JP2704783B2 - Prevention method of flavor deterioration of food and drink - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a method for preventing flavor deterioration of foods and drinks, and more specifically, a group consisting of chlorogenic acid, caffeic acid and ferulic acid (hereinafter sometimes referred to as group A). ) And at least one selected from the group consisting of vitamin C, rutin, and quercetin (hereinafter sometimes referred to as group B) in the food or drink, thereby improving the flavor and flavor of the food or drink. The present invention relates to a method for effectively suppressing undesired flavor deterioration such as change and generation of an off-flavor.

[Related Art] Deterioration of flavor during the manufacturing process or storage of food and drink is inevitable to some extent. Conventionally, efforts have been made to reduce the flavor deterioration of these foods and drinks as much as possible. For example, in recent years, vacuum-cooked foods in which raw food materials are vacuum-packaged and the bags are heated and cooked at a low temperature have become fragrant. It is noted that the taste of food materials can be tasted as it is without dissipation, but there is a limit to the appropriate range of the material, and there are many unsolved issues such as the problem of remaining bacteria, so it is still satisfactory It is not a viable way.

On the other hand, some proposals have been made regarding prevention of discoloration such as fading or browning of foods and drinks, for example, chlorogenic acid,
An anti-fading agent for anthocyanin dyes utilizing antioxidant properties such as caffeic acid (Japanese Patent Publication No. 1-222872), an anthocyanin dye-containing food and drink (Japanese Patent Application Laid-Open No. 1-132344),
A method of preventing fading of paprika dyes (JP-B-59-50265) and the like are disclosed. Also, a method for preventing browning of saccharides with caffeic acid, ferulic acid, chlorogenic acid, etc.
No. 57-115147), and a method for producing candy without browning utilizing the browning preventing effect of saccharides (Japanese Patent Publication No. 58-32855). Furthermore, an antiallergic food which suppresses histamine release by adding caffeic acid, chlorogenic acid or the like as an essential component to food has been proposed (JP-A-60-192555).

In addition, it is known that substances exhibiting antioxidant properties such as chlorogenic acid, caffeic acid and ferulic acid are contained in coffee beans and the like, and there are some proposals regarding methods for extracting these antioxidant substances. (JP-A-58-138347)
And JP-A-62-111671).

Chlorogenic acid, caffeic acid, ferulic acid, etc., as described above, alone are not sufficiently effective in suppressing the deterioration of flavor. Vitamin C, rutin and quercetin, which are used for the same purpose, also have a small effect in preventing the deterioration of flavor of foods and drinks, and are not practical, and when vitamin C is added, the deterioration of flavor is accelerated. It is well known that there are many cases.

However, surprisingly, at least one selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid.
By incorporating at least one selected from the group consisting of the seeds and vitamin C, rutin, and quercetin into foods and drinks, they act complementarily and synergistically, resulting in extremely remarkable deterioration of flavor and deterioration. It has been shown for the first time by the inventors of the present invention that the present invention exhibits a sustained effect.

[Problems to be Solved by the Invention] Despite the fact that the quality of flavor during the processing or storage of food and drink is a serious problem, no satisfactory solution has yet been found.

Such deterioration of the flavor of foods and drinks is a troublesome problem that occurs regardless of the presence or absence of pigments such as anthocyanins and paprika pigments or sugars disclosed in the conventional proposals as described above.

Food and drink flavors generally consist of a collection of extremely unstable compounds, which are susceptible to the effects of heat, light, air, enzymes, etc. during the processing or storage of food and drink, thereby deteriorating and degrading quality. It is well known that it causes a decline. Many reactions such as oxidation, reduction, dehydrogenation, hydrolysis, polymerization, ring closure, ring opening, esterification, decarboxylation, and transfer of double bonds are involved in the reactions that cause deterioration of foods and drinks.

By adding caffeic acid alone or in combination with deferiferic chromes to sake, it can not only increase coloration and generate off-flavors (sun odor) when irradiated with sunlight, but also found in other antioxidants It has already been disclosed in JP-B-47-41040 that no abnormal color increase during storage is observed.

The publication describes that it is possible to prevent the increase in coloring and the occurrence of sunlight odor when sake is irradiated with sunlight, but the flavor originally possessed by ordinary foods and drinks other than sake is It is not stated to prevent any deterioration caused by heat, oxygen or any other unspecified factors as well as sunlight during processing and storage of the product, and even less selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid. By adding at least one selected from the group consisting of vitamin C, rutin, and quercetin to foods and drinks, they act complementarily and synergistically, resulting in extremely remarkable deterioration of flavor. It does not mention or even suggest that it shows a preventive effect and that the effect is of excellent sustainability. . The present inventors have at least one selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid and vitamin C in general food and drink other than the sake.
By containing at least one selected from the group consisting of rutin and quercetin, it is possible to effectively suppress undesirable flavor deterioration such as reduction or change of aroma and flavor and generation of off-flavor during processing or storage of the food or drink. The present invention has been completed by finding out what can be done.

Furthermore, it was also found that chlorogenic acid, caffeic acid, ferulic acid and the like can be replaced not only with synthetic products but also with natural green coffee extract.

Accordingly, an object of the present invention is to make a food or drink contain at least one selected from the group consisting of chlorogenic acid, caffeic acid, and ferulic acid and at least one selected from the group consisting of vitamin C, rutin, and quercetin. It is an object of the present invention to provide a method for effectively preventing flavor deterioration of the food or drink.

[Means for Solving the Problems] The chlorogenic acid (3-caffeylquinic acid) used in the present invention is contained in, for example, coffee beans in the form of potassium chlorogenate caffeine.
Sweet potato, pear leaf, apple pulp and other widely distributed plants. Also, caffeic acid (3,4-dioxynicsilicic acid) was isolated as a saponified potassium hydroxide of coffee tannin and was synthesized in 1878 by Tiemann et al. Caffeic acid is also present in free form in coniferous bark, polygonaceae, tobacco, etc., but is widely distributed in plants, including coffee beans, as chlorogenic acid combined with quinic acid. Ferulic acid (4-oxy-3-methoxycinnamic acid, caffeic acid 3-methyl ether) is contained in rubber resin Agi and the like, but can also be synthesized by a Parkin reaction between vanillin and acetic anhydride.

The chlorogenic acid, caffeic acid and ferulic acid used in the present invention are commercially available, but can also be extracted and collected from natural products. These chlorogenic acid, caffeic acid and ferulic acid need not necessarily be pure products, and can be obtained, for example, as follows.

For example, about 0.5 to about 20 times by weight of ethanol or hydrous ethanol is added to the ground coffee green beans, and the mixture is heated at, for example, about 60 ° C. to 100 ° C., for about 1 hour to about 10 hours. After cooling, hydrochloric acid is added to the extract A obtained by separating and removing the insoluble solids so that the hydrochloric acid concentration becomes, for example, about 3 to 10%, for example, at about 50 ° C. to about 100 ° C. for about 30 minutes. Heat and stir for ~ 5 hours. Next, after concentration, the concentrate is neutralized using, for example, sodium hydroxide, potassium hydroxide, or the like, and further treated with, for example, a porous polymer resin to be adsorbed on the resin, and then the resin is eluted with, for example, ethanol. Thus, an extract containing chlorogenic acid, caffeic acid and the like can be obtained. Alternatively, the solvent used in the present invention can be obtained by collecting the solvent as it is without hydrolyzing the extract, concentrating the extract, washing with methylene chloride or the like, and then subjecting the extract to adsorption treatment with a porous polymer resin as described above. An extract can be obtained.

The chlorogenic acid, caffeic acid and ferulic acid used in the present invention or a coffee extract containing them may be used as such or in the form of a composition of these active ingredients with a suitable diluent or carrier. Examples of such diluents or carriers include solid diluents or carriers such as gum arabic, dextrin, glucose, cyclodextrin, sucrose, etc., and liquid diluents such as water, ethanol, propylene glycol, glycerin, surfactants and the like. Agents or carriers.
Using such a diluent or carrier, a liquid, an emulsion, a paste, a powder, a granule or any other appropriate dosage form can be obtained.

In the present invention, at least one selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid is used.
The use of at least one selected from the group consisting of a seed and L-ascorbic acid, rutin, and quercetin complements and synergistically enhances the flavor deterioration preventing effect on foods and drinks. These synergists of the group (B) consisting of L-ascorbic acid, rutin and quercetin are used simultaneously with the addition of at least one selected from the group (A) consisting of chlorogenic acid, caffeic acid and ferulic acid to food and drink. At the time of adding or processing into the above dosage form, at least one selected from the group (A) and at least one selected from the group (B) may be previously blended. .

If desired, natural essential oils, recovered fragrances, synthetic fragrances added to foods and drinks for the purpose of flavoring, and fragrance compositions obtained by mixing and blending these fragrances and the like may be used in the present invention. One type and at least one type selected from the group (B) may be blended.

In the method for preventing flavor deterioration of foods and drinks of the present invention, at least one selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid isolated from synthetic or natural products as described above, and vitamin C, rutin and quercetin By blending at least one selected from the group consisting of food and drink as an active ingredient, the original flavor of the food and drink can be prevented from being altered or deteriorated, as well as newly added essence, It is effective in preventing flavors such as oily flavors, emulsified flavors and powdered flavors, and flavors such as flavor seasonings from being altered or deteriorated.

Specific examples of foods and beverages in the present invention include, for example, bottles, cans, paper carton containers, PET bottles, laminating bags for retorts, fruitless beverages filled in plastic cups, fruit-containing beverages, lactic acid bacteria beverages, tea Foods and drinks other than sake, such as beverages, coffee drinks, soy milk drinks, and soups; frozen desserts such as ice cream, sherbet, and sleet; and dessert foods such as pudding, bavaroa, jelly, and yogurt.

In the present invention, at least one selected from the group (A) consisting of chlorogenic acid, caffeic acid and ferulic acid and vitamin C added for the purpose of preventing flavor deterioration,
At least one compounding ratio selected from the group (B) consisting of rutin and quercetin is as follows: (A) :( B) = 2: 1 to 1: 5
0, preferably (A) :( B) = 1: 1 to 1:20. The amount of addition is often in the range of about 0.001 to about 0.5% by weight, preferably about 0.005 to about 0.1% by weight in total.

Hereinafter, specific examples of the method for preventing flavor deterioration of the present invention will be described in more detail with reference to Examples and Examples.

Example Reference Example 1 300 g of green coffee beans was ground in a coffee mill, and a 5% by weight 70% aqueous ethanol solution was added to the ground material to prepare
The mixture was stirred and heated for 2 hours. After cooling, insoluble solids were removed to obtain 1100 g of an extract. Next, 180 g of 35% hydrochloric acid was added thereto to adjust the concentration of hydrochloric acid in the extract to about 5%, and the mixture was stirred and heated at 70 ° C. for 1 hour. After cooling, the mixture was concentrated under reduced pressure to 300 g, and the obtained concentrate was adjusted to pH 11 or more by adding 20% sodium hydroxide, and then methylene chloride 60
0 g was added and mixed and stirred well. Separate the aqueous layer and add 10
% Hydrochloric acid was added to adjust the pH to 6-7, and the pH-adjusted solution was gradually flowed through a column filled with 500 ml of Diaion HP-20 resin. Next, the resin was sufficiently washed with water, and then 300 g of 95% ethanol was flowed to elute substances adsorbed on the resin. The obtained solution was concentrated under reduced pressure and dried to obtain 12 g of a mixture of chlorogenic acid and caffeic acid (Product 1 of the present invention).

Example 1 12 parts by weight of granulated sugar, 0.15 part by weight of citric acid and 0.02 part by weight of sodium citrate were dissolved in 88 parts by weight of water to obtain Br.
An ix12 ゜, pH 3.0 lemon syrup was prepared. A predetermined amount of chlorogenic acid, caffeic acid, vitamin C and rutin is added or dissolved alone or in combination to this syrup, and lemon essence is added to each of the obtained syrups in 1/1000 parts by weight, and then filled in a transparent glass bottle. The bottle was sealed, sterilized at 85 ° C. for 15 minutes, and then cooled to prepare a test lemon beverage.

After each beverage was exposed to direct sunlight for 3 days, the flavor was compared with the corresponding sample stored in the refrigerator. The degree of flavor degradation was sensory evaluated by 10 well-trained panelists. Table 1 shows the results.

As is evident from the results in Table 1, chlorogenic acid, caffeic acid and ferulic acid each show a certain degree of flavor deterioration preventing effect even when used alone, but have not been sufficient yet. In addition, the vitamin C alone additive deteriorated and deteriorated to such a degree that no difference was observed with the additive-free product. On the other hand, samples obtained by adding vitamin C or rutin to chlorogenic acid, caffeic acid and the like, including the product 1 of the present invention, showed almost no deterioration of flavor even though the amount of each was small.

[Effects of the Invention] According to the present invention, at least one member selected from the group consisting of chlorogenic acid, caffeic acid, and ferulic acid and at least one member selected from the group consisting of vitamin C, rutin, and quercetin are used in foods and drinks. Reduction or change in flavor or flavor during processing or storage of the food or drink by containing it,
Undesirable flavor deterioration such as generation of an off-flavor can be effectively suppressed.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical display location A23L 3/3562 A23L 2/00 P

Claims (2)

(57) [Claims] (1) at least one selected from the group consisting of chlorogenic acid, caffeic acid and ferulic acid, and vitamin C;
A method for preventing flavor deterioration of foods and drinks, wherein at least one selected from the group consisting of rutin and quercetin is contained in foods and drinks. 2. The method according to claim 1, wherein the chlorogenic acid, caffeic acid and ferulic acid are green coffee extract.