JP2005269908A - Flavor deterioration inhibitor - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a flavor deterioration inhibitor having excellent safety, and giving no affection to the original flavor of food and drink, oral health agents, or the like; namely, a flavor deterioration inhibitor inhibiting flavor deterioration caused mainly by light, heat or oxygen in respective steps of production, distribution and storage. <P>SOLUTION: This flavor deterioration inhibitor comprises an extract from Syzygium malaccense Merr. et Perry and/or Euphoria longana Steud. seeds. The flavor deterioration inhibitor is added to food and drink, oral health agents or spices to inhibit flavor deterioration caused by light or oxidization. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a flavor degradation inhibitor and a flavor degradation inhibition method derived from a specific natural product that can be widely applied to foods and drinks, oral hygiene agents, pharmaceuticals or flavorings containing a flavor component.

  The taste and scent of beverages, foods, toothpastes, oral hygiene agents such as bad breath odors, and oral medicines (hereinafter also referred to as “food and beverages”) are felt as soon as they enter the mouth. The flavor of food and drink is an important element as well as various nutritional components. It is well known that flavors of such foods and beverages gradually deteriorate at each stage of production, distribution, storage and the like. Degradation of flavors of foods and drinks, etc., the flavor components themselves change due to oxygen, light, heat, etc., each component other than flavor components such as fats and oils, proteins, sugars, amino acids, organic acids contained in foods and drinks is oxygen, It is also caused by the occurrence of an off-flavor component by causing a number of reactions such as oxidation, reduction, isomerization, and polymerization by the action of light, heat, and the like. Recently, light-up packaging materials such as transparent glass containers and translucent plastic containers are often used for foods and drinks, etc., in order to improve the product image at storefront displays. Since the sales form to be displayed below is common, food and drink are more likely to cause flavor deterioration due to light than before.

  In order to suppress such deterioration of flavor, a method of adding various antioxidants such as ascorbic acid and photodegradation inhibitors such as chlorogenic acid and rutin has been proposed (Non-patent Document 1). The present inventors have also added extracts of plants such as eucalyptus, peppermint, cacao, and ashitaba, and naturally derived ingredients such as catechins for the suppression of flavor deterioration of foods and drinks due to light and heat. Has proposed a method for suppressing the deterioration of flavor by the use of the above (Patent Documents 1 to 13).

  However, as described above, the deterioration of flavors of foods and drinks, etc., in addition to the flavor components themselves changing due to oxygen, light, heat, etc., fats and oils, proteins, sugars, amino acids, organic acids, etc. contained in foods and drinks, etc. It is also caused by complex factors involved. For this reason, even if it uses the said prior art, an effect may still be inadequate, and the more highly effective flavor deterioration suppression technique was calculated | required.

“Patent Office Gazette, Well-known and conventional technology collection (fragrance) part 1”, January 29, 1999, pages 141 to 147 JP-A-11-137224 JP-A-11-169148 JP 2001-346558 A Japanese Patent Laid-Open No. 2002-244 JP 2002-330741 A JP 2003-79335 A JP 2004-16056 A JP 2004-16057 A JP 2004-16058 A JP 2004-16059 A JP 2004-16061 A JP 2004-18611 A JP 2004-18612 A

  The problem to be solved by the present invention is to provide a flavor deterioration inhibitor that is more effective than the prior art against flavor deterioration of food and drink caused by complicated factors.

  As a result of intensive investigations on the flavor deterioration-inhibiting activity of a variety of natural product-derived components, mainly plants, the present inventors have found that the extract of the seeds of the genus Marphiidae, the seeds of the genus Pleurotus genus, the seeds of the genus Lepidoptera It has been found that the use of odor suppresses flavor deterioration of foods and drinks caused by light, heat, oxygen, etc. for a long period of time, and the present invention has been completed.

  That is, the present invention is a flavor deterioration inhibitor characterized by containing a solvent extract of male white peach seeds and / or longan seeds. The present invention further includes foods and drinks to which the above flavor deterioration inhibitor is added in an amount of 0.5 to 500 ppm. Furthermore, this invention is a method of adding 0.5-500 ppm of the said flavor degradation inhibitor to food-drinks etc., and suppressing flavor degradation. Moreover, this invention is a flavorant formed by adding 0.005-5 mass% of said flavor degradation inhibitors. Furthermore, this invention is a method of adding 0.005-5 mass% of said flavor degradation inhibitors to a flavoring agent, and suppressing degradation.

By adding the flavor deterioration inhibitor of the present invention to foods and drinks and flavors, flavor deterioration can be suppressed for those that are susceptible to light, heat, oxygen, and the like. Especially for light, it has a remarkable effect of suppressing deterioration and can retain its flavor for a long time. Therefore, food and drink filled in transparent glass containers, translucent plastic containers, or transparent bags that are easily affected by light irradiation. If applied to products, excellent effects are exhibited. Moreover, since this flavor deterioration inhibitor is stable to heat and safe, it can be applied to various processed foods and beverages.
Since the flavor / odor of the flavor deterioration inhibitor of the present invention itself does not affect the original flavor of food and drink, it can be widely applied.

Hereinafter, the present invention will be described in more detail.
(1) Raw materials The male yellow peach (scientific name: Syzygium malaccensis) used in the present invention is an evergreen tree that belongs to the genus Myrtaceae that is widely distributed from India to East Polynesia. Has been. Longan (scientific name: Euphoria longana) is an evergreen Takagi of Mucuridae native to South Asia, and is eaten as raw canned food or processed canned and dried fruit mainly in southern China and Taiwan. In the present invention, male peach or longan seeds are used. Both male peach and longan seeds are known to be used as folk medicines against fever, but it is not known at all that these solvent extracts have an effect of inhibiting flavor deterioration. In the present invention, it is preferable to extract only seeds from the fruit of male peach or longan and subject to the extraction treatment described later, but the effect of the present invention can be exhibited even when the fruit containing the seeds is subjected to the extraction treatment as it is.

(2) Extraction treatment 1) Extraction solvent The solvent used for the extraction treatment is preferably water or an organic solvent, but is not limited thereto, and may be a supercritical fluid such as supercritical carbon dioxide. The organic solvent may be a hydrate. There is no restriction | limiting in particular as an organic solvent, Alcohols, such as methanol, ethanol, propanol, propylene glycol, Ketones, such as acetone, Esters, such as ethyl acetate, Ethers, such as diethyl ether, Hydrocarbons, such as hexane and heptane Can be used alone or in combination as appropriate. Polar organic solvents such as alcohols are preferred, and 50 to 95% ethanol is particularly preferred.
Although the amount of the solvent used for extraction can be arbitrarily selected, it is generally preferable to use 1 to 100 parts by weight of the solvent with respect to 1 part by weight of the raw material.

2) Extraction treatment method As the extraction treatment method, various methods can be adopted depending on the type and amount of the solvent. For example, pulverized various natural products can be put in a solvent and extracted by a dipping method or a heating reflux method. In the case of the immersion method, any of heating conditions, room temperature, or cooling conditions may be used.
Next, the solid solution insoluble in the solvent is removed to obtain an extract. As the solid material removal method, various solid-liquid separation means such as centrifugation, filtration, and pressing can be used.
The obtained extract can be used as it is as a flavor deterioration inhibitor, but may be appropriately diluted with a liquid diluent such as water, ethanol, glycerin, triethyl citrate, dipropylene glycol, or propylene glycol. Alternatively, dextrin, sucrose, pectin, chitin and the like can be added. These may be further concentrated to obtain a paste-like extract, or may be used as a powder after treatment such as freeze drying or spray drying.

3) Purification Although the extract obtained by the above method can be directly blended into foods and drinks, it can be further subjected to purification treatment such as decolorization and deodorization. For the purification treatment, activated carbon or a synthetic resin adsorbent made of porous styrene-divinylbenzene copolymer can be used. As the synthetic resin adsorbent for purification, for example, “Diaion HP-20 (trade name)” manufactured by Mitsubishi Chemical Corporation or “Amberlite XAD-2 (trade name)” manufactured by Organo Corporation can be used.

(3) Preparation of flavor deterioration inhibitor The extract obtained by the above purification treatment can be directly blended with food and drink, etc., but the flavor deterioration inhibitor is prepared from the extract obtained as described above as a raw material. It can also be used as a formulation. For example, dissolved in an appropriate concentration in a (mixed) solvent such as water, alcohol, glycerin, propylene glycol (specifically, a mixed solvent of water / ethanol, water / ethanol / glycerin, water / glycerin, etc.) To do. Alternatively, dextrin, sucrose, pectin, chitin and the like can be added, and these can be further concentrated to form a paste-form preparation. It is also possible to add excipients (such as dextrin) to each solution and form a powdery formulation by spray drying. Furthermore, an oil-soluble liquid agent can be obtained by adding and dispersing the liquid agent together with an emulsifier in an oil or the like, and various dosage forms can be adopted depending on the application.

(4) Usage The flavor deterioration inhibitor of the present invention can be appropriately added at the processing stage of food and drink. The amount of addition differs somewhat depending on the concentration of the inhibitor or the type of flavor component contained in the food or drink, or the flavor threshold, but generally the additive amount of 0.5 to 500 ppm relative to the food or drink (extract) As a solid component). From the viewpoint of adding within the range of the threshold value that does not affect the original flavor of food and drink, etc., 0.5 to 200 ppm is preferable, and 1 to 100 ppm is particularly preferable. On the other hand, when using the flavor deterioration inhibitor of this invention for a flavoring agent, 0.005-5 mass% is suitable, and 0.005-2 from a viewpoint added within the range which does not affect an original flavor. % By mass is preferable, and 0.01 to 1% by mass is particularly preferable.
In addition, the flavor deterioration inhibitor of the present invention may be used in combination with commonly used antioxidants such as L-ascorbic acid, green tea extract, rutin and the like, and photodegradation inhibitors, etc. There are no particular restrictions on the type and mixing ratio. About the addition amount of the mixed flavor degradation inhibitor, although it changes with the purity of the component of the inhibitor to be used, or the kind of the product of addition object, 0.5-500 ppm is suitable with respect to food-drinks, etc. A range of 1 to 100 ppm is preferred. On the other hand, 0.005-5 mass% is suitable with respect to a flavoring agent, and the range of 0.01-1 mass% is especially preferable.

Although the deterioration inhibitor of this invention can be used for food / beverage products etc. and a flavor without a restriction | limiting in particular, The following are mentioned as a specific example.
Examples of foods and drinks include beverages, confectionery, fats and oils and processed foods, milk, dairy products, oral hygiene agents, pharmaceuticals, etc. Perfume (2000) "p4-5), and more specifically, the following can be mentioned.
Examples of drinks include coffee, tea, soft drinks, lactic acid bacteria drinks, fruitless drinks, fruit juices, fruit drinks, and nutritional drinks.
Examples of confectionery include jelly, pudding, bavaria, candy, biscuits, cookies, chocolate, cakes, frozen desserts (ice cream, ice candy, etc.), chickenpox, gum and the like.
Examples of fats and oils and processed foods include edible fats and oils (animal fats and oils, vegetable fats and oils), margarine, shortening, mayonnaise, dressing, hard butter, etc., and instant noodles and tofu fried (fried, fresh, Ganmodoki), fried kamaboko, tempura, fries, snacks (potato chips, fried potatoes, karinto, donuts), cooked frozen foods (frozen croquettes, fried shrimp, etc.).
Examples of milk, dairy products, etc. include raw milk, cow milk, processed milk, etc., milk as cream, butter, butter oil, concentrated whey, cheese, ice cream, yogurt, condensed milk, powdered milk, concentrated milk, etc. Can be mentioned.
Examples of oral hygiene agents include toothpastes, mouthwashes, mouth fresheners, bad breath odor prevention agents, and the like.
Examples of pharmaceuticals include oral medications.

  Examples of flavors can be used for all flavors described in “Patent Office Gazette, Well-known and Conventional Techniques (Fragrance) Part 2 Food Fragrances (2000)”. Specifically, flavoring materials (essential oils, essences) Concrete, absolute, extract, oleoresin, resinoid, recovered flavor, carbon dioxide extracted essential oil, synthetic fragrance) and fragrance compositions containing them.

  EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is not limited to these Examples.

[Extraction Example 1]
After seeding seeds of Indonesian male peach (Syzygium malaccensis) fruit, 1 L of 50% ethanol was added to 100 g of this pulverized powder, followed by heating under reflux for 1 hour. Subsequently, after cooling, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure using a rotary evaporator and dried to obtain 8.37 g of male peach seed extract.

[Extraction Example 2]
100 g of fruit containing seeds of Indonesian male peach (Syzygium malaccensis) was added to 1 L of 95% alcohol and pulverized, followed by heating and reflux extraction for 1 hour. Subsequently, after cooling, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure and dried to dryness using a rotary evaporator to obtain 6.4 g of male peach fruit extract.

[Extraction Example 3]
The seeds of Indonesian Euphoria longana fruit were dried and pulverized, and 1 L of 50% ethanol was added to 100 g of the pulverized powder, followed by heating under reflux for 1 hour. Subsequently, after cooling, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure using a rotary evaporator and dried to obtain 22.6 g of longan seed extract.

[Extraction Example 4]
In order to obtain an active fraction, 5 g of the extract of Extraction Example 1 was dispersed in water and led to a column filled with 1000 mL of a synthetic adsorbent (Diaion HP-20), and sequentially with water, 50% ethanol, and ethanol each 1000 mL. Elution was carried out, and each fraction was concentrated and freeze-dried to obtain 2.3 g of water fraction, 2.4 g of 50% ethanol fraction and 0.2 g of ethanol fraction, respectively.

[Test Example 1]
Each extract of the present invention and existing antioxidants under general oxidation conditions using the reagent 2,2-diphenyl-1-picrylhydrazyl (DPPH) used in food oxidation tests as follows Comparison of antioxidant power with tocopherol.
In this test, DPPH radicals are erased by antioxidants. When subjected to antioxidant action, the purple color of DPPH changes to colorless. It is an indicator.
50% ethanol solution (2.0 mL) of each test substance and 2 × 10 ⁻⁴ M DPPH (Nacalai Tesque) ethanol solution (1) in 0.1 M acetate buffer (pH 5.5, 2.0 mL) 0.0 mL) to a total volume of 5.0 mL, and after 30 minutes, the absorbance at 517 nm was measured. The results were expressed as the test substance concentration (final solution) required to reduce the absorbance to ½ with respect to the control with no test substance added.

[Table 1]
Table 1 Test substance concentration of DPPH radical scavenging activity test (ppm)
1 Extraction Example 1 4.0
2 Extraction Example 2 35.5
3 Extraction Example 3 5.2
4 Chlorogenic acid 6.3

As shown in Table 1, under general oxidation conditions, each extract of the present invention and chlorogenic acid are almost equivalent in antioxidant power.

[Test Example 2]
Citral, a flavor component peculiar to citrus fruits, was added to 0.1 M citrate buffer (pH 3.5) so as to be 10 ppm, and the extract obtained in Extraction Examples 1 to 4 and L-ascorbic acid were added to this solution. Those added with 100 ppm and those added with nothing were put in transparent glass containers, respectively, and irradiated with light using a light stability tester (“LSR-300 type” manufactured by Tokyo Rika Kikai Co., Ltd.). Irradiation conditions were a temperature of 10 ° C., a white fluorescent lamp 40 W × 15, adjusted to 15000 lux, and irradiated for 2 weeks.
After irradiation, the buffer solution was extracted with dichloromethane, dried and concentrated, and the residual amount of citral in the buffer solution was measured by gas chromatography (GC). The results are shown in Table 2. The measurement conditions are as follows.

Measurement condition equipment: HP5890 SERIES II
Column: DB-wax (0.25mm id x 30m, film thickness 0.25μm)
Oven temp .: 80 ℃ -210 ℃, 3 ℃ / min
Injection: 250 ° C, Split ratio 100: 1
Detector: 250 ℃, FID

The citral residual rate (%) in Table 2 was calculated according to the following formula.
Citral residual rate (%) = C / D x 100
Where C: Citral content in the sample after light irradiation
D: Citral content in the sample before light irradiation

[Table 2]
Citral residual amount test Flavor degradation inhibitor (added amount: 100 ppm) Citral residual rate (%)
Additive-free 45.6
L-ascorbic acid 46.0
Extraction Example 1 75.9
Extraction Example 2 55.0
Extraction Example 3 60.1

  As shown in the table, the addition of the flavor deterioration inhibitor strongly suppressed the decrease in citral due to light irradiation, compared to the additive-free and L-ascorbic acid-added ones. Further, in view of the results of the test antioxidant test, each extract of the present invention has an antioxidant power equivalent to that of a conventional antioxidant, and is further excellent in preventing flavor deterioration of food due to light and heat. Is clear.

Next, the flavor deterioration inhibitor obtained by the above extraction was added to various foods for evaluation.
[Test Example 3] (yogurt drink)
94 g of milk and 6 g of skim milk powder were mixed and then sterilized (90 to 95 ° C., 5 minutes). After cooling to 48 ° C., a starter (lactic acid bacterium) was inoculated. This was put into a glass container and fermented (40 ° C., 4 hours, pH 4.5). After cooling, it was stored at 5 ° C. and used as a yogurt base. On the other hand, as the sugar solution, 20 g of sucrose, 1 g of pectin, and 79 g of water were mixed, heated at 90 to 95 ° C. for 5 minutes, and filled with a hot pack. 60 g of the yogurt base, 40 g of sugar solution, and 0.1 g of fragrance were mixed, and this was subjected to a homomixer treatment and a homogenizer treatment. A semi-transparent plastic container was filled with a product to which no flavor deterioration inhibitor was added and a product to which 10 ppm of flavor deterioration inhibitor was added. Each was put in a photostability tester and irradiated with a fluorescent lamp (6000 lux, 10 ° C., 5 hours), and 10 skilled panelists were selected for sensory evaluation. In this case, as a control having no change in flavor, a yogurt beverage not irradiated with a fluorescent lamp to which no flavor deterioration inhibitor was added was used, and the degree of change (deterioration) in flavor was evaluated. The results are shown in Table 3. In addition, the score of evaluation in Table 3 is an average score of each panel scored according to the following criteria. Also, the off-flavors and off-flavors in the scoring standards refer to “metal odor”, “pickled odor”, and “degraded odor of oil”.
(Scoring criteria)
Strong taste and smell: 4 points Flavor changed very much: 3 points Flavor changed: 2 points Flavor changed slightly: 1 point Flavors did not change: 0 points

[Table 3]
Yogurt drink
Flavor degradation inhibitor (addition amount: 10 ppm) Product with no average score for sensory evaluation 3.6
L-ascorbic acid 3.3
Extraction Example 1 2.3
Extraction Example 2 3.0
Extraction Example 3 2.5

  As shown in Table 3, it was found that the addition of the flavor deterioration inhibitor of the present invention had a higher flavor deterioration-inhibiting effect than those with no addition and L-ascorbic acid added. Moreover, the taste and smell of the flavor deterioration inhibitor itself of the present invention were not felt.

[Test Example 4] (Lemon drink)
The total amount was adjusted to 100 g with 10 g of granulated sugar, 0.1 g of citric acid, 0.1 g of lemon flavor and water. A glass container was filled with a product to which no flavor deterioration inhibitor was added and 10 ppm of various flavor deterioration inhibitors, and sterilized at 70 ° C. for 10 minutes. After irradiating them with a light stability tester (15000 lux, 10 ° C., 3 days), ten experienced panels were selected for sensory evaluation. In this case, a lemon beverage not irradiated with a fluorescent lamp to which no flavor deterioration inhibitor was added was used as a control, and the degree of flavor change (deterioration) was evaluated. The results are shown in Table 4. In addition, the score of evaluation in Table 4 is the average score of each panel scored on the same basis as in Test Example 3. Also, the off-flavors and off-flavors in the scoring standards refer to “vinyl odor” and “green odor”.

[Table 4]
Lemon drink
Flavor degradation inhibitor (addition amount: 10 ppm) Product with no average score for sensory evaluation 3.8
L-ascorbic acid 4.0
Extraction Example 1 2.8
Extraction Example 2 3.4
Extraction Example 3 3.0

  As shown in Table 4, it was found that the flavor deterioration inhibitory effect was higher when the flavor deterioration inhibitor was added than when the additive was not added and L-ascorbic acid was added. Moreover, the taste and smell of the flavor deterioration inhibitor itself of the present invention were not felt.

[Example 1] Vanilla extract To 10 g of vanilla beans, 35 g of ethanol and 65 g of distilled water were added, and the mixture was allowed to stand and extract in a dark place at room temperature for 4 weeks. By filtering this solution, 90 g of vanilla extract was obtained. 10 g of longan seed extract lyophilized powder 0.1 mass% / 50 mass% ethanol aqueous solution was added to 90 g of this extract to complete the vanilla extract of the present invention.

[Example 2] Grape flavor A grape flavor was prepared according to the following formulation.
Isoamyl isovalerate 10g
Cinnamyl alcohol 5g
60 g of ethyl acetate
15g ethyl butyrate
10 g ethyl 3-methyl-3-phenylglycidate
8g ethyl heptanoate
Methyl anthranilate 130g
15g methyl salicylate
373 g of ethanol
374 g of distilled water
The grape flavor of the present invention was completed by adding 1.0 g of a 1% by weight / 50% by weight ethanol aqueous solution of male peach seed extract to 100 g of the above-described grape flavor.

  The flavor deterioration inhibitor of the present invention can suppress flavor deterioration of foods and beverages and flavors that are easily affected by light, heat, oxygen, and the like, and can be used for various foods, beverages, and flavors. In particular, since it shows a remarkable suppression effect on flavor deterioration due to light, it is excellent when applied to food and drink filled in transparent glass containers, translucent plastic containers, or transparent bags that are easily affected by light. The effect is demonstrated.

Claims (6)

A flavor deterioration inhibitor comprising a solvent extract of seeds of male peach (Syzygium malaccensis) and / or longan (Euphoria longana). The flavor deterioration inhibitor according to claim 1, wherein the solvent extract is obtained by extraction with water, a polar organic solvent or a mixture thereof. A food / beverage product, oral hygiene agent or pharmaceutical product to which the flavor deterioration inhibitor according to claim 1 or 2 is added in an amount of 0.5 to 500 ppm. The flavor deterioration inhibitory method characterized by adding 0.5-500 ppm of the flavor deterioration inhibitor of Claim 1 or 2 to food-drinks, an oral hygiene agent, or a pharmaceutical. The flavoring agent by which the flavor deterioration inhibitor of Claim 1 or 2 is added 0.005-5 mass%. A method for suppressing deterioration of a flavoring agent, comprising adding 0.005 to 5% by mass of the flavor deterioration inhibiting agent according to claim 1 or 2 to the flavoring agent.