JP3280457B2 - Method for producing egg yolk oil monoglyceride - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a process for producing an egg yolk oil monoglyceride having very good taste and odor from egg yolk oil without deteriorating the quality thereof.

[0002]

2. Description of the Related Art Monoglycerides are most frequently used as emulsifiers having excellent performance in the fields of foods, pharmaceuticals, cosmetics, feeds and synthetic resins. Known methods for producing this monoglyceride include a chemical method and an enzymatic method. The former has a drawback that the production of monoglyceride requires a reaction at a high temperature, so that the flavor deteriorates. On the other hand, the latter reacts under milder conditions than chemical methods,
Although the deterioration of flavor is small, the content of monoglyceride in the reaction product is low, and it is necessary to produce it by a secondary process such as fractional distillation, so that satisfactory results have not been obtained.

[0003]

However, monoglycerides prepared from vegetable oils such as olive oil, rapeseed oil and cottonseed oil and monoglycerides prepared from animal fats such as lard and beef tallow by the conventional enzymatic method have the flavor of the raw material fats and oils. Has not yet been obtained in terms of taste and odor with respect to monoglycerides produced by conventional chemical synthesis methods, and the advantage of the enzymatic method is that there is little deterioration in flavor due to heat. It is hard to say that they are making effective use of. Therefore, taste, flavor and oils as raw materials, color, taste,
The development of flavorful monoglycerides has been awaited. In other words, the present invention provides a new method for producing a stable yolk oil monoglyceride at room temperature in a high yield from a yolk oil having a severe deterioration in quality at a high temperature as a substrate by a lipase and an enzymatic method using glycerin containing a trace amount of water. The purpose is to provide.

[0004]

Means for Solving the Problems As a result of repeated studies to solve the above problems, the present inventors have found that a high yield can be obtained by using glycerin containing yolk oil and water as a substrate and reacting with lipase. It has been found for the first time that a monoglyceride having very good bitter taste unique to monoglyceride and having a good taste can be produced, and the present invention has been completed. In the present invention, the yolk oil is a neutral oil produced as a by-product when preparing a purified phospholipid by further extracting only a phospholipid from the yolk lipid obtained by extracting a lipid portion from the yolk with an organic solvent or the like. is there. The lipase used in the present invention can be used without any problem as long as it is a lipase having a high fat and oil decomposition rate, a large amount of monoglyceride produced, and a small amount of diglyceride produced, but it is preferably Pseudomonas fluo Lettuce (Pseudomonas fluorescen)
s) or Chromobacterium biscozam (Chr
A high yield of monoglyceride can be obtained when a lipase produced by O. bacterium viscosum is used. In the present invention, the amount of water in glycerin to be used is suitably in the range of 0.5 to 10% by weight. When it is 10% by weight or more, free fatty acids are produced as by-products, and when it is 0.5% by weight or less. In addition, the activity of lipase decreases, and the yield of monoglyceride decreases. Preferably, the content is 1 to 5%, more preferably 2.5 to 5%.
3.5% by weight is desirable in terms of the monoglyceride yield. In the present invention, the ratio between yolk oil and glycerin is
If the amount of glycerin is too small, the amount of monoglyceride produced is small, and if it is too large, a large amount of unreacted glycerin remains. It is more preferable to carry out the reaction in the range of 5.

The method for producing monoglyceride according to the present invention comprises:
Add glycerin containing water, egg yolk oil, and lipase, and stir at the optimum temperature near the melting point, it is necessary to be in an emulsion state at the start of the reaction, and then adjust the optimum temperature near the melting point of the yolk oil. Maintain and produce yolk oil monoglycerides. With the formation of the egg yolk oil monoglyceride, the state becomes a slurry state or a solidified state, and stirring becomes impossible, but the reaction still proceeds. Therefore, by gradually lowering the temperature, the production rate of yolk oil monoglyceride is increased. However, since the active enzyme is still present in the produced egg yolk oil monoglyceride, it is inferior in stability to monoglyceride produced by a chemical synthesis method. Therefore, in order to produce a monoglyceride which is stable for a long period of time, it is preferable to inactivate and remove the enzyme remaining in the monoglyceride. Therefore, it is preferable to remove the enzyme by passing a solution in which the produced monoglyceride is dissolved in an organic solvent at a content of 10 to 80% through a column filled with silica gel. Examples of the organic solvent include methanol, ethanol, isopropanol, acetone, ethyl acetate, and hexane. The monoglyceride thus obtained is a monoglyceride having a good taste while maintaining the flavor of egg yolk oil as it is and having very little bitterness specific to monoglyceride. Hereinafter, the present invention will be described in detail with reference to examples.

[0006]

【Example】

Example 1 1.42 distilled water was added to glycerin so that the water content was 3%.
g of glycerin (manufactured by Wako Pure Chemical Industries, Ltd.), added about 7500 units of lipase, and stirred for a while. In addition, the mixture was stirred and the reaction was performed at a temperature of 42 ° C. And when the reaction reaches equilibrium,
The reaction was carried out at 5 ° C. and continued until equilibrium was reached. Further, by lowering the temperature to 10 ° C. and 5 ° C., the yield of yolk oil monoglyceride was increased. The reaction product was immersed and dissolved in ethanol so that the concentration of the reaction product became 80%, allowed to stand for 3 hours, passed through a column filled with silica gel, and then ethanol was removed with a rotary evaporator. The yield of the obtained yolk oil monoglyceride was finally 85%. Here, the activity of lipase is 1 under the given reaction conditions.
The amount of enzyme that releases 1 μmol of free fatty acids per minute is 1 u
nit and the composition of the reaction product was determined by Iatroscan analysis. The amount of water is determined by Karl-Fi
It was measured by Scher titration. As a method for measuring the activity of the enzyme, the measurement was carried out based on a method for determining the activity of an enzyme without an emulsifier in the method for measuring lipase activity for industrial use of Japanese Industrial Standards.

Comparative Example 1 Example 1 was repeated except that glycerin having a water content of 0.1% was used.
The same operation as that described above was performed to prepare egg yolk oil monoglyceride. As a result of analyzing the reaction product by Iatroscan, the production rate of monoglyceride was 15%.

Comparative Example 2 Egg yolk oil monoglyceride was prepared in exactly the same manner as in Example 1 except that glycerin having a water content of 12% was used. As a result of analyzing the reaction product by Iatroscan,
The production rate of monoglyceride was 20%, and 50% of free fatty acids was produced as a by-product.

Test Example The taste of the yolk oil monoglyceride obtained in Example 1, Comparative Example 1 and Comparative Example 2, and oleic acid monoglyceride (monoglyceride purity of 90% or more), which is a monoglyceride produced by a chemical synthesis method, were evaluated. Table 1 shows the results of examining the odor and the emulsifying power.

[0010]

[Table 1]

As shown in Table 1, the monoglycerides of the yolk oil of the present invention obtained in Example 1 are the monoglycerides obtained in Comparative Examples 1 and 2, and the monoglyceride oleic acid produced by a chemical synthesis method. Compared to
Excellent performance.

[0012]

According to the method of the present invention, yolk oil monoglyceride, which is an excellent emulsifier, can be produced in a high yield from egg yolk oil, which is a fat and oil which is liable to be deteriorated, and provides a method which is industrially excellent. can do.

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. ⁷ , DB name) C12P 7/64 A23L 1/035 A23L 1/32

Claims (3)

(57) [Claims] 1. A process for producing egg yolk monoglyceride, which comprises using glycerin containing egg yolk oil and water as a substrate, adding lipase, stirring, and forming an emulsion to react. 2. The method for producing egg yolk monoglyceride according to claim 1, wherein the reaction with the lipase is started in an emulsion state and subsequently performed in a slurry state or a solidified state. 3. The method according to claim 1, wherein the water content is 0.5 to 10 with respect to glycerin.
The method for producing egg yolk monoglyceride according to claim 1, which is in terms of% by weight.