JP3106217B2 - Lecithin and edible fat / oil composition containing the lecithin - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a lecithin and an edible oil / fat composition. More specifically, various types of crude lecithin, including soybean lecithin used for food and industrial purposes, are modified, and improved lecithins having improved heat stability, flavor and the like, and lecithins produced by conventional production methods More particularly, the present invention relates to an edible oil / fat composition which is more excellent in the effect of preventing food from being sputtered in cooking foods, hardly causes browning upon heating, and is excellent in storage stability, flavor and the like, as compared with the edible oil / fat composition containing.

[0002]

BACKGROUND ART Crude lecithin derived from plants such as soybean lecithin is usually a mixture of simple lipids such as phospholipids, glycolipids, and triglycerides, and contains free sugars and pigments as trace components. In terms of phospholipid composition, taking soybean as an example, phosphatidylcholine (PC), phosphatidylethanolamine (PE),
Phosphatidylinositol (PI) is a main component,
Others include phosphatidic acid (PA), lysophosphatidylcholine (LPC), and the like. In terms of sugar composition, in addition to sucrose, raffinose and stachyose α-galacto-oligosaccharides are present, and a total amount of carbohydrates is about 5%. Furthermore, these crude lecithins have an amino group content of 40 to 50% by weight in terms of glycine, which is an amino acid, as measured in a ninhydrin reaction.

[0003] These crude lecithins are inexpensive and readily available natural emulsifiers and are therefore widely used for food applications. In particular, in cooking foods, edible oil / fat compositions obtained by adding and dissolving lecithin to vegetable oil are used. ing. This is because lecithin is particularly excellent in the effect of preventing food material from spattering (oil splash) and releasing effect. However, since crude lecithin contains various impurities as described above, it has a disadvantage that fats and oils are easily browned by heating. Because of this drawback, crude lecithin has limited use and application.

Conventionally, to solve this drawback, a method has been known in which lecithin is treated with an enzyme (phospholipase D) to convert most of the phospholipid into phosphatidic acid (PA) (JP-A-2-186946). . This is an excellent method for obtaining lecithin that is not easily browned. However, since the main component is PA, when added alone to vegetable oil or the like, not only precipitation easily occurs upon heating, but also enzymes and reaction by-products are produced in the production method. Solvent fractionation for removal is required.

Also, a method of dissolving lecithin in a low-polar organic solvent such as hexane or chloroform and contacting water or aqueous alcohol to obtain a lecithin from which water-soluble substances have been removed (Japanese Patent Laid-Open No. 3-141288), (JP-A-3-15342)
Is also known. The main substance removed by these methods is carbohydrate, which will be described in detail in the following Examples.Lecithin from which sugars have been removed can suppress browning by heating as compared with crude lecithin, but its effect is somewhat limited. The problem of heat browning has not been solved. Moreover, as described above, lecithin that has been subjected to an operation of removing saccharides or increasing the phospholipid content for the purpose of preventing heat browning, etc., has the properties of lecithin when added to edible oil, such as sputtering prevention properties and releasability. Is not improved as compared with normal crude lecithin, and another problem occurs in that flavor and storage stability are impaired.

[0006]

SUMMARY OF THE INVENTION The present invention improves the heat resistance of lecithin (it does not discolor even when heated),
An object of the present invention is to provide a lecithin further improved in emulsifying action, spatter preventing action and mold release properties which are inherent functions of lecithin, and an edible oil / fat composition containing the lecithin.

[0007]

Means for Solving the Problems The present inventors have solved the conventional problems relating to lecithin, and have developed an edible oil / fat composition which has an excellent effect of preventing spattering of foodstuffs in cooking foods and which is less likely to brown during heating. As a result of intensive research on substances contained in lecithin and causing caustic browning, we have reduced the content of amino groups related to the amino-carbonyl reaction, which is considered to be the main reaction of the caustic browning reaction. Removal of α-galacto-oligosaccharides present in the form of stachyose or stachyose is not only extremely useful for preventing the browning of lecithin by heating, but also when using the lecithin in an edible oil / fat composition, the effect of preventing sputtering and the storage stability of the oil / fat are improved. The present invention was completed by finding that the property increases.

Accordingly, the lecithin of the present invention is characterized in that the content of α-galacto-oligosaccharide is less than 0.1% by weight and the content of amino group is less than 10% by weight in terms of glycine when measured in a ninhydrin reaction. . Still further, the present invention relates to the present invention, wherein the content of α-galacto-oligosaccharide is 0.1% by weight.
The present invention relates to an edible oil / fat composition comprising 0.1% by weight or more of lecithin having an amino group content of less than 10% by weight in terms of glycine when measured in a ninhydrin reaction.

As described above, the lecithin of the present invention has an α-galacto-oligosaccharide content of less than 0.1% by weight and an amino group content in crude lecithin in terms of glycine when measured in a ninhydrin reaction.
By reducing the amount to less than 10% by weight, the heating stability of lecithin is improved, and not only the browning by heating is minimized, but also when added to edible fats and oils, it has been conventionally known as an effect of lecithin. The effect of preventing sputtering is further improved, and at the same time, the storage stability of fats and oils is remarkably improved.

One of the features of the present invention is that α-galacto-oligosaccharides present in lecithin in the form of raffinose and stachyose are removed to less than 0.1% by weight. It is not necessary to remove saccharides other than galactooligosaccharides, and the presence of these saccharides is rather effective in improving quality such as improving the flavor of lecithin. At this time, the content of α-galacto-oligosaccharide was 0.1
If the content is more than 10% by weight, the desired effect of modifying lecithin of the present invention cannot be sufficiently obtained. Another important feature of the present invention is the reduction of amino groups, which is also an important item. When the content of amino groups contained in crude lecithin is measured in a ninhydrin reaction, it must be reduced to less than 10% by weight in terms of glycine. The effect of modifying lecithin intended by the present invention cannot be obtained.

As a method for producing lecithin of the present invention, for example, a small amount of an adsorbent such as activated clay or silica gel is added to an alcohol solution of lecithin, and the mixture is stirred and mixed. Then, the adsorbent is removed by filtration and the solvent is distilled off. Thus, α-
Galacto-oligosaccharides and optionally lecithins with reduced amino groups can be obtained. Alternatively, a hydrous alcohol solution of lecithin is passed through a non-polar styrene-vinylbenzene type synthetic resin adsorbent, and the α-galacto-oligosaccharide is washed with a hydrous alcohol, and then a fraction containing little PE with anhydrous alcohol. By eluting as lecithin and distilling off the solvent, it is possible to obtain lecithin in which α-galacto-oligosaccharide and, in some cases, amino groups are reduced and PC and PA amounts are within predetermined ranges. However,
The manufacturing method is not necessarily limited to the method described here.

Lecithin as a raw material can be used as long as it is usually used as crude lecithin. For example, paste or powder obtained from vegetable oil seeds such as soybeans, rapeseed, corn, sunflower, and palm can be used. Undehydrated gums can also be used. Egg yolk lecithin is more expensive than these and is not preferred as a raw material for food applications, which is the main object of the present invention, but can be used similarly.

By adding the lecithin of the present invention to edible fats and oils in an amount of 0.1% by weight or more, the edible food has an excellent effect of preventing spattering of foodstuffs during heating of foodstuffs, is less likely to brown during heating, and has excellent oxidation stability. An oil or fat composition can be obtained. These effects have been recognized by the present inventors as phenomena through experiments, and the reason for this is not clear in detail, but the reduction of reactive groups related to the amino-carbonyl reaction considered as the main reaction of the heating browning reaction is considered. It is presumed to be based on The amount of lecithin to be added depends on the type of edible oil and fat, but is usually preferably about 0.1 to 20% by weight. Examples of the fats and oils used in the present invention include rapeseed oil, soybean oil, cottonseed oil, safflower oil, palm oil, rice oil, sesame oil, known animal and vegetable fats and oils such as lard and the like, which are hydrogenated or fractionated, and further transesterified oils. They can be used alone or in combination of two or more. Further, to the edible oil / fat composition of the present invention, it is possible to add various antioxidants, flavors, and other emulsifiers such as sucrose fatty acid esters and diglycerides, depending on the purpose of use.

[0014]

EFFECT OF THE INVENTION The lecithin of the present invention removes α-galacto-oligosaccharides and reduces the amino group content, so that not only the heat stability of lecithin is improved due to the synergistic effect of these two, but also an edible oil / fat composition. At this time, the composition has an advantage that it is not only excellent in the effect of preventing the spattering of the food material in the cooking of food but also hardly causes browning at the time of heating and also has excellent oxidation stability. Therefore, compared to the edible oil / fat composition containing lecithin according to the conventional production method, not only can it be used for cooking of light-colored foods that dislike color change during cooking, but also the quality change in the storage of the edible oil / fat composition Can be minimized.

[0015]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. Example 1 An aqueous alcoholic solution of crude lecithin was passed through a nonpolar styrene-vinylbenzene-type synthetic resin adsorbent, α-galacto-oligosaccharide was washed with aqueous alcohol, and lecithin was eluted with anhydrous alcohol to remove the solvent. By distilling off, lecithin with reduced α-galacto-oligosaccharide was obtained. In addition, the obtained lecithin also had reduced amino groups. In order to obtain lecithin containing no sugar (reduced sugar content), the lecithin was subjected to a desugaring treatment by the following operation.
That is, 10 g of lecithin is dissolved in 200 ml of chloroform, and 500 m
Transfer to l-volume separatory funnel. 180 ml of methanol and 75 ml of distilled water are added to this, shaken vigorously and allowed to stand. The lower layer (chloroform layer) was concentrated by an evaporator to obtain a sample. The lecithin used as a sample was crude lecithin (AY lecithin manufactured by Honen Corporation) and high-purity lecithin (PC manufactured by True Lecithin Industry Co., Ltd.)
-70).

About the raw material and the obtained lecithin sample, phospholipid composition, acetone-insoluble part, peroxide value (POV),
The sugar composition was measured. The results are shown in Tables 1 and 2.
The phospholipid composition, acetone-insoluble part, peroxide value (P
OV) was analyzed by the method shown in the standard fat and oil analysis method. The content of the amino group contained in lecithin was measured using a ninhydrin color reaction. That is, lecithin was dissolved in a chloroform-methanol solution, and 0.1%
% Ninhydrin in methanol was added, heated at 70 ° C. for 20 minutes, and the absorbance at 570 nm was measured. The sugar composition in lecithin was determined by "post-column fluorescence detection method using arginine as a reaction reagent". The analysis conditions are shown below. * HPLC conditions Column: Shim-pack ISA-07 / S2504 Mobile phase: 300 mM Boric acid-NaOH pH 8.5 0.
5ml / min Reaction solution: 2% Arginine / 3% Boric acid soln. 0.
5ml / min Column temperature: 70 ° C Reaction temperature: 150 ° C Detector: Fluorescence detector (Ex 320nm, Em 430nm)

[0017] Note 1) Phospholipid composition is the value when total phospholipid is 100%.

The crude lecithin used was a product using soybean as a raw material, and as shown in Table 1, shows a standard analytical value as lecithin. High-purity lecithin is obtained by using crude lecithin as a raw material and increasing the phospholipid content by repeating solvent fractionation (the value of “acetone-insoluble portion” in Table 1 reflects the phospholipid content; The higher the value, the higher the phospholipid content) and, at the same time, the content of PC, which is a component of phospholipids, is increased. Table 1
As is clear from the description, the novel lecithin of the present invention is different in general quality from crude lecithin and high-purity lecithin, and the phospholipid content and PC content are positioned between crude lecithin and high-purity lecithin. It can be called lecithin.

[0019] -: Present in a trace amount * The amino group content indicates glycine-equivalent weight% in ninhydrin color test.

As shown in Table 2, the novel lecithin contains sucrose at the same level as crude lecithin, but does not contain raffinose and stachyose, which are α-galacto-oligosaccharides. The amino group content is less than 10% by weight in terms of glycine as measured by a ninhydrin reaction, and is reduced to 1/4 or less as compared to crude lecithin and 1/2 or less as compared to high purity lecithin. Desaccharideation can remove oligosaccharides from crude lecithin, but also reduces sucrose equivalently. Desaccharification also reduces the amino groups of crude lecithin, but its effect is limited and does not decrease to less than 10% by weight unlike the novel lecithin of the present invention. As described above, the novel lecithin has characteristics in the sugar composition and the amino group content, and a simple desugaring treatment cannot provide a lecithin having such characteristics.

Test Example 1 The novel lecithin obtained in Example 1, crude lecithin,
The desulfated crude lecithin and high-purity lecithin are each dissolved in rapeseed oil at 1% to prepare test oils. Each of these test oils was heated at 180 ° C. for 20 minutes, and the degree of coloring after heating was compared by measuring the absorbance at 520 nm. Table 3 shows the results.

[0022]

As is evident from the results in Table 3, the test oil to which the novel lecithin obtained by removing α-galacto-oligosaccharide from crude lecithin was added, despite the fact that it contained 1.2% sucrose, had a crude lecithin and high purity. Browning by heating is suppressed more than the test oil to which lecithin as well as the deglycosylated crude lecithin is added.

Test Example 2 As in Test Example 1, new lecithin, crude lecithin,
Using a test oil obtained by adding and dissolving 1% of desulfated crude lecithin and high-purity lecithin to rapeseed oil,
An oil splash (sputtering) test was performed. The oil splash (sputtering) test was performed by a filter paper adsorption method.
In this method, a stainless steel petri dish is placed on an aluminum block in a hot block bath, the test oil is poured into the Petri dish, heated, and then a 0.6% by weight sodium caseinate solution is dropped. This is a test method in which the weight of filter oil is adsorbed on the filter paper and the weight of filter oil is determined by the increase in the weight of filter paper. Therefore, the smaller the amount of splashed oil, the better the splash prevention effect.

[0025]

As is clear from Table 4, the amount of spattered oil was about half that of the test oil to which crude lecithin was added, although the test oil to which new lecithin was added contained sucrose. The effect of suppressing is improved.

Test Example 3 Using the test oil to which 1% of each lecithin described in Test Example 1 was added, an oxidative stability test of fats and oils was performed. The AOM test indicated in the standard method for analyzing fats and oils was performed as a test for the oxidation stability of fats and oils. The longer the time shown in the table, the higher the oxidation stability of fats and oils.

[0028]

As is clear from Table 5, the test oils to which new lecithin was added were as shown in Table 1. Although sucrose was contained as shown in Table 2, oxidative stability was about twice that of ordinary crude soybean lecithin, indicating that storage stability was improved.

As is apparent from the above test examples, the oil and fat composition containing the modified lecithin of the present invention has a releasability, an anti-sputtering effect and a storage stability as compared with the conventional oil and fat composition using lecithin. In addition to being excellent in heat absorption, it is possible to minimize heat adsorption (browning).

──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Takeshi Watanabe 1-7-40 Oiwake, Shimizu City, Shizuoka Prefecture (72) Inventor Minako Hiraoka 11-16 Yokosuna Higashi, Shimizu City, Shizuoka Prefecture (58) Fields surveyed (Int. Cl. ^7, DB name) A23J 7/00 JICST file (JOIS) JAFIC file (JOIS)

Claims (2)

(57) [Claims] 1. A lecithin characterized in that the content of α-galacto-oligosaccharide is less than 0.1% by weight and the content of amino group is less than 10% by weight in terms of glycine as measured in a ninhydrin reaction. 2. Lecithin having an α-galacto-oligosaccharide content of less than 0.1% by weight and an amino group content of less than 10% by weight in terms of glycine as measured in a ninhydrin reaction is 0.1% by weight or more. An edible fat / oil composition characterized by the following: