WO2016148151A1 - 柑橘の果皮精油を含む液状組成物 - Google Patents
柑橘の果皮精油を含む液状組成物 Download PDFInfo
- Publication number
- WO2016148151A1 WO2016148151A1 PCT/JP2016/058184 JP2016058184W WO2016148151A1 WO 2016148151 A1 WO2016148151 A1 WO 2016148151A1 JP 2016058184 W JP2016058184 W JP 2016058184W WO 2016148151 A1 WO2016148151 A1 WO 2016148151A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rutin
- limonin
- essential oil
- liquid composition
- acidity
- Prior art date
Links
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- 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
- A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
- A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/15—Flavour affecting agent
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
- A23V2250/2116—Flavonoids, isoflavones
- A23V2250/2117—Rutin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2300/00—Processes
- A23V2300/14—Extraction
Definitions
- the present invention relates to a liquid composition containing an essential oil (fruit peel essential oil) obtained from citrus peel. More specifically, the present invention relates to a liquid composition that contains pericarp essential oil and a specific concentration ratio of limonin and rutin, has a low acidity and little bitterness, and can be blended in a beverage.
- Citrus fruit juice obtained by squeezing citrus fruit may have problems such as bitterness, acidity, astringency, and off-flavor. Moderate bitterness and sourness are accepted by consumers as reminiscent of natural fruits, but excessive bitterness and sourness can make consumers uncomfortable. Therefore, a method for reducing the bitterness and acidity of citrus juice by adding hesperidin glycoside (Patent Document 1), adding citric acid and alkali metal citrate or condensed phosphate, Methods for suppressing bitterness have been proposed (Patent Documents 2 and 3).
- Patent Document 4 a method of adjusting the flavor of citrus fruit juice having a step of adjusting the concentration of limonin and polymethoxylated flavone to a level below the taste threshold and adjusting the sugar acid ratio of the fruit juice has been proposed (Patent Document 4). ).
- Non-Patent Documents 1 and 2 the method of squeezing so that the extract of these parts may not be contained in fruit juice is also developed.
- JP 11-318379 A JP-A-60-246325 JP 2013-33 A Special table 2011-500028 gazette
- An object of the present invention is to provide a liquid composition containing a skin essential oil that has a natural fresh fragrance derived from a natural citrus fruit and has little stimulating bitterness and can be blended in a beverage.
- the present inventors have found that the liquid composition obtained by reducing rutin from the citrus fruit peel and then crushing the peel in water does not contain fruit juice. It has been found that it has a fragrance peculiar to fruit peel essential oil.
- a liquid composition in which the concentration of rutin with respect to acidity is limited to a certain value has a good aroma close to natural fruit, with little bitterness and sourness, despite containing a specific amount of limonin.
- the present invention was completed by finding that it is suitable for blending with beverages.
- the liquid composition is ⁇ Contains essential oil, limonin and rutin, -The essential oil content of the skin is 0.2 to 3.5% by volume relative to the total amount of the composition,
- the concentration of limonin relative to acidity is 10 to 300 mg / kg / Acid,
- the concentration of rutin relative to acidity is 10-50 mg / kg / Acid,
- the mass ratio of rutin to limonin (rutin / limonin) is 1 or less, -Acidity is 2.0% or less.
- the above-mentioned peel essential oil, limonin, and rutin may be derived from citrus fruits.
- the liquid composition described above can be used as an aroma juice by adding it to a beverage, but its acidity is overwhelmingly lower than that of a conventional juice (including a communal juice).
- the unit “mg / kg / Acid” relating to the concentrations of limonin and rutin is obtained by dividing the concentration of limonin or rutin (mg / kg) in the composition by the acidity of the composition.
- the acidity is expressed as a percentage in terms of citric acid by measuring the content of the organic acid in the liquid by neutralization titration with sodium hydroxide.
- the inventors of the present invention have found that a strong and intense bitterness of citrus fruits is present especially in the supersurface layer of the fruit skin (within 1 mm, particularly within 0.7 mm from the outer surface).
- the super surface layer of the pericarp was peeled off and removed to such an extent that the oil vesicles in the pericarp were not broken, thereby successfully removing the bitter taste of the pericarp while retaining the aroma components of the citrus pericarp.
- the concentration of limonin which is known as a bitter component, hardly changed, whereas the concentration of rutin decreased significantly. I found.
- the bitter taste of limonin is enhanced under high acidity.
- the strong bitterness of limonin can be further suppressed by adjusting the acidity to 2.0% or less.
- a liquid composition having a specific amount of peel essential oil and a specific rutin / limonin ratio and having an acidity of 2.0% or less is, for example, thick enough not to break the oily vesicles as described later. It can be manufactured using the peel of citrus fruit (ie, citrus peel with reduced rutin) and a solvent such as water, and if the rutin concentration of the peel is not so high, the super-surface part is removed. Alternatively, a liquid composition having a specific rutin / limonin ratio can be obtained by adjusting the mixing ratio of water and pericarp when mixing.
- FIG. 2 shows a partially enlarged view of FIG. 1.
- the super-surface layer portion 1 is removed. It is an external appearance photograph of the citrus fruit before and behind the removal of a super surface layer part. In each photo, the left is before removal and the right is after removal. The top photo is lemon, the second photo is lime, the third photo is grapefruit, and the bottom photo is orange.
- the composition of the present invention contains peel essential oil in an amount of 0.2 to 3.5% by volume based on the total amount of the composition.
- the peel essential oil is a group of compounds having aromaticity mainly collected from the peel of citrus fruits.
- Fruit essential oil is mainly composed of terpene compounds such as monoterpene and sesquiterpene, and aromatic compounds, and is different from fats and oils mainly composed of glycerin fatty acid ester. Examples of methods for collecting essential oils from plants include steam distillation methods, pressing methods, solvent extraction methods, ambulage methods, maceration methods, supercritical extraction methods, and the like, and the pericarp essential oil used in the present invention is any known collection method. However, it is preferable to use an essential oil component obtained by a pressing method.
- the expression method in this specification refers to a method in which physical force is applied to the pericarp, and essential oil is obtained from the oleifer cells in the colored part of the pericarp.
- a pressing method for example, a method of mechanically damaging the pericarp to break oil vesicles and taking out essential oil is known (Florida Citrus Oils, Kesterson, et al., Technical Bulletin 749, December 1971, pp15-20) . Further, as described in the method described later, a method of emulsifying a skin containing essential oil while being crushed in water is also included in the pressing method. Citrus peel has dark flavedes and white fibrous albedo.
- flavedes contain many oil vesicles that contain a lot of essential oil (see Fig. 1) (Encyclopedia of Fruits, Asakura Shoten) , P.198 (2008)).
- it can be set as the liquid composition containing a pericarp essential oil by extract
- the pericarp essential oil thus obtained is advantageous in that it is not easily affected by heat and oxygen and has little deterioration of aroma components.
- skin essential oil is obtained by a conventional method such as cold press method, the essential oil is once taken out from the oil vesicle, so the aroma component in the essential oil may be directly affected by oxygen and deteriorate. is there.
- the citrus fruit used to obtain the skin essential oil may be any of the genus Citrus or Fortunella generally used for food, but the citrus genus is particularly preferable because of the effect of the present invention. preferable.
- the citrus genus includes perfumed citrus fruits (lemon, lime, yuzu, kabosu, daidai, sudachi, shiquasar, citron, bushcan, etc.), oranges (valencia orange, navel orange, blood orange, etc.), grapefruits (Marsh, Ruby, etc.), Citrus (Natsumikan, Hassaku, Hyuga Natsu, Sweety, Dekopon, etc.), Tangor (Iyokan, Tankan, Kiyomi, Harumi, etc.), Tan Zero (Seminor, Mineola, etc.), Buntan (Buntan, Bumpeiyu) And the like, and mandarin oranges (mandarin orange, citrus orange, citrus orange, ponkan, tachibana, etc.).
- examples of the genus Kumquat include Nympho kumquat, Marumi kumquat, and Nagami kumquat.
- fruits that have a strong sour or bitter taste in the fruit juice itself and cannot contain a large amount of the fruit juice itself in a beverage are preferred in the present invention.
- examples of such citrus fruits include those having a fruit juice acidity of 1.5% or more, preferably 2.0% or more, more preferably 3.0% or more, and even more preferably 4.0% or more. it can.
- citrus fruits having a very small amount of sugar with respect to acidity are also preferred for the present invention because of their strong acidity.
- Examples of the citrus fruit having a very small amount of sugar with respect to the acidity include those having a sugar acid ratio of 10 or less, preferably 8 or less, more preferably 5 or less, and particularly preferably 3 or less.
- the acidity referred to in the present invention refers to the content of organic acids such as citric acid and malic acid measured by a neutralization titration method using sodium hydroxide and expressed as% in terms of citric acid.
- the sugar acid ratio is a value obtained by dividing the value (Brix) expressed in% when measured with a refractometer for sugar by the acidity.
- Table 1 shows the sugar content, acidity, and sugar acid ratio of typical citrus fruits. Examples of fruits suitable for the present invention include lemon, lime, sudachi, kabosu), seaquaser, yuzu, and the like.
- the concentration of the fruit essential oil in the liquid composition is 0.2 to 3.5% by volume with respect to the total amount of the composition. Preferably 0.3 to 3.0% by volume, more preferably 0.4 to 2.5% by volume, still more preferably 0.4 to 2.0% by volume, particularly preferably 0.4 to 1.5% by volume. It is.
- the concentration of the peel essential oil in the composition can be measured with a distillation system (Essential Oil Testing Apparatus) using an essential oil quantification device as described in Examples below.
- the composition of the present invention comprises limonin.
- Limonin is known to exist in the fruit as a glycoside form (limonin glucoside) (formula 1) or as a form in which sugar is removed from the glycoside (limonoate A-ring lactone) (formula 2).
- Limonin glucoside and limonoate A-ring lactone do not exhibit a bitter taste.
- the limonate A-ring lactone is closed under the acidity of the fruit juice to form limonin (7,16-dioxo-7,16-dideoxylimondiol, C 26 H 30 O 8 ) (formula 3). It is known to become a strong bitter taste.
- the concentration of limonin in the composition of the present invention is preferably 10 to 300 mg / kg / Acid, more preferably 15 to 200 mg / kg / Acid, and still more preferably 20 to 150 mg / kg / Acid.
- the unit “mg / kg / Acid” is obtained by dividing the concentration of limonin (mg / kg) in the composition by the acidity of the composition.
- the acidity is a value expressed in% in terms of citric acid by measuring the content of the organic acid in the composition by neutralization titration with sodium hydroxide.
- the concentration of limonin in the composition means the concentration of the above formula 3.
- the concentration of limonin in the liquid composition of the present invention can be adjusted by adding commercially available limonin to the composition. Moreover, as described in the method to be described later, it can also be obtained by emulsifying a skin or flavedo containing a fruit essential oil while crushing in water and extracting limonin derived from fruits into a liquid composition.
- the concentration of limonin in the liquid composition can be measured using LC-MS, as described in Examples below.
- the limonin contained in the liquid composition of the present invention is not limited to this, but is preferably derived from citrus fruits. It is considered that a composition close to the flavor of natural citrus fruit can be obtained by using a limonin derived from citrus fruit and combining with essential oil.
- the composition of the present invention comprises rutin.
- the concentration of rutin in the composition of the present invention is 10 to 50 mg / kg / Acid, preferably 15 to 45 mg / kg / Acid.
- the mass ratio of rutin to limonin is preferably 1 or less, more preferably 0.8 or less, and even more preferably 0.6 or less.
- strong bitterness means physical irritation due to convergence of the tongue mucosa, and represents excessive bitterness and unpleasant bitterness, which is different from the moderate bitterness allowed as a chemical irritation. .
- a small amount of a bitter substance below a threshold value makes the taste of foods and dishes complex and deep.
- bitterness has a contrasting effect with sweetness.
- the bitter taste of limonin present in the peels of citrus fruits is an excessive bitterness that is irritating and is often perceived as unpleasant.
- by suppressing the ratio of rutin to limonin to 1 or less “strong bitterness” can be selectively reduced.
- Rutin (quercetin-3-glucoside, molecular formula C 27 H 30 O 16 ) is a kind of flavone glycoside and is known to be contained in buckwheat (Fagopyrum exculentum), asparagus, etc., and citrus fruit It is also known to be contained in the pericarp.
- the rutin contained in the liquid composition of the present invention is not limited to this, but is preferably derived from citrus fruits.
- the concentration of rutin can be adjusted by adding a certain amount of commercially available rutin to the composition containing peel essential oil and limonin or removing rutin from the composition.
- the concentration of rutin can be reduced by removing (with a thickness that does not damage the oil vesicles).
- rutin is contained in the peels of citrus fruits, it has been found for the first time by the present inventors that a large amount of rutin is present especially in the vicinity of the outside of the peels.
- the concentration of rutin in the liquid composition can be measured using LC-MS as described in Examples below.
- Citrus fruit peel essential oil is easily altered and has a chemical odor when its acidity is high.
- the composition of the present invention is a natural, fresh and less aroma composition by keeping the acidity low.
- the acidity of the composition of the present invention is 2.0% or less, preferably 0.1 to 1.5%, more preferably 0.2 to 1.2%, still more preferably 0.2. ⁇ 1.0%.
- the strong bitterness of the composition can be further effectively suppressed by adjusting the acidity of the composition to the above range.
- the “acidity” in the present specification is a measurement of the content of organic acids such as citric acid and malic acid by the neutralization titration method with sodium hydroxide, and the value is converted to the citric acid content. And expressed in mass%.
- Combined fruit juice of high acidity fruit has a problem that if the beverage is blended in a large amount, the beverage becomes sour and difficult to drink, so there is a problem that it cannot be blended in a large amount in the beverage, but the low acidity liquid composition of the present invention Has not only the above-mentioned advantage that the limonin's strong bitterness is hardly felt, but also has the advantage that the beverage can contain a large amount of aroma components of fruit essential oil in the beverage.
- the liquid composition having a specific amount of fruit essential oil of the present invention and a rutin / limonin ratio of 1 or less and an acidity of 2.0% or less is, for example, thick enough not to break the oil vesicles as described later.
- the citrus fruit peel from which the super-surface layer portion is removed ie, citrus peel with reduced rutin
- a solvent such as water
- the composition of the present invention is liquid at normal temperature and pressure. It is preferable to use water as the main solvent.
- the pH is preferably less than 5. A low pH is advantageous for suppressing spoilage bacteria.
- the liquid composition of the present invention for example, as will be described later, is obtained by removing fruit essential oil from the oil follicles by emulsifying the skin or flavedo having oil vesicles containing essential oils while crushing in water. It can also be produced by extracting limonin into water. In this case, a liquid composition can be manufactured without including components other than fruit and water, and becomes a flavor liquid not using food additives.
- non-addition of additives means that those described in the “list of items in the existing additive list” prescribed in the Japanese Food Sanitation Law are not added “from the outside”.
- the liquid composition of the present invention can be blended with food and drink for flavoring.
- a beverage when blended in a beverage, it can be blended at a concentration of 0.1 to 15 mass%, preferably 0.2 to 10 mass%, depending on the target flavor.
- the liquid composition of the present invention is an aqueous composition that has a low acidity, or a low acidity and sugar content, and contains a relatively large amount of essential oil in the skin.
- an advantage that can be made.
- the aroma of the fruit can be sufficiently reproduced in the beverage. It can also be used to impart fruit flavor to tea beverages such as black tea.
- the kind of beverage is not particularly limited, and can be used for various beverages such as alcoholic beverages, beverages not containing alcohol, carbonated beverages, fruit juice-containing beverages, and tea-based beverages.
- the liquid composition does not contain alcohol (ethanol)
- it can be suitably used for flavoring beverages that do not contain alcohol.
- it can be suitably used for flavoring low fruit juice beverages (non-alcoholic beverages) having a fruit juice content of about 1 to 30% by mass, preferably 1 to 20% by mass, more preferably 1 to 10% by mass.
- Beverages that reproduce the aroma can be produced.
- a beverage without a synthetic additive such as a synthetic fragrance or a synthetic surfactant can also be produced.
- the liquid composition of the present invention can be produced by adjusting the amount and acidity of pericarp essential oil, limonin and rutin. Moreover, although not limited to this, it can manufacture using only a fruit and water by the method as described below. A liquid composition composed only of fruit-derived components and water exhibits a fragrance closer to that of natural fruits and is preferable.
- the super-surface layer part of the citrus fruit peel is thinly removed with a thickness that does not break the oil vesicles in the flavedo.
- the present inventors have found that rutin is present in a large amount in the superficial layer, particularly in the pericarp, that rutin enhances the strong bitterness of limonin in the pericarp, and removing the supersurface portion of the pericarp. It was found that the strong bitterness of the pericarp can be reduced by selectively reducing the concentration of.
- the super surface layer portion is a portion 1 in FIG.
- the super-surface layer portion is usually within about 1 mm from the outer surface of the fruit skin, preferably within 0.9 mm, more preferably within 0.8 mm, The thickness is preferably within 0.7 mm, and the thickness is such that most of the oil vesicles remain without being destroyed.
- the aroma components contained in the essential oil (peel oil) in the oil vesicle are known to be susceptible to oxidative degradation, but the essential oil is in direct contact with the atmosphere (oxygen) by not destroying the oil vesicle as much as possible. Can avoid the deterioration of essential oil.
- the number of oil vesicles exceeding 50% in number remain without being destroyed, more preferably 70% or more, and still more preferably 90% or more. Oil vesicles can be confirmed with an optical microscope and also with the naked eye.
- the super-surface layer part of the skin is preferably removed in an area of 50% or more, more preferably 80% or more, and further preferably 90% or more, based on the entire external area of the skin. Whether or not the super surface layer has been removed can also be confirmed with the naked eye.
- the color of the outer surface of the skin changes slightly. For example, a lemon or orange has a slightly reddish color, a whited, yellowish color slightly increased, or a slightly greenish color (see FIG. 3).
- a knife or household peeler when removing the superficial layer of the fruit skin, because it may damage the oil vesicles.
- a rotary drum peeler used for root vegetables such as potato.
- the rotary drum-type peeling machine has a pair of cylindrical rotary drums that rotate upward with respect to each other.
- a peeler that does not have protrusions such as blades and claws on the rotating drum.
- a rotating drum having protrusions such as blades and claws is used to peel citrus fruits, the oil vesicles of the skin may be destroyed.
- a drum having a number of holes perforated on its surface can be suitably used.
- the pericarp is collected from the fruit using a conventional method.
- the pericarp is divided into a dark colored flavedo part containing oil vesicles and a white fibrous albedo part, but the albedo part of the pericarp does not contain oil vesicles, so there are fewer aroma components compared to the flavedo part, and the fruit Some have a bitter taste. Therefore, when collecting the skin, most of the albedo portion may be removed from the skin and the flaved portion may be collected. At this time, a small amount of the albedo portion may be mixed in the flaved portion.
- the mixing ratio (mass ratio) of water and pericarp is preferably about 0.5: 1 to 2.5: 1, more preferably about 0.6: 1 to 1.8: 1, and more preferably 0: water: pericarp.
- About 7: 1 to 1.5: 1 is more preferable, and about 0.7: 1 to 1: 1 is particularly preferable.
- a small amount of a fruit portion (such as albedo or gills) containing pectin may be mixed.
- the essential oil contained in the pericarp oil vesicles is emulsified in water using a device such as a mixer or a homogenizer that can be dispersed in water while cutting the pericarp.
- a device such as a mixer or a homogenizer that can be dispersed in water while cutting the pericarp.
- components such as glycerophospholipid and pectin can be extracted from the pericarp into water, whereby the emulsion stability of oil droplets (essential oil components) can be enhanced.
- the liquid composition thus obtained consists only of water and fruit components, has no miscellaneous taste due to components other than fruits, and exhibits a natural fruity flavor. Moreover, since essential oil does not touch air
- Example preparation The sample for analysis was prepared by the following method. First, 10 g of the liquid composition was weighed into a glass centrifuge tube (A). However, 5 g when the Brix value of the liquid composition was 10% or more, 2.5 g when 20% or more, and 1 g when 30% or more were weighed and diluted to 10 mL with distilled water for liquid chromatography. 20 mL of ethanol for liquid chromatography was added and mixed vigorously with a vortex mixer for 1 minute or longer. If the viscosity is high and it does not mix, shake it vigorously with your hands if necessary.
- the supernatant collected in the centrifuge tube (B) was further centrifuged (1620 G, 30 minutes, 20 ° C.), and the resulting supernatant was transferred to a 50 mL volumetric flask and diluted with ethanol.
- the well-mixed supernatant was further diluted 10-fold with ethanol for liquid chromatography and washed with ethanol beforehand (Toyo Roshi Kaisha, ADVANTEC DISMIC-25HP 25HP020AN, pore diameter 0.20 ⁇ m, diameter 25 mm). It filtered and it was set as the analytical sample.
- the lemon taste drink was manufactured using this invention product 1 obtained by said (1), and the comparative example 1, and the flavor was evaluated.
- each was formulated according to the formulation of Table 4, filled into a bottle, and then heat sterilized at 85 ° C. for 5 minutes to produce a lemon-taste beverage.
- Table 4 Lemon-taste beverages using the product of the present invention were sour and did not become difficult to drink even when blended in large amounts in beverages. In addition, it had a natural and fresh fragrance derived from natural citrus fruits and did not feel an irritating bitterness.
- Example 2 (1) Production of Lemon Aroma Composition A lemon aroma composition was produced in the same manner as the product 1 of the present invention in Example 1 using various kinds of lemons, and various component analyzes were performed. The results are shown in Table 5.
- the present invention products 2 to 11 obtained in (1) above were blended in a solution adjusted to a Brix value of 9.0 and an acidity of 0.15% with sucrose and anhydrous citric acid, respectively. After filling the bottle, it was sterilized by heating at 85 ° C. for 5 minutes to obtain a container-packed beverage with a lemon taste. The flavor of the obtained beverage was evaluated in the same manner as in Example 1.
- the present invention products 2 to 11 in which the acidity, the rutin concentration per acidity, the limonin concentration and the ratio thereof are in a specific range have a fresh and refreshing fragrance, which is a characteristic citrus fragrance, with suppressed stimulating bitterness. Had.
- Example 3 Using lime, a lime aroma composition was produced in the same manner as the product 1 of the present invention in Example 1, and various components were analyzed. The results are shown in Table 6. As in Examples 1 and 2, when the sensory evaluation was performed with the composition and the packaged beverage containing the composition, the stimulating bitter taste was suppressed, and a fresh and refreshing fragrance that is a characteristic citrus fragrance was obtained. It was suitable as a flavor liquid and a container-packed beverage.
- Table 7 shows the component analysis results of the composition obtained by mixing and emulsifying the flavedo fraction obtained without removing the super surface layer of the whole lemon fruit and water.
- sensory evaluation was performed with the composition and the packaged beverage containing the composition, and although it had an irritating bitter taste, it was suitable as a flavor liquid and beverage.
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Abstract
Description
・果皮精油とリモニンとルチンとを含み、
・果皮精油含量が、組成物全量に対して0.2~3.5容量%であり、
・酸度に対するリモニンの濃度が、10~300mg/kg/Acidであり、
・酸度に対するルチンの濃度が、10~50mg/kg/Acidであり、
・リモニンに対するルチンの質量比(ルチン/リモニン)が、1以下であり、
・酸度が、2.0%以下である。
本発明の組成物は、果皮精油を組成物全量に対して0.2~3.5容量%の量で含む。果皮精油とは、主に柑橘果実の果皮から採取される芳香性を有する化合物群である。果実精油は、モノテルペンやセスキテルペンなどのテルペン化合物や、芳香族化合物を主成分としており、グリセリン脂肪酸エステルを主体とする油脂とは異なる。植物からの精油の採取方法には、水蒸気蒸留法、圧搾法、溶剤抽出法、アンフルラージュ法、マセレーション法、超臨界抽出法等があり、本発明に用いる果皮精油は、公知のいずれの採取方法で得られたものであってもよいが、圧搾法により得られる精油成分を用いることが好ましい。
本発明の組成物は、リモニンを含む。リモニンは、果実中で配糖体の形(リモニングルコシド)(式1)、または配糖体から糖が外れた形(リモノエートA環ラクトン)(式2)として存在することが知られている。リモニングルコシドおよびリモノエートA環ラクトンは、苦味を呈しない。果実を搾汁後、果汁の酸性下でリモノエートA環ラクトンが閉環し、リモニン(7,16-ジオキソ-7,16-ジデオキシリモンジオール、C26H30O8)(式3)の形態となると、強い苦味を呈するようになることが知られている。
本発明の組成物は、ルチンを含む。本発明の組成物におけるルチンの濃度は10~50mg/kg/Acid、好ましくは15~45mg/kg/Acidである。ルチンを一定範囲の濃度で液状組成物に含有させることにより、リモニンの苦味を低減させることができる。ただし、リモニンに一定割合以上のルチンを共存させた場合、かえってリモニンの強い苦味がルチンにより増強されることがある。ルチンのリモニンに対する質量比(ルチン/リモニン)は好ましくは1以下であり、より好ましくは0.8以下であり、さらに好ましくは0.6以下である。なお、ここでいう「強い苦味」とは、舌粘膜の収斂による物理的刺激を意味し、過剰な苦味、不快な苦味を表し、化学的刺激として許容される適度な苦味とは異なるものである。一般に、閾値以下の微量な苦味物質は、食品や料理の味わいを複雑で深みのあるものにすることが知られている。また、苦味には甘味との対比効果があることが知られている。しかし、柑橘果実の果皮等に存在するリモニンの苦味は、刺激性のある過剰な苦味であり、不快なものと知覚されることが多い。本発明は、このリモニンに対するルチンの比を1以下に抑えることにより、「強い苦味」を選択的に低減しうるものである。
柑橘果実の果皮精油は、酸度が高いと容易に変質し、薬品的な臭いとなる。本発明の組成物は、酸度を低く抑えることで、自然で新鮮かつ劣化も少ないアロマ組成物となる。本発明の組成物の酸度は、2.0%以下であり、好ましくは0.1~1.5%であり、より好ましくは0.2~1.2%であり、さらに好ましくは0.2~1.0%である。上記のルチン/リモニン比を1以下に抑えることに加え、組成物の酸度を上記の範囲に調整することにより、組成物の強い苦味をさらに効果的に抑制できることを見出した。なお、本明細書でいう「酸度」とは、前述の通り、クエン酸、リンゴ酸などの有機酸の含有量を水酸化ナトリウムによる中和滴定法で測定し、値をクエン酸含有量に換算して質量%で表したものをいう。酸度の高い果実のコミニュテッド果汁は、飲料に多量に配合すると飲料が酸っぱくなり飲みにくくなるので、飲料中に多量に配合することができないという問題があるが、本発明の酸度の低い液状組成物は、リモニンの強い苦味が感じられにくくなるという上記の利点だけではなく、飲料中に多量に配合できるので果実精油の香気成分を飲料に多量に含有させることができるという利点も有する。
本発明の組成物は常温常圧で液状である。水を主な溶媒とすることが好ましい。pHは好ましくは5未満である。pHが低いことは、腐敗菌の抑制に有利である。
本発明者らは果皮中のルチン濃度が異なる果実から果汁を製造する中で、果皮精油、リモニン、及びルチンの量と、酸度を調整することにより、刺激的な苦味を感じず、天然の果実に近い新鮮な香味を有する液状組成物を得ることができることを見出した。
糖度(Brix値;%)の測定は、デジタル屈折計(会社名:アタゴ社製、型番:RX-5000α)を用い、20℃で行った。
液状組成物10gを希釈して一定容として、供試液とした。供試液の一定量について、フェノールフタレインをpH指示薬とし、0.1mol/L水酸化ナトリウム標準液で滴定し、以下の計算式により滴定酸度を算出した:
酸度(%) = K×(T-B)×F×(100/A)×(1/W)×100
K:クエン酸換算=0.0064
T:0.1mol/L水酸化ナトリウム溶液の滴定量(ml)
B:同量の水における0.1mol/L水酸化ナトリウム溶液の滴定量(ml)
F:0.1mol/L水酸化ナトリウム溶液の力価
A:滴定の際に採取した試料容量(ml)
W:調製の際に採取した試料重量(g)。
組成物中の精油含量の測定には、精油定量装置を用いた。精油を捕捉できる冷却装置のついた丸型フラスコに、液状組成物100mL、蒸留水2L、沸騰石を加え、加温して約100℃で1時間、常温蒸留を行い、捕捉管に溜まった精油量(mL)を測定して精油含量を算出した。
リモニンおよびルチンは、LC-MSを用いて分析した。
(サンプルの調製)
分析用サンプルは、以下の方法で調製した。まず、ガラス製遠沈管(A)に液状組成物10gを秤量した。ただし、液状組成物のBrix値が10%以上の場合は5g、20%以上の場合は2.5g、30%以上の場合は1gを秤量し、液体クロマトグラフィー用蒸留水で10mLに希釈した。液体クロマトグラフィー用エタノール20mLを加え、ボルテックスミキサーにて1分以上激しく混和した。粘性が高く混ざらない場合は、必要に応じて手などで激しく振り混ぜた。これを遠心器に供し(1620G、30分、20℃)、上清を別のガラス製遠沈管(B)に移した。沈殿物に液体クロマトグラフィー用エタノール20mLを加え、固形分を薬匙などで十分に崩した後、ボルテックスミキサーにて1分以上激しく混和した。遠心器で遠心(1620G、30分、20℃)し、上清を遠沈管(B)に加えた。遠沈管(B)に集めた上清は、さらに遠心(1620G、30分、20℃)し、得られた上清を50mLのメスフラスコに移し、エタノールでメスアップした。よく混和した上清液を、さらに液体クロマトグラフィー用エタノールで10倍に希釈し、予めエタノールで洗浄したPTFE製フィルター(東洋濾紙社製、ADVANTEC DISMIC-25HP 25HP020AN,孔径0.20μm、直径25mm)で濾過し、分析試料とした。
(LC分析条件)
HPLC装置:Nexera XRシリーズ(島津製作所社製、システムコントローラー:CBM-20A、送液ポンプ:LC-20ADXR、オンライン脱気装置:DGU-20A3、オートサンプラー:SIL-20ACXR、カラムオーブン:CTO-20A、及びUV/VIS検出器:SPD-20Aを有する)
カラム:CAPCELL CORE AQ(粒径2.7μm、内径2.1mm×150mm、資生堂社製)
移動相A:ギ酸0.1%水溶液
移動相B:アセトニトリル
流量:0.6mL/min
濃度勾配条件:0.0~0.5分(15%B)→6.0分(25%B)→10.0分(75%B)→10.1~11.0分(100%B)、初期移動相による平衡化3.0分
カラム温度:40℃
試料注入:注入量2.0μL
質量分析装置への試料導入:1.8~11.0分
(質量分析条件)
質量分析装置:4000 Q TRAP(AB Sciex社製)
イオン化方法:ESI(Turbo Spray)、ポジティブモード
イオン化部条件:CUR:10、IS:5500、TEM:650、GS1:80、GS2:60、ihe:ON、CAD:Medium
検出方法:MRMモード
検出条件(Q1→Q3、DP、CE、CXP、EP):
ルチン(611.2→303.1、76、25、12、10)
リモニン(471.2→425.1、101、29、12、10)
ピーク検出時間:標品による確認を要するが、概ね下記の通りである。
ルチン(3.01分)、リモニン(8.80分)
標準品は和光純薬工業社より購入した。濃度の異なる標品溶液3点以上を供し、得られたピーク面積による絶対検量線法で定量した。測定の結果、測定値が検量線の範囲に入らない場合は、分析試料調製の過程の最後における、エタノールによる希釈の倍率を適宜調整し、再度測定を実施した。
(1)レモンアロマ組成物の製造
根菜類用の回転ドラム式皮むき装置を用いて、レモン全果の超表層部を、油胞の90%以上が残る程度に、除去した。得られたレモン加工品を半分に切断し、果肉、種子、じょうのう膜、アルベドの大部分を取り除いて超表層部の取り除かれたフラベドを得た。得られたフラベドを、フラベド:水=1:1の質量比で混合し、市販のジュースミキサーにて混合液がペースト状にならない程度にミリング処理し、30分間常温にて攪拌した後、40メッシュストレーナーで固液分離を行った。その後に0.2MPaにてホモジナイズし、得られた懸濁物から不溶性固形分を遠心分離(6000G5分間)で除去し、90℃1分間の加熱殺菌をして液状組成物(本発明品1)とした。また、レモン全果の超表層部を除去しないこと以外は本発明品1と同様にして液状組成物(比較例1)を得た。本発明品1と比較例1とを比較した結果を表3に示す。なお、各種成分の測定に際しては、上記した方法を用いた。超表層部を除去した本発明品1は、酸度に対するルチン含量が大きく低減していた。
上記(1)で得られた本発明品1及び比較例1を、直接舐めてその風味を評価した。評価は、刺激的な苦味の強さ、自然で新鮮な芳香の強さを、表2に示す基準で、評点法(5点法)により行った。結果を表3に示す。本発明品はリモニン濃度が高いにも関わらず、比較例と比べて刺激的な苦味が劇的に低減されていた。これより、酸度に対するルチンの濃度、酸度に対するリモニンの濃度及びこれらの比率を制御することで、新鮮で強い芳香を有しながらも刺激的な苦味がない香味液が得られることが示唆された。
(1)レモンアロマ組成物の製造
いろいろな種のレモンを用い、実施例1の本発明品1と同様にしてレモンアロマ組成物を製造し、各種成分分析を行った。結果を表5に示す。
上記(1)で得られた本発明品2~11を、ショ糖及び無水クエン酸にてBrix値9.0及び酸度0.15%に調整した溶液にそれぞれ10g/L配合し、瓶に充填した後、85℃5分間で加熱殺菌し、レモンテイストの容器詰飲料を得た。得られた飲料を実施例1と同様にして風味を評価した。酸度、酸度あたりのルチン濃度、リモニン濃度及びこれらの比率が特定範囲にある本発明品2~11は、刺激的な苦味が抑制され、柑橘の特徴的な香気である、新鮮で爽やかな香気を有していた。
ライムを用い、実施例1の本発明品1と同様にしてライムアロマ組成物を製造し、各種成分分析を行った。結果を表6に示す。実施例1および2と同様に、組成物及び組成物を含有した容器詰飲料で官能評価を行ったところ、刺激的な苦味が抑制され、柑橘の特徴的な香気である新鮮で爽やかな香気を有しており、香味液および容器詰飲料として好適であった。
レモン全果の超表層部を除去せずに得られたフラベド画分と水を混合乳化し得られた組成物の成分分析結果を表7に示す。実施例1および2と同様に、組成物及び組成物を含有した容器詰飲料で官能評価を行ったところ、刺激的な苦味があるものの、香味液および飲料として好適であった。
Claims (5)
- 果皮精油とリモニンとルチンとを含み、
果皮精油含量が、組成物全量に対して0.2~3.5容量%であり、
酸度に対するリモニンの濃度が、10~300mg/kg/Acidであり、
酸度に対するルチンの濃度が、10~50mg/kg/Acidであり、
リモニンに対するルチンの質量比(ルチン/リモニン)が、1以下であり、
酸度が、2.0%以下である、液状組成物。 - リモニンが、果実由来のものである、請求項1に記載の液状組成物。
- ルチンが、果実由来のものである、請求項1または2に記載の液状組成物。
- 油胞を壊さない程度の厚さで超表層部を取り除いた柑橘果実の果皮と、溶媒とを用いて得られた、請求項1~3のいずれか1項に記載の液状組成物。
- 請求項1~4のいずれか1項に記載の液状組成物を飲料全体の量に対して、0.1~15質量%の濃度で含む、飲料。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019129718A (ja) * | 2018-01-29 | 2019-08-08 | 長岡香料株式会社 | 抽出物の製造方法 |
JP2020043771A (ja) * | 2018-09-14 | 2020-03-26 | サッポロビール株式会社 | 浸漬酒およびアルコール飲料の製造方法、ならびに、浸漬酒およびアルコール飲料の香味向上方法 |
US20210212344A1 (en) * | 2018-09-03 | 2021-07-15 | Societe Des Produits Nestle S.A. | Maceration composition and method for preparing same |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113208107A (zh) * | 2021-04-01 | 2021-08-06 | 王允太 | 一种保健柚子油及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07165547A (ja) * | 1993-12-14 | 1995-06-27 | Lion Corp | 口腔用組成物 |
JP2000350571A (ja) * | 1999-04-05 | 2000-12-19 | Takara Shuzo Co Ltd | アルコール含有香味液及びアルコール飲料 |
JP2008061511A (ja) * | 2006-09-04 | 2008-03-21 | Mitsui Sugar Co Ltd | 風味改善剤、これを用いた風味改善方法及び飲食品 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4608266A (en) * | 1983-05-31 | 1986-08-26 | Brown International Corporation | Process for forming a citrus juice extender |
JP2007112892A (ja) * | 2005-10-20 | 2007-05-10 | Sakamoto Koryo Kk | 香酸カンキツ類の精油の製法 |
US20100159115A1 (en) * | 2008-12-19 | 2010-06-24 | Niv Ben Yehuda | Flavonoid-rich citrus extract process |
US9545117B2 (en) * | 2009-02-03 | 2017-01-17 | Tropicana Products, Inc. | Microencapsulated citrus phytochemicals and application to beverages |
US20100196549A1 (en) * | 2009-02-03 | 2010-08-05 | Tropicana Products, Inc. | Microencapsulated citrus phytochemicals and application to sports drinks |
JP5178615B2 (ja) * | 2009-04-21 | 2013-04-10 | サントリーホールディングス株式会社 | 柑橘果実の自然な香味を向上させる柑橘果実混合物及びそのアルコール抽出液 |
-
2015
- 2015-03-16 ES ES201530336A patent/ES2583164B1/es active Active
-
2016
- 2016-03-15 WO PCT/JP2016/058184 patent/WO2016148151A1/ja active Application Filing
- 2016-03-15 US US15/558,060 patent/US20180064141A1/en not_active Abandoned
- 2016-03-15 JP JP2017506571A patent/JP6745790B2/ja active Active
- 2016-03-15 EP EP16764981.3A patent/EP3272227B1/en active Active
- 2016-03-15 ES ES16764981T patent/ES2836280T3/es active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07165547A (ja) * | 1993-12-14 | 1995-06-27 | Lion Corp | 口腔用組成物 |
JP2000350571A (ja) * | 1999-04-05 | 2000-12-19 | Takara Shuzo Co Ltd | アルコール含有香味液及びアルコール飲料 |
JP2008061511A (ja) * | 2006-09-04 | 2008-03-21 | Mitsui Sugar Co Ltd | 風味改善剤、これを用いた風味改善方法及び飲食品 |
Non-Patent Citations (3)
Title |
---|
LIU, Y. ET AL.: "Water-based extraction of pectin from flavedo and albedo of orange peels.", CHEMICAL ENGINEERING JOURNAL, vol. 120, no. 3, 2006, pages 203 - 209, XP028035985 * |
POIANA, M. ET AL.: "Supercritical carbon dioxide (SC-CO2) extraction of grapefruit flavedo.", FLAVOUR AND FRAGRANCE JOURNAL, vol. 13, no. 2, 1998, pages 125 - 130, XP055312213 * |
YASUHIRO OKUBO: "Production Technology and Feature of Functional Emulsion, using Food Emulsifier", THE FOOD INDUSTRY, vol. 56, 2013, pages 66 - 73, XP009505923 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019129718A (ja) * | 2018-01-29 | 2019-08-08 | 長岡香料株式会社 | 抽出物の製造方法 |
JP7049573B2 (ja) | 2018-01-29 | 2022-04-07 | 長岡香料株式会社 | 抽出物の製造方法 |
US20210212344A1 (en) * | 2018-09-03 | 2021-07-15 | Societe Des Produits Nestle S.A. | Maceration composition and method for preparing same |
JP2020043771A (ja) * | 2018-09-14 | 2020-03-26 | サッポロビール株式会社 | 浸漬酒およびアルコール飲料の製造方法、ならびに、浸漬酒およびアルコール飲料の香味向上方法 |
JP7208748B2 (ja) | 2018-09-14 | 2023-01-19 | サッポロビール株式会社 | 浸漬酒およびアルコール飲料の製造方法、ならびに、浸漬酒およびアルコール飲料の香味向上方法 |
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ES2836280T3 (es) | 2021-06-24 |
US20180064141A1 (en) | 2018-03-08 |
ES2583164B1 (es) | 2017-07-10 |
EP3272227A1 (en) | 2018-01-24 |
JPWO2016148151A1 (ja) | 2018-01-18 |
EP3272227A4 (en) | 2018-09-12 |
ES2583164A1 (es) | 2016-09-19 |
EP3272227B1 (en) | 2020-10-28 |
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