WO2022065416A1

WO2022065416A1 - Random transesterified oil

Info

Publication number: WO2022065416A1
Application number: PCT/JP2021/035012
Authority: WO
Inventors: 遂人堀
Original assignee: 不二製油グループ本社株式会社; 不二製油株式会社
Priority date: 2020-09-25
Filing date: 2021-09-24
Publication date: 2022-03-31
Also published as: JPWO2022065416A1; JP7078200B1

Abstract

The present invention addresses the problem of providing oily foods having excellent heat resistance. This random transesterified oil contains, as a raw material, medium-chain triglyceride (MCT) oil.

Description

Random transesterification oil

The present invention relates to a random transesterified oil capable of providing an oil-based food product having excellent heat resistance.

Oil-based foods that require heat resistance and shape retention include solid roux, margarine, shortening, etc. used in processed foods such as curry, hayashi, and stew, which are obtained by heating and mixing wheat flour, edible oils and fats, seasonings, etc. Examples thereof include plastic oil and fat compositions of.

Patent Documents 1 and 2 disclose the heat-resistant and shape-retaining properties of solid roux used in processed foods such as curry, hayashi, and stew.

Japanese Unexamined Patent Publication No. 2009-81999 International Publication No. 2016/121604

Atmospheric temperature may rise during distribution and storage during high temperature in summer or when developing products in tropical regions such as Southeast Asia, and it has shape retention even in such an environment, and the liquid oil component stains. Oil-based foods with excellent heat resistance are desired because they are required not to be released.

The present inventors considered the improvement of heat resistance of oil-based foods. The hardness of the fats and oils used affects the heat resistance of oily foods, but at high temperatures, the fats and oils may melt and the shape may not be maintained.

In order to improve the heat resistance at high temperatures, the heat resistance can be improved by increasing the melting point of the fats and oils used and increasing the blending amount of the fats and oils having a high melting point. However, increasing the melting point of the fat or oil or increasing the blending amount of the high melting point fat or oil may cause problems such as deterioration of the texture of processed foods using oily foods.

Patent Document 1 exhibits better shape retention and solubility in comparison with partially hydrogenated beef tallow or lard with respect to the oil and fat used for solid roux, but the content of extremely hydrogenated oil is relatively high. Therefore, the texture was inferior because undissolved residue was generated during cooking or solidification occurred during eating.

Patent Document 2 describes a dough for solid ruu containing 1 to 20% by weight of one or more sugars selected from sugar, maltose, trehalose, fructose, palatinose, reduced palatinose, maltitol, erythritol, lactitol and sorbitol. , The heat treatment at 100 to 160 ° C. was indispensable.

The object of the oil-based food of the present invention is to sufficiently improve the heat resistance. However, if oils and fats having a high melting point are used in an attempt to improve heat resistance, the texture of processed foods using oily foods may deteriorate, and it is difficult to achieve both heat resistance and texture.
Therefore, an object of the present invention is to provide an oil-based food having excellent heat resistance and an excellent texture of processed foods using oil-based foods.

As a result of diligent research in view of the above circumstances, the present inventor has completed the present invention by containing medium-chain fatty acid-bound fat (MCT) as a raw material for random transesterification.

That is, the present invention
(1) A random transesterified oil containing medium-chain fatty acid-bound fat (MCT) as a raw material for random transesterification and satisfying 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 behenic acid in the constituent fatty acid composition is 0.5 to 5% by mass.
(C) The mass ratio of stearic acid to palmitic acid is 0.5 to 15.
(D) The random transesterification oil of (1), which has an elevated melting point of 50 ° C. or higher and 60 ° C. or lower (2) a mass ratio of stearic acid to palmitic acid of 0.5 to 10.
(3) Random transesterification oil of (1) or (2) having an SFC of 15% or less held at 40 ° C. for 10 minutes.
(4) The random transesterified oil of (1) or (2), wherein the content of palmitic acid in the constituent fatty acid composition is 2 to 40% by mass.
(5) The random transesterified oil of (3), wherein the content of palmitic acid in the constituent fatty acid composition is 2 to 40% by mass.
(6) Oil-based foods using any of the random transesterified oils (1) to (5).
(7) A method for improving the heat resistance of oil-based foods using the random transesterified oil of (1) or (2),
(8) A method for improving the heat resistance of oil-based foods using the random transesterified oil of (3),
(9) A method for improving the heat resistance of oil-based foods using the random transesterified oil of (4) or (5),
(10) A method for improving the texture of processed foods using the oily foods of (6),
(11) The oily food of (6), which is a solid roux,
(12) A random transesterified oil according to any one of (1) to (5), which is a hard stock used for a plastic oil / fat composition.
(13) A plastic oil / fat composition containing 30 to 5% by mass of the random transesterified oil according to any one of (1) to (5) and 70 to 95% by mass of a liquid oil.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide an oil-based food product having excellent heat resistance and an excellent texture of processed food products using oil-based food products.
As a preferred embodiment, according to the present invention, it is possible to provide an oil-based food product having excellent summer shape retention, resistance to exudation of liquid oil components, and resistance to white change on the surface.
As a more preferable embodiment, when used for solid roux, the heat resistance of the solid roux can be improved, particularly in an environment of 50 ° C. or higher. The processed food produced by using the solid roux has good fluidity at the time of eating, and can maintain a good texture at the time of eating.

The random transesterified oil of the present invention contains medium-chain fatty acid-bound fat (MCT) as a raw material for random transesterification. The medium-chain fatty acid-bound fat (MCT) in the present invention is a fat and 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 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 behenic acid in the constituent fatty acid composition is 0.5 to 5% by mass.
(C) The mass ratio of stearic acid to palmitic acid is 0.5 to 15.
(D) The rising melting point is 50 ° C or higher and 60 ° C or lower.

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 processed foods using oily foods.

The random transesterified oil of the present invention has a behenic acid content of 0.5 to 5% by mass in the (B) constituent fatty acid composition. Within such a numerical range, good heat resistance in oil-based foods and good texture in processed foods using oil-based foods can be obtained.

The random transesterified oil of the present invention has (C) a mass ratio of stearic acid to palmitic acid of 0.5 to 15, preferably 0.5 to 10. Within such a numerical range, good heat resistance in oil-based foods and good texture in processed foods using oil-based foods can be obtained.

The random transesterified oil of the present invention (D) has a rising melting point of 50 ° C. or higher and 60 ° C. or lower. Within such a numerical range, good heat resistance can be obtained in oil-based foods.

The random transesterified oil of the present invention preferably has an SFC of 15% or less held at 40 ° C. for 10 minutes. Within such a numerical range, a good texture can be obtained in processed foods using oily foods.
As a preferred embodiment, the SFC held at 40 ° C. for 10 minutes can evaluate the physical characteristics of processed foods prepared using oily foods at the time of eating.
When the processed food is curry, when the SFC held at 40 ° C. for 10 minutes is 15% or less, the prepared curry has good fluidity at the time of eating and can maintain a good texture at the time of eating. can.

The random transesterified oil of the present invention preferably has a palmitic acid content of 2 to 40% by mass, more preferably 2 to 30% by mass, still more preferably 2 to 20% by mass in the constituent fatty acid composition. .. Within such a numerical range, good heat resistance in oil-based foods and good texture in processed foods using oil-based foods can be obtained.

The oil and fat composition for solid oily foods of the present invention may be adjusted according to the above-mentioned conditions, but it is a large oil and fat that can be used as a raw material for ester-exchanged oils other than medium-chain fatty acid-bound oils and fats (MCT). Vegetable fats 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, palm oil, palm kernel oil, and animal fats such as milk fat, beef fat, and pork fat. , And those cured oils, fractionated oils, cured fractionated oils, fractionated cured oils, processed oils and fats subjected to ester exchange and the like, and mixed oils and fats thereof can be exemplified.
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 and the like 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.
Rapeseed extremely hydrogenated oil and palm extremely hydrogenated oil are in the range of 40% by mass to 70% by mass, hyerusic acid rapeseed extremely hydrogenated oil is in the range of 1% by mass to 10% by mass, and sunflower oil and palm fractionated oil are in the range of 15% by mass to 45% by mass. It is more preferable to mix with.

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 transesterified oil of the present invention can be used for oil-based foods that require heat resistance. Examples of oil-based foods include hard stocks used in plastic fat and oil compositions such as solid roux, margarine, and shortening used in processed foods such as curry, hayashi, and stew.

Solid roux used in processed foods such as curry, hayashi, and stew is solid at room temperature, and is widely used for home use, restaurants, school lunches, and other commercial purposes due to its ease of cooking. ..

The blending amount of the random transesterified oil used for the solid roux is not particularly limited, but is preferably 20 to 100% by mass, more preferably 25 to 75% by mass in the fat and oil contained in the solid roux. If it is less than 20% by mass, the heat resistance of the solid roux is impaired, which is not preferable.

Other ingredients used in solid roux include spices such as curry, cocoa mass, cocoa powder, full-fat milk powder, defatted milk powder, buttermilk powder, whey powder, yogurt powder and other dairy products, grains, beans, vegetables, meat, etc. Seafood, fruits, fruit juice, coffee, nut paste, plant proteins such as wheat protein and soybean protein, food materials such as eggs and various processed egg products, emulsifiers, thickening stabilizers, salting agents such as salt and potassium chloride, acetic acid, Examples thereof include acidulants such as lactic acid, sweeteners such as sugars and sugar alcohols, stevia and aspartame, coloring agents such as β-carotene and caramel, and antioxidants such as tocopherol and tea extract. Such food materials and food additives may be used alone or in combination of two or more.

Examples of the emulsifier include lecithin, glycerin fatty acid ester, glycerin acetic acid fatty acid ester, glycerin lactic acid fatty acid ester, glycerin succinic acid fatty acid ester, glycerin diacetyl tartrate acid fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, and sucrose acetate isobutyric acid ester. , Polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester, propylene glycol fatty acid ester, stearoyl lactate calcium, stearoyl lactate sodium, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monoglyceride and the like can be exemplified.

Examples of the thickening stabilizer include guar gum, locust bean gum, carrageenan, arabic gum, alginic acid, pectin, xanthan gum, pullulan, tamarind seed gum, psyllium seed gum, crystalline cellulose, methyl cellulose, carboxymethyl cellulose, agar, glucomannan, and gelatin. , Gum, etc. can be exemplified.

The solid roux using the random ester exchange oil of the present invention includes various sauces such as curry, white sauce, hayashi sauce, and demiglace sauce, various stews such as curry stew, white stew, and demiglace stew, fillings for bread, and toppings. It can be widely used for processed foods such as.

The random ester exchange oil of the present invention can be used as a hard stock of plastic fat and oil compositions such as margarine and shortening, but glycerin fatty acid ester, sucrose fatty acid ester, propylene glycol fatty acid ester, polyglycerin fatty acid ester, lecithin and the like can be used. The emulsifier of the above 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 a method for producing a plastic oil / fat composition, it can be produced by quenching and kneading a mixed oil containing 10 to 50% by weight of the hard stock and 50 to 90% by weight of liquid oil according to a conventional method. 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 are shown below, and the present invention will be described in more detail. In the example,% and part both mean mass-based.

(Analysis 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).
(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).
(SFC measurement method)
In the measurement of (SFC at each temperature) and (SFC maintained at 40 ° C.), 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.
(SFC held at 40 ° C)
After holding the fat and oil at 80 ° C for 10 minutes, hold it at 60 ° C for 30 minutes to completely dissolve the fat and oil, hold it at 40 ° C, and measure the SFC (solid fat content) after 3 to 30 minutes. .. In the present invention, SFC at 40 ° C. after 10 minutes has passed is referred to as SFC held at 40 ° C. for 10 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 fatty acids is 60:40, manufactured by 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.

Various analytical values were compared and evaluated in Table 2.

(Evaluation of random transesterified oil-1)
In order to obtain oil-based foods with excellent heat resistance, the target quality was set to have a rising melting point of 50 ° C. or higher and 60 ° C. or lower for the random transesterified oil, and the numerical range of (A) to (C) below was used as an index.
(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 behenic acid in the constituent fatty acid composition is 0.5 to 5% by mass.
(C) The mass ratio of stearic acid to palmitic acid is 0.5 to 15.

(Discussion in Table 2)
The random transesterified oils of Examples 1 to 3 contain medium-chain fatty acid-bound fats and oils (MCT) as raw materials for random transesterification, satisfy all the numerical ranges of (A) to (C), and have an elevated melting point. However, the target quality of 50 ° C or higher and 60 ° C or lower was obtained.
-The rising melting point of Comparative Example 1, which does not satisfy the above (A) and (C), was 47.0 ° C., and the target quality could not be obtained.

SFC maintained at 40 ° C was measured and compared in Table 3.

(Random transesterification oil evaluation-2)
As an index of good texture and good melting in the mouth of oil-based foods using random transesterified oil, the target quality was that the SFC held at 40 ° C. for 10 minutes was 15% or less.

(Discussion in Table 3)
-The random transesterified oils of Examples 1 to 3 obtained the target quality when the SFC held at 40 ° C. for 10 minutes was 15% or less.
In Comparative Example 2 which does not contain medium-chain fatty acid-bound fat (MCT) as a raw material for random transesterification and does not satisfy the above (A), SFC held at 40 ° C. for 10 minutes is 21.5%, and the target quality is I couldn't get it.

The analytical values were compared in Table 4.

(Comparison of random transesterified oils)

(Comparison of Table 4)
-From Table 5, the preferred embodiment of the present invention, which is satisfied by Examples 1 to 3, is
(A) The content of palmitic acid in the constituent fatty acid composition is 2 to 40% by mass, more preferably 2 to 35% by mass, still more preferably 2 to 30% by mass, still more preferably 2 to 25% by mass. ..
(B) The content of stearic acid in the constituent fatty acid composition is 10 to 60% by mass, more preferably 15 to 60% by mass, still more preferably 20 to 60% by mass, still more preferably 30 to 60% by mass. ..
The total of (a) and (b) is 45% by mass to 75% by mass, more preferably 45 to 70% by mass, still more preferably 50 to 70% by mass, and even more preferably 50 to 65% by mass.
(C) The content of saturated fatty acid having 6 to 18 carbon atoms in the constituent fatty acid composition is 45 to 85% by mass, more preferably 45 to 80% by mass, and further preferably 50 to 80% by mass.
(D) In the constituent fatty acid composition, the unsaturated fatty acid content is 20 to 50% by mass, more preferably 25 to 50% by mass, and further preferably 25 to 45% by mass.

(Evaluation of heat resistance at 50 ° C)
-In order to evaluate the heat resistance at 50 ° C., a solid roux was prepared and evaluated according to the following formulation and method.

(Method for producing solid roux and method for evaluating heat resistance at 50 ° C)
・ Put salt and monosodium glutamate in an iron mortar and crush.
・ Keep heat except lecithin at 55 ℃.
・ Put all but fats and lecithin into a Kenwood mixer.
・ Add transesterification oil and canola oil little by little while stirring.
-Once the ingredients are gathered, dissolve the lecithin in the remaining transesterification oil and canola oil and stir.
・ After stirring, fill a plastic container with 50 g.
・ After quenching and solidifying at 5 ° C (1 hour), aging at 15 ° C (Over night).
-After storing in an incubator at 50 ° C. for 2 hours, the plastic container was turned over by 90 ° and the state of fats and oils was evaluated according to the following evaluation criteria. The evaluation results are shown in Table 6.

(50 ° C heat resistance evaluation standard)
〇: The solid roux is completely solidified and has no fluidity and does not drip.
Δ: The solid roux is observed to have started to discolor, but it has no fluidity and does not drip.
X: Solid roux is partially melted and has fluidity, so it drips.

(Discussion in Table 6)
-Good results were obtained in the evaluation of heat resistance at 50 ° C. for the solid roux using the random transesterified oils of Examples 1 to 3.
-Comparative Example 1 was a result of inferior heat resistance at 50 ° C.

(Evaluation of processed foods)
Processed foods were prepared using random transesterified oil and the texture was evaluated.

(Curry making)
-Curry was prepared as a processed food according to the following formulation and preparation method, and the evaluation results are shown in Table 8.

(How to make curry)
-In the dissolved state, a commercially available solid roux and a random transesterified oil were mixed to obtain a roux composition.
-The roux composition and consomme were added to water according to the formulation, and then heated to 80 ° C. with stirring.
After reaching 80 ° C., stirring was continued for 10 minutes while maintaining the temperature, and then the oil and fat to be examined were added according to the formulation.
・ After stirring at 80 ° C. for 5 minutes, a tasting was performed to evaluate the texture and flavor.

(Curry texture evaluation criteria)
〇: Almost no oily feeling is felt, and the flavor release is also good.
Δ: A slight oily feeling is felt, and the flavor release is slightly poor.
×: A feeling of oiliness is felt, and the flavor release is clearly bad.

(Discussion in Table 8)
-Good evaluation results were obtained for the texture of the curry using the random transesterified oils of Examples 1 to 3.
-In Comparative Example 2, the texture of the curry was inferior.
-In Examples 1 to 3, good results were obtained in both heat resistance at 50 ° C. and texture of curry.

According to the present invention, it is possible to provide an oil-based food product having excellent heat resistance.

Claims

A random transesterified oil containing medium-chain fatty acid-bound fat (MCT) as a raw material for random transesterification and satisfying 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 behenic acid in the constituent fatty acid composition is 0.5 to 5% by mass.
(C) The mass ratio of stearic acid to palmitic acid is 0.5 to 15.
(D) The rising melting point is 50 ° C or higher and 60 ° C or lower.
The random transesterification oil according to claim 1, wherein the content mass ratio of stearic acid to palmitic acid is 0.5 to 10.
The random transesterification oil according to claim 1 or 2, wherein the SFC held at 40 ° C. for 10 minutes is 15% or less.
The random transesterified oil according to claim 1 or 2, wherein the content of palmitic acid in the constituent fatty acid composition is 2 to 40% by mass.
The random transesterified oil according to claim 3, wherein the content of palmitic acid in the constituent fatty acid composition is 2 to 40% by mass.
An oily food product using the random transesterified oil according to any one of claims 1 to 5.
A method for improving the heat resistance of oil-based foods using the random transesterified oil according to claim 1 or 2.
A method for improving the heat resistance of oil-based foods using the random transesterified oil according to claim 3.
A method for improving the heat resistance of oil-based foods using the random transesterified oil according to claim 4 or 5.
A method for improving the texture of processed foods using the oily foods according to claim 6.
The oily food according to claim 6, which is a solid roux.
The random transesterification oil according to any one of claims 1 to 5, which is a hard stock used for a plastic oil / fat composition.
A plastic oil / fat composition containing 30 to 5% by mass of the random transesterified oil and 70 to 95% by mass of the liquid oil according to any one of claims 1 to 5.