JPH0614712A - Oil and fat having low caloric value - Google Patents

Abstract

PURPOSE:To provide the subject oil and fat containing a specific amount of distearomonolinolein, etc., having excellent taste, flavor and stability, exhibiting low caloric effect owing to the formation of dischargeable decomposition products after digested in vivo and useful for food, etc. CONSTITUTION:The objective oil and fat contains >=30% distearomonolinolein and/or distearomono-alpha-linolenin. Foods such as potato chips can be prepared by using the oil and fat.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to low-calorie fats and oils made from natural vegetable fats and oils and can be used as a general food material by substituting ordinary fats and oils.

[0002]

BACKGROUND ART Obesity is considered as an unfavorable phenomenon for health, but it is quite prevalent in modern society. The main cause is that the intake energy in the diet is more than the consumption energy. Therefore, it is considered effective to prevent obesity by adjusting the calorie value of the food to be taken.

Western-style foods generally contain a high level of fat and give a pleasant taste and texture from the aspect of taste.
However, fat has more than twice the caloric density of carbohydrates and proteins. Therefore, in order to optimize the calorie intake, it is effective to reduce the intake of fat, but to solve the two conflicting problems of reducing the calorie intake from fat without impairing the flavor of food. In order to do so, various proposals have been made.

In US Pat. No. 3,600,186, a polyester of a sugar such as sucrose and a fatty acid such as oleic acid is not digested and absorbed in the body, and its texture and flavor are the same as ordinary fats and oils. , Said polyester can be used as a low calorie fat. However, it has been said that such liquid sucrose polyester has an undesirable side effect so-called anal leak action.

A method for preventing this is described in US Pat.
No. 5,195, filed to add free saturated fatty acid, triglyceride containing saturated fatty acid or sucrose fatty acid ester to sucrose polyester. In this regard, an improved patent has been filed thereafter (Japanese Patent Laid-Open Nos. 63-222671 and 64-2).
533, JP-A-2-227051, etc.).

Many other low-calorie fats and oils have been proposed, but most of them are chemically synthesized products. For example, tricarboxylic acid ester (US Pat. No. 4,508,746), dicarboxylic acid ester (JP-A-62-192339), complex polyol ester (JP-A-1-261352) and polyorganosiloxane (JP-A-2-219541). Issue bulletin).

On the other hand, regarding the digestion / absorption of fatty acids constituting natural fats and oils, it was reported that when tristearin (stearic acid triglyceride) was administered to rats, the digestion / absorption rate was only 20% ( A.J.C
liftord et al. , Journal of
Nutrition, 117, 944, 1986.
, Or a fully hydrogenated soybean oil and a high oleic acid safflower oil were transesterified and reported to be almost completely absorbed (A. Bonan).
ome et al, New England Jou
rnal of Medicine, vol. 318, 1244
Page, 1988).

Under these circumstances, low-calorie fats and oils made from natural raw materials are composed of behenic acid obtained by hydrogenating erucic acid, which is a fatty acid of fats and oils obtained from rapeseeds, which are not commonly used at present, and medium-chain fatty acids. A patent for low-calorie fats and oils using transesterified triglyceride (JP-A-2-17)
99, JP-A-2-158695, JP-A-3-474.
No. 7, etc.) and those using deep-sea fish wax (Japanese Patent Application Laid-Open No. 1-252248).

[0009]

The above-mentioned oil / fat substitute having a structure that does not exist in nature can be easily obtained without being digested or absorbed in the body, but on the other hand, in terms of safety and compatibility with living bodies. However, there are still some concerns, and it is difficult to be accepted by consumers and it is difficult to be used as a general-purpose food material. For this reason, it is low in calories when ingested, and those that can substitute, substitute or substitute for ordinary fats and oils preferably have a fatty acid glyceride structure, and the glyceride consisting of the above-mentioned behenic acid and medium chain fatty acids is a low calorie fat and oil. Although a preferable example, behenic acid, which is a raw material, is a fatty acid that is rarely contained in ordinary general-purpose natural fats and oils, and the fats and oils of products must be expensive. The peculiar odor and flavor deterioration associated with decomposition are extremely difficult.

Therefore, an object of the present invention is to provide a stable low-calorie oil having a structure almost equivalent to that of natural oils and fats, having a safe digestion and no side effects, and having a low digestion and absorption rate, using natural oils and fats as a raw material. To develop.

[0011]

That is, the present invention provides a distearomonolinolein or / and a distearomonoα-
A low-calorie oil containing 30% or more of linolenin. Here, distearomonolinolein is 1,2-distearo-3-linolein (hereinafter SSL).
And 1,3-distearo-2-linolein (hereinafter referred to as SLS), and distearomono α-linolenin is 1,2-distearo-3-α-linolenin (hereinafter referred to as SSLn) and 1,3-distearo-2.
-Α-linolenin (hereinafter referred to as SLnS). The oil and fat of the present invention can be prepared by utilizing various known methods,
For example, soybean oil, hydrogenated fats and oils obtained by completely hydrogenating natural vegetable fats and oils such as rapeseed oil, and transesterification with natural vegetable fats and oils having a high linoleic acid and / or α-linolenic acid content,
If desired, the target component can be obtained by concentrating and purifying.

[0012] When natural vegetable oils such as soybean oil and rapeseed oil are completely hydrogenated, fatty acids such as oleic acid, linoleic acid and α-linolenic acid are converted into stearic acid, and hardened oils and fats containing tristearin as a main component. Become. However, such a hardened oil and fat has a melting point of about 70 ° C. or higher, and is limited when used as a raw material for food applications. In order to make it a more versatile material for food use, it is preferable to subject this hardened oil and fat to a transesterification reaction with liquid oil by a conventional method.

In the present invention, safflower oil, sunflower oil, etc. having a high linoleic acid content, linseed oil, perilla oil, perilla oil, etc., having a high α-linolenic acid content are used as the liquid oil, or a mixture thereof is used. Transesterification with hardened oil and fat containing tristearin as a main component is performed. The transesterification reaction may be carried out by a conventional method, may be carried out non-selectively using a metal alcoholate or a random type lipase as a catalyst, and the position of the glyceride structure, for example, 1-position and 3-position.
Alternatively, a lipase having specificity for the position may be used to selectively carry out. Each of these methods has its own characteristics, and an appropriate method can be selected according to the application of the low-calorie fat of the present invention.

Generally, transesterification products of hydrogenated fats and oils such as tristearin (hereinafter referred to as SSS) and liquid oils such as trilinolein (hereinafter referred to as LLL) are roughly classified into SSS, SSL and SLS, SLL and LS.
It becomes a mixture of four kinds of glycerides of L and LLL. Therefore, in the present invention, distearomonolinolein (SS
L and SLS) or / and distearomono α-linolenin (SSLn and SLnS) at 30% (wt%,
The same shall apply hereinafter), in order to obtain fats and oils containing preferably 50% or more, the blending ratio of the raw materials to be subjected to the transesterification reaction, that is, hydrogenated fats and oils and liquid oil rich in linoleic acid and / or α-linolenic acid content is adjusted. Or alternatively, the reaction product is subjected to purification treatment such as recrystallization, solvent or solvent-free fractionation, simple distillation, or molecular distillation to have 2 molecules of stearic acid and 1 molecule of linoleic acid or α-linolenic acid in the glyceride. The ingredients may be concentrated.

The fats and oils having a specific structure thus obtained are
When a feeding test with rats is performed, it shows low sample efficiency and a high lipid excretion rate, has characteristics as a low-calorie oil and fat, and is a general-purpose semi-solid or solid oil and fat, which can be used as an edible raw material. As an example, when it is used for frying oil of snacks such as potato chips, it is possible to produce a food having low calorie and excellent oxidative stability. Further, when used for whipped cream or frozen desserts, a low-calorie product having no physical or flavor problems can be produced.

[0016]

【Example】

Example 1 200 g of hydrogenated oil obtained by completely hydrogenating soybean oil and 100 g of safflower oil were placed in a four-necked flask, heated and melted, and dried under reduced pressure at 80 ° C. for 1 hour. After 0.9 g of sodium methoxide as a catalyst was added, random transesterification was performed at 80 ° C. for 1 hour under vacuum, and the reaction was stopped by neutralizing with 0.8 g of 75% phosphoric acid aqueous solution. After washing with water and drying under reduced pressure, 30 g of diatomaceous earth was added as a filter aid, and the mixture was filtered through a Buchner funnel lined with diatomaceous earth to obtain 250 g of a reaction product. Hexane (1.5 liters) was added to the reaction product, which was then heated to 50 ° C. to dissolve it, and cooled to 30 ° C. to crystallize a high-melting point triglyceride (main component is SSS) and removed by filtration. Hexane was distilled off under reduced pressure from the filtrate obtained at this time, and deoxidation, decolorization, and deodorization treatments were carried out in accordance with ordinary fat and oil purification methods to obtain 230 g of purified triglyceride.
The result of GLC analysis shows that SSL + SLS is 45%.
Met. The triglyceride composition of this product (hereinafter referred to as SSL45) is shown in Table 1.

Example 2 10 kg of hydrogenated oil obtained by completely hydrogenating soybean oil and 5 kg of safflower oil were used as raw materials and treated in the same manner as in Example 1 to obtain 30
The filtrate obtained by fractionating the high melting point crystals at ℃ was further cooled to 5 ° C., allowed to stand for 20 hours, and then the crystal part (medium melting point section) was fractionated by filtration. The middle melting point classification is Example 1
The solvent was removed and the purification treatment was carried out in the same manner as in 1. to obtain 5 kg of purified triglyceride. Analysis of this triglyceride by silver nitrate TLC and GLC showed that SSL + SLS was 70
%Met. The triglyceride composition of this product (hereinafter referred to as SSL70) is shown in Table 1.

[0018]

[Table 1]

This S was added to 85 parts of fat-free mixed feed for laboratory animals.
When 15 parts of SL70 was added and administered to rats for 1 week, the feed efficiency decreased (FIG. 1). Then, when feces were collected 3 days after administration and acidified by adding hydrochloric acid and then lipid was extracted, 50% of the lipid was stearic acid and 20% was monoglyceride of stearic acid. Then, comparing the intake and excretion of rats, 50% of the fat intake
Was excreted (Fig. 2). From this result, it was confirmed that SSL70 is a low-calorie fat.

In this experiment, SSL and SL
To see the difference in lipid excretion rate depending on the content of S, SSL
70 and control oil 1: 2 and 1: 1 blended oil and SS
Compared to L45. As a result, SSL and SLS are 20
%, The lipid excretion rate is almost the same as the control oil, but 30%
It increased when exceeding 50%, and showed a very high value when exceeding 50%. (Fig. 2, Table 2)

[0021]

[Table 2]

Example 3 800 g of stearic acid and 500 g of linseed oil were dissolved in 5 liters of hexane in advance, and then the mixture was applied to a column packed with 1 liter of lipase (NIPPON NORDISK: “LIPOZYME”) and selectively at 40 ° C. A transesterification reaction was performed. The reaction product is allowed to stand at 30 ° C. for 20 hours,
High melting point components (DG containing stearic acid, MG, etc.) were crystallized and removed by filtration. Next, the filtrate is cooled to 5 ° C. and left standing for 20 hours to crystallize medium-melting-point triglyceride (main component is SLnS), separated by filtration, decolorized with activated clay, and steam distilled at 210 ° C. under reduced pressure. It was deodorized to obtain 500 g of purified triglyceride. This triglyceride was analyzed by silver nitrate TLC and GLC to find that SLnS and a trace amount of SSLn were 50% and SLS.
And the trace amount of SSL was 15%.

15 parts of this purified triglyceride was added to 85 parts of fat-free mixed feed for experimental animals, and the rats were administered for 1 week. Feces were collected 3 days after the administration, acidified by adding hydrochloric acid, and then lipids were extracted. As a result, 80% of the lipids were stearic acid. Next, when comparing the intake and excretion of rats, 60% of the ingested fat was excreted.
It was confirmed that the fats and oils containing SLnS as a main component were low-calorie fats and oils.

Example 4 A potato chip was fried using a purified triglyceride prepared by the same process as in Example 2. As a result of evaluating the flavors of the potato chips and the commercial product by 10 professional panels, 7 people said that the oil and fat of the present invention was good, 2 people who made it equivalent,
Only one person said that the commercial product was good. Also, in the dark, 5
The peroxide value after storage for 3 weeks at 0 ° C is 5.0.
Commercial product: 27.5.

[0025]

EFFECTS OF THE INVENTION The fats and oils according to the present invention are digested in the body, but decomposed products are excreted, so that they are low in calories and excellent in flavor and stability, so that they can be used for foods like ordinary fats and oils. Excellent as a low-calorie fat.

[Brief description of drawings]

1 comparison with the invention (SSL70 (1/2), SSL45 and SSL70) (control: Lard and SSL70)
It is a figure showing feed efficiency when each fat and oil of (1/3)) was made to ingest to a rat.

FIG. 2: Comparison with the present invention (SSL70 (1/2), SSL45 and SSL70) (control: Lard and SSL70).
(1/3)) It is a figure showing the lipid excretion rate when each fat is ingested by a rat.

Claims (2)

[Claims] 1. A low-calorie oil containing 30% or more of distearomonolinolein or / and distearomono-α-linolenin. 2. A food using the low-calorie fat according to claim 1.