JP7078201B1 - Random transesterified oil and plastic fat composition using this as a hard stock - Google Patents

Abstract

It is an object of the present invention to provide a random transesterified oil having a reduced saturated fatty acid content and good physical characteristics for use as a hard stock of a plastic fat composition. Random transesterification oil containing medium-chain triglyceride-bound oil (MCT) as a raw material.

Description

The present invention relates to a random transesterified oil and a plastic oil / fat composition using the same as a hard stock.

So far, many studies have been conducted on reducing the oiliness of plastic oil and fat compositions such as margarine and shortening, and improving melting in the mouth.

When producing a plastic fat or oil composition such as margarine or shortening, the physical characteristics are adjusted by adjusting the melting point, SFC, or the like of the fat or oil used. Generally, in a plastic oil / fat composition, the physical characteristics of the oil / fat are directly linked to the physical characteristics such as spread property at low temperature, stain appearance property of liquid oil at high temperature, melting property in mouth, and graining property. Further, in general, the plastic oil / fat composition has better meltability in the mouth as the blending amount of the low melting point oil / fat such as liquid oil increases.

Therefore, when producing a plastic oil / fat composition, a method of obtaining a certain physical property and good meltability in the mouth is carried out by blending an appropriate amount of a high melting point oil / fat with a low melting point oil / fat mainly composed of a liquid oil.

This high melting point portion is particularly called hard stock, and is greatly involved in the spread property at low temperature, which is important as the physical characteristics of margarine and fat spread, the stain-out property of liquid oil at high temperature, the melt-in-the-mouth property, and the graining property. In addition, hard stock is mainly used as a part of fat and oil compounding in oily foods, and if hardness can be effectively imparted with a smaller amount, the entire compounding of oily foods can be designed more freely, which may be useful. many.

The use of transesterified oils as a hard stock used in plastic oil and fat compositions has been studied (Patent Documents 1 to 6).

Japanese Unexamined Patent Publication No. 2001-139983 Japanese Unexamined Patent Publication No. 2002-253117 Japanese Patent Application Laid-Open No. 2003-003195 Japanese Unexamined Patent Publication No. 2005-113153 Japanese Unexamined Patent Publication No. 2005-120386. Japanese Unexamined Patent Publication No. 2007-28206

The conventional transesterification oil for hard stock has a problem that the content of saturated fatty acid is increased and the melting in the mouth is deteriorated in order to improve the above-mentioned physical characteristics in a small amount.

The challenge with transesterified oils for hardstock is to improve melting in the mouth when used in plastic oil compositions. However, it has been a difficult task to further reduce the saturated fatty acid content of the conventional transesterified oil for hard stock because the function in terms of physical properties is deteriorated.
Therefore, an object of the present invention is to provide a random transesterified oil having a reduced saturated fatty acid content and good physical properties for use as a hard stock of a plastic fat composition.

As a result of diligent research in view of the above circumstances, the present inventor prepared the constituent fatty acid composition and contained medium-chain fatty acid-bound fat (MCT) as a raw material for the random ester exchange oil to obtain the present invention. It came to be completed.

That is, the present invention
(1) For hard stock, in which the saturated fatty acid in the constituent fatty acids is 60% by weight or less, the medium-chain fatty acid-bound fat (MCT) is contained as a raw material for random ester exchange, and the following (A) to (D) are all satisfied. Random ester replacement oil,
(A) The content of saturated fatty acids having 6 to 10 carbon atoms in the constituent fatty acid composition is 0.5 to 10% by mass.
(B) The content of saturated fatty acids having 16 to 22 carbon atoms in the constituent fatty acid composition is 50 to 60% by mass.
(C) Stearic acid content in the constituent fatty acid composition is 20 to 50% by mass.
(D) The mass ratio of stearic acid to the total content of saturated fatty acids having 8 to 10 carbon atoms is 5 to 17
(2) Random transesterified oil for hard stock, which has a rising melting point of 40 ° C or higher and 55 ° C or lower.
(3) Random transesterification oil for hard stock according to (1) or (2), wherein the SFC at 30 ° C. is 20 to 30% and the SFC at 35 ° C. is 15 to 25%.
(4) A plastic oil / fat composition containing 5 to 30% by weight of the random transesterified oil for hard stock of (1) or (2) and 70 to 95% by weight of the liquid oil.
(5) A plastic oil / fat composition containing 5 to 30% by weight of the random transesterification oil for hard stock and 70 to 95% by weight of the liquid oil of (3).
(6) A method for producing a plastic fat / oil composition, which comprises blending 5 to 30% by mass of a random transesterified oil for hard stock and 70 to 95% by mass of a liquid oil according to (1) or (2).
(7) A method for producing a plastic oil / fat composition, which comprises blending 5 to 30% by mass of a random transesterified oil for hard stock and 70 to 95% by mass of a liquid oil according to (3).

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a random transesterified oil having a reduced saturated fatty acid content and good physical properties for use as a hard stock of a plastic fat composition.
The random transesterified oil for hard stock of the present invention has a sufficient function for hard stock use while the content of saturated fatty acid in the constituent fatty acid composition is 60% by mass or less, and the random ester exchange oil for hard stock of the present invention has sufficient functions. When transesterified oil is used as a hard stock of a plastic fat composition, it has the effect of suppressing the occurrence of graining with less stains on the liquid oil and showing good physical properties in terms of melting in the mouth and spreadability at low temperatures. A plastic oil / fat composition can be obtained.
As a preferred embodiment of the present invention, the content of saturated fatty acid in the constituent fatty acid composition is 60% by mass or less, and the rising melting point is 40 ° C. or higher and 55 ° C. or lower, which is low saturation and low melting point, but is used as a hard stock application. It is also possible to give sufficient functions.

The random ester exchange oil of the present invention contains 60% by weight or less of saturated fatty acids in the constituent fatty acids, and contains medium-chain fatty acid-bound fat (MCT) as a raw material for random ester exchange. The medium-chain fatty acid-bound fat (MCT) in the present invention is a fat or oil containing a fatty acid having 6 to 10 carbon atoms as a main component in the constituent fatty acid composition.
The random transesterified oil of the present invention is prepared by random transesterification with a metal catalyst such as sodium methylate or random transesterification lipase.

The random transesterified oil of the present invention satisfies all of the following (A) to (D).
(A) The content of saturated fatty acids having 6 to 10 carbon atoms in the constituent fatty acid composition is 0.5 to 10% by mass.
(B) The content of saturated fatty acids having 16 to 22 carbon atoms in the constituent fatty acid composition is 50 to 60% by mass.
(C) Stearic acid content in the constituent fatty acid composition is 20 to 50% by mass.
(D) The mass ratio of stearic acid to the total content of saturated fatty acids having 8 to 10 carbon atoms is 5 to 17

The random transesterified oil of the present invention contains (A) a saturated fatty acid having 6 to 10 carbon atoms in the constituent fatty acid composition of 0.5 to 10% by mass, preferably 0.5 to 8% by mass. Within such a numerical range, a good texture can be obtained in oil-based foods.

The random transesterified oil of the present invention preferably contains (B) a saturated fatty acid having 16 to 22 carbon atoms in the constituent fatty acid composition of 55 to 59% by mass, more preferably 55 to 58% by mass, still more preferably. Is 55 to 57% by mass.

The random transesterified oil of the present invention preferably has a stearic acid content of 20 to 48% by mass, more preferably 20 to 45% by mass in the constituent fatty acid composition (C).

The random ester exchange oil of the present invention preferably has (D) a content mass ratio of stearic acid of 6 to 17 with respect to the total content of saturated fatty acids having 8 to 10 carbon atoms.

The random transesterified oil of the present invention preferably has a rising melting point of 40 ° C. or higher and 55 ° C. or lower, more preferably 45 ° C. or higher and 55 ° C. or lower.

The random transesterified oil of the present invention preferably has 20 to 30% SFC at 30 ° C. and 15 to 25% SFC at 35 ° C.

The random ester exchange oil of the present invention may be adjusted according to the above-mentioned conditions, but other than the medium chain fatty acid bound oil (MCT), the oils and fats that can be used as the raw material of the ester exchange oil include soybean oil and rapeseed oil. , Corn oil, cottonseed oil, peanut oil, sunflower oil, rice oil, Benibana oil, olive oil, sesame oil, palm oil, palm oil, palm kernel oil and other vegetable fats and oils, milk fat, beef fat, pork fat and other animal fats, and Examples thereof include cured oils, fractionated oils, cured fractionated oils, fractionated cured oils, processed oils and fats that have undergone ester exchange, and mixed oils and fats thereof.
Preferably, vegetable oils such as soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice bran oil, Benibana oil, olive oil, sesame oil, palm oil, and their hardened oils, fractionated oils and hardened fractionated oils, Examples thereof include separately cured oils, processed oils and fats that have undergone ester exchange, and mixed oils and fats thereof.
More preferably, soybean oil, rapeseed oil, corn oil, cottonseed oil, sunflower oil, rice bran oil, Benibana oil, palm oil, and their hardened oil, fractionated oil, hardened fractionated oil, fractionated hardened oil, ester replacement, etc. were applied. Examples thereof include processed oils and fats and mixed oils and fats thereof.
More preferably, soybean oil, rapeseed oil, sunflower oil, palm oil, hydrogenated oils thereof, hydrogenated oils, hydrogenated fractionated oils, hydrogenated fractionated oils, processed fats and oils subjected to ester exchange and the like, and mixed fats and oils thereof are exemplified. can.
Most preferably, soybean oil extremely hydrogenated oil, rapeseed oil extremely hydrogenated oil, sunflower oil, palm oil, palm fractionated oil, and palm extremely hydrogenated oil are used.
Most preferably, any two or more of palm extremely hydrogenated oil, rapeseed extremely hydrogenated oil, soybean extremely hydrogenated oil, high erucic acid rapeseed extremely hydrogenated oil, sunflower oil, palm super olein, and medium chain fatty acid bound oil (MCT). It is to be used in combination.

The random transesterified oil of the present invention is prepared by non-selective transesterification with a metal catalyst such as sodium methylate or a randomized transesterified lipase.

The random ester exchange oil of the present invention can be used as a hard stock for plastic fat and oil compositions such as margarine and shortening, but includes glycerin fatty acid ester, sucrose fatty acid ester, propylene glycol fatty acid ester, polyglycerin fatty acid ester and lecithin. Esters can be appropriately added and used.

The hard stock obtained by using the random transesterified oil of the present invention can produce a plastic fat composition such as margarine and fat spread by blending a liquid oil. Examples of the liquid oil include rapeseed oil, soybean oil, sunflower seed oil, cottonseed oil, peanut oil, rice bran oil, corn oil, safflower oil, capoc oil, sesame oil, evening primrose, and any of these. You may use it.

To exemplify the method for producing the plastic oil / fat composition of the present invention, a mixed oil containing 5 to 30% by weight of the hard stock and 70 to 95% by weight of liquid oil is rapidly cooled and kneaded according to a conventional method. Can be done. If the blending ratio of the hard stock is too small, the stain resistance of the liquid oil at high temperature tends to deteriorate, and if it is too large, the spread property and meltability at low temperature tend to deteriorate.

Examples of the present invention will be shown below, and the present invention will be described in more detail. In the example,% and part both mean mass-based.

(Analysis method)
(Fatty acid composition)
Japan Oil Chemistry Association Standard Oil and Fat Analysis Test Method (1996 edition) 2.4.1. The measurement was carried out according to the method specified in the 2-methylesterification method (boron trifluoride methanol method).
(Rising melting point)
The measurement was carried out according to the method specified in 2.2.4.2 (increased melting point) of the Japan Oil Chemistry Association standard oil and fat analysis test method (1996 version).
(SFC measurement method)
In the measurement of (SFC at each temperature), SFC is measured according to IUPAC.2 150 SOLID CONTENT DETERMINATION IN FATS BY NMR. As the analyzer, "minispec mq20" manufactured by Bruker is used.
(SFC Parallel measurements at each temperature)
In order to evaluate the dissolution characteristics, the fat and oil are held at 80 ° C. for 10 minutes and then at 60 ° C. for 30 minutes to completely dissolve the fat and oil, and then held at 0 ° C. for 1 hour to solidify. Further, the SFC (solid fat content) is measured after holding at a predetermined temperature (10 ° C, 20 ° C, 20 ° C, 30 ° C, 35 ° C, 40 ° C) for 30 minutes.

As the medium-chain fatty acid-bound fat and oil, n-octanoic acid (8 carbon atoms) and n-decanoic acid (10 carbon atoms) are constituent fatty acids, and the weight ratio of these is 60:40, MCT-64 (manufactured by Fuji Oil Co., Ltd.). )It was used. Other raw material fats and oils are blended, 1.5 g of sodium methylate is added as a catalyst to 1.0 kg of the blended fats and oils, random transesterification is performed at 80 ° C. for 30 minutes, and then washing / decolorization / decolorization according to a conventional method. Deodorization was performed to obtain a random transesterified oil. The fatty acid composition of the obtained transesterified oil is shown in Table 1. The rising melting points of the random transesterified oils are listed in Table 2.

The fatty acid composition analysis values (%) were compared.

(Evaluation of analytical values)
-The content of saturated fatty acid in the constituent fatty acid composition is 60% by mass or less (A) The content of saturated fatty acid having 6 to 10 carbon atoms in the constituent fatty acid composition is 0.5 to 10% by mass.
(B) The content of saturated fatty acids having 16 to 22 carbon atoms in the constituent fatty acid composition is 50 to 60% by mass.
(C) Stearic acid content in the constituent fatty acid composition is 20 to 50% by mass.
(D) The mass ratio of stearic acid to the total content of saturated fatty acids having 8 to 10 carbon atoms is 5 to 17
・ The rising melting point is 40 ° C or higher and 55 ° C or lower.

(Discussion in Table 2)
In Examples 1 to 4, the content of saturated fatty acids in the constituent fatty acid composition was 60% by mass or less, all of (A) to (D) were satisfied, and the rising melting point was 40 ° C. or higher and 55 ° C. or lower. ..
-Comparative Example 1 and Comparative Example 3 were fats and oils in which the content of saturated fatty acids in the constituent fatty acid composition exceeded 60% by mass.
-Comparative Examples 1 and 2 were fats and oils that did not satisfy (A), (C), and (D).
-Comparative example 3 was an oil or fat that did not satisfy (D).
-Comparative Example 4 was an oil or fat that did not satisfy (A), (B), (C), and (D).

The SFC of the prepared fats and oils was analyzed and shown in Table 3.

(Discussion in Table 3)
In Examples 1 to 4, the SFC at 30 ° C. was 20 to 30%, and the SFC at 35 ° C. was 15 to 25%.

Preparation of oils and fats using margarine In all cases of Examples 1 to 4 and Comparative Examples 1 to 4, rapeseed oil was used as the liquid oil. Margarine was prototyped using a plastic oil / fat composition containing 20% by weight of each hard stock with respect to 80% by weight of rapeseed oil.
The plastic fat and oil composition was prepared in a proportion of 84 parts by weight and 16 parts by weight of water. Subsequently, 0.01 parts by weight of glycerin fatty acid ester was added as an emulsifier. After pre-emulsifying the above mixture with a homomixer, a prototype was made with a combinator. We evaluated the prototype margarine.

(Hardness evaluation)
The obtained product was cut into cubes having a side of 5 ± 1 cm, placed in an incubator at each temperature, and the hardness after 24 hours was measured. The hardness was measured by using a "leometer" manufactured by Fudo Kogyo Co., Ltd. and pressing a plunger having a diameter of 1 cm at a speed of 5 cm / min. The results are shown in Table 4 (unit: g).

The temperature at which the hardness was about 300 to 400 g was defined as the optimum product temperature. In Examples 1 to 4 and Comparative Example 3, the optimum product temperature for use was 15 to 20 ° C. It can be seen that it can be applied to a very wide range of usage environments. On the other hand, in the case of Comparative Example 1, the optimum product temperature for use is 15 ° C. or lower, and in the case of Comparative Example 4, the temperature is 10 ° C. or lower, and the product can be used only in a limited usage environment. Comparative Example 2 has a poor usability because it is too hard even at 20 ° C. or higher.

Subsequently, the margarine after refrigerating at 5 ° C. for 48 hours was evaluated according to the following criteria for the items shown in Table 5, and the results are shown in Table 5.
Evaluation criteria ◎: Very good ○: Good
△: Defective
×: Remarkably defective

The margarines prototyped in Examples 1 to 4 had good quality in all the evaluation items. In Comparative Examples 1 and 3, margarine having good plasticity and melting in the mouth could be prototyped, but the result was inferior to that of Examples 1 and 2 due to the stain removal of the liquid oil. On the contrary, in Comparative Example 2, the stain of the liquid oil was good, but the result was inferior to that of Examples 1 to 4. Comparative Example 4 had a good melting in the mouth, but the result was inferior to that of Examples 1 to 4 in particular due to the appearance of stains on the liquid oil.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a random transesterified oil having a reduced saturated fatty acid content and good physical properties for use as a hard stock of a plastic fat composition.

Claims (5)

Random ester exchange for hard stock, which contains 60% by weight or less of saturated fatty acid in the constituent fatty acids, contains medium-chain fatty acid-bound fat (MCT) as a raw material for random ester exchange, and satisfies all of the following (A) to (D). oil.
(A) The content of saturated fatty acids having 6 to 10 carbon atoms in the constituent fatty acid composition is 0.5 to 10% by mass.
(B) The content of saturated fatty acids having 16 to 22 carbon atoms in the constituent fatty acid composition is 50 to 60% by mass.
(C) Stearic acid content in the constituent fatty acid composition is 20 to 50% by mass.
(D) The mass ratio of stearic acid to the total content of saturated fatty acids having 8 to 10 carbon atoms is 5 to 17 The random transesterification oil for hard stock according to claim 1, wherein the rising melting point is 40 ° C. or higher and 55 ° C. or lower. The random transesterification oil for hard stock according to claim 1 or 2, wherein the SFC at 30 ° C. is 20 to 30% and the SFC at 35 ° C. is 15 to 25%. A plastic oil / fat composition containing 5 to 30% by weight of the random transesterified oil for hard stock according to any one of claims 1 to 3 and 70 to 95% by weight of a liquid oil. Production of a plastic fat and oil composition, which comprises blending 5 to 30% by mass of the random transesterified oil for hard stock according to any one of claims 1 to 3 and 70 to 95% by mass of a liquid oil. Method.