GB2289676A - Freshness retaining agent for food comprising ferulic acid - Google Patents
Freshness retaining agent for food comprising ferulic acid Download PDFInfo
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- GB2289676A GB2289676A GB9501773A GB9501773A GB2289676A GB 2289676 A GB2289676 A GB 2289676A GB 9501773 A GB9501773 A GB 9501773A GB 9501773 A GB9501773 A GB 9501773A GB 2289676 A GB2289676 A GB 2289676A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/145—Acids, anhydrides or salts thereof
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/18—Carbohydrates
- A21D2/186—Starches; Derivatives thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B4/00—General methods for preserving meat, sausages, fish or fish products
- A23B4/12—Preserving with acids; Acid fermentation
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
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- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Storage Of Fruits Or Vegetables (AREA)
Description
2289676 FOR FOOD The present invention relates to a freshness retaining
agent for food and to a method of retaining the freshness of food using said freshness retaining agent. More precisely, it relates to a freshness retaining agent for food capable of effectively preventing food from being discolored, rotted or oxidized and to a method of retaining the freshness of food using it.
BACKGROUND OF THE INVENTION
It is known that ferulic acid has anti-oxidative, anti-microbial and tyrosinase activity-inhibiting functions. Though being soluble in water, however, ferulic acid is influenced by temperature and is therefore hardly soluble and dispersible in cold water. Therefore, it has been said that heating is necessary so as to uniformly disperse or dissolve ferulic acid in water. In addition, when a preparation containing ferulic acid is used for the purpose of retaining the freshness of food, it has a problem in that its dispersion in some kinds of food is uneven so that it cannot display a sufficient effect. As being high-priced, moreover, ferulic acid has another problem in that its addition to food at a concentration enough to express its sufficient effect will noticeably detract from the economical use thereof.
Given the situations, it is desired to develop a low-priced ferulic acidcontaining preparation free from the above-mentioned problems.
On the other hand, sulfur dioxide-containing preparations and kojic acid-containing preparations have been commercially sold in the market as tyrosinase activity-inhibiting agents. However, these are considered unsatisfactory in view of their safety, and safer natural preparations are des 1 red.
Natural substances which are applied to food as anti-microbial ones greatly depend on PH conditions. For instance, it is general that polylysine and protamine having a relatively high anti-inicrobial activity are effective in natural to alkaline conditions while organic acids are effective in neutral to acidic conditions. However, it has been pointed out that organic acids, when added to food, have bad influences on the taste of the food. Therefore, it is strongly desired to develop a method of applying natural anti-microbial substances to food in acidic conditions without having any bad influences on the taste of the food, and it is also expected to develop anti-microbial preparations capable of expressing their anti-microbial activity in a broad PH range.
SUWARY OF THE INVENTION The present invention is to make ferulic acid, which is effective for retaining the freshness of food. soluble in cold water while amplifying the functions of the acid and stabilizing it, by which a freshness retaining agent for food containing the acid and a method of retaining the freshness of food using the agent are provided.
Specifically, the present invention provides a freshness retaining agent for food characterized by containing ferulic acid in the form of its inclusion complex of cyclodextrin, a freshness retaining agent for food characterized by containing ferulic acid or an inclusion complex of ferulic acid with cyclodextrin along with a DH-adjusting buffer, and a method of retaining the freshness of food characterized by bringing food into contact with an aqueous solution containing said freshness retaining agent and having been adjusted to have pH of from 3 to 10.
DETAILED DESCRIPTION OF THE INVENTION
Ferulic acid to be used in the present invention may be either a natural substance extracted from plants or a chemical product to be obtained from a starting material of vanillin. Preferred is the former to be extracted from plants.
Ferulic acid includes cis- and trans-isomers, which convert into each other when exposed to light. The cis-isomer is yellow oil, while the transisomer is in the form of rhombic-system needle-like crystals; and they have quite different properties. In general. the ferulic acid exists as a mixture of these isomers. Therefore, the ferulic acid to be employed in the present invention is not specifically defined with respect to the proportion of its isomers. The purity of the ferulic acid to be employed in the present invention is not also specifically defined. Anyhow, in order to attain the effect of the present invention, the agent may contain 10 % or more ferulic acid. To conveniently formulate preparations containing ferulic acid according to the present invention, the purity of the acid is preferably 50 % or more.
As cyclodextrin to be used for forming an inclusion complex of ferulic acid, a -, 7 -, 6 -cyclodextrins and branched cyclodextrins such as maltosylcyclodextrin, can be used singly or as a combination of two or more of them. Of these, preferred is a highly water-soluble maltosylcyclodextrin mixture (trade name:lsoelite, produced by Ensuiko Sugar Refining Co-Ltd.).
To produce an inclusion complex of ferulic acid with cyclodextrin (hereinafter referred to as CD), in general, ferulic acid and CD are dissolved in hot water and the resulting aqueous solution is sprayed and dried; or ferulic acid and CD are dissolved in an aqueous alcohol having an alcohol concentration of from 10 to 60 % and the resulting alcoholic solution is dried. If mass-production of a large amount of the inclusion complex is desired, the former hot water-dissolving method is preferred as being economical. If, however, laboratory-scale production of a small amount of the same is desired, the latter aqueous alcoholic method is preferred.
To produce the CD inclusion complex of ferulic acid, the ratio of ferulic acid to CD to be mixed together is, in general, suitably from 1:100 to 2:1. In order to more elevate the solubility of the acid in CD, the ratio of CD to the acid is increased. For this. CD is used preferably in an amount of about 3 times or more of the acid.
The CD inclusion complex of ferulic acid has high solubility in water and may be used singly. On the other hand. however, if ferulic acid not in the form of its CD inclusion complex is used. it must be combined with a suitable buffer to make it stable in a broad pH range. It is preferred that the CD inclusion complex of ferulic acid is also used along with a buffer. In addition, ferulic acid or its CD i&nclusion complex may be combined with antimicrobial and anti-oxidative substances so as to improve the effect of the acid, as will be mentioned hereinafter.
The freshness retaining agent for food of the present invention is used in such a way that the content of ferulic acid therein may be 50 ppm or more, Preferably from 100 to 5000 ppm.
When the freshness retaining agent for food of the present invention is used for preventing vegetables and fruits, such as cabbage, spinach, bean sprouts, burdock, crown daisy, raw shiitake mushroom, apple, pear, mushroom. mandarin orange, strawberry, peach, pineapple, banana, etc., from being discolored, it is formed into an aqueous solution containing generally 100 ppM, preferably from 300 to 500 Ppin of ferulic acid, and vegetables or fruits are dipped in the aqueous solution for 1 to 60 minutes or the aqueous solution is sprayed over vegetables or fruits, by which vegetables or fruit are brought into contact with the solution. In this way, the discoloration of the thus-treated vegetables and fruits may be retarded or prevented.
The agent be combined with anti-microbial and anti-oxidative substances such as ascorbic acid, sodium ascorbate, citric acid, sodium citrate, salt, phytic acid, Diant-derived polyphenols, polylysine, etc., at any desired ratio, by which the combinations may display synergistic effects.
Addition of a PH buffer to an aqueous solution containing ferulic acid makes the solution stable in a broad PH range.
In order to prevent noodles essentially made of wheat, such as Japanese noodles, buckwheat noodles, Chinese noodles, Japanese fine noodles to be eaten as iced noodles, Japanese vermicelli noodles, coatings, macaroni, spaghetti, etc., from being discolored (to be blackish gray or brown or to have specks), the freshness retaining agent of the present invention may be incorporated thereinto, when they are prepared, in an amount of generally 100 ppm or more. preferably from 500 to 5000 ppm in terms of ferulic acid. It is recommended to combine the agent with an emulsifying agent (e.g., lecithin, sugar esters, glycerin fatty acid esters, sorbitan fatty acid esters, enzyme-processed lecithin), ascorbic acid, sodium ascorbate, etc., by which the effect of the agent is enhanced more.
On the other hand, the agent may be directly kneaded into the dough for fried foods (fried instant noodles, fried cookies, shaped potato chips, fried doughnuts, fried fish pastes, other various fries, etc.), in an amount of generally 50 ppin or more, preferably from 100 to 5000 ppm in terms of ferulic acid, by which the deterioration of these foods due to oxidation thereof may be prevented. In this case, it is recommended to combine the agent with ascorbic acid, sodium ascorbate, plant-derived polyphenols, citric acid, sodium citrate, protein hydrolysates, vitamin E, rosemary extract, etc., by which the antioxidative effect of the agent may be synergistically enhanced.
In general, to prevent various foods such as ordinary household dishes, cookies, breads, sauces, fish or meat paste products, etc. from being deteriorated, the agent containing ferulic acid (especially preferably as its CD inclusion complex) is added thereto in an amount of generally 10 ppm or more, preferably from 50 to 5000 ppm in terms of ferulic acid, along with one or more anti-microbial substances chosen from among chitosan, glycine, ethanol, various tea extracts (including catechins and flavones extracted from tea leaves), lysozyme, allyl isocyanate, protamine, polylysine, bamboo extracts (of which the constitutive components are unknown), albino-protein hydrolysates, etc. and/or a pH buffer, by which these foods may be prevented from being rotted by microbes, etc.
Where ferulic acid is used according to the present invention not in the form of its CD inclusion complex, the ferulic acid content in the alcoholic preparation may be generally 10 ppin or more, preferably from 100 to 5000 ppm.
In other preparations than the alcoholic preparation, the ferulic acid content may be generally 0.1 % or more, preferably from 1 to Where ferulic acid is used in the form of an aqueous solution (solution for contacting with food, abbreviated as "contact solution" hereinunder) according to the present invention, the ferulic acid content therein may be generally 10 ppm or more, preferably 100 ppm or more.
The plant-derived polyphenols usable in the present invention include, for example, plant tannins, catechins and flavones, such as quercetin, rutin, glycosyl a-rutin (made by Toyo Seito Co.,Ltd.), green tea extract (consisting essentially of catechins and flavones), oolong tea extract (consisting essentially of catechins and flavones), gallic acid, etc.
The protein hydrolysates usable in the present invention are obtained by hydrolyzing casein, milk albumin, egg albumin, gluten, soybean protein, etc. with enzymes or acids, and these contain peptides having a molecular weight of 100,000 or less in an amount of 10 % or more.
As examples of the buffer for use in the present invention, mentioned are adipic acid, citric acid, sodium citrate, glucono-6-1actone, gluconic acid, succinic acid, sodium succinate, acetic acid, sodium acetate, tartaric acid, sodium tartrate, lactic acid, sodium lactate, glacial acetic acid, fumaric acid, sodium fumarate, malic acid, sodium malate, potassium hydrogentartrate, sodium carbonate, potassium carbonate, disodium hydrogenphosphate, sodium dihydrogenphosphate, dipotassium hydrogenphosphate, potassium dihydrogenphosphate, sodium dihydrogenpyrophosphate, trisodium phosphate, itaconic acid, phytic acid, ketoglutaric acid, etc. One or more of these are used singly or in combination, to adjust the PH of the aqueous ferulic acid-containing solution.
The PH adjustment for food to which the agent of the present invention is applied and the PH adjustment of the contact solution to be applied to food according to the present invention mean as follows: For the former, when ferulic acid or a ferulic acid-containing preparation is added to food, the pH of the food itself is adjusted to fall within the range of from about 3.0 to about 12, according to the pH adjustment of the present invention. For the latter, the PH of ferulic acid or a solution (contact solution) containing ferulic acid dissolved therein is adjusted to fall within the range of from about 3.0 to about 12, according to the same.
The contact between food and the contact solution to be effected according to the present invention includes such that food is dipped in the contact solution, food is boiled in the contact solution, and the contact solution is sprayed over food. For these. the temperature and the concentration of the contact solution and the time for the contact are not specifically defined. In general, the contact solution is applied to food at 0 to 100' C for about one minute to one hour.
Where ferulic acid is mixed with other substances and used according to the present invention, any mixing method may be employed. For instance, powder to-powder mixing and liquidto-powder mixing means may be employed. In addition, the acid and other substances may be dissolved or dispersed in a solvent such as water so as to mix them therein, or the mixture of them may be dried to powder.
According to the present invention, ferulic acid is made into its CD inclusion complex, which becomes soluble in cold water and is handled with ease. In addition, ferulic acid may be combined with other substances having various functions, by which the function of the acid itself is improved or is synergistically enhanced.
Using the freshness retaining agent for food of the present invention, the freshness of various foods may be retained well. In other words, foods stored in the presence of the freshness retaining agent of the present invention are not deteriorated or are prevented from being faded, oxidized or 1 rotted. Thus, using the agent, it is possible to retain the freshness of food for a long period of time. In particular, ferulic acid in the form of an inclusion complex with cyclodextrin is soluble even in cold water and may easily and surely be used for retaining the freshness of various foods.
While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.
Next, the present invention will be explained in more detail by means of the following examples, which, however, are not intended to restrict the scope of the present invention.
Example 1:
g of ferulic acid having a purity of 98 % and 450 g of maltosyl cyclodextrin mixture (trade name:Isoelite, produced by Ensuiko Sugar Refining Co-Ltd.) were completely dissolved in 3 liters of aqueous 50 % ethanol solution, and the resulting solution was evaporated to dryness, using a vacuum rotary evaporator. The thus-formed solid was powdered to obtain a CD inclusion complex of ferulic acid. This is referred to as ferulic acid-CD inclusion complex I.
On the other hand, 10 g of ferulic acid having a purity of 80 % and 20 g of 8-CI) were dissolved in one liter of hot water, and the resulting solution was dried, using a spraying drier, also to obtain a CD inclusion complex of ferulic acid. This is referred to as ferulic acid-CD inclusion complex II.
Each of these two ferulic acid-CD inclusion complex was added to 100 ffil of water at 100C, while stirring, to have a ferulic acid content therein of one g, whereupon the solubility of the inclusion complex was observed. On the other hand, one g of non-processed ferulic acid was added to water in the same manner as above, whereupon the solubility of the acid was also observed.
As a result, ferulic acid-CD inclusion complex I completely dissolved in water while ferulic acid-CD inclusion complex II almost completely dissolved in water though some insoluble solids remained therein. However, the nonprocessed ferulle acid did not almost dissolve in water.
Example 2:
Ferulic acid-CD inclusion complex 1 obtained in Example 1 was combined with one of ascorbic acid, sodium ascorbate, citric acid, sodium citrate and phytic acid and dissolved in water to prepare aqueous solutions. Mushrooms, cabbages or burdocks were dipped in each of these solutions or water for 10 3 days at ITC, whereupon their colors were observed. The results are shown in Table 1 below, from which it is noted that the discoloration of the tested vegetables was prevented by the method of the present invention.
minutes. These were then stored for - 1 0 - Table 1
Ferulic Acid Chemical Added PH Mushrooms Cabbages Burdocks 0 pprn 6.7 Ascorbic Acid (0.5 %) 3.0 Na Ascorbate (1.0 %) 7.1 Citric Acid (0.3 %) 2.8 Na Citrate (0.5 %) 8.0 Phytic Acid (0.1 %) 2.8 -------------------------------------------------------------------------------------------- ppm 5.5 Ascorbic Acid (0.5 %) 3.1 Na Ascorbate (1.0 %) 6.7 Citric Acid (0.3 %) 2.9 Na Citrate (0.5 %) 7.8 Phytic Acid (0.1 %) 2.9 : Thickly browned. ++: Thickly browned but less than +++. Browned. Browned only a little. Not browned.
1 Example 3:
0.1 % of ferulic acid-CD inclusion complex I obtained in Example 1 was combined with each of 0.2 % of sodium ascorbate, 100 ppm of allyl isocyanate and 0.1 % of phytic acid, and kneaded into dough for raw Japanese noodles, raw buckwheat noodles or Chinese noodles, and the dough was formed into raw noodles. These were stored for 3 days at room temperature, whereupon these were observed as to whether or not the raw Japanese noodles and the raw buckwheat noodles became blackened or the Chinese noodles became specked. The results are shown in Table 2 below, from which it is known that the discoloration of these noodles was prevented by the method of the present invention.
Table 2
Ferulic Acid Chemical Added Raw Japanese Noodles Raw Buckwheat Chinese Noodles Noodles Not Added Na Ascorbate Allyl Isocyanate Phytic Acid Na Ascorbate Allyl Isocyanate Phytic Acid + + Thickly browned.
Browned.
Browned only a little.
Not browned.
0.1 % Example 4:
6000 ppm of ferulic acid-CD inclusion complex II obtained in Example 1 - 1 2 - and 2000 ppm of ferulic acid were separately combined with 100 ppm of vitamin E, 100 ppm of emulsifying agent, 500 ppin of soybean hydrolysate and 100 ppm of rosemary extract. as shown in Table 3 below, and the mixture was kneaded into dough for Chinese noodles. The dough was formed into fried, instant Chinese noodles by an ordinary method, and the noodles were stored in an oven at 60t to test the storage stability thereof. The storage stability was evaluated by measuring the peroxide value of the oil extracted from the stored, instant Chinese noodles by an ordinary method. The results obtained are shown in Table 3, from which it is obvious that the oxidation of the oil in the noodles was inhibited by the present invention.
- 1 3 - Table 3
Test Group Ferulic Acid Chemical(s) Added Peroxide Value (meq/kg) 0 day 7 days 14 days 21 days 29 days Not Added 2.5 14.6 31.4 Vitamin E + Emulsifying Agent 2.5 13.1 28.4 - Soybean Hydrolysate 2.4 14.1 25.1 39.4 Rosemary Extract 2.0 12.1 24.1 35.2 ------------------------------------------------------------------------------------------ Ferulic Acid -CD inclusion complex 11 1.8 4.5 10.2 20.1 30.4 Vitamin E + Emulsifying Agent 1.4 2.1 8.4 14.5 25.2 Soybean Hydrolysate 0.7 1.7 6.7 12.1 23.1 Rosemary Extract 0.4 0.7 4.9 9.8 19.8 Ferulic Acid 1.8 4.4 9.9 19.4 29.8 Vitamin E + Emulsifying Agent 1.0 2.0 7.9 13.5 24.1 Soybean Hydrolysate 0.6 1.0 5.4 11.9 22.9 Rosemary Extract 0.3 0.7 4.9 10.1 20.5 Example 5:
Ferulic acid-CD inclusion complex I obtained in Example 1 was combined with one compound selected from the group consisting of glycine, green tea extract, protamine, polylysine, acetic acid, sodium acetate, malic acid, sodium malate, lactic acid, sodium lactate, citric acid and sodium citrate, as indicated in Table 4 below. The mixtures were separately added to a tryptosoyagar medium to prepare plate agar media. One loopful of each of eight strains of Bacillus subtillus (hereinafter referred to as B), Staphylococcus aureus (hereinafter referred to as St), Escherichia coli (hereinafter referred to as E), Sarcina typhimurium (hereinafter referred to as SI),Hansenula anomala (hereinafter referred to as H), Saccharomyces cerevislae (hereinafter referred to as S), Lactobacillus plantarum (hereinafter referred to as L) and Aspergillus niger (hereinafter referred to as A) was streaked on each medium prepared above and put in an incubator kept at 30t, whereupon the growth of the cells was observed. The growth of these cells that had been incubated in the same manner as above in the absence of ferulic acid-CD inclusion complex I was also observed. From the degree of the growth of the cells, the antimicrobial ability of the chemicals tested was evaluated. The results are shown in Table 4 below, in which "+" means that colonies were formed, "++" means that numerous colonies were formed, W-" means that a few colonies were formed, and means that no colony was formed. Obviously, it is known from Table 4 that the synergistic anti- microbial effect was obtained by the method of the present invention.
- 1 5 - Table 4-1
Test Group Growth Ferulic Acid Chemical(s) Added pH B st E S1 of Cells H S L A _ Not Added 7.0 ++ ++ ++ ++ ++ ++ ++ ++ Glycine 2000 ppm 7.0 ++ ++ ++ ++ ++ ++ ++ ++ Glycine 3000 ppm 7.0 + + ++ ++ ++ ++ ++ ++ Green Tea Extract 100 ppm 6.8 ++ ++ ++ ++ ++ ++ ++ ++ Green Tea Extract 200 ppm 6.7 ++ + + + + + + + Protamine 100 ppm 7.4 ++ ++ ++ ++ ++ ++ ++ ++ Protamine 200 ppm 7.4 + + + + + + + + Polylysine 200 ppm 7.5 ++ ++ ++ ++ ++ ++ ++ ++ Polylysine 300 ppm 7.5 + + + + + + + + Citric Acid + Na-Lactate 0.1 % 5.6 ++ ++ ++ ++ ++ ++ ++ ++ Acetic Acid + Na-Malate 0.1 % 5.5 + + + + + + + + Acetic Acid + Na-Citrate 0.1 % 5.5 + + + + + + Malic Acid + NaLactate 0.1 % 5.5 ++ ++ ++ ++ ++ ++ ++ ++ Malic Acid + Na-Citrate 0.1 % 5.5 ++ ++ ++ ++ ++ ++ ++ ++ Lactic Acid + Na-Acetate 0.1 % 5.5 + + ++ ++ ++ ++ ++ ++ Table 4-2
Test Group Growth of Cells Ferulic Acid Chemicals Added pH B St E S1 H -S L A Ferulic Acid 6.5 + + ++ ++ ++ ++ ++ -CD inclusion Glycine 2000 ppm + complexI Citric Acid + ppm NaLactate 0.1 % 5.5 + + + + + + Glycine 3000 ppm + Acetic Acid + Na-Malate 0.1 % 5.5 Green Tea Extract 100 ppm + Acetic Acid + Na-Citrate 0.1 % 5.5 Green Tea Extract 200 ppm + Malic Acid + Na-Lactate 0.1 % 5.
Protamine 100 ppm + Malic Acid + NaCitrate 0.1 % 5.
Protamine 200 ppm + Lactic Acid + Na-Acetate 0.1 % 5.
Polylysine 200 ppm + Citric Acid + NaLactate 0.1 % 5.
Polylysine 300 ppm + Acetic Acid + Na-Malate 0.1 % 5.
- - +/ +/- - - - +/ +/- - - + Table 4-3
Test Group Ferulic Acid Chemicals Added Ferulic Acid -CD inclusion complex 1 300 ppm 9 0Q 1 11 1 Glycine 2000 ppm + Citric Acid + Na-Lactate 0.1 % Glycine 3000 ppm + Acetic Acid + Na-Malate 0.1 % 5.2 5.2 Green Tea Extract 100 ppm + Acetic Acid + NaCitrate 0.1 % Green Tea Extract Malic Acid + Na-Lactate 0.1 % Protamine 100 ppm Malic Acid + NaCitrate 0.1 % Protamine 200 ppm Lactic Acid + Na-Acetate 0.1 Polylysine 200 Citric Acid + Na-Lactate 0.1 Polylysine 300 Acetic Acid + Na-Malate 0. 1 % ppM + ppM + 5.2 200 ppm + 5.2 5.2 5.2 5.2 Growth of Cells pH B St E S1 H S L A +/- +/-I- + + + a,,, Example 6:
600 g of rice were washed and then dipped in water, to which added were 10.6 g of ferulic acid-CD inclusion complex I obtained in Example 1 and 1. 2 g of buffer comprised of acetic acid and sodium malate at a ratio of 1:2. Then, the rice was boiled and stored at 3M to evaluate the storage stability of the boiled rice. The number of ordinary microbes living in the thus stored rice was counted according to the Food Sanitation Act. Rice that had been boiled in the same manner as above, without adding ferulic acid-CD inclusion complex 1 thereto, was also stored and tested also in the same manner as above. The two data were compared with each other and shown in Table 5 below, from which it is obvious that the rot of the boiled rice was significantly inhibited by the method of the present invention.
Table 5
Sample Number of Living Ordinary Microbes (cells/g) 0 hr 37 hrs Ferulic Acid Not Added (Control) 1. 2 X 10 Ferulic Acid Added (the Invention) lo> Example 7:
7.8 X 10' 3. 2 X 103 Boiled fish paste products were produced according to an ordinary method, except that 500 ppm of ferulic acid, 100 ppm of polylysine and 0.5 % of buffer (PH 7.0) composed of citric acid and sodium citrate were added thereto. These were stored at WC for 4 days to evaluate the storage stability thereof.
During the storage, the number of the living ordinary microbes in the stored products was counted everyday in the same manner as in Example 6. The results - 1 9 - are shown in Table 6 below, from which it is obvious that the rot of the f ish paste products was effectively inhibited by the method of the present invention.
Table 6
Samp 1 e Number of Living Ordinary Microbes (cells/g) 1 day 2 days 3 days 4 days Ferulic Acid Not Added (Control) Ferulic Acid Added (the Invention) 3. 1 X 101 6. 8 X 10' 2. 1 X 102 3.4 X 103 6.5 X 104 1. 3 X 10' Example 8:
A cabbage was cut irregularly to pieces and seasoned with salt water, and the same amount of 2 % salt water was added thereto to prepare saltseasoned cabbage. In the same manner as above, except that 500 ppm of ferulic acid, 100 ppm of chi tosan and 0. 5 % of buf f er (PH 5. 5) comprised of lact ic acid and sodium lactate were added to the 2 % salt water, salt-seasoned cabbage was prepared. The two salt-seasoned cabbage samples were stored at 20t for one week to evaluate their storage stability. The number of the living ordinary microbes in each of the thusstored samples was counted in the same manner as in Example 6. The results are shown in Table 7 below, from which it is known that the sample processed according to the method of the present invention did not become turbid and was prevented from being rotted.
71 - 2 0 - Table 7
Sample Tested Item --- 2 days 4 days 7 days Ferulic Acid Not Added Turbidity +/- ++...
(control) Number of Living Microbes 4.0x104 5.4x106 8.9x107 Ferulic Acid Added Turbidity - - +/ (the Invention) Number of Living Microbes 3.1x103 6.2x103 4.1x104 Number of Living Ordinary Microbes: cells/g Example 9:
One g of ferulic acid and one g of sodium ascorbate were added to 350 g of minced pork, 180 g of minced beef, 150 g of lard, 30 g of edible salt, 0. 1 g of sodium nitrite, 2. 0 g of sodium metaphosphate, 2. 0 g of polyphosphate, 225 g of ice water, 4. 5 g of sugar, 1. 8 g of sodium glutamate, 10 g of egg albumen powder and 30 g of starch, kneaded, filled in an artificial easing having a net diameter of 8.0 mm, heated at WC for 60 minutes and then cooled to obtain sausage samples. Control sausage samples were prepared in the same manner as above, except that ferulic acid and sodium ascorbate were not added.
These samples were sliced to 1 to 2 mm slices and left as they were for hours in a light room, whereupon the change, if any, in the color of the slices was observed. The control sausage slices begun to fade in about 2 hours, while the sausage slices prepared by the method of the present invention did not almost fade even after 5 hours.
-2 2 -
Claims (3)
1. A freshness retaining agent for food, characterized by containing ferulic acid in the form of its inclusion complex with cyclodextrin.
2. The freshness retaining agent for food as claimed in claim 1, which contains ferulic acid or an inclusion complex of ferulic acid with cyclodextrin along with a PH-adjusting buffer.
3. A method for retaining the freshness of food, characterized by bringing food into contact with an aqueous solution containing the freshness retaining agent for food as claimed in claim 2 and having been adjusted to have PH of from 3 to 10.
- 2 3 -
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13080294A JPH07313129A (en) | 1994-05-23 | 1994-05-23 | Freshness preservative for food |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9501773D0 GB9501773D0 (en) | 1995-03-22 |
| GB2289676A true GB2289676A (en) | 1995-11-29 |
| GB2289676B GB2289676B (en) | 1997-11-26 |
Family
ID=15043057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9501773A Expired - Fee Related GB2289676B (en) | 1994-05-23 | 1995-01-30 | Freshness retaining agent for food |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH07313129A (en) |
| AU (1) | AU675369B2 (en) |
| CA (1) | CA2140170A1 (en) |
| DE (1) | DE19501221A1 (en) |
| FR (1) | FR2719979A1 (en) |
| GB (1) | GB2289676B (en) |
| HU (1) | HUT73619A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013025606A3 (en) * | 2011-08-15 | 2013-07-11 | "Ab Mauri Food Inc." | Natural mold inhibitor for bakery products and method of using same |
| US11659844B1 (en) | 2016-08-12 | 2023-05-30 | Zee Company I, Llc | System for increasing antimicrobial efficacy in a poultry processing tank |
| US11839858B1 (en) | 2016-02-17 | 2023-12-12 | Zee Company I, Llc | Peracetic acid concentration and monitoring and concentration-based dosing system |
| US12064732B2 (en) | 2016-02-17 | 2024-08-20 | Zeco, Llc | Methods and related apparatus for providing a processing solution for a food processing application |
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|---|---|---|---|---|
| JP3953499B2 (en) * | 2001-02-19 | 2007-08-08 | ハウス食品株式会社 | Processed food preparation method and retort food |
| JP3844700B2 (en) * | 2001-02-19 | 2006-11-15 | ハウス食品株式会社 | Processed food preparation method and retort food |
| JP4605949B2 (en) * | 2001-07-26 | 2011-01-05 | 太陽化学株式会社 | Degradation preventive agent for flavor components |
| JP5121761B2 (en) * | 2009-03-18 | 2013-01-16 | 上野製薬株式会社 | Food shelf life improving agent and food shelf life improving method |
| EP2301368A1 (en) * | 2009-09-08 | 2011-03-30 | Mars, Incorporated | Composition for prevention against spoilage by microorganisms and uses and products related thereto |
| JPWO2013035804A1 (en) * | 2011-09-08 | 2015-03-23 | カルピス株式会社 | Method for inducing germination of spore-forming bacteria |
| JP2013179933A (en) * | 2012-03-05 | 2013-09-12 | Takara Kasei Co Ltd | Storage duration improver for food |
| CN108948230B (en) * | 2018-08-01 | 2020-11-17 | 陕西师范大学 | Water-soluble beta-cyclodextrin amidated derivative, synthetic method and application in oxidation resistance and antibiosis |
| CN108623711B (en) * | 2018-08-07 | 2020-07-28 | 西北农林科技大学 | Ferulic acid-cyclodextrin covalent coupling compound and preparation method and application thereof |
| CN109744310A (en) * | 2019-02-02 | 2019-05-14 | 浙江省农业科学院 | BPH resistant rice variety antisepsis antistaling agent and fresh-keeping of vegetables method |
| CN109953113A (en) * | 2019-04-30 | 2019-07-02 | 广西壮族自治区农业科学院 | Edible cornstarch film antistaling agent and preparation method thereof, application and fruit and vegetable preserving method |
| CN110786374A (en) * | 2019-11-11 | 2020-02-14 | 中国农业大学 | Ferulate-containing fruit and vegetable sterilization and fresh-keeping agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0215169A1 (en) * | 1984-03-14 | 1987-03-25 | Seiwa Technological Laboratories, Limited | Cyclodextrin inclusion compound and process for its preparation and use |
| US5008254A (en) * | 1982-09-03 | 1991-04-16 | Weibel Michael K | Sugar beet pectins and their use in comestibles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05168449A (en) * | 1991-12-26 | 1993-07-02 | Meiyuu Sangyo Kk | Food preservative and food preservation using the same |
| JP2983386B2 (en) * | 1992-07-21 | 1999-11-29 | 長谷川香料株式会社 | Flavor deterioration inhibitor for food and drink and its use |
| JPH06199733A (en) * | 1993-01-04 | 1994-07-19 | Sansho Seiyaku Co Ltd | New clathrate compound and use thereof |
| JPH0717898A (en) * | 1993-06-30 | 1995-01-20 | Taishiyoo Technos:Kk | Production of hydroxycinnamic acid improved in water solubility |
-
1994
- 1994-05-23 JP JP13080294A patent/JPH07313129A/en active Pending
- 1994-12-15 AU AU80478/94A patent/AU675369B2/en not_active Ceased
-
1995
- 1995-01-13 CA CA 2140170 patent/CA2140170A1/en not_active Abandoned
- 1995-01-13 HU HU9500117A patent/HUT73619A/en unknown
- 1995-01-17 FR FR9500457A patent/FR2719979A1/en active Granted
- 1995-01-17 DE DE1995101221 patent/DE19501221A1/en not_active Withdrawn
- 1995-01-30 GB GB9501773A patent/GB2289676B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008254A (en) * | 1982-09-03 | 1991-04-16 | Weibel Michael K | Sugar beet pectins and their use in comestibles |
| EP0215169A1 (en) * | 1984-03-14 | 1987-03-25 | Seiwa Technological Laboratories, Limited | Cyclodextrin inclusion compound and process for its preparation and use |
Non-Patent Citations (1)
| Title |
|---|
| WPI Abstract Accession No 94-269390/33 and JP610099733 A * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013025606A3 (en) * | 2011-08-15 | 2013-07-11 | "Ab Mauri Food Inc." | Natural mold inhibitor for bakery products and method of using same |
| US11839858B1 (en) | 2016-02-17 | 2023-12-12 | Zee Company I, Llc | Peracetic acid concentration and monitoring and concentration-based dosing system |
| US12064732B2 (en) | 2016-02-17 | 2024-08-20 | Zeco, Llc | Methods and related apparatus for providing a processing solution for a food processing application |
| US11659844B1 (en) | 2016-08-12 | 2023-05-30 | Zee Company I, Llc | System for increasing antimicrobial efficacy in a poultry processing tank |
| US11968988B1 (en) | 2016-08-12 | 2024-04-30 | Zeco, Llc | System for increasing antimicrobial efficacy in a poultry processing tank |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT73619A (en) | 1996-08-28 |
| AU675369B2 (en) | 1997-01-30 |
| FR2719979A1 (en) | 1995-11-24 |
| GB9501773D0 (en) | 1995-03-22 |
| DE19501221A1 (en) | 1995-11-30 |
| GB2289676B (en) | 1997-11-26 |
| CA2140170A1 (en) | 1995-11-24 |
| JPH07313129A (en) | 1995-12-05 |
| AU8047894A (en) | 1995-11-30 |
| FR2719979B1 (en) | 1997-02-21 |
| HU9500117D0 (en) | 1995-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19990130 |