JPH0751048B2 - Fat substitute - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel low calorie oil / fat substitute.

[0002]

2. Description of the Related Art Oils and fats have an important function as a heating medium when they are used for heating cooking of fried foods, grilled foods, stir-fried foods and the like. Further, not only in cooking by heating but also in raw food such as dressing, fats and oils impart an aroma and umami unique to fats and oils to the food to be cooked, and are essential ingredients for improving the flavor of foods.

Of course, oils and fats function as nutrients in addition to their cooking function and flavor imparting function, and are essential for the maintenance of life such as the source of calories, the constituents of biological membranes and the regulation of biological functions as essential fatty acids. Needless to say.

However, in recent years, from the nutritional point of view of fats and oils, their excessive intake has often been taken up as a problem as a calorie source. Obesity due to excessive intake of calories is a risk factor for adult diseases, and the problem of obesity in this generation has recently become a problem because oil cooked products tend to be favored by the younger generation.

Fats and oils have a high calorific value of 9 kcal per 4 gcal of protein or saccharide. Therefore, it can be said that adjusting the intake of oils and fats is an effective means for calorie control. However, as described above, oils and fats have important functions in cooking in addition to serving as nutrients. Therefore, if the intake of oils and fats is simply restricted, the eating habits themselves may be greatly affected.

For these reasons, in recent years, so-called fat and oil substitutes having cooking functions and flavors of fats and oils and having a low caloric value have been actively developed.

The flow of development of oil and fat substitutes is roughly divided into 2
It is roughly divided into types. One of them is a method of substituting a part or all of fats and oils for starches, dextrins, proteins or processed products derived from natural products. These fats and oils substitutes are mainly used for raw foods such as margarine, dressing and mayonnaise. It is used in the oil and fat food field, and some oil and fat substitutes have already been used in actual foods. However, these oil and fat substitutes have problems of denaturation and coagulation when heated, and their use is limited to the above.

The other flow is the case of using a chemically synthesized product having physical properties similar to fats and oils, and US Pat. No. 3,600,186.
The fatty acid polyester of sucrose is disclosed in JP-A-1-261.
No. 352 discloses a complex polyol ester such as sucrose, and JP-A No. 64-85040 discloses a triglyceride containing behenic acid.

The reason for the low calories in these fats and oils substitutes is that the structure or the binding mode of the substance is such that it is not easily hydrolyzed by lipase in the living body, and it is difficult to be metabolized. Even if hydrolysis occurs, the melting point is high, so it is difficult to take it into the body.

However, when the calorie is reduced to low calories by the former mechanism, it is said that it is excreted as it is because it is not digested at all in the body and causes anal leakage. Further, the latter has a problem that the physical properties of the liquid oil cannot be maintained because the melting point is high. For the purpose of preventing the anal leak in the former case, a method of binding a fatty acid or the like having a high melting point (JP-A-63-222671), a method of mixing a high-melting-point substance (JP-A-64-34245), etc. Although these have also been tried, the problems with physical properties are still unsolved.

[0011]

[Problems to be Solved by the Invention] As described above,
Although the desired functions of fats and oils are many, such as calorie source, flavor, texture, cooking function, and stability, the fats and oils substitutes that have been developed so far have limited uses, and are used as foods such as physical properties and flavors as fats and oils. Even important parts were missing, and even problems such as anal leak were seen.

Needless to say, as long as it is a substitute for fats and oils as foods, it is required to have physical properties, uses and functions, texture and flavor, and foods that have no problem in use.

An object of the present invention is to provide an oil / fat substitute which has a low calorie content, a flavor and texture required for oils and fats, and a function as a heating medium, and which does not have a problem of anal leakage. .

[0014]

Means for Solving the Problems As a result of intensive studies conducted by the present inventors, triglycerides composed of a branched fatty acid of a certain type are decomposed by hydrolysis even if they are hydrolyzed in the body, as compared with ordinary triglycerides. The branched fatty acid produced has low caloricity because it is difficult to be absorbed in the body, and this substance has a desirable function as an edible oil and fat,
Furthermore, they found that the problem of anal leak did not occur.

The present invention has been completed on the basis of such findings, and is a branched chain having a main chain of 12 to 22 carbon atoms and having an alkyl group introduced at least at the 5th, 9th and 13th positions. It is an oil and fat substitute containing one or more triglycerides containing fatty acids as constituent fatty acids.

As an example of the above triglyceride, a methyl group is introduced at the 5,9,13 position from the terminal carbon of the carboxyl group of myristic acid, which is a linear fatty acid having 14 carbon atoms. It is a triglyceride in which 13-trimethyl-myristic acid is combined with glycerin.

The fatty acid which constitutes the triglyceride of the present invention has a low melting point. Therefore, the triglyceride has the same physical properties as ordinary liquid fats and oils, and has a good flavor and cooking function. When this triglyceride is ingested, even if it is hydrolyzed by lipase, it is not used as energy because it is poorly absorbed from the intestinal tract, it has a low calorie property, and no anal leak phenomenon is observed.

In the present invention, the method for producing the branched fatty acid or its triglyceride is not particularly limited, and known chemical synthesis or enzymatic reaction can be used.

[0019]

【Example】

Example 1 farnesol _{(farnesol. (CH 3) 2} C = CHCH
_{2 CH 2 C (CH 3)} = CHCH 2 CH 2 C (CH 3)
= CHCH ₂ OH) was hydrogenated using a nickel catalyst to obtain hydrogenated farnesol. Red phosphorus and iodine were added to this hydrogenated farnesol, and the mixture was heated and stirred to give an iodide. Add diethyl malonate and sodium ethylate and heat to reflux to extract the dicarboxylic acid and continue heating.
5,9,13-Trimethyl-myristic acid was obtained. Glycerol and p-toluenesulfonic acid were added to this and heated to form triglyceride, which was then purified by Florisil column to obtain 5,9,13-trimethyl-myristate triglyceride.

Example 2 and Comparative Example 1 Four-week-old SD rats were preliminarily bred with a commercially available solid diet, and then an experimental diet having the composition shown in Table 1 was administered by a restricted diet for 2 weeks. After breeding with an experimental diet for 10 days, feces for 2 days were collected, freeze-dried, and lipids in the feces were extracted by the method of Folch to measure the total amount of lipids. Table 2 shows the results of the digestion and absorption rate calculated from the following mathematical formula 1.

[0021]

[Equation 1]

[0022]

[Table 1]

[0023]

[Table 2]

Table 3 shows the results of analysis of the lipid content in feces and the composition thereof.

[0025]

[Table 3]

As shown in Table 2, the absorption rate of the group administered with 5,9,13-trimethyl-myristate triglyceride (Example 2) was 9 in the safflower oil-fed group (Comparative Example 1).
It was as low as 69% against 9%. In addition, as shown in Table 3, in the lipid composition in feces, the free fatty acid content was significantly high in the 5,9,13-trimethyl-myristate triglyceride administration group, and although the hydrolysis of triglyceride occurred, absorption was high. It shows that it did not happen. No anal leak was observed in rats in the group to which 5,9,13-trimethyl-myristate triglyceride was administered.

[0027]

EFFECT OF THE INVENTION Unlike the usual triglyceride, the oil / fat substitute of the present invention exhibits low caloricity because the fatty acid produced by the decomposition is not easily absorbed in the body even if hydrolysis occurs in the body, and further, this oil / fat substitute Has the advantages of flavor and texture required for oils and fats and the function as a heating medium, and that anal leakage does not occur.

Claims (2)

[Claims] 1. A triglyceride comprising a branched fatty acid having a main chain carbon number of 12 to 22 and having an alkyl group introduced at least at the 5,9,13 position as a constituent fatty acid, and contains one or more triglycerides. A substitute for oils and fats. 2. An oil / fat substitute containing one or more triglycerides having 5,9,13-trimethyl-myristic acid as a constituent fatty acid.