. They were 0.12 ⁇ m and 0.12 ⁇ m, respectively, after the day, and 0.2 ⁇ m and 0.13 ⁇ m, respectively, after 5 days of standing.
• the emulsified fragrance A containing a large amount of esters has an unstable particle size immediately after storage at a high temperature, suggesting that the emulsified state cannot be maintained.
• farnesene which is a terpene hydrocarbon
• the emulsified fragrance B contained in a high content can maintain the emulsified state stably with almost no change in the particle size.
• apple flavor A or B is approximately 60% by formulation shown in Table 5 below It was prepared by mixing and dissolving in water-containing ethanol.
• the product containing Apple Flavor A was named Essence Fragrance 1
• the product containing Apple Flavor 2 was named Essence Fragrance 2.
• Apple flavors A and B were both transparently dissolved in about 60% ethanol, and essence fragrances 1 and 2 were visually transparent.
• Beverages 1 to 4 were prepared by blending the obtained fragrance, that is, emulsified fragrance B, and essence fragrance 1 and 2 into the syrup of Table 6 as shown in Table 7 below.
• the flavor of each beverage and the stability of each fragrance composition in each beverage were evaluated. Specifically, for the flavor, sensory evaluation was performed by 10 skilled panelists immediately after preparation, and the stability evaluation was visually confirmed after standing for 2 weeks at a temperature of 20 ° C. (clarity and presence of neck ring). I went there.
• Table 7 below shows the average evaluation and stability of 10 panelists.
• Beverage 1 (Example) had a weak fragrance, which was thought to be due to a decrease in fragrance due to a decrease in volatility due to emulsification. It was also seen.
• Beverage 2 (Comparative Example) was a beverage using an essence fragrance (Essence fragrance 1) according to a general formulation, but it had good fragrance and freshness but lacked satisfaction and sustainability. This is thought to be due to the absence of farnesene.
• the beverage 3 (Comparative Example) had a good flavor immediately after preparation, but it was poor in stability in the beverage and the occurrence of neck rings that impair the flavor and aesthetics was observed, and the flavor persistence was also poor. .
• the cause of the neck ring was thought to be due to farnesene due to the difference in prescription between apple flavors 1 and 2.
• the beverage 4 was given a balanced flavor pronounced of the whole fruit, had satisfaction and a natural feeling, and also had good stability and sustainability.
• the emulsified fragrance composition with a high content of the terpene hydrocarbon fragrance compound of the present invention imparts a flavor to the beverage that gives the satisfaction of eating an entire apple when added to the beverage, and the beverage was confirmed to be clear and stable. Furthermore, when the emulsified fragrance composition containing a high content of the terpene hydrocarbon fragrance compound of the present invention and the essence fragrance (essence fragrance 1) according to a general prescription are used in combination, a flavor that cannot be imparted by the emulsified fragrance and the water-soluble fragrance alone is imparted. It was confirmed that it was possible. Therefore, in this Example, it was confirmed that the stability in the beverage can be maintained while imparting an unprecedented good flavor by selectively containing the terpene hydrocarbon in the emulsified flavor composition.
• Example 3 Example of combined use of emulsified fragrance composition of the present invention and water-soluble fragrance A water phase part and an oil phase part were prepared according to the formulation shown in Table 8 below. K. Two types of oil-in-water emulsified fragrance compositions (invention product 3 and comparative product 3) were prepared by stirring for 10 minutes at 8000 rpm with Robomix (registered trademark) (manufactured by Primix). When the average particle diameter of each obtained emulsified fragrance composition was measured in the same manner as in Example 2, both were 0.06 ⁇ m.
• flavor was prepared as follows.
• the obtained flavors that is, the product 3 of the present invention, the comparative product 3, and the essence flavor 3 are blended in a syrup (same as described in Table 6) as shown in Table 9 below, and three kinds of beverages (beverages 5-7) ) Was prepared.
• the emulsified fragrance composition of the present invention (Product 3 of the present invention) containing a high amount of terpene hydrocarbon is more water-soluble than the emulsified fragrance composition (Comparative product 3) containing terpene-less oil. It was confirmed that when used in combination with a fragrance, the food / beverage product has a significantly better flavor.
• Example 4 Example of combined use of emulsified fragrance composition of the present invention and water-soluble fragrance A water phase part and an oil phase part were prepared according to the formulation shown in Table 10 below.
• K Three types of oil-in-water emulsified fragrance compositions (present invention product 4, comparative product 4 and comparative product 5) were prepared by mixing with ROBOMIX (registered trademark) (manufactured by PRIMIX Corporation) while stirring at 8000 rpm for 10 minutes.
• the terpene hydrocarbon used is the same ⁇ -caryophyllene as in Example 1.
• the product 4 of the present invention and the comparative product 4 are known as compounds that impart a good bitterness to the taste of citrus fruits and the like. 4-menthyloxy-2-butanone was also blended (see Japanese Patent Application Laid-Open No. 2016-084418 and Japanese Patent No. 6001031).
• Comparative product 5 used commercially available 75% terpeneless grapefruit oil as the oil phase part.
• flavor was prepared as follows.
• Ethanol 600 g and water 400 g were mixed to obtain a mixed solvent.
• 100 g of American grapefruit cold press oil (limonene concentration: 84%, myrcene concentration: 3.5%) was added thereto, followed by stirring and extraction at 25 ⁇ 2 ° C. for 10 minutes. Subsequent steps were carried out in the same manner as in Example 3 to obtain a clear filtrate, and an essence flavor 4 was obtained.
• the obtained fragrances that is, the inventive product 4, the comparative product 4, the comparative product 5, and the essence fragrance 4 are blended into a syrup (same as Table 6) as shown in Table 11 below, and four kinds of beverages (Beverages 8) To 11) were prepared.
• the emulsified fragrance composition of the present invention containing a high content of terpene hydrocarbons is more water-soluble fragrance than the emulsified fragrance composition containing fragrance compounds other than terpene-less oil and terpene hydrocarbons.
• the food and drink had a particularly good flavor.
• Example 5 The effect of the emulsified fragrance composition of the present invention on the flavor of fruit juice The effect of the terpene hydrocarbon-rich emulsified fragrance composition of the present invention on the flavor of fruit juice was confirmed.
• Example 4 The emulsified fragrance composition prepared in Example 4 (present invention product 4) or the comparative product 5 (emulsified fragrance composition containing terpeneless oil) was added to the jelly having the following formulation, and a transparent jelly was prepared by a conventional method. Then, sensory evaluation was performed in the same manner as in Example 4.
• Example 4 the jelly to which the comparative product 5 was added had a good scent, but the flavor was weak and the balance after the middle was weak, so the balance was poor, while the jelly to which the product 4 of the present invention was added was a grapefruit Increased fruit juice feeling, fruit feeling and skin feeling will give a sense of satisfaction and natural flavor as if you are eating the whole fruit, and the overall flavor is well balanced, and the sustainability of the flavor is also good. It was.
• Example 6 Effect of emulsified fragrance composition of the present invention on fruit juice usage of food and drink The effect of the emulsified fragrance composition of the present invention on fruit juice usage of food and drink was confirmed.
• Example 4 the water-soluble fragrance (essence fragrance 4) and the emulsified fragrance composition (invention product 4) prepared in Example 4 were prepared.
• Example 7 Stability and flavor of various emulsified fragrance compositions containing various terpene hydrocarbon fragrance compounds and effects on flavor Stability and flavor of various terpene hydrocarbon fragrance compounds other than those used in Examples 1 to 6 The same test as in Examples 1 and 2 was conducted.
• terpene hydrocarbon fragrance compounds myrcene, camphene, ⁇ -ferrandrene, 3-carene, p-cymene (also called p-cymene), valencene, terpinolene, and kadinene
• myrcene, camphene, ⁇ -ferrandrene, 3-carene, p-cymene (also called p-cymene), valencene, terpinolene, and kadinene the following prescriptions are used.
• An emulsified fragrance composition was prepared (the same as in Table 1) (Invention products 5 to 12).
• Example 2 the obtained essence fragrance 1 (essence fragrance not containing a terpene hydrocarbon fragrance compound, the same as in Table 5) described in Example 2 was used as a syrup (same as in Table 6).
• Beverages 14 to 21 each containing 0.5% by mass and beverages (Comparative Example) in which only 1.0% by mass of Essence Fragrance 1 was added to the syrup were prepared. Sensory evaluation by a panelist was performed. Specifically, comments were recorded about the fruit juice feeling and the skin feeling of the example drinks compared to the comparative drinks.
• any emulsified fragrance composition containing a high content of the terpene-based hydrocarbon fragrance compound is sufficiently stable in an aqueous solvent, and when used in combination with a water-soluble fragrance, the flavor of food and drink is markedly increased. And it was confirmed that the balance improved.

Landscapes

• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Polymers & Plastics (AREA)
• Nutrition Science (AREA)
• Food Science & Technology (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Fats And Perfumes (AREA)
• Seasonings (AREA)
• Non-Alcoholic Beverages (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

Family

ID=63039767

Family Applications (1)

Country Status (4)

Cited By (2)

Families Citing this family (1)

Citations (15)

Family Cites Families (10)

• 2017
  • 2017-02-03 JP JP2017019024A patent/JP6847520B2/ja active Active
• 2018
  • 2018-01-26 WO PCT/JP2018/002573 patent/WO2018143103A1/ja active Application Filing
  • 2018-01-26 CN CN201880005075.5A patent/CN110049684A/zh active Pending
  • 2018-01-30 TW TW107103174A patent/TWI700045B/zh active

Patent Citations (15)

Non-Patent Citations (2)

Also Published As

Similar Documents

Legal Events