JP5033080B2 - Taste improving agent - Google Patents

Description

The present invention relates to a taste improver, a flavoring composition, a food and drink containing these, and a method for improving taste.
More specifically, a taste improver characterized by comprising feruloyl putrescine, a flavor and flavor composition characterized by containing feruloyl putrescine, and containing the taste improver or flavor composition. The present invention relates to a method for improving the taste of foods and drinks, characterized by adding an effective amount of feruloyl putrescine.

Taste consists of the basic five tastes of sweet, sour, bitter, salty, and umami, and the taste of food and drink is comprehensively recognized as a mixture of complex tastes. In the case of improving the taste of food and drink, the simplest way is to increase or decrease the amount of taste substances that contribute to each taste. However, due to the recent increase in health consciousness, the use of sugars and salts tends to be reduced.
Also, depending on the type of tastant, the unpleasant taste derived from the substance may pose a problem, and the type and amount of tastant that can be used may be limited. Can be difficult to do.

  As a method for solving the above problems, for example, a method of improving the aftertaste of high sweetness amount by adding black tea leaf extract (Patent Document 1), a method of enhancing salty taste using spirrantol and Allium plant extract (Patent Document 1) Document 2), a method for enhancing the taste using a solvent extract of tea (Patent Document 3), and the like have been proposed. These are effective for the purpose of improving or enhancing a specific taste, but are not necessarily sufficient in terms of imparting a complex overall taste to food and drink.

  In the example which paid attention to the taste component contained in citrus, for example, a method (Patent Document 4) using a distillation residue of citrus cold press oil has been proposed. In addition, taste ingredients contained in citrus fruits include naringin and limonin, both of which have long been known as contributing components of bitterness characteristic of citrus fruits (for example, Non-Patent Document 1). However, bitterness may not be favorably accepted in the market.

In addition, from the viewpoint of improving the flavor of fruitless or low fruit juice beverages, the fruit juice contains glucan having an inner branched ring structure portion and an outer branch structure portion and a polymerization degree of 50 or more as an active ingredient. A fruit juice feeling improver (Patent Document 5) for containing foods and drinks, a method for enhancing the fruit juice feeling by adding Vicenin-2 (Patent Document 6), and the like have been proposed.
However, consumer preferences vary and there is a tendency to continually seek new things, so developing materials that have effects that cannot be expressed only with known ingredients and technologies will lead to a richer diet It was one of the propositions to be solved.
Japanese Patent Laid-Open No. 2007-14212 JP 2006-296357 A JP 2005-137286 A Japanese Patent Laid-Open No. 2003-299459 JP 2003-289836 A JP 2006-238829 A CITRUS SCIENCE AND TECHNOLOGY (THE AVI PUBLISHING COMPANY) 1977

  The problem to be solved by the present invention is a taste improver, a flavoring composition, a food and drink containing these, and a method for improving the taste of food and drink, which can impart a complex overall taste and fruit juice feeling to the food and drink. Is to provide

  As a result of fractionating and searching for various components contained in the fruit in order to solve the above problems, the present inventors surprisingly added a feruloyl putrescine contained in the fruit, thereby imparting a fruit juice feeling and taste. The present invention has been completed.

That is, the present invention is a taste improver characterized by comprising feruloyl putrescine, a taste improver composition characterized by containing feruloyl putrescine as an active ingredient, It is a flavoring composition characterized by containing Roylputrescine, more specifically, the flavoring composition characterized in that the content of Ferroylputrescine is 10 ² to 10 ⁵ ppm, It is a food or drink characterized by adding 10 ^-1 to 10 ² ppm of feruloyl putrescine, and is a food or drink characterized by adding the flavoring composition. It is a taste improvement method characterized by adding 10 ^-1 to 10 ² ppm of feruloyl putrescine to a no-fruit juice drink or a low fruit juice drink.

  The taste improver of the present invention can enhance the flavor by bringing a fruit-flavored food or drink containing no fruit juice or containing a low-concentration fruit juice closer to the taste of food or drink containing a high-concentration fruit juice. .

Hereinafter, the present invention will be specifically described.
[1] Feruloyl putrescine Feruloyl putrescine used for the taste improver of the present invention, that is, N- (4-aminobutyl) -4-hydroxy-3-methoxycinnamamide (N- (4-aminobutyl) ) -4-hydroxy-3-methoxycinnamamide) is a compound having a structure represented by the following chemical formula (1).
CAS number: 501-13-3
Composition formula: C ₁₄ H ₂₀ N ₂ O ₃
Molecular weight: 264.32

  Ferroyl putrescine is known to be contained in potato, dogwood, tobacco, corn, etc. in addition to citrus grapefruit and orange juice. Ferroyl putrescine is said to be involved in the regulation mechanism of ion concentration in plant cells. In addition, although there are reports on biological activities such as blood pressure lowering action and muscle contraction / relaxation action, the industrial use is unknown.

[2] Manufacture of Ferroyl Putrescine Derived from Natural Products When used in the present invention, any source can be used without problems as long as it is sufficiently purified. Further, even if feruloyl putrescine is not necessarily sufficiently purified, it may be economically advantageous to use it as a crude product as long as it has a taste improving effect. When feruloyl putrescine is used in the form of a crude product, it is desirable to isolate the raw material from edible foods, that is, citrus fruits, specifically orange or grapefruit juice or peel. There are no particular restrictions on the method of purification or isolation, and various known methods can be used depending on the purpose.

(1) Extraction Specifically, an orange or grapefruit juice or peel is first extracted with water or a water-soluble solvent to obtain an extract. Examples of the water-soluble solvent include solvents such as methanol, ethanol, 2-propanol, and acetone. One or a mixture of two or more of these can be used, and they are used in the form of an aqueous solution as necessary.

  The solvent used for extraction is preferably an aliphatic alcohol having 2 to 4 carbon atoms such as ethanol, propanol, or butanol from the viewpoint of safety to the human body and handleability, and ethanol is most preferable. Preferably, an ethanol 40 to 80% (V / V%, hereinafter the same) aqueous solution, more preferably a 50 to 60% aqueous solution is used. Although the quantity of the solvent used for extraction can be selected arbitrarily, generally about 5-30 times is used by mass with respect to a citrus raw material, Preferably 10-15 times is used. The temperature and time of extraction can be arbitrarily determined, and are not particularly limited, but several hours, preferably about 1 to 3 hours are suitable at around room temperature.

  By sequentially purifying the obtained extract with a cation exchange resin and a synthetic adsorption resin, it is possible to obtain a taste improver comprising feruloyl putrescine from which unnecessary flavor components have been removed.

(2) Separation of fractions containing feruloyl putrescine by cation exchange resin An ion exchange resin (ion exchanger) is obtained by introducing an ion exchange group into a support called a carrier. The type of the resin is an ion exchange capacity of 80 to 200 g Ca / -resin, the degree of crosslinking is about 8 to 20%, the particle size is 0.60 to 0.80 mm, and the resin structure is a gel type or a porous type. It can be used, and is not particularly limited by the carrier (styrene polymer, methacrylic acid resin, silica gel, cellulose, dextran, etc.) or exchange group (sulfone group, carboxyl group), but among them strong acid cation exchange resin, For example, “Amberlite (registered trademark) having a styrene resin such as a styrene-divinylbenzene copolymer as a carrier and a sulfonic acid group as an exchange group. 200CT ", etc. (Rohm & Haas Co., Ltd.) and" Diaion (R) SK1B "(produced by Mitsubishi Chemical Co., Ltd.) may be mentioned as suitable.

  The treatment method of the cation exchange resin in the present invention may be performed by a conventional method, for example, a method in which a citrus extract is brought into contact with a cation exchange resin packed in a column at a constant flow rate, or an extraction kettle is charged. There is a method in which a cation exchange resin is added to the extract and the cation exchange resin is separated after stirring for a certain period of time, and can be appropriately selected depending on the purpose. However, it is usually more efficient to use a column.

  The basic substance including feruloyl putrescine exchanged on the cation exchange resin is eluted from the resin according to a conventional method. That is, the basic fraction containing feruloyl putrescine can be eluted by bringing an arbitrary aqueous inorganic salt solution into contact with the cation exchange resin. The type and concentration of the inorganic salt (specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium chloride, potassium chloride, etc.) and concentration may be selected according to the purpose, and there are no particular restrictions. When a sodium hydroxide aqueous solution of about 5 to 2.0 mol / L is used, the recovery rate is good.

(3) Desalination treatment of feruloyl putrescine-containing eluate The eluate of the basic fraction containing feruloyl putrescine obtained by treatment with an ion exchanger is a large amount derived from the aqueous inorganic salt solution used in the aforementioned elution. This salt is then subjected to a desalting treatment with a synthetic adsorption resin.
The synthetic adsorption resin used in the present invention is not particularly limited in terms of the base structure, specific surface area, average pore diameter and the like, but those exemplified below can be used.
That is, the matrix is styrene, for example, “Amberlite (registered trademark) XAD-16” (manufactured by Organo Corporation), styrene-divinylbenzene, for example, “Separbeads (registered trademark) SP700” (produced by Mitsubishi Chemical Corporation), methacrylic For example, “Diaion (registered trademark) HP2MG” (manufactured by Mitsubishi Chemical Corporation) can be used.

  Further, the synthetic adsorption resin treatment method in the present invention may be performed by a conventional method. For example, a method in which a synthetic adsorption resin packed in a column is contacted with an eluate containing feruloyl putrescine at a constant flow rate, There is a method in which a synthetic adsorption resin is added to an eluate containing feruloyl putrescine charged in 1 and the synthetic adsorption resin is separated after stirring for a certain period of time. There is no particular restriction on the method, and it can be selected according to the purpose. The basic substance containing feruloyl putrescine adsorbed on the synthetic adsorption resin can be eluted with various organic solvents, for example, organic solvents such as methanol, ethanol, 2-propanol and acetone, or these aqueous solutions as required. . The solvent used for elution is most preferably ethanol or an aqueous solution thereof from the viewpoint of safety to the human body and handleability.

  The taste improving agent of the present invention can be used as it is the desalted feruloyl putrescine-containing eluate in the previous paragraph, but the eluate as a concentrate by means of vacuum distillation concentration or membrane concentration, Alternatively, it can be used after being pulverized by freeze-drying or the like.

  Furthermore, the feruloyl putrescine purified product thus obtained can be further filtered, concentrated, deodorized with activated carbon, decolorized, liquid-liquid distribution, reverse phase chromatography, normal phase chromatography, gel filtration chromatography, It can be purified by known techniques such as crystallization.

[3] Production of feruloyl putrescine by chemical synthesis The feruloyl putrescine of the present invention can also be obtained by chemical synthesis. There is no restriction | limiting in particular in a synthetic | combination route or the solvent or reagent to be used, It can select arbitrarily. Most simply, it can be obtained by dehydration condensation of ferulic acid and 1,4-diaminobutane. However, it may be subjected to a protection or deprotection step, or a different starting material may be used depending on the purpose. I can do it.

[4] Taste improving agent composition and taste improving method The taste improving agent of the present invention further includes food additives such as sweeteners, coloring agents, preservatives, thickening stabilizers, antioxidants, bittering agents, An acidulant, an emulsifier, a strengthening agent, a production agent, a fragrance and the like can be added and used as various preparations, and it is particularly preferable to use as a flavor composition.

When feruloyl putrescine or a purified product thereof, or a preparation thereof is added to food or drink, it is desirable that the added amount be added as feruloyl putrescine at a concentration of 10 ⁻¹ to 10 ² ppm, and it is used particularly effectively. Therefore, it is preferable to add at a concentration of 1 to 50 ppm. When added at such a concentration, feruloyl putrescine is contained in the flavoring composition at a constant concentration, and it is excellent in usability to add the flavoring composition. This is particularly effective when the composition is a fruit flavoring composition. When feruloyl putrescine is contained in the flavoring composition, its concentration is suitably 10 ² to 10 ⁵ ppm, and 10 ³ to 10 ⁵ ppm in order to exhibit the effects of the present invention more effectively. A concentration is more preferred.

  The taste improving agent of the present invention can be used for food and drink in general, and the food and drink referred to in the present invention refers to foods, drinks, spices, seasonings, pharmaceuticals and the like that can be used for food and drink. Since the effect of the present invention is most effective when imparting a fruit juice sensation, the present invention is effective for a fruit juice-flavored food and drink, particularly a fruit juice-flavored food or drink with no fruit juice or low fruit juice. Examples of the juice include fruitless-flavored or low-fruit juice drinks, carbonated drinks, soft drinks, functional drinks, and alcoholic drinks.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.

[Example 1] Production of feruloyl putrescine by chemical synthesis 150 mL of tetrahydrofuran was weighed into a 500 mL round bottom flask, and 12.7 g (65.4 mmol) of ferulic acid, t-butyl N- (4-aminobutyl) carbamate, 11. 1 g (59.0 mmol), 17.5 g (129.5 mmol) of 1-hydroxybenzotriazole, and 6.6 g (65.2 mmol) of triethylamine were dissolved in that order and cooled to 0 ° C. with ice water. 100 mL of a dichloromethane solution of 10.8 g (56.3 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride was added, and the mixture was warmed to room temperature and stirred overnight. The reaction solution was cooled to 0 ° C., and then washed successively with 300 mL of 5% aqueous citric acid solution and saturated aqueous sodium hydrogen carbonate solution using a separatory funnel. After drying the organic layer with anhydrous sodium sulfate, the organic solvent was distilled off under reduced pressure to obtain 25.5 g (crude yield 90%) of the amide compound represented by the chemical formula (2).

  25.5 g of the amide crude purified product represented by the chemical formula (2) was weighed into an eggplant type flask, 200 mL of 3 mol / L hydrogen chloride aqueous solution and 50 mL of ethanol were added, and the mixture was stirred overnight at room temperature for deprotection. The reaction solution was cooled to 0 ° C., neutralized with an aqueous sodium hydroxide solution, and then concentrated using an evaporator.

The concentrated solution obtained was adjusted to about pH 3 using a 1 mol / L aqueous solution of hydrogen chloride and filled with 50 mL of a strongly acidic cation exchange resin (“200CT” described above) whose exchange group is a sulfonic acid group (—SO ₃ H). The column was passed with SV (space velocity) = 2. Subsequently, the resin-filled portion was washed with 200 mL of ion exchange water, and then 500 mL of a 1 mol / L sodium hydroxide aqueous solution was passed through at SV = 3 to elute feruloyl putrescine.

  The obtained feruloyl putrescine eluate was desalted by passing it through a column packed with 50 mL of a synthetic adsorption resin (described above “SP700”) at SV = 3. The resin-filled part was washed with 200 mL of ion-exchanged water, and then the basic fraction containing feruloyl putrescine was eluted with 500 mL of 95% ethanol. After distilling off ethanol under reduced pressure, the obtained concentrate was suspended in distilled water and freeze-dried, and 11.8 g (44.7 mmol) of feruloyl putrescine was obtained as N- (4-amino) as yellow powdery crystals. (Butyl) was obtained in 76% yield from t-butyl carbamate.

  Proton and carbon-13 nuclear magnetic resonance spectra of the obtained feruloyl putrescine were measured. For measurement, “AVANCE400 (trade name)” manufactured by Bruker BioSpin Co., Ltd. was used, the magnetic field strength was 400 MHz (100 MHz when measuring carbon 13 nuclear magnetic resonance spectrum), the solvent was deuterated methanol, and the measurement temperature was 27 ° C. Spectral data was represented by δ: ppm, and the signal shape was represented by s for a single line, d for a double line, t for a triple line, and m for a multiple line. Coupling constant J: Expressed in Hz, and the signal proton number was described as XH (X represents the proton number).

  The proton nuclear magnetic resonance spectrum is shown below. δ7.76 (d, J = 16 Hz, 1H), δ7.72 (d, J = 2 Hz, 1H), δ7.04 (dd, J = 8.4 Hz, 2 Hz, 1H), δ6.81 (d, J = 8.4 Hz, 1 H), δ 6.43 (d, J = 16 Hz, 1 H), δ 3.43 (t, J = 6.4 Hz, 2 H), δ 2.97 (t, 7.2 Hz, 2 H), δ 1 .66 (m, 4H)

  The carbon 13 nuclear magnetic resonance spectrum is shown below. δ 169.4, 150.5, 149.3, 142.3, 128.2, 123.2, 118.6, 116.5, 111.6, 56.4, 40.4, 39.6, 27. 6, 25.9

[Example 2] Manufacture of feruloyl putrescine derived from natural products About 300 g of frozen Valencia orange peel was subjected to freeze-drying to obtain 80 g of dried peel, which was then pulverized into powder. 800 g of 50% ethanol aqueous solution was added, and the mixture was extracted by stirring at 25 ° C. for 1 hour. Insoluble matter was separated by centrifugation (3000 rpm, 20 minutes, 5 ° C.) to obtain 567 g of an extract.

The obtained extract was concentrated to about 200 mL under reduced pressure, and then SV (space) was applied to a column packed with 50 mL of a cation exchange resin (the above-mentioned “200CT”) in which the exchange group is a sulfonic acid group (—SO ₃ H). Speed) = 2. Subsequently, the resin-filled portion was washed with 200 mL of ion-exchanged water, and then 500 mL of a 1 mol / L sodium hydroxide aqueous solution was passed at SV = 3 to elute the feruloyl putrescine fraction.

  The obtained feruloyl putrescine extract fraction eluate was desalted by passing it through a column packed with 50 mL of a synthetic adsorption resin (described above “SP700”) at SV = 3. The resin-filled part was washed with 200 mL of ion-exchanged water, and then the basic fraction containing feruloyl putrescine was eluted with 500 mL of 95% ethanol. After distilling off ethanol under reduced pressure, the obtained concentrate was suspended in distilled water and subjected to lyophilization, and 0.15 g of purified feruloyl putrescine was obtained from Valencia orange dried peel with a yield of 0.2%. .

[Test Example 1] Grapefruit flavored beverage 6 parts by weight of granulated sugar and 0.1 part by weight of citric acid were dissolved in 100 parts by weight of ion-exchanged water, and 5 ppm of grapefruit flavor (Ogawa Fragrance Co., Ltd.) was obtained. A sample to which 10 ppm of feruloyl putrescine was added was used as an evaluation sample. A control without feruloyl putrescine was prepared as a control. Moreover, what added the same amount of Vicenin-2 which is a prior art as positive control was also evaluated simultaneously. Five trained panels gave a 7-point score for each indicator. For each item of sweetness, sourness, bitterness, fruit juice, and taste, a 7-point evaluation was performed with 4 points of control. The higher the score, the higher the effect.
Here, “feeling of fruit juice” means an image of citrus fruits such as juicy and fruity, and “taste” means a feeling of volume remaining in taste (the same applies to Test Example 2 described later).
The results are shown in Table 1, and the flavor comments are shown in Table 2.

  As shown above, it was shown that the addition of the taste improver of the present invention gives the grapefruit beverage a comprehensive taste including sweetness, sourness and bitterness, and can further impart a fruit juice sensation. Moreover, it was found that, compared with the conventional technique Bisenin-2, the acidity was suppressed and the sweetness was enhanced to have a well-balanced taste improving effect. Moreover, the taste and odor by addition of the taste improving agent of this invention were not felt.

[Test Example 2] Low juice orange beverage A commercially available low juice orange beverage (containing 20% orange juice) was prepared by adding 10 ppm of feruloyl putrescine obtained in Example 1 and used as an evaluation sample. As a control, a taste-improving agent of the present invention was added. As a positive control, the same amount of the conventional technique Vicenin-2 was also evaluated.
Five trained panels gave a 7-point score for each indicator. For each item of sweetness, sourness, bitterness, fruit juice, and taste, a 7-point evaluation was performed with 4 points of control. The higher the score, the higher the effect.
The results are shown in Table 3.

  As shown above, it was found that the addition of the taste improver of the present invention imparts taste to a low fruit juice beverage and gives a fruit juice feeling. In addition, the taste and odor due to the addition of the taste improver of the present invention were not felt, and a natural and well-balanced taste improvement effect was exhibited.

  The taste improver of the present invention, when added to food and drink, strengthens the taste of food and drink, and has the effect of changing the taste of food and drink to more complex and preferred, and is widely used in various foods and drinks. it can.

Claims (7)

  A taste improver comprising feruloyl putrescine.   A taste improver composition comprising feruloyl putrescine as an active ingredient.   A flavor composition comprising the taste improver composition according to claim 2. The flavor composition according to claim 3, wherein the content of feruloyl putrescine is 10 ² to 10 ⁵ ppm. A fruit juice-flavored fruitless beverage characterized by adding 10 ^-1 to 10 ² ppm of feruloyl putrescine . A fruit juice-flavored fruitless beverage, wherein the flavoring composition according to claim 3 or 4 is added. A method for improving taste, which comprises adding 10 ^-1 to 10 ² ppm of feruloyl putrescine to a fruit juice-flavored non-fruit juice drink or a low fruit juice drink.