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    • 专利摘要:
    Liquid compositions containing essential oils extracted from the peel of citrus fruits. A liquid composition suitable for inclusion in beverages containing 0.2-3.5% by volume of an essential oil of the peel of a citrus fruit with high citric aroma and acid taste, 5-20 mg/kg/citropten acid and 300 mg/kg/acid or more of hesperidin. Preferably, the liquid composition further contains rutin at a concentration of 50 mg/kg/acid or less. Citrophene, hesperidin and rutin are preferably extracted from the skin of one or more of the citrus fruits. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2583162A1
    申请号:ES201530335
    申请日:2015-03-16
    公开日:2016-09-19
    发明作者:Daigo IBUSUKI；Masaru Fujiwara；Yoshiaki Yokoo
    申请人:Suntory Beverage and Food Ltd；
    IPC主号:
    专利说明:

    LIQUID COMPOSITIONS CONTAINING ESSENTIAL OILS EXTRACTED
    OF THE CRITICAL FRUIT Husk
    TECHNICAL FIELD
    The present invention relates to liquid compositions containing oils
    5 essentials extracted from citrus fruits with high citrus aroma and acid taste. Plusparticularly, the present invention relates to liquid compositions thatthey comprise essential oils of the shell and specified amounts of citroptene andHesperidine and that can be included in drinks.
    STATE OF THE TECHNIQUE
    10 Rich fruit with high citrus aroma and acidic taste such as lemon or lime has high acidity and is unsuitable for raw eating, but the distinctive fragrance of the essential oil components contained in its peel is appreciated. Thus, the juice is squeezed from said fruit and added to dressings and drinks. Citrus juice with high citrus aroma and acid taste is normally produced by the online procedure. This
    15 method is known for providing juice that has a characteristic fresh and pleasant smell of citrus fruit with high citrus aroma and acidic flavor since the essential oil of the peels is included in the juice in an amount of approximately 0.01-0 , 03%, and the remaining peels, segment membranes and nuggets that confer an undesirable aroma and flavor when separated from the juice during squeezing. Without
    However, the aromatic components of citrus fruit with high citrus aroma and acid taste are not stable and their quality decreases significantly during thermal pasteurization, storage or distribution: the fresh and pleasant smell decreases, and deteriorated odors such as similar smell occur to chemical or oxidized products. To address this problem a method has been proposed to
    25 stably maintain the aroma of citrus juice with a high citrus aroma and acidic flavor that includes squeezing said citrus fruits and immediately add a pH adjuster to them to control the pH of the juice from 3.5 to 7.0 (patent application JP 2000-308475A).
    In the case of producing drinks from high acidity fruits, such as citrus fruits
    30 with high citrus aroma and acid taste, its juice cannot be included in large quantities since the resulting products reach such high acidity that they are not easy to drink. To treat this problem, it has been proposed to reduce the acidity or bitterness by adding a hesperidin glycoside or the mixture of a hesperidin glycoside with hesperidin to citrus juice (JP patent application H11-318379 A). Therefore, a method has been proposed to increase an aroma and flavor similar to that of fruit juice, adding citroptene to beverages (patent application JP 2011-055797 A).
    SUMMARY OF THE INVENTION
    It is an object of the present invention to provide liquid compositions havingabundant aromas reminiscent of natural citrus fruits with high citrus aroma andacid taste and that after prolonged storage retain the aromas ofstable way.
    The present inventors made extensive studies that were based on the
    10 concentrations of citroptene and hesperidin in fruit juice, and found a citroptene effect of aroma and flavor enhancement similar to that of fruit juice, further increased when combined with hesperidin. However, in the case of juice that has high acidity, such as citrus fruit juice with high citrus aroma and acid taste, there was a tendency to produce a deteriorated smell to some
    15 concentrations of citroptene and hesperidin, and a characteristic aroma of citrics with high citrus aroma and acid taste tended to be lost after prolonged storage. As a result of extensive research to solve the problem, the inventors found that a liquid composition that was obtained by crushing the peel in the water had a fresh and pleasant fragrance characteristic of citrus fruits
    20 with a high citrus aroma and acid taste even when it did not contain fruit juice. The inventors have completed the present invention by discovering that, by precisely controlling the acidity and concentrations of citroptene and hesperidine in addition to the essential oils of citrus fruits with high citrus aroma and acid taste, it is possible to avoid changes in aroma at a high level even in the case of being stored during a
    25 long time.
    Specifically, the liquid composition:
    it comprises an essential oil of the peel of a citrus fruit with a high citrus aroma and acid taste, citroptene and hesperidin; in which
    the content of the essential oil of the shell is in the range of 0.2-3.5% in 30 volume of the total amount of the composition;
    the concentration of citroptene with respect to acidity is in the range of 5-20 mg / kg / acid; Y
    The concentration of hesperidin with respect to acidity is 300 mg / kg / acid or more.
    The citroptene and hesperidin described above can be derived from one or more citrus fruits. The liquid composition described above may comprise the essential oil and citroptene and hesperidin obtained from one or more citrus fruits. Compared to conventional types of fruit juice (including crushed juice), the liquid composition has higher concentrations of citroptene and hesperidin. It should be noted here that in the present invention "mg / kg / acid"; As a unit of concentrations, it is obtained by dividing the concentration of each component in the composition (mg / kg) by the acidity of the composition. The acidity as used herein is determined by first measuring the content of organic acids in a liquid by titration by neutralization with sodium hydroxide, calculating it in terms of citric acid and expressing the converted value as a percentage. The present inventors found that, by incorporating citroptene and hesperidin into the liquid composition at certain concentration ranges, an aroma and flavor reminiscent of natural fruits was significantly enhanced and that after prolonged storage it was conserved stably.
    The liquid composition preferably has an acidity of 2.0 or less and has a much lower acidity than that of conventional types of fruit juice. By limiting the acidity to a lower level, the decrease or deterioration of the aroma that occurs during the thermal pasteurization process or during prolonged storage can be suppressed. Conventional types of juice are limited in the amount of inclusion in beverages since such juice has high acidity and, if included in a large amount, the resulting products become so sour that they are not easy to drink. On the other hand, a liquid composition with low acidity can be incorporated into beverages in a large amount without excessively increasing the acidity of the beverages.
    The liquid composition set forth above preferably has a routine concentration with respect to acidity of 50 mg / kg / acid or less. By limiting the routine concentration so that it is within a certain range, the long-lasting irritating bitterness can be suppressed and an aroma and flavor similar to the natural citroptene fruit becomes more noticeable.
    BRIEF DESCRIPTION OF THE DRAWINGS
    Fig. 1 is a cross section of a citrus fruit.
    EMBODIMENTS OF THE INVENTION
    lt; Essential oils of the shell;
    The composition of the present invention contains essential oils of citrus peel with high citrus aroma and acid taste in amounts ranging from 0.2 to 3.5% by volume of the total amount of the composition. Essential oils are a class of aromatic compounds that are collected primarily from citrus peels. Essential oils are based on terpenic compounds such as monoterpenes and sesquiterpenes and differ from oils and fats that are based on glycerides. Although the essential oils of the shell to be used in the present invention can be obtained by any of the known methods, it is preferable to use the essential oil components that are obtained by expression.
    The term quot; expressionquot; or squeezing action, as used herein, refers to a method in which a physical force is applied to the peel of a fruit so that an essential oil is obtained from the oil cells present in the colored portion from the shell. In a known example of the expression process, the shell is mechanically damaged to break the oil sacks, from which an essential oil is extracted (Florida Citrus Oils, Kesterson et al., Technical Bulletin 749, December 1971, p. 15 -twenty). As will be described later, the shell containing an essential oil can be emulsified by crushing in water and this method is also included in the expression process. The citrus peel includes a portion of dark colored flavedo and a portion of white fibrous albedo, the flavedo containing many sacks of oil containing a large amount of essential oil (see Fig. 1 cited in quot; Kajitsu no Jiten (Dictionary of Fruits), published by Asakura Shoten, 2008, p. 198). In the present invention, the shell, or the flavedo in particular, is collected and, by emulsifying the shell containing the oil sacks as it is crushed in water, a liquid composition containing the essential oil of the shell can be obtained. In the process, the shell or flavedo is preferably collected in such a way that the oil sacks are kept intact as far as possible until they break into the water. By keeping the oil bags intact until they are emulsified in water, it is possible to prevent the essential oil in the oil bags from coming into direct contact with oxygen to reduce the possibility that the aroma components in the essential oil may deteriorate after oxidation. The essential oil thus obtained is advantageous because it is less susceptible to heat and oxygen and because, therefore, the aroma components will experience less deterioration. When the cold pressing method or other conventional technique is used to obtain an essential oil from the shell, it is necessary to remove an essential oil from the oil sacks before the process is completed, so that its aroma components can deteriorate under the direct action of oxygen.
    Examples of citrus fruits with high citrus aroma and acid flavor that are to be used to obtain essential oils from the peel include those that have juice with an acidity of at least 0.40%. Fruits that are advantageous for the present invention include Citrus liman, Citrus aurantifolia, Citrus sudachi, Citrus sphaerocarpa, Citrus depressa, Citrus junos and the like.
    The concentration of the essential oil of the shell in the liquid composition ranges from 0.2 to 3.5% by volume of the total amount of the composition. Preferably, it ranges from 0.3 to 3.0% by volume, more preferably from 0.4 to 2.5% by volume, even more preferably from 0.4 to 2.0% by volume, and particularly preferably from 0.4 to 1.5% by volume. The concentration of the essential oil of the shell in the composition can be measured with an essential oil test apparatus, or with a distillation system using an essential oil quantification device, as will be described later in the examples.
    <Citroptenogt;
    The composition of the present invention comprises citroptene, in addition to the essential oil of the shell. Citroptene (5,7-dimethoxycoumarin, molecular formula Cll HlO0 4) is a component that has a slight bitterness found in the peel or oil in the citrus peel.
    The concentration of citroptene in the composition is in the range of 5-20 mg / kg / acid, preferably in the range of 8-18 mgJkg / acid. Here it should be noted that the unit "mg / kg / acid"; it refers to the concentration of citroptene with respect to acidity and which comes from the concentration of citroptene in the composition (mg / kg) as a result of dividing it by the acidity of the composition. The acidity as used herein is determined by first measuring the content of organic acids in the composition by titration by neutralization with sodium hydroxide, calculating it in terms of citric acid and expressing the converted value as a percentage. The concentration of citroptene in the liquid composition of the present invention is generally higher than that of conventional types of fruit juice (including crushed juice).
    The citroptene contained in the liquid composition of the present invention is preferably obtained from citrus fruits, in particular, preferably from citrus fruits with high citrus aroma and acid taste, although this is not the only example of citroptene that can be used in the present invention. Using the citroptene obtained from the peel and combining it with the essential oil of the peel, a composition would be obtained whose aroma is even more similar to that of natural citrus fruits and that has high stability during storage.
    The concentration of citroptene to be used in the present invention can be adjusted by adding a commercially available citroptene to the composition. Alternatively, as will be understood from the method to be described later, the same result can be obtained by emulsifying the shell or flavedo that contains the essential oil as they are crushed into the water so that the citroptene obtained from the shell is extracted in The liquid composition. The concentration of citroptene in the liquid composition can be measured using LC-MS, as will be described later in the examples.
    <Hesperidinagt;
    The composition of the present invention comprises hesperidin, in addition to the essential oil of the shell and citroptene. Hesperidin (molecular formula C2sH34 0, s) is a type of flavanone glycoside and is a component found in the peel, segment membrane, or the like in citrus fruits.
    The concentration of hesperidin in the composition is preferably at least 300 mg / kg / acid, more preferably in the range of 300-800 mg / kg / acid, even more preferably between 350-700 mg / kg / acid. The present inventors found that, by adjusting the concentrations of citroptene and hesperidin with respect to acidity, it is possible to give the composition an aroma and flavor similar to natural fruit and improve its stability during storage. It is already known that citroptene has moderate bitterness and astringency and, if added to beverages that have zero or low fruit juice content, citroptene gives drinks a similar aroma and flavor to fruit juice (JP 2011-055797 TO); however, it has never been known that this action can be enhanced by combining the contained hesperidin at a certain concentration range with the citroptene. Hesperidin has no taste or smell, and so it is surprising that the action of citroptene can be enhanced by hesperidin.
    The hesperidin contained in the liquid composition of the present invention preferably comes from one or more citrus fruits, particularly preferably from one or more citrus fruits with high citrus aroma and acidic taste, although this is not the only example of hesperidin that can be used in The present invention. Using the hesperidin extracted from the peel and combining it with the essential oil of the peel would obtain a composition whose aroma is even more similar to that of natural citrus fruits.
    The concentration of hesperidin to be used in the present invention can be adjusted by adding a commercially available hesperidin to the composition. Alternatively, as will be understood from the method to be described later, the same result can be obtained by emulsifying the shell or phtavedo containing the essential oil as they are crushed into the water so that the hesperidine obtained from the shell is extracted in The liquid composition. The concentration of hesperidin in the liquid composition can be measured using LC-MS, as will be described later in the examples.
    <Rutinagt;
    The routine concentration in the composition of the present invention is preferably 50 mg / kg / acid or less, more preferably 5-50 mg / kg / acid, even more preferably in the range of 10-40 mg / kg / acid. . By incorporating routine into the liquid composition at a certain concentration range, a hesperidin action to enhance the aroma and taste of citroptene can be synergistically increased. Rutin (quercetin-3-glycoside, molecular formula C27H300 '6) is a type of flavone glycoside and is known to be contained in buckwheat (Fagopyrum escufentum), asparagus, etc. , and it is also known to be contained in the peel and other citrus fruits. The present inventors found that by adjusting the routine concentration in the composition containing the essential oil of the peel, citroptene and hesperidin so that it is within a certain range, the irritating intense bitterness and long-lasting specificity for fruits can be suppressed citrus fruits with high citrus aroma and acid taste. The routine has no taste or smell, and thus it is surprising that bitterness can be suppressed by limiting the amount of routine.
    The routine contained in the liquid composition of the present invention preferably comes from one or more citrus fruits although this is not the only routine example that can be used in the present invention. The routine concentration can be adjusted by adding a certain amount of commercially available rutin to the composition containing the essential oil of the peel, citroptene and hesperidin, or it can also be adjusted by the routine addition or removal of the liquid composition obtained by the use of citric fruits. As will be understood from the method to be described later, the liquid composition can be obtained by emulsifying the shell or tlavedo containing the essential oil as it is crushed into the water so that the essential oil, from the liquid composition, is extracted from the shell, citroptene and hesperidin. In this case, normally, a large amount of routine is also extracted in the liquid composition, so that an appropriate amount thereof must be removed to limit its concentration within the aforementioned ranges. In this regard, the present inventors have found a convenient method to limit the routine concentration in the composition so that it is within the aforementioned ranges, namely, they have found that the routine concentration can be reduced by removing the upper surface layer of the peel very finely (at a thickness such that the oil sacks remain intact) before crushing the shell or tlavedo into the water. Although it was already known that the routine is contained in the citrus peel, the present inventors first discovered that the routine content is high, in particular, close to that of the outer surface of the peel. Routine concentration in the liquid composition can be measured using LC-MS, as will be described later in the examples.
    <Acidity
    If the essential oils of citrus fruit with high citrus aroma and acid taste are placed under conditions of high acidity, its fresh and pleasant aroma will easily decrease giving a deteriorated smell similar to chemical. The composition of the present invention, which is of reduced acidity, can be used as an aroma composition that is more natural and fresh with less deterioration. The composition of the present invention has an acidity (as calculated for citric acid) of 2.0% or less, preferably 0.1-1.5%, more preferably 0.2-1.2%, and even more preferably 0.2-1.0%. Unlike conventional types of juice (including crushed fruit juice), the composition of the present invention does not contain fruit juice components, so that although high acidity fruits are used, the acidity of the composition can be reduced to lower levels.
    Furthermore, if the composition of the present invention has a lower Brix value, an aroma composition can be obtained which will experience even less deterioration. The composition of the present invention preferably has Brix of 25% or less, more preferably 20% or less, even more preferably 15% or less, and particularly preferably 1-10%.
    <Liquidation composition;
    The composition of the present invention is in a liquid state at room temperature under atmospheric pressure. It preferably comprises water as solvent
    5 main. Preferably, the composition comprises 1% by weight or less of ethanol, more preferably without ethanol. The liquid composition of the present invention preferably has a pH of less than 5, more preferably less than 4, still more preferably less than 3.5. The low pH condition is advantageous to suppress the growth of degradation microorganisms.
    As will be described later in a more specific form, a possible method for producing the liquid composition of the present invention comprises the following procedure: the shell or flavedo having oil sacks containing an essential oil is emulsified as it is crushed in water, after which the essential oil is removed from the oil sacks in the water and the citroptene and hesperidin are extracted from the
    15 shell in the water. As a result, a liquid flavor can be produced characterized by "do not use food additives". For the term "additives" are not used; it is indicated that none of the additives in the "List of Products in the Registry of Existing Additives"; specified in the Japanese Food Health Act has been added "externally". The liquid composition, which consists solely of the components
    20 obtained from fruits and water, has an aroma and taste similar to that of natural fruit and is preferred because the effects of the present invention develop more markedly.
    The liquid composition of the present invention can be incorporated into foods and beverages in order to flavor them. In the case of beverages, for example, the composition 25 may be incorporated at concentrations ranging from 0.1 to 15% by weight, preferably 0.5 to 10% by weight, depending on the aroma and flavor to be conferred. Being an aqueous composition that is low in both acidity alone and acidity in Brix and that is relatively high in the essential oil content of the shell, the liquid composition of the present invention has the advantage that it can be incorporated into beverages in quantities large enough to ensure that the aroma components of the essential oil of the shell are widely contained in beverages. Particularly in the case of producing drinks with the flavor of citrus fruit of high acidity, the aroma of the fruit can be reproduced within the drinks. The liquid composition of the present invention can also be used to confer flavor.
    from fruit to black tea or other tea drinks. Beverages in which the liquid composition of the present invention may be used are not particularly limited and may include various types such as alcoholic beverages, non-alcoholic beverages, carbonated beverages, juice-containing beverages and tea-based beverages. The fact that if the liquid composition does not contain alcohol (ethanol), it can be used advantageously to flavor non-alcoholic drinks deserves particular mention. In particular, it can be used advantageously to flavor low-juice beverages (non-alcoholic beverages) in the range of about 1-30% by weight, preferably 1-20% by weight, and more preferably 1-10 % by weight, and this allows the manufacture of drinks that reproduce the fragrance of natural fruits. Using the liquid composition of the present invention, it is also possible to make beverages that do not contain synthetic additives such as flavors and synthetic surfactants.
    <Production method
    The liquid composition of the present invention can be produced by adjusting the essential oil of the shell, the amounts of citroptene and hesperidine and acidity. If desired, the composition can be produced using only one or more fruits and water according to the method described below, which is given here for illustrative purposes only and is not the only example that can be used. The liquid composition, which consists solely of components obtained from the fruit and water, has an aroma more similar to that of a natural fruit and, therefore, is preferred.
    First, the peel of a citrus fruit is collected by a commonly used technique. The collected shell consists of a portion of dark colored flavedo that has sacks of oil and a portion of white fibrous albedo that does not contain oil sacks, the albedo portion of the shell has fewer aroma components than the flavedo portion; furthermore, depending on the fruit from which it comes, the albedo portion may have a bitter taste, so that the flavedo portion can be collected after most of the albedo portion of the shell has been removed. In this process, a small amount of the albedo portion may become included in the lump portion. In the process of collecting the shell or flavedo, attention will preferably be given to ensure that the oil sacks in the furnace are destroyed to a minimum. By not destroying the oil bags, the essential oil contained in the oil bags can be protected from oxidative deterioration.
    The collected shell or flavedo is then mixed with water. The ratio of water mixture to shell (by weight) is preferably in the range of
    about 0.5: 1 to about 2.5: 1, more preferably from about 0.6: 1 to about 1.8: 1, even more preferably from about 0.7: 1 to about 1.5: 1, and particularly preferably from about 0.7: 1 to about 1: 1. After mixing the shell with water, an apparatus such as a mixer or homogenizer can be used that can disperse the shell in the water while grinding it into pieces to form an emulsion in water of the essential oil contained in the oil sacks in the shell and to extract citroptene and hesperidin from the shell in water. If the shell or flavedo collected taking care to keep the oil bags intact as much as possible is mixed with water and the essential oil is emulsified while the oil bags are broken into the water, direct contact of the oil can be avoided. Essential oil with the atmosphere to reduce its deterioration. From the resulting mixture of water and the broken shell, the solids content is removed by centrifugation or otherwise giving a liquid composition. The liquid composition thus obtained consists solely of water and the 15 fruit components and, in the absence of any strange flavor due to components other than the fruit, presents an aroma and flavor that resemble those of the natural fruit. As another advantage, it should be noted that, since the essential oils of the shell do not come directly into contact with atmosphere (oxygen) during the production of the liquid composition, the aroma components will experience less
    20 oxidative deterioration and the composition produced will present a fresh aroma and flavor.
    After collecting the shell or flavedo, before mixing it with water, the upper surface layer of the shell or flavedo can be removed by slicing the shell thinly enough so as not to break the oil sacks in the flavedo. The flavedo has an oil sack fabric that collects the essential oil and there are an uncountable number of embedded points on the surface of the flavedo fruit. The upper surface layer of the flavedo refers to an extreme surface layer that has a thickness such that the surface of the fruit with embedded points would be smooth if this layer were removed, which means that the thickness is normally within 1 mm of the external surface of the peel, preferably within 0.7 mm, although it varies with the types of fruit. The inventors have found that, by removing the upper surface layer of the shell and then crushing the shell into the water, the routine content can be significantly reduced compared to a case in which the upper surface layer has not been removed. Therefore, a liquid composition is preferred in which the routine concentration is limited within a certain range and not only has an aroma and flavor reminiscent of a natural fruit enhanced by
    Citroptene and Hesperidine, but also have a prolonged and irritating reduced bitterness.
    EXAMPLES
    In the following pages, several examples of the present invention are provided, but it should be understood that the present invention is not limited to these
    examples.
    (1) Measurement of soluble solid content Measurement of soluble solid content (Brix:%) was performed with
    digital (manufactured by ATAGO CO., LTD .; model n 'RX-5000a) at 20' C. 10 (2) Acidity measurement
    a refractometer
    Ten grams of a liquid composition were diluted to a indicated volume, thus preparing a test solution. A given amount of a test solution was titrated with a standard 0.1 molll sodium hydroxide solution using phenolphthalene as a pH indicator and the valueable acidity was calculated by the following formula:
    15 Acidity (%) = K x (T-B) x F x (100 / A) x (1 / W) x 100
    K: calculated for citric acid = 0.0064
    T: the amount of 0.1 molll sodium hydroxide solution used for titration (mi)
    B: the amount of 0.1 molll sodium hydroxide solution used for titration in the same amount of water (mi)
    20 F: the dissolution factor of sodium hydroxide 0.1 mol! 1
    A: the volume of sample taken for the assessment (mi)
    W: the weight of the sample taken for preparation (g).
    (3) Measurement of essential oil content
    To measure the content of essential oils in the composition, an apparatus was used that
    25 quantify essential oils. A round flask equipped with a condenser that can trap the essential oil with 100 ml of the liquid composition, 2 I of distilled water and boiling beads was charged; Atmospheric distillation was performed with heating at approximately 100 oC for one hour and the amount of the essential oil (mi) collected in the capture tube was measured to calculate the oil content
    essential.
    (4) Citroptene measurement
    (Preparation of samples for analysis)
    Samples were prepared for analysis by the following methods. First, they weighed
    5 10 g of the liquid composition in a centrifuge glass tube (A). Note that when the liquid composition had a Brix value of 10% or more, 5 g was weighed; in the case of 20% or more, 25 g were weighed; And in the case of 30% or more, 1 g was weighed; In any case, the heavy liquid composition was diluted to 10 ml with distilled water for liquid chromatography. Subsequently, 20 ml of ethanol was added to
    10 liquid chromatography and the mixture was vigorously stirred with a vortex mixer for a minute or more. When high viscosity prevented effective mixing, vigorously manual agitation was optionally performed. The intimate mixture was subjected to a centrifuge (1620 G x 30 min at 20 ° C) and the supernatant was transferred to another centrifuge glass tube (B). To the precipitate was added 20 ml of ethanol for chromatography of
    15 liquids and after breaking loose solids sufficiently with a suitable device such as a dispensing spoon, the mixture was vigorously stirred with a vortex mixer for a minute or more. After centrifugation with a centrifuge (1620 G x 30 min at 20 OC), the supernatant was loaded into the centrifuge tube (B). The supernatants collected in the centrifuge tube (B) were centrifuged
    20 additionally (1620 G x 30 min at 20 OC) And the resulting supernatant was transferred to a 50 ml volumetric flask and diluted with ethanol to the marked line. The well mixed supernatant was further diluted 10 times with ethanol for liquid chromatography and passed through a PTFE filter washed with preliminary ethanol (product of Toyo Roshi Kaisha, LTD; ADVANTEC DISMIC-25HP 25HP020AN, with a size of
    25 pore of 0.20 J.Jm and a diameter of 25 mm) to prepare samples for analysis.
    (Conditions for Cl separation)
    HPlC apparatus: Agilent 1290 series (product of Agilent technologies Inc .; equipped with feed pump, G4220A; automatic injector, G4226A (with thermostat G1330B); column oven, G1316C; and DAD detector, G4212A)
    30 Column: Phenomenex KINETEX C18 100A (particle size, 1, 3 ~ m; internal diameter, 2.1 mm x 50 mm x two columns coupled in series (product of Phenomenex Company)
    Mobile phase A: 0.1% aqueous solution of formic acid Mobile phase B: acetonitrile Flow rate: 0.4 ml / min Density gradient conditions: 0.0-1.0 min (5% B) _
    of B), with 4.5 min of equilibration by the initial mobile phase Column temperature: 40 oC Sample injection: injected in a volume of 1.0 ¡JI Sample load in the mass spectrometer: 2.0- 31, 99 min (Conditions for mass spectroscopy)
    29.5-31.5 min (100%
    10 Mass spectrometer: Q Exactive (product of Thermo Fisher Scientific Company) Ionization method: HESI, positive mode Ionization chamber conditions: Protective gas flow rate, 50; Auxiliary gas flow rate, 10;
    15 Flow rate of the scanning gas, O; Spray voltage, 2.50 kV; lempo of the capillary, 350 oC; Temp. of the auxiliary gas heater, 300 oC Detection conditions:
    20 Resolution, 70000; Objective of AGC, 1e6; Maximum IT, 100 ms; Scanning interval, 100 to 1000 miz Analysis condition:
    The detection time of the citroptene peak was 10.37 min in an ion chromatogram extracted for 207.0647-207.0667 ml. For each sample, an elution time must be confirmed using a standard sample.
    (Quantification method)
    Standard samples were purchased from Alfa Aesar Company. At least three were used
    5 standard sample solutions of different concentrations and quantification wereperformed by the absolute calibration method based on the areas of peaks obtained. Inthe case of the measurements that ended up giving values that were outside theCalibration curve intervals, the dilution factor with ethanol in the final stage ofsample preparation for analysis was appropriately adjusted to perform another
    10 measurement
    (5) Hesperidin measurement
    Samples were measured for analysis that were prepared by the same methods as theused for citroptene under the following conditions.(Conditions for Cl separation)
    15 HPLC device: Nexera XR series (product of Shimadzu Corporation; equipped with system controller, CBM-20A; feed pump, LC-20AOXR; in-line degasser, DGU-20A3; automatic injector, SIL-20ACXR; oven column, CTO-20A; and UVNlS detector, SPD-20A)
    Column: CAPCELL CORE AQ (particle size, 2, 7 ~ m; internal diameter, 2.1 mm x 20 150 mm; product of Shiseido Company, Limited) Mobile phase A: 0.1% aqueous solution of formic acid Phase mobile B: acetonitrile Flow rate: 0.6 ml min Density gradient conditions: 0.0-0.5 min (15% B) ~ 6.0 min (25% B), 25 with 10.0 min (75% of B) _ 10.1-11, 0 min (100% of B), with 3.0 min of equilibration by the initial mobile phase Column temperature: 40 oC Sample injection: injected in one volume 2.0 1-11 Sample load on the mass spectrometer: 1.8-11, 0 min
    (Conditions for mass spectroscopy)
    Mass spectrometer: 4000 Q TRAP (product of AB Sciex)
    Ionization method: ESI (Turbo Spray), negative mode
    Conditions of the ionization chamber: CUR, 10; IS, -4500; TEM, 650; GS1, 80; GS2, 5 60; hehe, ON; CAD, Medium
    Detection method: MRM mode
    Detection conditions: (Q1 ~ Q3, DP, CE, CXP, EP):
    Hesperidine (609.2 ~ 301, 1, 1, -76, -50, -11, -10)
    Peak detection time: Being subject to confirmation with standard samples, the following data can be given as a guide.
    Hesperidine (4.67 min)
    (Quantification method)
    Standard samples were purchased from Wako Pure Chemical Industries, You used at least three standard sample solutions of different concentrations and the
    The quantification was performed by the absolute calibration method based on the areas of peaks obtained. In the case of measurements that ended up giving values that were outside the ranges of the calibration curves, the dilution factor with ethanol in the final stage of sample preparation for analysis was properly adjusted to perform another measurement.
    20 (6) Routine measurement
    Samples were measured for analysis that were prepared by the same methods as those used for hesperidin under the following conditions.
    (Conditions for Cl separation): The same as for hesperidin is applicable.
    (Conditions for mass spectroscopy)
    25 Mass spectrometer: 4000 Q TRAP (product of AB Sciex)
    Ionization method: ESI (Turbo Spray), positive mode
    Conditions of the ionization chamber: CUR, 10; IS, 5500; TEM, 650; GS1, 80; GS2, 60; hehe, ON; CAD, Medium 17
    Detection method: MRM mode
    Detection conditions: (01 ~ 03, DP, CE, CXP, EP):
    Routine (611, 2 ~ 303.1, 76, 25, 12, 10)
    Peak detection time: Being subject to confirmation with standard samples, 5 the following data can be given as a guide.
    Routine (3.01 min)
    (Quantification method)
    Standard samples were purchased from Wako Pure Chemical Industries, You used at least three standard sample solutions of different concentrations and the
    The quantification was performed by the absolute calibration method based on the areas of peaks obtained. In the case of measurements that ended up giving values that were outside the ranges of the calibration curves, the dilution factor with ethanol in the final stage of sample preparation for analysis was properly adjusted to perform another measurement.
    15 <Example 1 gt;
    (1) Production of lemon aroma composition
    Lemon peel (FINE) was collected and most of the albedo was removed from the peel. During the collection of the shell and the removal of the albedo attention was paid to minimize the possible damage to the oil sacks in the shell. The flavedo of the remaining lemon 20 was mixed with water at a weight ratio of 1: 1 and the mixture was triturated with a commercial juice mixer, paying attention to ensure that the mixture did not have a paste-like consistency; After stirring at room temperature for 30 minutes, the mixture was passed through a 40 mesh strainer to effect solid-liquid separation. The liquid phase was then homogenized at 0.2 MPa 25 and the insoluble solids were removed from the resulting suspension by centrifugation (6000 G x 5 min) and then pasteurized by heating at 90 ° C for one minute in order to prepare a liquid composition (Product of the invention 1). The Product of the invention 1 was compared with three types of commercial crushed lemon juice (Comparative Examples 1-3) and the results are shown in Table 2 below. The
    30 various components were measured by the methods described above.
    (2) Sensory evaluation
    To Solutions adjusted with sucrose and citric acid anhydride to Brix 10 and 0.15% acidity, the Product of the invention 1 prepared above according to item was added
    (1) at a concentration of 10 g And then the sample was packaged in a bottle and pasteurized by heating at 85 oC for 5 minutes to produce a bottled beverage with lemon flavor. In addition, the following beverages were produced: a beverage containing Comparative Example 1 at a concentration of 2.4 gil, a beverage containing Comparative Example 2 at a concentration of 2.5 gil, and a beverage containing Comparative Example 3 at a concentration of 10 gil. The drinks obtained were evaluated with respect to their flavor. The flavors evaluated were the intensity of a natural fresh aroma and the intensity of a deteriorated smell, and the classification system was on a 5-point scale using the criteria shown in Table 1 below. The results are shown in Table 2. The Product of the invention 1, although subjected to a thermal pasteurization treatment, had a fresh and pleasant aroma that resembles that of before heating. The aroma was reminiscent of a natural fruit even though the sample did not contain fruit juice. On the other hand, in the commercial crushed juice (Comparative Examples 1-3), a characteristic smell of citrus fruit with high citrus aroma and acid taste was reduced and deteriorated. In addition, using the Product of the invention 1 stored in a refrigerator for a month, a lemon-flavored beverage was produced in the same method and evaluated for taste. The
    The beverage stably retained a characteristic citrus flavor with high citrus aroma and acidic taste after storage and hardly emitted a noticeable deteriorated smell.
    [Table 1)
    Punctuation Grade
    4 Intensely perceived
    3 Considerably perceived
    2 Moderately perceived
    one Slightly perceived
    OR Not perceived
    [Table 2) <Example 2gt;
    Product of the invention 1 Comparative Example 1Comparative Example 2Comparative Example 3
    Soluble solid content (Brix:%) 5.723.922.85.7
    Acidity (%) 0.6711, 58.62.4
    Essential oil content (%) 1.101.11.20.8
    Acid citroptene concentration (mg / kg / acid) 11.21.12.06.1
    Acid hesperid concentration due to acidity (mg / kg / acid) 430.359.063.3278.9
    Routine acidity concentration (mglkg / acid) 92.73.44.99.8
    Taste evaluation (Fresh aroma intensity) 422one
    Taste evaluation (Impaired smell intensity) °2one3
    Taste evaluation after storage (Intensity of fresh aroma) 4
    Taste evaluation after storage (Impaired smell intensity) one
    A liquid composition (Product of the invention 2) was obtained using the flavedo of the same lemon and the method as used to produce the Product of the invention 1 in Example 1, except that before mixing the flavedo with water the surface layer upper was removed by slicing the flavedo thin enough to not break the oil sacks in it. In the same methods described in Example 1, the liquid composition obtained was subjected to component measurement and the taste of the lemon-flavored drink produced was evaluated. The results are shown in Table 10 3, It turned out that, by removing the upper surface layer of the shell and then crushing the shell into the water (Product of the invention 2), the routine content could be significantly reduced compared to a case in which the upper surface layer was not removed (Product of the invention 1), The liquid composition in which the routine concentration was limited to be within a certain range not only had an aroma and flavor reminiscent of a natural fruit enhanced by citroptene and hesperidin, but also irritating bitterness was reduced that lasts a long time in the
    aftertaste and, therefore, was preferred. This preferable aroma and flavor was stably retained after storage.
    [Table 3)
    Product of the invention 1 Product of the invention 2
    Soluble solid content (Brix:%) 5.74.2
    Acidity (%) 0.670.38
    Essential oil content (%) 1.100.45
    Acid citroptene concentration (mglkgfácido) 11.28.7
    Hesperidin concentration by acidity (mglkgfácido) 430, 3602, 0
    Routine acidity concentration (mglkgfácido) 92.747.1
    5 <Example 3gt;
    Lemon aroma compositions were produced using a variety of lemons in the same method that is used to produce the Product of the invention 2 in Example 2. The liquid compositions obtained were subjected to the measurement of components and lemon-flavored beverages. produced were evaluated for their taste. The
    10 results are shown in Table 4. The Products of the invention 3-12 in which the acidity and concentration of citroptene, hesperidin and rutin were adjusted to be within certain intervals had a fresh and pleasant aroma characteristic of citrus with high citrus aroma and acid taste.
    [Table 4)
    Product of the invention 3 Product of the invention 4Product of the invention 5Product of the invention 6Product of the invention 7
    Soluble solid content (Brix:%) 4.84.64.14,54,5
    Acidity (%) 0.630.630.570.670.57
    Essential oil content (%) 0.700.650.450.550.80
    Acid citroptene concentration (mglkgfacid) 15.013.211, 15.57.9
    Hesperidin concentration by acidity (mglkgfácido) 482.8451, 9447.8350.4494.4
    Routine acidity concentration (mglkg / acid) 20, 719.818.611.418.4
    Product of the invention 8 Product of the invention 9Product of the invention 10Product of the invention 11Product of the invention 12
    Soluble solid content (Brix:%) 4.13.94, 13.94.2
    Acidity (%) 0.520.360.600.580.60
    Essential oil content (%) 0.450.450.400.380.50
    Acid citroptene concentration (mglkg / acid) 7.47.98, 79.27.1
    Acid hesperidin concentration (mglkg / acid) 588.2486.4602.0577.6545.6
    Routine acidity concentration (mglkg / acid) 17.339.047.117.213.9
    权利要求:
    Claims (5)
    [1]
    1. A liquid composition comprising an essential oil of the peel of a citrus fruit selected from the group consisting of lemon (Citrus limon), lime (Citrus aurantifolia), Citrus sudachi, Citrus sphaerocarpa, Citrus depressa and Citrus junos,
    5 citroptene and hesperidin,
    characterized in that the essential oil of the shell is contained in a range of 0.2-3.5%, by volume of the total amount of the composition;
    Citroptene is contained in a concentration with respect to acidity in a range of 5-20 mg / kg / acid; Y
    10 Hesperidin is contained in a concentration with respect to the acidity of 300 mg / kg / acid or more.
    [2]
    2. The liquid composition according to claim 1, wherein the citroptene and hesperidin are derived from the peel of one or more of the citrus fruits.
    [3]
    3. The liquid composition according to claim 1 or 2 further comprising routine, in a concentration with respect to acidity of 50 mg / kg / acid or less.
    [4]
    Four. The liquid composition according to claim 3, wherein the routine comes from the peel of one or more of the citrus fruits.
    [5]
    5. The liquid composition according to any one of claims 1 to 4 having an acidity of 2.0% or less.
    A beverage containing the liquid composition according to any one of claims 1 to 5 at a concentration in a range of 0.1-15% by weight based on the total weight of the beverage.
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    同族专利:
    公开号 | 公开日
    ES2757998T3|2020-05-04|
    ES2583162B1|2017-07-10|
    EP3272231A1|2018-01-24|
    JP6698627B2|2020-05-27|
    US20180055072A1|2018-03-01|
    EP3272231A4|2018-10-10|
    WO2016148149A1|2016-09-22|
    EP3272231B1|2019-11-13|
    JPWO2016148149A1|2018-01-18|
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    ES2466291T3|2005-07-27|2014-06-09|Symrise Ag|Use of hesperetin to enhance the sweet taste|
    US20100196549A1|2009-02-03|2010-08-05|Tropicana Products, Inc.|Microencapsulated citrus phytochemicals and application to sports drinks|
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    WO2007083812A1|2006-01-23|2007-07-26|Suntory Limited|Food or drink and method of producing the same|
    JP4838669B2|2006-09-04|2011-12-14|三井製糖株式会社|Flavor improving agent, flavor improving method using the same, and food and drink|
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    US20110158919A1|2009-12-30|2011-06-30|Symrise Ag|Aroma composition comprising o-coumaric acid to reduce or suppress undesirable taste impressions of sweeteners|JP6924069B2|2017-05-01|2021-08-25|サントリーホールディングス株式会社|Recovery of aroma components from citrus peel|
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    法律状态:
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    优先权:
    申请号 | 申请日 | 专利标题
    ES201530335A|ES2583162B1|2015-03-16|2015-03-16|Liquid compositions containing essential oils extracted from the citrus peel|ES201530335A| ES2583162B1|2015-03-16|2015-03-16|Liquid compositions containing essential oils extracted from the citrus peel|
    ES16764979T| ES2757998T3|2015-03-16|2016-03-15|Liquid composition containing essential oil of citrus peel|
    PCT/JP2016/058181| WO2016148149A1|2015-03-16|2016-03-15|Liquid composition containing citrus peel essential oil|
    US15/558,029| US20180055072A1|2015-03-16|2016-03-15|Liquid composition containing citrus peel essential oil|
    EP16764979.7A| EP3272231B1|2015-03-16|2016-03-15|Liquid composition containing citrus peel essential oil|
    JP2017506570A| JP6698627B2|2015-03-16|2016-03-15|Liquid composition containing essential oil of citrus peel|
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