Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
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73299-28
FRESHNESS RETAINING AGENT FOR FOOD
FIELD OF THE INVENTION
The present invention relates to a freshness retain-
ing agent for food and to a method of retaining the freshness
of food using the 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 by
using same.
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 contain-
ing 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 acid-containing preparation free from the above-
mentioned problems.
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73299-28
On the other hand, sulfur dioxide-containing prepara-
tions 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
desired.
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-microbial activity are effective in neutral 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.
SUMMARY OF THE lN-v~NlION
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.
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73299-28
Specifically, the present invention provides a
freshness retaining agent for food characterized by containing
ferulic acid in the form of its inclusion complex of cyclo-
dextrin, a freshness retaining agent for food characterized by
containing ferulic acid or an inclusion complex of ferulic acid
with cyclodextrin along with a pH-adjusting buffer, and a method
of retaining the freshness of food characterized by bringing
food into contact with the freshness retaining agent as it is
or an aqueous solution containing the freshness retaining agent.
Preferably the aqueous solution has a pH value 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 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 trans-isomer 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 critical
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 critical. Anyhow, in order to attain the
effect of the present invention, the agent may contain 10 % by
weight or more of ferulic acid. To conveniently formulate
preparations containing ferulic acid according to the present
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73299-28
invention, the purity of the acid is preferably 50 % by weight
or more.
As cyclodextrin to be used for forming an inclusion
complex of ferulic acid, a-, ~ -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-mark: Isoelite, 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 concentra-
tion 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 weight 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 CDr 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,
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-
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 inclusion complex
may be combined with anti-microbial 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 5,000 ppm
based on the weight of the food.
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 ppm 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 fruits 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 may be combined with anti-microbial and
anti-oxidative substances suitable for food such as ascorbic
acid, sodium ascorbate, citric acid, sodium citrate, salt
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73299-28
(i.e. sodium chloride), phytic acid, plant-derived polyphenols,
polylysine, etc., at any desired ratio, by which the combina-
tions 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 cooled 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
5,000 ppm in terms of ferulic acid. It is recommended to
combine the agent with an emulsifying agent suitable for food
(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 ppm or more, preferably from 100 to 5,000 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
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73299-28
.
recommended to combine the agent with ascorbic acid, sodium
ascorbate, plant-derived polyphenols, citric acid, sodium
citrate, protein hydrolysates, vitamine E, rosemary extract,
etc., by which the anti-oxidative 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 5,000 ppm in terms of ferulic acid,
along with one or more anti-microbial substances chosen from
among chitosan, glycine, ethanol, various tea extracts (includ-
ing 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 ppm or more, preferably from 100 to 5,000 ppm.
In other preparations than the alcoholic preparation, the
ferulic acid content may be generally 0.1 % by weight or more,
preferably from 1 to 10 %.
Where ferulic acid is used in the form of an aqueous
solution (solution
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214017~
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- ~-lactone, 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 dihydrogenphospha-te, sodium dihYdrogenpyrophosPhate, trisodium phosphate, itaconic acid, phytic
acid, ketoglutaric acid, etc. One or more of these are used singly or in
combination, to adiust the pH of the aqueous ferulic acid-containing solution.
The pH adiustment for food to which the agent of the present invention
is applied and the pH adiustment 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
214017U
of the food itself is adiusted to fall within the range of from about 3.0 to
about 12, according to the pH adiustment of the present invention. For the
latter. the pH of ferulic acid or a solution (contact solution) containing
ferulic acid dissolved therein is adiusted 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 liquid-to-powder mixing means may be employed. In addition.
the acid and other substances may be dissolved or dispersed in a solvent such aswater 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
21~017()
73299-28
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 cyclo-
dextrin 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 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:
50 g of ferulic acid having a purity of 98 % and 450
g of maltosyl cyclodextrin mixture (trade-mark: 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 ~-CD were dissolved in one liter of
hot water, and the resulting solution was dried, using a spray-
ing drier, also to obtain a CD inclusion complex of ferulic
acid. This is referred to as ferulic acid-CD inclusion complex
II.
21~017U
73299-28
Each of these two ferulic acid-CD inclusion complex
was added to l00 ml of water at 10C, while stirring, to have
a ferulic acid content therein of one g, whereupon the
solubility of the inclusion complex was observed. On the other
- 9a -
21~0170
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 non-
processed ferulic acid did not almost dissolve in water.
Example 2:
Ferulic acid-CD inclusion complex I 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
minutes. These were then stored for 3 days at 10C, 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.
-1 O-
2140170
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tt
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2140170
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 noodleswas prevented by the method of the present invention.
Table 2
Ferulic Acid Chemical Added Raw Japanese Raw Buckwheat Chinese
Noodles Noodles Noodles
Not Added - + + + + + + + + +
Na Ascorbate + + +
Allyl Isocyanate + + +
Phytic Acid + + +
0.1 % -- +/- +/- +/-
Na Ascorbate - - -
Allyl Isocyanate
Phytic Acid
+ + + : Thickly browned.
+ : Browned.
+ / - : Browned only a little.
- : Not browned.
Example 4:
6000 ppm of ferulic acid-CD inclusion comPlex Il obtained in Example 1
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21~0170
and 2000 ppm of ferulic acid were separately combined with 100 ppm of vitamin E,100 ppm of emulsifying agent, 500 ppm 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 60C
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 -
2140170
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-1 4-
21~0170
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, Iactic acid, sodium lactate, citric acid and sodium citrate, as
indicated in Table 4 below. The mixtures were separately added to a tryptosoy-
agar 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 Sl),Hansenula anomala
(hereinafter referred to as H), SaccharomYces cerevisiae (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 30C, 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 anti-
microbial 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, ~+/-~ 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.
2140170
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-- 21~0170
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--1 7 -
2140170
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2140170
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 37C to evaluate the storage stability of the
boiled rice. The number of ordinary microbes living in the thus stored rice wascounted according to the Food Sanitation Act. Rice that had been boiled in the
same manner as above. without adding ferulic acid-CD inclusion complex I
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 7.8 x 107
Ferulic Acid
Added (the Invention) 10> 3.2 x 103
Example 7:
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 20C 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
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2140170
are shown in Table 6 below, from which it is obvious that the rot of the fish
paste products was effectively inhibited by the method of the present invention.
Table 6
Sample Number of Living Ordinary Microbes (cells/g)
1 day 2 days 3 days 4 daYs
Ferulic Acid
Not Added (Control) 3.1 x 104 6.8 x 107 - -
Ferulic Acid
Added (the Invention) 2.1 x 102 3.4 x 103 6.5 x 104 1.3 X106
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 salt-seasonedcabbage. In the same manner as above. except that 500 ppm of ferulic acid, 100ppm of chitosan and 0.5 % of buffer (pH 5.5) comprised of lactic acid and
sodium lactate were added to the 2 X salt water, salt-seasoned cabbage was
prepared. The two salt-seasoned cabbage samples were stored at 20C for one
week to evaluate their storage stabilitY. The number of the living ordinary
microbes in each of the thus-stored samPles was counted in the same manner as inExample 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.
- 2 0 -
21~0170
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U~ o o
,
ax x
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2140170
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 casing having a net
diameter of 8.0 mm. heated at 80C 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
5 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 notalmost fade even after 5 hours.
