JPS63123362A - Quality improving agent for food - Google Patents

Abstract

PURPOSE:To obtain the titled improving agent, containing D- glucosaccharoascorbic acid (salt) and capable of preventing deterioration caused by oxidation, etc., of food and exhibiting excellent effect on sustaining and improving of food quality. CONSTITUTION:An improving agent containing D-glucosaccharoascorbic acid (salt) and preferably further tocopherol. The above-mentioned improving agent in an amount of preferably 0.01-0.5wt% is added to a food, e.g. meat, meat product, fruit, processed fruit, milk, dairy product, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a food quality improving agent containing D-glucosaccharoascorbic acid or a salt thereof, and a food product with improved quality.

BACKGROUND OF THE INVENTION Up to now, L-ascorbic acid, its salts or its ester derivatives, erythorbic acid, its salts, etc. have been used as food quality improving agents.

Structure of the invention D-glucosaccharoascorbic acid (
Chemical name D-erythrohexo-2-enaloo 1,4-
Lactone) is a new compound that has not been described in any literature, and unlike ascorbic acid or erythorbic acid, it has a structural feature of having a carboxyl group in its molecule. The present inventors focused on the fact that this compound exhibits excellent antioxidant effects, and as a result of conducting extensive studies with the aim of applying it to foods, we found that it exerts various excellent quality-improving effects on various foods. They discovered this and completed the present invention.

That is, the present invention provides (i) a food quality improver containing D-glucosaccharoascorbic acid or a salt thereof, and (ii) a food product containing D-glucosaccharoascorbic acid or a salt thereof. be.

D-glucosaccharoascorbic acid used in the present invention is
Using 2-keto D-glucaric acid or its salt derived from D-glucose, or its 2゜3-〇-acetal or ketal as a raw material, it is treated with an acid (for example, hydrogen chloride, sulfuric acid, etc.) in water or an organic solvent. It can be manufactured by processing. In the present invention, the compounds can be used not only in the free acid form, but also in their alkali metal salts (for example sodium salts) or alkaline earth metal salts (for example calcium salts).

The quality improver of the present invention contains D-glucosaccharoascorbic acid or a salt thereof in powder form, or in a solvent (e.g., water, ethanol, etc.), emulsifier (e.g., glycerin fatty acid ester, sucrose fatty acid ester, propylene glycol fatty acid ester, etc.). esters, etc.), thickeners, stabilizers, and further diluted with burnt alum, wheat flour, and calcium carbonate. The quality improver of the present invention can also be used in various food additives (e.g. seasonings, acidulants, sweeteners).

It can also be used in combination with one coloring agent, one coloring agent, one flavoring agent, preservative, bactericide, and antioxidant.

Foods targeted for quality improvement in the present invention include animal and vegetable foods and processed products thereof. Specifically, for example, oil or fat-containing food, meat or meat products, fruit or fruit processed products.

Examples include vegetables or vegetable processed products, milk or dairy products, miso, soybean oil, and beverages such as beer and wine.

The quality improving agent of the present invention exhibits an antioxidant effect on fats and oils or fat-containing foods, and the quality improving agent added to fats and oils and fat-containing foods is prevented from deterioration due to oxidation. Such oils and fats include, for example, unsaturated fatty acids such as oleic acid, linoleic acid, lyluic acid, cottonseed oil, safflower oil, coconut oil, corn oil, soybean oil, sesame oil,
olive oil.

Examples include natural fats and oils such as peanut oil, palm oil, beef tallow, lard, fish oil, whale oil, and processed foods containing these. Generally, when the purpose is to prevent oxidation of oils and fats,
The amount added is approximately 0.01 to 1.0% by weight, preferably 0.02 to 0.5% by weight, and may be appropriately selected depending on the target food. The inventors
It has also been found that by using D-glucosaccharoascorbic acid in combination with tocopherol, which is conventionally known as an antioxidant in foods, an even more excellent antioxidant can be obtained. Tocopherol used in combination is
Mention may be made of α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol or mixtures thereof (for example, natural tocopherols obtained from vegetable oils, germs, etc.). The amount of tocopherol used is the same as that conventionally added to foods as an antioxidant, for example approximately 0.005 to 1.0% by weight, preferably 0.
01 to 1.0% by weight.

Other applications of the quality improving agent of the present invention include improving the quality of meat or meat products.

The quality improver of the present invention exhibits a discoloration preventing effect on meat, and the meat to which the improver is added is inhibited from browning during storage and maintains its bright red color. In addition, the quality improver of the present invention exhibits the action of promoting color development and preventing fading of meat products, promoting the action of color formers such as nitrates and nitrites, and on the other hand, preventing fading of the developed color. Examples of meat include beef,
Examples include pork, mutton, chicken, minced meat, and fresh seafood. Meat products include hams, sausages, bacon, hamburgers, grilled pork, dried fish, smoked products, and salted products made from these meats. Examples include stuffed meat and paste products. In addition, the quality improver of the present invention has the effect of suppressing the formation of nitrosamines, which have safety issues, in processed meat products, and suppresses the formation of trimethylamine, which is the odor of rotting fresh fish, in fresh fish. It has the effect of When adding a quality improver to meat or meat products, the amount and method of addition can be selected as appropriate depending on the target food. O1~! , 0% by weight, preferably 0.0
Add directly from 2 to 0.5% by weight or from 0.01 to
Methods include spraying a 1.0% aqueous solution, preferably a 0.02 to 0.5% aqueous solution onto the food, or immersing the food in this aqueous solution.

Another application example of the quality improving agent of the present invention is improving the quality of dairy products.

The quality improver of the present invention exhibits an effect of preventing the occurrence of off-odor 8 and quality deterioration in milk or dairy products, and the milk or dairy products to which the quality improver of the present invention has been added exhibits an oxidized odor during storage. Beef tallow ingredients, stale odor 1 The occurrence of sunlight odor is suppressed,
Decomposition of vitamin A in milk or dairy products is also inhibited.

Milk or dairy products include raw milk, raw goat's milk, cow's milk, special milk, pasteurized goat's milk, skimmed milk, processed milk, cream, concentrated milk, and evaporated milk.

Sweetened condensed milk, sweetened skimmed condensed milk, whole milk powder, skim milk powder, sweetened milk powder, milk drink 1 fermented milk, lactic acid bacteria drink, butter, cheese,
Foods whose main ingredients include ice cream, ice milk, lacto ice, and milk are included.

When adding a quality improver to milk or dairy products, the amount and method of addition can be appropriately selected depending on the target food, but it is added in an amount of 0.01 to 1.0% by weight, preferably 0.01 to 1.0% by weight during the manufacturing process. It is preferable to add 0.5% by weight.

Examples of objects to be modified include fruits, vegetables, and processed products thereof.

The quality improving agent of the present invention exhibits effects on fruits and fruit processed products to prevent discoloration, fading, and flavor deterioration. Fruits and fruit processed products such as apples,
Examples include peaches, bananas, apricots, pears, plums, and their frozen products, refrigerated products, beverages, canned goods, and dried fruits.

The amount and method of adding the quality improver can be selected as appropriate depending on the target food, but during the manufacturing process 0.01~! ,
Methods include directly adding 0% by weight, spraying a 0.01-1.0% aqueous solution onto foods, or immersing the foods in this aqueous solution.

Furthermore, the present inventors have found that by using D-glucosaccharoascorbic acid in combination with salt or (and) citric acid or (and) malic acid, the present inventors can achieve much better prevention of discoloration and fading. It has also been found that it has the effect of preventing flavor deterioration. The mixing ratio of common salt or (and) citric acid or (and) malic acid to D-glucosaccharoascorbic acid used in conjunction with D-glucosaccharoascorbic acid is 0.1 to 5.
0 times amount, preferably 0.1 to 20 times amount, citric acid is 0.
1 to 100 times, preferably 0.2 to 50 times, malic acid should be 0.1 to 100 times, preferably 0.2 to 50 times, and the specific blending ratio is determined by the target food. It may be selected as appropriate.

In addition, the quality improver of the present invention exhibits effects of preventing discoloration, fading, and flavor deterioration on vegetables and vegetable processed products. Vegetables and processed vegetable products, such as burdock, butterbur, eggplant, radish, radish, yam, pine mushroom, potato, sweet potato, cauliflower, cabbage, lettuce, carrot, and frozen products, refrigerated products, beverages, and canned goods made from these ingredients.

Examples include dried vegetables. The amount and method of adding the quality improver to vegetables and processed vegetable products are the same as when adding it to fruits and processed fruit products, and may be appropriately selected depending on the target food.

Furthermore, beverages can be cited as an example of the object whose quality is improved by the present invention.

The quality improver of the present invention can be used for beer or wine,
Prevents deterioration such as turbidity, precipitation, discoloration, and deterioration of flavor.

The amount of the quality improver of the present invention added is beer or grape wine I
5-100 mg for Q, preferably 10-70 m
g, and may be added as appropriate during the manufacturing process.

Hereinafter, the present invention will be explained in more detail with reference to Examples.

Example 1 Quality Improver 1 0.4 g of D-glucosaccharoascorbic acid was dissolved in ethanol to a total volume of 50% to prepare Quality Improver 1 for oils and fats or oil-containing foods.

Soybean oil [peroxide value (hereinafter abbreviated as PO■) = 2,
85 meq/kg] 20 ha with quality improver l and L-ascorbic acid, BIT (Dibutyl
Soybean oil containing the amounts shown in Table 1 was prepared by adding 0.5 ml of each ethanol solution of hydroxytoluene. This additive-containing soybean oil was measured using an oil and fat stability tester (AOM measuring device, Kuramochi Scientific Instruments Manufacturing Co., Ltd.).
Oxidation was carried out under the conditions of 97.8±1° C. and an air flow rate of 2.33 cells/sec, and the PoV was measured over time.

The results are shown in FIG.

Table 1 In general, the stability of oils and fats is expressed by the time it takes for the POV of the sample oil to reach a certain value, and the larger the time value, the higher the stability. In Figure 1, POV is l 00 meq
/kg, L-ascorbic acid (Experiment No. (2)) takes 20 hours, BHT (Experiment No.
o, (3)) was 11 hours, whereas the quality improver l of the present invention (experiment No. (1)) was 28 hours, far superior to conventionally known antioxidants. It exerted an anti-oxidant effect.

Example 2 Quality improver 2 0.4 g of D-glucosaccharoascorbic acid and 0.4 g of natural tocopherol were dissolved in ethanol, and the total amount was 5
A quality improver 2 for fats and oils or foods containing fats and oils was prepared.

To linoleic acid (POV: 0.5 meq/kg) at 20 o'clock, 0.5 g of each ethanol solution of quality improver 2, BIT, and natural tocopherol were added.
Linoleic acid containing the compounds shown in the table was prepared.

This additive-containing linoleic acid was oxidized using the same apparatus as in Example 1 under the same conditions, and POv was measured over time. The results are shown in FIG.

In Table 2, Figure 2, when comparing the time until pov reaches 100 meq/kg, BIT (experiment No. (2))
for 3.5 hours, natural tocopherol (Experiment No., (3
)) is 2.5 hours, whereas the quality improver 2 of the present invention (experiment No. (1)) shows 5.4 hours, which is far superior to conventionally known antioxidants. It exerted an anti-oxidant effect.

Example 3 To 20ra of lard (POV: 2.5meq/kg), 0.5% of the quality improver 2 prepared in Example 2 and the ethanol solution of natural tocopherol were added to produce lard containing the amounts shown in Table 3. prepared. This additive-containing lard was oxidized using the same equipment as in Example 1 under the same conditions, and the Pov was measured over time. The results are shown in FIG.

In Table 3 and Figure 3, comparing the time required for pov to reach 20 meQ/kg, natural tocopherol (Experiment No.
, (2)) was 25 hours, whereas the quality improver 2 of the present invention showed an excellent antioxidant effect for 30 hours.

Example 4 The lean part of tuna was cut into pieces of 1.5 cm x 1.5 cm x 6 cm, immersed in a 1.0% aqueous solution of D-glucosaccharoascorbate disodium salt for 2 minutes, and heated to 5 to 8°C.
The meat was stored in a refrigerator for 21 hours, and changes in the color of the red meat were examined with the naked eye. As controls, untreated lean meat parts and lean meat parts immersed in a 1.0% sodium L-ascorbate aqueous solution for 2 minutes were prepared. The storage results are shown in Table 4.

Table 4 Example 5 Pork is used as the raw material, and as shown in Table 5, D-glucosaccharoascorbate disodium salt is added along with additives such as salt, sodium nitrite, and sodium polyphosphate in the production process of balk sausage. (added in two different amounts and without additives as a control), balk sausages were produced. After production, store it in a refrigerator at 5 to 8 degrees Celsius for 20 hours.
Cut this into 15nn+ thick pieces and put them in a polyethylene bag.
The change in color during storage at room temperature (under irradiation with fluorescent light) was measured using a color difference meter using the a value according to the Hunter display method. The larger the a value, the greater the degree of red color. Figure 4 shows the change in a value over time. The time on the horizontal axis of this graph is the elapsed time after cutting to a thickness of 15 mm.

As can be seen from the following, the sausage to which the quality improving agent of the present invention was added had a stronger degree of color development and less fading than the control.

Table 5 Lean pork mince 400g stuffed in a casing (vinylidene chloride tube with a diameter of 30mm) Heating (80°C for 40 minutes) ↓ Cooling (under running water) Example 6 Quality improver 3 D-glucosaccharoascorbic acid 10g and salt 10g
Add water to 1000! and produced fruit quality improver 3.

D-glucosaccharoascorbic acid 1% aqueous solution 1000
- and quality improver 3.1000- are placed in a glass container, the sliced peaches are immersed therein, and the container is sealed tightly. Thereafter, changes in the color of both the soaked liquid and the vegetables were observed with the naked eye.

As a control, sliced peaches were immersed in a 1% aqueous solution of water and salt, a 1% aqueous solution of L-ascorbic acid, and an aqueous solution of 1% L-ascorbic acid and 1% common salt, each of which was sealed tightly. The results are shown in Table 6. This indicates that the quality improving agent of the present invention has an effect of preventing browning of the peaches, and the liquid containing the quality improving agent of the present invention was prevented from generating cloudiness 1.

Table 6 Note) ◎...No discoloration○...Slight discoloration△...Browning ! A seed medium 20d consisting of 2.0% D-glucose, 1.0% peptone, 1.0% dry yeast and 0% CaCOs2 was dispensed into a 200TnQ Erlenmeyer flask,
It was steam sterilized in advance at 120°C for 20 minutes. In this flask, add 2.5% D-sorbitol and 1.0% peptone.
, grown on a slant medium consisting of 1.0% yeast extract, 2% Ca CO30, and 2.0% agar at 28°C for 4 days. Pseudogluconobacter satsurikiroketogenes strain K591S (FEFtMP-8481, IFo
A loopful of strain 1 of strain 14464) was inoculated and cultured at 30° C. for 2 days with shaking (20 rpm) to obtain a seed culture solution. Dispense medium 200TR1 with the same composition as the seed medium into an IQ volume Erlenmeyer flask, sterilize it in the same manner as above, and add seed culture medium I to this flask.
After transplanting O-, shaking culture was performed at 30°C for 3 days.

The obtained culture solution contained 2-19,4 mg/M/,
Keto D-glucaric acid was produced.

This culture solution 1600 d was centrifuged (7,00 Orpm).

10 minutes), remove the precipitate containing bacterial cells, and remove the supernatant.
I got d. When the supernatant is cooled to 4° C. and allowed to stand for 3 days, amorphous 2-keto D-glucaric acid dicalcium salt crystals are formed. The generated crystals were filtered through a glass filter (No.
3) Collect a small amount of cold water on top.

Washed with methanol and ethyl ether and dried under reduced pressure over phosphorus pentoxide. In this way, 18 g of sicalcium 2-keto D-glucarate trihydrate was obtained. The analytical values of the obtained crystals were as follows.

Melting point = 152-157°C (decomposed) Elemental analysis value (%) cstt, calculated value as oa-Ca-3H,O: C, 24,00; H, 4,03; Ca
, 13.35 Actual value: C, 23,96; H, 4,16
; Ca, 13.00 Specific rotation: [α]25=-12
, 3° (c=1.065%.

O, IN HCI: Immediately after dissolution) = +7.9° (c = 1.065%.

0, IN HCI: after stabilization) Reference Example 2 50.0 g of crude sicalcium salt of 2-keto D-glucaric acid [3 water of sicalcium salt of 2-keto D-glucaric acid determined by high performance liquid chromatography] Japanese (Cs
Contains 85.1% as HeOsCa・3H*O), 0
．． 1417 mol] was suspended in 800% acetone, 17.19 g of 97% sulfuric acid (0.17 mol) was gradually added dropwise while stirring at room temperature, and the mixture was further stirred for 10 hours after the dropwise addition was completed. Insoluble matter was filtered off, washed with about 300 ml of acetone, and combined with the filtrate. Concentrate to dryness under reduced pressure, and add 100% to the residue.
- concentrated hydrochloric acid was added and heated at 70°C for 20 minutes. The reaction solution was concentrated to dryness under reduced pressure, 100 d of water and 0.5 g of activated carbon were added to the residue, heated at 70°C for about 5 minutes, the activated carbon was removed by filtration, and the mixture was concentrated to dryness under reduced pressure. Ether-acetonitrile was added to the residue, the insoluble matter was filtered out, washed with a small amount of dichloromethane, and dried under reduced pressure in a desiccator.
2.2 g of D-glucosaccharoascorbic acid was obtained.

Yield: 82.4%.

Melting point: 188-189°C (decomposition) (Recrystallized from acetone-benzene).

The quality improving agent of the present invention effectively prevents deterioration of food products due to oxidation, etc., and exhibits excellent effects in maintaining and improving the quality of food products.

[Brief explanation of the drawing]

Figure 1 shows the time-dependent change curve of peroxide value of soybean oil containing various additives in the experiment of Example 1, and Figure 2 shows the curve of peroxide value of soybean oil containing various additives in the experiment of Example 2. FIG. 3 shows a curve of the peroxide value of acid over time, and FIG. 3 shows a curve of the peroxide value of lard containing various additives in Example 3. In addition, FIG. 4 shows Example 5.
Degree of redness (a value) of balk sausage in the experiment
The graph shows the change curve over time. Mackerel fish fake fine (meq/kq) Oxidation) K price (meq/kq) M! L acid AL proboscis west (meq/kg)0
Profit.

Claims (6)

[Claims] (1) A food quality improving agent containing D-glucosaccharoascorbic acid or a salt thereof. (2) The quality improving agent according to claim (1), wherein the food is an oil or fat-containing food. (3) Claim No. 1 in which the food is meat or meat products (
The quality improving agent described in item 1). (4) The quality improving agent according to claim (1), wherein the food is a fruit or a fruit processed product. (5) The quality improving agent according to claim (2), further containing tocopherol. (6) Foods containing D-glucosaccharoascorbic acid or its salt.