JP2001061461A - Flavor deterioration preventing agent derived from citrus fruit - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject safe deterioration preventing agent capable of simultaneously preventing the deterioration of the flavor due to light and heat and having a wide application range by including eriocitrin derived from citrus fruits or an eriocitrin-containing substance as an active ingredient. SOLUTION: This flavor deterioration preventing agent is obtained by directly using eriocitrin or an eriocitrin-containing substance prepared by extracting at least one of a fruit juice, a percarp, a pericarp-containing substance or a fruit juice pressing residue of citrus fruits with water and/or an organic solvent and, as necessary, purifying the resultant extract as an active ingredient or formulating the eriocitrin or eriocitrin-containing substance with a solvent such as an oil and fat, water, ethanol, propylene glycol or glycerol or gum arabic, dextrin, glucose, a surfactant, etc., and including the resultant composition in the form of a powder, a granule, a liquid, an emulsion or a paste or other suitable shapes. The resultant flavor deterioration preventing agent is used for a food and drink, a cosmetic, an industrial chemical, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to the prevention of flavor deterioration, and more particularly to a novel flavor utilizing eriocitrin and / or eriocitrin-containing substances derived from citrus fruits, that is, natural ingredients. It relates to a deterioration prevention system.

[0002]

2. Description of the Related Art Many kinds of raw materials and products originally have flavors, but there has been a problem of flavor reduction and deterioration in processing and storage. Various flavors are used to compensate for the problem of flavor reduction and deterioration. For example, in beverages and foods as processed foods, flavors (natural or synthetic products) are used to enhance appetite.
Is added to enhance the scent. However, it has been difficult to avoid the deterioration of the fragrance during the production process or storage of food and drink. In order to solve this problem, a combination use of chlorogenic acid belonging to polyphenols extracted from green coffee beans for the purpose of antioxidation and proanthocyanidin (Japanese Unexamined Patent Publication No.
-38723).

[0003]

However, none of the conventionally known flavor deterioration inhibitors is known to be completely satisfactory, and the factors that cause deterioration and alteration of flavor include those caused by light and those caused by heat. However, there is no known substance that has a clear effect on both. The above-mentioned known technique is also based on a combination of two or more substances. In view of the state of the art, the present invention newly develops a novel flavor deterioration inhibitor, and a completely new type of previously unknown flavor deterioration inhibitor that is effective for both light and heat. It was done for the purpose.

[0004]

Means for Solving the Problems The present inventor has been made to achieve the above-mentioned object, and in order to respond to the needs of consumers who are strong in safety and directivity of natural products, natural-derived flavors are required. We decided to develop a deterioration inhibitor.

Therefore, the present inventors screened the target substance from the existing natural products widely, but did not succeed. Therefore, the present inventors changed their ideas and found that the citrus fruits derived from citrus fruits recently discovered by the present inventors. Focusing on eriocitrin, which is an oxidizing component, for the first time, adding eriocitrin to foods and drinks with fragrances and fragrances added, not only obtained useful new knowledge that flavor deterioration was suppressed, but also Unexpectedly, a useful new finding was obtained that the deterioration of flavor due to heat or light during processing and storage of these foods and drinks can be suppressed or prevented.

The present invention has been finally completed based on these useful and novel findings, and as a result of further research. Hereinafter, the present invention will be described in detail.

[0007] Eriocitrin has a structural name of eriodictyol-7-rutinosid.
e), which is a flavonoid glycoside in which rutinose (a disaccharide: glucose and rhamnose) is bound to eriodictyol belonging to flavanones among flavonoid compounds. Eriocitrin is found in citrus fruits, especially in lemons and limes, and also in oranges. It has never been known that eriocitrin has excellent antioxidant properties, and it is a novel finding discovered by the present applicant for the first time. Based on this new finding, a novel invention relating to an antioxidant substance derived from citrus fruit Japanese Patent Application Laid-Open No. 9-48969
No. has already been filed. However, it is not known at all that eriocitrin has an excellent effect of preventing flavor deterioration.

In the present invention, as eriocitrin, not only purified eriocitrin itself but also eriocitrin-containing substances can be used. Examples of the former include citrus peels proposed in Japanese Patent Application Laid-Open No. 9-48969 filed by the present applicant,
A method for obtaining eriocitrin by performing a purification treatment such as resin treatment and preparative chromatography after extracting with water and / or an organic solvent, for example, a polar solvent, from the pericarp-containing material, fruit juice, and squeezed cake, and examples of the latter are as follows. After extracting with a polar solvent from citrus peel, juice and squeezed lees proposed in Japanese Patent Application No. 11-162207, the mixture is applied to a synthetic adsorption resin, heated with flowing hot water, eluted with 30% ethanol, and concentrated. The resulting eriocitrin-containing extract can be used. This eriocitrin-containing substance contains flavonoids and the like in addition to eriocitrin.
8-di-C-glucosyldiosmin, hesperidin, naringin and the like.

[0009] It should be noted that, as eriocitrin, not only a chemically synthesized product or a purified product obtained by further purifying an extract, but also eriocitrin-containing substances include all substances containing eriocitrin. And eriocitrin in water or other liquids, solid carriers and the like are all included in the present invention.

The flavor deterioration preventing agent according to the present invention contains eriocitrin (content) as an active ingredient. Eriocitrin (content) is used as it is, and depending on the purpose of use, for example, fats and oils, Water, ethanol,
Solvents such as propylene glycol and glycerin, or gum arabic, dextrin, glucose, surfactants and the like, powdered, granular, liquid, emulsion,
It is also possible to use the composition in the form of a paste or other appropriately shaped composition.

The flavor deterioration preventing agent according to the present invention comprises a product having a flavor originally, a target product to which a flavor is to be added and used (a flavor is not added at this time,
A product to which flavor is added by adding a flavor later) or the flavor itself may be added. In the latter case, essence, oily flavor, emulsified flavor, flavoring such as powdered flavor,
It may be added directly to the flavor seasoning, or may be added during the formulation process when it is formulated into a flavoring agent. In the case of producing a fragrance, the essential oil component is often extracted with ethanol or the like in order to make it water-soluble.

By using the present flavor deterioration preventing agent in this manner, the deterioration, disappearance and alteration of the flavor of the product due to light, heat and the like can be effectively prevented or suppressed. Examples of such products include foods and beverages, luxury goods, feedstuffs, health and medical products, cosmetics, and the like. For example, fruitless beverages, fruit juice beverages,
Lactic acid bacteria drinks, coffee drinks, tea drinks, soy milk drinks, soups, powdered drinks and other drinks, ice cream, sherbet, sleet and other frozen desserts, bavaroa, pudding, jelly, yogurt and other desserts, frozen, powder, Liquid soups, retort pouch foods, foods such as canned foods, other foods and drinks such as drops, candy, pickles, condiments, health and pharmaceutical products such as tablets, liquid oral drugs, powdered oral drugs, compresses, etc. The present invention is useful as a flavor deterioration inhibitor used in cosmetics such as soaps, shampoos, cosmetics, and various industrial chemicals.

[0013] The amount of the flavor deterioration inhibitor of the present invention to be added to these products to be added is not particularly limited, and can be selected from a wide range. And use it,
The addition amount of the perfume deterioration inhibitor can be appropriately changed according to the addition amount of the perfume described below. For example, the amount of eriocitrin to be added is about 0.0001 to 10% by weight, preferably about 0.001 to 1% by weight of the product weight.

Further, the present flavor deterioration preventing agent is prepared by adding various raw materials or products which originally have a flavor, various raw materials or products which are sought to impart flavor by adding a flavor (formulation), and a flavor (formulation). It can be freely used as appropriate for various raw materials or products imparted with flavor, and perfume (formulation) itself.

As for fragrances, synthetic fragrances made synthetically and natural fragrances made from natural products are largely divided.
Normally, synthetic fragrances are very stable, so that the present invention can be expected to be most effective when used for natural fragrances that lack stability. Today, where nature and nature are valued, it is expected that there will be more opportunities for use. In addition, the present flavor deterioration inhibitor is effective for all the above-mentioned fragrances, but is particularly effective for citrus fragrances.
Therefore, the present flavor deterioration preventing agent is particularly useful as a flavor deterioration preventing agent for foods and drinks, but of course, other products can also effectively prevent the deterioration of the flavor.

Hereinafter, the present invention will be described in more detail with reference to examples.

[0017]

Example 1 In order to confirm the effect of eriocitrin on preventing flavor deterioration, eriocitrin and an eriocitrin-containing substance having a flavor deterioration preventing action were produced by the following two methods.

(Method 1) 3 kg of lemon peel was ground with a homogenizer, 12 L of water was added thereto, and the mixture was boiled for 2 hours. Thereafter, the extract was filtered to obtain a filtrate. This was concentrated under reduced pressure by an evaporator to obtain an extract. Then 200ml
Dissolved in water, and reversed-phase resin column (4 cm x 50 cm, C
osmosil 75C18-OPN; Nacalai Tesque, Inc.). After flowing 1.5 L of water, the fraction eluted with 40% methanol was concentrated under reduced pressure, and the concentrate was dissolved in 5 ml of water. Eriocitrin was collected by preparative high performance liquid chromatography, and concentrated to dryness to obtain 5.0 g of powder. (Eriocitrin; contains 90% or more)

(Method 2) 2 kg of lemon peel is ground and
Add 0 L of water, immerse at room temperature for 30 minutes,
The extract was filtered to obtain a filtrate. This is centrifuged (900
(0 rpm, 20 minutes), and the supernatant was passed through a synthetic adsorption resin (200 ml; Amberlite XAD-16; Rohm and Haas Co., Ltd.). Then, after flowing 1 L of water, and then flowing 2 L of warm water to the resin at 60 ° C., 30%
Elution was performed with 1 L of ethanol. The eluate is concentrated to dryness,
10.5 g of eriocitrin-containing extract was obtained. (Eriocitrin; contains 30%)

Using citral, a characteristic component of the citrus flavor, a syrup solution was prepared according to the following composition. 30 g glucose, 0.5 g citric acid, 1 g citral 6
The volume is adjusted to 1 L using 5% ethanol aqueous solution, and 100 m
l of a colorless and transparent glass bottle. To this syrup, the eriocitrin obtained by the method 1 and the eriocitrin-containing substance obtained by the method 2 (containing 30% of eriocitrin) are irradiated with ultraviolet rays for 4 hours (Suga Test Instruments Co., Ltd .: UV Long Life Fade) Meter) and then HPL
C (Shimadzu: LC-10A) was used to measure the citral content, and the reduction rate was determined. The reduction rate was expressed assuming that the amount of citral at the start (unirradiated with ultraviolet rays) was 100. Table 1 shows the results.

(Table 1) Residual rate of citral (%) No addition 33.8 Eriocitrin (200 ppm) 54.9 Eriocitrin-containing material (Eriocitrin content 200 ppm) 78.4

From this table, it has been clarified that the eriocitrin and the eriocitrin-containing substance of the present invention exhibit a remarkable effect of preventing degradation of citral, which is a flavor component, by ultraviolet rays.

[0023]

Example 2 Bx10, p using glucose and citric acid
To the solution adjusted to H = 3, 0.1% of lemon essence (manufactured by Takasago International Corporation) was added to prepare a syrup solution. To this, a section to which 200 ppm of the eriocitrin-containing substance obtained by the method 2 of Example 1 was added and a section to which no eriocitrin was added were prepared, and these were heated to 90 ° C., instantaneously sterilized, and filled in a colorless and transparent PET bottle. GS-MS (HEWLETT PACKAR) after 14 days in direct sunlight
D: HP6800 series). The residual ratio was determined when the amount of each flavor component of the sample stored in the refrigerator was 100. Table 2 shows the results.

(Table 2) Percentage of odor components remaining (%) Not added Eriocitrin-containing additive added Limonene 12.6 29.7 Linalool 49.7 77.1 Geraniol 60.2 85.2 Terpineol 55.3 85.9

From this table, it has been clarified that the eriocitrin-containing substance of the present invention has a remarkable effect of preventing the decomposition and deterioration of the fragrance component due to the ultraviolet ray decomposition.

[0026]

Example 3 Bx6, pH using glucose and citric acid
0.1% of orange essence (manufactured by Takasago International Corporation) was added to the solution adjusted to = 3 to prepare a syrup solution. To this, a section to which 200 ppm of the eriocitrin-containing substance obtained by the method 2 of Example 1 was added and a section to which no eriocitrin was added were prepared, and these were heated to 90 ° C., instantaneously sterilized, and filled in a colorless and transparent PET bottle. After standing at 60 ° C. for 4 days, sensory evaluation was performed by 10 well-trained panelists. In this method, a sample stored in a refrigerator (without heat abuse) was scored out of 5 points, and the score of each section was obtained, and an average score was obtained. Table 3 shows the obtained sensory evaluation results.

(Table 3) Sensory Evaluation Points (Average) Fresh Feeling Juice Feeling Aroma Strength Total Evaluation Not Added 2.0 2.2 2.5 2.2 Eriocitrin-Containing Substance 4.2 3.8 4.0 4.0

From this table, it was clarified that the eriocitrin-containing substance of the present invention exhibited a remarkable effect of preventing deterioration of the fragrance component due to heating.

[0029]

According to the present invention, eriocitrin, which is an antioxidant component derived from citrus fruit, or an eriocitrin-containing substance, is effective as a commercially valuable flavor deterioration inhibitor. In addition, the flavors to which they are added can reduce the reduction and deterioration of the flavor when used in foods and drinks. Moreover, the flavor deterioration inhibitor according to the present invention is highly safe because it is derived from a natural product, and is epoch-making in that it is effective against both flavor deterioration due to light and flavor deterioration due to heat. In addition, it can be widely used for preventing deterioration of flavors of foods and beverages as well as cosmetics and various other products.

Continuing on the front page (72) Inventor Masanori Hiramitsu 12-sha, Kumanosho, Nishi-Kasugai-gun, Aichi Pref. 12 companies, 45-2 Pokka Corporation Basic Technology Laboratory F term (reference) 4B021 LA01 LP01 LP10 LW05 LW06 LW07 MC03 MC10 MK05 MK28 MP01 MQ04 MQ05 4B047 LB03 LB08 LF01 LF05 LF07 LF08 LF09 LG05 LG38 LP01 LP02

Claims (6)

[Claims] 1. A flavor deterioration inhibitor comprising eriocitrin or an eriocitrin-containing substance as an active ingredient. 2. An eriocitrin or an eriocitrin-containing substance, wherein at least one of citrus juice, pericarp, pericarp-containing substance, and fruit juice extract cake is extracted with water and / or an organic solvent,
The flavor-deterioration inhibitor according to claim 1, wherein the extract is purified as required. 3. The flavor-deterioration inhibitor according to claim 1, wherein the flavor-deterioration agent is for preventing and / or suppressing the deterioration of the flavor due to heat and / or light. 4. The flavor deterioration preventing agent is at least one of a flavor deterioration preventing agent for food and drink, a flavor deterioration preventing agent for cosmetics, a flavor deterioration preventing agent for pharmaceuticals, and a flavor deterioration preventing agent for industrial chemicals. The flavor deterioration preventing agent according to any one of claims 1 to 3. 5. A flavor product comprising the flavor deterioration inhibitor according to any one of claims 1 to 4. 6. The flavor product according to claim 5, wherein the flavor product is a food or drink.