CN115667474A

CN115667474A - Taste-improving composition

Info

Publication number: CN115667474A
Application number: CN202180036300.3A
Authority: CN
Inventors: 萩森夏芽; 渡部真; 松田裕之; 平本忠浩; 大塚雅史
Original assignee: Lion Corp; Takasago International Corp
Current assignee: Lion Corp; Takasago International Corp
Priority date: 2020-05-19
Filing date: 2021-05-19
Publication date: 2023-01-31
Also published as: WO2021235481A1; JP2021181535A

Abstract

The present invention addresses the problem of providing a novel composition useful as a taste improvement agent for oils (essential oils) derived from plants of the genus Mentha of the family Labiatae, mint-based essences, and the like. The present invention relates to a composition derived from a plant of the genus Mentha of the family Labiatae, wherein the total mass of the contents of caryophyllene BE, germacrene D and melaleuca alternifolia is 15% by mass or more relative to the total mass of the composition. The present invention also relates to a composition containing caryophyllene BE, germacrene D, and globeflower, which are volatile fractions obtained by distilling a distillation residue obtained by distilling an oil derived from a plant belonging to the genus mentha of the family lamiaceae under reduced pressure, wherein the total mass of the content of caryophyllene BE, germacrene D, and globeflower is 15 mass% or more relative to the total mass of the composition.

Description

Taste-improving composition

Technical Field

The present invention relates to a composition comprising specific extracted ingredients derived from a mentha plant oil of the labiatae family comprising caryophyllene BE, geranylene D, and melaleuca alternifolia, and use thereof as a taste improver thereof, and a method for producing the same.

Background

In products such as oral care products, food and drink products, and perfume cosmetics that require a refreshing feel, mint-based essential oils and mint-based essences (flavors) such as peppermint, asian mint, and spearmint belonging to the genus mentha of the family labiatae are widely used for the purpose of imparting a suitable flavor and for the purpose of improving taste. However, if the content of the mint-based essential oil and the mint-based essence in oral care products, food and drink products, and food and drink products is too high, a strong bitter taste tends to emerge compared to the refreshing feeling, and the mint-based essential oil tends to be mixed unevenly in the products and turbid, so that a technique of enhancing only the refreshing feeling or uniformly dissolving the mint-based essential oil by a process of extracting the mint-based essential oil, or by combining another flavor component, alcohol, or the like with the mint-based essence has been studied.

For example, in patent document 1 (specification of U.S. Pat. No. 5298238), a technique for improving taste and turbidity of an oral care product containing a mint-based essential oil is disclosed. In the cited document 1, it is described that when a mint-based essential oil is produced, the "head" and "tail" of an oil mainly composed of terpenes such as monoterpenes and sesquiterpenes are removed by distillation under reduced pressure, and a composition having reduced bitterness and turbidity is obtained.

Further, patent document 2 (japanese patent laid-open No. 2003-253292) discloses a barrier property imparting agent for a mint flavor that enhances the laminate roll feeling, imparts barrier property, and matches the flavor of mint, and describes that the barrier property imparting agent is obtained by alcohol extraction of a residue obtained by precision distillation under reduced pressure of an essential oil.

Documents of the prior art

Patent document

Patent document 1: specification of U.S. Pat. No. 5298238

Patent document 2: japanese patent laid-open publication No. 2003-253292

Disclosure of Invention

As a flavor improving agent that improves more desirable natural and deep refreshing feeling (natural mint feeling) and favorable taste for mint-based essential oils or essences, a novel material is desired. Accordingly, an object of the present invention is to provide a novel composition useful as a taste improvement agent for oils (essential oils) derived from plants of the genus mentha of the family labiatae, mint-based essences, and the like.

The present inventors have made extensive studies to solve the above problems, and in the process, the present inventors have focused on a residue obtained by extracting peppermint oil by distillation and continuously discarded so far. Further, extensive experiments were repeated on whether or not the residue was newly utilized, and it was found that a volatile fraction obtained by further distilling the residue had a specific composition and that when it was added to peppermint oil, it was unexpectedly excellent in imparting or enhancing a more appropriate refreshing feeling and a refreshing feeling to oil (essential oil) and the like, and thus the present invention was completed.

That is, the present invention relates to the following [ 1] to [ 8 ].

[ 1] A composition derived from a plant of the genus Mentha of the family Labiatae, wherein the total mass of caryophyllene BE, germacrene D and melaleuca alternifolia alcohol is 15% by mass or more based on the total mass of the composition.

[ 2] A composition comprising caryophyllene BE, geranylene D and melaleuca alternifolia alcohol, which are volatile fractions obtained by distilling an oil derived from a plant belonging to the genus Mentha of the family Labiatae under reduced pressure, wherein the total mass of the content of caryophyllene BE, geranylene D and melaleuca alternifolia alcohol is 15% by mass or more relative to the total mass of the composition.

[ 3] the composition according to the above [ 1] or [ 2], wherein the above Mentha plants of Lamiaceae are selected from Mentha piperita, mentha viridis and Mentha arvensis.

[ 4] the composition according to any one of [ 1] to [ 3] above, which is a composition for improving the taste of a menthol-containing composition, and is added as follows:

the menthol-containing composition contains greater than or equal to 0.01 part by mass of caryophyllene BE, senecine D and melaleuca alternifolia total mass per 100 parts by mass of menthol.

[ 5] the composition according to any one of [ 1] to [ 3] above, which is a composition for improving the taste of a composition containing carvone, and is added as follows:

the total mass of caryophyllene BE, germacrene D and melaleuca alternifolia is 0.01 parts by mass or more relative to 100 parts by mass of carvone in the carvone-containing composition.

[ 6] A perfume composition comprising the composition according to any one of [ 1] to [ 5] above.

[ 7] A food or drink, a pharmaceutical product, a perfume cosmetic product or an oral care product comprising the flavor composition according to [ 6] above.

A method for producing the above composition, which comprises a first volatile fraction containing caryophyllene BE, geranylene D and melaleuca alternifolia alcohol, comprises the following steps (a) and (b):

(a) A step of distilling oil derived from a plant of the genus Mentha of the family Labiatae under reduced pressure to obtain a distillation residue of 3 to 25 mass% of the total amount of oil derived from a plant of the genus Mentha of the family Labiatae, and;

(b) A step of subjecting the distillation residue obtained in the step (a) to thin-film distillation to obtain a first volatile fraction in an amount of 5 to 50 mass% based on the total amount of the distillation residue,

the method may further comprise (c) a step of: a step of subjecting the first volatile fraction obtained in the step (b) to thin-film distillation to obtain a second volatile fraction in an amount of 50 to 95 mass% based on the total amount of the first volatile fraction,

the composition may contain the first volatile fraction or the second volatile fraction, and the total mass of the content of caryophyllene BE, germacrene D and melaleuca alternifolia alcohol is 15 mass% or more relative to the total mass of the composition.

The composition according to the above, wherein the oil derived from a plant of the genus Mentha of the family Labiatae is distilled under reduced pressure at a pressure of 0.00001 to 0.05 bar and a temperature of 40 to 250 ℃ to obtain a distillation residue in an amount of 3 to 25 mass% based on the total amount of the oil derived from a plant of the genus Mentha of the family Labiatae, and the distillation residue is subjected to thin film distillation to obtain a composition containing a volatile fraction in an amount of 5 to 50 mass% based on the total amount of the distillation residue,

the total mass of the content of caryophyllene BE, germacrene D and melaleuca alternifolia alcohol is 15 mass% or more relative to the total mass of the composition.

Effects of the invention

When the novel composition of the present invention is added to oils (essential oils) derived from plants of the genus mentha of the family labiatae, mint-based essences, and flavor compositions, various drink foods, pharmaceuticals, perfume cosmetics, oral care products, and the like containing the same, natural mint feeling can be imparted or enhanced, and preference can be improved at the same time.

Drawings

FIG. 1 is a flow chart showing one embodiment (examples 1 and 2) of a method for producing the composition of the present invention.

Figure 2 is a schematic diagram conceptually showing the volatile fraction of the composition of the present invention in oil (essential oil) from a plant of the genus mentha of the family labiatae.

Detailed Description

< composition >

The present invention relates to a composition derived from a plant of the genus Mentha of the family Labiatae, wherein the total mass of the content of caryophyllene BE, germacrene D and melaleuca alternifolia alcohol is 15% by mass or more relative to the total mass of the composition. The "composition derived from a plant of the genus mentha of the family labiatae" in the present invention means a composition containing 95% or more, preferably 98% or more, and more preferably 100% of a component derived from a plant of the genus mentha of the family labiatae.

One embodiment of the present invention is a composition containing a volatile fraction obtained by distilling an oil derived from a plant of the genus mentha of the family labiatae under reduced pressure, for example, distilling a distillation residue obtained by precision distillation under reduced pressure, particularly by thin film distillation. The total mass of the content of caryophyllene BE, geranylene D and melaleuca alternifolia alcohol is 15 to 50 mass%, preferably 15 to 40 mass%, more preferably 20 to 40 mass%, relative to the total amount of the composition. The "distillation residue" of the present invention may also be referred to as a raw material for obtaining the substance of the composition, and is referred to as a residue having a high boiling point component, which is left after distilling oil derived from a plant of the genus mentha of the family labiatae and recovering 75 mass% or more, for example 90 mass% or more of the oil derived from a plant of the genus mentha of the family labiatae as a volatile component. Here, the composition of the present invention contains various kinds of fragrance components that cannot BE analyzed, in addition to caryophyllene BE, big-senrene D, and melaleuca alternifolia, and it is difficult to identify all the components, and therefore, it is specified by the production method.

One embodiment of the composition of the present invention is specifically explained based on fig. 1 and 2, and the composition of the present invention is a composition containing or is composed of a volatile fraction (first volatile fraction) which is composed of: an oil (essential oil) derived from a plant belonging to the genus Mentha of the family Labiatae is subjected to precision distillation under a pressure of 0.00001 to 0.05 bar, preferably 0.002 to 0.04 bar, more preferably 0.004 to 0.03 bar, 40 to 250 ℃, preferably 60 to 180 ℃, more preferably 80 to 140 ℃, 75 to 97 mass%, preferably 92 to 96 mass%, of the total amount of the oil derived from the plant belonging to the genus Mentha of the family Labiatae is recovered as a volatile A, a distillation residue comprising 3 to 25 mass%, preferably 4 to 8 mass%, of the total amount of the oil derived from the plant belonging to the genus Mentha of the family Labiatae is obtained, and the distillation residue is subjected to thin film distillation to obtain a volatile B of 5 to 50 mass%, preferably 10 to 30 mass%, of the total amount of the distillation residue. The precise distillation conditions for obtaining the volatile fraction a are preferably carried out at a pressure of 0.002 to 0.04 bar and 60 to 180 ℃, more preferably at a pressure of 0.004 to 0.03 bar and 80 to 140 ℃, and the 3 components (caryophyllene BE, germacrene D and melaleuca alternifolia) of the composition of the present invention can BE concentrated in the distillation residue by precise distillation under such conditions. The distillation conditions for obtaining the volatile fraction (first volatile fraction) are preferably carried out at 90 to 180 ℃ at a pressure of 0.00001 to 0.01 bar, more preferably at 140 to 160 ℃ at a pressure of 0.002 to 0.008 bar.

The composition of the present invention is more preferably composed of the second volatile fraction, that is, the second volatile fraction is composed of the volatile fraction C obtained by thin-film distillation of the volatile fraction B, in an amount of 50 to 95% by mass, preferably 60 to 95% by mass, and more preferably 60 to 90% by mass, of the total amount of the volatile fraction B. The distillation conditions under which the second volatile fraction is obtained are preferably carried out at 90 to 180 ℃ and at a pressure of 0.00001 to 0.01 bar, more preferably at 140 to 160 ℃ and at a pressure of 0.002 to 0.008 bar. The second volatile fraction can remove components such as resins that cause off-flavors, as compared to the first volatile fraction.

The content of caryophyllene BE, big senecine D and cajeput in of the present invention can BE measured by a general aroma component analysis, for example, a combination of GC-MS analysis and GC-FID analysis, and the values obtained by the method described in the present example can BE measured.

In the mode of the volatile portion a obtained by distilling an oil (i.e., an essential oil) derived from a plant of the genus mentha of the family labiatae or an essential oil derived from a plant of the genus mentha of the family labiatae under reduced pressure, the total mass of caryophyllene BE, germacrene D and melaleuca alternifolia is less than 15 mass% of the total mass of the volatile portion a, and is different from the composition of the component constituting the composition of the present invention. The volatile fraction (volatile portion B) contained in the composition of the present invention and obtained by distilling the distillation residue is completely different in composition from the nonvolatile portion B and the nonvolatile portion C obtained simultaneously in the distillation process, and particularly contains almost no odorous components such as resins. The composition of the present invention contains various aroma components that cannot BE analyzed in addition to caryophyllene BE, big-senone D and melaleuca alternifolia, but it is difficult to identify all the components, and therefore, the composition can BE specified by the production method.

If caryophyllene BE, germacrene D and melaleucyl alcohol are contained in the composition of the present invention, the composition ratio thereof is not particularly limited, but caryophyllene BE: big myrcene D: the mass ratio of the anthocyanin to the anthocyanin is 1:1 to 2.5:1 to 5.

The type of the "plant belonging to the genus Mentha of the family Labiatae" of the present invention is not particularly limited, and preferable examples thereof include Mentha piperita (Mentha x piperita), mentha arvensis (Mentha arvensis), mentha viridis species (Mentha spicata), and Mentha arvensis species (Mentha gracilis) of Mentha viridis.

The "oil derived from a plant of the genus Mentha of the family Labiatae" of the present invention is an essential oil obtained by extracting a plant of the genus Mentha of the family Labiatae (which may be any part of a plant body such as a leaf, a stem, a flower, or a root) by a known method such as distillation, and contains l-menthol or l-carvone as a main aroma component. Specific examples thereof include peppermint oil, spearmint oil and the like. Here, in the present specification, the "main aroma component" refers to a component having an aroma among volatile components contained in the plants of the genus mentha of the family labiatae, which is usually contained in the largest amount, clearly shows the characteristics of the aroma of each plant of the genus mentha of the family labiatae, and is a component that greatly affects the intensity of the aroma. For example, the main flavor component of peppermint, asian mint is l-menthol, and the main flavor component of spearmint is l-carvone. The oil derived from a plant of the genus Mentha of the family Labiatae can be obtained by using commercially available essential oil, for example, by subjecting a plant of the genus Mentha of the family Labiatae to any one of the known methods such as supercritical carbon dioxide extraction, distillation, steam distillation, and solvent extraction. The oil derived from a plant of the genus mentha of the family labiatae is obtained under conditions of a low temperature in the extraction step, for example, a temperature of 70 ℃ or lower, and preferably at pH6 to 9, more preferably at pH6 to 8. In the extraction step, a solvent such as water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, propylene glycol, glycerol, acetone, methyl acetate, ethyl acetate, hexane, heptane, edible oils and fats, and MCT can be used. The preferable solvent is water, methanol, ethanol, acetone, ethyl acetate, hexane, heptane, edible oil and fat, MCT. These solvents may be used alone, or 2 or more of them may be used in combination.

The composition of the present invention is preferably added to a menthol-containing composition (including a flavor composition, a drink and food product, a pharmaceutical product, a perfume cosmetic product, an oral care product, and the like described later) in an amount such that the total mass of caryophyllene BE, geranylene D, and melaleuca alternifolia can BE contained in an amount of 0.01 to 50 parts by mass, more preferably 0.05 to 10 parts by mass, and still more preferably 0.1 to 1 part by mass, relative to 100 parts by mass of menthol contained in the menthol-containing composition. By including the composition of the present invention in the menthol-containing composition at the above content, a natural and deep refreshing feeling can be provided from the menthol-containing composition, and the preference of the menthol-containing composition can be improved.

The composition of the present invention is preferably added to a carvone-containing composition (including a flavor composition, a drink and food product, a pharmaceutical product, a perfume cosmetic product, an oral care product, and the like described later) in an amount such that the total mass of caryophyllene BE, geranylene D, and melaleuca alternifolia can BE contained in an amount of 0.01 to 50 parts by mass, more preferably 0.05 to 10 parts by mass, and still more preferably 0.1 to 1 part by mass, relative to 100 parts by mass of carvone contained in the carvone-containing composition. By including the composition of the present invention in the carvone-containing composition at the above content, the composition containing carvone provides a natural and deep cool and refreshing feeling and can improve the preference of the carvone-containing composition.

The "menthol-containing composition" of the present invention is not particularly limited as long as it contains l-menthol known as a main component of mint flavor (mint flavor), and examples thereof include essential oil of peppermint and essential oil of peppermint of asia. The term "menthol-containing composition" is a concept including a perfume composition and a product described later, and may include any component such as a perfume component and an essential oil in addition to menthol.

The "carvone-containing composition" of the present invention is not particularly limited as long as it contains l-carvone known as a main component of peppermint flavor, and may be spearmint essential oil, for example. The "carvone-containing composition" is a concept including a fragrance composition and a product described later, and may include any fragrance component, essential oil, and other components in addition to carvone.

The composition of the present invention may be in a liquid form or a powder form (solid form), and the form thereof is not particularly limited. For example, the composition may BE in the form of a liquid in which a suitable solvent such as caryophyllene BE, geranylene D, or patchouli alcohol is dissolved, for example, water, ethanol, glycerin, propylene glycol, triacetin, medium-chain fatty acid glyceride, or an edible oil or fat such as an edible vegetable oil (e.g., rice salad oil) is dissolved.

< method for producing composition >

A method for producing a composition according to an embodiment of the present invention will be described with reference to fig. 1.

First, as the step (a), an oil derived from a plant of the genus mentha of the family labiatae, for example, an essential oil such as peppermint oil, and spearmint oil is prepared, and distillation, preferably precision distillation, is performed under conditions of, for example, 40 to 250 ℃, preferably 60 to 180 ℃, more preferably 80 to 140 ℃, and at a pressure of 0.00001 to 0.05 bar, preferably 0.002 to 0.04 bar, more preferably 0.004 to 0.03 bar to obtain a distillation residue. In this case, it is preferable that 75 to 97% by mass, and more preferably 92 to 96% by mass of the oil derived from a plant of the genus Mentha of the family Labiatae is recovered as a volatile fraction (volatile portion A). One of the distillation residues consisting of the nonvolatile fractions A obtained at the same time is used as a substantial raw material of the composition of the present invention.

Next, as the step (B), the obtained distillation residue (non-volatile portion a) is subjected to thin film distillation to obtain a first volatile fraction (volatile portion B). In the present step, the first volatile fraction (volatile portion B) is preferably obtained by thin film distillation under conditions of a hot solvent temperature of 90 to 180 ℃, a pressure of 0.00001 to 0.01 bar, preferably 140 to 160 ℃, and a pressure of 0.002 to 0.008 bar, for example. In this case, in the composition of the present invention, 5 to 50% by mass, preferably 10 to 30% by mass of the nonvolatile portion a is recovered as the first volatile fraction (volatile portion B), and preferably 50 to 95% by mass, preferably 70 to 90% by mass is regarded as the nonvolatile portion B. The first volatile fraction (volatilization section B) may BE any one of caryophyllene BE, geranylene D and melaleuca alternifolia in a total mass content of 15 mass% or more.

Next, as an optional step (C), the obtained first volatile fraction (volatilization section B) is further subjected to thin-film distillation to obtain a second volatile fraction (volatilization section C). In this step, for example, the thin film distillation is preferably carried out at a hot solvent temperature of 90 to 180 ℃ and a pressure of 0.00001 to 0.01 bar, preferably 140 to 160 ℃ and a pressure of 0.002 to 0.008 bar. In this case, in the composition of the present invention, 50 to 95% by mass, preferably 60 to 95% by mass, and more preferably 60 to 90% by mass of the first volatile fraction B is recovered as the second volatile fraction (volatilization unit C), and preferably 5 to 50% by mass, preferably 5 to 40% by mass, and more preferably 10 to 40% by mass is recovered as the non-volatile unit C. The second volatile fraction (volatile portion C) may BE caryophyllene BE, geranylene D and melaleuca alternifolia in a total mass of 15 mass% or more. Here, the second volatile fraction obtained in step (c) can impart a more refreshing and rich mint feeling as a taste improver for the menthol-containing composition and the carvone-containing composition, while imparting a more refreshing feeling (ボリューム feeling) and a more refreshing feeling.

In the production method of the present invention, the so-called bottom-remaining volatile fraction, which is not required in the essential oil at present, can be extracted in a refined manner by repeating distillation in stages, and the obtained first volatile fraction and/or second volatile fraction can be added to the essential oil for obtaining the volatile fraction a in an appropriate amount, for example, whereby a composition which does not exist in the past and gives a delicate minty feeling can be constructed.

In the production method of the present invention, it is preferable that the distillation is performed by a precision distillation method in the step (a), and the distillation is performed by a thin film distillation method in the steps (b) and (c).

In addition, caryophyllene BE, senecine D, and melaleuca alternifolia alcohol may BE enhanced in the first volatile fraction and/or the second volatile fraction to obtain the composition of the present invention.

The first volatile fraction and/or the second volatile fraction may be further concentrated by a known method such as resin treatment or membrane treatment, or nonvolatile components such as chlorophyll may be further removed, and the extract or the concentrate may be dried by a method such as lyophilization to be powdered.

As in the step (a) of the present invention, a step of further distilling an oil derived from a plant of the genus mentha of the family labiatae such as peppermint oil has not been conventionally performed by those skilled in the art. Further, the completion of the present invention itself is not conceivable to those skilled in the art from the viewpoint of the distillation residue thus obtained. Further, according to the present invention, the distillation residue which has been conventionally discarded can be effectively utilized.

The composition of the present invention may contain a solvent such as ethanol, propylene glycol, glycerin, an edible oil or fat, and MCT.

The composition of the present invention thus obtained can be suitably contained in a liquid flavor composition, a solid flavor composition, or the like as described later, and can be added to a food or drink, a perfume cosmetic, or an oral care product in any form depending on the purpose of use. The composition including the added food or the like is in any form (for example, liquid or solid form), and the amount is determined by mass% or parts by mass in the present invention.

< perfume composition >

The present invention also provides a perfume composition comprising a volatile fraction obtained from the distillation residue of the oil derived from a plant of the genus mentha of the family lamiaceae of the present invention described above, a composition comprising the volatile fraction, and a composition comprising menthol, and a perfume composition comprising the volatile fraction and a composition comprising carvone. The concentration of the volatile fraction derived from the oil derived from a plant of the genus mentha of the family labiatae in the perfume composition can be appropriately determined depending on the property of the perfume composition to be treated and the desired effect. In addition, l-menthol and/or l-carvone can be added to the composition of the present invention to enhance the fragrance.

The perfume composition of the present invention may comprise various compounding agents and/or additives. The compounding agent and the additive to be mixed are not particularly limited, and examples thereof include an antioxidant, a known preservative, an antibacterial agent, and a pH adjuster. The compounding agents and additives can be used in combination of 2 or more kinds in any combination.

More specifically, examples of the antioxidant include, in addition to butylhydroxytoluene, butylhydroxyanisole, citric acid, glutathione, selenium, lycopene, vitamin a, vitamin E, vitamin C, and the like, pyrrolopyrrole derivatives, free radical scavengers (free radial scavengers) obtained from extracts from various plants, superoxide dismutase (superoxide dismutase), glutathione peroxidase, and other enzymes having antioxidant properties.

Examples of the preservative and the antibacterial agent include benzoic acid, sodium benzoate, isopropyl p-hydroxybenzoate, isobutyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, methyl p-hydroxybenzoate, butyl p-hydroxybenzoate, propyl p-hydroxybenzoate, sodium sulfite, potassium metabisulfite, sorbic acid, potassium sorbate, sodium dehydroacetate, juniperberry alcohol (Thujaplicin), an udo extract, a storax extract, an artemisia draconis extract, an oolong tea extract, an apple polyphenol extract, an enzymatically decomposed coix seed extract, tea catechins, apple polyphenols, a pectin decomposition product, chitosan, lysozyme, and epsilon-polylysine.

Examples of the pH adjuster include adipic acid, citric acid, trisodium citrate, glucono delta lactone, gluconic acid, potassium gluconate, sodium gluconate, DL-tartaric acid, L-tartaric acid, potassium hydrogen DL-tartrate, potassium hydrogen L-tartrate, sodium L-tartrate, potassium carbonate (anhydrous), sodium hydrogen carbonate, sodium carbonate, carbon dioxide, lactic acid, sodium lactate, glacial acetic acid, disodium dihydrogen pyrophosphate, fumaric acid, monosodium fumarate, DL-malic acid, sodium DL-malate, phosphoric acid, dipotassium hydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, and sodium dihydrogen phosphate.

< product >

The invention further provides drink and food, medicines, perfume cosmetics and oral care products containing the spice composition. The concentration of the flavor composition in food and drink products, pharmaceuticals, perfume cosmetics, and oral care products can be appropriately determined by those skilled in the art according to the properties of the target product and the desired effect.

The food and drink products, the pharmaceutical products, the perfume cosmetics, and the oral care products to which the present invention is directed are not particularly limited, but can be directed to a wide range including liquid, solid, semisolid, and fluid products as long as the advantages of freshness and refreshing property derived from plants of the genus mentha of the family lamiaceae to which the present invention is directed are obtained and the advantage of a aromatic flavor with a rich refreshing feeling is added.

Although not intentionally limited, examples of the food and drink include fruit juice, fruit juice beverages, non-fruit juice beverages, vegetable beverages, carbonated beverages, sports beverages, coffee beverages, tea, black tea, oolong tea, mineral beverages, yogurt beverages, milk beverages, lactic acid bacteria beverages, nutritional beverages, alcoholic beverages, non-alcoholic beverages, liquid products such as catechins and seasonings, solid products such as candies, chewing gums, tablets, soft candies, jellies, chocolates, baked fruits such as biscuits and cakes, marshmallows, bread, ice cream, sherbet, ham, sausages, desserts, oils such as powdered sauce, fats such as artificial butter, solid products such as edible sheet food, curry, simmered vegetables, beef onion rice, chili oil, seasonings, salad dressings, fresh cream, fruit jam, flowable food, and semisolid flowable products. The pharmaceutical and perfume cosmetic is not particularly limited as long as it is used in combination with the perfume composition. In addition, as oral care products, dentifrice, liquid toothpaste, mouth wash, oral spray, and the like can be given.

The drink food, the pharmaceutical, the perfume cosmetic and the oral care product to be subjected to the present invention may include various compounding agents and additives commonly used in drink foods, pharmaceutical, perfume cosmetics or oral care products. Examples of the additives include sweeteners, sour agents, extenders, coloring agents, emulsifiers, functional substances, conventional flavor improvers, milk components, nitrogen-containing compounds such as amino acids and peptides, various flavor materials, surfactants, abrasives, binders, humectants, and other solvents, in addition to the above-mentioned antioxidants, known preservatives, antimicrobial agents, and pH adjusters. These compounding agents and additives may be used in combination of 2 or more.

More specifically, examples of the sweetener include granulated sugar, fructose, lactose, glucose, palatinose, maltose, trehalose, sorbitol, erythritol, maltitol, reduced palatinose, xylitol, lactitol maltose, oligosaccharide, aspartame, sucralose, acesulfame potassium, saccharin sodium, tangerines extract, stevioside, neotame, alitame, thaumatin, neohesperidin dihydrochalcone, p-methoxycinnamaldehyde, perillartine, and licorice.

Examples of the sour seasoning include acetic acid, lactic acid, and citric acid.

Examples of the extender include saccharides, polysaccharides, processed starch, casein, gelatin, carboxymethyl cellulose, lecithin, and the like.

Examples of the pigment include natural pigments, organic synthetic pigments, and the like, and specifically include hibiscus pigment, black berry pigment, plum pigment, laver pigment, dewberry pigment, grape juice pigment, blackberry pigment, blueberry pigment, mulberry pigment, mo Leiluo cherry pigment, red currant pigment, myricetin, colored pepper powder, malt extract, rutin, flavonoid, red cabbage pigment, red radish, adzuki bean pigment, ginger yellow, olive tea, blueberry pigment, chlorella powder, saffron pigment, perilla pigment, strawberry pigment, chicory pigment, hickory pigment, red rice pigment, safflower pigment, purple sweet potato pigment, lac red pigment, spirulina pigment, onion pigment, tamarind pigment, capsicum pigment, caramel pigment, viola pigment, rosewood pigment, krill pigment, orange pigment, carrot carotenoid, blue No. 1, yellow No. 4, green No. 3, and the like.

Examples of the emulsifier include fatty acid monoglycerides, fatty acid diglycerides, fatty acid triglycerides, propylene glycol fatty acid esters, sucrose fatty acid esters, polyglycerol fatty acid esters, lecithin, enzymatically treated lecithin, starch, processed starch, dextrin, sorbitan fatty acid esters, quillaja extract, gum arabic, gum tragacanth, guar gum, gum karaya, xanthan gum, pectin, alginic acid and salts thereof, carrageenan, gelatin, casein, and the like.

<xnotran> , , (DHA), (EPA), DHA / EPA , , γ - , α - , , , , , , , , , 5363 zxft 5363 , , A, D, E, F, K, Q10, α , , γ - , , , , , , , , , , , (CCM) , , , , , , , , 1 , , , , , , ε , dl- , α - , , , , , , , , , , , , , , , , , , , , , , </xnotran> Benzethonium chloride, cetylpyridinium chloride, trichlorocarbalide, zinc citrate, and cortex Phellodendri extract.

Examples of the milk component include raw milk, cow milk, whole milk powder, skim milk powder, fresh cream, milk proteins such as casein and whey, components derived from milk such as goat and sheep, and decomposed products thereof.

Examples of known flavor improving agents include sucralose, cyclodextrin, theanine, hesperidin glycoside, and sugar cane extract.

Examples of the various flavor materials include natural flavors, natural essential oils, and various synthetic flavors. These flavors are not particularly limited as long as they can be used in foods and drinks, pharmaceuticals, perfume cosmetics, and oral care products, and examples thereof include esters, aldehydes, (thio) ethers, alcohols, ketones, lactones, carvonic acid, aliphatic hydrocarbons, nitrogen-containing heterocyclic compounds, sulfur-containing heterocyclic compounds, amino groups, thiols, phenols, and essential oils.

<xnotran> , , , , , , , α - , , , , , , , , , , , , , , , , , γ - , , 2- -3528 zxft 3528- 2- -3835 zxft 3835- , , , 2- , , 2- -3- , 2- -5- ,5- -2- , , , , , , , , , , , , , , , , , , , , , , , , , , , l- , , , , 3924 zxft 3924- -5- , , , , , 3534 zxft 3534- , , 5248 zxft 5248- , 5362 zxft 5362- , 5725 zxft 5725- , 3432 zxft 3432- , </xnotran> Gingerol, cinnamyl alcohol, cinnamaldehyde, chrysanthenol, thymol, decanal, decanol, ethyl decanoate, 5,6,7,8-tetrahydroquinoxaline, 2,3,5,6-tetramethylpyrazine, terpineol, 2,3,5-trimethylpyrazine, γ -nonalactone, vanillyl butyl ether, vanillin, p-methylacetophenone, nonanal, hydroxycitronellal dimethyl acetal, pinene, piperidine, piperine, piperonal pyrazine, pyrrolidine, isoamyl phenylacetate, isobutyl phenylacetate, ethyl phenylacetate, 2- (3-phenylpropyl) pyridine, phenethyl ester amine, phenoxyethyl isobutyl ester, fenchytone, butanol, butyl amine, butyl aldehyde, furfural and derivatives thereof, pulegone, propanol, pentone aldehyde, propionic acid, isoamyl propionate, ethyl propionate, benzyl propionate, hexanoic acid, allyl hexanoate, allyl hexanoate, ethyl hexanoate, benzyl acetate, N-ethyl hexanoate, benzyl acetate, and benzyl acetate ethyl hexanoate, hexanal, hexenol, ethyl heptanoate, perillaldehyde, benzyl ester alcohol, benzaldehyde, 2-pentanol, 1-penten-3-ol, d-borneol, maltol, anthranilate, methyl N-methyl anthranilate, methyl jasmonate, 5-methylquinoxaline, 6-methylquinoline, 5-methyl-6,7-dihydro-5H-cyclopentapyrazine, methyl β -naphthalenone, 2-methylpyrazine, 2-methylbutanol, 3-methyl-2-butanol, 2-methylbutylaldehyde, 3-methyl-2-butenal, 3-methyl-2-butenol, menthol isomers such as menthol acetate and l-menthol, butyric acid, isoamyl butyrate, ethyl butyrate, cyclohexyl butyrate, butyl butyrate, gamma lactone having 4 to 12 carbon atoms, γ and delta lactone, linalool acetate, linalool, limonene, and the like.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

Examples

1. Analysis of aroma Components

The assignment of the main peak was analyzed by GC-MS, and the concentration of each aroma component was calculated by subjecting each parameter to GC-FID analysis.

2. Evaluation of Functionality

The effects expected from the evaluation samples (sensory feeling, sweetness and natural feeling) and the effect to be eliminated (oil and fat odor) were functionally evaluated by 10 panelists. The panelists performed so as to include the evaluation samples in their mouths, and the scores of the control groups were adjusted to 5 points based on the evaluation criteria shown in table 1 for the expected effects. In addition, the score of the control group was adjusted to 1 point based on the evaluation criteria shown in table 2 for the effect to be excluded. The evaluation samples were evaluated for 3 items of component taste, sweetness and natural taste for 1 to 9 points, and for oil and fat odor for 1 to 5 points, and the evaluation score was expressed by the average value ± standard deviation from the 1 st position of the decimal point of the average value to the fourth and fifth positions. The standard deviation rounds the 2 nd bit after the decimal point.

[ Table 1]

[ Table 2]

Odor of oil and fat	Score of
		High strength	5
Is slightly stronger	4
		Weak (weak)	3
Is very weak	2
		Has no feeling of feeling	1

Example 1 and comparative examples 1 to 3

500kg of peppermint oil (manufactured by ADM) was subjected to precision distillation under reduced pressure at a temperature of 80 to 140 ℃ and a pressure of 0.01 to 0.02 bar to obtain a volatile fraction A and a nonvolatile fraction A of 28.9 kg.

The nonvolatile part A was subjected to thin film distillation to obtain a volatile part B and a nonvolatile part B of 23.1 kg. The conditions for the thin film distillation were a hot solvent temperature of 150 ℃ and a pressure of 0.0040 bar.

The fraction in the volatilization part B was defined as the composition of example 1-1, and the volatilization part A, non-volatilization part A and non-volatilization part B were defined as the compositions of comparative examples 1, 2 and 3, respectively. The volatile fraction B was prepared from another batch of peppermint oil by the same method to give examples 1-2 and 1-3 (each by 3 times the same method).

[ example 2]

The volatile fraction B obtained in the above was further subjected to thin film distillation to obtain 4.6kg of a volatile fraction C. The conditions for the thin film distillation were a hot solvent temperature of 150 ℃ and a pressure of 0.0040 bar.

The volatile fraction C was the composition of example 2-1, example 2-2, and example 2-3 (each was carried out by the same method 3 times).

The total mass (C + G + V) of caryophyllene BE (expressed as C), germacrene D (expressed as G) and melaleuca alternifolia (expressed as V) contained in examples 1-1 to 1-3, examples 2-1 to 2-3 and comparative examples 1, 2 and the respective contents of C, G, V are shown in mass% in table 3.

[ Table 3]

(test example 1)

Sensory evaluation toothpaste for imparting flavor to peppermint oil-based flavor

A control composition was prepared which consisted of 20 mass% of peppermint oil (manufactured by ADM) having a menthol content of 42 mass% and 80 mass% of MCT (manufactured by riqing oiritomo). Fragrance samples were prepared by adding 0.1 mass% of each of the compositions of examples and comparative examples to 99.9 mass% of the control composition. Then, 10g of flavor sample was added to the base toothpaste (composition: table 4), and the resulting evaluation sample was adjusted to contain 1 mass% of the flavor sample, thereby performing a sensory evaluation. The evaluation results are shown in table 5.

[ Table 4]

(ingredient)	(compounding amount g)
		Calcium carbonate	400.0
Silicic anhydride	16.5
		Sorbitol solution (70%)	240.0
Sodium lauryl sulfate	13.0
		Sodium carboxymethylcellulose	12.5
Carrageenan	3.0
		Sodium benzoate	4.0
Saccharin sodium salt	1.5
		Purified water	259.5
Propylene Glycol (PG)	40.0
		Total up to	990

[ Table 5]

(test example 2) evaluation of Funginess of toothpaste containing l-menthol-based flavor

A control composition was prepared which consisted of l-menthol (manufactured by Kagaku Kogyo Co., ltd.) in an amount of 20 mass% and MCT (manufactured by Riqing Oillio Co., ltd.) in an amount of 80 mass%. A fragrance sample was prepared by adding 0.1% by mass of the composition of example 2-1 to 99.9% by mass of the control composition. Then, by adding 10g of flavor sample to the base toothpaste (composition: table 4), the sensory evaluation was performed using an evaluation sample adjusted so as to contain a flavor sample at a concentration of 1 mass%. The evaluation results are shown in table 6.

[ Table 6]

(test example 3) evaluation of functionality toothpaste prepared by perfuming a fragrance based on l-carvone

A control composition was prepared which consisted of 20 mass% of l-carvone (WANXIANG INTERNATIONAL FLAVORS & FRAGRANCES) and 80 mass% of MCT (Riqing Oligomo). A fragrance sample was prepared by adding 0.1% by mass of the composition of example 2-1 to 99.9% by mass of the control composition. Furthermore, a sensory evaluation was performed using an evaluation sample prepared by adding 10g of a flavor sample to a base toothpaste (composition: table 4) so as to contain the flavor sample at a concentration of 1 mass%. The evaluation results are shown in table 7.

[ Table 7]

Claims

1. A composition is derived from a plant of the genus Mentha of the family Labiatae, and contains caryophyllene BE, germacrene D and melaleuca alternifolia alcohol in an amount of 15% by mass or more based on the total amount of the composition.

2. A composition comprising caryophyllene BE, senecine D and melaleuca alternifolia alcohol which are volatile fractions obtained by distilling oil derived from plants belonging to the genus Mentha of the family Labiatae under reduced pressure, wherein the total mass of caryophyllene BE, senecine D and melaleuca alternifolia alcohol content is 15% by mass or more relative to the total mass of the composition.

3. The composition as claimed in claim 1 or 2, wherein the plant of the genus Mentha of the family Lamiaceae is selected from Mentha piperita, mentha viridissima and Mentha arvensis.

4. The composition according to any one of claims 1 to 3, which is a composition for improving the taste of a menthol-containing composition, and is added as follows:

5. The composition according to any one of claims 1 to 3, which is a composition for improving the taste of a composition containing carvone, and is added as follows:

6. A perfume composition comprising the composition of any one of claims 1 to 5.

7. A beverage food, a pharmaceutical, a perfume cosmetic or an oral care product comprising the flavor composition of claim 6.

8. A method for producing a composition containing caryophyllene BE, geranylene D and melaleuca alternifolia alcohol, comprising the following steps (a) and (b):

(a) A step of distilling oil derived from a plant of the genus Mentha of the family Labiatae under reduced pressure to obtain a distillation residue of 3 to 25 mass% of the total amount of oil derived from a plant of the genus Mentha of the family Labiatae, and

the composition contains a first volatile fraction, may contain a second volatile fraction, and the total mass of the contents of caryophyllene BE, germacrene D and melaleuca alternifolia alcohol is 15 mass% or more with respect to the total amount of the composition.

9. A composition comprising a volatile fraction obtained by subjecting an oil derived from a plant belonging to the genus Mentha of the family Labiatae to vacuum distillation at a pressure of 0.00001 to 0.05 bar and a temperature of 40 to 250 ℃ to obtain a distillation residue in an amount of 3 to 25 mass% based on the total amount of the oil derived from the plant belonging to the genus Mentha of the family Labiatae, subjecting the distillation residue to thin film distillation, the volatile fraction being 5 to 50 mass% based on the total amount of the distillation residue,