# Patent

## Title
Dyeing agent, dyeing solution and method for dyeing strawberry

## Abstract

This application is a continuation of application, Ser. No. 07/599,840, filed Oct. 19, 1990, now U.S. Pat. No. 5,116,628.

## Background
The present invention relates to a process for producing liquid egg having a reduced cholesterol content and to food containing the liquid egg thus produced.

Demand for food having a low cholesterol content has been increased not only as a diet for treating patients with arteriosclerosis, but also as health food for normal healthy people. In this respect, although eggs are excellent food, they contain a large amount of cholesterol. Therefore, it is desirable to reduce the cholesterol content of eggs.

As means for reducing and cholesterol content of food, direct extraction of cholesterol with various solvents has been proposed. For example, solid-liquid extraction of cholesterol contained in liquid or powdered egg with an organic solvent is known. Examples of this extraction are disclosed in Japanese Patent Kokoku No. 46-42944 and Japanese Patent Kokai No. 47-19062. However, there are various disadvantages in the above extraction with an organic solvent. For example, since cholesterol is normally extracted together with other fats and oils, the resulting food product has a very low fat and oil content. Particularly, in liquid or powdered egg, triglycerides, pigments and the like are extracted together with cholesterol and, therefore, its characteristic flavor is lost, which results in deterioration of its commercial value. Further, there is the possibility that the remaining solvent influences the human body. Therefore, it is at best questionable say that the above extraction is suitable for practical use.

Japanese Patent Kokoku No. 62-51092 proposes a process for removing cholesterol from powdered egg by contacting the powdered egg with supercritical CO.sub.2. However, since powdered egg itself has an extremely inferior flavor in comparison with that of liquid egg, there is a disadvantage that the use of the resulting egg product is limited.

Heretofore, extraction of various organic materials with a supercritical fluid has been known and practical examples thereof include decaffeination of coffee, extraction of hop extract and the like. However, it has been considered that extraction with a supercritical fluid would be ineffective for extraction of a substance from a material containing a large amount of water such as liquid egg.

Under these circumstances, a process is proposed for reducing the cholesterol content of liquid egg without a deterioration in the flavor thereof. It has been unexpectedly found that extraction with a supercritical fluid is applicable for reducing the cholesterol content of liquid egg.

That is, one object of the present invention is to provide a process for producing liquid egg having a reduced cholesterol content.

Another object of the present invention is to provide a food containing the liquid egg thus produced.

These objects as well as other objects and advantages of the present invention will become apparent to those skilled in the art from the following description.

According to the present invention, there is provided a process for producing liquid egg having a reduced cholesterol content which comprises contacting the liquid egg with a supercritical fluid to extract cholesterol from the liquid egg. The present invention also provides food whose raw material is liquid egg having a reduced cholesterol content produced by the above process.

Liquid egg to be used as a raw material in the process of the present invention may be either liquid whole egg or liquid egg yolk, or a mixture thereof. Liquid egg may be any commercially available one and, frozen liquid egg can also be used by thawing it.

As the supercritical fluid, CO.sub.2, N.sub.2 O, ethane, propane and the like can be used in the present invention, but CO.sub.2 is preferred in view of its safety with food. In the present invention, "supercritical CO.sub.2 " used as the extraction solvent of the cholesterol, is defined as CO.sub.2 in a state above its critical point, i.e., at about 31.degree. C., under a pressure of 72 kg/cm.sup.2, upon conducting extraction. Particularly, CO.sub.2 at a temperature of 32.degree. to 47.degree. C. and at a pressure of 120 to 270 kg/cm.sup.2 is preferred in the present invention.

For conducting the process of the present invention, the liquid egg is brought into contact with the supercritical fluid in a wetted wall column system rather than a normal packed column system because, when the latter system is employed, the liquid egg is bubbled, which makes the operation difficult. By selecting the above conditions, it becomes possible to extract cholesterol from liquid egg which contains a large amount of water.

On the other hand, other fatty ingredients are also contained in an extract in addition to cholesterol, and the main components of the other fatty ingredients are neutral fats and the like which have a large influence on flavor and taste. Accordingly, in the separation of the extract, it is preferred to selectively separate a fraction containing a large amount of cholesterol at a first stage under the conditions of a pressure of 50 to 200 kg/cm.sup.2 and a temperature of not less than 40.degree. C., followed by recovering a fraction which contains the other fatty ingredients as the main components at a second stage by changing the conditions, normally, at a pressure lower than that of the first stage separation, preferably not more than 70 kg/cm.sup.2 and at a temperature of 30.degree. to 60.degree. C. Preferably, the amount of cholesterol in the first stage fraction is in the range of 5 to 75%, and the amount of cholesterol in the second stage fraction is up to several %. The main components of the second stage fraction are other fatty ingredients.

Then, if the second stage fraction is returned to liquid egg to be used as a raw material of the extraction, flow of liquid egg along the wetted wall column is improved. Further, if it is added to the resulting liquid egg having a reduced cholesterol content, flavor and taste can be further improved. Accordingly, in the present invention, a part or all of the second stage fraction can be re-used for either or both of the above purposes.

According to the process of the present invention, 50% or more of the cholesterol contained in the liquid egg used as a raw material is removed. However, the resulting liquid egg having a reduced cholesterol content of the present invention has good taste and flavor comparable to fresh eggs and can be used as it is, or it can be frozen for storage. Further, it can be dried by a conventional drying method such as freeze drying, vacuum drying, spray drying, drum drying or the like to use as a raw material for other food products.

The liquid egg of the present invention can be used according to the same manner as that for fresh eggs and conventional egg products. Further, the liquid egg of the present invention can be used together with fresh eggs and/or conventional egg products.

For example, the liquid egg of the present invention can be used for preparing various dishes such as scrambled eggs, egg soup, eggs with bacon, omelet, thick custard soup, coating for fried food and the like. Further, the liquid egg of the present invention can be used as a raw material for various food products such as mayonnaise, egg custard, bread, biscuits, crackers, cakes, cookies, pies, ice cream, noodle, pasta, confectionary, drink and the like.

As described hereinabove, according to the present invention, the liquid egg having a reduced cholesterol content can be obtained without deterioration of flavor and taste and, thereby, serve as a diet for treating patients with hypercholesterolemia as well as health food for normal healthy people.

The following Examples further illustrate the present invention in detail, but are not to be construed to limit the scope thereof.

Liquid egg yolk a 1 kg which had the cholesterol content of 1.2% and was obtained by thawing commercially available frozen liquid egg was fed into a wetted wall column of 30 mm in inner diameter and 1500 mm in length from the top thereof, and CO.sub.2 at the temperature of 35.degree. C. and the pressure of 200 kg/cm.sup.2 was introduced into the wetted wall column from its bottom to bring CO.sub.2 into contact with the liquid egg to conduct extraction. The CO.sub.2 containing the extract effused from the top was firstly subjected to a first stage separation in a separator maintained at the temperature of 35.degree. C. and the pressure of 150 kg/cm.sup.2 and, then, it was further subjected to a second stage separation in a separator maintained at the temperature of 45.degree. C. and the pressure of 50 kg/cm.sup.2.

In the first stage separation, a fraction of 13 g was recovered and, in the second stage separation, a fraction of 126 g was recovered. On the other hand, liquid egg yolk of 826 g was recovered from the bottom of the wetted wall column.

As a result of analysis, it was found that the fraction recovered in the first stage separation contained cholesterol of 45.0% and the amount of cholesterol in the liquid egg yolk recovered from the bottom was 0.36%. The removal ratio of cholesterol was 75.0%.

The fraction recovered at the second stage separation was admixed with the liquid egg yolk recovered from the bottom to obtain the desired liquid egg yolk having the cholesterol content of 0.64%.

When the liquid egg yolk thus obtained was admixed with commercially available liquid egg white so that the composition of the resulting mixture was the same as that of fresh egg, scrambled egg was prepared by using the mixture. As a result, no difference in flavor and taste was found between the scrambled egg thus prepared and that prepared by using fresh egg.

According to the same manner as that described in Example 1, a fraction of 9 g was recovered from a first stage separation and a fraction of 86 g ,was recovered from a second stage separation except that 1.5 kg of liquid whole egg which had a cholesterol content of 0.4% was used instead of liquid egg yolk.

As a result of analysis, it was found that the fraction recovered from the first stage separation contained cholesterol of 32.0% and the amount of cholesterol in liquid whole egg recovered from the bottom was 0.13%. The removal ratio of cholesterol was 70%.

No bubbling liquid whole egg was observed during the operation. When scrambled egg was prepared by using the resulting liquid whole egg recovered from the bottom, no difference in flavor and taste was found between the scrambled egg and that prepared from normal liquid whole egg.

According to the same manner as that described in Example 1, 8 kg of the desired liquid egg yolk having a reduced cholesterol content was obtained by using 10 kg of liquid egg yolk. The removal ratio of cholesterol was about 70%.

Analytical data of the liquid egg yolk used as the raw material and the resulting liquid egg having a reduced cholesterol content are shown in Table 1. ______________________________________ Liquid egg yolk Liquid egg yolk used as raw having reduced Items        material    cholesterol content ______________________________________ Water (%)    50.0        58.9 Protein (%)  14.9        17.3 Lipid (%)    32.0        21.1 Carbohydrate (%) 0.7         0.8 Ash (%)       1.6         1.9 Cholesterol (%) 1.2         0.36 ______________________________________

The following food was prepared by using the liquid egg yolk having a reduced cholesterol content (hereinafter referred to as low cholesterol liquid egg yolk) thus obtained.

Liquid egg white (270 g) and small amounts of sugar and salt were added to the low cholesterol liquid egg yolk (100 g) and the mixture was mixed with a beater. The mixture was baked on a frying pan with a small amount of salad oil to prepare an omelet (omelet A). Likewise, according to the same manner, an omelet (omelet B) was prepared except that fresh eggs were used instead of the low cholesterol liquid egg yolk and liquid egg white. The cholesterol content of omelet A was about 30% of that of omelet B.

Flavor and taste of these omelets were organoleptically evaluated by 10 panelists. The results are shown in Table 2. The figures in Table 2 are the numbers of panelists that agreed to the evaluation. ______________________________________ Evaluation      Omelet A  Omelet B ______________________________________ Better flavor   6         4 Better taste    5         5 Better body     2         8 Better chewing  4         6 Better overall  5         5 evaluation ______________________________________

As seen from Table 2, although omelet A had somewhat plain flavor and taste in comparison with omelet B, no inferior flavor and taste was found.

A mixture of egg white (300 g) and sugar (250 g) was frothed by agitating with a beater. Separately, a mixture of the low cholesterol liquid egg yolk (400 g), sugar (250 g) and water (100 g) was frothed by agitating with a beater. The frothed latter mixture was added to the former and they were mixed. Then, low gluten wheat flour (500 g) was admixed with the resulting mixture. A small amount of vanilla essence was added and the mixture was baked in an oven to prepare a sponge cake (sponge cake A). Likewise, according to the same manner, a sponge cake (sponge cake B) was prepared except that conventional liquid egg yolk was used instead of the low cholesterol liquid egg yolk. The cholesterol content of sponge cake A was about 30% of that of sponge cake B.

Flavor and taste of these sponge cakes were evaluated according to the same manner as that described with respect to the omelet. The results are shown in Table 3. ______________________________________ Evaluation   Sponge cake A Sponge cake B ______________________________________ Better flavor 7           3 Better taste 6           4 Better body  4           6 Better chewing 4           6 Better overall 6           4 evaluation ______________________________________

As seen from Table 3, no substantial difference in flavor and taste was found between sponge cakes A and B.

Whole egg (100 g), the low cholesterol liquid egg yolk (120 g) and sugar (180 g) were mixed and milk (600 g) was added thereto with preventing bubbling. The mixture was stirred. Vanilla essence (0.5 g) and a small amount of rum were added thereto and 150 ml portions of the mixture were distributed into cups. The cups were cooked in an oven at 150.degree. to 160.degree. C. for 40 minutes to prepare a custard pudding (pudding A). Likewise, according to the same manner, a custard pudding (pudding B) was prepared except that conventional liquid egg yolk was used instead of the low cholesterol liquid egg yolk. The cholesterol content of pudding A was about 48% of that of pudding B.

Flavor and taste of these puddings were evaluated according to the same manner as that described with respect to the omelet. The results are shown in Table 4. ______________________________________ Evaluation     Pudding A Pudding B ______________________________________ Better flavor  6         4 Better taste   6         4 Better body    4         6 Better chewing 5         5 Better overall 6         4 evaluation ______________________________________

As seen from Table 4, no substantial difference in flavor and taste was found between puddings A and B.

According to the formulation as shown in Table 5, a mayonnaise was prepared by uniformly mixing the low cholesterol liquid egg yolk, sugar, salt, powdered mustard, pepper, paprika and one half of vinegar, adding dropwise the remaining vinegar and salad oil to the mixture with agitating to obtain an emulsified mixture and then grinding the mixture with a colloid mill for several seconds to prepare a mayonnaise (mayonnaise A). Likewise, according to the same manner, a mayonnaise (mayonnaise B) was prepared except that conventional liquid egg yolk was used instead of the low cholesterol liquid egg yolk. The cholesterol content of mayonnaise A was about 30% of that of mayonnaise B. ______________________________________ Mayonnaise Ingredients          A (%)    B (%) ______________________________________ Conventional liquid egg yolk --       18.0 Low cholesterol liquid egg yolk 18.0     -- Vinegar              9.4      9.4 Sugar                2.2      2.2 Salt                 1.3      1.3 Powdered mustard     0.9      0.9 Pepper               0.1      0.1 Paprika              0.1      0.1 Salad oil            up to 100 up to 100 ______________________________________

Flavor and taste of these mayonnaises were evaluated according to the same manner as that with respect to the omelet. The results are shown in Table 6. ______________________________________ Evaluation    Mayonnaise A Mayonnaise B ______________________________________ Better flavor 6           4 Better taste  6           4 Better body   4           6 Better smoothness 5           5 Better overall 6           4 evaluation ______________________________________

As seen from Table, no substantial difference in flavor and taste was found between mayonnaises A and B. When both mayonnaises were allowed to stand at 50.degree. C. for 10 and 20 days, no substantial difference in appearance was found between mayonnaises A and B.

## Claims

1. Food whose raw material is liquid egg having a reduced cholesterol content obtained by a process comprising the steps of: contacting liquid egg with a supercritical fluid to extract cholesterol from the liquid egg to recover said liquid egg; separating extracted cholesterol and other fat ingredients from the supercritical fluid by adjusting temperature and pressure conditions so that a fraction containing cholesterol of 5 to 75% is obtained in a first stage separation; by further adjusting temperature and pressure conditions so that a fraction containing the other fat ingredients is obtained in a second stage separation; and mixing the fraction obtained in the second stage separation with the recovered liquid egg having a reduced cholesterol content.

2. Food according to claim 1, wherein liquid egg comprises egg yolk.

3. Food according to claim 1, wherein liquid egg to be contacted with the supercritical fluid is that obtained by thawing frozen liquid egg.

4. Food according to claim 1, wherein the supercritical fluid is CO.sub.2.

5. Food according to claim 1, wherein liquid egg is contacted with the supercritical fluid in a wetted wall system.

6. Food according to claim 1, wherein liquid egg comprises liquid whole egg.